Not Boring (with Packy McCormick)｜Acquired

Okay, we got to get you over 100K.

This episode is a failure if we don't get you over 100K subscribers.

All right, so let me timestamp where we are right now, just so we know what we need to do.

So we are at 88,460.

Oh, we can so do that.

Oh, we'll juice this.

Okay.

Welcome to Season 9, Episode 6 of Acquired, the podcast about great technology companies and the stories and playbooks behind them.

I'm Ben Gilbert and I am the co-founder and managing director of Seattle-based Pioneer Square Labs and our venture fund, PSL Ventures.

And I'm David Rosenthal.

And I am an angel investor based in San Francisco.

And I am back, sort of, from paternity leave.

An abbreviated partial ongoing paternity leave.

Yeah, we're making it work.

And we are your hosts.

Well, today we have a first for Acquired.

We are covering a business that is only one person.

Not boring.

The newsletter gone media and investment empire run by Paki McCormick.

I did some research last night.

Not Boring is the number one substack newsletter on business.

If Paki decided to switch to the technology category, from everything I can tell he would be number one there too.

In fact, even in the crypto category, there are only two newsletters with more reach, and they've existed much longer.

Not Boring is only a year and a half old.

The Not Boring Story isn't just impressive because of its explosive growth.

Packy is reinventing the media business model and simultaneously, the startup investing business model.

He's done all this with a very distinct personal flair, writing in a unique whimsical voice that makes us all just want to have fun and play the great online game.

We're very lucky that he is a part of our Liquid Super team here at Acquired so he could join us today live to help tell the story.

Welcome, Paki.

That was amazing.

Thank you, Ben and David.

Great to be here.

I was doing my best Paki impression, trying to write whimsically in the unique style you've cultivated.

It was beautiful.

Get some good buzzword bingo in there with not boring piece titles over the I want to say years, but it hasn't been.

It feels like years.

It feels like you've always been here.

I had two more.

I cut them.

It turned into just like a long series of not boring titles.

Anyway, Paki, we do it to let you know, this is not going to be all softballs.

We're going to like actually do the full acquired deep dive here, if that's okay with you.

I mean acquired is.

I think, particularly for the first year when I wrote about SoftBank, when I wrote about Tencent, when I wrote about all these companies getting deep, the work that you did to go deep on those companies was hugely instrumental in being able to write those pieces.

I would expect nothing less than the full acquired treatment.

All right, let's do this.

Well listeners, we have a huge announcement, a gigantic, exciting piece of news to share with all of you.

For the 98% of you out there who have not joined the That is right.

That includes our series on VC fundamentals and our startup deep dives on pricing marketplaces, SaaS investing with top investors and founders.

And in fact we are about to drop an episode right there in that feed where I interview 15-year president of Blue Origin, Rob Meyerson, on how he sees the space landscape today.

Now, of course, members of the paid LP community still get great benefits like exclusive access to new episode for two weeks before we drop it in the public feed.

The ability to join LP calls Zoom book club.

You know all this stuff.

But if you aren't an LP and you really want to start getting these episodes, you can click the link in the show notes or go search Acquired LP.

Show wherever you get your podcasts and subscribe.

Thank you to all of our LPs for being on this journey with us.

We are very excited to now share all this content more broadly.

There's some good stuff.

Ben, you interviewed Joseph Gordon-Levitt the other day on the LP show.

Super fun.

Yeah.

So fun.

You guys kind of look alike.

We've gotten that a few times.

Since Joe is a professional Hollywood actor, I take that as a great, unbelievable compliment.

So thank you, Paki.

All right, listeners, now is a great time to thank a new friend of the show, Koifin.

And it's funny, they're new, but actually I've been using their product for years.

My research project for every single new acquired episode involves Koifin.

So when they reached out to sponsor the show, I thought, well, this is convenient.

Indeed.

So Coifin is a financial research tool loved by both individual investors and financial advisors.

Individuals use it for stock research, graphing financials and portfolio tracking, and financial advisors use it to build model portfolios and create client proposals.

They have live market data and powerful analytics tools.

So it's kind of like a Bloomberg terminal, except without the huge price tag, right?

Yes, essentially.

It's a web app, and it's totally self-serve.

I've actually not talked to anyone at the company for the first few years that I used it.

So Koifin is a product that the broader market, like all acquired listeners, would use, not just Wall Street investment bankers.

It's where I pull things like growth rate or gross margins or the PE ratio or revenue multiples for every company we study.

And you can compare these things over time with historical graphs or against other companies.

It's often what I use when we're studying private companies too, like Rolex or Mars or IKEA, to look at the comparables, to estimate what these companies would be worth if they were public.

They also have a screener that lets you filter across thousands of stocks, so you can quickly surface investment ideas.

Yeah.

So the general idea is, if you're someone who's used to living in data, you should have that at your fingertips as you think about investing.

Exactly.

It's got these great graphs for data visualization wrapped around institutional grade data.

So if you want to understand what assumptions are baked into the stock price today, Coifin is for you.

I was about to say that acquired listeners have a great offer.

But Koifin's free product is actually already really robust.

Which is what I was using for years.

I know, I know.

But indeed for Acquired listeners and also for you, Ben.

If you go to koifincom slash acquired and you end up upgrading to paid, you'll get 20 off your first year.

Our thanks to Koifin.

That's K-O-Y-F-I-N dot com slash acquired or click the link in the show notes.

Well before we dive into history and facts, we should say this show is not investment advice, though David and I are both investors in multiple, not boring entities.

So not only are we conflicted, we want to be extremely open about that.

We definitely have investments that we are discussing today.

This show is for informational and entertainment purposes only, and I promise you it will be both of those.

All right, look, we're going to do the whole acquired treatment on you, Paki.

But the first place I went when I was like, all right, I would start researching, build the script here for the not boring story.

I went to your LinkedIn.

You know, I know that's kind of a boomer thing to do, but I did.

You are listed there as the quote unquote founder of not boring.

How on earth did you decide on what to put there?

It's a really tough question for me.

Still, when I get asked to do if I'm going on a panel or joining a podcast or something I get asked to send over a short bio.

Or CNBC.

Or if I'm on CNBC, I get asked for a short bio.

And sometimes it's writer, sometimes it's author, sometimes it's founder.

I don't know really what I do or how to describe what I do.

And then if you mix that in with Not Boring Capital, the whole thing gets very confusing.

Founder feels like a catch-all.

I did definitely start this thing.

And so anything else beyond that, I think is subject to change.

Love it.

You are definitely the founder of the Not Boring Empire.

All right.

So let's tell the story.

I'm assuming you were born in either 1986 or 1987.

1987.

January 26th, the same birthday as Wayne Gretzky, Vince Carter, a lot of the great athletes.

Okay, so January 26 1987, in Bryn Mawr Pennsylvania, just outside Philadelphia, there's the birth of a baby boy named Patrick.

Patrick.

Also known as Packy McCormick.

So Urban Dictionary tells me that Packy is a very common diminutive form of the name Patrick that is especially popular amongst residents of County Cork, Ireland.

Is that where your family is originally from?

Yes.

I believe so.

My dad has done kind of the ancestry.com deep dives on his side of the family.

I think we're probably fourth generation over here.

And so we think it's County Cork, but not a hundred percent positive.

Nice.

All in the Philadelphia area.

All in kind of the Lehigh Valley.

Allentown is where my dad grew up.

We have a bunch of family in Scranton.

So Joe Biden country.

Yeah.

Billy Joel growing up in Allentown.

What were you like as a kid?

Any little glimmers of the future not boring empire that were popping up when you were growing up?

Yeah, I used to make these little books or newspapers on post-it notes.

I also have this one that was called Golden Memories of a Young Boy's Life.

And so I had all these au pairs and they would take me in the women's locker room at the pool or something like that.

And I was a five-year-old kid and I would come home and draw stick figures of boobs in this little book called Golden Memories of a Young Boy's Life.

So that was probably the earliest version of Not Boring.

You could have taken a very different career direction after that.

I could have.

I wasn't a particularly good artist.

Which actually has carried through perfectly.

Perfectly to today.

I'm still not a good artist.

I think it's part of the charm.

But even in high school or middle school we had an eighth grade teacher, Mr Algeo, who would make you write a composition or an essay if you got in trouble.

So for me, I would actually sometimes try to get in trouble.

Because for most kids, that's punishment.

For me, if I have to write as much as you write, I couldn't do it.

There's no way.

I mean, I did cross country and track in high school too.

And that was kind of a similar vibe, where for most people that's punishment, making them run many miles.

And I love that.

But Mr. Algeo, you'd have to write a composition.

And I would love to do it because I would try to write a composition that was so funny that Mr Algeo would let me read it in front of the class.

Or in high school, I would try to write essays that were a combination of very well done and well researched and all that but funny, so that even my most serious teachers would have to laugh and give me a good grade, despite the fact that I turned them into a joke.

So I think kind of always combination of class clown with a backing of kind of serious research.

It's pretty rare to find those two combinations together in one person, right?

Somebody who is both the class clown and has a work ethic.

And I think that comes through in Not Boring.

All of us who read every or close to every one of your posts, I think that's the charm.

That is the style, is that you're diligent.

You've written many times about how the process works and how you go into your basement and spend the time and do the research and start writing and tear it down and write something.

I mean, there's real diligence there.

And for sure, you are the class clown of serious business newsletter writers.

If there are people who've read every or close to every Not Boring, thank you.

I think it takes a work ethic to read all of Not Boring.

It's been probably close to a million words in a year and a half at this point.

To get people to read that much, it has to be both kind of informative and entertaining.

I think I'm using your phrase here when I say that the reason it works is because you don't put on your serious business pants.

I don't even own serious business pants.

So where does the work ethic come from?

That is certainly from both of my parents.

My dad, as I said, was a consultant at Arthur Anderson and would literally fly to Germany for a day and come home, or fly down to Miami to go to Miami Herald and then make it home by four o'clock that night to take us to the fair and then fly back out the next morning.

So it was working... all of the time.

My mom was getting her PhD and working and raising two kids.

And so, like both entrepreneurial, they both ended up starting their own kind of consulting practices.

Both incredible work ethic.

And then there was just a way that they parented.

My absolute favorite story growing up was when I was, I think, in fifth grade.

I had told my parents everything was going really really well.

I was probably going to get straight A's, maybe like a B+, but probably not.

And then I got my report card.

And I remember my dad was coming home from a business trip and he was a fancy consultant.

So he had a cell phone way back in the day in his car.

We got our report card and my mom made me call my dad and tell him the grades that I got.

And it was like science, A, English, A, French, C+.

And he's like, all right, Packy, I'm going to be home in an hour.

By the time that I get home, I want all of your certificates, all of your trophies, anything that would suggest that you might be a winner.

I want them in a box in the attic.

We're calling that box the loser box because you're a loser.

What?

And my mom said that my dad went to like the Mo Mar Gaddafi school of parenting for this.

I actually think it was awesome, because what he was mad about wasn't that I got a C plus, like that wasn't the big deal.

It was that I lied all semester and said that I was doing really well in the class.

Uh...

And so I thought that was the best parenting lesson that I could have ever received, because it was a really good lesson both in honesty and in work ethic.

Because after that I actually started trying in French and I ended up taking it all the way through college and got pretty good at it.

I can't really speak it anymore.

But it was a really good lesson that if you're not going to do well, at least be honest about the fact that you're not going to do well.

And so now I think when I get things wrong and not boring, I blare it from the rooftops and probably comes back to that moment.

Yeah, you feel like an intense need to own the mistake.

There's a tweet that you had around the crypto winter where you said them's the rules.

You got to play fair.

And I think you were owning the fact that a lot of things that you thought were going to go up did not go up.

I mean our ideas dinner podcast.

I think is a testament to the fact that I get things wrong all the time.

Oh, we all do.

So, okay.

So you go to Duke.

You were on the debate team at Duke, right?

I was.

Shocking.

We were able to unearth some pretty awesome photos from that time that maybe we'll link to in the show notes.

I was incredibly cool.

I was in the debate club.

I was in an acapella group.

There were a couple of big all-male acapella groups.

I was the cool one on the debate team.

Me and my partner, who was my best friend from high school also, we were the cool team.

So I was like in all the nerdy things and tried to be cooler than I was probably in all of those things.

But that was certainly my kind of college.

Vibe was just getting involved in a lot of different things.

So, OK, you graduated in 2009, which I mean, I remember I graduated in 07.

I sailed through.

I was a French literature major.

I get the investment banking job.

I'm like, oh, this is good.

Then, of course, I got my butt kicked when I actually got to Wall Street.

But you got an investment banking job in 2009.

Like nobody got investment banking jobs in 2009.

This was the middle of the recession.

Also, just to drive David's point home here, even French lit majors could get investment banking jobs in 2007.

And by the time the door slammed in 2009, it took something special, Paki, for you to get there.

Yeah.

So I was, to be fully fair, kind of an investment banking light in public finance.

But it started the summer before in 2008 when I got my internship.

Things were actually still pretty good.

So I got an internship at Bank of America on the energy trading desk.

That was a wild experience in itself, because Bank of America's energy trading desk was all ex-Enron people.

And so they were not psyched to not be at Enron anymore and not psyched to be on a desk that didn't take physical delivery.

So there are two types of energy trading desks.

Some, like the bigger banks, Morgan Stanley, all of that which will take delivery, if they need to, of barrels of oil or whatever else.

Those are the kind of serious desks.

And then there are more, just pure financial desks, like we had at Bank of America.

Where Worked my butt off that summer.

There's the intern programs, and there's drinks and there's speeches, and there's all these things that you do when you're an intern on Wall Street.

My desk wouldn't let me go to any of those things.

I had to sit there.

And you don't do anything when you're a trading intern.

You literally sit on these people's shoulders.

You're not allowed to trade.

You're not licensed to trade.

Right.

You're not licensed.

You don't have the Series 7 and Series 63.

Is that the other one you need?

Exactly right.

So I asked them dumb questions throughout the day while they were trying to focus on these multimillion dollar trades.

It was like the worst experience.

They didn't like me being on the desk, but they also didn't want me to have any fun.

So they wouldn't let me go to any of the other things.

The summer before my internship, they didn't like the intern.

And so they took him out drinking until like 4am.

And then, when he came in a little bit late the next morning, they marched him to the HR team's office and got him fired.

And so that was the environment that I was coming into.

This is like liar's poker.

Totally.

But there's definitely the work ethic there where I just didn't let it bother me.

And so I got an offer to come back.

Bank of America merged with Merrill Lynch.

Merged, quote unquote.

So we bought them, but there were higher quality interns, quite frankly, at Merrill Lynch.

And so when we merged, I guess the other problem was we all got put on the Bank of America side in a rotational program.

So you got your offer from a specific desk, but you came back and had to rotate around different desks, whereas Merrill got hired into specific desks.

So all the Merrill kids, for both of those reasons, they were probably smarter than I was.

And they already had their desk kind of placement locked in.

They got their desk.

We rotated around and about half the people in the trading program ended up getting spit into public finance which, for those listening at home, is municipal bonds.

So I worked on the state of New Jersey's bonds that were backed by their tax obligations, or the Pennsylvania Turnpike, when they wanted to build new roads and issue debt to do that.

Wow.

That sounds kind of boring.

It was a little bit boring.

Hopefully that's the first of hundreds of funds throughout this podcast.

But yeah, it was boring, but I actually liked it.

I was number one in my class each of the years that I was there.

And I realized very early on because I had friends who were.

I remember a New York Times article came out about the fact that really top quality investment banking analysts were getting their PE offers way, way earlier.

And I think they quoted two of my friends in that article.

So I had friends who just love this stuff and I just was not one of those people.

So I knew that I'd want to get out of finance at some point.

And so I was really just playing to be in the top of my class and go to business school.

So you apply to business school and trollers of your LinkedIn profile will note that you do not have an MBA.

Yeah.

Walk us through that and what happens.

One other thing to add was while I was in finance, I started a company called Throgo, which was a terrible name.

I bought the site for something else.

And then I applied it to building this company that essentially took people from New York down to the Jersey Shore and to the Hamptons every weekend.

So it was a party bus ride.

It was so much fun, paid for my summers.

I took it way too seriously and thought that this was going to be my ticket to a great business school.

Applied to Stanford, got summarily rejected from GSB.

Ended up getting into Chicago, had my deposit down, was going to go.

And then one, I kind of visited and it was snowing and it was like April or May.

And I also found a company called Breather on AngelList and had just started a conversation with the founder of Breather where there was no guarantee of even an interview or anything.

But I asked Chicago if I could defer.

They told me, no, I couldn't defer your deposits already in.

If it were Harvard or Stanford, they would have let me defer.

But they know that people might try to say they want to defer so they can go to Harvard or Stanford.

So they wouldn't let me defer.

And so I just said, all right, cool.

Not going to business school.

I had already quit my job.

And so really spent kind of the next four months, I think, in this weird kind of winding interview process just with Breather, traded pretty actively, made some of the dumbest trades in the history of the world.

I think I bought Tesla during that summer at $29 and sold it.

I bought Facebook at 19, sold that, plowed a bunch into Apple options, into earnings, which is just not what you.

You're admitting your mistakes here.

I bought Bitcoin at 100, sold it at 150.

So I really had a fun summer where I was... You got some nice little returns here.

Some nice pops.

Yeah.

50% pot, pretty good.

So I had this kind of summer where I had no job.

I didn't have a future job lined up but I was interviewing and trading and making a bunch of dumb decisions that I think would kind of make me a better investor later on.

I will say it's hard to buy and hold when you're in that position in life where the cash is useful and a material amount of your net worth.

And you don't have a job.

Acquired wasn't around back then.

But you could listen to us have all these people on over the years saying how great it is to let compounding do its thing, or the Berkshire episodes, or even if you're a deep student of all this on your own and you know this, you kind of can't, at that point in your life when you're looking to A, learn or B, potentially use the cash in a pretty short period of time.

I mean.

The Bitcoin sale was a result of going to Oktoberfest with my friends while I was unemployed and they all had jobs in finance still.

And so they went out to the club and I was like, yeah, of course I can do that.

You know, I just got my bonus.

And then I woke up the next morning in the hotel and I was like, you know what?

That was stupid.

I shouldn't have done that.

I should have conserved my cash.

Let me sell these stupid Bitcoin so that I just kind of refill the coffers with USD.

And so that was why I sold all 38 of my Bitcoin at 150.

Whoa, whoa, whoa.

Okay, wait, we can't let you gloss over a couple things here.

We got to rewind.

Am I hearing you right that you wrote your business school application about starting a quote unquote company to bus drunk people from Manhattan to the Jersey Shore and the Hamptons?

I mean, it wasn't about busing drunk people from New York to the Jersey Shore and the Hamptons.

It was about community and bringing people together.

I mean people who had never met somebody going to the beach town that they were going to made friends.

People got married who met on the party bus.

It was about community.

But yeah, no, seriously, that is how I tried to spend my business school essays.

Wait, wait, wait.

So, to quote a writer named Paki McCormick, the hard part about being a great writer is that you can convince people that a really bad idea is a really great idea.

And you just did that to me.

Yeah.

That is another one of those formative experiences where obviously it wasn't a startup.

It was startup light.

It was stupid and it was fun and it paid for my summers and all of that.

When I was applying to Breather though, I had done marketing.

I had done operations.

I had to deal with a bunch of shitty situations.

And so that company in particular, the CEO is kind of an iconoclast.

He runs a company now called Practice.

Julian, great guy.

But he didn't care at all about the finance background, other than it proved that I could work hard and maybe I could help with some business stuff.

But he really cared that I got my hands dirty and had to deal with all of the junk in just being kind of a one person running this company.

So it was definitely a silly experience, but I think it also kind of helped with the next chapter.

What was the name of the party best company?

Throgo.

I actually don't think I've actually technically shut down that LLC.

So I have one of those too.

It's funny, actually doing that gritty stuff of dealing with tour bus operators.

You got to do that when you're an entrepreneur.

And so many people that go to business school think oh, I'm going to get all this glory and start some internet company.

And it's like, you got to be willing to shovel your fair share of manure here.

I mean, that's like the Chris Saka quote about.

You know he won't hire or work with anybody who hasn't had just a shitty job growing up.

So, you know, I'd wash dishes.

I had my fair share of kind of those types of jobs.

And I think that all helps because I mean, we'll get to be there.

But that was my first year's experience was doing that exact same thing.

Yeah.

So let's jump to Breather.

So that summer I had thrown away my money in business school as well.

That deposit was gone.

Terrible summer from a financial perspective.

But the way that I was thinking about it was like I'm either going to spend the next two years not making a single dollar and paying for business school and racking up debt doing that, or Or I can go somewhere anywhere really that will pay me more than negative dollars and learn on the job and get that experience.

My interview process at Breather was doing a bunch of really random things.

I don't think they knew what they were doing from a hiring perspective.

I wrote the JD for the job that I ended up getting, which was New York City general manager.

How big was the company at that point?

It was six people in Montreal.

So I was going to be our first US employee there.

One of my jobs was Julian said there's a guy at Uber who does a job similar to the one that you want to do.

Go track him down and then get him to interview you.

And then he'll tell me what he thinks.

And so that ended up being Josh Moore, who was the New York City general manager at Uber.

So I met him.

He's remained a friend.

That was a lot of fun.

I think he works at Levels now.

Yeah, exactly.

He's at Super Sapiens competitor Levels now.

And that was one.

Another was our other co-founder, Katarina, was a designer by background.

And so she was like go to a Marriott business lobby and go to the Ace Hotel lobby and then make a presentation on why they're different.

And they're obviously very different.

But I'm not a designer, as everybody who reads Not Boring knows.

And so I had this whole thing about the vibe of both of the spaces.

And it wasn't particularly good, but the fact that I did it is probably what they wanted to see.

Yeah.

I learned later that it came down to me and somebody who ended up working for the company later.

Who's way more talented and smarter than I am?

And Julian and Katarina went point by point on both of us in the lobby actually of the Ace Hotel the night before they made their decision.

And I won by one point and got the job, or else I would have had four months down the drain and absolutely nothing.

So I ended up getting the job.

So what Breather did was it rented out meeting and workspace and beginning these very small meeting rooms for as little as half an hour at a time.

So my job was twofold.

My job was first convince landlords to rent spaces to this random Canadian company that wants random people to come in and out of the building for half an hour at a time throughout the day.

So that was challenge number one.

And I literally got on my knees.

And in one case this is actually what I mean literally got on my knees and begged to one of the landlords to give us the space.

And they ended up giving us the space.

Oh, my God.

Because Julian told me I was going to get fired if I couldn't get three spaces by X date.

And you're probably competing against WeWork for a lot of these leases, right?

Ours were really tiny in the beginning.

So ultimately, we ended up competing with WeWork.

In the beginning we were looking for the 150 square foot really quirky space somewhere in the building where someone could come take a nap or maybe get a little bit of work done.

But The idea was that your phone should be able to unlock all these spaces that are underused throughout the city.

Turns out.

One of the challenges of that thesis is in Manhattan there's really no underused space in the city.

And so we ended up just having to compete with whichever firm wanted to rent that space.

Ended up, I think, kind of figuring out how to make that pitch.

And so that was one side of it.

Once we made it, We had to design and furnish and all these things, these spaces.

And then we had to get people to clean them.

So we worked with one cleaning company that ended up getting acquired by a company that got acquired by Google.

And the day after they got acquired they're like by the way, we don't want to do these terrible five minute jobs that we have to run all over the city for anymore.

You're on your own.

So some of that was me going and literally just cleaning breather spaces.

I would leave dinners with friends and whatever kind of after hours.

The other was because I had met Josh during this process.

I called Josh and was like hey, you have that Uber Rush thing.

Is there any chance that we could get Uber Rush messengers to clean breather spaces, since they're moving around the city anyway?

And so we actually, I was the largest consumer of Uber Rush messengers in the world for a while.

We never had that outside New York.

I

I don't think.

It was super common.

From our banking days, we know, oh, you're always couriering documents around.

Exactly.

And I think part of that is probably what became Uber Eats.

Ultimately, is these people kind of moving around the city on their bikes.

But we had a slider in the Uber app where I would call hopefully there was somebody nearby, I would hit the button, I would drop the pin on the space, hit the button and then have to text with that person and be like hey, by the way, this isn't a delivery job, you're cleaning a space.

And to be fair, these people opted in.

So we had our own viewers, only people who opted in, and they made a little bit more by doing that.

But I'd be like all right, so this particular space.

You go into the room, there's a set of cleaning supplies under the couch.

There's instructions there.

If you have any questions, just text me.

This is my number.

And so seven days a week, 6am to 11pm, pretty much.

When we closed I was just on my phone texting messengers who were going to go clean breathers.

The fun part on the flip side of that was I had equity in the company.

I was our only US employee.

I designed the system myself.

I chose to work with Uber.

And so it's all on me.

And the fun thing about startups is it's all on you.

All the crappy stuff is a product of the way that you designed the system.

And so that was a really fun experience.

And then hired a team, signed a bunch of leases, got promoted a couple of times, ultimately ended up running our operations and real estate and design, which doesn't make any sense, but managed a really talented design team.

And a bunch of stuff that our COO didn't want to do.

I did all of that kind of globally for us.

So incredible experience at Breather, but none of it was particularly easy.

And how big was your team and the company by the time you left?

So in New York my team grew to about 25 people and we were about half the revenue in the company, which was 10 markets.

And then when I got promoted to VP of Experience, which is a fancy title for a bunch of junk jobs not junk jobs, but like not jobs that would normally go together.

It's a catch-all.

It was a catch-all that sounded way fancier than it was, but that was about 150-person team, including our operations associates who were full-time employees of Breather and clean to maintain the spaces, all the way to our team of designers, our customer care team, our real estate team, operations team and all of that.

I'm assembling the cornucopia or the puzzle pieces that would become not boring eventually.

You started pure finance, pure analysis, pure spreadsheet jockey, so disconnected from what actually happens at any of the companies or even in the physical trading of the commodities that you're looking at.

Then, of course, you have one of the most operational jobs one could possibly imagine.

And of course, you have the entrepreneurial moment before that of starting your own company.

Now you have leadership.

So you have that piece of the puzzle too, of understanding like it turns out.

Actually, the hardest thing at any of these companies is the people.

And that was the most amazing thing too.

I probably stayed at Breather for two years longer than I should have because I really loved the team of people that I was working with.

I'd say the last turning point and the last kind of thing that contributed to not boring was we deeply overexpanded our supply because we had been given advice by people on the board and others who said you're pretty much like Uber.

The job for Uber is to get as much supply on the map as humanly possible.

You should also get as much supply on the map as humanly possible.

Which we did.

The catch was there was actually demand for Uber.

There was demand for Uber and Uber supply could come and go and Uber didn't have to pay them anything.

We signed five-year leases and did construction.

And so it was just a very different situation.

So we added a space per day in 2016, 2017 for about a year there.

Every day we were launching a new space.

And so we were deeply oversupplied.

Our gross margins were awful negative, I think negative 25%.

And then me and Ben Rollert, who now runs a company called Composer, which just launched congrats Ben, who was kind of our head of data science at the time, decided to spend a Christmas break just figuring out how we could fix this thing.

And we'd always had this thing where we only did short-term rentals, we only did meetings, whatever.

But we just went deep into the company.

We read a bunch of Ben Thompson, and we read good strategy, bad strategy.

And we're like, we're going to turn this company around using strategy.

And so we wrote this detailed memo full of his data science and my crazy ideas on how we could actually turn the company around by adding monthly space and competing more at the margins with companies like WeWork and Notel.

And then we sent it out to the company.

We got back.

We got the blessing of the exec team.

We sent it out to the company.

Did it have GIFs and Taylor Swift references in it?

I actually don't think it had just intelligence.

We took this very seriously.

You put on your serious business pants for this.

We put on our serious business pants for once.

And the company was really on the line.

It was going to be really hard fundraising or doing anything when we had negative gross margins and too much supply.

And the craziest thing that happened was one everybody bought in and got really excited by this vision, even though it was a ton of work.

We had to flip spaces.

Part of the thesis was...

We have this crazy thing that nobody else has, which is that we can rent spaces out for as little as an hour.

And we have this data science team that can price spaces for as little as an hour.

So if somebody wants to rent a space for one month and then we want to put it back online for hourly bookings in three days, we'll flip it back and forth, depending on what the market is telling us.

Which meant that for the ops team, it was an absolute nightmare.

For the design team, having to design between the two types of spaces...

Absolute nightmare.

But everybody bought in and we turned the thing around and we went from negative 25 margins to positive 25 margins and things were going really, really well.

And so I think Ben and I were both like, wow, strategy actually matters here.

Having a plan and getting people to buy into it, and having something that makes sense and fits within the market all of that.

Actually, it's not just BS.

It's a real meaningful thing.

And so I think that was probably also part of why I ended up writing a newsletter that was about strategy.

Yeah.

To foreshadow, I think at one point early on you described Not Boring as if Bill Simmons and Ben Thompson had a baby.

And so clearly this is where the sort of Ben Thompson side comes from.

A hundred percent.

There's a quote from your first newsletter post, which was not called Not Boring.

It was about this course that you're taking, this writing course.

It says, the first piece I wrote for the course was an introduction to Ben Thompson.

And if you check it out, I would love your feedback.

It was.

The spiritual godfather.

Spiritual Godfather.

The fun thing about that course was I took the course because then we brought in a professional management team and strategy was less valued and my brain was dying.

And so I decided to take a writing course and I wrote about Ben Thompson, because they're like you know what, instead of starting from scratch and I think this actually just showed up in my last piece kind of like go remix other people who you respect, go remix their ideas and kind of just get a sense for what it feels like to write about and to write like the people that you respect.

And so that's how this whole thing kicked off by writing about Ben Thompson.

And so that was David Pearl's rite of passage course, right?

Exactly right.

And you also did on deck at the same time?

I did on deck at the same time after I left Breather.

So it was a little bit later that I did on deck.

But after I finally left Breather, I tried to quit a few times in 2019.

I took a sabbatical, went to Japan.

And while I was there, I called our general counsel and was like, get me out of here, please.

Whoa, you quit from Japan?

The sabbatical was like the last ditch effort to get me to stay.

It was kind of like all right, go take a month off and see if there's any way that you'd want to come back.

And while I was there, I just realized that I did not want to stay there.

And so I quit from Japan by calling our general counsel.

Does that ever work?

It feels like when people get to disconnect and they're already sort of emotionally disconnected all it does is make them more sure that they're ready to be done.

For sure.

I think it's also valuable to give the team.

I had a 150-person team that I think I got along really well with.

And so I think the sabbatical is also useful in being like look Paki's away in Japan right now and the company hasn't fallen apart and your life is not miserable.

So everything will be fine when he leaves.

Yeah, that's a good point.

Okay, so when you did leave, you didn't start Not Boring as we know it today right away.

Am I right that you started two things concurrently with the Not Boring Club, this social in-person experiment, but also a different email newsletter?

I had had per my last email going and that was really like kind of a link roundup, where it was an assignment from the Rite of Passage course to start a newsletter and to get 20 people to sign up.

And so while I was a breather, I was writing that and I realized I like writing and occasionally I would do an essay.

But for the most part it was like here are the five things that I read and listened to this week that I really liked.

And they're all still on the Not Boring Substack.

You can go read them.

But if you go to permylastemailsubstackcom, the day that I took it down, somebody else took the site over.

And I think it's maybe like advertising shampoo or some scam that is now on permylastemailsubstackcom everything turns into a link farm eventually.

Exactly.

So I had that going.

And then I used that to kind of just think through and write about different ideas that I had for a company that I wanted to start.

I mean, even while I was at Bank of America, when I was in college, when I was at Breather, I always knew that I wanted to start what I thought would be a real big startup.

I had just managed a big team.

And I thought I was actually interim CEO for a little while at Breather and thought that I did a fine job there.

And so I was like, oh, I can do this.

Like every level that you go up in a company.

I thought that there were these godlike people above you who had all the answers and realized that they're all as dumb as me.

So why not start something myself?

And so I use writing as a way to think through in public a bunch of these different ideas.

And somehow, despite that tool, the best idea that I came up with was a social club that combined Soho House and college extracurriculars.

So I was a debater in high school and college and One of the tests that I ran was starting a debate club in New York and got 20 friends to come and debate.

And people loved it.

I had a blast.

People really enjoyed it.

And so I was like, that's a really good signal.

This is going to be a huge business because 20 people like debate club.

This is the NYC debate club, right?

Which you can go read about in the per my last email archive.

Yes, you can.

All of this stuff is a blast and I think it all comes from the same spot as the name Not Boring comes from, which is I had dinner with my mom and her business partner one night in New York, while I was still at Breather, and her business partner asked me what I like to do outside of work.

And I just did not have an answer.

Other than I like traveling and I like hanging out with my friends.

I had no passions, which is crazy because in college, that was all I did.

I spent a lot more time doing other things than I did actually probably studying.

And so I think that kind of just put a bug in my head that I wanted to figure out how to get some of that back.

And then I talked to a bunch of other people and they realized that they had kind of the same thing going on, that once you kind of got out of school, it was work.

And then it was your tight group of friends and whoever became your significant other and then your family.

But you didn't have those like kind of small groups that were bonded around a particular kind of passion or hobby.

So I was like, oh, cool.

Like that plus Soho House, that sounds like the coolest thing in the world.

Let me go start that.

And of course, you're coming from a physical real estate company that you just spent six years at.

Well, that was part of the thing too.

I just thought that if I tried to build a software business, I'd have a lot less credibility, even with investors, than if I said look, I know how to do all of this.

I can go, here's the model.

All the numbers work.

I wrote a bunch and you can see these essays too trying to justify how this could be a venture scale thing if you added a bunch of stuff on top and started community first.

And like, Maybe that would have worked.

I don't know.

I mean today, what Not Boring Club would have been, is really a DAO, probably with physical locations.

I think actually that model works really well for what I was trying to do.

At the time, it was a real stretch.

Did you pitch any VCs or investors about investing in Not Boring Club as it was coming together at the end of 2019?

Yeah.

So I had a few early conversations with friendly VCs that I knew from Not Boring.

And some people actually were like, cool, when you actually start raising, let us know.

This is actually pretty interesting.

And we'll back you.

You'll figure it out.

Oh, my God.

If any of these people had actually invested in Not Boring, like, wow.

I know.

I might've shut that one down and started fresh, but it was more of a.

I think we'll back you this idea.

Maybe you can do something with it that gets interesting at some point, but we'll back you.

But I got a bunch of advice from a bunch of other people who were like don't raise money and don't sign a lease.

Please, for the love of God, don't sign a lease before you actually try to build a community.

Because it sounds like the other stuff is hard.

But what's really hard is actually building a community around this kind of stuff.

So I started a Slack group.

I used the newsletter that had 400 people at a time to try to get the early applicants.

Got the community up and running.

We were doing some book clubs.

We did debate club.

There were about 150 of the first people.

And before we had a club to welcome people in, I was like great, we're going to do a bunch of small group dinners starting in February of 2020.

Late February, we had, I think, our first four 10-person group dinners.

They were a lot of fun.

People were really enjoying getting to know each other.

And then I think it was March 10th we had these like separate Slack groups for each one of the dinner groups.

And somebody was like, you know what?

I'm not feeling particularly good.

I'm going to just bow out tonight.

And other people were like, you know what?

I'm going to bow out tonight too, because I'm hearing a lot about this COVID thing.

And so, you know, I was trying to start the boring club in the middle of this COVID thing.

And so you know, we put it on pause.

Canceled that dinner out of an abundance of caution.

Canceled the next night's dinner and the next night's.

And I was like, guys, we'll be back in two weeks here.

Do you remember that?

We're all going to be back in two weeks, right?

We're all going to be back in two weeks.

As soon as this blows over, we'll be back.

I'm going to put a pin in here.

I was trying to figure out listeners how to do the thing that I did during the Uber episode, where I bring in the share price at every moment throughout history.

And I don't have Paki's internal number, so I don't have the newsletter count.

But what I do have is his personal Twitter following as of every month along the way.

So here we are today where Paki has 105,000, 110,000, something like that followers.

Here in February of 2020, taking us back to the story, 956 followers.

And that was good.

That was like a triple from earlier in the year before I started writing per my last email.

And we can talk about this.

One of the things that I wanted to do from like very, very early on.

I would say like welcome to the new X subscribers.

Now there are Y of us here.

Oh, such a good growth hack.

And it wasn't even meant to be a growth hack.

It was really kind of like, just in case this works out and becomes a big thing.

There are all these people with a big Twitter following or a big audience.

Certainly you were in that conversation where I was like there's all these people that seem again kind of godlike.

And it was just preordained that they were going to be successful.

In case this newsletter becomes anything.

I just kind of want to show that I was just a random unemployed idiot who started writing this thing.

And so we can kind of track the whole progression of number of subscribers and all of that throughout the journey.

It's so funny you had that impression of us because I had like zero credibility before starting Acquired.

I mean, I felt exactly like you did.

Like I had these startup experiences and I've worked at this.

Well, to be fair, there was a front page Seattle Times article about you before you started Acquired.

One day, one moment in time.

Yeah.

But Paki, I know that exact feeling.

And it's so funny how at some point and there's no clear moment in time when it changes, but at some point then people look at you like you're on the other side of that valley.

And you're like, wait, how did I get to the other side?

What?

It's crazy and, like you know, i try to be the same idiot that i was then.

It is, as you know, like i'd still tweet dumb stuff and maybe that's good, maybe like the sec is going to knock down my door at some point, but i'm like really trying to just be the same person that i've been the whole time.

Not in any, like you know, fame hasn't changed me, but really just like i don't want to care that, like I'm going to get responses from a bunch of trolls now if I say something.

I really think this breaks when I let that change me and I like get a little bit safer in what I write about, because or what I tweet about, or anything, because there are more trolls out there, more people who are paying attention to what I'm writing, and all of that.

And so that's been important to me the whole time is kind of remaining the same idiot that I was in the beginning.

Think it's super important.

This is the not boring episode, not the acquired episode, but i've had a few conversations recently with people who have grown a personal brand very quickly online and i think a lot of people make a lot of trade-offs to do that, where they play a part on the internet and play a character rather than being themselves and you sort of have this magical thing.

At least my perception, knowing you personally and following your work, is that they're pretty much the same person, But you've managed to grow very quickly by being yourself, which is remarkable.

Because I think in three conversations that I can think of recently, people have told me like I really wish I could be more myself, but I played a character on the internet so that I could quickly grow.

It's easy to make that trade-off.

And I probably did a little bit of that frankly, early on, where I would do more threads and different things to try to boost engagement and all of that.

But still, it was so small that nobody was paying attention.

By the time that I had anybody following, I've just decided to be myself because...

I'm spending so much time doing this both writing and tweeting and meeting people and all of that that if you're not yourself, it's not like a be true to yourself kind of thing.

It's like you're going to have a miserable experience because all of your interactions are going to be other people wanting to interact with this persona, or if I were writing from a different voice, everyone would expect me to write from that.

And it would just make it twice as hard to both figure out the content and the voice every week.

And so I realized really early on that I just needed to kind of be as close to myself as humanly possible or else it was just going to be too much work.

And once you admit that, you're kind of like, okay, well, if it works, it works.

And if I don't have product market fit with some sub-segment of the internet who can discover me?

Then shoot, I'll take my ball and go home.

But if it works, it's actually remarkably scalable for a one-person operation.

Exactly.

So we can debate when you cross this valley, but certainly at this point in time, you have not.

What are you feeling now in March 2020?

You're unemployed again, but you're older.

You're married.

Your wife is pregnant at this point, right?

Correct.

You are working on a I won't say harebrained, but maybe a startup idea in a physical real estate space, with maybe some issues with the business model.

Not particularly venture-backable business.

Not particularly venture-backable.

What are your emotions like right now?

Are you just, I'm happy-go-lucky, it's all going to work out?

Or are you like kind of tearing your hair out?

I'm to a fault and everybody has their double-edged sword and mine is optimism.

Never once was there a time when I was like, my life is absolutely over.

When I joined Breather and took a lower salary and it was a risky thing my mindset was like my absolute worst case scenario here is that I moved back to my parents' house and I can still eat meals and I can still sleep in a bed and there's a roof over my head.

So like, The floor is not that low.

Certainly this time around there's 100 ego piece of this, because I have a bunch of friends who are doing really, really great things.

And I was, you know, when I tried to bring Not Boring Club online.

I was sitting there.

I had trivia nights that I like, spent all day writing trivia questions and making slides, and seven people showed up.

And I was like this is with my Duke education, my expensive high school education.

All my experience like this is incredibly embarrassing.

And so I decided to kind of just let Not Boring Club, the digital version, fall by the wayside.

In February, early February, Pooja and I learned that we were pregnant.

COVID kind of hit.

And I remember this was probably April when I decided to really go all in.

It was a bunch of soul-searching conversations with Pooja, with my mom talking to my mom and being like I don't know what to do here.

And she's like, well, I like the name Not Boring Club.

Maybe you should just apply that to the newsletter and just go all in on the not boring thing.

So that was my mom's idea to port the name over.

Nice.

Wow.

Thanks, mom.

We should all thank our mothers more.

Thank you, mom.

Totally.

Thank you, mom.

And even my dad, who's always been kind of like don't close off doors and just serious about me making sure that I did the best that I possibly could, was super supportive of this whole thing.

Maybe just because they saw that there was nothing else on the table.

To be fair, I could have gotten a job somewhere, but I just didn't want to get a job yet.

I

So I went to the beach with my brother for a week and was just like, all right, what if I just start writing this newsletter?

And what if I start writing essays?

And it needs to be different than Ben Thompson.

So I came up with this idea to do kind of a mix between business strategy and pop culture.

And so my earliest essays were, like creative destruction and the Mickey Mouse Club, to explain why COVID was actually a really good thing, because it meant that people were no longer going to be stuck in bullshit jobs and were going to be freed up to go do the things that they actually wanted to do.

Which is ironically also the subject of your most recent piece.

A little bit.

It's a different twist on it, for sure.

It's more about the sort of community and societal impacts of that, but of the same impetus.

Totally.

There are definitely some through lines through a lot of the pieces.

I wrote about.

Amazon had a fashion show and I tried to examine Amazon's strategy through the lens of this fashion show and did a bunch of those direct pop culture, ex-business strategy type essays.

That also like pretending to be a character became too much, where I'd have to both think of like the business side of it and then also figure out what movie that business was like.

And that became too much.

So I kept the tone and I dropped that direct thing.

But yeah, I mean it, just like I asked Pooja if I could have three months to grow the newsletter and see if there was anything there.

And like maybe one day I'd start making money.

But for now, let me just see if I can grow this.

A friend of mine, Tommy Gamba, who was at Airbnb and getting ready to leave, helped me out on the growth side of things and had this brilliant idea to launch a landing page so that we could launch on Product Hunt.

And that alone, I think, took us from something very small like 1000 subscribers to 2000 subscribers.

So that was a huge leap.

And I remember sitting with Pooja at dinner and being like, oh my God, I could actually like this newsletter could be a full-time thing.

I have 2,000 subscribers.

This is a Amazing.

Seven people at trivia night.

Now you have 2000 people on the internet.

Maybe this internet thing is a good idea.

We like to say we're talking orders of magnitude difference here.

That's a VC term.

So yeah.

So I mean things like kind of started looking up from that point and wasn't making any revenue for uh, a long time.

And I still remember having conversations deeper into the pregnancy where it was clearly going to be a thing.

And I had planned to turn on subscriptions and decided to keep holding off on that because I really liked the growth.

And I had conversations with Pooja where she was like, are we going to do a revenue thing here?

And mind you, now we're living at my in-law's house in New Jersey during COVID.

And I was writing... With her parents.

With her parents.

And I was writing from a basement.

So none of this is glamorous.

But she's like, at some point, we'll need health insurance and blah, blah, blah.

You're going to turn on revenue?

And I was like, no, no, trust me.

If we can keep not having subscriptions turned on for a while, then we can grow to a point where I'll be able to turn on subscriptions.

And if I convert 10 of the audience at 5 a month, then we could be making a couple thousand dollars a month.

Subscriptions work as a business model.

If you architect the right way, there's nothing wrong with it, and obviously our friend mario gabrielli is doing great with it.

The generalist, but oh, that's such a fallacy, that way of thinking of oh, if i only get x percent to convert oh, i'm so glad you went a different direction.

There's also the dirty secret which it seems like you kind of intrinsically knew, which is even 10 is going to be a pretty big stretch.

Creators can typically convert at best 2 to 3 to a paid offering, unless they're significantly handicapping the main content where you'd say like sorry, every other main post is behind the paywall, or something big like that.

But even then, I think it's like 10%, 15% if you bring out your big stick.

And that prevents growth.

And so it's hard to model out exactly how that's going to play out.

But my big thing was, I was just addicted because I locked myself into this thing where I was telling people how many I grew every week.

I was kind of addicted to that number continuing to go up.

And so I just kept pushing off, kind of turning on subscriptions, so that that number would keep going up.

And then Mario did it well.

Lenny Richesky obviously did it really well and has a great business.

So there are ways to do it.

I think a huge difference between like someone like Lenny and someone like me is that And Lenny's audience is so specific and, like you, know exactly who you are and who should be paying for that, which is people who do product or people who do growth.

And not only do they know that they should be reading that and that they need to pay for it, their companies are going to be willing to pay for it for them.

Whereas I could not imagine a company that'd be willing to pay so somebody could read about the Mickey Mouse Club.

And so that was the other kind of thing that kept me from going to.

The subscription model is like I just don't know if companies will be able to pay for not boring.

Yeah.

That was the secret when I was at the Wall Street Journal.

And this was in the days of paid content was such a thing.

And everybody thought, oh, the Wall Street Journal, they did it so right.

The New York Times was wrong.

It was like, yeah, this is the dirty secret.

Most people who pay for the journal, it's their companies that are paying for the journal.

And it's hyper-specific.

It's business, finance.

It's the most reputable of that.

Yeah.

If you're going to go the paid subscription route, it's great, but you need to architect your whole business and content strategy around that.

And obviously you had taken a different path.

Packy is just going to be packy on the internet.

Yeah.

So I was too lazy to do the subscription thing too and think about which should go behind the paywall and which shouldn't.

And could I possibly double the amount of content that I was doing so that I could still grow and have some things behind the paywall and keep the quality?

And so I just frankly couldn't figure all of that out.

And so that was one of the reasons that I decided not to go that route too.

Okay.

So what month was your baby born?

Our baby was born on October 4th.

I remember I had my laptop in the hospital.

He was supposed to be born a day later.

And so I was going to be able to finish a piece I was writing about reliance.

And so I was almost done that piece, sitting in the hospital while we were waiting for him to be born.

And I just couldn't get it finished.

So he was born, Devin, who is the absolute best.

Shout out to Dev if you're listening to this in the future.

Okay.

Well, I asked for our tracker here.

So you were talking about later into the pregnancy when Pooja was asking you like hey, are we going to do this revenue thing?

I'm going to assume somewhere end of the second trimester, beginning of the third trimester, you're at 3500 Twitter followers when you get that question.

Then we fast forward to, you know, Devin is born, this big moment in your life.

You're already up to 12,000 Twitter followers.

So you're starting to feel like geez?

I'm assuming that this maps similarly to newsletter subscribers.

You're kind of looking at this like...

Well, if it's going to keep growing like this, and it's actually going to grow geometrically, not linearly, we could be in good shape pretty soon.

But I imagine you're probably also pinching yourself and going, this can't continue, right?

In the summer, kind of late summer, somebody was nice enough to reach out.

Chris at MarketerHire was nice enough to reach out and be like, hey, I like your newsletter.

Are you thinking about taking advertisers?

And I was like, yeah, I'd love to have you advertise.

And he's like, great, send me your deck.

And I didn't have a deck.

And so I surveyed the audience and I asked them for their characteristics, and they all came back exactly like you'd want 25 to 34 high-income households, leadership positions at companies, well-educated.

Owning big budgets, decision makers.

Exactly.

This deck is amazing, by the way.

It's still on the internet.

We'll link to it in the show notes.

It's still on the internet which haunts me actually, because people reach out and they're like great, I'd love to do a sponsorship at 1000 or whatever price I put in the deck at that point.

But after I made that deck, I was like, you know what?

This internet thing has been pretty amazing and Twitter has been pretty great.

I'm just going to tweet the deck out.

And so that filled up and public came in, market hire came in.

A few other sponsors came in from that.

But that filled up pretty much through the end of 2020 all of my sponsorship slots, which was great.

And I was like, oh, wow.

So then I remember having a conversation with push orders like, I don't know.

Things go really well.

I think maybe there's a chance that in the future we could do 300000 or 400000 on this newsletter on sponsorships.

You're an optimist.

Optimist.

And I kept relying on the math.

I had some sophisticated formula here.

I was like, it's purely math.

It's just a CPM thing.

And so, as long as we have enough readers, the rates will grow, and this will be something that at least I can make what I was making when I was a 24-year-old in investment banking again.

Yeah.

So before Chris at marketer hire reached out to you about sponsorship, had you been thinking about advertising or were you totally focused on one day, when we get to a certain point, we're going to flip to subscription?

No, I mean, I think the other thing about me is I have an addictive personality.

And so you know, I think we had probably crossed a point where I just realized that I liked the growth too much.

And I realized that I liked the fact that you know if I was going to be spending all of this time, like you know 40, 50 hours to read an essay.

I didn't want a thousand people to read that essay.

And I wanted people tweeting about it and talking about it and all of that.

And so at some point I realized it was probably going to go ads.

I just like hadn't made the leap because I thought even ads would slow growth and the people wouldn't like me doing ads.

And so I was trying to hold off on that for a little while too.

But yeah, a few companies kind of pushed me in that direction and proved that I could actually make a dollar doing that, which is great.

There was another moment where I wasn't allowed to buy an iPad until I actually made money from not borrowing.

And so finally, I made like $10,000 and Pooja let me buy an iPad.

So like a bunch of little wins late 2020.

Yeah.

How proud were you at that moment?

It's quaint now looking back on it, but like these are the things along the way that I'm sure you remember.

Totally.

And it is a glorified Kindle for me.

I read books on it and occasionally I'll draw something and throw in the essay, like this last week's title image.

I actually drew myself.

It's horrendous.

I was like, you know, I'm going to be Ben Thompson is all I need is an iPad.

Like, can I please like dip into savings here and get an iPad?

And she's like, no, you don't make any money on this newsletter.

Like you cannot buy yourself an iPad that you don't need.

You have a computer.

You're fine.

Okay, so two questions for you.

One, did you experience the thing where the period of time where hey, this isn't going to cover our lifestyle is long?

And then hey, the period of time where whoa, this is going to more than cover our lifestyle is long.

But the period of, hey, this is great.

We're like right at break even sustainable is like remarkably short.

So you sort of like blow by it.

And then you're like, whoa, holy crap.

I expected that to be like a longer period of the journey.

100%.

Yeah, that happened really quickly.

And again, to be fair, covering our lifestyle was not particularly difficult when we were living in my in-law's basement.

We had a baby, and so that was a real meaningful thing.

But when you have a baby David, you know this people send you probably the first, at least six months worth of clothes and diapers and all of that kind of stuff.

So you don't really start incurring expenses on the kid for a bunch of months.

And we were living in a basement, and my mother-in-law is a phenomenal cook.

And so like, I was maybe paying for a Wawa hoagie every once in a while.

Yes, Wawa hoagies.

Yes.

It's the best.

You guys need to do an Acquired on Wawa at some point.

Oh, we totally should.

Wait, so okay, let me get to question number two then.

I mean it's great to be in phase three, but it's like weirdly unsatisfying how fast you blow through phase two because you've been looking forward to it for so long.

I guess it's the optimist thing again.

Because I set the first three months up as an experiment and knew that I could go find another job somewhere and that hopefully, maybe the newsletter would have introduced me to somebody who might be willing to hire me because they liked what I wrote.

So that wasn't like a revenue desirous period.

And then there were those months in between, kind of after that, where it was growing.

And I was like, this is going to happen.

So probably everybody around me was relieved that it happened.

But for me, it was kind of like, no, no, no.

Again, it's math here.

And so this will happen.

And as long as it keeps growing, then it'll become a number that is really exciting.

I didn't think it was going to go as well as it did.

But...

There was no point where I was like I really hope that I'm able to eat and that I can scrape things together.

Again, probably because we were living in my in-laws' basement.

But I think that probably would have made it a little more satisfying if I was every month dreading the rent check.

But fortunately, that was not an issue for us.

Yeah.

Okay.

So then that leads me to question number two, which is you have pioneered a pretty unique sponsorship format.

We thought we pioneered a unique sponsorship format in the presenting sponsorship, where we really throw our lot in with the presenting sponsor for three months.

Shout out to Pilot, Albemarle, website, everything.

Interview on the top of the show.

And then here comes Paki McCormick and says, you know what?

Every week...

One of the two posts that I do is going to be pure unadulterated.

I'm getting paid by the subject to write this.

I am doing the thing that is going to make classically trained journalists freak out.

And I'm just going to own that.

How did you come to this?

And what were your fears around it?

How did it come to be?

All that.

So I'm going to get the origin story somewhat wrong.

I'd started talking to Nick Abizit at Main Street.

And if you use Twitter, you've probably gotten a sponsored tweet from him about using Main Street.

Also happens to be a phenomenal guy.

Love, Nick.

Thank you.

And he was like by the way, these posts that you write on companies, you can write those on startups.

And I bet people would be willing to pay.

And he had just come over from Shrug Capital to run marketing at Main Street.

And he's like, we'll be the first ones who do this.

And I was like, all right, cool.

Let's try it.

I'm going to caveat the hell out of it and tell everybody right up front that it's sponsored.

But I think Main Street is really cool.

So I would actually love to write about Main Street and explain.

And my audience is a bunch of entrepreneurs and founders.

And I bet my entrepreneur and founder audience would love to make money back from the government that otherwise they might not have.

And Main Street will get you kind of your tax credits back in an easy way.

By the way, what month was this that you're having this conversation-ish?

Yeah.

This was actually pretty early in the sponsorship journey.

So this was probably also in like the August, September range.

Okay.

So still at 10,000-ish Twitter followers?

Still at 10,000-ish Twitter followers.

My fears were obviously like, this is not what you're supposed to do.

You're not supposed to use a newsletter to shill.

Sponsored content is a sturdy word because at a normal journalistic institution that has integrity, there's a wall between the people who write the actual journalists and the people who write sponsored content.

And it's this thing that is optimized for SEO and clickbaity and all that kind of stuff.

Sponsored content does not have a particularly great name, but I was like all right, so if I do this, really my bar for myself has to be as high as it would be writing a normal piece, and i'm only going to write about things that i'm actually bullish on and companies that i would actually invest in myself.

And this is before there was a fund or anything.

But you know that i'd put my personal money into, and so that was kind of the bar that i set for myself, and i was like you know what i'm gonna like.

Ask the audience even like did you hate this?

Please let me know if you hated this.

You know one or two people every time i write a sponsored post, is like you're shilling.

This is sponsored.

No sponsored content, please.

But the vast majority either don't care although the open rates are actually fairly consistent, maybe a little bit higher on the Monday pieces or they get something out of it.

So Main Street, a bunch of people went and got a bunch of money back.

So they love that.

It's interesting because I serve a bunch of different audiences.

When I talk to founders for Not Boring Capital now, a lot of their favorite pieces actually end up being some of the sponsored posts, because I get behind the scenes access into some of these really fast-growing, successful startups and get to write something more detailed on them than anybody else has written before.

Oh, yeah.

I am an investor in Modern Treasury and I learned a lot about the company from your recent sponsored post on Modern Treasury.

There's somebody who writes a newsletter, who does this thing, where the startups actually pay him to write about them.

But it's actually kind of good because he gets more information for these companies that aren't publicly available.

He was kind of saying that he doesn't write about private companies as much because he doesn't have as much material to analyze.

But that if I actually work with the company, I have a bunch of stuff to analyze.

And I'm very honest with them that I will talk about what I think isn't great if there are things.

And I will talk about competitors in a positive light.

And I will never say, just like you know, do a hatchet job on competitors in the piece, unless competitors like a straw man.

Like you know, I talked a lot of shit on passwords when I wrote about Stitch, and that's fine, because nobody loves passwords.

But as long as I keep that bar high and I'm very honest, I say upfront every time this is a sponsored post.

This is how it works.

Here's a link to a doc that I wrote about how I choose them.

People end up liking the posts.

And so what I was saying was founders end up liking those, because oftentimes they're either at the same spot in their journey or they're a little bit behind where those companies are.

And so they're learning practical on the ground things that those companies are doing and can take lessons from that.

So those actually feed in a lot of different ways really well into the fund.

I want to pause for a second in the action movie story of the not boring story.

I think this is a good point to talk about a few things kind of just going on in the world around you doing this.

And one.

Obviously, what you're doing wouldn't be possible without all the platforms and infrastructure Substack Twitter, all of the things that we take for granted now but 10 years ago didn't exist.

It just wouldn't be possible to have a... solo corporation, like not boring to be doing.

Even when Ben Thompson did it, he had to roll his own for so much of this.

You are operating a venture fund with no other employees.

AngelList makes that possible.

But it's interesting, right?

Like you said, a traditional media organization would have journalistic integrity and would never do this right.

Yeah.

Well, what is journalistic integrity, right?

And, like you know, post 2016 and Donald Trump and everything, like you know, this is kind of one of those second, third order effects of the last five years in the world, in this country of like well, maybe mainstream journalism still has a great place, but maybe it's okay to also do things differently.

And maybe they don't have all the truth.

And maybe...

Maybe you can think differently about what journalistic integrity means.

And then you kind of looked at this like ghetto of sponsored content and it truly was a ghetto.

Was it a ghetto because it didn't have integrity or because nobody put the work in to make it great?

You know, you made it great.

Yeah, there's a lot to impact.

So first of all, the platforms.

Like you know, I'm all in on Web3 now certainly rely on Web2 platforms in a really big way.

The most beautiful part about Substack is because they've taken such a strong stand for subscriptions and against advertising.

No one on their team has ever even reached out to me.

And so I paid $0 for my main platform because they want to pretend like ads don't exist.

And I hope they don't hear this and start charging.

They've never reached out to you?

Never reached out.

Oh my God.

Yeah.

So that is just like kind of this happy accident where my main platform ends up being free.

And so people will pitch me kind of new newsletter platforms all the time.

And they're like bet, you're pretty bummed that you're paying 10 of your revenue to Substack right.

And I'm like, I actually haven't paid anything to Substack.

Yeah.

Twitter is free and I've written about this before, but actually I pay for Twitter Blue now, just out of a thank you.

It's a garbage product so far, but just as out of a thank you for all that Twitter has done, I pay 299 a month for that now.

So that's a cost.

But these platforms have been hugely helpful in making that boring what it is and are low cost.

On the other side.

The point you're talking about journalistic integrity were catching me at a time where I'm like kind of in this mini self-proclaimed nobody cares, but like kind of war against all the cynicism that's happening out there.

I think everybody has incentives and motives.

And at least if I'm saying I am sponsored and this company is paying me right now to write about this.

It is just very out in the open what I'm trying to do.

Or if I say I invested in this company or whatever else, like everybody can go into the piece, kind of knowing that that is the table stakes.

I don't know what the incentives are for traditional tech journalists and they're not certainly all this bad, but And I think a lot of the reason that not boring works is because there's so much snark about tech out there for all of these companies that are one just groups of people not making a ton of money.

And like now maybe salaries are a little bit better and all of that.

But for the past decade people at these small companies not making a ton of money and like actually trying to change the world.

And that's like a corny phrase, but like that is how you can recruit people to come work somewhere and not make a lot of money trying these new things, like taking different pieces off the shelf, going and trying to build something.

And then there's like snarky 50 year old men sitting back and being like oh no, I've seen something like this before.

This is really stupid, or X, Y and Z, And this is not well thought out enough even for me to be saying this publicly, but it feels like a lot of journalism is left over from an era where journalism was really needed because not everything was out in the open and you needed journalism to expose corruption and take down Tammany Hall and all this stuff.

And then you apply all of that to these little tech companies that have raised $5 million.

And you try to dig through the garbage.

There was an article in Business Insider on Spring Health about their work culture the other day.

That was trying to be a hatchet job, but there was nothing bad in there.

People worked hard at the company.

A marketing guy said his team was working too hard, and so he wanted to lower the goals.

And the CEO said, no, we're not lowering the goals, but I'll hire more people for you.

That is a tale as old as time in startups that there's a battle between the CEO and the marketing team about what the goal should be.

And the CEO sets an overly aggressive goal.

And the fact that somebody think it's worth investigating for four months this story about this company or the hit job that they just did on Rowe, which was also total BS.

You can always find someone who's unhappy in a company when you're not making that much money and when you're working a lot.

And then to use these people who have gotten fired as sources for these hit pieces that are poorly done and nobody believes that is just abysmal.

I think when the market turns and when we enter a bit of a bear market in tech and Web3, it will be really easy to throw stones at me.

I am unabashedly optimistic about all of this and things are going to turn.

The tide's going to go out and my pants are going to be down.

I'm also totally fine with that, because I do think that the overall tone of tech journalism is like what's wrong with these companies?

They're making too much money.

And so if somebody has to be on the other side saying like, no, this is awesome.

I'm happy to be that guy.

It's exactly what you said.

It's incentives and it's audiences.

You planted your flag from the very beginning that you are going to be an optimist and your audience is founders and people who are also optimists about this whole industry.

There's a viable audience of people who are pessimists out there and who don't like it.

And that's what the other media outlets can write for and to.

But it's like nobody was doing what you're doing.

The other piece of it too, is like you know.

I want to be optimistic because that's like naturally what I am.

It goes back to doing the thing that you actually are.

And there's a reason I worked at a startup.

And even though that startup didn't do well, I'm still optimistic about this because I think like a lot of really great stuff has come out of this.

I also want to be realistic.

So I'm not going to just be like, this is always the greatest thing in the whole entire world.

My favorite kind of audience are the people who come in and they're like.

I was frankly really skeptical about crypto or about Web3 or about tech in general, until I read this piece and it explained it really well in ways that make sense.

So I still try to tie this stuff back to like, business principles.

I mean, we're both huge Seven Powers fans.

So I'll try to actually tie back to what is the competitive advantage of this protocol or of this company.

And so I don't want it to just be like pie in the sky optimism.

So if I can convert people who were either pessimistic or skeptical over to at least being thoughtful about it, that's all I'm going for is be thoughtful about it.

And I think if you're thoughtful about this industry, you're going to come away at least being like wow, they've done a lot in the past few decades.

Well, and you seem to operate under the same primary principle that we do.

And David and I text ourselves this phrase all the time, or text each other this phrase when one of us is straying from it.

But rule number one at Acquired is assume the audience is smart.

And if you assume that the cool thing is long-term, it means you'll get a whole bunch of smart people.

As long as you keep doing your thing and you stay true to that, that'll pay attention.

It comes with these interesting trade-offs where you can never allow yourself to hide the ball, or else you're compromising that long-term goal.

And so you always to the extent that you are assuming your audience is smart you have to write well-reasoned stuff or else you are just going to take an enormous amount of shit for what you put out in the world.

It's not like you can say, hey, here are my incentives.

This thing is sponsored.

And then write a total fluff thing with zero serious analysis in there, because everyone's just going to look at it and go well yeah, you told me that your independence was compromised and then it wasn't useful.

Then it wasn't something that I enjoyed thinking about.

You can't waste people's time, certainly.

One of the tests that I always run for myself and I probably actually would have failed this test is if Theranos had come to me on a sponsored post, however many years ago, chances are frankly, I would have written something positive on Theranos, because I assume the best and I'm not technical.

And so I'm not digging into that machine and being like actually, do you know that the science doesn't make any sense?

That seems impossible.

With that small of a blood sample, how could you possibly...

And that's where investigative journalism has a very valid role.

100%.

There are goods to both and there are bad things to my approach.

And I don't know which company probably none of them, but maybe there's a company that I've written about that ends up being a total house of cards in five years.

And I look like an idiot for writing that piece.

I probably would have written it about Theranos.

And that's an okay trade as long as I'm like...

Nobody's expecting me to analyze the science behind Theranos.

If I could analyze the business side of the business at least and do the work, and maybe somebody learned something that is not just about Theranos but about some other concept that I'm using to analyze the company, then that's okay.

So I guess that's the risk.

Well, that gets back to this, frankly...

I don't know if it was intentional or not, but this brilliant sort of jujitsu you did with sponsored content that was a ghetto and sucked because nobody actually gave a damn, put any effort in to make it great.

You've done that, but you do have to put the effort in to make it great.

A hundred percent.

Yeah.

The worst thing that could possibly happen is if I did one of those and wasted people's time because people would unsubscribe.

People wouldn't read the next sponsored post.

So the whole thing falls apart.

If I lose my integrity throughout this process.

The lucky thing is that I've been a pretty like open optimist the whole time.

So no one's like, that's so weird.

You rip apart tech on Monday.

And then on Thursday when people pay you, you're like really generous to this whole industry.

So it's all consistent at least.

So I told you at the beginning this wasn't going to be all softballs.

I don't want to pretend that every Thursday piece is exactly as interesting as every Monday piece.

And again, I think this is okay.

But there are a lot of Thursday pieces that the headline doesn't sound interesting to me.

And I end up either not reading it or just skimming it to make sure I didn't miss some huge piece of information where I'm like it would be good for me to know this.

However, when the Monday pieces come out, I'm like, ooh, this could be the next great online game.

This could be the next cooperation economy.

And it's rare that I think that a Thursday piece is going to be that.

Actually, except for like Solana Summer, that kind of was that.

But I do think that that's probably in line with your sponsors' expectations is that it's going to appeal to a group of people that they particularly want to appeal to, who wants to know about their company and happens to be a subset of your audience.

But it's probably not going to be like hey, let's all close our eyes and pray and do kumbaya that this is exactly the same thing as the non-sponsored content.

That's totally fair.

I try to make it as good as I possibly can.

I'm often writing though, about either a specific company which is just like a smaller design space than something like a great online game would be.

And I'm also writing, I guess, about a company that has less of a history and less complexity to it maybe, than some of the larger public companies that I write about.

So my goal is to write the best thing that's been written on that company every time I do a sponsored deep dive.

And chances are, in a lot of cases, it's a two-year-old company.

The best thing that's ever been written on that company isn't going to be as interesting as breaking down Tencent over 20000 words, because Tencent is a sprawling business that has this crazy innovative business model.

And so, while I want it to be as close to the Monday as humanly possible, my real bar for myself is can this be the best thing that's ever been written on this particular company?

Plus, is this a company that I would invest in and all of that?

And so if the open rate is...

37% instead of 45% on Thursdays, I'm totally fine with that.

And everybody's come away very happy from the sponsored deep dives on the company side.

Yeah.

To my mind, the right question to ask isn't necessarily.

Is every Thursday piece going to be as good as every Monday piece?

It's if I'm the company, if I'm your customer...

Is this blatantly obviously the very best thing that I can do to get something written and a great deep analysis done about my company.

And that is so obviously yes.

What are their alternatives?

I'm sure there'll be more people like you who pop up and that's great.

It's not a zero-sum game.

But if I'm a two-year-old company and I'm the founders of that company and I want to, I think I've got something great.

But I need to cross the chasm to have people know about it.

It's not like you're going to write a Monday piece about it otherwise, necessarily.

The other fun thing too is companies can almost choose how interesting they want it to be.

And they're kind of double unicorn round when they raised at a 11 billion valuation and a 16 billion valuation in the same transaction.

And the reason that that one worked so well was because Eric the CEO there was like dude, completely open kimono.

Ask us anything.

I will give you the timeline of how this round game came together.

I will give you exactly how we think about cap table construction.

You tell me what you need to make this the most interesting piece possible.

And I will give that to you.

And a lot of companies make the trade on the other side, which is also totally fair.

They want to keep some information private that they think there's an advantage to keeping private.

And so that's the trade that I think you make there.

But there's a reason.

I think people refer to that piece often when they're reaching out to me about sponsored posts.

And then a lot of companies aren't willing to make that trade off when I'm like cool, the reason that one worked so well is because they told me everything.

And they're like, cool, do that, but maybe 90% of the information.

Before we move on, I want to cover one final topic of journalistic integrity because David, I think, like your take may come across, when we go back and listen to this, as a little bit too like, and this is when the downfall of democracy started.

We can point to this moment where David Rosenthal said that journalistic integrity is not important.

I don't mean it that way.

Hey, I don't think that's like really the right takeaway, but it could be heard that way.

I think there's like two pieces, when you really unpack it, of like why is journalistic integrity important?

The first one is that the reader is fully disclosed on the incentives and knows what they're getting.

And we've covered that topic.

Like Paki, you wave your arms around all over the place and everyone knows what they signed up for.

So that's almost like the microeconomic or like the micro to your business.

Uh, I could do that.

And you have the very best writers from the New York Times or Forbes or the Wall Street Journal that are just like I could go, make five to 10 times as much and have a much more independent lifestyle with control over my life.

Okay, by opening this up, this independent journalism, quote unquote journalism I think it's important to not call it journalism.

Independent content creation that is entertaining to read and fully disclosed, incentivized.

Do we chisel away at the third estate?

So one of the things that I think has been really interesting is that people have jumped over the fence from working for a publication to going independent and then now have started to jump back.

And I couldn't do what they do.

And this is not a lack of respect for those people.

My brain wouldn't work.

If someone hired me to be like, you have to go be an investigative journalist.

It wouldn't work.

Right.

And so that's one part.

I do have respect for that, particularly where it's applied the right way.

My problem is when it's applied to like a one year old startup that maybe like, overworks their quote unquote overworks their employees a little bit, as startups occasionally do and as a lot of companies occasionally do.

When you apply the same rigor to that as Watergate, that's when I have a bit of an issue with it.

So going back to the piece on people jumping over and back, there's a lot that goes into that.

And I think it's really hard to do that kind of journalism independently because you need lawyers who have your back.

And you need editors to make sure that you get everything right.

And you need all this stuff to protect you when you're doing this really brave work that I think is tougher to do on the independent side.

So I 100% think that there's a place for that kind of journalism.

It's just like don't apply that to a startup that makes hot dogs and came in over budget one quarter, and that shows how stupid startups are.

That kind of article is what really gets me.

Well, I think it also works the other way too, which is that it's hard to do what you're doing.

The goal of this episode has been to tell your story.

And I think one of the takeaways that I'm not surprised by is like your whole life and career led to this.

So if you were an investigative journalist at XYZ Publication, doing very much not this.

And then you're like, oh, I'm just going to jump over and do what Paki does.

You wouldn't be equipped in the same way that you are.

You worked for six years at a startup from employee six through hundreds of people.

And through failure, which helps.

Through failure.

Yeah, exactly.

I think that's right.

There's definitely an empathy there too.

And I go into this knowing full well that it's wild that I was an employee not a founder at a startup that sold for 3 million after raising 120 million.

So like, unless the content stands for itself, nobody should be listening to me, because there are many more successful people to listen to out there.

So all of that has let in and, I think, gives me a great empathy for what founders are doing.

But the content has to stand for itself.

Okay.

So, taking us back to the story you mentioned, February is when Ben Thompson mentioned you as some guy who writes a newsletter whose name I can't remember, or something like that.

And of course, The funny thing about compounding you went from zero.

Ben Thompson mentions your whole life to like.

Now it feels like every few newsletters I read from him I'm like oh, there's Packy again.

But that first no name name mention, I think was in February when you had 22,000 Twitter followers.

You also sent out a tweet in February that you wanted Not Boring to make 1 million this year which, as David has in the notes, sounds effing crazy.

And I'm curious, what happened in your brain as you formulated that tweet?

Was it that the sponsored posts had been going well?

Were you already contemplating not boring capital?

What was that moment like?

Yeah.

So I'd been thinking a little bit about Not Boring Capital.

And so that was there, but really was talking about just purely making a million dollars off of the newsletter.

A couple of things that happened around that time.

Like me, and Ben from Composer wrote this piece on Excel that got picked up, I think, by two separate New York Times articles and got to the top of Hacker News and all of that kind of stuff.

So I was like, whoa, that was my first taste of like this thing really going kind of mainstream.

I had written a sponsored post.

I think probably you know, either that week or was in the middle of writing the post and the company was really happy with it.

And I was in Miami and the weather was nice and I could have been in New York in the middle of February and I probably wouldn't have tweeted the same thing.

But I woke up and the sun was shining and I was like you know what.

Life is pretty good.

I'm probably making at this point, call it $10,000 or $15,000 a month or something like that.

So not close, maybe $20,000.

I don't know.

But I just woke up feeling really good.

And I was like, I'm just going to say this.

People will probably think I'm an asshole, but I've struggled on 0 for the past X number of months and I'm just going to say it.

And then As I think happens often with those tweets, like the support was actually huge from them.

Like nobody reads that as a cocky signal because first I didn't say like, guess what I just did.

It was more like I hope that would be wild if this happens.

But also people like want to see other people take risks and succeed at them, I think.

It's like if Packy's making it, maybe I'm kind of making it in a way.

The other thing is, I guess there is like a tiny buffer between just like me saying like I'm going to make a million dollar salary this year and saying like not boring, we'll make a million dollars because it's still a business.

And for a business, a million dollars a year is like fine.

You could probably raise a seed and maybe a series A in this market on that.

And certainly not in a media company.

So you know it's not like anything crazy from a business perspective, but you know that was.

That was where that came from.

All right, so give us the update.

We're now in, it'll be December by the time this comes out.

How are we trending?

I think Wagmeat.

We're talking about Pilot, and I certainly probably need the help of bookkeepers.

I just pulled my Mercury account that I do all of my banking in and I think that probably has about 750000 in revenue.

There's a bunch of invoices outstanding.

Some people send checks.

Some goes to my personal banking.

This is not a well-run business by any stretch of the imagination.

And I have a few pieces kind of coming up.

And so I think chances are we're going to just kind of cross a million dollars in 2021.

Wow.

So great.

What would you have put the percentage chance at when you sent that tweet?

I would have put the percentage chance that we got to a million dollar run rate pretty high.

I thought probably, given that I knew what my sponsorship calendar was for the next couple months at that point and it wasn't the right run rate to get me there I probably would have put it at 20 that I actually hit a million this year.

It is the power of compounding kind of happening, where the numbers just keep getting bigger to the point where it's like what would have taken me 10 sponsored deep dives I can now do in one sponsored deep dive.

And so that just kind of all grows and compounds, I guess.

But it's still absolutely crazy.

I mean speaking of compounding.

So you had gone from a few hundred followers to 20000 followers, or 22000 followers, by that February when you sent that tweet.

You'd already doubled that then by June to 42,000.

It's crazy that you're now over 100,000.

You definitely have this thing where you're growing somewhere from 20 to 40 per month, that kind of bumps up and down.

But at this point it's probably for you more of a market saturation question of like.

When does that top of the S curve start to hit?

Or when does this thing linear out a little bit?

Yeah.

There's a little bit of a bummer in those Twitter numbers.

Which is a point of pride for a while was that I had more subscribers than I had Twitter followers.

And now I have more Twitter followers than I have subscribers.

I'm at like 105 or something on Twitter and 88 in the newsletter.

And so like, let's change that.

That probably means that I should spend a little less time tweeting.

Everybody, we need to help pack you out here.

Go subscribe if you haven't already.

In some ways it would shock me actually if, Well I know numbers-wise, there are people who listen to Acquired, who aren't subscribed to, Not Boring, but in my head I'm like who are those people?

Like we're a little bit less And this is something I wanted to talk to you about like ethereal theoretical abstract.

And frankly, like a little bit less future looking.

Like.

One question I have for you is at what point did you skeptically walk up to the Web3 cliff and then just jump off it without a parachute?

Because you did way more of that than we've done here at Acquired.

So I can imagine maybe that's a difference in audience.

But let me bring it back to, if you're not subscribed to Not Boring, oh my God, go subscribe.

Thank you.

Not boring.co.

Yeah.

So the web three point, I think the web three was a turning point.

And so you know, I wrote about for a lot of 2020, a lot of companies that are super fascinating and that I've always wanted to just like dig really deep into.

And frankly, that you all have done way better work on than I have and was able to kind of build on the back of of what you've done there.

Thank you.

Not true.

Different approaches.

Continue.

You were first.

And so I can tell you for a fact that without again, we'll go to the Tencent episode.

But without the Tencent episode on Acquired, there wouldn't probably be that not boring two-parter on Tencent.

And so either way, that is just foundational stuff.

And I realized I think probably something that I realized when I was in finance in the first place is that there are people who are just so much better at digging into public companies than I am and analyzing public companies than I am.

And so it wasn't really kind of that clean a choice to say, like you know what, instead of public companies, I'm going to do this Web3 thing.

But when I

Started writing about Web3.

I remember there was one essay that I wrote, The Value Chain of the Open Metaverse back in January where I was really apologetic almost even in the intro to that piece that I was writing about crypto and the metaverse.

And I was like, everybody, this is really weird.

My audience had become fairly FinTwit and finance heavy.

That's this year.

That's Paki McCormick writing in 2021 apologetically that, I'm sorry, I'm talking about crypto.

I mean, it shows how much the world has changed since then.

This was before Beeple's 69 million sale and a bunch of stuff that I talked about, kind of some of the early Beeple's.

Before you tried to buy the US Constitution.

Before I tried to buy the US Constitution with a bunch of friends.

But that piece ended up being, I think, really well received because it was a again optimistic take, I guess, on crypto.

It was a non-dismissive take, at least, on what was going on.

But it was really back to the basics of like all right, take a value chain, What happens when you take the middleman out?

I didn't like the language that was used around crypto at the time.

And I think it had scared me away, where it was like we're going to take down the institutions and we're going to remove the middleman and we're going to blah blah, blah.

And I was like, no, no.

All right.

So just taking a step back, if you take out somebody from the transaction and you let the consumer and the creator interact directly, more value accrues to the consumer and the creator.

And everybody out there reading is more likely to be a consumer or a creator than you are likely to be Facebook or Twitter.

So this is actually probably a pretty good thing for most of us, that there's just more value that can accrue to both sides of this equation.

And so that was kind of, I think, my jumping off point into it, when people were like oh, this is actually really interesting.

And I didn't understand this stuff at all before.

And now I really don't understand it still, but I understand it a little bit better.

And I understand that maybe it's worth looking into.

And I even set myself a rule that I would just do kind of like maybe one Web3.

I probably called it crypto back in the day before it was even called Web3.

One crypto piece a month, and then something else interesting happened.

And so then it was two.

And then other ideas that I was thinking about.

Like I wrote this piece called Power to the Person, which wasn't ostensibly about crypto, but it certainly was partially about the things that crypto lets a solo creator solopreneur, do.

And then there were a few more articles like that, where I wanted to write about something else and crypto just kind of kept creeping back into it.

And then, you know, wrote a piece that we discussed on a previous acquired episode about Ethereum, and then dove into Solana.

And I think hopefully, what I can do.

And I actually need to keep myself honest, because I'm getting so excited that I might like actually lose some of this, but really want to give the like somewhere between this is a scam and this is like going to save the world and take down the institutions.

I want to be able to give that take in the middle that is like, here's where it's good.

So I think the thing about the Solana piece maybe that worked is that it's like here's what this thing is.

Like it's a blockchain and that's crazy.

It's a platform and it needs to attract developers to build on top of the platform.

And those developers need to attract users.

And if that happens, then Solana will probably be in a pretty good shape.

And like, here's maybe one way you'd think about valuing the blockchain and go from there.

But it's really that's kind of the approach that I'm trying to take to all of this is like this is amazing.

And let's tie it back to some sort of like business concept that you're familiar with.

I like that.

That is a thing that doesn't exist.

There's a clear divide between the let's look at regular companies world and invest in regular companies world and the people who have, for lack of a better phrase, gone down the rabbit hole.

And that divide is really around business fundamentals and structure fundamentals.

Because a lot of people are like, oh, well, with DAOs, we throw everything out.

So no one even has a manager.

And of course, there's no board.

And of course, there's no shares.

And of course, there's no contracts.

And of course, there's no employment agreements.

But like...

Yeah, this way everyone gets to do what they want.

And I liked your point when you were writing about the cooperation economy, where you're sort of like well, at the end of the day, humans are still humans and do need to organize in ways that if our goal is to ship a product, we do have to figure out some structure to ship a product.

Yeah, i mean, nothing is a panacea.

I think this is a really amazing new toolkit to have and it opens up again.

I'm just probably have spent too much time in tech and vc and so i say design space now too often, but it opens up this like new design space where you just have a new set of tools that you can build with, and so dows, i think, are really great.

In certain situations.

I think you eight out of 10 DAOs might totally fail because they have that leadership issue or who is the final decision maker issue.

But I think those other two are going to do things that you might not have ever thought to do with a traditional corporation, and they'll spin up faster and they'll be more responsive.

And so I think nothing is all good and bad, but I think there are going to be some emergent properties to DAOs that are really interesting and probably previously would not have been possible.

And so that's a really good thing.

And so I don't want people to just dismiss DAOs outright because...

Sometimes they can be a little bit chaotic or whatever else.

I mean, like I got involved in the Constitution now, which was trying to buy the Constitution this week.

And it shows both the amazing things, which is, you can rally a group of people around this shared mission and raise almost 50 million to go fight to win the Constitution and bring it back to the people.

And then it's also very hard to make huge decisions in a seven-day timeframe and to organize a 20000-person Discord, all of whom has been told that they're a part of a DAO and has a voice.

And so what's the right balance there?

Then you go into the idea of progressive decentralization, which I think makes a lot of sense, which is start out kind of like a company.

And then over time, particularly if you're building a protocol or something that is not as consumer facing, maybe then over time you can kind of progressively give up control and cede more control to the users and the owners.

So I guess, yeah, again, there, the whole, the whole approach is like, here's where it's good.

Here's where there's issues.

And like, here's something that might kind of work and I don't know, let's go try it.

The worst thing you could do is just dismiss something.

Do you get blowback from people who were really into what you used to write about and are now like you got to, like spin something off or like I just can't, I'm not buying it?

Before I had, and I still have it on, but I just don't read them.

I had my unsubscribes turned on and would literally go through every time someone unsubscribed and be like someone unsubscribed.

Now, I don't care as much.

I think this is to your point earlier about getting the audience that you deserve.

Maybe there's a little I'm not comparing myself to Jeff Bezos here, but a little bit of the Amazon shareholder thing where he had to work his ass off to get the shareholders that would actually appreciate what Amazon was doing.

But then when he did, that puts you in a really great spot as a company when you have shareholders who are bought into the fact that you're going to.

Well, I think the actual quote it does make sense.

The actual quote is not, you get the shareholders you ask for.

In the long run, you get the audience you ask for.

Exactly.

And I hope, like I, what I don't want to do is alienate everybody who has like some sense of that fundamentals have like those are people that I really want to read, not boring.

And I want to keep me accountable.

But if people are just like Hey, you're writing about web three and I think it's stupid and they leave, then that's totally fine.

It's really like the people who are like Hey, you're actually like losing all sense of fundamentals here.

Like then I'm out.

Like that's when I'll know that I have an issue.

There was one.

There's somebody who DM me after I wrote the piece on Solana.

Actually that was like Man, I miss the old Packy when you would give us alpha and you'd be early on things like Snap or whatever.

And then, of course, Solana like three and a half X in the next two months.

I just gave you a truckload of alpha.

But that stuff still hurts.

I don't want to not do the thing that I'm promising to people.

But I've never had a very specific focus.

And I've always been honest that I'm going to follow whatever I think is the most interesting.

It makes my schedule miserable because I pick each week what I want to write about based on what I think the most interesting thing happening is.

But I do want to follow whatever I think is the most interesting thing going on.

And look that has attracted an audience that includes CEOs of FANG companies that are active subscribers to your newsletter.

So unless they've unsubscribed, it seems like it's working.

Did Jeff Bezos send you that email?

Yeah, Jeff and I... So the thing about Jeff is... You're not giving him the alpha anymore?

No, I'm kidding.

Jeff Bezos and I have never spoken.

He doesn't subscribe.

Someone, I think, signed up with Satya Nadella's email address, but it certainly wasn't him.

And that email address has never opened an email.

So I think that was a prank.

But I do know that CEOs of big companies and all of that... It's actually Pooja.

That would be messed up.

I was so excited.

All right.

So, speaking of Web3, you wrote in your Power to the Person piece another sort of crazy sounding prognostication, that you predicted that within a decade or two, there would be multiple trillion dollar market cap organizations that were run, quote unquote, by just one person that you called solo corporations.

And your point was, hey, it already exists.

It's called Bitcoin.

Nobody works for Bitcoin.

And it's a trillion dollar market cap.

Back to not boring itself.

It's so awesome.

It's incredible.

And Ben and I are 100 in the camp that are cheering for you that you made it to your goal of making a billion dollars in revenue this year.

A kind of old school way of thinking about that would be like Packy is the head of the distribution in the creator economy.

And one of the few people that have really broken out.

You're going to be like an NBA player.

You know level in the professional player in the creator economy.

Another way to think about where this could go, though, is no, you're building a solo corporation.

And it's not just that you're going to make a few million dollars a year writing a newsletter.

Not boring can be something a lot more.

How do you think about that?

This is, I guess, one of the hypocritical things about not boring.

Maybe is that you know I analyze everybody else's strategy and plans and all these things.

And there really isn't one for not boring.

Like what I love, not boring, to be a big and lasting thing that builds actual products and does you know?

Things that kind of outlive me a hundred percent.

I would love that.

I'm right now worried about what I'm going to write about on Monday.

And so that's both a blessing and a curse, I think, so far.

I think maybe the good thing about Not Boring has been that I'm fully focused on the content and making sure that's as good as possible.

The downside is that I'm not planning ahead by any stretch.

I'm one of the worst planners you've ever met.

Clearly, if you've been listening to this story.

Yeah.

So there isn't right now a long-term plan for something like that.

I think the really fun thing about the exponential growth of this is that new opportunities pop up.

I do think I need to put a bit of a structure in place whether that's formal or informal around not boring, so that I can have some time to focus on other opportunities, either as they arrive or God forbid proactively.

But for right now, I think one of the things that I can And this is maybe why media businesses are hard and have a hard time transitioning into into something a lot, lot bigger is that if I say you know what I really want to like go, start building apps, and I'm going to build, like I'm going to launch Paki coin, and I'm going to build a bunch of apps and make like, try to make like a billion dollars, and I don't focus on the content, the whole thing probably falls apart.

And if I bring in people to like help on the research and to ghostwrite for me and all of that, then it loses the thing.

That's one that I like doing, and two is at the core of it and on which everything else relies.

I think there's a really interesting web triangle here.

How do I figure out how to build whether it's a DAO or some loose structure around this where other people can go off and tap into the Not Boring audience and network and all of those things to build things on top that are aligned with what we're doing?

Obviously Not Boring Capital.

You can scale the outcomes with, I guess, both a combination of AUM and actual ability to invest in the right companies.

But there's not a lot of plans beyond that.

If this becomes a thing that is... a couple million dollars a year.

You'll never hear a complaint from me about that.

But certainly, I think, when I'm 80, would I want to look back and say that I built something, that the second I stop writing doesn't fall apart.

100%.

Yes.

I think it's worth spending a little bit of time on not borrowing capital.

Which is obviously not Web3, other than you are able to invest in Web3 projects via it.

But it is this really interesting thing.

And maybe it's unique to sort of our collective corner of the creator economy.

But it is a real business and it is a real step towards going from just being a.

I'm thinking about the Oprah episode that we did a year and a half ago.

Whatever it was.

Where Was it her first agent, if I'm remembering right who said look, you can be the talent in front of the camera and you can make a few million dollars a year.

You'll have a great life, right?

Or you can own the production and then you can become Oprah, right?

It does feel like there's kind of this opportunity for creators now to go from just being like an indie version of the talent in front of the camera to a lot more.

Yeah, I mean, I think certainly not pouring capital is a step in that direction.

I think the three of us are very lucky that the type of content that we make is also really well aligned with doing venture capital.

Obviously, there's a lot of creators who are starting to invest in startups.

I'm less dismissive of that.

You can probably tell at this point than most people are, because I think they probably have really deep insights into certain spaces that other people who haven't been creators and haven't built that kind of business wouldn't understand.

But I think for us in particular, we're really lucky.

You know, Harry Savings falls into this camp and a bunch of other people do as well.

Lenny and Turner all fall into this camp where we're living and breathing this stuff every day.

And this probably goes back to our conversation on journalistic integrity.

We're like, I actually don't want to do this without having skin in the game.

And I don't want to do this without kind of like digging in and getting involved in the companies that I'm writing about and trying to help shape their trajectories.

And I love picking up the phone and talking to a founder about like not just like, here's this idea that I came up with and wrote about kind of abstractly, but like here's this problem that we're having right now.

How should we think about solving this problem?

And so I think that is really a huge benefit of being able to have both the Not Boring Capital and Not Boring the newsletter.

And there's all sorts of ways that they work together.

And from a business perspective it's phenomenal because it does scale.

A lot better to run a venture fund than to show up every week and get a sponsor and then write an essay.

But again, this wasn't even planned.

It really came from one time where I wrote an essay to help a friend who was trying to explain how his company worked.

And then he raised a syndicate with somebody else.

And then that turned into my own syndicate, which turned into a fund, because it was too much of a pain in the ass to write memos every time that I wanted to do a deal.

And founders didn't want to wait three weeks to see how much money I might be able to give them.

Wait, you're telling me, as an LP, in your fund one and fund two you don't write investment memos for every single one of your Packy.

I write them up here.

Yeah.

Fun one, I did 91 investments and not all of them have investment memos.

But in all seriousness I do think that all of the time that I've spent writing about all of these different kind of industries and companies and all that really helped me show up kind of prepared and thinking about what to look for in these different businesses.

And a lot of your investments you've written about.

Yeah.

A lot of my investments I've written about.

A lot of investments frankly, come in because I start writing about Web3 and I write something like the cooperation economy that unlocks how somebody thinks about something and then they want to start.

I've had that conversation with founders a few times where they're like this is actually like we make all of our employees read this, because this is what we're trying to do.

And so like that kind of helps.

You know, on the sourcing and winning deal side.

But this wasn't planned either.

And so I think the next iteration of not boring whatever, like we kind of add on top here, it probably won't be planned, and it'll probably be because it makes sense with what I'm doing, but I could not do this.

And I didn't plan it this way.

I couldn't do this if I didn't have some sort of skin in the game with what's going on here.

And some sort of like.

I like being honest when I get stuff wrong, like billcom, my worst call of all time being short billcom only really the only time I've ever gone kind of pessimistic.

I like being called out when I'm wrong on stuff.

And I think, to be able to run a venture fund that says like, cool, here are the ideas.

But then also, like I'm putting money behind it and you'll see the results in how well fund one, fund two, fund three did.

And whether I'm just like fully talking out of my ass or only partially talking out of my ass and got lucky a little bit in the results of how these funds do.

Well, it does seem like you're publishing pretty much.

I think on Saturday you send out the email to LPs and then come Monday you send out a public version.

And it's pretty much the same.

Obviously, there's some things that the companies don't want you sharing.

But other than that, it's a remarkably transparent way of going about venture investing.

And it's also super different than classic venture capital.

Did you lead a single round?

Did you write any term sheets?

Were you the biggest check in any one of those 91 investments?

Yeah.

Never.

And that's all part of the strategy.

I mean, we all love talking about strategy and strategy isn't doing everything well.

It's picking what things you want to do well and taking advantage of those things.

And so even like figuring out how to price the round and figuring out what should go into the term sheet and spending time negotiating that and then being on a board God forbid like it actually just doesn't work with my strategy because like It is a house of cards already, where you move one thing and the whole thing breaks.

And so if I'm doing the more deeply time-consuming parts of a venture, at least as I'm currently constructed doesn't work.

But it really works very well when I can talk to a founder and we have the specific area, either internally or externally, where I can be helpful.

Not to make fun of that venture pun, but... Put on your khakis and ask the question.

Yeah.

Yeah, but there's a bunch of things that you make trade-offs throughout.

And I wrote in both the public and private memo that I'm doing probably less diligence on a specific company than most people who are investing in a company will.

And that's an embarrassing thing to say publicly when LPs are reading that or when the world is reading that, but it's a fact of the business that.

There's just no way in the world that by myself here, while I have another job and I'm investing in 91 companies, I'm going as deep, looking for the flaws in a company and calling references to look at what this person did wrong managerially.

I trust that if a good fund is leading the round or somebody that I trust is leading the round, that they've done that stuff.

And my job is, as it is with Not Boring, to look for what can go really, really right here.

And so this will either blow up totally in my face and we're in this crazy bull market and I should have been a lot more conservative and gone for VC value investing, or it'll work.

But the whole thing is transparent.

Which is a thing that's never worked, by the way.

Even Ho and Altus would probably agree with that.

I would argue.

I mean, I'm sort of doing very similar things with kindergarten ventures, with Nat.

Is what you're doing with Not Boring Capital?

So I'm arguing my own book here to a certain extent.

But I would argue you're selling yourself short with Not Boring Capital.

And I love how everything you've done is like emergent.

It's not like you cooked it all up on a whiteboard.

But it's kind of like the sponsored posts, right?

People used to think about venture capital in a box in only one way.

You did a lot of diligence.

You wrote the term sheet.

You came to evaluation.

You negotiated.

You joined the board.

You did all these things.

And obviously, that wouldn't work for what you're doing.

You've got a big business writing a newsletter.

Right.

There's aspects of what you're doing that work way better than that one specific way of thinking right, and you know you've already scaled capital under management doing this.

You could probably keep scaling even a lot further with this strategy, but what you're bringing to the table and how you're doing it is just this kind of new way of thinking right Yeah.

And there's a group of people who I think are doing this.

And I mean, you're certainly involved in this and it's maybe a liquid super team, to quote myself, which is always fun, but that's coming together and like sharing deals with each other and like trading thoughts and advice.

And here's where I think you were maybe wrong on that investment the kind of things that maybe before you would have gotten out of a partnership at a firm.

And certainly that right now you get out of a partnership at a firm.

It's not as formal and I will still make more mistakes than probably a firm will make, at least on saying yes to things that maybe I shouldn't say yes to.

But venture capital is never about the mistakes.

The only thing that matters in venture capital are the ones you get right.

And that's kind of the point, right?

There may even be one founder committing fraud that you've invested in, and it kind of doesn't matter.

To the best of my knowledge, none of my founders are committing fraud, and they're all amazing.

But I mean, you hope that doesn't happen, right?

Like I don't want to like leave room for people to commit fraud and for me to just kind of look the other way and make a quick decision and be like I don't really care.

But I'm putting trust in the overall kind of ecosystem and system that other people are doing their jobs, which again could totally blow up in my face or not.

But that's just a trade off.

Well, the way you're constructing your portfolio with 91 companies is you know, of course, look absolutely.

We don't want any fraud to happen.

Like that's not the goal.

But you've kind of shifted the mindset from like playing defense of like we're going to make sure fraud doesn't happen.

But in venture capital, the zeros are meaningless.

The most you can lose is your money.

The most you can make is a thousand times your money.

And so you want to maximize the winners.

And the thing is, because of what you're doing, with not boring, you're getting access to these great investment opportunities that otherwise, if you were a traditional venture investor, you would have to do all of that effort and work to build it.

We're going to take board seats.

We're going to give you great advice.

We're going to do all this stuff.

For you, it's a byproduct.

I think that part is totally true.

I mean, the portfolio construction thing is super interesting too, because I spent way longer than you should spend inside of even a successful startup at a startup that ended up failing.

And so I saw the other side of that where there are investors who are right off.

And at some point you just kind of stop caring about that particular company and you move on to the next one.

I really don't want to take that attitude towards it.

If there are companies that are not doing well, I want to answer their call as quickly as the companies who are doing really, really well, because I know how it feels to be on the other side of that.

But at the same time, this is why I'm totally cool with founders being investors as well and all that.

You should diversify and not put all of your eggs in one basket.

Obviously, if you're a founder and you have 1000 employees or 100 employees or even 20 employees, you have people who are relying on.

You should be giving a vast majority of your time to make sure that those people, who are definitely putting all their eggs in one basket, get the best possible outcome and as much care as they need from a leader.

But I do think there's obviously value to constructing a portfolio.

And having been on the other side of that, I appreciate that I think even more.

All right.

So we're talking about portfolio construction.

You invested in 91 companies.

You're on your second fund.

First fund was how many?

$9.99 million.

$9.99.

Your second fund's $25 million.

You couldn't get it to 10?

Oh.

You're not allowed to get it to 10.

Oh, I see.

I was going to say, you could have called me up.

I'd give you an extra 100 bucks.

And fund two, were it to exist, would potentially be in the $25 to $30 million range.

In that range.

Okay.

All right, listeners, it's time to talk about another one of our favorite companies, Statsig.

Since you last heard from us about Statsig, they have a very exciting update.

They raised their Series C, valuing them at $1.1 billion.

Yeah, huge milestone.

Congrats to the team.

And Timing is interesting because the experimentation space is really heating up.

Yes.

So why do investors value StatSeg at over a billion dollars?

It's because experimentation has become a critical part of the product stack for the world's best product teams.

Yep.

This trend started with Web 2.0 companies like Facebook and Netflix and Airbnb.

Those companies faced a problem.

How do you maintain a fast, decentralized product and engineering culture while also scaling up to thousands of employees?

Experimentation systems were a huge part of that answer.

These systems gave everyone at those companies access to a global set of product metrics, from page views to watch, time to performance.

And then every time a team released a new feature or product, they could measure the impact of that feature on those metrics.

So Facebook could set a company-wide goal like increasing time in app and let individual teams go and figure out how to achieve it.

Multiply this across thousands of engineers and PMs, and boom, you get exponential growth.

It's no wonder that experimentation is now seen as essential infrastructure.

Yep today's best product teams like Notion OpenAI, Rippling and Figma are equally reliant on experimentation.

But instead of building it in-house, they just use Statsig.

And they don't just use Statsig for experimentation.

Over the last few years, Statsig has added all the tools that fast product teams need, like feature flags, product analytics, session replays and more.

So if you would like to help your team's engineers and PMs figure out how to build faster and make smarter decisions, go to statsigcom slash acquired or click the link in the show notes.

They have a super generous free tier, a 50000 startup program and affordable enterprise contracts for large companies.

Just tell them that Ben and David sent you.

Okay.

So I think, before we move on from not boring capital as sort of this next phase, maybe it's the final additional phase of not boring.

Maybe there's more phases to come in the future.

We talked about Substack, Twitter, et cetera, the platforms enabling, not boring the media company.

AngelList enables not boring capital, enables kindergarten capital.

I've spent 11 12 years in venture, now nine or 10 of those as a traditional professional venture capitalist.

This would not have been possible.

You are one person.

You did 91 deals in fund one.

Who knows how many you'll do in future funds.

Now having the equivalent of Substack for a venture firm, It's game changing.

This was not possible before.

It's more than I'd say the equivalent of Substack for a venture firm because Substack, I still have to write everything and edit everything and make all of my own graphics and all of that.

I work with Jen on the Angelus team.

I will give Jen a shout out anywhere that I possibly can, because it is like having more than just a teammate, like a whole team team of people working with me.

I will come up with a crazy idea and be like hey, we need this crazy idea done kind of like tomorrow.

Is that okay?

I'm so sorry.

And she's like, yeah, 100%.

I went and talked to our legal team and we can make it work if we do X, Y, and Z thing.

And so having both the platform itself, which is great and makes it really easy to raise money from LPs, and for LPs to get visibility into kind of how the portfolio is performing.

All that data is a little bit delayed LPs, so it's actually performing better than it looks on there.

But really like having a teammate over there who is, like fully responsible for making sure that things go smoothly.

Let's all of this happen.

If there was no Janet Angelist, not boring capital would not 100% would not be a thing.

It's a total reorganization of the value chain by dismantling the vertical integration of venture firms.

And it's so interesting that going into this episode, I thought, oh, I see.

And this is a crude oversimplification.

But for Not Boring Capital.

Paki doesn't need to have associates that are pounding the pavement out in the community meeting with entrepreneurs, because he has a digital way to do that, called Not Boring the Newsletter.

And that way he gets deal flow from that.

But it's so much more fundamental than that.

You look at a venture firm that has 50 employees, that has several funds and has been around for a while.

It's not just that there's a massive back office that you now don't need to have two.

I mean, traditionally at venture firms, you have an IT person.

I imagine you don't have an IT person.

So not only does your media company not have a vertically integrated staff associated with it, but your venture capital firm also doesn't have a staff associated with it.

And so you actually can leverage all this new value chain that is completely reorganized for both the media and the venture capital business to stay a one-person corporation.

I mean, none of this is possible 10 years ago.

I'm not nearly technical enough to make any of this happen on my own.

I'm not organized enough to build the systems to even make it happen, even if I couldn't build software.

Having these software tools is the only reason that NotBoring exists.

I mean this is kind of the point of the power to the person piece was that there are just all of these things that you can snap off of a shelf.

And so, instead of having to deal with all of the organizational headache of managing and organizing a firm, it's very easy then to just snap one piece in at a time when you need it.

Now, it's great.

Substack is not an as-needed thing.

It's every week I'm sending on that.

AngelList is snapping a whole huge, sophisticated back office into place.

It's not even like Substack for a venture firm.

It's like AWS for a venture firm.

It's like AWS for a venture firm with a little bit of like...

Also the person doing.

You know like, let's say, I'm not technical like also the person doing the integration and setting up AWS in the first place.

There's somebody that I can ask about like, Hey, is this a thing?

Like we ask about, you know, $9.999 million for fund one.

That was, you know, through a conversation with Jen, where she's like by the way, like I looked into it, this fund actually has this many beneficiary owners, but if they're less than 10 of this, then you can do X, Y and Z thing.

And so it's even better than normal software, until AI gets a lot better because, like all the things that I'm too stupid to know, that I don't know, they can kind of anticipate and show you the ropes.

And so this is not an AngelList ad, but it is maybe a Gen ad, Gen's the best.

Nicole is also great.

She's our person there.

There you go.

Thank you, Nicole.

It is amazing that it's not just software.

And like there are like, when you think about the future and tech and like AI stealing everyone's job, maybe that happens at some point in the future.

But I think the really great thing is that it's just people kind of like pulling resources in the right place.

And then you can go access them at the time that makes sense.

So AngelList model would never work if I only paid them 25000 a year to do what they're doing for not boring.

I've getting hundreds of thousands of dollars worth of advice and service and all of that from AngelList, but they also have thousands of other clients.

And so it works.

And the more there are places that get really, really good at one specific thing, the easier it is for one person to start a business that draws from all of that.

You're championing specialization of labor.

It's like, hey, pie growth happens when everybody gets really good at one thing.

And we have a super, super liquid way of stitching all those together.

Exactly.

Okay, so we're sitting here evaluating in all the most positive ways and sunshine and butterflies around this one-person corporation thing.

What are the trade-offs?

You're a strategy person.

Where does it get hard?

So the trade-offs right now are, I don't have any outside investors.

I mean, I have LPs for the fund, but if I get hit by a bus, not boring is just done.

And that's like the extreme example and the example that everybody uses when they talk about the momentum slows a little bit.

And so it's very, very, very hard, I think, from that perspective.

You'll hear zero complaints out of me, but it's really hard to take a week off because I'm worried every time that the momentum will slow and there's not somebody else on the team who's just going to go write something else and keep the momentum going that particular week.

Maybe people don't want to come to Not Boring to read X, Y, and Z other person.

That's not the point.

I don't want to be an editor and make sure that we all have the same tone.

And so I'm kind of limited, I think, to whatever I can do as kind of one, at least kind of front person on this thing.

So that's one big downside.

The other...

I guess there's the whole churning group thesis, right?

That if you have a big audience that is loyal and dedicated to kind of this one particular thing, then you should be able to build businesses all around that person.

And like I said, I have zero time to think about building other businesses around Not Boring.

And so the sponsorship model is phenomenal and it works really, really well.

But sponsorship, if I could be using that same kind of microphone to sell my own products, that probably is actually better and higher upside and like more equity value and all of those things.

And I don't have either the capabilities or the time to build out those types of things.

I guess here's another downside with the one person model.

The more I do of that stuff, the more it dilutes the core thing and the more it makes it seem like kind of a shill factory.

Like advertising is just kind of part of the model.

But if I were like, hey, you guys should also buy Packy branded hats, they'd be like, All right.

Maybe I'll buy a hat.

Can we get some sneakers?

I'd definitely pimp some not boring sneakers.

All right.

We'll do some not boring sneakers.

That we can do.

But there are certain things where I could plug in, also to these off-the-shelf companies that let you launch your own brands and all of that.

But at some point people are like dude.

We like you because we like to read your stuff every once in a while.

Yeah. chill out with building these other businesses on the side.

And so I do think it's limited in that.

And you know exactly what you can expect.

I think it's all about expectations.

And the expectation with not boring is that it's mainly about the content and then other things that like plug in very cleanly to that content.

And the more I do things that like seem like a stretch, the more people are like you know what?

We're going to go read this other person who just does the content.

It's funny, it flies in the face of the most common advice I give Seed and Series A founders, which is until now, until product market fit you were the only reason that the business could exist.

You uniquely figured out the product that people wanted and wielded into existence and needed to do everything.

And now the only thing holding the business back is you, because you still are doing all that stuff and you need to stop and pull yourself out and hire, and you know that sort of thing.

That is like exactly not true here.

You will always be in that first phase.

And David and I will too, because we're not willing to organization build around, sort of pulling ourselves out of the core product because you are the product.

A hundred percent.

And for better or worse, right?

Like that has other benefits for you, I'm sure as well.

And for me as well, that you are the product.

You're probably more visible than CEOs of a lot of companies whose products you love.

And that gives you all sorts of other personal opportunities.

But for the business itself it means that it is harder to kind of scale it out in a predictable way.

Maybe we could both figure out how to scale these things out.

I mean, I like business breakdowns a lot from the best crew.

And so Patrick's kind of figuring out how to scale out the business.

It looks like Harry with 20BC and some of the data stuff that they're doing is figuring out how to scale out the business in different ways.

But it's really hard and it requires like...

At least for me, it would require a big pause and a step back where I was like all right, I can't do as much content for the next three months because I need to build out a team.

And I know how hard it is to hire.

I know how hard it is to manage.

I know how hard it is to manage on an ongoing basis.

And so it would be a real risky move to even hire people in and take that kind of step back that you'd need to build the structure, to build an organization on top.

It's to kind of go that morning brew route where you're like, actually there is a brand, voice and a format here.

And if we can hire correctly for people that can do the not boring thing kind of like they did for the.

I mean, it's a what is it?

A hundred person team now or something doing morning brew.

And I don't think Austin or Alex are actually writing the letter anymore, but it still feels like a pretty similar letter to what I was reading five years ago or four years ago.

So that worked.

It's a totally different way to go about it though.

And you guys could probably do it better than I could, right?

I think the great thing about that business is they had both Alex and Austin.

So if one person could focus on the content, then one person could focus on kind of building the organization and take turns and all that.

Again a little bit different with Acquired, because you're both the personalities and you're both kind of on the podcast.

But it is nice, I think, for them that they've had this partnership where I'm sitting in a room alone here.

Yeah.

But you have robots on the wall.

I have robots on the wall.

I have my brother who edits the vast majority of my pieces and helps me think through the business side.

Pooja is a saint.

And in addition to working a full-time job and managing our growing boy, also when she's dead tired on Sunday, read drafts.

I'm not solely alone here, but I also can't be like.

All right, Dan and Pooja, you write the next Not Boring while I think about building this organization.

Ben and I talk about this.

It is interesting.

I've been thinking for a long time now and certainly this is the path we've taken at Acquired of what is the ceiling to the core thing.

If the core thing is great and continues to be, do you need all the other stuff?

Do you need more shows?

Do you need more content?

Or on the internet, can it just get big?

And then when you add the capital piece too, then that is very scalable and directly related to the content as well.

So it's interesting.

I think it can scale with this one thing pretty well.

And, like everything, also kind of continues to feed off each other where, if I have a bigger portfolio of companies, but each time I mentioned a company in a newsletter it has a bigger impact because the audience has gotten bigger.

It all kind of scales with each other, which I think is really nice.

And yeah, I don't know.

I mean, if this ends up being a thing where I do one sponsored post a month instead of two and get a little bit more time to take a weekend off every once in a while, that would be great.

But there's a path to this being a million person newsletter at some point in the next five years.

I'd be very psyched about that.

From the graph I'm looking at, if it keeps this shape, it would be in the next two years.

So that's the question is how long can it continue on this 20% month over month growth?

What do you think the saturation point of your audience is?

I mean it doesn't feel as exponential the chart where it still grows 1000 to 2000 people a week.

The newsletter.

But 1,000 to 2,000 people a week is a lot different when you're at 40,000 versus 80,000.

So maybe it does go a little bit more linear than exponential at some point.

Maybe we are hitting the S part of the S curve.

I certainly hope that's not the case.

I think probably the reason that that would happen is if I get really lazy on it frankly and I'm like look, I have a big audience.

Things are great.

Making money.

This is awesome.

I'm just going to keep doing what I'm doing and don't want to mess it up.

But I think if I kind of keep pushing on the content side and keep attracting new readers who are interested and want to learn, while also kind of keeping a tether to the audience, that's there already.

And then I think it can kind of continue to grow.

And that's why I like on the content side other than just being kind of obsessed with the idea of constitution dial was like all right, I can either write a normal, not boring piece or I could like kind of go gonzo on this and like actually join it and write about what's happening and like take part in this whole thing.

And so like, I think where this ends up losing its steam is if people don't think that they can get a glimpse into the near future from reading Not Boring and a glimpse into the near future that's explained in an approachable and not crazy sounding way.

Like if I go... too far into the future, and I'm just making stuff up, then that's bad.

But if I'm just like hey, here's what happened last week, here's your tech roundup, then that's not good.

I think what I will hopefully continue to do well at is looking into the very near future, never being the earliest person on something, but being the person who can say all right, this is actually probably worth taking a look at now, and here's actually why it's not as wild as it seems, or why it is as wild as it seems, but it just might work.

That's, I think, where I can hopefully continue to grow is the future will continue to get crazier and crazier and crazier.

And so if I can just like kind of help keep translating what's going on and make people feel a little more comfortable with it, then I think I'll be able to kind of continue to grow.

I feel like you live three to six months in the possible future and we live one month into the probably future.

I don't know if you think about it that way at all, but that's like whenever I'm reading your pieces I'm like oh, I'm not there yet, but I bet this will help me get there by reading it.

The fun thing for me has been that I'm writing this like very tech optimistic newsletter in the greatest bull run ever that somehow, instead of getting you know like hitting its own S-curve, point like keeps getting wilder.

And so, you know, if that keeps happening, then I'm in really good shape.

But you know it could also slow down and like not boring is still.

I think you know, even if there's a two-year bear market, we come out the other side and reload and continue to grow and things continue to get better and all of that.

But, like those two years are going to be a really interesting time and not boring, where I'm like all right, everybody's just like.

Here's another piece talking about why we should hang on and not lose hope.

Like that will get old pretty quickly.

And so that's probably actually the biggest risk to the business in the short term, both on the venture side and the newsletter side, is that people are like.

Enough of this optimism.

Like things are kind of tough right now.

Okay, so just to highlight, before we finish history and facts here and move into powers, the insane last month speaking of compounding, like all this somehow happened in one month.

And I'm just, again, looking at your Twitter.

You went from 78,000 followers to 106,500 followers.

You made your first and then second appearance on CNBC.

You, with Chris Dixon, wrote a piece that was published in The Economist and proved to the world that you can write in The Economist's voice, not just in the unique Packy voice that I love.

That brings me three to six months of the future today.

And it is a very different voice.

I mean, you read that Economist piece and you're like wow, this is written by The Economist, not by Packy and Chris.

And, of course, speaking of Chris Dixon...

You're working with Andreessen Horowitz now.

The whole world, including Packy, they've hired.

So I want to point out all the results of this crazy compounding that unbelievably happened to you in mid-October to mid-November of 2021.

And A, what does that feel like?

And B, what are you doing with A16Z?

Yeah, so I think actually the biggest growth driver potentially was that Mario and I wrote this piece on Discord.

Oh, yeah.

And then Discord's CEO, in the replies to my tweet about the piece, announced that they were adding Web3 integrations and then announced that they were not adding Web3 integrations.

And so that brought out the deepest, darkest, worst parts of Twitter.

The replies to that were fast and furious and crazy.

But it also added, I think, a bunch of followers.

And that happened the same week that the Economist piece came out and announced the advisory at Andreessen off the back of that.

So just a bunch of things happened at the same time.

So that makes the Twitter graph look a little bit wild.

But I think that was an underappreciated one.

It's weird.

I have to pinch myself every week that this stuff is happening.

Or else it's like oh yeah, I don't know.

That was last week.

Like, what are we doing this week?

You're like picky in the brain.

Yeah.

Take over the world.

But I don't think it's compounding the same way that interest would where, like next week, even cooler things will happen.

And then next week, even cooler things will happen.

Like there will certainly be ebbs and flows.

We're going to go into the holiday season here where everything like I'm going to get panicked because my graph looks a lot flatter than it would have otherwise, actually taking some time off.

So maybe this whole thing falls apart and we regret having this conversation in the first place.

But hopefully the ebbs and flows just kind of average higher over time.

In terms of the A16Z advisory, that's a really, you know, a really fun one.

I think we're just kind of mission and values aligned.

And I think Chris said it, that there's a lot of complex stuff happening and the overall kind of like arc is really good and really positive.

But if you can't translate what's happening and why this is going to be actually good for people and like actually what's happening beneath the surface here, it's everybody's kind of just going to miss out and dismiss this whole thing.

And so I think really it's kind of the advisory there is, like you know, working with some of the companies in their portfolio to think about how they tell their story, writing pieces, like I wrote with Chris in The Economist.

They'll introduce me to companies you know that they've invested in or excited about.

Not like you know, there's no guarantee that I have to write about them or anything like that, but maybe I invest in them.

Maybe I, you know, write about them.

But I think you know the main thrust of the partnership is that we're both out there just trying to like explain what is going on and why this can be, you know, a potentially good thing, and where it can go wrong, and why it's not as scary as it seems.

And so I think it's really all about kind of that we're both.

This is going to sound way cornier than I want it to, but Both kind of just working in service of this thing that's happening.

And one of the things that I think really impressed me.

I signed on obviously, as you alluded to, in the middle of them hiring all of these people.

And so I was so excited to announce it.

And then I was like, oh, man, everybody's out.

I don't know about that.

And so I was going to do a snarky tweet.

Not snarky, but I was going to do a tweet that was kind of like, I'm joining A16Z2.

And then I went out to the offsite that the team did out in California.

And it was so clear that this big team of people was there because Andreessen was just kind of throwing its resources behind making sure that this nascent movement kind of had the resources it needed to grow.

And so there's a bunch of people working on the regulatory side there.

There's a bunch of people working on the technical side there, genius engineers who, like other Web3 protocols and companies we're trying to hire, who are just in-house there working on behalf of portfolio companies.

And I know that I'm like romanticizing the services model of venture capital right now.

And there's obviously a reason that they're doing that.

We did a two-part series on it.

Exactly.

I mean, it's good for them if the industry and their particular companies do really well, but it really feels like a group of people that just like actually believes in this thing and wants to put the management fees to work in service of it actually happening and not getting kind of choked at the beginning by over-regulation and by people's lack of understanding.

And so I came out of that feeling a lot more optimistic and just even like more excited about working with them after kind of getting to meet more of the team.

Cool.

Well, thanks for cluing us in.

I mean it's fascinating to me that yeah, that it's not like you joined the firm and you are still investing completely separately out of a separate pool of capital.

You have your own newsletter.

That's staying totally separate, but that there's.

I think it's a smart evolution of the venture model to say hey actually, crypto advisor I don't know exactly what your title is, but it's smart.

Yeah.

I mean, I've had that other conversation with funds too, where it's like hey, you want to come work and be a full-time partner at this fund.

And no, we've talked for the past couple of hours about how much fun I'm having doing this particular thing.

So that would never be an attractive model.

You're stealing the thunder on our big idea for grading.

Yeah.

Listeners, we're going to talk about this in grading because I'm curious to dig into that now.

So hold that thought for now.

Let's do powers.

You've got this concept of the not boring flywheel, which I want to say, it's kind of like you can make an Excel spreadsheet say anything.

You can put a flywheel diagram down on paper and it will always look good.

But no one has Amazon's flywheel.

And so, before actually naming the powers, you've got the not boring flywheel here that has audience at the core, that feeds out into founders, their sponsors.

We'll link to this in the show notes.

And they're sort of the Monday pieces that really feed it all and go back in and grow the audience.

And that was from a great interview you did with Jake Singer like a year plus ago, that we use as a big resource here.

Actually, right around February.

Oh, wow.

So it needs to be updated.

It probably actually was a result of the million dollar tweet.

I think that's when he was like, all right, we should talk.

I'm curious how you would describe the most powerful aspect of the flywheel.

What is the thing where you are like, oh, these mutually reinforcing aspects are strongly tied?

I think, as we talked about a little bit before, audience at the center of the flywheel is maybe not exactly the thing.

If I had a million person audience of people who didn't care about startups or whatever, it wouldn't be as powerful.

I think it's really just kind of the alignment between the content, the particular people who are in the audience and then the investing.

Those three just, I think, really work well together because they all kind of feed each other.

So that's a cop-out answer where I think I pretty much just named the whole flywheel, but I don't think there's any one particularly strong link.

I really think that it is that the content has attracted a certain type of audience member who's both more valuable to companies and who also include people who are starting companies and running companies and all of that.

And it all just kind of feeds back into each other.

But I think maybe the core part is that the content itself is so aligned with the venture business.

I think that's the magic.

With what types of companies or founders do you have strong product market fit on the investment side versus weak?

Where has it happened?

Where someone's been like, eh sorry, there's not really space in this round for this reason.

Or you're talking to somebody about sponsoring and then they're like, eh, actually no.

On the sponsor side...

Really, it comes down to price, frankly.

And I think if this were a business I'd probably be more relaxed on pricing sometimes.

But because it's me at the center of it and I'm equally happy not writing a sponsored deep dive and giving myself an extra week off.

As long as I like the company, I'd like to write about them, but I'm going to stand pretty firm on price.

And so that's where that falls apart.

It's not necessarily a particular type of company.

What's really interesting is there are actually companies that I'll say no to, that I think, that I would invest in, that I think are great businesses and that I think have something interesting strategically that just maybe isn't interesting enough to the audience where like, actually it would still perform.

And I've done stuff like this a little bit in the past and have learned from that, where it still does well, because maybe they're a high ACV product.

And if they get 50 people to sign up coming out of the newsletter, like that is a huge win.

The ROI is fantastic and all of that.

But maybe those 50 people are the only 50 people who actually cared about that particular story.

So I try to do a little bit less of that.

On the founder side.

I don't think it's a particular type of industry, as much as it really comes down to like.

Nobody gives a shit that I write, not boring.

And so that's why I'm like, I kind of bristle at the audience size being the thing.

Because if somebody comes in and they're introduced, cold to me and someone's like this is Paki from Not Boring and it's an 88000 person audience.

They're like...

Oh, cool.

You read a newsletter?

I think the divide is did the person actually read, Not Boring before, and really get value out of something that I've written, or not?

And I think that's actually where the divide is.

Such a good point.

Because otherwise, it's transactional.

And they're like, so are you going to write about me for free?

Why do I care that you have a newsletter?

A hundred percent.

And I'll get that sometimes from founders when that's kind of the introduction path, where I had a founder recently email me and ask after I said I committed and said here's what I'd love to do on the allocation side.

He was like, great.

And can you give me the open rates on your last five posts and your audience size?

And I was like, this feels more transactional than I want it to feel like.

This will be good for both of us if this works out.

Yeah, I really don't like when I'm on a pitch being like here's how the newsletter will like.

This will change your company's trajectory.

Like, I think it can be really, really helpful for companies.

And I don't want it to be this transactional thing where it's like all right, we'll give you 75000 in allocation because you have a 45 open rate and 88000 subscribers.

And I've done the math.

That doesn't feel right.

It's more like, am I aligned with this founder and excited about the story?

Put another way, the size of the audience is not important, because that is reach that a founder or company will have access to after you invest.

It's because the larger the audience size is of the right types of people, the more likely it is that someone has read something you've written and that introduction is warm and appreciated, rather than who are you.

And that mental leap is automatic.

If you're already a Not Boring fan, then you're like, oh, I get it, right?

People like me read Not Boring.

I want to get in front of more people in my orbit.

This makes sense.

The other way to describe that is I don't think it's gotten any easier convincing founders to give me allocation at.

50,000 readers or 88,000 readers.

If they're a reader, then they kind of get it.

And if they're not, then they don't.

On the sponsorship side, it's different.

There's more of an equation there and people are willing to pay more with the bigger audience, which makes total sense.

But I do think on the founder side, that's really the binary is do you read Not Boring or not?

Yeah, it makes sense.

It makes total sense.

Okay, powers.

Seven powers for not boring?

Yes.

This is going to be fun.

I'm going out on a limb here.

I think it's not going to be scaled economies.

No.

For folks.

I don't know how this could possibly be your first exposure to seven powers, because you either have listened to, Acquired or read.

Not Boring coming into this.

But briefly, the real question is what thing enables this business to achieve persistent differential returns sort of more profitable than their closest competitor on a sustainable basis for years and years and years in the future.

So, it's kind of interesting.

The first thing that I was thinking about when I was prepping for this episode is Hamilton Helmer makes the point that actually public company shareholders are not short-term oriented.

They're long-term oriented.

And that's why when you change your guidance for the next quarter...

The valuation can change by billions and billions and billions of dollars because people are accounting for the next 29 and three quarters years after next quarter in the way that they think about the trajectory of the business.

And so it's interesting thinking about the future value of not boring because it's actually much more near term than you would forecast in a public company with a durable organization and product market fit, because it's so PACI dependent.

And I know that's not naming a power and I think we should do that too, but it's an interesting observation and probably why media companies and small organizations and family-run businesses get lower multiples.

I think that's right.

I don't want to raise money because then I'd have bosses and I don't think I'd get a valuation that I'd be happy to sell part of myself for.

Yeah.

Well, David, where do you think the strongest one is?

I hadn't thought about this before going through the whole episode, but I think there's a strong element of counter-positioning here with what you're doing, at least relative to traditional media companies.

Yeah, certainly on the journalism side, actually, and on the venture side.

Totally on the venture side.

I think there may be some element of network economies here, kind of like what you were just talking about with the flywheel and being a reader.

The more people in your target audiences who are readers, the more powerful taking an investment from Not Boring Capital or sponsoring Not Boring or frankly, just continuing to read Not Boring becomes as more people in your circle are reading it.

I think that's... probably right, but I don't want to give myself too much credit on it.

And I know, like you know, there's definitely a difference between network economies and like some sort of kind of benefits to scale.

And I wouldn't call it scale economies either, where hopefully it gets better.

I think this is like data network effects or something where like, maybe it's there.

And like kind of sometimes like maybe people have it, but probably, like you say, there's data network effects, just to like pretend like there are network effects.

And I actually don't know if I have them.

Like if it means that I'm able to write about more interesting companies because there are more readers and some more different types of companies want me to tell their story and all of that, or you know, the audience is getting bigger and I have more interesting conversations with people.

So I have more interesting ideas.

Like then maybe that is there, but it's certainly not Facebook level network economies where it's very clear that one extra person coming on is really good for the people who know that person, et cetera.

Well, there's a factor of strength, of network effects and like no, you're not Facebook strength network, but I do think it's there.

Like it is valuable to me that Ben Reed's not boring.

We talk about not boring.

Yeah, it's weak though.

Like you notably don't have a community.

There's a pseudo community that exists in your Twitter replies but, like you, haven't organized the community in a way that actually has network value.

I'd say that's an opportunity.

Now, maybe one that doesn't meet the bar, but an opportunity.

I think that's 100% right.

Definitely.

I think probably because of Not Boring Club shied away from trying to be a community manager again.

But I do think Twitter is kind of where that exists now.

But I think there are absolutely opportunities.

And maybe that's where a DAO or something comes in.

Or even where Not Boring Token at some point down the line comes into play, where then you know you get all the network effects that come built in with crypto.

But for now, I don't think that it's particularly strong.

I agree.

It's pretty weak.

There's one that I want to bring up where Hamilton would probably yell at me for calling it the cornered resource of Paki.

So I guess it's probably more process power.

But you could not write a document such that you could hand it to someone else and they could do your job.

Like that, they could create the product that you create.

And I think that's definitionally process power, that you can't actually write down the process of creating the product that you create.

And I've heard you try to explain it a few times and it's always a little bit different and you can never really articulate the consistent way that lightning strikes you, such that you have a great idea.

And it seems like you go into your basement, you surf the internet and magic happens and you might have to start that process a few times.

But I don't think even you can really articulate the process by which the product comes out.

That's an incredibly good point.

I've tried to explain this many times.

It's one of the first questions that I get from people.

If I go talk to a group of people and I never have a good answer for it, because there isn't a good answer for it.

Totally.

It's funny.

We get it a lot too.

Like, what's your process?

You're like, well, I can tell you mechanically, but it's not going to sound like.

Well, Ben opens up TextEdit and he has a document that has a zillion fonts in it because it's been cloned from 250 episodes.

And that TextEdit document plus David's notion has almost nothing to do with what our actual process is to create an episode.

I mean, that's the beauty, right?

I think, for acquired, for not boring, for like good content businesses.

This is why I don't want to scale it and have to write like a brand guideline or the style guide, or even The Economist has their guide where you should be able to kind of plug into that thing and kind of sound like the brand voice.

I don't want to do that.

Okay.

So what was that process like writing for The Economist?

What was the transition from you wrote a draft to final piece?

It was pretty close.

It goes to their editors.

But the interesting thing is that they send you their guide upfront on kind of the things to avoid.

And so one of those things is to not use the word increasingly, which I then realized that I do all of the time in my writing.

But they give you those things up front so that you come in kind of aware.

And so it's as much of what you've written as it can possibly be.

And then obviously, I think just normally like an editor, they go for it, but I definitely tried to kind of, you know, catch the economist style in the thing that we wrote.

All right.

Done with powers.

Yeah, I'm with that.

I think it's process power.

At the end of the day, it's creative business.

For sure.

Now is a great time to thank good friend of the show, ServiceNow.

We have talked to listeners about ServiceNow's amazing origin story and how they've been one of the best performing companies the last decade.

But we've gotten some questions from listeners about what ServiceNow actually does.

So today, we are going to answer that question.

Well, to start, a phrase that has been used often here recently in the press is that ServiceNow is the quote-unquote AI operating system for the enterprise.

But to make that more concrete, ServiceNow started 22 years ago focused simply on automation.

They turned physical paperwork into software workflows, initially for the IT department within enterprises.

That was it.

And over time, they built on this platform going to more powerful and complex tasks.

They were expanding from serving just IT to other departments like HR finance, customer service, field operations and more.

And in the process, over the last two decades, ServiceNow has laid all the tedious groundwork necessary to connect every corner of the enterprise and enable automation to happen.

So when AI arrived, well, AI kind of just by definition is massively sophisticated task automation.

And who had already built the platform and the connective tissue within enterprises to enable that automation.

ServiceNow.

So to answer the question, what does ServiceNow do today?

We mean it when they say they connect and power every department.

IT and HR use it to manage people, devices, software licenses across the company.

Customer service uses ServiceNow for things like detecting payment failures and routing to the right team or process internally to solve it.

Or the supply chain org uses it for capacity planning, integrating with data and plans from other departments to ensure that everybody's on the same page.

No more swivel-chairing between apps to enter the same data multiple times in different places.

And just recently ServiceNow launched AI agents so that anyone working in any job can spin up an AI agent to handle the tedious stuff.

Freeing up humans for bigger picture work.

ServiceNow was named to Fortune's World's Most Admired Companies list last year and Fast Company's Best Workplace for Innovators last year.

And it's because of this vision.

If you want to take advantage of the scale and speed of ServiceNow in every corner of your business, go to servicenowcom slash acquired and just tell them that Ben and David sent you.

Thanks, ServiceNow.

All right.

So, Paki, I was thinking about this.

Should you go work at a venture firm?

And without naming a venture firm, because then it gets harder to talk about.

Let's say you were to go work at a big, big venture capital firm where a fund is like a billion dollars plus.

And, let's say, to reflect the very quick audience that you've sort of built, this relationship and community you've cultivated, and the way that you're seeing into a very important future in Web3, you would become a general partner and the offer would be for like a big let's call it I don't know what Cary is, a big firm, but call it double digit percentage of Cary and a brand new multi-billion dollar fund, or at least billion dollar fund.

So you're getting like serious economics But the returns are probably like seven plus years out in the future.

And you make a pretty good salary.

Like you probably make, I don't know, half of what not boring is baking just in salary.

So you have this sort of interesting question of like do you want to delay most of your upside another five, seven plus years?

And do you want to like cut down on something that is sort of at an inflection point right now?

Or do you want to stay the course and hope that what you're building now has way more risk?

But what you're building can eclipse even what the greatest upside would be from becoming a general partner at a big firm.

Am I thinking about that sort of right in the set of trade-offs?

I think that you're thinking about it right in the set of trade-offs.

I think the tricky part is that and Schrodinger's cat is not right here, but maybe you'll understand the right version of what I'm saying is that as soon as I go in-house somewhere, I lose half of my value, or X percent of my value.

As soon as I go in-house somewhere.

And that is kind of one.

Even though I do do sponsored posts and all of that, there is like this independent voice that I have that obviously goes away.

Everything that I write would go through a legal team and a compliance team and all of those types of things.

Probably wouldn't be able to even do it at the cadence or even the schedule that I do now, where it's like I'm making my last kind of edit or writing my last sentence 30 minutes before the piece goes out, or even a minute before the piece goes out.

So I think it would lose a little bit of that flavor.

And so I think probably you need to add like a time dimension on this, which is...

When does it make sense to do this?

And there's probably like when I'm deeply in that S curve, if I've like gotten big enough, that like somehow, just because I'm backing McCormick, people like now think that I'm smart.

Where, like now, I kind of need to prove that I can add value every week.

Like, maybe at some point in the future when there's half a million subscribers, people will just assume that I know what I'm talking about, even though I don't, and I'm just making it up every week.

Then maybe the trade makes sense both for me, because there's not that exponential upside, and for the fund, because I don't lose all of my value as soon as I set foot in the door of that fund.

But I think for the time being, it would be upside limiting for me and option limiting for me.

And it would be, you know, the fund would not, I don't think, get what it paid for.

It's funny, I'm thinking, as you're saying, that you doing this, joining a venture firm would, to my mind, be almost exactly like Amazon buying Kiva Systems.

Kiva Systems, robotic warehouse company, they had lots of clients.

I think maybe Target was a client, Walmart, lots of clients, including Amazon, lots of value.

And then at a certain point, Amazon was like okay, it's worth more to us to buy you and it's worth more to you to sell to us at amazon.

Then continue, and we're going to shut down 90 of your business, but the ultimate value is going to be higher.

I think that's probably right.

And so maybe you know where it would make sense right now is like, if there is, it's more than just you know, kind of like having a GP.

It's their strategic value in another firm not hiring me or in.

Maybe you don't have a Web3 practice, but like you need to play catch up.

I still think there are better people, frankly, who are way more technical.

It'd have to be me and some technical people who are kind of deeper in the space than me.

But maybe it helps you get a quicker leg up into an area where you feel that you're behind.

But I think you're absolutely right.

Amazon was not just making that decision based on Kiva's revenue and client roster, because that all goes away.

They're making it to keep that away from other people and to do something themselves.

There's this funny game theory thing happening here where it seems like you're willing to be reasonably public about the idea that it's not that attractive and it doesn't make sense to go join, which then makes me, with my professional venture capitalist, hat on going.

Well, I guess I don't need to do a takeout acquisition here, because he's not going to go join anywhere else either.

Or it makes me more like shoot.

If I'm going to game theory, this all the way out.

In fact, he's going to do it at some point.

Then do I actually need to make the over the top offer now to make sure that he doesn't go anywhere else in the future?

Well, I've been public about kind of everything in Not Boring's Path.

So if this does happen, if people start making big offers, I'll come back on and let you know what those offers look like.

OK, so to me, though, I think the wild cards is where, you know, it's our show.

We get to grade you.

You can chime in at the end, too.

I still think, you know, look, I feel like I'm the, I'm packy on this episode.

I'm the optimist.

The question to me, if you had that offer on the table, it'd be really hard to turn down, right?

Like that's a lot of economics and Ben's probably underselling the amount of salary you'd make every year from like the management fees on multi-billion dollars.

That's a lot of money.

Yeah.

I was trying to create this straw man.

That wasn't just like well, if you want lifestyle, you do not boring.

And if you want a whole bunch of cash now and a whole bunch of cash in the future, then you go join the firm.

It's actually not lifestyle.

I'm sorry.

Let me really restate that.

Lifestyle would be better actually in that one too.

It's control.

Yeah, if you want control now, or you want lifestyle and cash now and cash in the future.

But here's my question can you also manage billions of capital in not boring capital?

That's the question someday.

It's such an interesting question because i keep telling myself no right, and we've actually had this conversation over text and voice with this group of people before.

Right now, the answer is clearly no.

If I built out infrastructure and NotBoring keeps getting bigger and I was able to hire a really phenomenal team of people who are much smarter than me around me, would NotBoring be a platform from which you could launch a billion-dollar fund?

Potentially.

It changes the strategy completely, though.

You can't deploy a billion dollars in follow-up checks immediately.

You can't just slide in a little.

Yeah, exactly.

You'd have to be able to invest in like every, even at all reasonable company.

It just wouldn't work.

And so I'd have to change the strategy totally.

Where it's not friendly, and you'd have to go head to head with these big reputable, established firms with teams full of smart people.

And so that I think is also a limiting factor.

That said, you know, Josh and Lockie and like that group of people has turned kind of a sole capitalist thing into a bigger fund and they're competing and winning deals.

And so it's doable.

It is just a very different strategy that I don't know if I'd be good at or not.

Well, hell, Andreessen itself, the Andreessen story was that, right?

Like Mark and Ben were super angels.

They played nice with everybody.

They had everybody in the value, except maybe benchmark after the loud cloud experience.

And then they were like, well, I think we can turn this into a firm.

And they did.

Yeah.

They're a little smarter than I am.

Well, it's a different thing than being a super angel, but it doesn't mean it's not possible.

Listeners, stay tuned to find out.

As the I don't know if you're the primary or the sole shareholder of Not Boring you also kind of just get to pick.

You're like well, if this will make my life worse and I don't need to make more money, why would I do it?

I mean, I think a lot of this is don't get greedy.

I think, getting greedy, and that is hiring more people, that is lowering the bar on who I write sponsored posts on or even who the advertisers are on a normal piece.

This works if I don't get greedy and this stops working if I get greedy.

And so it's like a pretty actually clear binary there.

And maybe that means I'm being too risk averse on some things, but I'm very happy with kind of the way things are going now.

And I know that I can mess it up by getting too greedy.

Fair answer.

We'll accept it.

You guys want to do carve outs?

Yeah, let's do it.

All right, David, you first.

Okay, my carve-out fitting for my status as new dad.

This might be portending a lot of parenting carve-outs to come, but some people had told us this before we went to the hospital to give birth and I didn't pay attention and I wish I had.

So if you're a parent, you know what I'm talking about.

If you're not, this may happen to you someday.

Baby comes out and then, like babies, need to be swaddled.

Right.

And the nurses in the hospital.

They just like a regular blanket and they take it and they put the baby in the blanket and they do some folds and they're like this is how you do it.

It's so easy.

Like, oh yeah, that's so easy.

I can do that.

That's just like folding a sheet of paper.

No problem.

And then the nurses leave the room and then you're like, the baby comes out of the swaddle.

You got to reswaddle the baby.

Like I got it's just like.

And you're like whoa, how did they do that?

That was magic.

You can't do it.

New parents, do not try and swaddle your baby in a regular blanket.

Get some dedicated baby blanket, swaddles with velcro and zippers.

It will save you so much heartache.

And bring them to the hospital, for god's sakes.

Uh, that's my carve out.

Seconded boy david's carve outs have really changed Totally.

It's great advice, though.

I'll take a note.

So it's funny in prepping for carve outs for this.

Normally I have like five or six.

I can choose from that.

I'm reading that are off the wall stuff or different things I'm watching.

I'm watching succession, but I've already carved that out.

Everything that I'm reading or listening to right now is either prep for this episode or our next two episodes, which I won't spoil.

So I'm going to do something that is way too much talking my own book, but I think it's an awesome thing to read.

And we were top few posts on Hacker News yesterday.

So clearly there's other sort of heat around it.

There's a Pioneer Square Labs piece by Dave Peck, who's a veteran engineer on our team, called An Engineer's Hype-Free Observations on Web3 and Its Possibilities.

And I helped a little bit in this.

And our goal was really to take all the spelunking that our engineering team has done in the studio.

And this is people who have worked their whole careers not in crypto and explore what actually are the technical merits of these technologies.

What should be built?

Is there a lot of discussion around building but doesn't actually make a lot of sense to us why you would build that distributed.

And try and write a balanced, honest take on...

Here's what the tech can do.

Here's what the tech can't do.

And we're going to try and ignore some of the cultural elements of Web3 and just do it a little more analytically.

And of course, you can't help but throw in some cultural elements because it's a cultural movement.

But I'm really proud of how it came out.

I welcome all feedback.

And we'll put a link in the show notes.

So I'm going to keep it in Seattle for mine.

I think the last time that we talked, maybe I recommended a sci-fi book.

I've been reading a lot of sci-fi.

I think it's just.

If I'm spending so much time in real stuff when I'm writing, it's nice to turn my brain off.

The other day I finished a book and I Googled best sci-fi 2021.

And this one book came up and it was described as Haruki Murakami meets Ready Player One.

And Haruki Murakami is my favorite author.

Ready Player One, maybe not the best written book of all time, but it certainly inspired a lot of the things that people are talking about right now.

So this book is called Rabbits.

It's this thriller about this kind of global game that takes place to save the world.

And you play it by following a bunch of these coincidences that seem like coincidences but maybe they aren't.

And ultimately, playing and winning rabbits is how you kind of like reset balance in the universe.

It's, you know, again, maybe not the best written book that I've ever read.

I've heard the ending isn't great.

I haven't gotten there yet.

But it's been a really entertaining, I can't put it down kind of read.

And it has Murakami-ish vibes if it's not quite as good as Murakami.

Ooh, I'm gonna have to check this out.

And I'm learning a lot about Seattle, which is making me feel closer to Ben.

You're welcome anytime, my friend.

Seattle's such a great sci-fi, tenuous Seattle connection, but also sci-fi and sci-fi books.

I am so hype.

November 30th, which will be probably after this comes out, but before, as we're recording it, the last book of The Expanse is finally coming out.

Oh, wow.

Oh, I'm so hype.

Someone recommended The Expanse to me today.

I've never read any of them.

So I just, I bought book one.

Oh my God.

You got to read it.

It's the best.

It's so good.

Have you watched the show?

No, I've been told to read the books first and then watch the show.

I could see, having not read any of the books, at least the first two, maybe three seasons of the show were excellent.

Like some of the best sci-fi TV I've ever watched.

I'm rereading to get ready for the final book.

So there's going to be nine books total.

Eight have already come out.

The ninth is coming out.

The first two.

Amazing.

So great.

And then I would say three through three is pretty good, too.

Four, five, six and seven are like they're still really good.

Like read them through the first time.

I reread one and two and then I'm rereading eight and then I'm going to go right into nine.

Have you read Red Rising, the Red Rising trilogy?

No, I need to.

So just what you said reminded me.

Normally because again, I'm a happy-go-lucky, optimist kind of guy when people say that where they're like.

I liked one and two.

I didn't like three.

I loved four.

I hated five.

I don't have that kind of nuance in my brain.

But Red Rising it feels like it was written by not only a different person but a different species, almost after book three, like books one, two and three were so good.

And book four was an abomination.

And it's one of the few books that I've stopped in the past few years.

Wow.

Yeah.

How many books total are in the series?

I couldn't tell you.

You just stopped.

Stopped.

Wow.

Interesting.

Okay, I'll have to check it out.

One through three, though, you should definitely read once The Expanse is over.

Great.

Well, The Expanse is... If you only watch the TV show, you might not know it.

There's two authors.

So James S.A.

Corey is a pen name of the two authors who collaborate.

They are George R.R.

Martin's assistants.

No way!

So The Expanse is Game of Thrones in space.

Oh, I never realized that.

Yeah, it's really good.

All right, well, now I have to go read the books.

Me too.

Wild.

Well, Paki, we can't thank you enough for being here.

Thank you.

I mean, this was a dream come true.

This is so much fun.

It's a very unique acquired episode for us, notably not a special.

We want to be very intentional that like this is profiling the history and strategy of a company the way that we would the New York Times or Standard Oil or Amazon.

And the company just happens to be Paki.

One person at 18 months old.

It's surreal.

I also, as we drift toward our closing notes here, I was going to tell folks seriously you should go subscribe to the public acquired LP show.

Wherever you get your podcasts now.

But it's worth pointing out.

The strategy to shift to make episodes and the whole back catalog public to listeners on a new feed after two weeks of being just for the paid subscribers, is totally inspired by you, Paki.

I mean, I think, the realization that with such a smart, valuable audience, that attention is the scarce resource.

I think that part of us realizing oh, we should change the way that the limited partner program works and really make it just the limited partner community, with some early exclusive access to this content.

And actually in crypto, I guess two weeks is forever.

So that two weeks is valuable, especially as we do more crypto stuff.

But yeah, that was really largely inspired by you.

So thanks for that too.

If my biggest contribution to the world is making more great content free on the internet, I am very psyched with that legacy.

Awesome.

Well, Paki, where can listeners find you or Not Boring on the internet?

So Not Boring is at notboring.co.

I have a poorly produced podcast that you can find by searching, Not Boring Podcast.

Wherever you listen to podcasts.

We're going to get you upgraded.

We're going to get me upgraded.

Next time we do this, you're not going to be saying poorly produced.

It's not that... That is how I read Not Boring is listening.

That's true.

Yeah, I mean, none of it is overly produced, which I think is good.

Or Twitter is at P-A-C-K-Y-M.

Awesome.

And listeners, we'll catch you next time.

See you next time.

Bye.

[팩키 맥코믹과 'Not Boring': 1인 미디어 제국의 탄생과 전략]-[Not Boring (with Packy McCormick)]

📋 Summary

1인 미디어 제국: Not Boring의 성장 서사

1. 팩키 맥코믹의 배경과 형성 과정

2. 'Not Boring'의 탄생: 우연과 전략의 결합

3. 독특한 비즈니스 모델: 스폰서십과 투자

4. 핵심 전략: '최적화된 낙관주의'

5. 결론: 1인 기업의 미래

🎯Key Sentences

📝Key Phrases

📖 Transcript

[팩키 맥코믹과 'Not Boring': 1인 미디어 제국의 탄생과 전략]-[Not Boring (with Packy McCormick)]

📋 Summary

1인 미디어 제국: Not Boring의 성장 서사

1. 팩키 맥코믹의 배경과 형성 과정

2. 'Not Boring'의 탄생: 우연과 전략의 결합

3. 독특한 비즈니스 모델: 스폰서십과 투자

4. 핵심 전략: '최적화된 낙관주의'

5. 결론: 1인 기업의 미래

ListenLeap으로 딥러닝 학습

🎯Key Sentences

📝Key Phrases

📖 Transcript

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