20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable | The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

This is 20VC with me, Harry Stebbings, and this episode was about 10 years in the making.

No one actually knows this, but I started podcasting because I fell in love with Tim Ferriss' podcast 10 years ago.

I remember listening to it for the first time and I actually used his episode with Ed Cook to study for exams at school before I dropped out.

He has been a idol, inspiration, mentor to me for many years.

I'm so thrilled that we were able to do this show today.

It's one of the most thoughtful and reflective that we've done.

I'd love your feedback.

Let me know what you think.

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You have now arrived at your destination.

Tim, I'm so excited for this, dude.

As I said, I literally have my podcast because of you.

I have the name because of you.

I probably wanted to make this happen for 10 years.

So thank you so much for doing this with me, man.

I'm thrilled to be here.

And congrats on the success.

You've had some amazing interviews.

So well done.

That is very, very good.

It's amazing how far a British accent goes.

Really, like you have the intellect and I have the accent.

And I think it really elevates mine.

Just they think you're so smart in the US.

It does equalize things out.

I remember back in the day and he's actually a pretty clever guy, but people would say Lennox Lewis is a phenomenal boxer.

He is 10 times smarter than any other boxer.

And I would say, I think it's because you're American and he has a British accent.

There he is.

A certain inflation that seems to happen.

But congratulations.

Well done.

Either way, by hook or crook, you have created a very, very prominent, very compelling show.

So nicely done.

That's very, very kind of you.

You said that I could just take this in any way that I wanted.

I find it difficult, when you have a public persona, to actually separate who you are from the showman.

You know, you've got to be on show when you're doing podcasts, when you're speaking.

And I really struggle with that.

How do you think about retaining your true self when you also have to be a showman?

Well, I have thought about this very consistently since the early days, because you have to be careful which mask or masks you wear, because you can become the mask very easily.

And I think that's never been more true than now.

That's the first warning.

I would say.

Another is that if you simply respond to your audience by doing more of what they respond most strongly to, you will end up exaggerating tenfold all of your most extreme behaviors and views.

And over time, what does that mean?

You will become the embodiment of those things, even when you're off camera, off mic.

And to try to counteract some of those, I have done certain things.

For instance.

You probably have noticed I'm sure a lot of people have noticed I have not fully embraced video.

I have not gone into full production television studio land.

I have not tried to spend a lot of time on algorithms on YouTube as a driver of growth.

And part of that is because I think video puts all of those inclinations and all of those risks on steroids.

It also happens to obliterate your privacy just through giving you broader facial recognition in the world.

And as I start looking towards future chapters with parenting and kids and so on, I want less and less of that.

How do you think about balancing then reach and impact?

Me as a kid changed my life listening to your show.

I mean, genuinely.

And I might have never heard it had it not been for algorithms pushing it and distribution channels pushing it.

If you don't do video, do you worry a lot about missing out on reach?

I don't because I've seen how much you can do with very little.

And what I mean by that is if you are very, very focused in a number of ways.

There are different ways to be focused in, for instance, let's just say podcasting, although it's basically become television shows.

But let's flashback to 2014, when I started my podcast.

Do you remember how you found the show?

It probably would not have been, it wouldn't have been YouTube.

It was Apple podcast top of the charts.

Exactly.

So it would have been in the charts, or it would have been direct promotion by Apple or something like that, for instance.

Most likely, or a friend.

I firmly and maybe this is just. old fashioned.

Maybe this is extinct, but I don't think so.

I think it's going to be more and more relevant.

1000 True Fans by Kevin Kelly.

If you could only pick 1000, who would those 1000 be?

And if you pick very wisely, right, maybe those 1000, I'm just choosing some options arbitrarily.

Maybe those 1000 are the leading tastemakers in the furry community who go to conventions and you're making outfits on Etsy.

Maybe it is.

I chose a weird one on purpose.

Otherwise, it could be the thousand people who are return attendees to TED.

Could be the thousand most influential, let's just say creators, who have participated in the Olympics or at national championship level sports in half a dozen sports.

Okay.

Why are these so specific?

And they sound so maybe constrained.

My experience is, if you put in the forethought to choose those thousand people, even if you reach 10 million or 100 million, you will be able to create value highly, highly leveraged content.

Ideally, that also checks the box of being true to yourself in the sense of following your own curiosity.

And when you do that, let me just give a concrete example.

When I launched the four-hour work week, it's very tempting to try to write a book for everyone, to appeal to as many people as possible, to have the widest top of the funnel imaginable.

But in the case of The 4-Hour Workweek, I wrote that book as if I were writing it as an email to two friends, two very specific friends, with two very specific sets of challenges and problems and hopes.

I marketed that to tech-savvy males, let's just say between the ages of 20 and 35, in san francisco first, then new york city, then it hopped to the same demographic in chicago and la and so on.

Then it hopped to females in roughly those same kind of psychographics And then it spread everywhere.

So, by choosing the right starting point, the ripple effect naturally extended out to ultimately, millions upon millions of people.

So I really feel like you can go big by putting in the forethought to go surgically small.

I also remember a conversation I had very early on the podcast with Andrew Zimmern, who is a very well-known TV host chef crazy compelling, wild story of being I think he was a heroin addict, at one point homeless and has just created an empire for himself now.

And on his first episode of his first television show, Someone gave him the advice and he gave me the advice in that conversation.

He said be very careful who you pretend to be on episode one, because if that goes well, you're going to have to be that person forever or you're going to feel like you have to be that person forever.

Last thing I'll say because this is turning into a monologue is I will routinely put out things that are right in the bullseye of my interests, or weirdness, or quirkiness or goofiness that will in some ways split my audience.

And it's not for controversy.

It's to call the herd of fair weather fans who might shape me in a direction I don't want to be shaped otherwise.

So I will deliberately, kind of routinely, get rid of like 10 of my audience by just being unapologetically brazenly myself showcasing the things that I would not be inclined to showcase otherwise.

And I find that, at least for me, that has helped to keep off camera off mic Tim and on camera on mic Tim.

I think the same.

I really don't think there's a discrepancy.

If there is, it's very, very minor listen.

You said about a monologue.

I could turn this into a therapy session with you like the og, but i think we constantly debate between that.

You know doing the like the steven ball that.

Do you want a bigger penis?

Visual like someone?

It's, you know it.

You know it is not like clicking yes, Like you know, versus like Venture 101 with Kevin Rose.

And my point being, I love Kevin.

You love Kevin.

But I'm just saying like it's very easy to go down the sensationalist because we're in a relevance machine.

Algorithms drive discovery.

It's not a relevance machine.

It's a sensationalist machine.

You have to be very careful.

And that's that's conversation I have with my team constantly, also because, to their credit, they want to grow different channels.

The fastest way to do that, the easiest way to do that.

I shouldn't say it's easy, because it's actually very complicated, especially when you have to bob and weave and play the cat and mouse game with the algorithm which I have no interest in for them to get pulled into lots of big red arrows, lots of crazy click bait titles, even if it's one incremental kind of 2 shift at a time.

Before you know it, you're there and you see these numbers and you get really intoxicated.

But also, I think and this applies to startups, it applies to investing separating key metrics from vanity metrics is really important.

And I'll give an example of that.

Views, likes, all this stuff.

If your business is predicated on CPMs from ad dollars from YouTube.

Okay, maybe that is a real metric.

Otherwise, let's just say my newsletter is the most important thing.

And I would argue that it is actually one of the most high leveraged things.

Do views on clips matter?

Well, that's a good question.

What are the drivers to the newsletter?

Well, maybe it's the podcast and the blog.

Okay, do clips drive to either of those?

I've had clips, shorts, that have exceeded 100 million views.

The branding of the show is there.

It's clearly an interview on my podcast.

There's a link to the full episode.

And the impact on the long form episode has been imperceptible.

You look at the downloads and there is sweet fuck all, zero impact.

So I think it's also just worth noting these the, the teams and the platforms.

You know the teams behind the platforms are very smart.

They're very well funded, they have data scientists and teams of many others whose sole objective is to keep using the product as consistently as possible, both as a creator and as a user.

You can be swayed to adopting the metrics they want you to adopt very easily, but a lot of them don't matter if you actually drill down and look at the fundamentals of your business.

If the business matters, if you're just doing it for love of the game, then hey, knock yourself out.

No problem.

But I just constantly return to the why, why, why, why, why?

Why are we doing this?

Let's take that answer.

Well, why that?

Why does that matter?

OK, then the next one.

Well, so what?

Why does that matter?

And when you drill down, you might realize I am sleepwalking through this.

Some digital snake charmer of a platform is just pulling me through this.

And I've spent the last six months building something that doesn't actually serve my interests.

Can I ask a very direct one?

When did you feel most lost?

It could be as a podcast, but also just personally.

When you were focused on the wrong metrics, that didn't matter.

That's a very good question.

I think of myself as hopefully a teacher more than anything else.

I mean, I wanted to be a ninth grade teacher for a long time when I was younger because...

I went in a good direction due to some mentorship at that point.

A lot of my friends went in a bad direction, end up ODing and going to jail and so on.

But fundamentally, I think I've kept my eye on the ball with that specifically.

In terms of the wrong metrics, I think...

If I had to pick one, there would be the overweighing of quote unquote productivity overall, right?

Kind of like productivity is the cure-all.

And then secondly, I think that money in general has its place.

It's a currency that you can trade for other things or that you can use as a pacifier for psychological reassurance, just.

But by and large, money fixes money problems and it doesn't fix a lot of other types of problems that people expect it will.

So there does, i think, come a point, unless you ask the why why why, where you can steer yourself in the wrong direction.

For instance and this might be controversial, i don't think it is but if we take the purpose of investing as improving your quality of life or the quality of life of your family right, if we put aside the whole, like legacy, have an impact on the world, all this stuff after i die, or if i'm going to do this, giving pledge blah blah, blah.

If we just put that aside, because i'm actually skeptical of of quite a bit of that, then if you make any investments that keep you up at night, that cause you to be distracted from your family, those are bad investments, even if they're returning, record setting compounded annual growth rates.

So I think I have fallen prey to that perhaps a couple of times because I

I'm competitive, I like measuring things.

If there is a scoreboard of some type, I'm drawn to it like a moth to a flame, but you can play the wrong game.

So before the question of how do I win this game, first is to be aware of the games you're playing.

What are you already playing?

And if you have food, shelter, and a few other things, trust me, you're playing a bunch of games.

So just being aware of the games and then it's game selection, before asking the question how do I win this game?

And I slip.

I'm certainly not impeccable with that.

But if I have followed the wrong metrics, I would say, probably just overall, some type of productivity or growth metric, even if it impacts the business, which then comes back to the why build the business?

Well, if it's a business, presumably it's generating revenue and profit.

And maybe you don't need more Skittles.

Maybe you've eaten all the Skittles you need to eat.

I want to unpack those.

What do you do today?

That is less efficient than an alternative, but you choose to do it all the same.

Well, there are activities writ large that have nothing to do with, I suppose, any way I've conceived of productivity.

I mean, I read a lot more poetry now and fiction.

I never read fiction for decades.

If I can just make it up, why would I read it?

I need things that I can use.

So I read lots of fiction.

I think you can actually absorb and remember truths from fiction much more effectively than you can from nonfiction oftentimes.

Poetry, painting, digital painting on an iPad, things like this.

So activities overall that I put into my life to remind me that...

Racing to the finish line doesn't really help you because there's always more work.

The work is never done.

I think 4,000 Weeks by Oliver Berkman is an incredibly good read just to realize.

Fixing your gate on the hamster wheel does not actually lead you anywhere particularly interesting, which is not to say that being in the game is not interesting.

Like if you wanna build a business and do all this stuff, it's awesome.

Like I still do plenty of things, but I also find it helpful to use something like the way app or anything else to meditate 10 minutes once or twice a day.

Just to prove to myself if you chill out for 10 minutes twice a day, you feel better.

And guess what?

The world doesn't end and the stuff you're doing, a lot of it, even though it's meaningful to the business or whatever whatever, like a long-term.

Or if you zoom out to 30000 feet, it doesn't really matter that much.

It's not worth getting run ragged about.

So I will say that I'm sure and I've had plenty of coffee, so that might explain the word per minute rate right now.

But people might say well, that's easy for you to say, right.

You've hit escape velocity.

You've had this, that, and the other thing succeed.

So it's easy for you to be like, yeah, now I can chill out.

And I think there's some truth to that, right?

You have to be very careful when you're interviewing and when I'm interviewing folks to be ask are the habits that they're talking about post-success or pre-success?

I will say, if I could give any advice to myself of 10, 15 years ago, it would have been start meditating now.

There are a few pieces of advice I would have given, but absolutely probably with something like Transcendental Meditation or something like the Way app, that's kind of programmatic meditate twice a day.

Prove to yourself that fraying at the ends is actually not the way to be most competitive and most effective.

Tim, when did you make your first real money?

I would say, well, I made my first real money with my very, very first company.

I mean the first money that made me realize, oh wow, I can do.

What I want to do was through the sports nutrition company way back in the day, the company that I started at brain quick and back in the day, the one that, in a lot of ways, was the experience that formed the Petri dish for the four hour work week right.

There was more in that book, of course, but it was that experience of automating and outsourcing and delegating and you kind of systems thinking that led to the point where i was like oh, all these things that i wanted to do or that i thought i wanted to do i can play around with.

Like i can do these things.

Did you have a number?

Like when i was starting, i was like, if i have 10 million dollars, that's like as much as i'll ever need.

Did you have like a number?

Oh, in the beginning I think it was probably just some nice clean, arbitrary number like a million dollars.

I also had goals which were sexy and very useful at the time.

I think it's useful to have these very precise goals.

I wanted to make as much per month as I was previously making per year.

So at my startup job out of college in Silicon Valley shortly thereafter keep in mind this was 2008 the company imploded.

Everybody got fired.

And I started my own company.

I was like, you know what?

I really want to aim for this, what I considered almost absurd goal, which was making as much per month profit as I was making gross per year.

And that just seemed like it would solve almost everything.

You said there are lots of problems that money doesn't fix that people think it maybe does.

What does money not fix that people think it does?

Oh, just sit in a room of a couple, a handful of wealthy people and just listen to what they complain about all of those things, or give them a few drinks and listen to their laments and insecurities and any of the battles they or their spouses have with depression anxiety, insecurities that well up and cause all sorts of interpersonal conflict, interpersonal communication and honing EQ into something that allows you to have more harmony instead of disharmony.

I would say when I look at my friends who are billionaires, money does more to damage EQ than improve it.

Yeah, you know, I was tempted to add that, and you're right.

Money is like alcohol or power.

It is an amplifier.

So if you have insecurities, oftentimes money will amplify those.

If you're hypervigilant as I am, from a lot of childhood experiences and other things maybe it's just out of the box.

Money's going to make you extra, extra hypervigilant and, in my case, just slow to trust.

If you are a micro asshole and you get a lot of money, you're going to be a mega asshole.

The good news is also if you are inclined to be generous and you get a lot of money, you're probably going to be super generous.

So there are some upsides, but it's not selective.

Maybe it's like psychedelics also.

It's a nonspecific amplifier.

So the good and the bad are both going to get amplified.

There is that.

I just, I hesitate sometimes to bring it up because it's like, you know, cry me a river.

America weeps for the sorrows of the billionaires.

But it's true.

It's true.

So something to be aware of.

Now, if you told me that, would I have listened to all these warnings?

I would have been like, yeah, that's cute.

I'll worry about it when I get there.

And I don't think that's necessarily a bad approach to take because here's one.

I think that the Transient depression of people who are still chasing the phantom of riches is in some ways different from the depression of those who catch the rabbit on the Greyhound track and have actually hit the number.

And I'll explain why, because I've experienced both.

When you have depression anxiety, fill in the blank, but you have this big number in mind or this goal in mind, you can hold on to the hope that once you have that, these things disappear.

You no longer have to worry about them.

When you get it and you realize that, more likely than not, that is not the case, then you can feel hopeless.

Then you can really feel lost.

And I think that is part of the reason why so many people who have wealth and it's not everybody, to be clear, but so many people who have wealth actually click down into some lower levels of sort of existential distress.

Good news is I think there are ways to kind of hedge that and contend with it.

Step number one is realizing money solves money problems.

Did you find it changed your relationships?

Friends maybe listen to you more.

Your voice is a bigger voice in a family.

People don't argue with you as much.

Yeah.

I mean the family stuff.

I didn't grow up with a lot of money and money was always the if we only had more money.

And money doesn't grow on trees, you got to have money to make money.

These types of cliched expressions were something that I was steeped in.

So, given that you would imagine the same people saying those things, take me more seriously now that I've done well professionally.

As far as my friends, my closest friends are generally my oldest friends.

So I just had a gathering of six to eight of my closest friends.

They came in from all over the place.

And these are people who will always tell me that my baby's ugly if need be.

They will take the piss constantly.

These are people I've known for 30 plus years, 20 plus years.

My closest friends have not changed.

What I will say is when you have more public visibility, the volume of people who are going to be very eager to blow smoke up your ass with some ulterior motive is going to go up dramatically.

So there was a period of adjustment, for sure, after the first book hit and then stayed on the New York Times list for four and a half years or whatever.

It was where I was very vulnerable because I had not experienced that.

We think it can happen quickly.

I would take that at face value.

And lo and behold, total horseshit, 99.9% of the time.

So you develop a water feel for, I suppose, that type of nonsense or someone who's a more kind of dangerous player where they're really angling for something nefarious.

You just develop a better spider sense for all of that.

But my actual core friends have not changed.

In the same way that I've tried to pay very close attention to not wearing masks I don't want to become I've really paid attention to those friend groups.

Tim, when you look at writing, you look at podcasting, you look at angel investing and you look at wealth today, how does it distribute amongst them?

Is one 10, another 10, and one 80?

I would say...

Like maybe it's 70% angel investing, could be 80, 20% podcast, 10% books.

Then there's a bunch of other stuff that might be 5%.

So I know the numbers don't add up perfectly, but making money in books is like making money streaming music on Spotify.

It's a tough model to make work.

All five books have been number one, New York Times and or Wall Street Journal.

And in the nonfiction world, I mean, I've done about as well as books can do.

There are other books that have done better certainly, but it's in the top 1%, maybe 1% of 1%.

And nonetheless, on an annual basis and on an ongoing basis, the podcast is much larger.

I expect that to change.

I think the podcast world is going to get much more challenging, particularly with some of the decisions that I made.

But fortunately, coming back to making the audience as wide as possible, I've maintained a very tight focus.

The types of interviews I have, I don't dumb down.

So my audience tends to be very well-educated, very high household income.

And as a result, I can command and deliver on very premium CPM.

So I've positioned myself as... ultra premium very deliberately.

And that, I think, gives me more insurance against the red ocean that podcasting will continue to become.

But the downward pressure is real.

The race to the bottom dynamics are real.

So which book made the most money?

Probably the four hour work week but the success of the books, for instance.

I mean four hour body did and continues to do.

I mean the four hour body.

A lot of what was written about in that book is getting a second wind and a third wind every year for the last few years, because a lot of the scientific research publications are just supporting what was in it, and a lot of what was in there was already based on various publications and case studies in the literature.

So it wasn't just pulled out of my ass, but the four-hour body and this had nothing to do with me went completely viral on tiktok last year and just like, exploded again.

This book was published in 2010.

Why There was this guy?

He's actually very well known.

He just interviewed Joe Rogan on his podcast.

It was a very, very good conversation, actually.

Gary Brekka.

And Gary Brekka had a short video talking about the 30-30-30 rule, which alluded to a number of things in the four-hour body.

He mentioned the book by name at the end of it, and it just went completely ballistic.

Now, did that drive sales?

Because we said about the 100 million in views on the clips.

It did drive sales.

So there are exceptions.

I'm not saying that social media can't drive sales.

I'm just saying be very skeptical if you assume that to be the case.

Don't assume transference.

Prove transference.

Right.

And in this case it absolutely happened, because the numbers went nuts and the publisher was like hey, we're about to run out of stock.

What the hell is going on?

I had no idea.

One of my researchers did some homework and quickly found Gary Brekka.

We're like, oh, OK.

That's the only thing we can find that has any plausible explanatory power.

Which book did the worst?

And on reflection, can you see why it did the worst?

Yeah, I would say I mean the book that did the worst is a delta between, let's just say, expectations and reality.

I think happiness, broadly speaking and I'm not the first person to say this but Or contentment is expectation minus reality.

So you can play with that equation a couple of different ways.

Like I asked this, I'll answer your question on the book in a second, but I was talking to this Danish friend of mine because the Danes Costa Rica, Singapore and I'm skeptical of these countries, poles but are rated as some of the happiest places in the world.

And there are these speculations around the reasons, right?

Costa Rica, the social fabric, social interactions Singapore, safety net, health insurance, everything else you can imagine.

I wouldn't say health insurance, just health system blah blah blah, blah blah kind of predictability.

And I asked my Danish friend why the Danes seem so happy, why they rank so highly.

And he said, low expectations.

So low expectations, but in the case of the four hour chef.

So the four hour chef had the biggest Delta right.

Because I was coming off of the four hour work week for our body.

And then the four hour chef is actually a book on accelerated learning.

Like the whole book is about skill acquisition.

How do you learn languages?

Learn to shoot three pointers, do anything right very very, very quickly.

And that book did not do nearly as well as I would have hoped.

It still sold hundreds of thousands of copies in the first handful of months.

But the reasons that I can try to point to, there are some that are, I think, pretty much certainties.

The first is that The 4-Hour Chef was the first major book announced and launched by Amazon Publishing.

And Amazon Publishing was this huge brouhaha.

It was announced in the New York Times.

And it meant that Amazon was going to be acquiring authors, paying them just like publishers would.

And this freaked everybody out in the publishing world.

Uh-oh, Amazon's going to be competing directly against us?

What does this mean?

What is this?

There was blowback, which I expected, but the degree of the blowback, I did not expect.

I thought that Barnes & Noble might boycott it or all titles from Amazon Publishing, which they did.

I did not expect the big box retailers to do the same.

I did not expect... the pretty much full blown fatwa from traditional media that ensued.

As a result, the book got really hamstrung from the outset.

And what a lot of people don't realize is, at least at the time.

Well, this is still true for the New York Times.

But Some lists are what I would consider true bestseller lists.

So the Wall Street Journal at the time was a compiled list.

It was based off of Nielsen Book Scan.

There were others as well that followed this format.

That meant that what you see is what you get, more or less.

The New York Times list, which is still even more so.

Maybe the crown jewel is really an editor's choice list.

It's a black box.

Nobody knows how it's put together.

And some people think it's based on a handful of indie stores that they favor, based on the events they announce, plus certain retail outlets plus online.

If you only have sales through something like Amazon, which was the case for The 4-Hour Chef, you get fucked.

I mean look, it's still not bad, but I hit number.

I think it was number four on the New York Times instead of number one.

But if you looked at the Nielsen book scan, it definitely should have been number one.

I put so much into that book.

That was very, very, very, very hard.

Now, there was a silver lining on that burnout and that disappointment that we can talk about.

Namely, the podcast wouldn't have happened if all that hadn't happened.

But the other reason I think the book was difficult was entirely my fault.

I tried to do too much in one book.

And I think the title was very confusing.

The subtitle made it clear, but The 4-Hour Chef...

And just to explain it real quickly, I was using cooking, which I had attempted and failed multiple times as a journey through exploring all of these learning techniques and spent time with many of the best chefs in the world and went all over the place, learned to hunt, learned to forge all this craziness.

But I think the book tried to do too much.

That is perhaps ironic, because I was given the advice early on, after the four-hour workweek became successful, when I was invited to do all these speaking gigs.

The advice that I was given was presentations more often fail from too much information, not too little information.

I think that was perhaps a core weakness of The 4-Hour Chef.

It just tried to do too much.

The book itself is coherent.

If you read the book, it makes sense.

But the messaging, the promo, the why this book, what is this book was muddy.

And I think those are the two reasons at least I can point to why that book did not hit the expectations that I had for it.

The biggest reason CEOs are unhappy is because they attach the happiness that they have to the performance of their company.

I am inherently aligned to the numbers that I have that matter to me.

If they're down, I'm fucking depressed.

My mom's like, oh shit, bad days.

When you say that number four and you were very down and depressed.

Is it impossible to make that detachment?

And how do you think about that?

I don't think it's impossible, but when you put that much time into something and the external validation is limited to a handful of scoreboards, if you're competitive enough and driven enough to get something like that done in the first place, I think it's very unlikely you'll be completely unaffected.

But I will say that I do think about identity diversification for this reason.

And what I mean by that is having at least two or three pursuits at the same time.

And this is not being distracted.

I'll explain what I mean by that.

So, for instance, when I was working on the four hour work week, I was training really seriously in jujitsu at the time.

This was a long time ago.

I no longer do that.

Gentle art turns out not always to be super gentle.

So I've acquired quite a few.

I'm getting surgery on my elbow in two weeks because of an injury I had 20 years ago.

But I was doing jujitsu really seriously at the time.

There were a few other interests that I was pursuing in off hours.

I also keep in mind still had I still had brain quickens.

So there was also the company.

Something completely out of your control happens.

A distributor goes out of business, whatever.

If I was making progress in jujitsu, that was a psychological safety net.

My self-worth is not pinned to one variable.

That can be affected by a lot of things outside of my control.

And similarly with other books, maybe it's rock climbing, right?

Where you have a rating system, you're making progress in your climbing.

Great.

If you have a great week in the gym, even if there is a tough week of writing where you're not hitting your word count goals or whatever, you have that offset.

You have, just like in a portfolio, and I'm not look, I'm not saying you want to maximally diversify all the time, right?

It's a tough way to build wealth, at least quickly.

But that identity diversification is something that I've I've thought about and paid a lot of attention to for a couple of decades now.

But does that mean I'm immune to looking at the core numbers through Nielsen book scan and saying what the fuck?

There's a huge dislocation between I just got punished, right?

Like, I feel like this was punitive getting put in this place on this list.

Like, yeah, that's annoying.

It's very annoying.

Before you mentioned it leads to the podcast.

Before we discuss the podcast, I'm always like, you know, I've been a huge fan of yours for years.

And the angel portfolio is nuts.

It's Duolingo.

It's Uber.

It's Shopify.

It's Facebook.

It's insane.

And you honestly, it's not discussed much, which I find strange.

Can you talk to me about your favorite investing lesson on getting into one of those?

I want to leave it open to you.

Yeah, favorite investing lesson.

Or story of how it happened.

Yeah, let me just give briefly part of the origin story.

And I think that explains it.

Yeah, because I've had some pretty good luck.

And I'm not going to be one of those guys who's like, ah, it's all luck.

I don't think it's all luck, but it's definitely a component for sure.

So the way that the angel investing started is totally related to the identity of diversification stuff.

So the first book hits right and there was a lot of serendipity, but there's a lot of engineering behind why that happened.

So the book hits, meaning it hits the new york times list, then it creeps up boom, it's number one.

Then it just sticks there and then It becomes this phenomenon where it's getting like parodied in TV shows and mentioned in pop culture.

Even last year, in one of the teaser trailers for Wolverine Deadpool, the four-hour work week was mentioned right.

It's like become this thing in the zeitgeist.

And a friend of mine who I had met through an entrepreneurship class I took in college high-tech entrepreneurship taught by Ed Hsiao.

Who's this amazing, amazing figure?

His son-in-law, Mike Maples Jr., was one of the guest speakers.

So I got to know him and we kind of intermittently kept in touch.

And when I moved to Silicon Valley, five or six or whatever years later, the book hits and We ended up having breakfast together, and we would have breakfast every once in a while, or brunch at Hobie's way back in the day.

I don't know if deals still get done there, but it was.

It was kind of like bucks in Woodside where for a while it's like oh wow.

Yeah.

If you walk in at any given time, there are a bunch of VCs and entrepreneurs sitting at tables getting deals done.

So I'd sit there with Mike and my recollection is I don't think is Mike wanted to get into better shape.

And I was doing all of the self-experimentation and all of the training and all of the combing through research that later would make its way into the four hour body.

So I was helping Mike get into better shape.

And the trade was at these breakfasts.

I would ask him to tell me about the deals he was doing as an angel investor, because he had this incredible track record as an angel investor.

And he would later start floodgate and become a very, very successful venture capitalist, which he still is.

And so we're talking about these, talking about these.

He would want to ask me about the PR and marketing strategies for the four-hour work week as well.

So we just sit there and spitball stuff.

The reason I was asking about the angel investing was I recognized there was a risk of me pigeonholing myself or getting pigeonholed as a business author right.

A self-help business author.

And I recognized that was a risk.

If I stayed in that lane too long, solely in that lane, I would be afraid to step outside of that.

You see this happen all over the place.

People kind of get trapped or they feel like they're trapped in one lane.

I was also just fascinated by the world of investing.

Eventually I was like Mike, is there any chance I could co-invest with you and just put in a small check, something you know 5K, 10K and just help these startups with go-to-market plans marketing PR, anything.

I can be the most valuable, cheapest labor on their cap table.

That was kind of the pitch.

I was like, I'll take very little equity and put in way too much work.

I was like, what do you think?

To his credit, I owe him a lot of gratitude.

He was like, yeah, sure.

Let me try to pitch it.

And that's how it started.

But the mental heuristic which comes back to the lesson right or story around startup investing and this is also how i pick almost all the projects i get involved with was once i was in it seemed like i was going to angel invest.

It's like, okay.

Well, how should i think about this right?

How do i think about should i get into portfolio construction and this and read what was it?

Zero gravity book on venture capital.

And should I do it the same way as a venture capitalist?

Short answer?

No, you should not playing with your own money.

And playing with other people's money and getting management fees is a totally different thing.

But I decided because I had fantasized about going to Stanford business school for ages.

I was very unhappy at Princeton.

That's where I went as an undergrad.

I felt like I made a big mistake.

I had a lot of dark chapters there.

It did not like it.

And I was like, fuck, Stanford was the other one I wanted to go to, but I got in early at Princeton.

It was like an exploding offer.

So I kept fantasizing about going to Stanford Business School, but for a bunch of reasons I decided not to do it.

When this thing came up with Mike Maples I thought well, why don't I take what I would have spent on tuition 120K for two years, something like that?

And that would have been sunk cost.

I pay out of pocket.

And what's the hope with business school?

What you learn and the connections you make Make it worth it that you spent all this money on tuition.

So for me, I was like, all right, let me commit to putting 120 K into startups.

My assumption is like the tuition that's gone.

I'm never making that back.

I am going to optimize for building relationships, developing skills and knowledge and hopefully, developing a reputation of some type.

That's it.

Those are the three that I get.

And that's what I did for the next two years and made a bunch of mistakes.

But that is what kicked off the angel investing.

What was the biggest mistake you made, do you think?

Biggest mistake was I didn't realize in the early stages that just how effective certain founders can be with a reality distortion field in pitch meetings.

So I got really excited and my allocation was fucking terrible.

It was outsized, right?

So I have 120 K for two years.

I go in.

I think one of my earliest investments.

I was like I'm putting in 50 K and Mike was like you, sure you want to do that.

And I was like, Oh man.

Yeah.

This is really incredible.

No, I just, I see the upside potential put in 50 K almost immediately goes to zero.

I'm like, Oh my God, what am I going to do here?

I no longer have the bankroll to sustain a string of bad luck, right?

If I were playing blackjack and backing an MIT team, I just screwed up on my staking.

The silver lining on that is I had to figure out how to extend my runway.

So I talked to a couple of people who were doing advising and I figured out how to begin stepping into advising.

And ultimately, with Shopify becoming an advisor when they had whatever it was 10 or 12 employees, and then becoming an advisor at Uber.

Actually, the Uber story is very instructive.

Uber happened because I was introduced to Garrett Camp because somebody thought we would just get along.

All right.

So then, Garrett Camp is working on StumbleUpon, which delivered a lot of traffic around the web back in the day.

People might not remember that.

I became an advisor to StumbleUpon and Garrett and I worked really well together.

I really liked Garrett.

We're still friends, still close and busted my ass on StumbleUpon, right?

I was able to add value because I had an incredibly popular blog at the time so we could do all sorts of experimentation. worked a ton on the product, blah, blah, blah.

Didn't work out, right?

That was a zero for me, for me personally, as an advisor.

So I put a lot of time in it, didn't work out.

Okay, seems like a sad story.

Wah, wah, wah.

Well, what happens a few years later?

Garrett's like, hey, I have an idea I wanna bounce off of you.

And we meet up looking at these kind of sketches.

We're trading emails and that becomes UberCab LLC.

And I become one of the first three advisors.

And I think all of those advisors had been advisors to stumble upon.

So, if you're looking at it from the relationship and skill development perspective because those will transcend any given single project, even if it fails and a lot of those projects are going to fail my assumption is those just compound over time.

They snowball over time.

It's very hard to fail long term if you budget.

You have to budget your money and time appropriately.

But i just i love that example, because it's not the only example that i can point to for that kind of thing.

It's like i get involved with a startup.

It fails.

I put in tons of time but what happens right later on?

That founder introduces me to someone else who's a founder, because I was a good advisor, just a good asset, good friend reliable, able to help with dark periods, whatever.

And then that becomes, right, a 10X, 100X, 1000X or whatever.

Was Uber the best investment you've made?

Uber was the biggest outcome for sure.

Shopify could have been just as big, but I sold a lot of my Shopify as soon as lockup expired because I had no experience with public markets.

Yeah.

You're holding your face.

I mean, that would have been, that was $150 million mistake or whatever.

But I also went back and at the very beginning of COVID, cause I was tracking COVID starting in like December or early January or something like that.

When Shopify got crushed and went down to like, I'm making this up.

It's something like $200 a share or something.

I bought a bunch of Shopify.

So I actually was able to reclaim a bunch of that, which felt really good.

Cause I love those guys.

I love the company.

I'm still super bullish on those guys.

Anyway, The reason I try not to judge myself too harshly on that is at the time that that happened, the money involved.

Even though I can look back and say Jesus, I made such a huge mistake.

That money felt life-changing seven figures.

And it was life-changing, at least psychologically, but even monetarily.

It's like if I didn't know what the future held.

Who knows what any of these startups are going to do to that extent?

It was the right decision.

If I'm looking at it like a poker player, like With the data I had, with the circumstances, with the bankroll and everything considered, it was a very reasonable decision to make to sell.

But knowing what I know now, do I wish I had held it?

Yeah, of course I wish I had held it.

That's true for a bunch of companies.

By the way, the hardest question in investing is not only when to get in, but also when to get out.

Did you hold on to duo?

Yeah, duolingo I held on to because I try to learn from my past mistakes.

And I realized very quickly like do I want to compete against the citadels of the world and those people in public markets?

Like, who do I think I am?

I'm bringing a butter knife to a gunfight here.

I do not consider myself a good public markets investor investor, but you can use that.

I just realized i can't predict at all what's going to happen.

It's like i was early, i was pre-ipo on twitter and kind of sold that at the perfect time accidentally, and then was reasonably early on facebook and i sold that way too early that that was another mega, massive mistake.

I mean, god knows how much money that would be worth.

Did you sell facebook?

I can't remember.

I mean, it was not that long after IPO.

Maybe it was, I don't know, six, 12 months.

I can't remember exactly.

But huge mistake in quotation marks.

But there are examples, even with secondary transactions, where it's like okay, I sold a bunch on the secondary market with a given startup and then it goes on to 100x.

Oops.

But then there are other examples where it's like I put in many years of advising.

I sell half of it on secondary and get at least some return on investment.

And then the startup goes to zero.

Right.

So you just don't know.

I think it's important to recognize that, in so many of these circumstances at least, I have no fucking idea.

So here's the thing.

Like now my policy is just let almost everything ride.

Right.

If they go public, if they go to zero, they go to zero.

If they don't go to zero, they might go to 100x.

So just like assume you do not know and just hold on to them.

But that's the luxury of having enough cushion now.

Back in the day.

I think a lot of these decisions were the right decisions, given at least the information I had.

Tim, why did you not raise a fund?

Like podcasters can raise huge amounts of money and enjoy management fees.

Yeah.

Yeah, well, there are a few reasons for that.

So the first is I think asset accumulation and really good investing are sometimes at odds from a.

I wouldn't want to have a misalignment of incentives.

I just, I'm so hyper aware of incentives and how they drive behavior.

And The scenario I could see playing out is that, sure, raise a small fund.

Nobody raises a first small fund intending to stay with small funds, right?

I mean, that's just not how you make the math really amazing.

You have you know you do a 30 or 75 million fund, then you double or triple that and then you raise another one, and another one, and then you have overlapping funds and hallelujah right.

Things get super, super interesting.

And I was aware of that.

I'm very impatient.

I'm very, very impatient.

And so as some of my friends put it, and these are VCs, they're like, Tim, you would hate this job.

And I'm like, why would I hate this job?

And they're like, because you have to go to these meetings.

You have to handhold some of your LPs.

You have to go on the roadshow and talk to this person, who's actually not that smart, but you kind of have to get on bended knee and laugh at their jokes and do this and this.

They're like, you would fucking hate this job.

And these are close friends, right?

They're not.

And I'm not saying every VC feels this way.

But when they described like the actual ins and outs, I was like yeah, you're right.

I would hate that.

And so that's another reason.

And frankly I'm not convinced that with larger dollar amounts, this is maybe another very big reason.

I'm not convinced that with larger dollar amounts I would be able to do what I do with smaller dollar amounts.

My advice to you would have been if we'd been friends, then we'd have been hey, stay with the 50K checks.

You can afford to hold them for longer and you can afford to write more 50K checks.

And you could get into any deal with the 50 to 100K check size.

But then you stopped angel investing.

Yeah.

I mean, I guess if I were to do a fund I'd probably take the.

Oh, I'll give you another fun bit of Intel that I don't think I've talked about publicly.

So I was going to say I'd probably take the SV angel approach from back in the day, Ron Conway, you know he used to be the godfather of Silicon Valley and he was in every deal.

And it was like small checks, which is how I ended up also actually doing pretty well on a lot of things I didn't even know I was in.

But the reason I invested 25 or 50K whatever it was in SV Angel and their approach I mean it ended up being pretty smart on a lot of levels was because I got a report card on pretty much everything in the valley regularly.

And that allowed me to go hunting more effectively.

Does that make sense?

Yeah.

And so you get the report card and then you double down on three that you thought were really interesting.

I would double down or I'd be like, oh, wow, that's a really interesting sector.

Let me go look at that.

That end, just for the education also, to see what was moving and what wasn't moving, was really interesting.

How many got kind of overfunded in a sense and then went to zero or got marked down?

Like all of that stuff was super, super helpful.

What was your biggest miss?

You've been in those incredible companies from very early on.

What was the miss where you were in the room, you didn't do it, and you're like, oh.

Oh, there's so many.

There's so many.

I mean, I'd have to go back and look.

I mean, the most common way that I have missed great deals is I just have like too many email or too many inbound.

And I mentioned not being terribly patient, which I'm not proud of, by the way.

There are a lot of downsides to that, but I just have too much email.

And I would be like, Hey, you know what?

Sounds amazing.

I just don't have time to dig into this right now.

Like, I really hope it's a home run.

I'll be cheering from the sidelines.

Boom.

And then I look back a year later and I'm like, Oh my God, this company's worth a billion dollars.

Which hurts the most?

The ones that hurt the most are the ones that I sold early frankly, because I was like a hand, you know, bird in the hand, but actually this is a great one.

This is one where I'm like, Oh, maybe I should have been a little.

So one password, love those guys, love the product.

And before they had raised any money whatsoever, I met with them when I maybe they came out just to me.

Maybe they came out for other reasons.

I can't remember, but to Silicon Valley, took them out to like a gun range to shoot and just had a bunch of fun with the guys and was talking to them about possibly becoming an advisor, but they hadn't raised any money.

That idea was new to them.

They weren't sure they wanted to raise any money.

And then I saw the news of these funding rounds later and I was like, Oh God, I feel like I was 90 of the way to possibly doing a deal and What a bummer.

Cause with products like that, there's like a physiological quickening that I feel, and it sounds very unsophisticated.

But with a lot of these startups that ended up working, I feel like I kind of knew.

I was just like yeah, I mean like the the, the deck is stacked in their favor and it was a, it was, there was a feeling to it, but that that's pretty much limited to like DTC stuff, I would say.

Whenever I stray outside of stuff I could use myself, would want to use myself, could promote to my audience, whenever I stray outside of that, I get my face ripped off.

I mean, almost always.

There are a few exceptions that keep me going back to stuff I shouldn't touch.

But whenever I write bigger checks right, which is tempting.

When you have more assets under management, personal or otherwise, you're like well to move the needle.

Let's write bigger checks.

Oof. man, not a great idea.

But so the one argument to have maybe a family office would be so that I could do 50 K checks into a lot of stuff and just not deal with any of the brain damage of the paperwork and admin.

And I have people who help with a lot of that kind of stuff now, but I'm not sure that would work though, because the spray and pray thing it can work.

But the reality is, when I'm putting in these 50 K checks, I actually do a lot of diligence and like dig into it and use the product.

And I'm not sure I would have time to do that if I were doing dozens of them.

But you're right.

I did stop around 2015.

I stopped angel investing completely for a couple of years.

If I was you, I'd do a $25 million fund one.

I'd call it the four-hour fund.

I'd hire two super ambitious, energetic young associates to run around the valley with Tim Ferriss t-shirts on and do 50k checks.

And do 50k, 100k checks till the cows come home saying hey, if you're a breakout, Tim will meet you and Tim will perform for you.

And then you double down with massive SPVs 10 20 30, 40 million deal-by-deal, carry on the BCD where you'll make some serious fucking cheddar.

Yeah, it's not a bad idea.

I've thought about like the spv approach for doubling down.

Doing follow-ons is very interesting.

I've thought about it right because i've done very well investing in spvs that have launched through funds that i've invested in.

Maybe this won't surprise folks, but my favorite fund approach because generally i i don't like investing in funds.

It's like they last too long.

The capital calls are unpredictable.

So there've been multiple cases where it's like, I don't get a capital call for two years.

And then a bunch of funds come in and it like totally fucks up all my financial planning.

And I'm like, ah, Jesus, now I have to like sell something to deal with this.

I generally don't like funds, but if it's somebody very, very aggressive and very smart, who's been an operator, who has a first fund, oh man, do I love investing in those.

I love that.

Like Chris Saka's first fund.

I was literally hearing Saka, Saka.

Yeah, that would be, I mean, that's the most absurd example, right?

Because he put, I think, 500K into Uber's Series A or something like that.

He's a great investor.

So the reason I stopped angel investing was in 2015.

There was a bunch of money coming in from all sorts of places.

There was a lot of capital coming in from China, like a lot of lead investors I'd never heard of.

The other thing that was happening over that period of time and the proceeding let's just say, three or four years on mass, was that when I started, circa 2008, you had a handful of people called super angels, or like very very, very active angels, sometimes writing slightly larger checks.

Mike Maples would have been one of those.

There were a bunch of other examples.

Then you had VCs, which came in quite a bit later, and hedge funds and private equity were much much much, much later.

They weren't even aware of these deals.

Then, around 2015, a lot of the VCs started coming downstream, or upstream, as it were.

Choose your metaphor.

And they were hunting in the same ponds that the Angels were.

And before you know it, then you have like Tiger Global and all sorts of other folks who are also beginning to come further down, further down in valuation.

The valuations were getting really for me, I considered it kind of bloated.

The terms were getting super weird.

I was like, wait a second, this seems very unfavorable to investors and there are all these restrictions and it seems like i'm just going to get diluted out of existence and blah blah blah blah, blah.

And i was like you know what this is like?

I keep using card game examples.

I don't actually play cards, i don't.

I don't bet on that kind of thing.

But if you read bringing down the house or i guess the movie that was made from it 21.

It would be like, just from a strategic perspective, going from single deck blackjack to like five deck blackjack.

Like you got a big problem here and like maybe you can make it work, but counting cards is going to be pretty tough.

It just makes the game so much, so much harder.

And I was like, you know what?

In addition to this, I'm dealing with a lot of fair weather, entrepreneurs and investors, who I don't really like difficult titled.

I was like, I don't really like this new group of a lot of these folks.

And so I was like, fuck it.

I'm going to take a break because I'm easily replaceable.

If I'm just a source of capital, I want to do things that I feel like I am uniquely suited to do.

So I stopped in 2015, which also allowed me to double and triple down on the podcast, which was born of the burnout of the four-hour chef.

Why?

Because i tried to experiment with one or two different promotional channels or platforms that are increasing in importance but undervalued, and at the time, in 2012, i interviewed a bunch of my friends and also cold emailed a bunch of people podcasts that was the answer.

There are these things called podcasts.

Most people don't pay attention to them, But it seems like they are in sharp ascension and things like television, daytime TV are in sharp decline in terms of conversion to sales.

And I was like, okay, I'm going to look at podcasts for the four hour work week.

That was blogs, right?

For every book has its example.

Was it a mega hit from the first episode?

I wouldn't say it was a mega hit.

I had the benefit of a built-in audience from the blog.

In 2012, still, the blog was very, very, very popular.

This was before I made any use of email, which is funny because I was collecting emails starting in 2017 from 4hourworkweekcom and never emailed anybody.

Yeah.

I was like, I get too many email.

I don't want to get more email.

I assume other people don't either.

So I'm just not going to email these people.

I had like, when I finally went into, I think it was constant contact at the time.

I was like, holy shit, I have 300,000 email addresses or whatever it was.

So I wasn't.

I didn't use email until quite a bit later, but the podcast had its 1000 true fans from the beginning, because of the blog.

Was there a guest which blew it up?

So like for me, it was Ariel Zuckerberg in the early days.

I think the Zuckerberg name really helped, but that really instantiated us.

Was there one episode where it went boof?

I remember when you did Tony Robbins shows, they were mega.

Tony Robbins was big, but there were a few that predated Tony.

And actually my first I think my first Instagram post of all time, because I'm really hesitant to incorporate any addictive social platforms into my life.

And I haven't had any social media on my phone for two or three years at least.

But my first Instagram post of all time, I think is Tony Robbins palming my face.

So I was like, I was just like, Tony, you have the biggest hands I've ever seen in my life.

I

And she just like enveloped my whole head in his catcher's mitt.

I think that's the first Instagram post I ever put up.

But Tony Robbins was a big deal also for me because I was inspired in many ways to brainstorm and start my own company, listening to Personal Power 2 on used cassette tapes that I bought at a used bookstore, which I listened to in my piece of shit hand-me-down minivan from my mom driving to and from work, where I would commute from this tiny apartment in Mountain View right across the street from a Jack in the Box to San Jose.

So I felt a debt of gratitude to him.

Still do.

But the two episodes that come to mind I would say were Arnold Schwarzenegger and Jamie Foxx, because it was early enough in the game that a tier celebrities were not really on podcasts.

That just wasn't really a thing.

And, when I had those two on, led to a lot of promotion on Apple, keeping in mind also at that time the promise and premise of the show, which is interviewing world-class performers to deconstruct how they do what they do, like tools routines habits, favorite books, et cetera.

That was novel, right?

Now it's not novel.

There are 700 shows on YouTube that do roughly the same thing, maybe in a different way.

But at the time it was novel.

So it was a special place for people who are looking for that.

And when I got those two which took a long time to book, like a year, year and a half, I mean it took a long time to get those guys booked.

That I feel like, not only for my audience, not only for the platforms who are like holy shit, but also for me, where I was like oh, I think there's really something here.

If these folks can be on and have a great time and be willing to be on a second time because of the first experience, like holy shit.

Like I feel like this is something I should double and I should do a follow on investment on my podcasting.

Did you ever do shows where you thought that hit mega and they didn't hit?

Yeah, I have.

I don't think I'm going to name names because that's just not how I operate.

But absolutely.

I mean, there have been some very well-known folks who have been on and I haven't published the episodes because they're not.

I was just like not good enough.

And I'll usually beg off and say there was an audio problem of some type.

And I really, really, like my name in Chinese is Fei Ting Cheng or Fei Yu Cheng.

But means basically, like fey ferris, very honest, because i was so blunt in all my chinese classes so i really don't like even white lies.

But in the case of something like that i'll be like yeah, there was an audio problem.

Sorry man, We're honest.

So we don't release three out of 10, 30%.

So I've gotten to the point where that almost never, ever happens.

I would say out of 800 plus episodes there are half a dozen or fewer that would fit the category I'm describing.

It's because I got intoxicated by a name that, And one of two things are both happened.

Number one, I didn't look at long-term interview footage of them.

I just did text research and then they didn't perform or, more commonly, they could do a great job, but they just didn't take it seriously or were not playing the game.

They weren't returning serves, right?

You can have the best person in the world if they don't want to be there.

If they just got forced to do it by their publicist and your interview.

10 on a crammed radio satellite tour type day, you're fucked.

It's not going to be a good interview.

Tim, you mentioned earlier you were 48.

Do you want to be a papa?

Yeah.

Oh, yeah.

Yeah, yeah, yeah.

That's that's that's the chapter.

I think that's the next big chapter for sure.

Do you prioritize that today?

Yeah, I do.

I mean, you know, haven't had any kids that I'm aware of.

I like practicing.

Practicing's great.

But yes, it is a priority.

I do prioritize relationships and looking for... the lovely woman who will be my life partner.

And I've had some very long relationships.

It's not like I have trouble with that.

I think I have excellent taste in women and my past relationships have been great.

They just haven't ended up with kids for one reason or another.

But I've had two relationships that were five, six years in length and I'm still friends with those women.

I mean, it is entirely... doable, right?

To have kids.

I do have some fear around the permanence of it, right?

Because I look at all of my friends who have been married divorced, married again, at least in the U S, it's like the stats aren't great.

So I think part of the calculus is, is it worth it?

Even if you end up co-parenting with this person after you separate.

I think, if you choose wisely and you don't delude yourself, I think the answer is yes.

At least certainly that's what I've heard from most of my friends who end up in that position.

Is love not the ultimate sacrifice to your truly efficient mind?

Being you sleep worse with someone in the bed with you.

Of course you do whatever anyone says.

You have to give up huge amounts of time.

You're less efficient.

I mean the effective, efficient stuff.

I think can be a smokescreen for avoiding a lot of the difficult introspection required to handle the non-money problems.

So I don't worry about love being inefficient.

Like human, relationships are messy, difficult and we are not purely rational actors, which is why efficient market theory is so funny to me sometimes.

What do you think you look for in a partner that is non-typical compared to what other people would look for?

I think what I look for that may not be something people immediately pay attention to is someone who is good at deescalating conflict.

I think that is just so, so important.

Someone who's a clean fighter.

Because you're going to have fights.

Of course you're going to have fights.

So with any significant other, that's going to be the place.

So someone who's a clean fighter is good at deescalating conflict.

Someone who can apologize.

And this applies to, of course, myself as well.

Those I think are, they're really important.

You asked for maybe non-obvious, but those are things I look for.

Ideally someone also who's very good at recognizing what's inside or outside of control, which is why travel is so helpful.

Like taking a long trip with someone, it's like, what happens when the luggage gets lost?

What happens when the waiter's really difficult?

What did you learn about yourself from the two longer but failed relationships?

I think you often learn a lot about yourself from ones that didn't go to plan.

There are a couple things, right?

I grew up in a household where I would say tone wasn't great.

Lots of yelling and kind of harsh tones.

And I would say...

Patience matters, right?

Like being in a restaurant when I'm like six or seven and getting fed up with having an empty water glass and just walking into the kitchen and like finding a pitcher of water and coming back out stuff like that.

That doesn't work super well, I would say, in interpersonal dealings, especially when there's any tension.

So Learning, even temporary, like just acceptance and letting stuff kind of blow over you instead of having to react to it, right?

Acceptance over understanding, like forget about understanding.

Understanding is so overrated.

That doesn't mean you can't inquire and ask about someone's experience, how it made them feel.

All of that is important.

But seeking to quote unquote understand, super overstated, I think.

Like what does done look like when you understand X, right?

Usually what it means for type A males understand is let's debate objective reality, and I'm going to prove that I am right.

Like usually that's what it means.

Yeah.

As Terry, Terry real is a very famous couples therapist.

He has some excellent books and his position, which I think is true, is that objective reality has no place in intimate relationships.

Like if you're like, Hey, you yelled at the waiter.

And then she's like, no, I didn't yell.

And you're like, no, I hired an audiologist sitting right next to us.

And based on the accepted standards for decibel levels, like that's going nowhere.

Like that's just going to be, you're lighting your own hair on fire.

Yeah, I think that those are a few things that I've picked up over time.

And I would say furthermore, that romantic love like troubadour type love is relatively new as a basis for partnership.

This isn't something that has existed throughout all the ages.

The idea of like love being the basis and soulmate connection being the basis for lifelong partnership is relatively new on the scale of let's just call it human history and evolution.

So which is not to devalue any of that.

It's just to say it's not enough.

I would say also living as a couple, raising kids by yourselves, outside of some extended community, etc.

Also very new, relatively speaking.

So I don't think that men and women are meant to be together all the time.

I really don't think that's meant to be.

So if you're going to one way or another, choose that or be forced societally into those type of circumstances, you need tools.

And I think those tools and those communication strategies do not come naturally.

You're not just born with those.

You need to learn them through modeling or you have to study them and you have to practice them.

And I'm just saying that might sound really clinical, but I think it's true.

Do you think you should go to sleep angry?

There's like a religious divide on this stuff.

For me, I would say the answer is yes.

You can go to sleep angry, because what the alternative often means is having a heated conversation right before bed that may or may not get resolved.

Usually it's not going to get resolved.

And then I'm just more dysregulated and I can't get to sleep.

And then I'm exhausted the next day and I'm going to be even less resourced to resolve the stuff that's going on.

What I think can work, at least for me, is I'll say hey look, neither of us is super well resourced for this right now.

I recognize this is hard.

We'll figure it out.

Let's talk about it tomorrow, like after lunch, when I've gone through all this stuff, and we'll have a chance to cool down.

I like having a partner also who can just recognize like hey, we do not have what it takes right now to figure this out.

So let's calm the fuck down and we'll come back to it tomorrow or whenever.

But just having a time to reconvene so that a partner right if you might have an avoidant tendency from an attachment perspective, which I think I probably do my mom is that way super conflict avoidant, that the other person knows you're actually going to come back and have that reconnection.

And look, I'm not saying I'm a black belt in relationships, but I have learned a lot and I'm good at practicing things.

I am good at trying very, very, very methodically to get better at things.

So I've definitely gotten better.

You mentioned it was a priority.

Final one before we do a quick fire.

If we think about moving metrics that matter and priorities, Coyote, the card game.

Talk to me about why you thought that was important to do and why you wanted to do it so much.

Yeah.

So for people who are like, what the hell are they talking about?

So every couple of years I like to do something that's off menu, to see what doors it opens, what I learn, because I've never done much long term career planning.

Really it's kind of six to 12 month projects.

Let's go 100 in and i assume the doors that open, the things that appear, are things i can't predict and they'll be more interesting than anything i could have planned with any degree of certainty.

So coyote is a casual card game.

Did it in collaboration with some friends at exploding kittens, which is an awesome game design studio and, as we're talking, whenever this comes out it will have launched in amazon walmart target like 8 000 plus locations.

So and got to do my pitch.

So it has like 300 million plus social views of gameplay already, after pretty pretty much no time at all.

So, uh, we've play tested the hell of it, feel really good about it.

Like the prospects are good.

The reason I did it, I'd say probably threefold.

One is that I mentioned this gathering of friends that I have every year.

How deeply meaningful that is for us to have this offline, analog, interpersonal connecting.

It feeds us for the rest of the year.

The statistics are roughly as follows, right?

One in 25 American families or individuals have a in-person social activity planned for any given weekend.

And if you look at the decline for certain age brackets, it's like 70% down over the last 10 years.

And I see that kind of screen time, digital malaise induced loneliness, apathy et cetera in my audience.

So I wanted to create something that is a light lift that encourages offline, non-screen human interaction, which is what we are evolved for.

We are not evolved for fixating at 18 inches all day long at all.

Secondly, games have just been part of my life which I let atrophy for a long time, but I grew up just feeling like I was saved and fueled by Dungeons and Dragons and others.

I still have all of my modules and everything from when I was a kid.

When you talk to whether it's people who are striving for success or people who have quote unquote achieved success.

If they do therapy, if they have a psychedelic experience like the thing that comes back all the time is like I need more play right.

And unless they're really diligent about asking, what's the next step?

What is the next concrete action?

What I put on the calendar.

That just gets lost in the hustle of autopilot or doing whatever business gear you're accustomed to.

So that's another reason why I was like you know what I am going to spend?

It turns out two years in total trying to create the best game possible.

That's easy, fast, hilarious, just to play with friends after dinner or family or whatever.

So yeah, What is your metric for success with it?

They're different metrics.

I would say the most important one is the sounds may be squishy, but it's not when you start to actually practice it.

The relationship side, like Alon Lee, the co-founder of Exploding Kittens, worked on the first Xbox.

Halo has created entire genres of games.

Absolute polymath genius has created not just one, but many, many hit tabletop games, along with his team.

To work with him and to deepen our friendship and have a chance to just spitball, not just on games but on everything.

Huge payoff.

Just I can't even put a number on that, along with the team.

But Ilan and I have become very close.

So from a relationship payoff perspective, like I've already more than broken even with that.

In terms of learnings and skills, right?

Learning how a lot of the behind the scenes machinery works for the biggest retailers in the country, if not the world Walmart Target, right.

90% of the US is within 10 or 15 minutes of a Walmart location, right?

As an example.

I'm sure Target has similar numbers.

The scope and scale is nuts.

It's easy to forget about how much of the US economy food security is dependent on these retailers.

So understanding, like the political gamesmanship and everything that goes into getting something at mass retail, is super valuable.

And then look, would I love to have this game be the number one selling game at Walmart Target Amazon, everywhere simultaneously.

Yes.

Like that, that is in my mind.

It's a little hard to figure out exactly where to aim with that, because so much of the data is proprietary.

That's a bit of a bummer minus Amazon, which you can watch publicly.

But first and foremost, the marketing has to be the product itself.

Like when people are like, how did you launch your book?

I'm like, is your book done?

They're like, yeah, my book's done.

I'm like, it's too late for us to have a conversation.

Like the marketing has to be the product itself.

People have to want to talk about it.

We'll see.

It's my first time selling something that's $9.99 and really small.

So it's fun to promote something that is not a 600 page homework assignment, to see what that looks like.

I remember seeing the first trailer probably a month or so ago now.

I'm just going, I have to know why Tim's doing this.

Yeah, it's a bit of a WTF move.

And it's worth pointing out, too.

It's like you can do a lot in the evenings and weekends if you want to get something running in parallel.

Oh my God.

I totally agree.

Yeah.

And you can get, and you can also like the podcast, the podcast for the first 50 episodes.

I mean, it's super part-time endeavor.

That's why I advocate for 996.

You're going to hate this, but I didn't say 996 in a Chinese routine and I'm getting killed for this right now.

9am to 9pm, six days a week.

Yeah.

Yeah yeah that's, that's my.

My question is why are people working part-time?

You got sunday off.

I haven't had a sunday off in years.

People just don't want to work hard today tim.

This is the problem.

And look, people misunderstand.

You know the four-hour work week, because it's about maximizing per hour output.

If you want to work four days a week, four hours a week, four nanoseconds or 400 hours a week, i know the math doesn't work, but that's fine as long as you're really thinking about the sort of Archimedes lever approach to doing things.

And you can actually get a lot done in very concentrated periods of time.

If you step back and really aim for high leverage stuff and ask a lot of questions.

So I was chatting to Brian Johnson the other day and he was telling me about the duration of his erections.

And I said, you should steal Tim's title like I did.

Just do the four-hour erection.

Not bad.

It'd probably click, wouldn't you, Tim?

Yeah, click.

Yeah, sure.

I mean, the trade-off is you may need to go to bed after 8 p.m. to make good use of those erections.

It depends on how much, how many lunchtime nookie sessions you can have.

No, no, no, no.

You don't do that because that's too much energy at lunchtime, Tim.

No, no, that doesn't fit in your routine.

Yeah, yeah.

Doing red light therapy for my penis at that time.

Brian's run a lot of interesting experiments.

If somebody wants to.

I interviewed him on the Braintree stuff before the transformation into Don't Die.

So if you want a before and after.

Do you believe that he's doing this out of like genuine passion for it, or is it custom acquisition for Blueprint and for the company that is built behind it?

I don't know.

I don't think they're necessarily mutually exclusive.

I mean, he's definitely interested in building a company.

Maybe some of the attacks on various things were basically just setting the stage for launching products and customer acquisition.

But I also feel like he's sincere in a lot of the experimentation and the pursuit of longevity and healthspan.

I feel like he's... my impression is that, that he's sincere, but those are not mutually exclusive.

And we were talking about incentives, like can incentives steer and impact other areas?

Absolutely.

So who knows, but have you interviewed him on your show or not yet?

Or I guess maybe it's not a thematic thing.

Yeah no, i have.

He told me about his erections and i said dude, you could watch titanic in that time right seriously, and and he now uses that in all of his talks, and so i feel incredibly proud and and just because i, i i don't want to feel like, you know, we're throwing them under the bus.

It's like We're giving him credit on a large platform that he has massive erections.

How is this throwing him under the bus?

No, it's not throwing him under the bus, but erections do matter, just to be clear.

And a heuristic for a lot of male health is I owe this to Kelly Starrett, who's a very famous PT and performance coach but boner, no boner.

When, like in the morning, does it happen or doesn't it, does it not happen?

Like that is actually like a good leading indicator for a lot of things.

My god, I so want to do 20 VC with Tim Farris.

Erections matter.

I mean yeah, big red arrow on the thumbnail Pointing to the microphone in front of me.

Yeah.

I want to do a quick fire with you.

What is a piece of advice you gave in your 30s that you wouldn't give today?

I would probably just add some asterisks to a few things like what gets measured gets managed.

I measure what matters, but not everything that matters is easy or even possible to measure.

And you can lead yourself astray by trying to do that.

So I would add that any advice or videos that I put together involving high heat and eating things out of plastic or drinking things out of plastic, I would rescind.

And this is not tinfoil hat wearing territory.

I mean, I really feel like minimizing microplastic exposure here is a good investment.

So this, this ronda patrick talks a lot about this from a credible perspective, but like not putting tea bags in hot water, any of the disposable to-go cups in most places outside of maybe blue bottle coffee, which uses sugar cane coating, i believe so you're putting hot water, hot coffee, hot matcha, whatever.

In that you are consuming lots of microplastics.

That's one that comes to mind.

What's the one person you'd most like to have dinner with, dead or alive, and what would you ask them?

It would probably be someone dead.

I can't hone down to one, but let's just say Richard Feynman, Ben Franklin, or Seneca the Younger.

And I imagine they're kind of blowhards.

They're all going to talk a lot, but I would interject and ask, what did you learn from that?

How do you feel about that?

What were you saying to yourself when that happened or before that conversation?

The inner monologue piece is effectively self-coaching.

I find that type of question really fruitful.

So I would probably just...

I'm sure they would all run long and over talk and I would get annoyed.

But I'd say those three come to mind.

Tim, how has your style of interviewing changed?

You're one of the greatest interviewers.

How has your style changed over the, whatever it is, 850 now, close to?

Yeah, something like that.

I would say that I still try to deliver on the promise of the show, right?

Which is kind of practical tactical strategies tools frameworks, whatever that you can use from these people, whether it's a Seinfeld or an unknown Japanese knife maker, something like that.

But the older I get, the more I have realized that the emotional terrain matters, right?

The inner game, not just from a mental performance perspective, but from an emotional navigation regulation perspective, from a mental health perspective.

I've asked more questions about those facets in my interviews, because I don't think that you can separate any of these things.

They're all integrally interconnected, just like mind-body.

That's a false dichotomy, like Cartesian duality doesn't make any sense if you just look at any modern biology and understanding of, for instance, psychiatric conditions.

So I've tried to make the interviews useful, but more holistically useful.

Because it's also easy to emulate or copy someone without realizing the hidden costs of what makes them so good at X right.

You could be like all right, I'm making this up just because it's an easy one but, like killer finance person X, they wrote this book on how they do what they do.

I'm just going to copy that, but they don't talk about their three divorces.

They don't talk about their battle with alcoholism.

They don't talk about all of these things that may be independent.

Maybe they're on separate tracks, but maybe they're actually a direct side effect of the things you're about to copy.

So I really try to flesh some of these things out.

So if people are going to emulate these folks, they get a more complete picture.

Tim, as I said at the beginning, I wouldn't actually have my business without you.

I wouldn't have my funds without you.

It would be entirely differently named, which probably wouldn't have been successful.

I probably wouldn't have started a podcast.

So of all the guests I've ever had on, I probably owe the biggest debt of gratitude to you.

So thank you.

Oh, thanks, Harry.

I really appreciate you and everything that I've learned because I wouldn't have my life without it.

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[Tim Ferriss on Identity, Investing, and the Art of Living]-[20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable]

📋 Summary

Navigating the Persona: The Danger of the Mask

The Fallacy of Productivity and Vanity Metrics

Angel Investing: Relationships Over Returns

The Evolution of Content and Personal Life

Final Wisdom: The Power of Play

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📖 Transcript

[Tim Ferriss on Identity, Investing, and the Art of Living]-[20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable]

📋 Summary

Navigating the Persona: The Danger of the Mask

The Fallacy of Productivity and Vanity Metrics

Angel Investing: Relationships Over Returns

The Evolution of Content and Personal Life

Final Wisdom: The Power of Play

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🎯Key Sentences

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