Brian Johnson wants to break the chains of biology.
I want to break the chains of time.
We can always raise another round or do another trade, but you can't raise another decade.
You're running a massive company.
You also do investing.
You're also happy married with four kids.
I know the way that you do it all is delegation.
What is the secret that you've figured out?
Cardinal sin of delegation is that it will be faster or better to do it myself.
And the reason it's a blocker is because it's true.
But the only way you get leverage is by going through that work.
A couple decades ago you had to be Marc Andreessen or Vinod Khosla to have half a dozen assistants and that cost you half a million dollars.
Now with a company like Athena, for 3,000 bucks a month, you can have your own assistant.
What have you learned in your extensive founder career?
Most people think about delegation as a convenience.
Jonathan Swanson thinks about it as a system for living and has built his career around a simple idea.
If you don't have an assistant, you are the assistant.
He scaled Bumtac into one of the major home services marketplaces for the last decade.
Now he's doing it again with Athena the number one place to hire a personal assistant who can run your calendar, your operations, your home and increasingly, your AI workflows.
Jonathan is running a 4,000-person company while investing on the side and raising four kids.
The through line is a very intentional philosophy of time.
He believes most people underestimate how much ambition they unlock when they learn to delegate well.
In this conversation we talk about how elite assistant culture shapes him, what founders consistently get wrong about leverage and why he thinks billions of people will soon be delegating to a mix of human and AI partners.
We get into delegation frameworks, splitting work across multiple assistants, how chief of staffs fit in and the mindset shift required to stop optimizing for speed today and start optimizing for compounding tomorrow.
We hope you enjoy.
Jonathan, welcome to the podcast.
Thanks for having me.
So Jonathan, you're running a massive company, what, 4,000 employees?
4,000.
4,000 employees.
You also do investing.
You're also happy marriage with four kids.
How do you do it all?
I know the way that you do it all is delegation.
You have a chief of staff, a bunch of EAs.
Why don't you talk about what is the secret that you've figured out that other people can learn from?
Yeah.
So my origin story here is out of school.
I worked at the White House and I sat in the West Wing next to the president's executive assistants.
And as you might imagine, the EAs in the West Wing were really freaking good.
And it set my bar super high for what this EA client partnership could look like.
And when I moved to San Francisco to start Thumbtack, I said okay, I'm not president, but what if I had an EAN support team that was as good as the president's?
What could I accomplish?
And so, at Thumbtack, as we were scaling the business, I hired my first assistant in the Philippines, started helping me with basic stuff inbox, calendar and then we just got creative and we did more and more complex, interesting things which we can talk about.
And what I found was the more leverage I got, the more ambition I got, and it just compounded.
And it started with one assistant.
Now I've got a half dozen, and every assistant gives me more leverage to take on more things.
It's fascinating because some people say hey, Bill Gates is so much richer than me, but he has the same phone that I have.
Or I remember maybe it was you, maybe it was someone else who was like the president should have way better information than me, and yet they're reading Politico too.
They're reading the same media too.
And this is another example of it, which is A democratization where a White House have amazing assistants but thanks to Athena and technology, at some point everyone will have a certain.
Exactly.
A couple of decades ago, you had to be Marc Andreessen or Vinod Khosla to have a half dozen assistants.
And that cost you half a million dollars.
Now with a company like Athena, for $3,000 a month, you can have your own assistant.
And then with AI, yeah, it's going to become ubiquitous.
There's going to be billions of people learning to delegate to a machine assistant.
And as your budget increases, you might add a human or a chief of staff on top, but it's just kind of a ladder of leverage.
How should we think about what are the things that humans can do versus what are the things that AI can do?
I remember my friend started Clara a decade ago, which is trying to be AI assistants effectively.
Obviously, this was well before AI. a lot of the innovation.
But what is the right way of thinking about sort of the human-AI relationship?
Yeah, I mean, it's a moving target, obviously.
AI is going to get increasingly more capable.
And our view is it's like self-driving cars where it's not self-driving overnight.
It's you drive the Tesla at first, and then there's assisted steering and braking, and then over time it becomes more autonomous.
And the same thing is going to happen with assistants.
My view here for founders is if you don't have an assistant, you are the assistant and you don't want to be the assistant.
And so no matter your budget, you should first start by learning to delegate.
And if you only got 20 bucks a month, you start by delegating to ChatGPT.
And prompt engineering is really just delegating.
And if you become world class at leveraging ChatGPT to brainstorm your goals, figure out how you can take the next step in the business.
Once you have the budget for a human assistant or chief of staff, then you're prepared to go that next level.
So you start $20 a month.
If you have budget, then you hire someone direct with a service like Athena.
If you have enough money, you hire someone in person.
That's six figures.
And if you're a legendary budget, then you've got a suite of assistants and chief of staffs following you around.
Yeah.
So I've had Anithya Yeh for many years now, and she's absolutely amazing.
And I use her for scheduling and typical assistant activities.
But you have many assistants.
Our friend Sam Korkos has a bunch of assistants as well.
What else do people get leverage on or delegate that maybe is not obvious?
So first you start by taking the pain off of your life.
So I never wait on hold, I never put my credit card in the internet, I would never fill out DMV forms, never do passport renewal.
The world is full of all these annoyances, and so first you take off these things that drain you, that don't give you leverage.
Then, once you've done that, then the next thing is you raise your sights and you're like what's a new business I could start.
How can I scale my business faster?
How can I spend more time with my family?
What are the things I actually care to do a lot more of?
And so I start with basic stuff inbox calendar, stuff that everyone does, but then I just start experimenting.
And so during the scale-up days of Thumbtack, when we're in a house working all the time, I told Marnie, my assistant I don't really have any friends outside of work.
I was like, the only people I know are in this building.
I need to make some friends.
And so I told her, let's plan a founder dinner at my house every other week.
And we did lots of this together back in the day.
And that's how I made all my best friends.
And I just walked home from work and Marnie had invited people, set up the chef and the bartender.
And we walk in and we make new friends.
And I met Catherine, my wife, through that.
And then Marnie's helping plan our wedding.
And now Marnie helps us with our kids.
And so it starts small, and then you just kind of compound these things.
Yeah, but even in that example, say more about how did she know who to reach out to?
Yeah, so the kind of entry-level delegation is you delegate by task.
You say, help me plan this dinner party.
If you just say that, you're not going to get what you want.
The more advanced way to delegate is called delegate by algorithm, where you actually export your own internal preferences as you delegate.
So I would say, hey, when I plan dinner parties, I like to have six to eight people.
I like people to have raised similar amounts of capital or be at similar stages or similar number of employees and literally write an algorithm for how you find the right people.
And then... you give feedback on whether it worked or not.
And once the algorithm is fully exported from your head, then it's just rinse and repeat.
And so engineers tend to be better at creating these kind of like SOPs or standard practices, but it's something that you can learn to do.
Yeah.
And so share more about.
For people with multiple assistants, how do you differentiate like, how do you sort of delegate across the team?
Yeah, I mean, start with one.
And then, like any team, you specialize.
And so I just had one that did everything as a generalist, and now I have a dozen, which I know sounds crazy, but each one specializes in different things.
One is on work, one is on home, one is on kids, family, travel, finances.
And that specialization is helpful because the finance person is just thinking about balance sheet, sending wires, all that sort of stuff.
And then I have a chief of staff who sits on top, who distributes work across all of them.
What are other principles?
Like, I love this delegate by algorithm, not by task.
What are other principles or frameworks that are really important or not obvious to get the most out of an assistant?
Yeah, the cardinal sin of delegation is that it will be faster or better to do it myself.
That's the number one blocker for most people.
And the reason it's a blocker is because it's true.
Yeah.
It will actually be faster or better if you do it yourself that first time.
It takes more effort to delegate to teach someone how to do it.
It might not be as fast or as good as you'd like it, but the only way you get leverage is by going through that work.
You have to overcome that activation energy.
The second mistake people make is they don't compound for the long-term and they hire someone and then switch an assistant every six, 12 months.
But it's the compounding that creates incredible leverage.
I've been working with Marnie for a decade, like a little sister now, and she knows everything about me.
So that's just kind of like common principles.
In terms of the way to delegate, I think this is just tactical, the methods.
The most common way people delegate is with your thumbs on your phone.
That's the worst way, very slow.
Better to use all 10 fingers at a computer, but that's actually pretty slow as well.
The best way to really delegate is using your voice.
And so voice, you can talk two to three times faster.
You can do it on the go.
You can do it on a date and between lunch and the Uber.
At Thumbtack during hyperscale times I would walk between meetings and between a meeting I would be voice noting to an assistant.
Here's the takeaways pre-draft these five emails follow up with this person.
And all my work from that meeting was actually delegated by the time I started the next meeting.
Versus everything kind of accumulating.
And then you get to the end of the day and you're like, I have a hundred things to do.
And so learning to delegate by voice.
If you look at all the super delegators at Athena, they are all just delegating by voice all day long.
Right.
Yeah, it's fascinating.
At some point it's going to be, I don't even have to say it, I just think it.
This is part of our vision, Athena longer term, is you shouldn't have to actually vocalize it.
And we've built an internal demo of this.
It's not live for customers, but the way it works is We build something that watches your screen as you work and it screenshots the screen.
And when it identifies things that you should be delegating to your assistant, it automatically adds it to your assistant's task list.
Your assistant then says, oh, Eric would want my help with this, or maybe he'll do this on his own.
And that creates the reinforcement learning effectively to tune the model.
To pull things off of your screen, you don't have to vocalize.
And so the person who built this internally has been using it.
The majority of his delegations are now machine generated.
He's not talking.
He's just working and the machine is magically pulling tasks and putting on his assistance plate.
It'll take a while to bring that to market and fruition, but that's the future.
Relatedly, there should also be a version where it's like you see in Slack that it's someone's birthday or someone has a baby or something, and it suggests hey, do you want to get this person this specific gift or something?
Yeah, I think this is a place where we're thinking a lot about the human-machine merger and how we get the best of both.
And that's really the vision.
Athena is like the best human assistant, the best AI, wrapped into one combined product that's seamless.
And humans obviously have human touch and good UX, but what machines can do is remember everything and be super proactive.
So it can look through every email, every calendar and remind you to do things that you would not have thought to do otherwise.
One thing you've always been fascinated about is sort of international labor, labor arbitrage.
What is the right way of thinking about what people in say the Philippines can do or can't do versus assistance in the US?
Because obviously there's a huge cost savings.
What are stuff that you keep in that cost savings or stuff that you don't keep?
What's the right way of thinking about it?
I mean, America's strength is entrepreneurship, capital, innovation, technology.
And the more you can leverage someone to do back office tasks, the more you can spend on technology product et cetera.
So I think the thing Athena focuses on is executive assistant, someone who can do all of this admin.
But people are using global talent for all sorts of things, for legal medical, all of the above, yeah.
So, on the finance thing, i'm curious because i don't leverage mine there.
What are the ways that people could get leverage from?
This is not because, are you, are you still interfacing with the accountants or are they?
Yeah, what is the right way of thinking about?
Yeah, so the first thing i'd recommend if uh, you're getting an assistant uh, is to have them help you save money.
Uh, if you have a big budget not a big deal, but the first project can be hey, help pay for your salary.
By looking through all my subscriptions, finding things to save me money, find me refunds.
So that's just kind of like a cost-saving bucket.
Then there's admin paying bills.
And then there's coordination, which is what you're talking about, basically being a PM.
So coordinating, you know the tax attorney asks for something from the accountant and there's a bunch of docs and it's just moving paperwork between uh systems.
Um, at enough scale and complexity that becomes effectively a full-time job and obviously you need someone you truly trust uh to go deep with.
And we kind of recommend that you build this trust over time and you know you give email and calendar access at first and bank account later.
But as you earn that trust, then the more access you give effectively, the more leverage you get.
Yeah, the um Yes, very interesting.
And in terms of, say more about what it's been like to scale this company where you have, and you know, you dealt with this thumbtack too a little bit in terms of just workforces in different areas and how you think about culture between them and... yeah kind of what are the the challenges or what's really important to get right yeah um yeah i mean we we look for cultures that have a strong affinity uh to american culture uh you know philippines has long history with america they like know american pop culture and sports better than i do yeah um and then they have a very strong work ethic and uh it's a caretaking um culture so there's lots of nurses and one of the reasons we picked it for assistance is being an executive assistant is really taking care of someone yeah it's like their full-time job is to make your life better is to take things off your plate to help you be successful and i think one of the barriers for some people to get an assistant is it feels indulgent it's like do i should i really have someone who's just taking care of me um but the way i flip that around is you not delegating you not giving leverage is holding you back but it's actually preventing you from creating a job for someone who's excited to help you yeah and for the people on our team like they could work with the ceo they get to see behind this exciting startup that is a totally different life than they live and for them that is a cool exciting life-changing thing yeah One thing that I think people should be using assistance more for is not only delegation, but also accountability of like, hey, you want to be, you know, exercising this amount or you want to be spending your time doing X, Y, Z, or you want to make sure you, you know, you go to your appointments or something.
Yeah.
Do we have some clients who actually exercise live with their assistants for this reason?
They both have a fitness goal, and so they pull up videos at a set time, and they work out together.
And that's the place where human accountability is a little more powerful than machine accountability.
ChatGPT actually has a feature now where it will automatically ping you on things.
So if you can't afford an assistant, you just tell ChatGPT.
Here's my top five goals.
Ask me how I'm doing every day, log my results and give me feedback.
You can get that for 20 bucks a month.
I've done similar versions of this with human assistants.
I think we may have done this in the past, where I'm like hey, I want to work out meditate, eat clean.
Send me a ping on WhatsApp every day and I'll just reply yes no yes no, whether I did it and then, at the end of each week, send me a scorecard and compare me to eric or catherine and we can have a little competition with it.
And yeah, helping you, helping you hit your goals, is exactly what they should be doing.
Yeah, and then the other thing i think is uh, an interesting opportunity to get more leverage, because these people are also, you know um, not just operation savvy, but also you know pretty, you know intuitive, you know they go into caring fields.
And so there's also like opportunities for coaching too or, like you know, they're the people that have most context on you and they can give feedback on how you're engaging or, like you know, they can tell you Hey, you're tired today, you know.
Yeah.
Yeah.
It was my first observation when I was in the West Wing.
The assistants who sat next to the president were insane.
They were so good.
They went on to become, like, elected to Congress and amazing people.
But at the end of the day, the president and his advisors would have been meeting with senators and all these people and they would finish the meeting, they would lean back and they would have the assistant come over and they'd just be like what's going on?
And it was more than just... accomplishing things.
This was their closest confidant who saw behind the scenes on everything.
They knew the good and the bad.
They know they'd gotten kicked in the nuts a couple of times that day from different things.
And they're there for them.
And I think that human element is going to remain important for a long time, no matter how good AA gets.
And it's something you should lean into.
We have clients who tell us that yeah, like going through a divorce or a depression and like my assistant's like there for me in a way that others aren't.
And like I can't tell my company or my team about some of these things, but this is the person that's like on the inside with you.
Yeah, totally.
Relatively.
One of the things you've had really interesting insights on over the years is how to spend time.
Think about time management not only in terms of ways to get more of it via delegating, but also you know how to prioritize.
And you know I've learned this from you but you think about goals on a sort of, you know annual quarterly, you know like on different increments.
Well, maybe we could start with LBD and how you think about goal setting in general, and then we can, you know, get a bit deeper.
I mean my wife Catherine and I, who we met as friends, want to, you know, develop this friendship over one of these entrepreneurship dinners.
We read this book called How You Measure Your Life by Clayton Christensen.
And he basically told the story of how a business school professor kids come back at reunions and they're Fortune 500 CEOs, super rich, and their lives are in shambles.
They're divorced, have all these problems.
The kids don't talk to them, going to jail.
And he's like the rigor they apply to their businesses.
The quarterly reviews, the metrics, were completely absent from their life.
And his point was how do you want to measure your life?
And catherine, i read this book and we were just friends at the time, but we're both like i want to be on your life board directors.
Let's freaking do that.
And so we just started tradition a decade ago.
Every quarter we get together, we fill out a survey in our relationship uh, strengths and weaknesses, kind of squat analysis, geeky stuff and then we talk about like what can we improve uh, what we do better and like anything, if you, the more you invest, the better it gets totally.
And Yeah, I think that's a key point, because some people are turned off by sort of like quantification, like they want their relationship to be placed like you know, relax or turn off or something.
And I think it's less that you have to, like you know, quantify every element of it and more just that you want to.
You don't want to let the lack of quantification mean that you're not prioritizing it.
And so this is just an exercise to make sure that you're actually just like keeping accountable to how you want to be.
Exactly.
It's be purposeful, get the thing you want.
If you're a geek like us, then you measure it and you track everything.
And if you just want to go have like a date and drink wine and talk about your relationship, that works too.
I think it's just people prioritize fitness or their work, but they never think about how do I prioritize my relationship?
Like what's the, what's the fitness or the workout or the yoga equivalent for my relationship?
Having been in many goal setting sessions with you, one of the things i think that you intuitively understand or have learned um and are often instilling in others is this idea of um Like when people set goals.
They set a lot of goals and they don't sort of think about hey, what is the one that makes everything else much easier?
And you know what is the one thing that if we did would be a great year, a great quarter, whatever it is.
Who sets too many goals?
You know, me a little bit.
But, yeah.
Yeah, I think my view is there's a power law in everything and power law in business, power law in venture, power law in your life.
And there's typically one thing every month or quarter that, if you accomplish, is worth more than everything else combined.
And figuring out what that one thing is, uh, is what you should do.
Figure that thing out and then go all in on that.
And not to say that having other goals isn't worthwhile.
But if you haven't identified the one thing and gone all in to make that happen, then I think it's not optimized.
I think it's also easier to kind of procrastinate on the most important thing in your life by having a long list.
And you do a bunch of different things, but there's that one thing.
It's find your partner.
It's start the business.
It's fix my health.
That really is more foundational than everything else.
So, to that end um, i'm curious if you could share more.
You know frameworks or principles you live by in terms of time like, for example, i believe you put you try to stack meetings in, you know, in a day or in as few days as possible, or something.
What are certain sort of frameworks that are important for you in terms of time energy, you know, i mean A high level.
Brian Johnson wants to break the chains of biology or longevity.
I want to break the chains of time.
And, you know, the question I ask myself is like, what's the most valuable asset in the world?
It's not gold or Bitcoin or Nvidia clusters.
It's time.
We can always raise another round or do another trade, but you can't raise another decade.
And so if time is the primary asset and it's more foundational than everything else, we should focus on owning that and controlling it.
And so this means different things for different people.
If you are in hardcore scale mode, that may mean half-hour meetings for 14 hours a day, where you are just grinding out interviews and doing things that only you can do as a founder.
Or it may mean clearing your schedule and having time to dream about the future of the product or big deals.
And I think you just have to know what stage of the business you're in and then design your calendar purposefully around that.
And if you look back on the last month and the calendar does not reflect your highest goals then uh, you're not doing it right.
Yeah, i remember uh, keith raboy shared with me this idea of like, at the end of every week, do a calendar audit of the past week, like what are the meetings you had that you wish you wouldn't have, and then just look at the next.
I mean, this is a place uh, you know, athena systems can do this proactively for you, but there's a place that ai is obviously going to automate and it will be very powerful, or it's at the end of it.
Each week it just tells you here's what you prioritized.
Are those actually your goals?
Yeah, if not, then next week we should adjust those things.
Yeah, I'm curious for your interpretation of meetings.
Some people are like, you know, I want to have as few meetings as possible.
Meeting's not the most efficient.
I'd rather do everything async.
What is your kind of sort of thinking between async and synchronous?
I mean, Naval has a good line that's like, a phone call's better than a meeting.
A voice note is better than a call.
A text is better than a voice note.
I think in general that's true, and...
There's this.
It's almost like a generational thing, where I feel like you're in this a little bit of like there's a reluctance to call people on the phone.
And it's just, we do everything, text and email, but calling people is super effective.
It's really high bandwidth.
You can figure shit out in five minutes.
And so I personally try to minimize meetings and then do more picking up the phone and talking to someone for five minutes.
When I'm in more chairman mode, then I prioritize as few meetings as possible and voice notes.
And what I request is voice notes out and text message back, because listening to voice notes is slow.
It's assault, as Mark entries.
Yeah.
Exactly.
Yeah.
Yeah, it is interesting.
One of my favorite self-help books is the Seven Effective Habits of How to Effective People.
And one of their you know principles maxims is this idea of like efficiency with when it comes to achieving you know tasks, or accomplishing tasks, but effectiveness when it comes to people.
And so, you know, the efficient path might not be the effective path because you might...
You sort of save some time on the front end but you might, you know, accrue sort of a debt on the back end.
And yeah, it might be efficient to just send a text or something but, you know, keeping the dynamic.
Yeah, phone calls are obviously underrated.
Yeah, that's true of remote cultures too.
Like remote cultures build up debt of just the lack of bandwidth.
And so if you are in a remote culture, you should get together every couple of months for a few days in person.
Absolutely.
How do you think about how when founders are asking for advice, like how should I spend time?
Like what's most important?
Like what frameworks are helpful for founders about thinking about?
Obviously, there's a million things they could be doing.
There's not enough time in the day for, you know, even a fraction of them.
What are the most important ways to get right?
Whether it's your time at Thumbtack or Yeah, I mean it's build your product, use these customers, raise capital, build your team.
And when founders ask me, like, how to leverage an assistant, what should I be doing?
The way I turn around is like, what's your top two goals for the month?
If it's recruiting, you have to be closing candidates, but you don't need to be sourcing all of the emails.
You could pull up a voice note and say, here's a template I want you to reach out to.
Let me go through my contacts.
Here's 20 people.
Send an outreach email asking them for suggestions for this role.
You know, if your goal is to raise capital, your assistant could help project manage the process of all of that.
And so you know, step one is you set your goals and then you break them down into subtasks and your assistant won't be able to run the fundraise but can run components of it.
And your job is just to decompose things into the... smallest part that you can hand off maybe you should have some sort of like forward deployed uh you know sort of thing of it's it's not just the assistant but it's also someone that helps you like really get the most leverage out of it and watches you know your your activity one of our learnings from this business when we first started it we were like we're just going to hire the best assistants match them with clients and boom amazing but we matched the first five assistants and every single client said the same thing How do I delegate calendar?
How do I delegate inbox?
And so it became clear we needed to invest more in actually teaching the clients how to delegate, because that is as much of a constraint as the assistants.
And we've got a few thousand assistants and clients.
And if you look at the best performing assistants at Athena, they work for the best delegators.
It's not a coincidence.
The reason they're the best is because someone has figured out how to export their ideas, decompose projects, create SOPs in a way that helps the assistant fly, and the more mediocre delegators struggle with that and need more training.
Yeah.
One thing that you've been phenomenal at is hiring executives.
What do you think that you do differently, or what are the principles or frameworks that really guide your exact hiring process?
I mean.
One thing that is obvious as you hire execs is the more senior they go, the better.
They are interviewing almost by definition.
And so when you get to C-suite, they all are really good at interviewing.
And so you actually have to discard the interview more the more senior they go.
And so I use references much more the higher you go.
And then the other thing that I think is interesting, that people should do more of, is I just ask people for their 360 reviews.
Like at their last company, 10 people wrote reviews of them that are honest about their strengths and weaknesses, and I just asked to see it.
And I say, hey, I'll share mine.
You show me yours.
I actually think this would be a cool kind of reference startup where you could like ping the LLM about someone versus pinging their references.
So I try to get to more ground truth on the person versus –
The UX of an interview is just going to be pretty good when you get to the senior level.
What's most important when you're doing reference checks?
What's the way to get the most signal out of them?
I mean, what I often tell people is, hey, I'm probably going to hire this person.
And... now tell me all the things you don't like about them, or things that they could be better at.
Because people are so biased to just tell you all the good things.
You have to get them to see it as a safe place to share strengths and weaknesses, and just do enough references until they start to sound the same.
And once they start to sound the same, then you've got a signal.
One question I like to ask is what skill sets would be really important to complement this person with.
Which is another way of just saying, what are they bad at?
What's really important?
Or one of my favorite questions is if this didn't work out in six months or a year, why would that be?
Yeah, and i mean the best way to source talent.
Um, i just hired an executive recently.
Just ask the people that you respect the most.
They have the highest standards.
Who's the best person?
So like, here's the three people who have the highest standards in this role, i ask them for the two or three best people and i go try to hire one of them.
And that is the like speed, rapid way to hire an exec.
You know, using an exec recruiter, you spend three months, you get all this cold leads, but going through a network of high bar people is super efficient.
There's some maxim that almost like, half of executives you know don't work out within like uh, you know, 12 to 24 months.
Checks out yeah, why is that?
I think it's this it's difficult to judge.
Uh, the interview process is not representative of the work they're doing, and that's ultimately what's broken about interviewing is interviewing should be someone doing the work they're going to do.
I think it was like Weebly back in the day would actually have execs come work for two weeks to trial before they ever hired.
That's difficult to pull off because people have other jobs.
But I do think something like that makes a lot of sense.
Your interview process is just kind of irrelevant compared to what the work they're doing in lots of cases.
Yeah, and Keith has this maxim that that's like you're not going to get 100 hiring.
In the same way, you're not going to get 100 investing.
And if, you know, You also want to avoid the trap of not taking enough risk or moving too slow.
Yeah, and as long as you cut your losses quickly, it's okay.
If you don't cut losses, then you compound a hole.
That's where it's painful.
The other thing I'd say is more useful for basically all interview process is project-based work.
Yeah so, just like you know, hiring a c-suite for one prod uh, one part of the team, i just tell them what the pain points in the org are and what i want to fix, and i'm like come up with a plan.
Yeah, how would you fix this?
Yeah like, if you, we hire you, you're then going to do it.
Yeah, and that sort of practical work is more useful.
Yeah, that's interesting.
What um?
Going back to other sort of founder principles, what is your stance on?
Um transparency with the company?
What's information that's helpful, maybe going back to Thumbtack days?
What's helpful for the company employees to know?
What are principles that guide how much you share?
Yeah, I mean, default transparency is obviously the best, but there's obviously some lines.
At Thumbtack.
There was a moment you may remember this a decade ago where I woke up And I had a message from someone on our team in the Philippines and it said Thumbtack does not exist on the internet.
I was like, what?
And I went to Google.
You type in Thumbtack, and nothing shows up.
And we basically received the death penalty from Google.
There was a misunderstanding.
They thought we'd done something wrong.
But they eliminated us from the internet.
And so our traffic went to zero.
And our revenue went to zero. and i remember waking up and like i go to the office and there's a class of 25 new thumbtackers who is their first day i'm supposed to do the onboarding with them there's a journalist like walking around outside trying to get a quote and you know that's one of those times where you can't share everything and so uh you want to ultimately be transparent but if i just walked into a new class and say hey the business might be dead uh it's not gonna work and so you have to kind of get a handle the situation uh you know the people who need to know it know it and then once there's a plan and a solution in place then the whole company uh is told yeah that makes sense um at thumbtack you were a non-ceo co-founder and you lasted you know a decade or almost a decade and you're still on the board of course I feel like it's pretty rare when I think about co-founding teams that it feels like the non-CEO, especially if you're not a CTO, usually that doesn't last over five years or something.
I'm curious what's really important to get right in co-founder relationships, or how you think about advising companies that you invest in.
I heard Sir Michael at Sequoia say something that was like, there's only one founder.
And it was at, he said it at a founder event.
And I was like, that's rude.
There's lots of co-founders here.
And now, a decade later, I'm like of course there is only one co-founder.
That goes the distance, because ultimately, as you scale the org, it only makes sense to have one person on top.
Um, so I think that's just the reality.
And, uh, You know, it's good to know that going into starting a business.
In terms of who to pick, my advice is you pick someone you want to get married to.
And you're going to have all the same relationship issues you have with a partner.
You know, no makeup sex, but it's still like, yeah, there's highs, lows.
And you want someone that ultimately you really deeply trust because there's going to be stress.
Yeah. but as long as you trust the foundation, then you got a good thing to build on.
I'd say you know, one of the biggest challenges I don't know if I called a mistake at Thumbtack, because I love my founders, but it's something I wouldn't recommend others do is we had four co-founders and one was technical.
He left after like two years and then the other three were non-technical.
This is like the most idiotic way to start a technology business, but we had no idea what we were doing and it worked out.
And how did you divide and conquer between those three non-technical?
Uh, we just kind of jumped on things as like whoever was good at something, but it was no clear executive yeah, and i think that's uh, you know it's not recommended because there's like it's obvious how that could create tension.
We worked through it but um, that's why it's non non-standard.
Yeah, not best practice right but um, i'm going back to the original story because i remember there's this uh, you got into gsb and you were going to grad school but you, you know, had your buddies from college and you were thinking of starting this, this business, which wasn't even like a personal pain point.
You just thought it'd be a good business and you uh, emailed the.
You know you let the gsb people know you weren't going to accept it and they sent you back this very moralizing email of how you're making the biggest mistake in your life um, et cetera.
You know it turned out.
But how do you pretty good decision.
How did you at the time think about getting enough conviction to take the leap and do it?
It was scary.
I got into, you know, this good school.
Seemed like that was a safe bet.
I knew I wanted to start a business.
And, you know, if I went to business school, I knew that I'd have all this debt.
I probably might need to get a nice paying job afterwards.
And if I was gonna go for it, I should probably just go for it.
But, yeah, when the dean sent me that email, I was like, this is the biggest mistake of your life.
He said something like startups will come and go, but you can only come to Stanford once or something.
This is a once-in-a-lifetime opportunity.
I never responded and I have it as an email in my save that I'm just going to respond to whenever some tech goes public and be like I made the right decision.
And you know i have nothing against this guy, he's just doing his job, but it's good to have a little uh chips on your shoulder.
Yeah, totally okay.
So there's eas and then their chief of staffs.
How should we think about sort of the, the difference there and what's really important to get right in chief staff?
It's a role that everyone, in addition to a, wishes they they had um, but seems hard to find the right person.
Yeah, there's no formal definition.
I think it's something that an ea is typically more administrative and taking things off your plate, and uh chief of staff is more offensive and that's the type of person who can follow you into meetings you could deploy to hey like, actually take this meeting for me, or hey, this problem came up uh today, go figure out how to solve it.
And so a chief of staff typically has the capabilities to become a founder themselves.
And the only reason they take the job as chief of staff is so they can see what it's like to be a founder, so they can go off to do it.
So you kind of get people who do more tours of duty and you get super high capability, but you don't get the same longevity as an assistant.
Yeah.
What have you looked for in Chief of Staff?
Or what's sort of the right.
You know, there's sort of this tension between, you know, getting someone younger who's, you know, definitely initially going to do it for a couple of years and is more ambitious, versus someone who's been more seasoned but maybe not as high slope, or something.
How do you think about it?
The way I break it down is assistant, you find someone you want to go a decade with.
The intimacy and the compounding of that relationship is super important.
And so you go deep, and that means you probably don't find a founder because they're not going to be excited to do this.
It's someone who's much more of a caretaker and is excited to be number two.
And then a chief of staff.
I do pure slope where you know the person is going to move on in a couple years but they have yeah, they could start a business, but instead you get them by your side to help solve problems.
Totally.
And there are people you know, like lonsdale maybe like a lot or something, who have, you know, chief staff for like a year or two and then they start a company, then they invest in them and they build kind of this reputation for for doing, and then they have sort of these, like you know um, alumni almost achieve staff just kind of.
You know.
Peter thiel's just kind of further yeah, bezos has this, someone follows him around, that goes to every meeting and yeah, it's cool.
Yeah, Let's talk about some people who get an enormous amount done.
And I'm curious, what are lessons that we can draw from them?
Whether it's someone like Lonsdale, whether it's someone like Elon, whether it's someone like Sam Altman, who are folks that you've particularly learned something from, even just watching from afar of like.
How do they build their world?
How do they operate?
I'll just say one for someone like Lonsdale.
Teal has done this really well.
They sort of compound these certain talent networks.
So you know, whether it's like Stanford Review or just Stanford in general, they're often hiring people from there and then involved in sort of these talent pipelines.
They've sort of you know created, you know they're deep in the hackathon scene, but they just kind of build this proprietary compounding sort of talent base that they're constantly you know sort of I mean the talent access is part of it.
I think the other thing is there are some people who have just limitless ambition.
You're very much this way of like, well, what if I could do 10 times more things?
And I think lots of people just think that's impossible.
But it's not.
It is possible.
And with delegation and empowerment, you can just keep compounding bigger and bigger scale.
The other thing that's interesting that we've seen from working with these like power delegators is people assume that people of great power or wealth or resources can afford this team.
And then that is why they have this ambition.
But we've actually seen the opposite is the case is, as people get more leverage with assistant, their ambition increases.
Yeah.
And it's difficult to have big ambition if you're just weighed down by DMV forms and passports.
But once that's off your plate, then you raise your sights and you can be more ambitious.
And then you go from assistant to chief of staff and you just keep leveling up until you're Lonsdale or the president.
I think another thing I've admired about some of these people is they.
You know, they hold remarkably few grudges.
Like, you know, apparently, you know, Peter Thiel, like, kicked Elon out of PayPal or something.
Or you know, like a lot of these people have had beefs you know decades ago, and yet he ended up funding his next company.
And so people have very short memories if someone you know mistreats them or they make a mistake or something.
They're quick to reconcile and just do business again over, yeah.
Yeah, I mean, look what President Vance said about President Trump before they were partners.
Yeah yeah, i think there's trump's actually quite forgiving or, you know, a lot of people say a lot of bad things about him and he'll continue to work with them as long as they change their mind.
Yeah, i think there's just a desire to win uh, at all costs.
And uh yeah, grudges are not helpful.
Yeah, even trump and elon right yeah, getting into it.
And you know reconciling yeah, it's uh, you know tbd where it stands by the time this comes out.
And then there are some people who seem to have pretty like uh, you know, bill gates has like, you know, pretty big team, pretty big operation um, But then it seemed like Bezos and Elon maybe have like pretty lean.
Yeah, I'm curious how you think about sort of.
I mean, Elon's the one that makes no sense.
He claims to not have an assistant and to be like scheduling stuff.
There's a story of Bill Gates being like trying to schedule a meeting with Elon.
He's like, connect me with your assistant.
And Elon's like, no, I have my assistant.
I hardly believe it, but Elon's just insane, so maybe he is that way.
I think most normal humans, if you want to get leverage, you have to delegate.
One of the cool personal teams I saw is this guy who's a billionaire.
He runs this hedge fund, and he has a team of 40.
He has eight personal executive assistants.
All of the executive assistants graduate from Princeton, insanely high bar.
And I was asking this woman who managed the EA team like how do you decide what to prioritize your team on?
And she's like if my team can spend one day saving my principal one minute, it's well worth our time.
And I'm like, that is so next level.
And definitely like that's something I would love to aspire to, but it's just, you know the the billionaire budget yeah, it's pretty funny.
Um also, just in terms of prioritization like um, you know we're hiring you know assistants here and someone's saying oh, you know, do you want them to be in all meetings with you?
And i was like well, if they're in meetings with me, then they're not working like i want them to be.
Like you know finding ways to give me leverage and take things off my plate.
I mean, this is one of our visions at Athena is that you can have digital assistants that listen to you and work with you and are connected to your Zoom and your inbox and your calendar and can be mining all of that digital exhaust for things your assistant should work on.
And so, I mean, your assistant can't possibly sit in every meeting if they're going to do anything.
But if the digital, the machine assistants are surveying it and pulling things out.
That's a pretty cool combination.
Yeah, think it's interesting to look at how people build out their universe like, for example, you know, mark and ben funnel everything through async and z and are all in an acz, and of course have you know other intellectual or philanthropic interests, but mostly it's like consolidated, whereas someone like peter thiel has this um he sort of fragments it a bit more.
You know, like um Founders Fund, but then several other funds, other companies, all sorts of initiatives that are somewhat collaborative but independent.
And he sits on top, but also it seems like he lets them, he's not like CEO of them.
And he's got this sort of talent network that he's worked with for a long time.
That kind of goes in almost boomerangs across the universe.
Lonsdale feels like he's more hands.
He's got the ABC universe, but then his other initiative, he's like quick to institutionalize something, whether it's like a think tank or like you know.
It's no coincidence that you know Peter Thiel would do the sort of Thiel Fellowship and Lonsdale would create a university or something.
Thiel is almost like early to stuff.
He creates a format for something, a template.
You know he does the hard work of sort of.
You know field building intellect or, like you know, doing something that's in a controversial space where it's longevity, or charter cities, or you know higher education.
And then, you know, people like Lonsdale institutionalize it to some degree.
And then yeah, Elon you know it's been described also has this like SWAT team.
You know of people that help him from from company to company.
And he's just able to recruit, you know, world class people to to lead these efforts.
Yeah.
I think it comes... It's like, what's the right org structure?
There's actually no right org structure.
It's what's the right org structure for you as a founder?
And, you know, Marc Andreessen and Ben Horowitz are company builders.
And so they're building their leverage like a company.
The A16Z is a company.
Not that Peter Thiel is not an entrepreneur, but he's more of a philosopher today.
And so his uh system is more like a philosopher it's all these kind of wild and crazy ideas, uh.
And so i think you know, jensen huang has like 46 direct reports or something, which is absolutely insane, but it works for him, and so i think you just have to know what your style is and then you build it for you totally.
And someone like you know, sam allman, is like a deal maker and a fundraiser and a talent identifier, you know.
And so he's able to like i remember he was at yc and he was talking to my one of my friends about sort of this universal basic income company.
My friend didn't end up doing it, but i was like oh, that's interesting, why is?
Why is he even doing that?
He's like focused on yc.
He's like he has a knack for for good ideas.
He's a knack and this person was like 22.
He has a knack for, you know, uh high slope talent and he has a superpower around raising money.
Yeah, I mean one of the things that I think new founders or at least me as a new founder was like okay, what are my weaknesses and how do I get better at them?
But then a second time founder is like, forgive all of my weaknesses.
I'm just not going to try.
I'm just going to be really good at my strengths and I'm going to hire other people to do all the things I'm not good at.
And that is way more effective.
Yeah, totally the um.
There used to be this sort of skepticism of like hey, you can't really and this really is actually, you can't really incubate company like this.
The ceo has to be the co-founder, the founder, they have to drive it to.
Where do you stand on on kind of that that debate?
I think the biggest companies aren't incubated because the biggest companies have a founder who is monomaniacal from the beginning and compounds it for 50 years.
Yeah, totally.
And that's not incubation.
Incubation is kind of, let me try a bunch of things.
It's not this monomaniacal power law commitment.
So if you're just trying to build a trillion dollar business, I think that's not the way to do it.
Yeah, but look, if you like, you know, we have a mutual friend who likes to remain anonymous, who incubates lots of companies and he launches four companies a year and he loves doing it and he's gonna make a ton of money doing it and that's just his style.
He's not gonna probably have trillion dollar businesses, but he's gonna have 50, you know, 100 million dollar businesses, which is still incredible, right?
Yeah, i think one bull case is more of it's like uh, breeding.
Like you know, Sam Altman in some sense incubated open AI and that it wasn't the main thing he was working on.
But then, once he identified that it could be, you know this massive opportunity, then went all in with it.
Yeah, I mean, it's more like a venture portfolio.
And you know, there's probably a bunch of stuff Peter Thiel has done that we don't even remember, like seasteading and things like that, because they just disappear into the ether and then things that work compound.
And so I mean, if you have the resources to launch 10 new things and then just double down on the one thing that's big every year, that's a cool, cool approach.
Right a decade ago, mark andreessen wrote this blog post on productivity yeah, and they were asking him how you think about you know meetings scheduling, whatever and he said you know what, i try not to schedule things in advance because i don't know how i'll feel, you know, next week and i want to kind of want to do things like in flow, and so when you know people are trying to get my time, What I typically say is like call me right now or feel free to check in next week and we'll see how I feel.
And it kind of is like better aligned with sort of the flow state.
I mean, that's the ultimate flex.
It's like, if you can pull that off, that is definitely the ultimate way to live.
You just work on whatever you want, the world opens up to you.
You call.
Obviously it's hard for most mere mortals to pull off, but yeah, if you can get to that level, that is the dream, right.
So then I was for certain meetings where people were cold, reaching out or whatever.
I was kind of try it's.
It's like um, i always anticipate that in a few more days i'll be like busier than i am or something, or i'll have you, whereas like right now yeah, i got time, give me a call um, but so i i tried that a little bit.
And then i mark did a follow-up interview uh, where someone asked him about that sure um um, and he's like oh, you know, that didn't work.
Like i, i tried, but that didn't work.
Now i'm just scheduled just back to back all day long and i was like oh, god damn it.
But he's also mastered multitasking.
I mean I think people.
Just the thing I think you can learn from Mark and other people is just challenge the defaults occasionally.
And if you're in back-to-back meetings all the time, try this other system and see if it works.
I think most people just go with the flow.
I think the other thing is most people aren't vicious enough at saying no.
Yeah, and just being super hardcore is like is that conference you're going to matter?
Is that random get to know you chat mean anything?
Yeah, i think you just say no to most things.
Um, you know i've back in the uber versus lyft.
Uh, really scaling war days.
I remember emailing logan a question, probably to come to one of our dinners, and he just responded war mode.
And I love that.
And I'm like, well, most people should actually be in war mode like 90% of the time.
And that same, yeah, hardcore-ness is just like the right way to operate.
Yeah, what have you learned in your extensive founder career about managing your own psychology, dealing with stress, dealing with the cognitive dissonance of you know having to present externally like things are amazing, even when you know you're concerned about google.
You know taking out your business um what, um?
What advice might you have for others in terms of cultivating this?
Uh Yeah man, I think it's like a cold plunge or something.
It's just shock therapy and eventually it's just like you're bathing in existential fear all the time and you're like whatever, let's bring it on.
Totally.
I don't think there's much other than knowing that it's going to happen.
There's going to be tons of ups and downs.
I think one of the clear lessons from thumbtack, which is now scaled and and done so well, was that like there was lots of near misses where we almost died, times where we thought it wasn't going to work, and it's like you just got to stay in the game yeah, and if you can stay in the game, you can eventually win.
Yeah, and i think thumbtack was very good at staying the game so that we can eventually win Yeah.
It's funny.
There's like degrees of panic in the beginning.
You know, you're getting your feet wet.
It's like, oh, my God, someone said something mean about me on the Internet.
And then it's like, oh, my God, someone wants to like leave my company.
And then it's like, oh, my God, we're going to, you know, we might die.
We have six months of payroll.
Then it's like, oh, my shit, we're going to get sued.
Yeah.
It's like, you know.
Well, it's like the first time you get sued or you're worried about getting sued, and then eventually you have a board meeting and there's just a list of lawsuits and it's just you review them quarterly and it's just like that's actually what success is.
It's like, you're going to have that stuff constantly and it becomes...
Yeah, just part of business.
Yeah.
And you just keep building up more capacity to handle these things.
Yeah, and it's where I think co-founders are the best.
It's the people you can be totally open with and be like, well, that situation's f-ed up.
And someone you can trust and be on the ups and downs with.
Let's go to Athena and let's go where we started, which is sort of the intersection between humans and AI.
How have you thought about building Athena given sort of developments in AI?
What does that mean for you?
Athena started fully bootstrapped, human-only, scaled to 1,000 people, no outside capital.
And then we had this AI moment a few years ago and it was clear we could make a big ai play and this could become a generational business, or we could get railroaded by ai, and so only one option there is go big.
And our vision here is this uh, is you take the best of a human investment machine, wrap it into one unified product, and what the machine does will increase over time, just like a self-driving car, and so the humans, the ux it's on top, It will become more.
The human assistant will focus more on project management and high-level work and really be that caretaker, that empathy, that partner.
And the machine will increasingly do the more mechanical, administrative stuff.
And...
When you get into a Tesla, Elon made them with steering wheels so you could drive them, because they don't drive themselves.
When you started.
But every time you get in the car, you're actually teaching the machine how to drive.
And these models don't generalize well.
You have to bring edge cases under distribution.
And so every time you drive, the the model gets more powerful.
And the same is true in executive assistant.
Our humans are driving, they're doing the tasks, but we're building machine models that are being improved by the way they act.
And so the more your assistant does tasks for you, the more our models will improve, and that will allow the human to upgrade what they work on to more high leverage stuff.
Yeah um, that's exciting.
So what?
What else uh can you share about plugs for the company or things to watch out for or for people who you know want to get assistance?
Yeah look uh, i just say if you don't have an assistant, you are the assistant step one.
Uh, if you're starting a business, you should hire assistant and if you've got 20 bucks a month, use chat gpt.
Yeah, if you've got, you know, 10 bucks an hour, go on to upwork and hire someone yourself.
If you hire someone yourself, I would say my main recommendation is you need to interview a lot of people.
You know Athena, we have 50000 assistants apply per month and we put them through a huge battery of tests and we hire like one in 300.
So if you're going to hire on yourself, make sure you interview not 10, but probably like 50 people.
If you have the resources for 3000 a month, then you should work with a company like Athena or who can recruit train, manage and teach you how to delegate.
And then when you have the resources for an in-person assistant 100, 150K a year you should do that as well.
And then ultimately, when you get later stage, you have a chief of staff in-person assistant and a fleet of Athena assistants in the cloud.
Yeah, that's a great overview.
Well, let's wrap on that.
Awesome.
Thanks for listening to this episode of the A16Z Podcast.
If you liked this episode, be sure to like comment subscribe, leave us a rating or review and share it with your friends and family.
For more episodes, go to YouTube, Apple Podcasts, and Spotify.
Follow us on X at A16Z and subscribe to our Substack at a16z.substack.com.
Thanks again for listening, and I'll see you in the next episode.
Please see a16z.com forward slash disclosures.
