How the Best CEOs Delegate

Brian Johnson wants to break the chains of biology. I wanna 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 marriage 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 of Nova Scotia to have a half dozen assistants, and that cost you half $1,000,000. Now with a company like Athena, for $3,000 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 Bumtack 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 shaped 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 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 a EA and 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, 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 someone else who was like, the president should have way better information than me, and yet they're reading Politico too. Like, they're reading the same. Mhmm. This is like another example of it, which is democratization where a White House have amazing assistance, but thanks to Athena and technology, at some point, everyone will have a certain block.

Exactly. A couple decades ago, you had to beat Marc Andreessen or Vino de Cosva to have a half dozen assistants, and that cost you half $1,000,000. Now, with a company like Athena, for $3,000 a month, you can have your own assistant. And then with AI, yeah, it's gonna become ubiquitous. There's gonna 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? Remember my friend started Clara, you know, a decade ago, which is trying to be AI assistants of effective absences well before a lot of the innovation. Yeah. 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 gonna 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. Then over time, it becomes more autonomous, and the same thing is gonna happen with assistance.

My view here for founders is if you don't have an assistant, you are the assistant, and you don't wanna be the assistant. And so no matter your budget, you should first start by learning to delegate. Yeah. And if you only got $20 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 6 figures.

And if you're legendary budget, then you've got a suite of assistants and chief of staffs following you around.

Yeah. So, I've had an ETHEA 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 Corkos has a bunch of assistants as well. What else do people get leverage on Yep.

Or delegate that maybe is not obvious?

So first, you start by taking the pain off of your 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? Yeah.

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 things 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. Yeah. And then Marnie's helping plan our wedding, and now Marnie helps us with our kids.

And so, start small, and then you just kinda compound these things.

Yeah. But even in that example, say more about how did she know who to reach out to or

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 it similar stages, or similar number of employees, and literally write an algorithm for how you find the right people. And then you get feedback on whether it worked or not. And once the algorithm's 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 systems, how do you differentiate like, how do you sort of delegate across the team?

Yeah. I mean, start with one.

Yeah.

And then, like, any team you specialize. And so, I just had one that did everything as a generalist, and now, have a half dozen, which I know sounds crazy. Yeah. But each one specializes in different things. One is on work.

One is on home. One is on kids, family, travel, finances. Yeah. And that specialization is helpful because the finance person is just thinking about balance sheet, you know, sending wires, all that sort of stuff. And then I have a chief of staff who sits on top who distributes work Yeah.

Across all of them.

What are other principles like, I love this, delegated by algorithm, not by task. What are other principles or frameworks that are really important or non obvious to get the most out of an SSM?

Yeah. The cardinal sin of delegation is that it will be faster or better to do it myself. Yeah. 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. Yeah. And 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. Yeah.

So 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, twelve 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 kinda 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 and 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 delay 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, in between lunch, in the Uber. 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 Yeah.

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, then you get to the end of the day, and you're like, I have a 100 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 gonna 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. No. 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, he's 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 assistant's 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 wanna Yep. 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 you can look through every email, every calendar, and remind you to do things that you would not have thought to do otherwise. Yeah.

One thing you've always been fascinated about is sort of international labor, some call it 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? Like, 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?

Yeah. 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, etcetera. 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 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? Are you are you still interfacing with with the accountants, or are they yeah. What is the right way of thinking about it?

Yeah. So I the first thing I'd recommend if you're getting an assistant is to have them help you save money. Yeah. 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. Yeah. And then there's coordination, which is what you're talking about, basically, being a PM. So coordinating, you know, the tax attorney Yeah.

Ask for something from the accountant, and there's a bunch of docs, and it's just moving paperwork between

Yeah.

Systems. Add enough scale and complexity, that becomes effectively a full time job. And obviously, need someone you truly trust Yeah. To go deep with, and we kinda recommend that you build this trust over time. And, you know, you get 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 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 thumb 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 what's really important to get right.

Yeah. Yeah. I mean, we we look for cultures that have a strong affinity to American culture. You know, Philippines has a long history with America. They, like, know American pop culture and sports better than I do.

Yeah.

And then they have a very strong work ethic, and it's a caretaking 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.

Yeah. It's like, do I should I really have someone who's just taking care of me? 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've worked with a CEO.

They get to see behind this exciting start up that is a totally different life than they 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.

Mhmm.

Of like, hey, you wanna be, you know, exercising this amount, or you wanna be spending your time doing x y z, or you wanna 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? Like, they both have a fitness goal, and so they pull up videos at a set time, and they work out together.

Yeah.

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 Yeah. 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 a month.

I've done similar versions of this with Human Assistant. I think we may have done this in the past, where I'm like, hey, I wanna work out, meditate, eat 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 Katherine, 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 interesting opportunity to get more leverage because these people are also, you know, not just operationally 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, Mhmm. They're, 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. The Yeah. That 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 Yeah. Amazing people. But at the end of the day, the president and his advisers 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 it was more than just accomplishing things.

Yeah. This was their closest confidant who saw behind the scenes on everything. Yeah. They knew the good and the bad. They know they'd gotten kicked in the nuts a couple times that day from different things, and they're there for them.

Yeah. And I think that human element is gonna remain important for a long time, no matter how good AI gets, and it's something you should lean into. We have Yeah. Clients who tell us that, yeah, like, going through a divorce or Yeah. A depression, and, like, my assistant's, like, there for me Yeah.

In a way that others aren't, and, like, I can't tell my company or my team about some of these things. But it's this is the person that's, like, on the inside with you.

Yeah. Totally. Relatedly, one of the things you've had really interesting insights on over the years is is how to spend time. Think about time management, not not only in terms of ways to get more of it via delegating, but also, you know, how how to prioritize. And, you know, I've I've learned this from from you, but you you think about goals on a sort of, you know, annual, quarterly, you know, like on different increments.

Why don't you maybe maybe we could start with LBD and how how you think about goal goal setting in in general, and then we can, you know, dive a bit deeper.

I mean, my wife, Catherine, and I, who we met as friends, wanna you know, developed 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 Harvard Business School professor, kids come back at reunions, and there are 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 wanna measure your life?

And Catherine and I read this book, and we were just friends at the time, but we're both like, I wanna be on your life board of 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, strengths and weaknesses, kinda squat analysis, geeky stuff. And then we talk about what can we improve, what can we do better.

And like anything, the more you invest, the better Totally. It

And, yeah, think that's a key point. Because some people are turned off by sort of quantification. They want their relationship to be placed, relax or turn off or something. And I think it's less that you have to quantify every element of it, and more just that 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 wanna be.

Exactly. It's be purposeful, get the thing you want. If you're a geek like us, and you measure it, and you track everything. Yeah. And if you just wanna go have like a date and drink wine Yeah.

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 Yeah. Relationship?

Having been in many goal setting sessions with you, one of the things I think that you intuitively understand or or have learned and are often instilling in others is this idea of prioritization. When people say goals, they say 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 the one thing that if we did would be a great year or a great quarter or whatever it is?

Who sets too many goals?

You know, me a little bit. But but

Yeah. I I think my view is just 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, it's worth more than everything else combined. And figuring out what that one thing is 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 a long list. Yeah. 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, I'm curious if you could share more, you know, frameworks or principles you live by in terms of time. Like, for example, I I believe you put you try to stack meetings in, you know, in a day or or in as few days as possible or something. What are what are certain sort of frameworks that are important for you in terms of time, energy, you know, maybe?

High level is that Brian Johnson wants to break the chains of biology or longevity. I wanna 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 for different this means different things for different people. If you're in hardcore scale mode, that may mean half hour meetings for fourteen 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 Yeah.

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 And if you look back on the last month, and the calendar does not reflect your highest goals, then you're not doing it right.

Yeah. I remember 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 week.

I mean, there's a place you know, Athena systems can do this proactively for you, but there's a place that AI is obviously gonna automate Yeah. 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. Those are 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 I wanna have as few meetings as possible. It means it's not the most efficient. I'd rather do everything async.

Yeah. What 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. Yeah.

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 I I what I request is voice notes out and text message back, because listening to voice notes is slow. It's assault as Mark and Tracy. Yeah.

Yeah.

It is interest you know, one of my favorite self help books is the seven effective habits of how it affects people. And one of their, you know, principles at Maxim's 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 and so, you know, the efficient path might not be the effective path because you might sort of save some time on the front end, but you you might, you know, accrue sort of a debt on the on the back end. Yeah. And, yeah, it might be efficient to just send a text or something, but, you know, keeping the dynamic yeah.

Phone calls are obviously under underrated and

Yep. That's true. Remote cultures too. Like, 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 months for a few days in person.

How do you think about how, when founders are asking for advice, like, how how should I spend time? Like, what 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 what are the most important ways to to get right?

Whether it's just time of

thumbtack Yeah. Mean, or look. It's build your product, you see it's customers, raise capital, build And your when founders ask me, like, how to leverage an assistant, what should I be doing? My the way I turn around is, like, what's your top two goals for the If it's recruiting, you have to be closing candidates, 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.

Here's 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 Yeah. Your assistant could help project manage the 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 then 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, you know, sort of thing of it's it's not just the assistant, but it's also someone that helps you Mhmm. 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 gonna hire the best assistants, match them with clients, and boom. Right. 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. Yeah. 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. Yeah. 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 Yeah. Struggle with that and need more training.

Yeah. One one thing that you've been phenomenal at is, whether it's Stunt Tech or Athene, is is hiring executives. What do you think that you do differently, or what what are the principles or frameworks that really guide your sort of exec hiring process?

I mean, one thing that is obvious as you hire execs is the more senior they go, the better they are at 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 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 three sixty 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 you share mine. You show me yours. I actually think this would be a cool kind of reference pro startup where you could, like, ping the LM about someone versus pinging their references.

So I try to get to more ground truth on the person versus the UX of interview is just gonna be pretty good when you get to the senior level.

What's most important in when you're when you're doing reference checks, what are you really you know, what what's the way to get the most signal out of them?

I mean, what I often tell people is, hey, I'm probably gonna hire this person, and now tell me all the things you don't like about them. Yeah. Or things that they could be better at. Yeah. Because if, you know, people are so biased to just tell you all the good things.

You have to get them to to see it as a safe place to share strengths and weaknesses, and, yeah, 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.

Yeah. Well, one question I like to ask is, what skill sets would be really important to compliment this person with? Mhmm. It was another way of just saying, what are they bad? Yeah.

Like, you know, what's really important? Or one of my questions is, if this didn't work out in six months or a year, you know, why would that be?

Yeah. And, I mean, the best way to source talent, I just hired an executive recently, is 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. Yeah.

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 these cold leads, but going through a network of high bar people is Yeah. Super efficient.

There's some maxim that almost, like, half of executives, you know, don't work out within, like, Mhmm. You know, twelve to twenty four months.

Checks out. Yeah.

Why is that?

I think it's just it's difficult to judge 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 gonna do. And 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 Yeah.

And Keith has this maxim that that's like, you're you're not gonna get a 100% hiring in the same way you're not gonna get a 100% investing. And if Yeah. You know, like, you also wanna avoid the, you know, of not the trap of not taking enough risk or moving too slow.

Yeah. And as long as you cut your losses quickly, it's okay. It's well, if you, like, don't cut losses, then you compound a hole, and that's where it's painful. The the other thing I'd say is more useful for, basically, all interview process is project based work. Yeah.

So it's just like, you know, hiring a c suite for one prod one part of the team. I just tell them what the pain points in the org are Yeah. And what I wanna fix, and I'm like, come up with a plan. Yeah. Like, how would you fix this?

Yeah. Like, if you we hire you, you're then gonna

it.

Yeah. And that sort of practical work is more useful.

Yeah. That's really interesting. What going back to other sort of founder principles, what is your stance on transparency with the company? Like, what's information that's helpful? Maybe going back to Thumbtack Days.

What's helpful for the the company to employees to know? Or, like, what what are principles, like, that guide, you know, how much you share?

Yeah. I mean, default transparency is obviously the best, but there's obviously some lines. I there's, you know, 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? Yeah.

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, like, eliminated 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 him. 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 you want to ultimately be transparent. But if I just walked into a new class and say, hey, the business might be dead, It's not gonna work. And so you have to kinda get a handle of the situation, 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 is told.

Yeah. That that that makes sense. At Thumbtack, you were a non CEO cofounder, 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 cofounding teams that it feels like the non CEO, especially if not a CTO, usually doesn't last, you know, over five years or something. Mhmm.

I'm curious what's really important to get right in in cofounder relationships or how you think about advising, you know, companies that you invest in.

Yeah. I mean, I heard sir Michael at Sequoia say something that was like, there's only one founder. Yeah. And it was at he said it at a founder event. And I was like, that's rude.

There's lots of cofounders here. And now a decade later, I'm like, of course, there is only one cofounder that goes a distance because, ultimately, as you scale the org, it only makes sense to have one person on top. Yeah. So I think that's just the reality. And, 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 wanna get married to. Yeah. And you're gonna 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 you really deeply trust because there's gonna be stress and challenges. But as long as you trust the foundation, then you got a good a good thing to build on.

I'd say, you know, one of the biggest 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 nontechnical. This is, the most idiotic way to start a technology business, but we had no idea what we're doing, and, you know, it worked out.

And how did you divide and con and conquer between those three nontechnical?

We just kind of jumped on things. It's like whoever was good at something Yeah.

But it no, like, clear executive.

Yeah. And I think that's, you know, that's not recommended because there's, like it's obvious how that could create tension. We worked through it, but that's why it's non standard. Yeah. Not best practice.

Right.

But, I'm going back to the original story because I remember there's this you got into GSB and you were gonna go to grad school, but you you know, had your buddies from college and you were thinking of starting this business, which wasn't even like a personal pain point. You just thought it'd be a good business. And you emailed the, you know, you let the GSB people know you weren't going to accept it, and and they send you back this very moralizing email of how you're making the biggest mistake in your life.

Mhmm.

It it, etcetera. You know, it turned out pretty good. But how do you pretty good decision. How did you, at the time, think about getting enough conviction to 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, was like, this is biggest mistake of your life. And he said something like, can 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 a email in my this save that I'm just gonna 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 chips on your shoulder.

Yeah. Totally. Okay. So there's EAs and then there's chief chief of staffs. Mhmm.

How should we think about sort of the the difference there, and what's really important to get right in chief staff? Is there is a role that everyone, in addition to EA, wishes they they had Mhmm. 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 chief of staff is more offensive. Yeah. It'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 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 kinda 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.

What have you looked for in chief stat or what what's sort of the right know, there's sort of this tension between, you know, getting someone younger who's, you know, definitely initially gonna do Mhmm. Do it for for a couple years and is more ambitious versus someone who's been more seasoned, but maybe not as high slope or something? What what what how do you think about?

The way I break it down is assistant, you find someone you wanna go a decade with. The intimacy and the compounding of that relationship is super important. Yeah. And so you go deep, and that means you probably don't find a founder because they're not gonna 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 gonna move on in a couple

Yeah.

Years, but they have yeah. They could start a business, but instead, you get them by your side to help solve And

there there are people, you know, like Lonsdale, maybe like Allot or something, who have, you know, chief of staff for, 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, you know, alumni, almost a chief chief staff, just kind of, you know, Peter Thiel's are just kind of further

Yeah. Bezos has this. Someone follows him around. Yeah. It goes to every meeting.

Yeah. And, yeah, it's cool.

Yeah. Let let's talk about some 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 who 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 I'll just say one for for someone like Lonsdale.

Thiel has done this really well. They sort of compound these certain talent networks. So, 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 sort of, you know, created you know, they're deep in the hackathon scene.

Yeah. But they just kind of build this proprietary compounding sort of talent base that they're constantly, you know, sort of

I mean, the the talent access is part of it. I think the other thing is there are some people who have just limitless ambition. And you're very much this way of like, well, what if I could do 10 times more things? Yeah. And I think lots of people just think that's impossible.

Yeah. 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.

Yeah. 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, you know, then you go from assistant to a chief of staff, and you just keep leveling up to, you know, until you're Monsdale or Yeah. The president.

I I think another thing I've admired about some of these people is they, hold remarkably few grudges. Apparently, Peter Thiel kicked Elon out of PayPal or something. A lot of these people have had beefs 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, mean, look what President Vance said about President Trump before they were partners. Think there's a

Trump's actually quite forgiving. 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 at all costs, and, yeah, grudges are not helpful. Yeah.

Even Trump and Elon. Right? Yeah. Getting into it and, you know, reconciling. Yeah.

It's, know, TBD where it stands by by the time this comes out. And then and then there are some people who seem to have pretty like, you know, Bill Gates has, like, you know, pretty big team, pretty big operation. But then it seemed like Bezos and Elon maybe have like pretty lean Mhmm. Teamed into it. Yeah.

I'm curious how you think about sort of

I mean, Elon's the one that makes no sense. It's 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 am my assistant. It's I I hardly believe it, but Elon's just insane. So maybe he is that that way. I think most normal humans, if you wanna get leverage, you have to Yeah. Delegate.

I mean, the 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. Also, in terms of prioritization, like, 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 Mhmm.

I was like, well, if they're in meetings with me, then they're not working.

Like, I

I want them to be, like Yeah. You know, finding ways to give me leverage and take things off my plate.

I mean, 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 gonna do anything. But if the digital, the machine assistants are surveying and pulling things out, that's a pretty cool combination.

Yeah. Yeah. I think it's interesting to look at how people build out their like, for example, you know, Mark and Ben funnel everything through acing a z and are all in on acing a z and, of course, have, you know, other intellectual or philanthropic interests, but mostly it's, like, consolidate. Whereas someone like Peter Thiel has this he sort of fragments it a bit more, you know, like, you know, Founders Fund, but then other several other, you know, Mithril several other funds, other company, all sorts of, like, initiatives that are, you know, somewhat collaborative but independent. Yeah.

And he sits on top, but also it seems like he lets them you know, he's not like CEO of of of them. And he's got this sort of talent, you know, network that he's worked with for a long time Mhmm. That kind of, like, you know, goes in almost boomerangs across the Yeah. The universe. Lonsdale feels like he's more hands he's got the ABC universe, but then his his other initiative, he's, like, quick to institutionalize something, whether it's like a think tank or, like Yeah.

You know, it it's no coincidence that, you 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 to some degree.

And then, yeah, Elon, you know, it's been described also has this like SWAT team Mhmm. You know, of 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. Yeah. And, you know, Marc Andreessen and Ben Horowitz are company builders, and so they're building their leverage like a company.

The a sixteen z is a company. Not that Peter Thiel is not an entrepreneur, but he's more of a philosopher today. And so his system is more like a philosopher. It's all these kind of wild and crazy ideas. And so I think, you know, Jensen Huang has, like, 46 direct reports or something Yeah.

Which is absolutely insane.

Yeah.

But it works for him. And so I think you just have to know what your style is Yeah. And then you build it for you. Totally.

And someone like, you know, Sam Allman is like a deal maker and a fundraiser Mhmm. And a talent identifier, you know. And so he's able to like, I remember he was at YC, he and 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. And he's like, he he has a knack for for good ideas. He has a knack for and this person was, 22. He has a knack for, you know, 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, forget about my weaknesses. I'm just not even gonna try.

Yeah. I'm just gonna be really good at my strengths, and I'm gonna hire other people to do all the things I'm not good at, and that is way more effective.

Yeah. Totally. The there used to be this sort of skepticism of like, hey, you can't really and this still is actually. You can't really incubate company. Like, the the CEO has to be the co founder, they have to drive it to where 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 fifty years. Yeah. Totally. And that's not incubation. Incubation is kind of let me Yeah.

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, $100,000,000 businesses, which is still incredible.

Right. Yeah. I think one bull case is more of it's like a breeding like, you know, Sam Altman in some sense incubated OpenAI 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 then went all in 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 because like, sea studying and things like that because they just disappear into the ether and then things that work compound. And so, yeah, 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 Yeah.

That's a cool cool approach.

Right. A decade ago, Marc Andreessen wrote this blog post on productivity. Yeah. And they were asking him, how do 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 wanna kinda wanna 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 Mhmm. Next week and we'll see how I feel. Yeah.

And it kind of is like better aligned with sort of the flow state.

I mean, that's the ultimate flex. Yeah. It's like, if if you can pull that off, that is definitely the ultimate way to Yeah. Because you just work on whatever you want, world opens up to you, you call.

Right.

Obviously, it's hard for most new mortals to pull off, but, if you can get to that level, that is the dream.

Right. So, I was, for certain meetings that people are cold reaching out or whatever, was kind of try It's like I always anticipate that in a few more days, I'll be busier than I am or something, I'll have Whereas, right now, yeah, got time. Give me a call. But, so, I I tried that a little bit. And then, Mark did a follow-up interview where someone asked him about that, Shuram.

And, he's like, oh, you know, that didn't work. Like, I I I tried, but it didn't work. Now, I'm just scheduled and everything.

Just back to back

all day long. Was like, goddamn it. He was doing that. And it's but he's yeah. 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 see if it works. I think most people just go with the flow. I think 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. You know, I've, back in the Uber versus Lyft, 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, hardcoreness 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. What what advice might you have for others in terms of cultivating this

Yeah, I think it's like a cold plunge or something. It's just you 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. Bring it on. Totally. I don't think there's there's much other than knowing that it's gonna happen.

There's gonna 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 gonna work, and it's like, you just gotta 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 in the game so that we can eventually eventually win. 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, my god. Someone said something mean about me on the Internet.

Mhmm. And then it's like, oh my god. Someone wants to, like, leave my company. Mhmm. And then it's like, oh my god.

We're gonna we're you know, we might die. Like, we only have six months of payroll. Then it's like, my shit. We're gonna 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. Yeah. It's like, you're gonna have that stuff constantly. Yeah. And it becomes, yeah, just part of business.

Yeah. Yeah. And you just keep building up more capacity to handle these things, and they, you know, just Yeah.

And it's where, like, I think co founders are the best. It's just like, it's the people you can be totally open with, and be like, well, our situation's f tough. Yeah. Someone you can trust and Totally. 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 for you?

Yeah. So Athena started fully bootstrapped, human only, scaled to a thousand 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 is you take the best of a human, the best of a 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 human's 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, like, caretaker, the empathy, that partner, and then the machine will increasingly do the more rote, mechanical, administrative stuff. And, you know, just as when you get into a you know, Elon made them with wheels so that or with steering wheels so that you could drive them because they don't drive themselves when he started. But every time you get in the car, you're actually teaching the machine how to drive. Yeah.

And these models don't generalize well. You have to bring edge cases under distribution. 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. So the more your assistant does tasks for you, the more our models will improve, and that'll allow the human to upgrade what they they work on to more Yeah. High leverage stuff.

Yeah. That's exciting. So what what else can you share about plugs for the company or things to watch out for or for people who, you know, wanna get assistance with, you know?

Yeah. Look. I just say, if you don't have an assistant, you are the assistant. Step one, if you're starting a business, you should hire assistant. And if you've got $20 a month, use ChatGPT.

Yeah. If you've got, you know, $10 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. Yeah. You know, Athena, we have 50,000 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 gonna hire on yourself, make sure you interview not 10, but probably, like, 50 people. Yep. If you have the resources for $3,000 a month, then you should work with a company like Athena, who can recruit, train, manage, and teach you how to delegate. And then when you have the resources for an in person assistant Yeah. $100,150 k a year, you should do that as well.

And then ultimately, you know, when you get later stage, you have Achieve a Staff, in person assistant, and, you know, a fleet of Athena assistants in the cloud. Yeah.

That's a great a great overview. Well, let's wrap on that. Awesome. Podcast.

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