How the Best CEOs Delegate

0:00:03 Brian Johnson wants to break the chains of biology.
0:00:04 I want to break the chains of time.
0:00:07 We can always raise another round or do another trade,
0:00:09 but you can’t raise another decade.
0:00:10 You’re running a massive company.
0:00:11 You also do investing.
0:00:14 You’re also happy marriage with four kids.
0:00:16 I know the way that you do it all is delegation.
0:00:18 What is the secret that you’ve figured out?
0:00:23 Cardinal sin of delegation is that it will be faster or better to do it myself.
0:00:25 And the reason it’s a blocker is because it’s true.
0:00:28 But the only way you get leverage is by going through that work.
0:00:31 A couple of decades ago, you had to be Mark Andreessen or Vernot of Kosovo
0:00:33 to have a half dozen assistants.
0:00:35 And that costs you half a million dollars.
0:00:39 Now with a company like Athena for $3,000 a month, you can have your own assistant.
0:00:42 What have you learned in your extensive founder career?
0:00:46 Most people think about delegation as a convenience.
0:00:49 Jonathan Swanson thinks about it as a system for living
0:00:52 and has built his career around a simple idea.
0:00:54 If you don’t have an assistant, you are the assistant.
0:00:59 He scaled Bumtack into one of the major home services marketplaces for the last decade.
0:01:03 Now he’s doing it again with Athena, the number one place to hire a personal assistant
0:01:08 who can run your calendar, your operations, your home, and increasingly, your AI workflows.
0:01:13 Jonathan is running a 4,000-person company while investing on the side and raising four kids.
0:01:17 The through line is a very intentional philosophy of time.
0:01:21 He believes most people underestimate how much ambition they unlock when they learn to delegate well.
0:01:25 In this conversation, we talk about how elite assistant culture shapes him,
0:01:28 what founders consistently get wrong about leverage,
0:01:33 and why he thinks billions of people will soon be delegating to a mix of human and AI partners.
0:01:37 We get into delegation frameworks, splitting work across multiple assistants,
0:01:39 how chief of staffs fit in,
0:01:42 and the mindset shift required to stop optimizing for speed today
0:01:45 and start optimizing for compounding tomorrow.
0:01:46 We hope you enjoy.
0:01:50 Jonathan, welcome to the podcast.
0:01:51 Thanks for having me.
0:01:55 So, Jonathan, you’re running a massive company, what, 4,000 employees?
0:01:56 4,000.
0:01:56 4,000 employees.
0:01:58 You also do investing.
0:02:00 You’re also happy marriage with four kids.
0:02:02 How do you do it all?
0:02:04 I know the way that you do it all is delegation.
0:02:07 You have a chief of staff, a bunch of EAs.
0:02:11 Why don’t you talk about what is the secret that you’ve figured out that other people can learn from?
0:02:17 Yeah, so my origin story here is, out of school, I worked at the White House,
0:02:22 and I sat in the West Wing next to the president’s executive assistants.
0:02:26 And as you might imagine, the EAs in the West Wing were really freaking good.
0:02:31 And it set my bar super high for what this EA client partnership could look like.
0:02:36 And when I moved to San Francisco to start Thumbtack, I said, okay, I’m not president,
0:02:41 but what if I had an EA and support team that was as good as the president’s?
0:02:43 What could I accomplish?
0:02:47 And so at Thumbtack, as we were scaling the business, I hired my first assistant in the Philippines,
0:02:52 started helping me with basic stuff, inbox, calendar, and then we just got creative.
0:02:55 And we did more and more complex, interesting things, which we can talk about.
0:03:02 And what I found was the more leverage I got, the more ambition I got, and it just compounded.
0:03:05 And it started with one assistant, now I’ve got a half dozen,
0:03:09 and every assistant gives me more leverage to take on more things.
0:03:13 It’s fascinating, because some people say, hey, Bill Gates is so much richer than me,
0:03:15 but he has the same phone that I have.
0:03:17 Or I remember, maybe it was you, maybe it was someone else who was like,
0:03:19 the president should have way better information than me,
0:03:21 and yet they’re like reading Politico, too.
0:03:24 Like, they’re reading the same, and this is like another example of it,
0:03:27 which is, you know, the democratization, where the White House have amazing assistants,
0:03:32 but thanks to Athena and technology, at some point, everyone will have a certain block.
0:03:36 Exactly. A couple decades ago, you had to be Marc Andreessen or Vinod Khosla
0:03:40 to have a half dozen assistants, and that cost you half a million dollars.
0:03:44 Now, with a company like Athena, for $3,000 a month, you can have your own assistant,
0:03:46 and then with AI, yeah, it’s going to become ubiquitous.
0:03:51 There’s going to be billions of people learning to delegate to a machine assistant,
0:03:55 and as your budget increases, you might add a human or a chief of staff on top,
0:03:57 but it’s just kind of a ladder of leverage.
0:04:02 How should we think about what are the things that humans can do versus what are the things that AI can do?
0:04:07 I remember my friend started Clara, you know, a decade ago, which is trying to be AI assistants,
0:04:10 effectively, obviously, this is well before a lot of the innovation,
0:04:14 but what is the right way of thinking about sort of the human-AI relationship?
0:04:15 Yeah, I mean, it’s a moving target, obviously.
0:04:20 AI is going to get increasingly more capable, and our view is it’s like self-driving cars,
0:04:21 where it’s not self-driving overnight.
0:04:26 It’s you drive the Tesla at first, and then there’s assisted steering and braking,
0:04:31 and then over time, it becomes more autonomous, and the same thing is going to happen with assistants.
0:04:35 My view here for founders is if you don’t have an assistant, you are the assistant,
0:04:36 and you don’t want to be the assistant.
0:04:40 And so no matter your budget, you should first start by learning to delegate.
0:04:45 And if you only got $20 a month, you start by delegating to ChatGPT.
0:04:48 And prompt engineering is really just delegating.
0:04:53 And if you become world-class at leveraging ChatGPT to brainstorm your goals,
0:04:56 figure out how you can take the next step in the business,
0:05:00 once you have the budget for a human assistant or a chief of staff,
0:05:02 then you’re prepared to go that next level.
0:05:04 So you start $20 a month.
0:05:08 If you have budget, then you hire someone direct with a service like Athena.
0:05:09 If you have enough money, you hire someone in person.
0:05:10 That’s six figures.
0:05:15 And if you’re a legendary budget, then you’ve got a suite of assistants
0:05:16 and chief of staffs following you around.
0:05:17 Yeah.
0:05:22 So I’ve had Anithia Yeh for many years now, and she’s absolutely amazing.
0:05:26 And I use her for scheduling and typical assistant activities.
0:05:29 But you have many assistants.
0:05:31 Our friend Sam Korkos has a bunch of assistants as well.
0:05:35 What else do people get leverage on or delegate that maybe is not obvious?
0:05:39 So first, you start by taking the pain off of your life.
0:05:40 So I never wait on hold.
0:05:42 I never put my credit card in the internet.
0:05:46 I would never fill out DMV forms, never do passport renewal.
0:05:49 The world is full of all these annoyances.
0:05:52 And so first, you take off these things that drain you,
0:05:53 that don’t give you leverage.
0:05:55 Then once you’ve done that,
0:05:57 then the next thing is you raise your sights.
0:05:59 And you’re like, what’s a new business I could start?
0:06:00 How can I scale my business faster?
0:06:02 How can I spend more time with my family?
0:06:05 What are the things I actually care to do a lot more of?
0:06:06 Yeah.
0:06:10 And so I start with basic stuff, inbox, calendar, stuff that everyone does.
0:06:12 But then I just start experimenting.
0:06:17 And so during the scale-up days of Thumbtack, when we’re in a house working all the time,
0:06:22 I told Marnie, my assistant, I don’t really have any friends outside of work.
0:06:24 I was like, the only people I know are in this building.
0:06:25 I need to make some friends.
0:06:29 And so I told her, let’s plan a founder dinner at my house every other week.
0:06:31 And we did lots of this together back in the day.
0:06:33 And that’s how I made all my best friends.
0:06:37 And I just walked home from work and Marnie had invited people,
0:06:39 set up the chef and the bartender.
0:06:40 And we walk in and we make new friends.
0:06:42 And I met Catherine, my wife, through that.
0:06:44 And then Marnie’s helping plan our wedding.
0:06:45 And now Marnie helps us with our kids.
0:06:49 And so it starts small and then you just kind of compound these things.
0:06:54 Yeah, but even in that example, say more about how did she know who to reach out to?
0:07:00 Yeah, so the kind of entry-level delegation is you delegate by task.
0:07:02 You say, help me plan this dinner party.
0:07:04 If you just say that, you’re not going to get what you want.
0:07:08 The more advanced way to delegate is called delegate by algorithm,
0:07:12 where you actually export your own internal preferences as you delegate.
0:07:17 So I would say, hey, when I plan dinner parties, I like to have six to eight people.
0:07:22 I like people to have raised similar amounts of capital or be at similar stages or similar number
0:07:26 of employees and literally write an algorithm for how you find the right people.
0:07:29 And then you give feedback on whether it worked or not.
0:07:33 And once the algorithm is fully exported from your head, then it’s just rinse and repeat.
0:07:38 And so engineers tend to be better at creating these kind of like SOPs or standard practices,
0:07:40 but it’s something that you can learn to do.
0:07:45 Yeah. And so share more about, for people with multiple systems, how do you differentiate?
0:07:48 Like, how do you sort of delegate across the team?
0:07:49 Yeah, I mean, start with one.
0:07:50 Yeah.
0:07:52 And then like any team, you specialize.
0:07:55 And so I just had one that did everything as a generalist.
0:08:00 And now half a dozen, which I know sounds crazy, but each one specializes in different things.
0:08:01 One is on work.
0:08:02 One is on home.
0:08:05 One is on kids, family, travel, finances.
0:08:06 Yeah.
0:08:11 And that specialization is helpful because the finance person is just thinking about balance sheet,
0:08:13 you know, sending wires, all that sort of stuff.
0:08:18 And then I have a chief of staff who sits on top, who distributes work across all of them.
0:08:22 What are other principles, like I love this, delegate by algorithm, not by task.
0:08:28 What are other principles or frameworks that are really important or non-obvious to get the most out of an assistant?
0:08:33 Yeah, the cardinal sin of delegation is that it will be faster or better to do it myself.
0:08:34 Yeah.
0:08:35 That’s the number one blocker for most people.
0:08:37 And the reason it’s a blocker is because it’s true.
0:08:38 Yeah.
0:08:41 It will actually be faster or better if you do it yourself that first time.
0:08:42 Yeah.
0:08:45 And it takes more effort to delegate, to teach someone how to do it.
0:08:50 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.
0:08:53 So you have to overcome that activation energy.
0:09:01 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.
0:09:03 But it’s the compounding that creates incredible leverage.
0:09:07 I’ve been working with Marnie for a decade, like a little sister now, and she knows everything about me.
0:09:10 So that’s just kind of like common principles.
0:09:15 In terms of the way to delegate, I think this is just tactical, the methods.
0:09:18 The most common way people delegate is with your thumbs on your phone.
0:09:19 That’s the worst way.
0:09:20 Very slow.
0:09:24 Better use all 10 fingers at a computer, but that’s actually pretty slow as well.
0:09:26 The best way to really delegate is using your voice.
0:09:30 And so voice, you can talk two to three times faster.
0:09:31 You can do it on the go.
0:09:35 You can do it on a date and between lunch and the Uber.
0:09:38 A thumbtack during hyperscale times, I would walk between meetings.
0:09:41 And between a meeting, I would be voice noting to an assistant.
0:09:43 Here’s the takeaways.
0:09:44 Pre-draft these five emails.
0:09:46 Follow up with this person.
0:09:53 And all my work from that meeting was actually delegated by the time I started the next meeting versus everything kind of accumulating.
0:09:56 And then you get to the end of the day and you’re like, I have a hundred things to do.
0:10:05 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.
0:10:05 Right.
0:10:06 Yeah, it’s fascinating.
0:10:09 At some point, it’s going to be, I don’t even have to say it, I just think it.
0:10:17 This is part of our vision, Athena longer term, is you shouldn’t have to actually vocalize it.
0:10:20 And we’ve built an internal demo of this.
0:10:26 It’s not live for customers, but the way it works is we build something that watches your screen as you work.
0:10:29 And it screenshots the screen.
0:10:36 And when it identifies things that you should be delegating to your assistant, it automatically adds it to your assistant’s task list.
0:10:40 Your assistant then says, oh, Eric would want my help with this, or maybe he’ll do this one his own.
0:10:44 And that creates the reinforcement learning effectively to tune the model.
0:10:47 To pull things off of your screen, you don’t have to vocalize.
0:10:50 And so the person who built this internally has been using it.
0:10:53 The majority of his delegations are now machine generated.
0:10:54 He’s not talking.
0:10:59 He’s just working and the machine is magically pulling tasks and putting on his assistant’s plate.
0:11:03 It’ll take a while to bring that to market and fruition, but that’s the future.
0:11:13 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?
0:11:20 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.
0:11:27 And that’s really the vision of Athena, is like the best human assistant, the best AI wrapped into one combined product that’s seamless.
0:11:43 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.
0:11:57 Yeah. One thing you’ve always been fascinated about is sort of international labor, some 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?
0:12:03 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 about it?
0:12:17 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, et cetera.
0:12:29 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.
0:12:41 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? Because are you still interfacing with the accountants? What is the right way of thinking about it?
0:12:47 Yeah. So the first thing I’d recommend if you’re getting an assistant is to have them help you save money.
0:12:47 Yeah.
0:12:58 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.
0:13:03 So that’s just kind of like a cost saving bucket. Then there’s admin paying bills.
0:13:04 Yeah.
0:13:21 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 systems at enough scale and complexity that becomes effectively a full-time job.
0:13:39 And obviously you need someone you truly trust 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.
0:14:01 Yeah. The, um, yeah, it’s really interesting. And in terms of, um, 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, um, yeah, kind of what are the challenges or what’s really important to get right?
0:14:16 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 no American pop culture and sports better than I do.
0:14:31 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
0:14:48 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, uh, barriers for some people to get an assistant is it feels indulgent.
0:15:02 Yeah. 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 and 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.
0:15:11 Yeah. And for the people on our team, like they could have worked with the CEO. They get to see behind this exciting startup that, um, is a totally different life than they live.
0:15:31 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, uh, 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 or something.
0:15:41 Oh, do we have some, uh, 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.
0:15:59 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 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.
0:16:17 You can get that for 20 bucks a month. Um, I’ve done similar versions of this with a human assistant. 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.
0:16:28 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.
0:16:44 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 operational savvy, but also, you know, pretty, you know, uh, intuitive, you know, they go into caring fields.
0:16:56 And so there’s also like opportunities for coaching too, or like 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?
0:17:22 Yeah. Yeah. It was my first observation, uh, 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. Um, 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?
0:17:47 And it was, 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, uh, good AI gets. And it’s something you should lean into.
0:18:03 We have clients who tell us that, yeah, like going through a divorce or a depression and like my assistants 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.
0:18:27 Yeah, totally. Relatedly, one of the things you’ve had really interesting insights on over the years is, uh, is how to spend time to think about time management, not, 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, I’ve learned this from, from you, but you think about goals on a sort of, you know, annual quarterly, you know, like on different increments.
0:18:34 Maybe we could start with LBD and how you think about goal, goal setting in general, and then we can, you know, get a bit deeper.
0:18:58 I mean, my wife, Catherine and I, who, uh, we met as friends, one of, you know, developed this friendship over one of these entrepreneurship dinners. We read this book, um, 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.
0:18:59 Yeah.
0:19:01 They’re divorced, they have all these problems, the kids don’t talk to them, going to jail.
0:19:02 Yeah.
0:19:21 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 and 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 director. Yeah.
0:19:40 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 can we do better? And like anything, if you, the more you invest, the better it gets.
0:20:05 Yeah, totally. And yeah, I think that’s a key point, because some people are turned off by sort of like, uh, quantification, like they want their relationship to be placed to like, you know, relax, to 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 prior, you don’t want to let the lack of quantification mean that you’re not prioritizing it. Um, and so this is just an exercise to make sure that you’re actually just like keeping accountable to how you want to be.
0:20:34 Exactly. It’s, uh, be purposeful, get the thing you want. If you’re a geek like us and you measure it and you track everything. Uh, 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, uh, 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.
0:21:02 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, prioritization. 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? Um, and, uh, 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.
0:21:03 Who sets too many goals?
0:21:07 You know, me a little bit. Uh, but, uh, but yeah.
0:21:30 Yeah. 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 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.
0:21:59 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.
0:22:18 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, what are certain sort of frameworks that are important for you in terms of time, energy?
0:22:46 I mean, high level is a 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 asked myself is like, what’s the most valuable asset in the world? It’s not gold or Bitcoin or Nvidia clusters. It’s time. Uh, 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, uh, and it’s more foundational than everything else, we should focus on owning that and controlling it.
0:23:08 Yeah. 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 14 hours a day where you are just grinding out interviews and doing things that only you can do as a founder. Uh, or it may mean clearing your schedule and having time to dream about the future of the product or big deals.
0:23:08 Yeah.
0:23:25 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.
0:23:35 Yeah. I remember, uh, Keith Reboi 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.
0:23:47 I mean, there’s 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?
0:23:48 Yeah.
0:23:50 If not, then next week we should adjust those things.
0:23:59 Yeah. I’m curious for your interpretation of meetings. Some people are like, uh, you know, I, I want to have as few meetings as possible. It means not the most efficient. I’d rather do everything async.
0:24:00 Yeah.
0:24:03 What is your kind of sort of thinking between async and synchronous?
0:24:31 I mean, Naval has a good line that’s like, uh, a phone call is better than a meeting. A voice note is better than a call. A text is better than a voice note. Uh, I think in general, that’s true. And, uh, 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.
0:24:58 It’s really high bandwidth. You can figure shit out in five minutes. And so, uh, I personally try to minimize meetings and then do more picking up the phone and talking to someone for five minutes. Um, when I’m in more chairman mode, then I prioritize as few meetings as possible and voice notes. And, um, I, uh, I, what I request is voice notes out and text message back because listening to voice notes is slow.
0:25:25 It’s, uh, assault as market trees. Yeah. Um, yeah, it is interesting. You know, uh, uh, one of my favorite self-help books is the seven effective habits, how to fix people. And one of their, you know, principles maxims is this idea of like efficiency with, when it comes to achieving, uh, you know, tasks or accomplishing tasks, but effectiveness when it comes to people. And, and so, um, you know, the efficient path might not be the effective path.
0:25:41 The effective path is you might, you sort of save some time on the front end, but you might, you know, accrue sort of a debt on the, on the back end. Yeah. And, um, yeah, it might be efficient to just send a text or something, but, you know, keeping the dynamic, you know, phone calls are obviously under, underrated.
0:25:53 Yeah. That’s true 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.
0:26:09 Totally. How, 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.
0:26:25 Most important ways to, to get right. Whether it’s your time at thumbtack. Yeah. I mean, it’s like, it’s build your product, it’s customers, raise capital, build your team. And when founders asked me like how to leverage an assistant, what should I be doing? My way I turned around is like, what’s your top two goals for the month?
0:26:49 Yeah. 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. 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, your assistant could help project manage the process of all of that.
0:27:04 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 around 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.
0:27:14 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 like really get the most leverage out of it and watches, you know, your, your, your activity.
0:27:22 I mean, 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.
0:27:29 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?
0:27:49 And so it became clear we need 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.
0:28:04 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.
0:28:17 Yeah. One thing that you’ve been phenomenal at is whether some tech or Athena is, is hiring executives. What do you think that you do differently or what are the principles or frameworks that really guide your sort of exact hiring process?
0:28:41 I mean, one thing that is obvious as you hire execs is the more senior they go, the better they are interviewing and 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.
0:28:48 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.
0:28:58 Like at their last company, 10 people wrote reviews of them that are honest about their strengths and weaknesses. And I just ask to see it and I say, hey, I’ll share mine, you show me yours.
0:29:06 I actually think this would be a cool kind of reference pro startup where you could like ping the LLM about someone versus pinging their references.
0:29:15 So I try to get to more ground truth on the person versus the UX of the interview is just going to be pretty good when you get to the senior level.
0:29:22 That’s interesting. What’s most important when you’re doing reference checks? What’s the way to get the most signal out of them?
0:29:32 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.
0:29:44 Because, you know, 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.
0:29:47 And once they start to sound the same, then you’ve got a signal.
0:29:53 Yeah. Well, one question I like to ask is what skill sets would be really important to compliment this person with?
0:29:56 It was another way of saying what are they bad? Like, you know, what’s really important?
0:30:02 Or one of my questions is if this didn’t work out in six months or a year, you know, why would that be?
0:30:12 Yeah. And I mean, the best way to source talent is hired an executive recently is just ask the people that you respect the most. They have the highest standards. Who’s the best person?
0:30:18 Like, here’s the three people who have the highest standards in this role. I asked them for the two or three best people and I go to try to hire one of them.
0:30:32 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 this cold leads, but going through a network of high bar people is super efficient.
0:30:38 There’s some maxim that almost like half of executives, you know, don’t work out within like, you know, 12 to 24 months.
0:30:41 Checks out. Yeah. Why is that?
0:30:54 I think it’s this, 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 going to do.
0:31:04 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.
0:31:15 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.
0:31:22 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.
0:31:30 And if you know, like you also want to avoid that, you know, I’m not the trap of not taking enough risk or moving too slow.
0:31:36 Yeah. And as long as you cut your losses quickly, it’s okay. If you like don’t cut losses, then you compound a hole.
0:31:43 That’s where it’s painful. The other thing I’d say is more useful for basically all interview process is project based work.
0:31:52 So just like, you know, hiring a C-suite for one part of the team, I just tell them what the pain points in the org are and what I want to fix.
0:31:57 And I’m like, come up with a plan. How would you fix this? Like, if we hire you, you’re then going to do it.
0:32:01 Yeah. And that sort of practical work is more useful.
0:32:10 Yeah. That’s really interesting. What, um, going back to other sort of founder principles, what is your stance on, um, transparency with the company?
0:32:16 Like what’s information that’s helpful? Maybe going back to Thumbtack days, what’s helpful for the company to employees to know?
0:32:20 Or like, what are principles like the guide, you know, how much you share?
0:32:41 Yeah. I mean, default transparency is obviously the best, but there’s obviously some lines. Like there’s, uh, 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.
0:32:48 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.
0:32:53 Uh, there was a misunderstanding. They thought we’d done something wrong, but they like eliminate us from the internet.
0:33:05 And so our traffic went to zero, uh, 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.
0:33:18 And this was 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.
0:33:34 But if I just walked into a new class and say, hey, the business might be dead, uh, it’s not going to work. And so you have to kind of get a handle of 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.
0:34:02 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. Um, I feel like it’s pretty rare when I think about co-founding teams that it feels like the non-CEO, especially if not a CTO, usually doesn’t last, you know, over five years or something. Um, I’m curious what’s really important to get right in, in co-founder relationships or how you think about advising, you know, companies that you invest in.
0:34:31 Yeah. I mean, the, uh, 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,
0:34:48 you know, it’s good to know that going into starting a business, uh, in terms of who to pick the, 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. Uh, you know, no makeup sex, but it’s still like, uh,
0:35:03 yeah, there’s highs, lows, and you want someone that ultimately you, you really deeply trust cause there’s going to be stress and, um, 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,
0:35:24 I don’t know if I called a mistake at thumbtack, uh, 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’re doing. And, uh, you know, it worked out.
0:35:54 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 like clear executive. Yeah. And I think that’s, uh, you know, it’s not recommended cause 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, 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 go to grad school.
0:36:24 But you, 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 pretty good. But how do you, pretty good decision. Um, how did you at the time think about get enough conviction to take the leap and do it?
0:36:38 Yeah, it was scary. I, uh, got into, you know, this good school, seemed like that was a safe bet. I knew I wanted to start a business and, uh, you know, if I went to business school, I knew that I’d have all this debt.
0:36:59 I probably might need to get a nice paying job afterwards. And if I was going to go for it, I should probably just go for it. But yeah, when the dean sent me that email, it’s like, this is biggest mistake of your life. He said something like, uh, you can, startups will come and go, but you can only come to Stanford once or something. This is a once in a lifetime opportunity.
0:37:09 I never responded. And I have it as a email in my, this save that I’m just going to respond to whenever some tech goes public and be like, I made the right decision.
0:37:17 Uh, 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.
0:37:27 Yeah, totally. Okay. So there’s EAs and then they’re 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?
0:37:33 Is there, is a role that everyone in addition to EA wishes they, they had, um, but seems hard to find the right person.
0:37:41 Yeah. There’s no formal definition. I think it’s something that, uh, an EA is typically more administrative and taking things off your plate.
0:37:47 And, uh, chief of staff is more offensive and that’s the type of person who can follow you into meetings.
0:37:54 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.
0:37:59 And so achieve a staff typically has the capabilities to become a founder themselves.
0:38:05 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, uh, to do it.
0:38:14 So you kind of get people who do more tours of duty and you get super high capability, uh, but you don’t get the same longevity as a assistant.
0:38:25 What have you looked for in chief staff or what, what sort of the right, you know, there’s sort of this tension between, you know, getting someone younger, who’s, you know, definitely going to do it for, for a couple of years.
0:38:32 Um, and is more ambitious versus someone who’s been more seasoned, but maybe not as high slope or something.
0:38:36 How do you think about the way I break it down is assistant.
0:38:42 You find someone you want to go a decade with, uh, the intimacy and the compound, you know, that relationship is super important.
0:38:47 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.
0:38:51 It’s someone who’s much more of a caretaker and is excited to be number two.
0:39:02 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.
0:39:13 Totally. And there are people, you know, like Lonsdale, maybe like a lot or something who have, you know, chief of staff for like a year or two, and then they start a company and then they invest in them and they build kind of this reputation for, for doing.
0:39:20 And then they have sort of these like, you know, um, alumni, almost a chief of staff, just kind of, you know, Peter Thiel is just kind of further.
0:39:25 Yeah. Bezos has this, someone follows him around that goes to every meeting and yeah, it’s cool.
0:39:31 Yeah. Let’s talk about some, some people who get an enormous amount done.
0:39:47 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?
0:39:50 I’ll just say one for someone like Lonsdale, Thiel has done this really well.
0:39:56 They sort of compound these certain talent networks. So, you know, there’s like Stanford review or just Stanford in general.
0:40:01 Um, they’re often hiring people from there and then involved in sort of these talent pipelines.
0:40:11 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.
0:40:23 I mean, 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?
0:40:24 Yeah.
0:40:50 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.
0:40:51 Yeah.
0:41:06 And then that, uh, 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 and it’s difficult to have big ambition if you’re just weighed down by DMV forms and passports.
0:41:07 Yeah.
0:41:19 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 Lonsdale or the president.
0:41:36 I think another thing I’ve admired about some of these people is they, um, you know, they remark hold remarkably few grudges like, um, 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.
0:41:37 Mm-hmm.
0:41:47 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.
0:41:52 Yeah, I mean, look what, uh, President Vance said about President Trump before they were partners.
0:41:53 Yeah, yeah, yeah.
0:41:54 I think there’s–
0:41:59 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 your mind.
0:42:05 Yeah, I think there’s just a desire to win, uh, at all costs and, uh, yeah, grudges are not helpful.
0:42:07 Yeah. Even Trump and Elon, right?
0:42:08 Yeah.
0:42:10 Getting into it and, you know, reconciling.
0:42:11 Yeah.
0:42:14 It’s, uh, you know, TBD where it stands by the time this comes out.
0:42:21 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.
0:42:22 Yeah.
0:42:26 Um, but then it seemed like Bezos and Elon maybe have, like, pretty lean.
0:42:27 Mm-hmm.
0:42:29 And so, yeah, I’m curious how you think about, sort of–
0:42:31 I mean, Elon’s the one that makes no sense.
0:42:32 Yeah.
0:42:36 It’s, he claims to not have an assistant and to be, like, scheduling stuff.
0:42:41 There’s a story of Bill Gates being, like, trying to schedule a meeting with Elon.
0:42:43 He’s like, connect me with your assistant.
0:42:45 And Elon’s like, no, I am my assistant.
0:42:48 Uh, it’s, I, I hardly believe it, but Elon’s just insane.
0:42:49 Yeah.
0:42:50 So maybe he is that, that way.
0:42:51 Yeah.
0:42:55 I think most normal humans, if you want to get leverage, you have to delegate.
0:42:56 Yeah.
0:43:00 I mean, the, one of the cool personal teams I saw is this guy who’s a billionaire.
0:43:04 He runs this hedge fund, and he has a team of 40.
0:43:07 Uh, he has eight personal, uh, executive assistants.
0:43:10 The, all of the executive assistants graduate from Princeton.
0:43:12 Insanely high bar.
0:43:17 And I was asking this woman who managed the EA team, like, how do you decide what to prioritize
0:43:18 your team on?
0:43:25 And she’s like, if my team can spend one day saving my, uh, principal one minute, it’s
0:43:27 well worth our time.
0:43:29 And I’m like, that is so next level.
0:43:33 And definitely like, that’s something I would love to aspire to, but it’s just, you know,
0:43:36 the, the, the billionaire budget.
0:43:37 Yeah.
0:43:38 It’s pretty funny.
0:43:41 Um, also just in terms of prioritization, like, um, you know, we’re hiring, you know,
0:43:45 assistants here and someone saying, oh, you know, do you want them to be in all meetings
0:43:46 with you?
0:43:48 And I was like, well, if they’re in meetings with me, then they’re not working.
0:43:52 Like I want them to be like, you know, finding ways to give me leverage and take things off
0:43:53 my plate.
0:43:57 I mean, this is one of our visions, uh, uh, Athena is that you can have digital assistants
0:44:00 that listen to you and work with you and are connected to your zoom and your inbox
0:44:05 and your calendar and can be mining all of that digital exhaust for things your assistant
0:44:06 should work on.
0:44:09 And so, I mean, your assistant can’t possibly sit in every meeting if they’re going to do
0:44:14 anything, but if the digital, uh, the machine assistants are surveying it and pulling things
0:44:16 out, that’s a pretty cool combination.
0:44:17 Yeah.
0:44:18 Yeah.
0:44:20 I think it’s interesting to look at how people build out their universe.
0:44:25 Like for example, you know, Mark and Ben funnel everything through A, C and Z and are
0:44:26 all in on A, C and Z.
0:44:32 And of course have, you know, other intellectual or philanthropic interests, but mostly it’s like
0:44:33 it can sell it.
0:44:38 Whereas someone like Peter Thiel has this, um, he sort of fragments it a bit more, you know,
0:44:43 like, um, you know, founders fund, but then other, several other, you know, Mithril, several other
0:44:50 funds, other company, all sorts of like, um, initiatives that are, you know, somewhat collaborative,
0:44:51 but independent.
0:44:52 Yeah.
0:44:57 Um, and he, he sits on top, but also it seems like he lets them, you know, he’s not like
0:44:59 CEO of, of, of, of them.
0:45:05 Um, and he’s got this sort of talent, you know, network that he’s worked with for a long time.
0:45:12 That kind of like, uh, you know, goes in almost boomerangs across the, the universe.
0:45:16 Um, Lonsdale feels like he’s more hands.
0:45:22 He’s got the ABC universe, but then his, his, um, other initiative, he’s like quick to institutionalize
0:45:26 something, whether it’s like a think tank or like, you know, it’s no coincidence that, you
0:45:29 know, Peter Thiel would do the sort of Thiel fellowship and Lonsdale will create a university
0:45:30 or something too.
0:45:32 It was almost like early to stuff.
0:45:37 He creates a format for something, um, a template, uh, you know, he does the hard work of sort
0:45:42 of, um, you know, field building into like, or like, you know, uh, doing something that’s
0:45:47 in a controversial space where it’s longevity or charter cities or, um, you know, higher education.
0:45:52 And then, um, you know, people like Lonsdale institutionalize it to some degree.
0:45:57 Um, and then yeah, Elon, you know, it’s been described also has this like SWAT team, um, you
0:46:00 know, of, of people that help him from, from company to company.
0:46:01 Yeah.
0:46:05 And he’s just able to recruit, you know, world-class people to, to lead these efforts.
0:46:06 Yeah.
0:46:09 I think it comes, it’s like, what’s the right org structure?
0:46:10 Yeah.
0:46:11 There’s actually no right org structure.
0:46:14 It’s what’s the right org structure for you as a founder.
0:46:15 Yeah.
0:46:18 And, you know, Marc Andreessen and Ben Horowitz are company builders.
0:46:23 And so they’re building their leverage like a company, the A16Z is a company.
0:46:28 Uh, not that Peter Thiel is not an entrepreneur, but he’s more of a philosopher today.
0:46:32 And so his, uh, system is more like a philosopher.
0:46:34 It’s all these kind of wild and crazy ideas.
0:46:39 Uh, and so I think, you know, Jensen Huang has like 46 direct reports or something,
0:46:42 which is absolutely insane, but it works for him.
0:46:46 And so I think you just have to know what your style is and then you build it for you.
0:46:47 Totally.
0:46:51 And someone like, you know, Sam Allman is like a deal maker and a fundraiser and a talent
0:46:52 identifier, you know?
0:46:57 And so he’s able to, like, I remember he was at YC and he was talking to my, one of my friends
0:46:59 about sort of this universal basic income company.
0:47:02 My friend didn’t end up doing it, but I was like, huh, that’s interesting.
0:47:03 Why is, why is he even doing that?
0:47:04 He’s like focused on YC.
0:47:06 He’s like, he has a knack for, for good ideas.
0:47:07 He’s a knack.
0:47:08 And this person was like 22.
0:47:13 He has a knack for, you know, uh, high slope talent and he has a superpower around raising money.
0:47:14 Yeah.
0:47:19 I mean, one of the things that I think new founders, or at least me as a new founder was
0:47:22 like, okay, what are my weaknesses and how do I get better at them?
0:47:26 But then a second time founder is like, forgive all of my weaknesses.
0:47:27 I’m just not going to try.
0:47:31 I’m just going to be really good at my strengths and I’m going to hire other people to do all
0:47:32 the things I’m not good at.
0:47:34 And that is way more effective.
0:47:35 Yeah, totally.
0:47:40 The, um, there used to be this sort of skepticism of like, Hey, you can’t really, and this still
0:47:42 is actually, you can’t really incubate company.
0:47:47 Like the CEO has to be the co-founder and they have to drive it to where do you stand
0:47:49 on, on kind of that, that debate?
0:47:53 I think the biggest companies aren’t incubated because the biggest companies have a founder
0:47:57 who is monomaniacal from the beginning and compounds it for 50 years.
0:47:58 Yeah, totally.
0:47:59 And that’s not incubation.
0:48:02 Incubation is kind of, let me try a bunch of thing.
0:48:05 It’s not this monomaniacal power law commitment.
0:48:10 So if you’re just trying to build a trillion dollar business, I think that’s not the way to
0:48:11 do it.
0:48:15 But look, if you like, you know, we have a mutual friend who likes to remain anonymous,
0:48:20 who incubates lots of companies and he launches four companies a year and he loves doing it.
0:48:22 And he’s going to make a ton of money doing it.
0:48:23 And that’s just his style.
0:48:28 He’s not going to probably have trillion dollar businesses, but he’s going to have 50,
0:48:30 a hundred million dollar businesses, which is still incredible.
0:48:31 Right.
0:48:31 Yeah.
0:48:36 I think one bull case is more of it’s like a breeding, like, you know, Sam Altman in some
0:48:39 sense, incubated open AI and that it wasn’t the main thing he was working on.
0:48:43 But then once he identified that it could be, you know, this massive opportunity, then then
0:48:44 went all in with it.
0:48:45 Yeah.
0:48:46 I mean, it’s more like a venture portfolio.
0:48:50 And, you know, there’s probably a bunch of stuff Peter Thiel has done that we don’t even
0:48:55 remember because like seasteading and things like that because they just disappear into
0:48:57 the ether and then things that work compound.
0:49:02 And so, I mean, if you have the resources to launch 10 new things and then just double down
0:49:04 on the one thing that’s big every year.
0:49:05 Yeah.
0:49:06 That’s a cool, cool approach.
0:49:07 Right.
0:49:10 A decade ago, Marc Andreessen wrote this blog post on productivity.
0:49:11 Yeah.
0:49:15 And they were asking him how you think about, you know, meetings, scheduling, whatever.
0:49:20 And he said, you know what, I try not to schedule things in advance because I don’t
0:49:22 know how I’ll feel, you know, next week.
0:49:24 And I kind of want to do things like in flow.
0:49:29 And so when, you know, people are trying to get my time, what I typically say is like, call
0:49:34 me right now or feel free to check in next week and we’ll see how I feel.
0:49:35 Yeah.
0:49:39 And it kind of is like better aligned with sort of the flow state.
0:49:41 I mean, that’s the ultimate flex.
0:49:42 Yeah.
0:49:46 It’s like, if you can pull that off, that is definitely the ultimate way to live.
0:49:47 Yeah.
0:49:48 Because you just work on whatever you want.
0:49:49 Yeah.
0:49:50 The world opens up to you.
0:49:51 You call.
0:49:52 Right.
0:49:55 Obviously, it’s hard for most new mortals to pull off.
0:49:56 Yeah.
0:49:58 But yeah, if you can get to that level, that is the dream.
0:49:59 Right.
0:50:02 So then I was, for certain meetings where people are cold reaching out or whatever, I was
0:50:08 kind of trying, it’s like, I always anticipate that in a few more days I’ll be like busier
0:50:12 than I am or something or I’ll have, whereas like right now, yeah, I got time.
0:50:13 Give me a call.
0:50:14 Mm-hmm.
0:50:15 But so I tried that a little bit.
0:50:20 And then Mark did a follow-up interview where someone asked him about that, Shuram, and he’s
0:50:22 like, oh, you know, that didn’t work.
0:50:24 Like I tried, but that didn’t work.
0:50:26 Now I’m just scheduled everything.
0:50:27 Just back to back all day long.
0:50:28 Yeah.
0:50:29 And I was like, oh, God damn it.
0:50:34 And it’s, but he’s, you know, he’s also mastered multitasking.
0:50:40 I mean, I think people just, the thing I think you can learn from Mark and other people is
0:50:42 just challenge the defaults occasionally.
0:50:47 And if you’re in back to back meetings all the time, try this other system and see if it
0:50:48 works.
0:50:50 I think most people just go with the flow.
0:50:54 The other thing is most people aren’t vicious enough at saying no.
0:50:55 Yeah.
0:50:58 And just being super hardcore is like, is that conference you’re going to matter?
0:50:59 Yeah.
0:51:02 Is that random, get to know you, chat, mean anything?
0:51:03 Yeah.
0:51:05 I think you just say no to most things.
0:51:13 You know, I’ve, back in the Uber versus Lyft, really scaling war days, I remember emailing
0:51:19 Logan a question, probably to come to one of our dinners and he just responded war mode.
0:51:20 Yeah.
0:51:21 And I love that.
0:51:25 And I’m like, well, most people should actually be in war mode like 90% of the time.
0:51:30 And that same, yeah, hardcore-ness is just like the right way to operate.
0:51:31 Yeah.
0:51:37 What have you learned in your extensive founder career about managing your own psychology, dealing
0:51:43 with stress, dealing with the cognitive dissonance of, you know, having to present externally
0:51:48 like things are amazing even when, you know, you’re concerned about Google, you know, taking
0:51:49 out your business.
0:51:54 Um, what, um, what advice might you have for others in terms of cultivating this?
0:51:55 Yeah, man.
0:51:58 I think it’s like a cold plunge or something.
0:52:00 It’s just, you just shock therapy.
0:52:05 And eventually you, it’s just like you’re bathing in existential fear all the time.
0:52:07 And you’re like, whatever, let’s bring it on.
0:52:08 Totally.
0:52:12 Uh, I don’t think there’s, there’s much other than knowing that it’s going to happen.
0:52:14 There’s going to be tons of ups and downs.
0:52:19 I think one of the clear lessons from Thumbtack, which is now scaled and, uh, and done so well
0:52:24 was that like, there was lots of near misses where we almost died times where we thought
0:52:25 it wasn’t going to work.
0:52:27 And it was like, you just got to stay in the game.
0:52:28 Yeah.
0:52:30 And if you can stay in the game, you can eventually win.
0:52:31 Yeah.
0:52:35 And I think Thumbtack was very good at staying in the game so that we can eventually win.
0:52:37 Um, yeah.
0:52:38 It’s funny.
0:52:40 There’s like degrees of panic in the beginning, you know, you’re getting your feet wet.
0:52:43 It’s like, oh my God, someone said something mean about me on the internet.
0:52:44 Mm-hmm.
0:52:47 And then it’s like, oh my God, someone wants to like, leave my company.
0:52:48 Mm-hmm.
0:52:53 And then it’s like, oh my God, um, we’re going, we’re, you know, we might die.
0:52:54 Yeah.
0:52:55 We only have six months of payroll.
0:52:56 Then it’s like, oh my shit, we’re going to get sued.
0:52:57 Yeah.
0:52:58 It’s like, you know.
0:53:01 Well, it’s like the first time you get sued or you’re worried about getting sued.
0:53:02 Yeah.
0:53:05 And then eventually you have a board meeting and there’s just a list of lawsuits and it’s just,
0:53:06 you review them quarterly.
0:53:08 It’s just like, that’s actually what success is.
0:53:09 Yeah.
0:53:10 Yeah.
0:53:11 It’s like, you’re going to have that stuff constantly.
0:53:12 Yeah.
0:53:14 And it becomes, yeah, just part of business.
0:53:15 Yeah.
0:53:16 Yeah.
0:53:20 And you just keep building up more capacity to handle these things.
0:53:21 And they, you know, just.
0:53:22 Yeah.
0:53:24 And it’s where like, I think co-founders are the best.
0:53:25 Yeah.
0:53:28 It’s like, it’s the people you can be totally open with and be like, well, that situation’s
0:53:29 effed up.
0:53:30 Yeah.
0:53:33 Someone you can trust and totally be on the ups and downs with.
0:53:34 Totally.
0:53:38 Let’s go to Athena and let’s go where we started, which is sort of the intersection between humans
0:53:39 and AI.
0:53:44 How have you thought about building Athena given sort of developments in AI?
0:53:45 And what does that mean for your future?
0:53:46 Yeah.
0:53:51 So Athena started fully bootstrapped, human only, scaled to a thousand people, no outside
0:53:52 capital.
0:53:59 And then we had this AI moment a few years ago and it was clear we could make a big AI
0:54:04 play and this could become a generational business or we could get railroaded by AI.
0:54:07 And so only one option there is go big.
0:54:12 And our vision here is this, is you take the best of a human and best of a machine, wrap
0:54:14 it into one unified product.
0:54:19 And what the machine does will increase over time, just like a self-driving car.
0:54:23 And so the human’s the UX, it’s on top.
0:54:28 It will become more, the human assistant will focus more on project management and high level
0:54:32 work and really be that like caretaker, the empathy, that partner.
0:54:37 And the machine will increasingly do the more row mechanical administrative stuff.
0:54:42 And, you know, just as when you get into a Tesla, you know, Elon made them with wheels,
0:54:46 or with steering wheels, so you could drive them because they don’t drive themselves when
0:54:47 he started.
0:54:51 But every time you get in the car, you’re actually teaching the machine how to drive.
0:54:52 Yeah.
0:54:54 And these models don’t generalize well.
0:54:56 You have to bring edge cases under distribution.
0:55:00 And so every time you drive, the model gets more powerful.
0:55:03 And the same is true in executive assistant.
0:55:08 Our humans are driving, they’re doing the tasks, but we’re building machine models that are
0:55:10 being improved by the way they act.
0:55:11 Yeah.
0:55:16 And so the more your assistant does tasks for you, the more our models will improve.
0:55:21 And that will allow the human to upgrade what they work on to more high leverage stuff.
0:55:22 Yeah.
0:55:23 That’s exciting.
0:55:28 So what else can you share about plugs for the company or things to watch out for, or for
0:55:30 people who, you know, want to get assistance?
0:55:34 Yeah, look, I just say, if you don’t have an assistant, you are the assistant.
0:55:37 Step one, if you’re starting a business, you should hire an assistant.
0:55:40 And if you’ve got 20 bucks a month, use ChatGPT.
0:55:41 Yeah.
0:55:45 If you’ve got, you know, 10 bucks an hour, go on to Upwork and hire someone yourself.
0:55:49 Uh, if you hire someone yourself, I would say my main recommendation is you need to interview
0:55:50 a lot of people.
0:55:51 Yeah.
0:55:57 Uh, you know, Athena, we have 50,000 assistants apply per month and we put them through a huge
0:55:59 battery of tests and we hire like one in 300.
0:56:03 So if you’re going to hire on yourself, make sure you interview not 10, but probably like
0:56:04 50 people.
0:56:09 Uh, if you have the resources for $3,000 a month, then you should work with a company
0:56:13 like Athena who can recruit, train, manage, and teach you how to delegate.
0:56:19 And then when you have the resources for an in-person assistant, a hundred, 150 K a year,
0:56:20 you should do that as well.
0:56:24 Um, and then ultimately, you know, when you get later stage, you have Achieva staff, in-person
0:56:27 assistant, and you know, a fleet of Athena assistants in the cloud.
0:56:28 Yeah.
0:56:29 That’s a great, a great overview.
0:56:30 Well, let’s wrap on that.
0:56:31 Awesome.
0:56:38 Thanks for listening to this episode of the A16Z podcast.
0:56:43 If you liked this episode, be sure to like, comment, subscribe, leave us a rating or review
0:56:45 and share it with your friends and family.
0:56:49 For more episodes, go to YouTube, Apple podcasts, and Spotify.
0:56:55 Follow us on X at A16Z and subscribe to our sub stack at a16z.substack.com.
0:56:56 Thanks again for listening.
0:56:58 And I’ll see you in the next episode.
0:57:03 As a reminder, the content here is for informational purposes only should not be taken as legal
0:57:08 business tax or investment advice, or be used to evaluate any investment or security, and
0:57:13 is not directed at any investors or potential investors in any A16Z fund.
0:57:17 Please note that A16Z and its affiliates may also maintain investments in the companies discussed
0:57:18 in this podcast.
0:57:25 For more details, including a link to our investments, please see a16z.com/disclosures.