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The Unicorn Founder Who Delegated Everything.

Jonathan Swanson has built two rare successes: Thumbtack, the home-services marketplace, and Athena, the fast-growing platform that pairs ambitious people with world-class personal assistants. Today he runs a 4,000-person company, invests on the side, and raises four kids — all by designing his life around leverage. a16z General Partner, Erik Torenberg, sits down with Jonathan to unpack what that actually looks like. They discuss how elite assistant culture shaped his philosophy, why delegation is a skill most founders never truly learn, and how the combination of humans and AI is redefining personal productivity. Jonathan explains why he believes ambition grows with leverage, not the other way around, and breaks down how he delegates everything from scheduling to search processes to entire life systems. They also get into the future of work, the rise of machine-generated delegation, the expanding role of chiefs of staff, and how founders can design their time around the few things that matter most. It’s a conversation about work, life, and the systems that allow people to operate at scale. Timestamps: 0:00 – Introduction 0:44 – The power of delegation: from the White House to Thumbtack 02:13 – Human vs. AI assistants: the future of delegation 04:30 – Levels of delegation: from tasks to algorithms 06:31 – Principles of effective delegation 07:50 – Delegation & productivity hacks 09:46 – The future: machine-generated delegation 11:36 – Global talent & leveraging international teams 12:33 – Assistants and financial leverage 13:45 – Company culture across borders 15:18 – Assistants as accountability partners 16:52 – Coaching, feedback, and the human element 18:30 – Goal setting, time management, and prioritization 22:07 – Frameworks for founders: time, energy, and meetings 25:06 – The efficient path vs. the effect path 27:19 – Executive hiring: principles and pitfalls 29:19 – Reference check signals 32:09 – Principles for company transparency 35:55 – Cofounder relationships & company building 38:19 – Chief of staff vs. executive assistant 39:06 – Learning from high-performers: Lonsdale, Elon, Thiel, etc. 46:10 – Building your universe: org structures and talent networks 51:33 – Managing founder psychology & staying in the game 55:26 – Athena’s vision: human + AI assistants Resources: Follow Jonathan on X: https://twitter.com/swaaanson Follow our host: https://twitter.com/eriktorenberg Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures](http://a16z.com/disclosures.

Jonathan SwansonguestErik Torenberghost
Dec 10, 202556mWatch on YouTube ↗

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  1. 0:00 – 0:44

    Introduction

    1. JS

      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.

    2. ET

      You're running a massive company. You also do investing. You're also a 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?

    3. JS

      Cardinal sin of delegation is that it will be faster or better to do it myself, and the reason it's a blocker is 'cause it's true. But the only way you get leverage is by going through that work. A couple decades ago, you had to be Marc Andreessen or Vinod Khosla to have a half dozen assistants, and that cost you half a million dollars. Now, with a company like Athena, for 3,000 bucks a month, you can have your own assistant.

    4. ET

      What have you learned in your extensive founder career?

  2. 0:44 – 2:13

    The power of delegation: from the White House to Thumbtack

    1. ET

      Jonathan, welcome to the podcast.

    2. JS

      Thanks for having me.

    3. ET

      So Jonathan, you're running a massive company. What, 4,000 employees all, all-

    4. JS

      4,000.

    5. ET

      4,000 em-employees. You al-also do investing. You're also a, in a, you know, happy marriage with, with four kids. How do you do it all? I know the way that you do it all is delegation. You have a, a chief of staff, a bunch of EAs. Why, why don't you talk about what is the secret that you've figured out that other people can learn from?

    6. JS

      Yeah. So my origin story here is out of school, I worked at the White House, and, uh, I sat, I sat in the West Wing next to the president's executive assistants. And as you might imagine, the EAs in the West Wing were really freaking good, and it set my bar super high for what this EA-client partnership could look like. And when I moved to San Francisco to start Thumbtack, I said, "Okay, I'm not president, but what if I had a EA and support team that was as good as the president's? Like, 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, uh, 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, you know, started with one assistant, now I've got a half dozen.

    7. ET

      Yeah.

    8. JS

      And every assistant gives me more leverage to take on more things.

  3. 2:13 – 4:30

    Human vs. AI assistants: the future of delegation

    1. ET

      It's fascinating 'cause I, um, some people say, "Hey, you know, Bill Gates is so much richer than me, but he has the same phone that I have."

    2. JS

      Mm.

    3. ET

      Or I remember, um, maybe it was you, maybe someone else who was like, "Wait, Obama should have, you know, or the President should have way better information than me, and yet they're, like, reading Politico too."

    4. JS

      Mm-hmm.

    5. ET

      Like, they're reading the same-

    6. JS

      Mm-hmm

    7. ET

      ... newsfeed. And this is, like, another example of it, which is, you know, the democratization where a White House have amazing assistants, but thanks to Athena, you know, and, and tech- you know, technology, at some point everyone will have a certain b-

    8. JS

      Exactly. The, you know, a couple decades ago, you had to be Marc Andreessen or Vinod Khosla to have a, a half dozen assistants, and that cost you half a million dollars. Now, with a company like Athena, for 3,000 bucks a month, you can have your own assistant. And then with AI, yeah, it's gonna become ubiquitous. People are-- 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.

    9. ET

      Yeah. How should we think about what are the things that humans can do versus what are the things that AI can do? I re- you know, I remember my friend started Clara, um, you know, a decade ago, which is trying to be AI assistants of effective absence well before a lot of the innovation.

    10. JS

      Yeah.

    11. ET

      But yeah, what, what is the right way of thinking about sort of the human-AI, you know, relationship?

    12. JS

      Yeah, I mean, it's a moving target, obviously.

    13. ET

      Yeah.

    14. JS

      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, and then over time it becomes more autonomous, and the same thing is gonna happen with assistants. Um, my, 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.

    15. ET

      Yeah.

    16. JS

      Uh, and if you only got 20 bucks a month, you start by delegating to ChatGPT. And prompt engineering is really just delegating.

    17. ET

      Yeah.

    18. JS

      And if you become world-class at leveraging ChatGPT to brainstorm your goals, figure out how, uh, 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 bucks a month. Um, if you have budget, then you hire someone direct-

    19. ET

      Mm

    20. JS

      ... with a service like Athena. If you have enough money, you hire someone in person. That's six figures. You know, and if you're a legendary budget, then you've got a, a suite of assistants and chief of staffs following you around.

    21. ET

      Yeah.

  4. 4:30 – 6:31

    Levels of delegation: from tasks to algorithms

    1. ET

      So I've had, uh, an Athena EA for many years now, and, and she's absolutely amazing. And, um, you know, I use her for scheduling and, um, you know, typical assistant a-a-activities. But you have many assistants. Uh, you know, s- our friend Sam Corcos has, has a bunch of assistants as well.

    2. JS

      Mm-hmm.

    3. ET

      Close the gap between what are the people who do it well, like, you know, what else do people get leverage on-

    4. JS

      Yeah

    5. ET

      ... or delegate that maybe is not obvious?

    6. JS

      So first you start by taking the pain off of your life.

    7. ET

      Yeah.

    8. JS

      So, you know, I never wait on hold.

    9. ET

      Yeah.

    10. JS

      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? Uh, how can I spend more time with my family? What are the things, uh, I actually care to do a lot more of?"

    11. ET

      Yeah.

    12. JS

      Um, and so I start with basic stuff, inbox, calendar, stuff that everyone does, but then I just start experimenting. And so, you know, during the scale-up days of Thumbtack, when we were in a house working all the time, I told Marnie, my assistant, "I don't really have any friends outside of work."

    13. ET

      [chuckles] Yeah.

    14. JS

      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, a founder dinner at my house every other week," and we did lots of these together-

    15. ET

      Yeah

    16. JS

      ... 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... the chef and the bartender, and we walk in and we make new friends. And, you know, I met Catherine, my wife-

    17. ET

      Yeah

    18. JS

      ... through that.

    19. ET

      Yeah.

    20. JS

      And then Marnie's helping plan our wedding, and now Marnie helps us with our kids. And so, you know, it starts small, and then you just kinda compound these things.

    21. ET

      Yeah. But even in that example, um, like say more about how did she know who to reach out to or what, what kind of... Yeah, the-

    22. JS

      Yeah. So the kind of entry-level delegation is you delegate by task. You say, "Help me plan this dinner party." If you just say that, you're not gonna get what you want. Um, the more advanced

  5. 6:31 – 7:50

    Principles of effective delegation

    1. JS

      way to delegate is called delegate by algorithm-

    2. ET

      Yeah

    3. JS

      ... where you actually export your own internal preferences as you delegate. So I would say, "Hey, when I plan dinner parties, I like to have six to eight people. I like people to have raised similar amounts of capital or be at similar stages or similar number of employees."

    4. ET

      Yeah.

    5. JS

      And literally write an algorithm for-

    6. ET

      Yeah

    7. JS

      ... how you find the right people. Um, and then you give feedback on whether-

    8. ET

      Yeah

    9. JS

      ... it worked or not. And once the algorithm's fully exported from your head, then it's just rinse and repeat. And so, you know, engineers tend to be better at creating these kind of like SOPs or standard-

    10. ET

      Yeah

    11. JS

      ... practices, but it's something, yeah, you can learn to do.

    12. ET

      Yeah. And so share more about what, how you-- for people with multiple assistants or-

    13. JS

      Yeah

    14. ET

      ... how do you differentiate? Like, how do you, you know, sort of delegate a-across the team?

    15. JS

      Yeah, I mean, start with one.

    16. ET

      Yeah.

    17. JS

      Uh, and then like any team, you specialize.

    18. ET

      Yeah.

    19. JS

      And so I just had one that did everything as a generalist, and now I have a half a dozen, which I know sounds crazy.

    20. ET

      Yeah.

    21. JS

      But each one specializes in different things. One is on work, one is on home, one is on kids, family-

    22. ET

      Yeah

    23. JS

      ... travel, uh, finances.

    24. ET

      Yeah.

    25. JS

      Um, and, uh, that specialization is helpful 'cause the finance person is just thinking about balance sheet, uh, you know, sending wires, all that sort of stuff.

    26. ET

      Yeah.

    27. JS

      And then, uh, I have a chief of staff who sits on top who distributes work-

    28. ET

      Yeah

  6. 7:50 – 9:46

    Delegation & productivity hacks

    1. JS

      ... across all of them.

    2. ET

      What are other principles, like, you know, I love this-

    3. JS

      Mm-hmm

    4. ET

      ... delegate by algo-algorithm, not, not by task. What are other principles or frameworks that are really important or non-obvious to, you know, get the most out of an assistant?

    5. JS

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

    6. ET

      Yeah.

    7. JS

      That's the number one blocker for most people, and the reason it's a blocker is 'cause it's true.

    8. ET

      Yeah.

    9. JS

      It will actually be faster or better-

    10. ET

      Yeah

    11. JS

      ... if you do it yourself that first time.

    12. ET

      Yeah.

    13. JS

      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.

    14. ET

      Yeah.

    15. JS

      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, 12 months, but it's the compounding that creates incredible leverage. I've been working with Marnie for a decade, like a little sister now, and she knows everything about me. Um, so that's just kinda like common principles. Um, in terms of the way to delegate, I think the, this is just tactical, the methods. You know, the most common way people delegate is with your thumbs on your phone. That's the worst way, very slow. Um, better to use all 10 fingers at a computer, but that's actually pretty slow as well. The best way to really delegate is using your voice. And so voice, you can talk two to three times faster. You can do it on the go. You can do it on a date, [chuckles] between lunch, you know, in the Uber. Um, you know, at Thumbtack during hyperscale times, I would walk between meetings, and between a meeting I would be voice noting to-

    16. ET

      Yeah

    17. JS

      ... an assistant, "Here's the takeaways. Pre-draft these five emails."

    18. ET

      Yeah.

    19. JS

      "Uh, 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-

    20. ET

      Right

    21. JS

      ... and then you get to the end of the day and you're like, "I have a hundred things to do."

    22. ET

      Yeah.

    23. JS

      And so learning to delegate by voice, uh, if you look at all the super delegators at Athena, they are all just delegating by voice all day long.

    24. ET

      Right.

  7. 9:46 – 11:36

    The future: machine-generated delegation

    1. ET

      Yeah, it's fascinating. Uh, well, at some point it's gonna be, you know, not on- I don't even have to say it, I just think it.

    2. JS

      Mm-hmm.

    3. ET

      [laughs] Uh, yeah.

    4. JS

      This is, uh, this is part of our vision-

    5. ET

      Yeah

    6. JS

      ... at Athena longer term is you shouldn't have to actually vocalize it.

    7. ET

      No.

    8. JS

      And we've built an internal demo of this. It's, uh, uh, it's not live, uh, 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, Erik 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.

    9. ET

      Right.

    10. JS

      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.

    11. ET

      Yeah.

    12. JS

      He's not talking. He's just working, and the machine is magically pulling tasks and putting it on his assistant's plate. Uh, it'll take a while to bring that to market and fruition, but that's the, that's the future.

    13. ET

      There should also be-- Relatedly, there should also be a version where it's like, you know, you see in Slack that it's, you know, it's someone's birthday or someone has a baby or something, and it suggests, "Hey, do you wanna-

    14. JS

      Yep

    15. ET

      ... you know, get this person this, this specific gift or something?"

    16. JS

      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 at Athena is, like, the best human assistant, the best AI wrapped into one combined, uh, product that's seamless. And humans obv-obviously have human touch and good UX, uh, but what machines can do is remember everything and be super proactive.

    17. ET

      Yeah.

    18. JS

      So it can look through every email, every calendar, and remind you to do things that you would not have thought to do otherwise.

    19. ET

      Yeah. One thing

  8. 11:36 – 12:33

    Global talent & leveraging international teams

    1. ET

      you've always been fascinated about is sort of, um, international labor-

    2. JS

      Mm-hmm

    3. ET

      ... some call it, you know, lab-labor arbitrage. What is the right way of thinking about what people in, say, the Philippines, um, can do or can't do versus, you know, assistants in the US? Like, how, how do people-- 'cause obviously there's a huge cost savings. Um, what, what, what are stuff that you keep in that cost savings or stuff that you don't keep, or, like, what's the right way of thinking?

    4. JS

      Yeah. I mean, America's strength is entrepreneurship, capital, innovation, technology, and, um, the more you can leverage someone to do back office tasks, the more you can spend on technology, product, et cetera. So, you know, I think the, the thing Athena focuses on is executive assistants, someone who can do all of this admin. Um, but people, uh, are using global talent for all sorts of things-

    5. ET

      Yeah

    6. JS

      ... for legal, medical, um, all the above.

    7. ET

      Yeah. So-Let, let's get a little bit, I mean we-- um, on

  9. 12:33 – 13:45

    Assistants and financial leverage

    1. ET

      the finance thing I'm, I'm curious because I, I don't leverage mine there. What, what are the ways that people could get leverage from this as on fi- 'cause are you, are you still interfacing with, with the accountants or are they do- yeah, what is the right way of thinking about it?

    2. JS

      Yeah, so I, the first thing I would recommend if, uh, you're getting an assistant, uh, is to have them help you save money.

    3. ET

      Yeah.

    4. JS

      Uh, if you have a big budget, not a big deal, but the first project can be, "Hey, help pay for your salary-"

    5. ET

      Yeah

    6. JS

      "... by looking through all my subscriptions."

    7. ET

      Right.

    8. JS

      "Finding things to sa- uh, save me money. Find me refunds." Um, so that's just kind of like a cost-saving bucket. Um, then there's admin, paying bills.

    9. ET

      Yeah.

    10. JS

      Um, and then there's coordination, which is what you're talking about, basically being a PM. So coordinating, you know, the tax attorney-

    11. ET

      Yeah

    12. JS

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

    13. ET

      Yeah

    14. JS

      ... uh, systems, um, at enough scale and complexity that becomes effectively a full-time job. And obviously you need someone you truly trust, uh-

    15. ET

      Yeah

    16. JS

      ... to go deep with, and we kinda recommend that you build this trust over time, and-

    17. ET

      Yeah

    18. JS

      ... you know, you give email and calendar access at first and bank account later.

    19. ET

      [chuckles]

    20. JS

      Uh, but as you earn that trust, then the more access you give effectively-

    21. ET

      Yeah

    22. JS

      ... the more leverage you get.

    23. ET

      Yeah. The, um, yeah, that's really interesting. And, and

  10. 13:45 – 15:18

    Company culture across borders

    1. ET

      in terms of, um, saying more about what it's been like to scale this company where you have, and, you know, you dealt with this Thum- Thumbtack too a, 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, the challenges or what, what's really important to get right?

    2. JS

      Yeah. Um, yeah, I mean, we, we look for cultures that have a strong affinity, uh, to American culture. Uh, you know, Philippines has a long history with America. They, like, know American pop culture and sports-

    3. ET

      Yeah

    4. JS

      ... better than I do. [chuckles]

    5. ET

      Yeah.

    6. JS

      Um, and then they have a very strong work ethic, and, uh, it's a caretaking-

    7. ET

      Yeah

    8. JS

      ... um, culture. So there's lots of nurses, and one of the reasons we picked it for assistants is being an executive assistant is really taking care of someone.

    9. ET

      Yeah.

    10. JS

      It's like their full-time job is to make your life better, is to take things off your plate-

    11. ET

      Yeah

    12. JS

      ... to help you be successful. And I think one of the, uh, barriers for some people to get an assistant is it feels indulgent.

    13. ET

      Yeah.

    14. JS

      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.

    15. ET

      Yeah.

    16. JS

      And for the people on our team, like they get to work with the CEO. They get to see behind this exciting startup that, um, is a totally different life than they live.

    17. ET

      Yeah.

    18. JS

      And for them, that is a cool, exciting, life-changing thing.

    19. ET

      Yeah.

  11. 15:18 – 16:52

    Assistants as accountability partners

    1. ET

      One thing that I think people should be using assistants more for is, uh, is not only delegation but also accountability.

    2. JS

      Mm-hmm.

    3. ET

      Of like, hey-

    4. JS

      Mm-hmm

    5. ET

      ... 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 some- or something.

    6. JS

      Yeah. 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.

    7. ET

      Yeah.

    8. JS

      And that's the place where human accountability is a little more powerful than-

    9. ET

      Yeah

    10. JS

      ... machine accountability.

    11. ET

      Yeah.

    12. JS

      ChatGPT actually has a feature now where it will automatically ping you on things.

    13. ET

      Yeah.

    14. JS

      So if you can't afford an assistant, you just tell ChatGPT, "Here's my top five goals. Ask me how I'm doing every day, log my results, and give me feedback." You can get that for 20 bucks a, a, a month. Um, I've done similar versions of this with a human assistant. I think we may have done this in the past-

    15. ET

      Yeah

    16. JS

      ... where I'm like, "Hey, I wanna work out, meditate, eat clean."

    17. ET

      Yeah.

    18. JS

      "Send me a, 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-"

    19. ET

      Yeah. [chuckles]

    20. JS

      "... Catherine, and we can have a little competition-"

    21. ET

      Yeah.

    22. JS

      "... with it." And yeah, helping you, helping you hit your goals is exactly what they should be doing.

    23. ET

      Yeah. And then the other thing I think is, uh, an interesting opportunity to get more leverage, because th-these people are also, you know, um, not just operationally savvy, but also, you know, pretty, you know, uh, intuitive.

    24. JS

      Mm-hmm.

    25. ET

      You know, they go into caring fields. And so there's also, like, opportunities for coaching too or, like-

    26. JS

      Mm-hmm

    27. ET

      ... they're, you know, they're the

  12. 16:52 – 18:30

    Coaching, feedback, and the human element

    1. ET

      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?

    2. JS

      Yeah, the-

    3. ET

      Yeah.

    4. JS

      That was my first observation, uh, when I was in the West Wing. The assistants who sat next to the president were insane.

    5. ET

      Yeah.

    6. JS

      They were so good. They went on to become, like, elected to Congress and-

    7. ET

      Yeah

    8. JS

      ... 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?"

    9. ET

      Yeah.

    10. JS

      And it was, it was more than just accomplishing things.

    11. ET

      Yeah.

    12. JS

      This was their closest confidant who saw behind the scenes on everything.

    13. ET

      Yeah.

    14. JS

      They knew the good and the bad. They know [chuckles] they'd gotten kicked in the nuts a couple times that day-

    15. ET

      Yeah

    16. JS

      ... from different things, and they're there for them.

    17. ET

      Yeah.

    18. JS

      And I think that human element is gonna remain important for a long time, no matter how, uh, good AI gets, and it's something you should lean into. We have-

    19. ET

      Yeah

    20. JS

      ... uh, clients who tell us that, yeah, like going through a divorce or-

    21. ET

      Yeah

    22. JS

      ... a depression, and, like, my assistant's, like, there for me-

    23. ET

      Yeah

    24. JS

      ... in a way that others aren't, and, like, I can't tell my company or-

    25. ET

      Right

    26. JS

      ... my team about some of these things, but it's, uh, this is the person that's, like, on the inside with you.

    27. ET

      Yeah. Totally. Relatedly, one of the things you've had really interesting insights on over the years is, uh, is how to spend time.

    28. JS

      Mm.

    29. ET

      Think about ti-time management, not, not only in terms of ways to get more of it vi-via delegating, but also, you know, how, how to prioritize. And, you know, I've, I've learned this fr-from you, but y-you think about goals on a sort of, you know, annual, quarterly, you know, like on different increments.

  13. 18:30 – 22:07

    Goal setting, time management, and prioritization

    1. ET

      Why don't you, maybe, maybe we could start with LBD and how, how you think about goal-

    2. JS

      Yeah

    3. ET

      ... goal setting in, in general, and then we can, you know, dive a bit deeper.

    4. JS

      I mean, my wife Catherine and I, who, uh, we met as friends, wanted, you know, develop this friendship up from 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 they're Fortune 500 CEOs, super rich, and their lives are in shambles. [chuckles]

    5. ET

      Yeah.

    6. JS

      They're divorced, have all these problems. The kids don't talk to them, going to jail.

    7. ET

      [chuckles]

    8. JS

      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 Katherine 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."

    9. ET

      Yeah.

    10. JS

      "Let's freaking do that."

    11. ET

      Yeah.

    12. JS

      And so we just started a tradition a decade ago. Every quarter, we get together, we fill out a survey on our relationship, uh, strengths and weaknesses, kinda SWOT analysis-

    13. ET

      Yeah

    14. JS

      ... geeky stuff, and then we talk about, like, what can we improve? Uh-

    15. ET

      Yeah

    16. JS

      ... what can we do better? And like anything, if you-- the more you invest, the better it gets.

    17. ET

      Yeah. Totally. And yeah, I think that's a key point, 'cause some people are turned off by sort of like, uh, quantification. Like, they want their relationship to be a place to like, you know, relax or turn off or something.

    18. JS

      Mm-hmm.

    19. ET

      And I think it's less that you have to like, you know, quantify every element of it a-and more just that you wanna pri- you, you don't wanna 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 wanna be.

    20. JS

      Exactly. It's, uh, be purposeful. Get the thing you want.

    21. ET

      Yeah.

    22. JS

      If you're a geek like us, then you measure it and you track everything. [chuckles]

    23. ET

      Yeah.

    24. JS

      Uh, and if you just wanna go have, like, a date and drink wine-

    25. ET

      Yeah

    26. JS

      ... 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-

    27. ET

      Yeah

    28. JS

      ... for my relationship?

    29. ET

      Yeah. Having been in many goal-setting sessions with you, o-one of the things I think that you in-intuitively understand or, 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-

    30. JS

      Mm-hmm

  14. 22:07 – 25:06

    Frameworks for founders: time, energy, and meetings

    1. ET

      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-

    2. JS

      I mean, high level is Brian Johnson wants to break the chains of biology or longevity.

    3. ET

      Yeah.

    4. JS

      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. 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.

    5. ET

      Yeah.

    6. JS

      And so for different-- This means different things for different people. If you are in hardcore scale mode, that may mean half-hour meetings for 14 hours a day-

    7. ET

      Yeah

    8. JS

      ... 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-

    9. ET

      Yeah

    10. JS

      ... 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.

    11. ET

      Yeah.

    12. JS

      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.

    13. ET

      Yeah. I remember, uh, Keith Rabois shared with me this idea of, like, at the end of every week, do a calendar audit of the past week.

    14. JS

      Mm-hmm.

    15. ET

      Like, what are the meetings you had that you wish you wouldn't have?

    16. JS

      Yeah.

    17. ET

      And then just look at the next one.

    18. JS

      I mean, this is a place, uh, a, you know, Athena assistants can do this proactively for you, but this is a place that AI is obviously gonna automate-

    19. ET

      Yeah

    20. JS

      ... and will be very powerful, where it's at the end of it each week, it just tells you, "Here's what you prioritized."

    21. ET

      Yeah.

    22. JS

      "Are those actually your goals?"

    23. ET

      Yeah.

    24. JS

      If not, then next week-

    25. ET

      Right

    26. JS

      ... we should adjust those things.

    27. ET

      Yeah. I'm curious for your interpretation of meetings. Some people are like-

    28. JS

      Yeah

    29. ET

      ... uh, you know, "I, I wanna have as few meetings as possible. It means not the most efficient. I'd rather do everything async."

    30. JS

      Yeah.

  15. 25:06 – 27:19

    The efficient path vs. the effect path

    1. ET

      interest- You know, um, um, one of my favorite self-help books is the seven effective habits-

    2. JS

      Yeah

    3. ET

      ... of highly effective people, and one of their, y-y-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.

    4. JS

      Mm.

    5. ET

      And, and so, um-You know, the efficient path might not be the effect path-

    6. JS

      Mm-hmm

    7. ET

      ... 'cause you might, you 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.

    8. JS

      Yeah.

    9. ET

      And, um, yeah, it might be efficient to just send a text or something, but, you know, keeping the dynamic... Yeah, yeah, phone calls are obviously under- underrated and-

    10. JS

      Yeah.

    11. ET

      Yeah.

    12. JS

      It's true remote cultures too.

    13. ET

      Yeah.

    14. JS

      Like remote cultures build up debt of just-

    15. ET

      Yeah

    16. JS

      ... the lack of bandwidth, and so if you are in a remote cul- culture, you should get together every couple months for-

    17. ET

      Yeah

    18. JS

      ... a, a few days in person.

    19. ET

      Totally. H- 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... Ob- obviously, there's a million things they could be doing. There's not enough time-

    20. JS

      Yeah

    21. ET

      ... in the day for, you know, even a fr- fraction of them. What, what are the most important ways to, to get right whether it's your time at Thumbtack or Athena?

    22. JS

      Yeah, I mean, it's, like it's build your product, who's your customers, raise capital, build your team.

    23. ET

      Yep.

    24. JS

      And 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 month?"

    25. ET

      Yeah.

    26. JS

      If it's recruiting, uh, you have to be closing candidates.

    27. ET

      Yeah.

    28. JS

      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."

    29. ET

      Yeah.

    30. JS

      "Here's... Let me go through my contacts. Here's 20 people. Send an outreach email asking them for suggestions for this role." Uh, you know, if your goal is to raise capital-

  16. 27:19 – 29:19

    Executive hiring: principles and pitfalls

    1. JS

      we first started it, we were like, "We're just gonna hire the best assistants, match them with clients, and boom."

    2. ET

      Right.

    3. JS

      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-

    4. ET

      Yeah

    5. JS

      ... how to delegate, uh, because that is as much of a constraint as the assistants. And we've got a few thousand, uh, assistants and clients, and if you look at the best performing assistants at Athena, they work for the best delegators.

    6. ET

      Mm.

    7. JS

      It's not a coincidence. [chuckles]

    8. ET

      Yeah.

    9. JS

      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, uh-

    10. ET

      Yeah

    11. JS

      ... struggle with that and need more training.

    12. ET

      Yeah. One, one thing that you've been phenomenal at is, whether it's Thumbtack or Athena, is, is hiring executives. What, 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?

    13. JS

      I mean, one thing that is obvious as you hire execs is the more senior they go, the m- better they are at interviewing, at 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 rev- uh, uh, 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 360 reviews. 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 you, share mine. You show me yours." I actually think this would be a cool kind of reference pro- startup, um, 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-

    14. ET

      Right

    15. JS

      ... be pretty good-

    16. ET

      Yeah

    17. JS

      ... when you get to the senior level.

    18. ET

      That's interesting. What's

  17. 29:19 – 32:09

    Reference check signals

    1. ET

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

    2. JS

      I mean, what I often tell people is, "Hey, I'm probably gonna hire this person. Uh, and now tell me all the things you don't like about them." [chuckles]

    3. ET

      Yeah.

    4. JS

      "Or things that they could be better at."

    5. ET

      Yeah.

    6. JS

      'Cause if, you know, people are so biased to just tell you all the good things, you have to get them to, uh, to s- 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.

    7. ET

      Yeah. One, one question I like to ask is, um, "What skill sets would be really important to complement this person with?"

    8. JS

      Mm.

    9. ET

      Um, which is another way of just saying, what are they bad at?

    10. JS

      Yeah.

    11. ET

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

    12. JS

      Yeah. And, I mean, the best way to source talent, um, I just hired an executive recently, is just ask the people that you respect the most, that have the highest standards, who's the best person? [chuckles] 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.

    13. ET

      Yeah.

    14. JS

      And that is the, like, speed rapid way to hire an exec.

    15. ET

      Yeah.

    16. JS

      Um, you know, using an exec recruiter, you spend three months. You get all those cold leads, but going through a network of high bar people is-

    17. ET

      Yeah

    18. JS

      ... super efficient.

    19. ET

      There's some maxim that almost, like, half of executives, you know, don't work out within, like, a-

    20. JS

      Mm-hmm

    21. ET

      ... you know, 12 to 24-month period.

    22. JS

      Checks out. [chuckles]

    23. ET

      Yeah. W- why is that?

    24. JS

      I think it's this, it's difficult to, uh, judge, uh... The, 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. Um, 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 'cause 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-

    25. ET

      Mm-hmm

    26. JS

      ... to what the work they're doing in lots of cases.

    27. ET

      Yeah. Yeah, and K- Keith has this maxim that that's like, um, you c- you're, you're not gonna get 100% hiring in the same way you're not gonna get 100% investing. And if-

    28. JS

      Yeah

    29. ET

      ... you know, like, you also wanna avoid the, you know-Of not... The p- uh, trap of not taking enough risk or moving too slow or

    30. JS

      Yeah, and as long as you cut your losses quickly, it's okay. It's w- if you, like, don't cut losses, then you compound a hole-

  18. 32:09 – 35:55

    Principles for company transparency

    1. ET

      your stance on, um, 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, uh, employees to know? Or like what, what are principles like that guide, you know, how much you share?

    2. JS

      Yeah, I mean, default transparency's obviously the best, but there's o- obviously some lines.

    3. ET

      Yeah.

    4. JS

      I... 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." I was like, "What?"

    5. ET

      Yeah.

    6. JS

      And I went to Google. You type in Thumbtack, and nothing shows up, and we basically received the death penalty from Google. Uh, there was a misunderstanding. They thought we'd done something wrong, but they, like, eliminated us from the internet, and so our traffic went to zero [chuckles] 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 it's their first day, and I'm supposed to do the onboarding with them. There's a journalist, like, walking around outside trying to get a quote. And, you know, that's one of those times where you can't share everything. And so, uh, you want to ultimately be transparent, but if I just walked into a new class and say, [chuckles] "The business might be dead," uh, that's not gonna work. And so you have to kinda 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-

    7. ET

      Right

    8. JS

      ... in place, then the whole company, uh, is told.

    9. ET

      Yeah. No, that, that makes sense. Um, 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. Um, I feel like it's pretty rare when I think about cofounding teams that it feels like the non-CEO, especially if you're not a CTO, usually that doesn't last, you know, over five years or something.

    10. JS

      Mm-hmm.

    11. ET

      Um, I'm curious what's really important to get right in, in cofounder relationships-

    12. JS

      Mm-hmm

    13. ET

      ... or how you think about advising, you know, companies you invest in.

    14. JS

      Yeah, I mean, the, uh, I heard Sir Michael at Sequoia say something that was like, "There's only one founder."

    15. ET

      Yeah.

    16. JS

      And it was at... He said it at a founder event, and I was like, "That's rude." [both chuckling] There's lots of cofounders here. And now a decade later, I'm like, of course, there is only one cofounder that goes the distance-

    17. ET

      Yeah

    18. JS

      ... because ultimately, as you scale the org, it only makes sense to have one person on top.

    19. ET

      Yeah.

    20. JS

      Um, so I think that's just the reality, and, uh, you know, it, it's good to know that-

    21. ET

      Yeah

    22. JS

      ... going into starting a business. Uh, in terms of who to pick, my advice is you pick someone you wanna get married to.

    23. ET

      Yeah.

    24. JS

      And you're gonna have all the same relationship issues you have- [chuckles]

    25. ET

      Yeah

    26. JS

      ... with a partner. Uh, you know, no makeup sex, but it's still like-

    27. ET

      [chuckles]

    28. JS

      Uh, yeah, there's highs, lows-

    29. ET

      Yeah

    30. JS

      ... and you want someone that ultimately you s- you really deeply trust 'cause there's gonna be stress and-

  19. 35:55 – 38:19

    Cofounder relationships & company building

    1. ET

      got into GSB, and you were gonna go to grad school.

    2. JS

      Mm-hmm.

    3. ET

      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.

    4. JS

      Mm-hmm.

    5. ET

      You just thought it'd be a, a good business, and you, uh, emailed the, you know... You let the GSB people know you weren't going to accept it, and, and they sent you back this very moralizing email-

    6. JS

      Mm-hmm

    7. ET

      ... of how you're making the biggest mistake in your life.

    8. JS

      Mm-hmm.

    9. ET

      Um, et, et, et cetera. You know, it turned out pretty good. But h-how do you... Pretty good decision. Um, how did you at the time think about get enough conviction to, to take the leap and do it?

    10. JS

      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. I probably might need to get a, a nice paying job afterwards.

    11. ET

      Yeah.

    12. JS

      And if I was gonna 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."

    13. ET

      [chuckles]

    14. JS

      He said something like, uh, "You can... Startups will come and go, but you can only come to Stanford once," or something.

    15. ET

      [laughs]

    16. JS

      "This is a once in a lifetime opportunity." I never responded, and I have it as a email in my, the saved that I'm just gonna respond to whenever Thumbtack goes public and be like-

    17. ET

      [laughs]

    18. JS

      ... "I made the right decision."

    19. ET

      [laughs]

    20. JS

      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.

    21. ET

      Yeah, totally. Okay, so there's EAs, and then there are chi- chiefs of staffs.

    22. JS

      Mm-hmm.

    23. ET

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

    24. JS

      Mm-hmm.

    25. ET

      Um, but seems hard to find the right person.

    26. JS

      Yeah, there's no formal definition. I think it's something that, uh, an EA is typically more administrative-

    27. ET

      Yeah

    28. JS

      ... and taking things off your plate, and a chief of staff is more offensive.

    29. ET

      Yeah.

    30. JS

      And 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, uh, today. Go figure out how to solve it." And so a chief of staff typically has the capabilities to become a founder themselves, and the only reason [chuckles] 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. So you kinda get people who do more tours of duty, and you get super high capability, uh, but you don't get the same longevity-

  20. 38:19 – 39:06

    Chief of staff vs. executive assistant

    1. ET

      in chief of sta- or what, what's sort of the right... You know, there's sort of this tension between, you know, getting someone younger who's, you know, definitely initially gonna d-

    2. JS

      Mm-hmm

    3. ET

      ... do it for, for a couple years, um, and is more ambitious ver- versus someone who's been more seasoned, but maybe-

    4. JS

      Yeah

    5. ET

      ... not as high slope or something. W- w- how do you think about?

    6. JS

      The way I break it down is assistant, you find someone you wanna go a decade with. Uh, the intimacy and the compounding of that relationship is super important.

    7. ET

      Yeah.

    8. JS

      And so you go deep, and that means you probably don't find a founder because they're-

    9. ET

      Yeah

    10. JS

      ... not gonna be excited to do this. It's someone who's much more of a caretaker and is-

    11. ET

      Yeah

    12. JS

      ... excited to be number two. And then a chief of staff, I do pure slope, where you know the person's gonna move on in a couple-

    13. ET

      Yeah

    14. JS

      ... years, but they have... Yeah, they could start a business, but instead you get them by your side-

    15. ET

      Yeah

    16. JS

      ... to help solve problems.

    17. ET

      Totally. And there, there

  21. 39:06 – 46:10

    Learning from high-performers: Lonsdale, Elon, Thiel, etc.

    1. ET

      are people, you know, like Lonsdale, maybe like Elad or something, who have, you know, chief of staff for like a year or two, and then they start a company, then they invest in them.

    2. JS

      Mm-hmm.

    3. ET

      And they build kind of this reputation for, for doing, and then they have sort of these like, you know, um, alumni almost-

    4. JS

      Mm-hmm

    5. ET

      ... the chief, the chief of staff just kind of, you know, Peter Thiel's or just kind of further-

    6. JS

      Yeah, Bezos has this.

    7. ET

      Yeah.

    8. JS

      Someone follows him around-

    9. ET

      Yeah

    10. JS

      ... that goes to every meeting.

    11. ET

      Yeah.

    12. JS

      And yeah, it's cool.

    13. ET

      Yeah. Let, let's talk about some, some people who get an enormous amount done, and I'm curious what are lessons-

    14. JS

      Hmm

    15. ET

      ... that we can draw from them. Wh- 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 s- 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-

    16. JS

      Yeah

    17. ET

      ... someone like Lonsdale. Thiel has done this really well. They sort of compound these certain talent networks.

    18. JS

      Mm-hmm.

    19. ET

      So, you know, whether it's like Stanford Review or just Sta- Stanford in general, um, they're often hiring people from there and then involved in sort of these talent pipelines. They've sort of, you know, created to, you know, they're deep in the hackathon scene.

    20. JS

      Yeah.

    21. ET

      But they just kind of build this proprietary compounding sort of talent base that they're constantly-

    22. JS

      Yeah

    23. ET

      ... you know, sort of, um, seeing talent.

    24. JS

      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, uh, you're very much this way of like, "Well, what if I could do 10 times more things?"

    25. ET

      Yeah.

    26. JS

      And I think lots of people, uh, just think that's impossible.

    27. ET

      Yeah.

    28. JS

      Um, but it's not. It is possible, and, uh, 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, uh, people of, uh, great power or wealth or, uh, resources can afford this team.

    29. ET

      Yeah.

    30. JS

      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.

  22. 46:10 – 51:33

    Building your universe: org structures and talent networks

    1. JS

      It's like what's the right org structure?

    2. ET

      Yeah.

    3. JS

      There's actually no right org structure. It's what's the right org structure for you as a founder.

    4. ET

      Yeah, yeah.

    5. JS

      And, you know, Marc Andreessen and Ben Horowitz are company builders, and so they're building their leverage like a company. The a16z is a company. Uh, not that Peter Thiel is not an entrepreneur, but he's more of a philosopher today, and so his, uh, system is more like a philosopher. It's all these kinda wild and crazy ideas. Uh, and so I think, you know, Jensen Huang has, like, 46 direct reports or something-

    6. ET

      Yeah

    7. JS

      ... which is absolutely insane.

    8. ET

      Yeah.

    9. JS

      But it works for him. And so I think you just have to know what your style is-

    10. ET

      Yeah

    11. JS

      ... and then you build it for you.

    12. ET

      Totally. And someone like, you know, Sam Altman is, like, a deal maker and a fundraiser-

    13. JS

      Mm-hmm

    14. ET

      ... and a talent identifier, you know?

    15. JS

      Mm-hmm.

    16. ET

      And so he's able to... Like, I remember he was at YC, and he was talking to my f- one of my friends about sort of this universal basic income company. My friend didn't end up doing it, but I was like, "Huh, that's interesting. Why is, why is he even doing that?" He's, like, focused on YC.

    17. JS

      Yeah.

    18. ET

      And he's like, he wa- he has a knack for, for good ideas. He has a knack for... And this person was, like, 22. He has a knack for, you know, uh, high-slope talent, and he has a superpower around raising money.

    19. JS

      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?"

    20. ET

      Yeah.

    21. JS

      But then a second-time founder is like, "Forget [chuckles] all my weaknesses. I'm just not even gonna try."

    22. ET

      Yeah.

    23. JS

      "I'm just gonna be really good at my strengths-"

    24. ET

      Yeah, triple down, yeah.

    25. JS

      "... and I'm gonna hire other people to do all the things I'm not good at." And that is way more effective.

    26. ET

      Yeah, totally. The, um, 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 cofound- or the founder.

    27. JS

      Mm-hmm.

    28. ET

      They have to drive it too. W- where do you stand on, on kind of that, that debate?

    29. JS

      I think the biggest companies aren't incubated-

    30. ET

      Yeah

  23. 51:33 – 55:26

    Managing founder psychology & staying in the game

    1. ET

      What have you learned in your extensive founder career about, uh, managing your own psychology, dealing with stress-

    2. JS

      Mm

    3. ET

      ... dealing with the cognitive dissonance of, you know, having to present externally-

    4. JS

      Mm

    5. ET

      ... like things are amazing even when, you know, you're concerned about Google-

    6. JS

      Mm-hmm

    7. ET

      ... you know, taking out your business. Um, what, um, what advice might you have for others in terms of cultivating this, uh, skill set?

    8. JS

      Yeah, I mean, I think it's like, uh, a cold plunge or something. It's just you, just shock therapy and eventually-

    9. ET

      Yeah

    10. JS

      ... you, it's just like you're bathing in existential fear-

    11. ET

      Yeah

    12. JS

      ... all the time and you're like, "Whatever."

    13. ET

      Yeah.

    14. JS

      "Just bring it on." [chuckles]

    15. ET

      Totally.

    16. JS

      Uh, 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 s- uh, 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 was like, you just gotta stay in the game.

    17. ET

      Yeah.

    18. JS

      And if you can stay in the game-

    19. ET

      [chuckles]

    20. JS

      ... you can eventually win.

    21. ET

      Yeah.

    22. JS

      And I think Thumbtack was very good at staying in the game so that we can eventually win. Um...

    23. ET

      Yeah. It's funny, there's like degrees of panic. In the beginning, you know, you're getting your feet wet. It's like, oh my God, someone said something mean about me on the internet.

    24. JS

      [chuckles]

    25. ET

      And then it's like, oh my God, someone wants to, like, leave my company.

    26. JS

      [chuckles]

    27. ET

      But then it's like, oh my God, um, we're getting, we're, you know, we might die. [chuckles] We only have-

    28. JS

      Yeah, it's like the-

    29. ET

      ... six months of payroll. Then it's like, oh my shit, we're gonna get sued. [laughs]

    30. JS

      Yeah.

  24. 55:26 – 56:47

    Athena’s vision: human + AI assistants

    1. ET

      what else, uh, can you share about plugs for the company or things to watch out for, or for people who, you know, wanna get assistants with, you know?

    2. JS

      Yeah, look, uh, I just say if you don't have an assistant, you are the assistant.

    3. ET

      Yeah.

    4. JS

      Step one, uh, if you're starting a business, you should hire assistant. And if you've got 20 bucks a month, use ChatGPT.

    5. ET

      Yeah.

    6. JS

      If you've got, you know, 10 bucks an hour, go onto Upwork and hire someone yourself. Uh, if you hire someone yourself, I would say my main recommendation is you need to interview a lot of people.

    7. ET

      Yeah.

    8. JS

      Uh, you know, at Athena we have 50,000 assistants apply per month, and we put them through a, 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.

    9. ET

      Yeah.

    10. JS

      Uh, 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-

    11. ET

      Yeah

    12. JS

      ... uh, 100, 150K a year, you should do that as well. Um, and then ultimately, you know, when you get later stage, you have a chief of staff-

    13. ET

      Yeah

    14. JS

      ... in-person assistant, and, you know, a fleet of-

    15. ET

      Yeah

    16. JS

      ... Athena assistants in the cloud.

    17. ET

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

    18. JS

      Awesome.

    19. ET

      The a16z Podcast. [outro music]

Episode duration: 56:49

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