The a16z Show - How the Best CEOs Delegate

Episode Date: December 10, 2025

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.Timecodes0:00 – Introduction1:52 – The power of delegation: from the White House to Thumbtack03:13 – Human vs. AI assistants: the future of delegation05:30 – Levels of delegation: from tasks to algorithms07:31 – Principles of effective delegation08:50 – Delegation & productivity hacks10:46 – The future: machine-generated delegation12:36 – Global talent & leveraging international teams13:33 – Assistants and financial leverage14:45 – Company culture across borders16:18 – Assistants as accountability partners17:52 – Coaching, feedback, and the human element19:30 – Goal setting, time management, and prioritization23:07 – Frameworks for founders: time, energy, and meetings26:06 – The efficient path vs. the effect path28:19 – Executive hiring: principles and pitfalls30:19 – Reference check signals 33:09 – Principles for company transparency36:55 – Cofounder relationships & company building39:19 – Chief of staff vs. executive assistant40:06 – Learning from high-performers: Lonsdale, Elon, Thiel, etc.47:10 – Building your universe: org structures and talent networks52:33 – Managing founder psychology & staying in the gameResources:Follow Jonathan on X: https://x.com/swaaansonFollow 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/a16zFind a16z on LinkedIn: https://www.linkedin.com/company/a16zListen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYXListen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711Please 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 http://a16z.com/disclosures. Stay Updated:Find a16z on YouTube: YouTubeFind a16z on XFind a16z on LinkedInListen to the a16z Show on SpotifyListen to the a16z Show on Apple PodcastsFollow our host: https://twitter.com/eriktorenberg 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. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Brian Johnson wants to break the chains of biology. I want to break the chains of time. We can always raise another round or do another trade, but you can't raise another decade. You're running a massive company. You also do investing. You're also happy marriage with four kids. I know the way that you do it all is delegation. What is the secret that you've figured out?

Cardinal sin of delegation is that it will be faster or better to do it myself. And the reason it's a blocker is because it's true. But the only way you get leverage is by going through that work. A couple decades ago, you had to be Mark and Driesen, Irvine Coasta, to have a half a dozen assistants, and that cost you half a million dollars. Now with a company like Athena for $3,000 a month, you can have your own assistant. What have you learned in your extensive founder career? Most people think about delegation as a convenience.

Jonathan Swanson thinks about it as a system for living and has built its career around a simple idea. If you don't have an assistant, you are the assistant. He scaled Bumptack into one of the major home services marketplaces for the last decade. Now he's doing it again with Athena, the number one place to hire a personal assistant who can run your calendar, your operations, your home, and increasingly your AI workflows. Jonathan is running a 4,000-person company while investing on the side and raising four kids. The through line is a very intentional philosophy of time. He believes most people underestimate how much ambition they unlock when they learn to delegate well.

In this conversation, we talk about how elite assistants. culture shaped him. What founders consistently get wrong about leverage and why he thinks billions of people will soon be delegating to a mix of human and AI partners. We get into delegation frameworks, splitting work across multiple assistants, how chief of staffs fit in, and the mindset shift required to stop optimizing for speed today and start optimizing for compounding tomorrow. We hope you enjoy. Jonathan, welcome to the podcast. Thanks for having me. So Jonathan, you're running a massive company, what, 4,000 employees? 4,000. 4,000 employees. You also do investing. You're also happy marriage with four kids. How do you do it all?

I know the way that you do it all is delegation. You have a chief of staff, a bunch of EAs. Why don't you talk about what is the secret that you've figured out that other people can learn from? Yeah. So my origin story here is out of school. I worked the White House and I sat in the West Wing next to the president's executive assistance. And as you might imagine, the EA's in the West Wing were breaking 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 a Thumbtack, I said, okay, I'm not president, but what if I had an EA and support team that was as good as the president? What could I accomplish?

And so at Thumbtack, as we were scaling the business, I hired my first assistant in the Philippines, started helping me with basic stuff, inbox, calendar. and then we just got creative and we did more and more complex, interesting things, which we can talk about. And what I found was the more leverage I got, the more ambition I got,

and it just compounded. And you started with one assistant, now I've got a half dozen, and every assistant gives me more leverage to take on more things. It's fascinating because some people say, hey, Bill Gates is so much richer than me, but he has the same phone that I have.

Or I remember, maybe it was you, maybe someone else who was like, the president should have way better information than me, and yet they're like reading political, like they're reading the same. This is like another example of it, which is a democratization where White House have amazing assistance, but thanks to Athena and technology,

at some point everyone will have a certain . Exactly, a couple decades ago, you had to be Mark and Driesen, Irvinodikosva to have a half dozen assistance, and that costs 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.

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 achieve a staff on top, but it's just kind of a ladder of leverage. How should we think about what are the things that humans can do versus what are the things that AI can do? I remember my friend started Clara, you know, a decade ago, which is trying to be AI assistance. Effective absence is well before a lot of the innovation. But what is the right way of thinking about sort of the human AI relationship? Yeah, I mean, it's a moving target, obviously.

A is going to get increasingly more capable. And our view is it's like self-driving cars where it's not, self-driving overnight. It's you drive the Tesla at first, and then there's assisted steering and braking, then over time, it becomes more autonomous, and the same thing is going to happen with assistants. My view here for founders is if you don't have an assistant, you are the assistant, and you don't want to be the assistant. And so no matter your budget, you should first start by learning to delegate. And if you only got 20 bucks a month, you start by delegating to chat GPT. and prompt engineering is really just delegating.

And if you become world-class at leveraging chat GPT to brainstormer goals, figure out how you can take the next step in the business, once you have the budget for a human assistant or chief of staff, then you're prepared to go that next level. So you start 20 bucks a month. If you have budget, then you hire someone direct with a service like Athena. If you have enough money, you hire someone in person. That's six figures.

And if you're a legendary budget, then you've got a suite of assistance and chief of staffs following you around. Yeah. So I've had an Nithia for many years now, and she's absolutely amazing. And I use her for scheduling and typical assistant activities,

but you have many assistants, our friends Sam Corkos, has a bunch of assistants as well. What else do people get leverage on or delegate that? Maybe it's not obvious. So first, you start by taking the pain off of your life. So I never wait on hold. I never put my credit card in the internet. I would never fill out DMV forms, never do passport renewal.

The world is full of all these annoyances. And so first you take off these things that drain you, that don't give you leverage. Then once you've done that, then the next thing is you raise your sites and you're like, what's a new business I could start? How can I scale my business faster? How can I spend more time with my family? What are the things I actually care to do a lot more of? Yeah.

And so I start with basic stuff, inbox calendar, stuff that everyone does. but then I just start experimenting. And so during the scale-up days of Thumbtack, when we're in a house, working all the time, I told Marnie and my assistant, I don't really have any friends outside of work. I was like, the only people I know are in this building, I need to make some friends.

And so I told her, let's plan a founder dinner at my house every other week, and we did lots of this together back in the day. And that's how I made all my best friends. And I just walked home from work, and Marnie had invited people, set up the chef and the bartender, and we walk in, friends and I met Catherine, my wife, through that. And then Marty's helping plan our wedding,

and now Marney helps us with our kids. And so, start small, and then you just kind of compound these things. Yeah. But even in that example, say more about how did she know who to reach out to? Yeah. So the kind of entry-level delegation is you delegate by task. You say, help me plan this dinner party. If you just say that, you're not going to get what you want. The more advanced way to delegate is called delegate by algorithm, where you actually export your own. internal preferences as you delegate. So I would say, hey, when I plan dinner parties, I like to have six to eight people. I like people to have raised similar amounts of capital or be at similar stages or similar number of employees and literally write an algorithm for how you find the right

people. And then you give feedback on whether it worked or not. And once the algorithm is fully exported from your head, then it's just rinse and repeat. And so engineers tend to be better at creating these kind of like SOPs or standard practices, but it's something that you're you can learn to do. Yeah. And so share more about for people of multiple systems, how do you differentiate, like how do you sort of delegate across the team?

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

And that specialization is helpful because the finance person is just thinking, about balance sheet, you know, sending wires, all that sort of stuff. And then I've achieved a staff who sits on top, who distributes work across all of them. What are other principles, like I love this Delegate by algorithm, not by task,

what are other principles or frameworks that are really important or not obvious to get the most out of an system? Yeah, the Cardinal sin of delegation is that it will be faster or better to do it myself. That's the number one blocker for most people. And the reason it's a blocker is because it's true. It will actually be faster or better

if you do it yourself that first time. 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. 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. So this is kind of like common principles. like common principles. In terms of the way to delegate, I think this is just tactical, the methods. The most common way people delegate is with your thumbs and your phone. That's the worst way, very slow. Better 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 in between lunch and the Uber. At thumbtack during hyper-scale times, I would walk between meetings, and between a meeting, I would be voice noting to an assistant. Here's the takeaways, pre-draft these five emails, follow up with this person, and all my work from that meeting was actually delegated by the time I started the next meeting versus everything kind of accumulating, and then you get to the end of the day, and you're like, I have a hundred things to do. And so learning to delegate by voice, if you look at all the super delegators at Athena, they

are all just delegating my voice all day long. Right. Yeah, it's fascinating. At some point, it's going to be, I don't even have to say it. I just think it. This is part of our vision, Athena, longer term, is you shouldn't have to actually vocalize it. And we've built an internal demo of this.

It's not live for customers, but the way it works is we build something that watches your screen as you work, and it screenshots the screen. And when it identifies things that you should be delegating to your system, it automatically adds it to your assistant's task list. Your assistant then says, oh, Eric would want my help with this, or maybe he'll do this one his own, and that creates the reinforcement learning effectively

to tune the model. To pull things off of your screen, you don't have to vocalize. And so the person who built this internally, he's been using it, the majority of his delegations are now machine generated. He's not talking.

He's just working, and the machine is magically pulling tasks and putting on his assistance plate. It'll take a while to bring that to market and fruition, But that's the future. Relatedly, there should also be a version where it's like you see in Slack that it's someone's birthday or someone has a baby or something and it suggests, hey, do you want to get this

person, this specific gift or something? Yeah. I think this is a place where we're thinking a lot about the human machine merger and how we get the best of both. And that's really the vision Athena is like the best human assistant, the best AI wrapped into one combined product that's seamless. And humans obviously have human touch and good UX. 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. One thing you've always been fascinated about is sort of international labor, some people call it labor arbitrage. What is the right way of thinking about what people in, say, the Philippines can do or can't do versus assistance in the U.S.? Because obviously there's a huge cost savings. What are stuff that you keep in that cost savings? are stuff that you don't keep. What's the right way of thinking? Yeah.

I mean, America's strength is entrepreneurship, capital, innovation, technology, and the more you can leverage someone to do back office tasks, the more you can spend on technology, product, et cetera. So I think the thing Athena focuses on is executive assistant, someone who can do all of this admin. But people are using global talent for all sorts of things, for legal, medical, all the both.

Yeah. So on the finance thing, I'm curious because I don't leverage mine there. What are the ways that people could get leveraged from this? Because are you still interfacing with the accountants? Or are they doing? Yeah, what is the right way of thinking about? Yeah, so the first thing I'd recommend if you're getting an assistant is to have them help you save money.

If you have a big budget, not a big deal, but the first project can be, hey, help pay for your salary by looking through all my subscriptions, finding things to save me money, find me refunds. So that's just kind of like a cost saving bucket. Then there's admin paying bills. And then there's coordination, which is what you're talking about, basically being a PM. So coordinating 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. 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 give email and calendar access at first

and bank account later. But as you earn that trust, then the more access you give effectively, the more leverage you get. Yeah. Yes, it's interesting. And in terms of seeing more about what it's been like to scale this company where you have,

and you know, you dealt with this thumbtack to a little bit in terms of just workforces in different areas and how you think about culture between them and yeah, kind of what are the, the challenges or what's really important to get right. Yeah. I mean, we look for cultures that have strong affinity to American culture.

You know, Philippines has long history with America. They like no American pop culture and sports better than I do. And then they have a very strong work ethic and it's a caretaking culture. So there's lots of nurses and one of the reasons we picked it for assistance is being an executive assistant is really taking care of someone. It's like their full-time job is to make your life better, is to take things off your plate to help you be successful. And I think one of the barriers for some people to get an assistant

is it feels indulgent. It's like, should I really have someone who's just taking care of me? but the way I flip that around is you not delegating and you're 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

and for the people in our team like they could have worked with the CEO they get to see behind this exciting startup that is a totally different life that they live and for them that is a cool, exciting, life-changing thing. One thing that I think people should be using

assistance more for is not only delegation but also accountability of like, hey, you want to be, you know, exercising this amount, or you want to be spending your time doing X, Y, Z, or you want to make sure you go to your appointments or something. Do we have some clients who actually exercise live with their assistants for this reason? Like, they both have a fitness goal, and so they pull videos at a set time,

and they work out together. And that's the place where human accountability is a little more powerful than machine accountability. ChatchipT actually has a feature now where it will automatically pin you on things. So if you can't afford an assistant, you just tell chat GPT, here's my top five goals, ask me how I'm doing every day, log my results, and give me feedback. You can get that for 20 bucks a month. I've done similar versions of this with human assistance. 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 peeing on WhatsApp every day, and I'll just reply yes, no, yes, no, whether I did it. And then at the end of each week, send me a scorecard and compare me to Eric or, Catherine and we can have a little competition with it. And, yeah, helping you hit your goals is exactly what they should be doing. Yeah. And then the other thing I think is an interesting opportunity to get more leverage because these people are also, you know, not just operational savvy, but also, you know, pretty, you know, intuitive.

You know, they go into caring fields. And so there's also like opportunities for coaching, too. Or like, you know, they're the people that have most context on you. and they can give feedback on how you're engaging, or like, you know, they can tell you, hey, you're tired today, you know. Yeah. It was my first observation when I was in the West Wing.

The assistants who sat next to the president were insane. They were so good. They went on to become elected to Congress and amazing people. But at the end of the day, the president, his advisors would have been meeting with senators and all these people.

And they would finish the meeting. They would lean back and they would have the assistant come over, and they'd just be like, what's going on? And it was more than just accomplishing things. This was their closest confidant who saw behind the scenes on everything. They knew the good and the bad. They know they'd gotten kicked in the nuts

a couple of times that day from different things. And they're there for them. And I think that human element is going to remain important for a long time, no matter how good AA gets. And it's something you should lean into. We have clients who tell us that, yeah like going through a divorce or a depression and like my assistant's like there for me in a way

that others aren't and like I can't tell my company or my team about some of these things but it's this is the person that's like on the inside with you yeah totally related one of the things you've had really interesting insights on over the years is uh is how to spend time think about time management not only in terms of ways to get more of it via delegating but also you know how to prioritize and I've learned this from you, but you think about goals on a sort of, you know, annual, quarterly, you know, like on different increments. Well, maybe we could start with LBD and how you think about goal setting in general, and then we can, you know, get a bit deeper. I mean, my wife, Catherine and I, who we met his friends, want to, you know, developed his friendship over one of these entrepreneurship dinners. We read this book called How You Measure Your Life by Clayton Christensen, and he basically,

told the story of how Harvard Business School professor, kids come back at reunions, and they're Fortune 500 CEOs, super rich, and their lives are in shambles, they're divorced, have all these problems, the kids don't talk to them, going to jail.

And he's like, the rigor they apply to their businesses, the quarterly reviews, the metrics were completely absent from their life. And his point was, how do you want to measure your life? And Catherine 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 directors. Let's freaking do that. And so we just started tradition a decade ago. Every quarter, we get together. We fill out a survey in our relationship, strengths and weaknesses, kind of squat analysis, geeky stuff.

And then we talk about what can we improve, what can we do better? And like anything, the more you invest, the better gets. Totally. And yeah, I think that's a key point because some people are turned off by sort of like quantification, like they want their relationship to be placed like, you know, relax or turn off or something. I think it's less that you have to like, you know, quantify every element of it. And more just that you want to, you don't want to let the lack of quantification mean that you're not prioritizing it.

And so this is just an exercise to make sure that you're actually just like keeping accountable to how you want to be. Exactly. It's be purposeful, the thing you want. If you're a geek like us, then you measure it and you track everything. Yeah. And if you just want to go have like a date and drink wine and talk about your relationship, that works too. I think it's just people prioritize fitness or their work, but they never think about how do I prioritize my relationship?

Like, what's the fitness or the workout or the yoga equivalent for my relationship? Having been in many goals-setting sessions with you, one of the things I think that you intuitively understand or have learned and are often instilling in others is this idea of prioritization. Like when people say goals, they said a lot of goals, and they don't sort of think about,

hey, what is the one that makes everything else much easier? And, you know, what is the one thing that if we did would be a great year, a great quarter, or whatever it is. Who sets too many goals? You know, me a little bit. But yeah. Yeah, I think my views is there's a power law in everything,

and power law in business, power law in venture, power law in your life. And there's typically one thing every month or a quarter that if you accomplish, it's worth more than everything else combined, and figuring out what that one thing is is what you should do. Figure that thing out and then go all in on that. And not to say that having other goals isn't worthwhile, but if you haven't identified the one thing

and gone all in to make that happen, then I think it's not optimized. I think it's also easier to kind of procrastinate on the most important thing in your life by having a long list. And you do a bunch of different things, but there's that one thing. It's find your partner. It's start the business.

It's fix my health. That really is more foundational than everything else. So to that end, I'm curious if you could share more frameworks or principles you live by in terms of time. Like, for example, I believe you put, you try to stack meetings in, you know, in a day or in as few days as possible or something. What are certain sort of frameworks that are important for you in terms of, you? time, energy, you know. I mean, high level, Brian Johnson wants to break the chains of biology or longevity.

I want to break the chains of time. And, you know, the question I asked myself is like, what's the most valuable asset in the world? It's not gold or Bitcoin or Navidia clusters. It's time. We can always raise another round or do another trade, but you can't raise another decade. And so if time is the primary asset and it's more foundational than everything else,

we should focus on owning that and controlling it. And so this means different things for different people. If you are in hardcore scale mode, that may mean half-hour meetings for 14 hours a day where you are just grinding out interviews and doing things that only you can do as a founder. Or it may mean clearing your schedule and having time to dream about the future of the product or big deals. And I think you just have to know what stage of the business you're in and then design your calendar purposefully around. that. And if you look back on the last month and the calendar does not reflect your highest goals, then you're not doing it right. Yeah, I remember Keith Rboye shared with me this idea of

like at the end of every week, do a calendar audit at the past week. Like, what are the meanings you had that you wish you wouldn't have? And then just look at the next week. I mean, this is a place, 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. If not, then next week we should adjust those things. Yeah. I'm curious for your interpretation of meetings. Some people are like, you know, I want to have as few meetings as possible. It means not the most efficient. I'd rather do everything async. Yeah. What is your kind of

sort of thinking between async and synchronous? I mean, Naval has a good line that's like a phone call is better than a meeting. A voice knows is better than a call. A text is better than a voice now. I think in general that's true and there's this it's almost like a generational thing where I feel like you're in this a little bit of like there's a reluctance to call people on the phone

and it's just we do everything text and email but calling people is super effective it's really high bandwidth you can figure shit out in five minutes and so I personally try to minimize meetings and then do more picking up the phone and talking to someone

for five minutes When I'm in more chairman mode, then I prioritize as few meetings as possible and voice notes. And what I request is voice notes out and text messages back because listening to voice notes is slow. It's assault as market trees. Exactly. Yeah. Yeah, it is interesting. One of my favorite self-help books is the seven effective habits, how it affects people.

and one of their, you know, principles, maxims is this idea of like efficiency with when it comes to achieving, you know, tasks or accomplishing tasks, but effectiveness when it comes to people. And so, you know, the efficient path might not be the effective path because you might, you sort of save some time on the front end, but you might, you know, accrue sort of a debt on the, on the back end. And yeah, it might be efficient to just send a text or something, but, you know, keeping the dynamic, yeah, phone calls are high. obviously under underrated and 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 a couple months for a few days in person how do you think about how when founders are asking for advice like 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 are the most important ways to get right. Whether it's your time at thumbtack.

Yeah, I mean, it's build your product, he's his customers, raise capital, build your team. And when founders ask me like how to leverage an assistant, what should I be doing? The way I turn around is like, what's your top two goals for the month? If it's recruiting, you have to be closing candidates, but you don't need to be sourcing all of the emails.

You could pull up a voice note and say, here's a template I want you to reach out to. 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. And so, you know, step one is you set your goals

and then you break them down into sub-tasks. And your assistant won't be able to run the fundraise, but can run components of it. And your job is just to decompose things into the smallest part that you can hand off. Maybe you should have some sort of like forward-deployed, you know, sort of thing of what's, it's not just the assistant,

but it's also someone that helps you really get the most leverage out of it and watches your activity. One of our learnings from this business, when we first started it, we're just going to hire the best assistance, match them with clients, and boom, amazing. But we matched the first five assistants

and every single client said the same thing. How do I delegate calendar? How do I delegate in box? And so it became clear we needed to invest more in actually teaching the clients how to delegate because that is as much of a constraint as the assistance. And we've got a few thousand,

assistance and clients. And if you look at the best performing assistance at Athena, they work for the best delegators. It's not a coincidence. The reason they're the best is because someone has figured out how to export their ideas, decompose projects, create SOPs in a way

that helps the assistant fly and the more mediocre delegators struggle with that and need more training. Yeah. One thing that you've been phenomenal at is whether Stumpack or Athena is higher 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? I mean, one thing that is obvious as you hire execs is the more senior they go, the better

they are interviewing almost by definition. And so when you get to C-Suite, they all are really good at interviewing. And so you actually have to discard the interview more, the more senior they go. And so I use references. 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 startup where you could like ping the LM about someone versus pinging their references. So I try to get to more ground truth. on the person versus the ux of interview is just going to be pretty good when you get to the senior

level what's most important in when you're when you're doing reference checks what are you really what's the way to get the most signal out of them and what i often tell people is hey i'm probably going to hire this person uh and now tell me all the things you don't like about them or things that they could be better at because if 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. And once they start to sound the same,

then you've got a signal. Yeah. One question I like to ask is, what skill sets would be really important to compliment this person with? It was another way of just saying, what are they bad? 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? Yeah. And I mean, the best way to source, talent. I just hired an executive recently. Just ask the people that you respect the most. They have the highest standards. Who's the best person? So like,

here's the three people who have the highest standards in this role. I ask them for the two or three best people and I go try to hire one of them. And that is the like speed, rapid way to hire an exec. You know, using an exec recruiter, you spend three months, you get all this cold leads, but going through a network of high bar people is

super efficient. There's some maxim that almost like half of executives you know, don't work out within like, you know, 12 to 24 months period. Checks out. Yeah. Why is that? 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. And I think like Weebly back in the day would actually have execs come work for two weeks to trial before they ever hired. That's difficult to pull off because people have other jobs. But I do think something like that makes a lot of sense. Your interview process is just kind of irrelevant compared to what the work they're doing in lots of cases. Yeah, and Keith has this maxim that that's like you're not going to get 100% hiring in the same way. You're not going to get 100% investing.

And if, you know, like you also want to avoid the trap of not taking enough risk or moving too slow. Yeah, and as long as you cut your losses quickly, it's okay. If you don't cut losses, then you compound a hole. That's where it's painful. The other thing I'd say is more useful for basically all interview process is project-based work. So it's just like hiring 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. And I'm like, come up with the plan.

How would you fix this? If we hire you, you're going to do it. And that sort of practical work is more useful. Yeah, that's really interesting. Going back to other sort of founder principles, what is your stance on transparency with the company? Like, what's information that's helpful, maybe going back to Thumbtack days,

what's helpful for the company to employees to know? What are principles that guide how much you share? Yeah, I mean, default transparency is obviously the best, but there's obviously some lines. There's, you know, at Thumbtack, there was a moment, you may remember this a decade ago where I woke up and I had a message from someone

on our team in the Philippines and said, Thumbtack does not exist on the internet. I was like, what? And I went to Google, you type in Thumbtack and nothing shows up and we basically received

the death penalty from Google. There was a misunderstanding they thought we'd done something wrong, but they like eliminate us from the internet. And so our traffic went to zero and our revenue went to zero. And I remember waking up and I go to the office,

and there's a class of 25 new thumbtackers who is their first day. I'm supposed to do the onboarding with him. There's a journalist walking around outside trying to get a quote. And that's one of those times where you can't share everything. And so you want to ultimately be transparent.

But if I just walked into a new class and say, hey, business might be dead. It's not going to work. And so you have to kind of get a handle of the situation, you know, the people who need to know it, know it. And then once there's a plan and a solution in place, then the whole company is told. Yeah, that makes sense.

At Thumbtack, you were a non-CEO co-founder, and you lasted a decade or almost a decade, and you're still on the board, of course. I feel like it's pretty rare when I think about co-founding teams, that it feels like the non-CEO, especially if not a CTO, usually that doesn't last, you know, over five years or something. I'm curious what's really important to get right in co-founder relationships or how you think about advising, you know, companies that you invest in?

Yeah, I mean, I heard Sir Michael at Sequoia say something that was like, there's only one founder. Yeah. And it was at, he said it at a founder event. And I was like, that's rude. There's lots of 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. So I think that's just the reality

and it's good to know that going into starting a business. In terms of who to pick, my advice is you pick someone you want to get married to and you're going to have all the same relationship issues you have with a partner. You know, no makeup sex, but it's still like, yeah, there's highs, lows,

and you want someone that ultimately you really deeply trust because there's going to be stress and challenges. as long as you trust the foundation, then you got a good thing to build on. I'd say, you know, one of the biggest, I don't know if I called a mistake at Thumbtack, because I love my founders,

but it's something I wouldn't recommend others do, is we had four co-founders, and one was technical. He left after like two years, and then the other three were non-technical. This is like the most idiotic way to start a technology business, but we had no idea what we were doing,

and, you know, it worked out. And how did you divine and conquer between those three non-technical? We just kind of jumped on things as like whoever was good at something would do it. Yeah, but it was no clear executive. Yeah, and I think that's, you know, that's not recommended because there's like,

it's obvious how that could create tension. We worked through it, but that's why it's non-standard. Yeah, yeah. Not best practice. Right. But I'm going back to the original story because I remember there's this, you got into GSB and you were going to go to grad school,

but you, you know, had your buddies from college, You were thinking of starting this business, which wasn't even like a personal pain point. You just thought it would be a good business. And you emailed the, you know, let the GSP 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, et cetera,

you know, it turned out pretty good. But how do you, a pretty good decision, how did you at the time think about get enough conviction to take the leap and do it? Yeah, it was scary. I got into this good school, seemed like that was a safe bet. I knew I wanted to start a business. And, you know, if I went to business school,

I knew that I'd have all this debt. I probably might need to get a nice paying job afterwards. And if I was 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. I just said something like 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. I never responded, and I have it as an email in my, the save that I'm just going to respond to whenever some tech goes public and be like, I made the right decision. And I have nothing against this guy. He's just doing his job, but it's good to have a little chips on your shoulder. Yeah, totally. Okay, so there's EAs, and then they're cheating.

Chief of Staffs, how should we think about sort of the difference there and what's really important to get right in Chief Staff? It's a role that everyone, in addition to EA, wishes they had, but seems hard to find the right person. Yeah, there's no formal definition. I think it's something that an EA is typically more administrative and taking things off your plate and Chief of Staff is more offensive and that's the type of person who can follow you into meetings. You could deploy to, hey, like actually take this meeting inform me or hey, this problem came up today, go figure out how to solve it. And so a chief staff typically has the capabilities to become a founder themselves. And the only reason they take

the job as chief of staff is so they can see what it's like to be a founder so they can go off to do it. So you kind of get people who do more tours of duty and you get super high capability, but you don't get the same longevity as an assistant. What have you looked for in chief staff? Or what's sort of the right, you know, there's sort of this tension between, you know, getting someone younger who's, you know, definitely initially going to do it for a couple years and is more ambitious versus someone who's been more seasoned, but maybe not as high slope or something. How do you think about? The way I break it down is assistant, you find someone you want to go a decade with. The intimacy and the compound,

and you know that relationship is super important. And so you go deep. And that means you probably don't find a founder because they're not going to be excited to do this. It's someone who's much more of a caretaker and is excited to be number two. And then a chief of staff, I do pure slope where you know the person is going to move on in a couple years, but they have, yeah, they could start a business, but instead you get them by your side to help solve problems. And there are people, you know, like Lonsdale, maybe like a lot or something, who have, you know, chief staff for like a year or two, and then they start a company, then they invest in them, and

they build kind of this reputation for doing. And then they have sort of these, like, you know, alumni, almost achieve the chief staff, just kind of, you know, Peter Thiel's or just kind of further. Yeah, Bezos has this. Someone follows him around. It goes to every meeting. And, yeah, it's cool. Yeah. Let's talk about some people who get an enormous amount done.

And I'm curious what are lessons that we can draw from them. Whether it's someone like Lonsdale, whether it's someone like Elon, whether it's someone like Sam Altman, who are folks that you've particularly learned something from, even just watching from afar of like, how do they build their world, how do they operate? I'll just say one for someone like Lonsdale, Teal has done this really well. They sort of compound these certain talent networks. So there's like Stanford Review or just Stanford in general.

They're often hiring people from there and then involved in sort of these talent pipelines. They've sort of created to, you know, they're deep in the hackathon scene. But they just kind of build this proprietary compounding sort of talent base that they're constantly, you know, sort of. I mean, the talent access is part of it. I think the other thing is there are some people who have just limitless ambition.

You're very much this way of like, well, what if I could do 10 times more things? And I think lots of people just think that's impossible. But it's not. It is possible. And with delegation and empowerment, you can just keep compounding bigger and bigger scale. The other thing that's interesting

that we've seen from working with these power delegators is people assume that people of great power are well, or resources can afford this team. And then that is why they have this ambition. But we've actually seen the opposite is the case, is as people get more leverage with assistant, their ambition increases. And it's difficult to have big ambition.

If you're just weighed down by DMV forms and passports, but once that's off your plate, then you raise your sights and you can be more ambitious. And then you go from assistant to achieve a staff and you just keep leveling up to, you know, until you're Lonsdale or the president. I think another thing I've admired about some of these people is they, you know, they remark hold remarkably few grudges.

Like, you know, apparently, you know, Peter Thiel, like, kicked Elon out of PayPal or something. Or, you know, like, a lot of these people have had beefs, you know, decades ago. And yet he ended up funding his next company. And so people have very short memories if someone, you know, mistreats them or something. Or they make a mistake or something. They're quick to reconcile and just do business. again over, yeah.

Yeah, I mean, look what President Vance said about President Trump before they were partners. Yeah, yeah. I think there's... Trump's actually quite forgiving. Or, you know, a lot of people say a lot of bad things about him and he'll continue to work with them as long as they change their mind. Yeah, I think there's just a desire to win at all costs and, yeah, grudges are not helpful. Yeah, even Trump and Elon, right?

Yeah. Getting into it and, you know, reconciling. Yeah. It's, you know, TVD where it stands by the time this comes out. And then there are some people who seem to... have pretty, like, you know, Bill Gates has, like, you know, pretty big team, pretty big operation. But then it seemed like

Bezos and Elon maybe have, like, pretty lean teamed in. So, yeah, I'm curious how you think about, sort of... I mean, Elon's the one that makes no sense. It's, he claims to not have an assistant and to be, like, scheduling stuff. There's a story of Bill Gates being, like, trying to schedule a meeting with Elon. He's, like, connect me with your assistant.

And Elon's like, no, I am my assistant. I hardly believe it, but Elon's just insane. So maybe he is that way. I think most normal humans, if you want to get leverage, you have to delegate. I mean, one of the cool personal teams I saw is this guy who's a billionaire. He runs this hedge fund, and he has a team of 40. He has eight personal executive assistants. All of the executive assistants graduate from Princeton, insanely high bar.

And I was asking this woman who managed the EA team, like, How do you decide what to prioritize your team on? And she's like, if my team can spend one day saving my principal one minute, it's well worth our time. And I'm like, that is so next level and definitely like, that's something I would love to aspire to, but it's just, you know, the billionaire budget. Yeah. It's pretty funny.

Also, just in terms of prioritization, like, you know, we're hiring, you know, assistance here. And someone's saying, oh, you know, do you want them to be in all meetings? with you. And I was like, well, if there are meetings with me, then they're not working. Like, I want them to be like, you know, finding ways to give me leverage and take things off my plate. I mean, this is one of our visions at Athena is that you can have digital assistants that listen to you and work with you and are connected to your Zoom and your inbox and your calendar and can be mining all of that digital exhaust for things your assistant should work on.

And so, I mean, your assistant can't possibly sit in every meeting if they're going to do anything. But if the digital, the machine assistants are surveying it and pulling things out, that's It's a pretty cool combination. Yeah. I think it's interesting to look at how people build out their universe. Like for example, Mark and Ben funnel everything through A-S-Z and are all in an A-C-N-Z and of course have, you know, other intellectual or philanthropic interests, but mostly it's like consolidated, whereas someone like Peter Thiel has this, he sort of fragments it a bit more,

you know, like founders fund, but then several other, you know, myth-rolet, several other funds, other company, all sorts of like initiatives that are, you know, somewhat collaborative but independent. Yeah. And he, he says on top, but also it seems like he lets them, you know, he's not like CEO of them. And he's got this sort of talent, you know, network that he's worked with for a long time that kind of like, you know, goes in almost boomerangs across the universe. Lonsdale feels like he's more hands, he's got the ABC universe,

but then his other initiative, he's like quick to institutionalize something, whether it's like a think tank or like, you know, it's no coincidence that, you know, Peter Thiel would do the sort of Teal Fellowship and Lawsdale, create a university or something. Teal is almost like early to stuff. He creates a format for something, a template. You know, he does the hard work of sort of, you know, field building, or like, you know, doing something

that's in a controversial space where it's longevity or charter cities or, you know, higher education. And then, you know, people like Lonsdale institutionalize it to some degree. And then, yeah, Elon, you know, it's been described, also has this like SWAT team, you know, of people that help him

from company to company and he's just able to recruit, you know, world class people to lead these efforts. Yeah. I think it comes, it's like, what's the right org structure? There's actually no right orc structure. It's what's the right org structure for you as a founder?

And, you know, Mark Andreessen and Bin Horowitz are company builders. And so they're building their leverage like a company. The A16 Z is a company. Not that Peter Thiel is not an entrepreneur, but he's more of a philosopher today. And so his system is more like a philosopher. So all these kind of wild and crazy ideas. And so I think, you know, Jensen Huang has like 46 direct reports or something,

which is absolutely insane, but it works for him. And so I think you just have to know what your style is and then you build it for you. Totally. And someone like, you know, Sam Allman is like a dealmaker and a fundraiser and a talent identifier, you know, and so he's able to, like, I remember he was at YC and he was talking to one of my friends about sort of this universal basic income company.

My friend didn't end up doing it, but I was like, oh, that's interesting. Why is he even doing that? He's like focused on YC. And he has a knack for good ideas. He's a knack. And this person was like 22. He has a knack for, you know, high-slope talent, and he has a superpower around raising money.

Yeah, I mean, one of the things that I think new founders, or at least me as a new founder, was like, okay, what are my weaknesses and how do I get better at them? But then a second-time founder is like, forgive all my weaknesses. I'm just not even going to try. I'm just going to be really good at my strengths, and I'm going to hire other people to do all the things I'm not good at,

and that is way more effective. Yeah, totally. 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 CEO has to be the founder, and they have to drive it to. Where do you stand on, on kind of that debate? I think the biggest companies aren't incubated because the biggest companies have a founder who is monomaniacal from the beginning and compounds it for 50 years.

And that's not incubation. Incubation is kind of, let me try a bunch of thing. It's not this monomaniacal power law commitment. So if you're just trying to build a trillion dollar, I think that's not the way to do it. Yeah. But look, if you like, you know, we have a mutual friend who likes to remain anonymous, who incubates lots of companies, and he launches four companies a year, and he loves doing it, and he's going to make a ton of money doing it, and that's just his style. He's not going to probably

have trillion-dollar businesses, but he's going to have 50, you know, $100 million businesses, which is still incredible. Right. Yeah, I think one bill case is more of its, like, breeding, like, you know, Sam Altman in some sense incubated open AI in that it wasn't the, you know, the main thing he was working on, but then once he identified that it could be, you know, this massive opportunity, then went all in with it. Yeah, I mean, it's more like a venture portfolio. And, you know, there's probably a bunch of stuff Peter Thiel has done that we don't even remember, like, sea-studying and things like that, because they just disappear into the ether and then

things that work compound. And so, I mean, here's the resources to launch 10 new things and then just double down on the one thing that's big every year. Yeah. That's a cool, cool approach. Right. A decade ago, Mark Andreessen wrote this blog post on productivity. And they were asking him, how do you think about meetings, scheduling, whatever?

And he said, you know what? I try not to schedule things in advance because I don't know how I'll feel next week. And I kind of want to do things like in flow. And so when, you know, people are trying to get my time, what I typically say is like, call me right now or feel free to check in next week and we'll see how I feel. Yeah. And it kind of is like better aligned with sort of the flow state. I mean, that's the ultimate flex. Yeah.

It's like if you can pull that off, that is definitely the ultimate way to live. Yeah. Because you just work on whatever you want. The world opens up to you, you call. Obviously, it's hard for most new mortals to pull off. But yeah, if you can get to that level, that is the dream. Right. So then I was for certain meetings that people with cold reaching out or whatever,

I was kind of try. It's like, I always anticipate that in a few more days, I'll be like busier than I am or something, or I'll have, whereas like right now, yeah, I got time, give me a call. But so I tried that a little bit. And then Mark did a follow-up interview where someone asked him about that, sure I'm. And he's like, oh, you know, that didn't work.

Like I tried that didn't work. Now I'm just scheduled. Just back to back all day long. And I was like, oh, God damn it. You've been doing that. And it's, but he's, you know, he's also massed. to multitasking. I mean, I think people just,

the thing I think you can learn from Mark and other people is just challenge the defaults occasionally. And if you're in back-to-back means all the time, try this other system and see if it works. I think most people just go with the flow. I think other things, most people aren't vicious enough at saying no and just being super hardcore. Is that conference you're going to matter?

Is that random, get to know you, chat, meaning anything? Yeah. I think you just say no. to most things. You know, I've, back in the Uber versus Lyft, really scaling war days, I remember emailing Logan a question, probably to come to one of our dinners, and he just responded war mode. And I love that. And I'm like, well, most people should actually be in war mode, like 90% of the time.

And that same, yeah, hardcoreness is just like the right way to operate. Yeah. What have you learned in your extensive founder career? about managing your own psychology, dealing with stress, dealing with the cognitive dissonance of having to present externally, like things are amazing even when you're concerned about Google, taking out your business. What advice might you have for others in terms of cultivating this?

Yeah, man, I think it's like a cold plunge or something. It's just shock therapy, and eventually it's just like you're bathing in an existential. fear all the time and you're like, whatever. Let's bring it on. Totally. I don't think there's much other than knowing that it's going to happen. There's going to be tons of ups and downs. I think one of the clear lessons from Thumbtack,

which is now scaled and done so well, was that there was lots of near misses where we almost died, times where we thought it wasn't going to work, and it's like you just got to stay in the game. Yeah. And if you can stay in the game, you can eventually win. Yeah.

And I think Thumbtack was very good at staying in the game, so that we can eventually win. Yeah. It's funny, there's, like, degrees of panic in the beginning, you know, you're getting your feet wet. It's like, oh, my God, someone said something mean about me on the internet. And then it's like, oh, my God, someone wants to, like, leave my company.

And then it's like, oh, my God, we're going to, you know, we might die. We only have six months of payroll. Then it's like, oh, my shit, we're going to get sued. Yeah. It's like, you know. Well, it's like the first time you get sued or you're worried about getting sued. And then eventually you have a board meeting,

and there's just a list of lawsuits, and it's just, you review them quarterly. It's just like, that's actually what success is. It's like you're going to have that stuff constantly, and it becomes, yeah, it's part of business. Yeah, yeah. And you just keep building up more capacity to handle these things, and they, you know, just come.

Yeah, and it's where, like, I think co-founders are the best. This is like, it's the people you can be totally open with and be like, well, that's situations, F stuff. Yeah, and someone you can trust and be on the ups and down. with. Let's go to Athena and let's go where we started, which is sort of the intersection between humans and AI. How have you thought about building Athena given sort of developments in AI? What does that mean for your future? Yeah, so Athena started fully bootstrapped, human only scaled to a thousand people, no outside

capital. And then we had this AI moment a few years ago. And it was clear we could make a big AI play, and this could become a generational business, or we could get railroaded by AI. And so only one option there is go big. And our vision here is this is you take the best of a human and best of machine, wrap it into one unified product, and what the machine does will increase over time, just like a self-driving car. And so the humans, the UX, it's on top. It will become more, the human assistant will focus more on project management and high-level work.

and really be that like caretaker, the empathy, that partner. And the machine will increasingly do the more mechanical administrative stuff. And, you know, just as when you get into a Tesla, you know, Elon made them with wheels, or steering wheels, so you could drive them because they don't drive themselves when you started. But every time you get in the car,

you're actually teaching the machine how to drive. And these models don't generalize while. You have to bring edge cases under distribution. And so every time you drive, the model gets more powerful. And the same is true in executive assistant. Our humans are driving. They're doing the tasks,

but we're building machine models that are being improved by the way they act. And so the more your assistant does tasks for you, the more models will improve, and they'll allow the human to upgrade what they work on to more high-leverage stuff. Yeah. That's exciting.

So what else can you share about plugs for the company or things to watch out for or for people who, you know, want to get assistance. Yeah, look, I just say if you don't have an assistant, you are the assistant. Step one, if you're starting a business, you should hire assistant. And if you've got 20 bucks a month, use chat GPT. If you've got, you know, $10 an hour, go on to Upwork and hire someone yourself. If you hire someone yourself, I would say my main recommendation is you need to interview a lot of people.

You know, Athena, we have 50,000 assistants apply per month. and we put them through a huge battery of tests, and we hire like 1 and 300. So if you're going to hire on yourself, make sure you interview not 10, but probably like 50 people. If you have the resources for $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, 100, 150K a year, you should do that as well. And then ultimately, you know, when you get later stage, you have achieve a staff, in-person assistant, and a fleet of Athena assistance in the cloud. Yeah, that's a great overview. Well, let's wrap on that. Awesome.

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