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 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?

Cardinal sin of delegation is that it will be faster or better to do it myself. And the reason it's a blocker is cuz 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 Andreessen or Peter Thiel 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.

What have you learned in your extensive founder career?

Jonathan, welcome to the podcast.

Thanks for having me.

So Jonathan, you're running a massive company. What 4,000 employees? 4,000 employees. You also do investing. You're also 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 chief of staff, a bunch of EAs. Why don't you talk about what is the secret that you've figured out that other people can learn from?

Yeah. So, my origin story here is out of school, I worked at the White House and 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 a Thumbtac, I said, "Okay, I'm not president, but what if I had a EA and support team that was as good as the presence? Like, what could I accomplish?" And so at Thumbtac, 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, 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 I some people say, "Hey, you know, Bill Gates is so much richer than me, but he has the same phone that I have." 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 political like they're reading the same media." And this is like another example of it, which is the democratization where White House have amazing assistance, but thanks to Athena, you know, and and you know, technology, at some point, everyone will have a certain block.

Exactly. that you know a couple decades ago you had to be Mark Andreessen or Peter Thiel 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 and then with AI yeah it's going to become ubiquitous. People are there's going to be billions of people learning to delegate to a machine assistant and as your budget increases you might add a human or a chief of staff on top but it's just kind of a ladder of leverage. How should we think about what are the things that humans can do versus what are the things that AI can do? You know, remember my friend started CL um you know a decade ago which is trying to be AI assistance effectively. Obviously this is well before a lot of the innovation but what is the right way of thinking about sort of the human AI you know relationship.

Yeah I mean it's a moving target obviously is going to get increasingly more capable and our view is it's like self-driving cars where it's not self-driving overnight. It's you drive the Tesla at first and then there's assisted steering and braking and then over time it becomes more autonomous. And the same thing is going to happen with assistants. My 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. Uh 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 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 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 uh legendary budget, then you've got a suite of assistants and chief of staff following you around. Yeah.

So, I've had an for many years now and and she's absolutely amazing and um you know I use her for scheduling and u you know typical assistant activities but you have many assistants you know our friend Sam Corkos has a bunch of assistants as well close the gap between what do the people who do it well like you know what else do people get leverage on or delegate that maybe is not obvious.

So first you start by taking the pain off of your life. So you I never wait on hold. I never put my credit card in the internet. I would never fill out DMV forms, never do passport renewal. The world is full of all these annoyances.

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

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 scaleup days of Thumbtac, when we're in a house working all the time, I told Marne, 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 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 Marne 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 through that and then Marty's helping plan our wedding and now Mary helps us with our kids and so you know it starts small and then you just kind of compound these things.

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

Yeah. So the kind of entrylevel 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. Um, 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. Um and then you get 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 you know engineers tend to be better at creating these kind of like SOPs or standard practices. But it's something yeah you can learn to do.

Yeah. And so share more about what how you for people have multiple systems or how do you differentiate like how do you you know sort of delegate across the team?

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

Um and uh that specialization is helpful because the finance person is just thinking about balance sheet, uh you know, sending wires, all of that sort of stuff. And then I have a chief of staff who sits on top who distributes work across all of them.

What are other principles like, you know, I love this delegate by 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?

Yeah, the 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 cuz 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 6 12 months. But it's the compounding that creates incredible leverage. I've been working with Marne for a decade, like a little sister now, and she knows everything about me.

So that's just kind of 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 between lunch, you know, in the Uber. Um, you know, at Thumbtac during hyperscale times, I would walk between meetings and between a meeting, I would be voice noting to an assistant, here's the takeaways, pre-draft these five emails, 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 and then you get to the end of the day and you're like, I have 100 things to do.

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

Yeah, it's fascinating. Well, at some point it's going to be, you know, not I don't even have to say it, I just think it.

Yeah, this is uh this is part of our vision uh Athena longer term is you shouldn't have to actually vocalize it. No. And we've built an internal demo of this. It's it 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, Eric would want my help with this or maybe he'll do this on his own." And that creates the reinforcement learning effectively to tune the model to pull things off of your screen. You don't have to vocalize.

And so the person who built this internally, he's been using it. The majority of his delegations are now machine generated. Yeah, he's not talking. He's just working and the machine is magically pulling tasks and putting on his assistance plate. Uh it'll take a while to bring that to market and fruition, but that's the that's the future.

There should also be relatedly there should also be a version where it's like you know you see in Slack that's you know it's someone's birthday or someone has a baby or something and it suggests hey do you want to yep you know get this person this 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 uh product that's seamless. And humans off obviously have human touch and good UX. Uh but what machines can do is remember everything and be super proactive. who can look through every email, every calendar and remind you to do things that you would not have thought to do otherwise.

One thing you've always been fascinated about is sort of um international labor some call, you know, labor arbitrage. What is the right way of thinking about what people in say the Philippines um can do or can't do verse, you know, assistance in the US? Like how do people because obviously there's a huge cost savings. Um 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?

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, etc. So, you know, I think the the thing Athena focuses on is executive assistant, someone who can do all of this admin. Um but people uh are using global talent for all sorts of things for legal, medical, um all the above.

Yeah. So let's get a little bit on the finance thing. I'm curious because I I don't leverage mine there. What are the ways that people could get leverage from this because are you are you still interfacing with with the accountants or are they do Yeah. What is the right way of thinking about?

Yeah. So I the first thing I'd recommend if uh you're getting an assistant uh is to have them help you save money. Uh if you have a big budget, not a big deal, but the first project can be, hey, help pay for your salary by looking through all my subscriptions, finding things to say, 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. Um and then there's coordination, which is what you're talking about, basically being a PM. So coordinating, you know, the tax attorney asks for something from the accountant, and there's a bunch of docs, and it's just moving paperwork between Yeah. uh systems um at enough scale and complexity that becomes effectively a full-time job. And obviously you need someone you truly trust uh to go deep with and we kind of recommend that you build this trust over time and you know you give email and calendar access at first and bank account later. Uh but as you earn that trust then the more access you give effectively the more leverage you get.

Yeah. the um yes it's really interesting and and in terms of um say more about what it's been like to scale this company where you have and you know you dealt with this thumb thumb too a little bit in terms of just work forces in different areas and how you think about culture between them and um yeah kind of what are the the challenges or what's really important to get right

yeah um yeah I mean we we look for cultures that have a strong affinity uh to American culture Uh, you know, Philippines has a long history with America. They like know American pop culture and sports better than I do. Um, and then they have a very strong work ethic and u, it's a caretaking um, culture. So, there's lots of nurses and one of the reasons we picked it for assistance is being an executive assistant is really taking care of someone.

It's like their full-time job is to make your life better, is to take things off your plate, to help you be successful. And I think one of the uh barriers for some people to get an assistant is it feels indulgent. 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. Yeah.

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

Yeah. One thing that I think people should be using assistance more for is uh is not only delegation but also accountability of like hey you want to be you know exercising this amount or you want to be spending your time doing XYZ or you want to make sure you you know you go to your appointments or or something. 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 and that's the place where human accountability is a little more powerful than machine accountability.

Chatpt actually has a feature now where it will automatically ping you on things. So if you can't afford assistant, you just tell CatchPT, 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 uh a month. Um I've done similar versions of this with Human Assistant. I think we may have done this in the past where I'm like, "Hey, I want to work out, meditate, eat clean, 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 Katherine and we can have a little competition with it.

And yeah, helping you helping you hit your goals is exactly what they should be doing. Yeah. And then the other thing I think is uh an interesting opportunity to get more leverage because these people are also you know um not just operation savvy but also you know pretty you know uh intuitive you know they go into caring fields and so there's also like opportunities for coaching too or like there you know they're the people that have most context on you and they can give feedback on how you're engaging or like you know they can tell you hey you're tired today you know. Yeah, the

that was my first observation uh when I was in the West Wing. The assistants who sat next to the president were insane. They were so good. They went on to become like elected to Congress and amazing people.

Um but at the end of the day, the president, his adviserss would have been meeting with senators and all these people and they would finish the meeting, they would lean back and they would have the assistant come over and they'd just be like, "What's going on?" And it was it was more than just accomplishing things. 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 times that day from different things.

And they're there for them. And I think that human element is going to remain important for a long time, no matter how uh good AI gets. And it's something you should lean into. We have uh 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. Relatedly, one of the things you've had really interesting insights on over the years is um is how to spend time. think about time management not not only in terms of ways to get more of it v via delegating but also you know h how to prioritize and you know I've I've learned this from from you but you think about goals on a sort of you know annual quarterly you know like on different increments why don't you maybe we could start with LBD and how you think about goal setting in general and then we can you know bit deeper

yeah I mean my wife Katherine and I who uh we met as friends one of you know developed this friendship over one of these entrepreneurship dinners. We read this book um called How You Measure Your Life by Clayton Christensen and he basically told the story of how Harvard Business School professor kids come back at reunions and 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 and 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 Katherine 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 on our relationship, uh strengths and weaknesses, kind of squat analysis, geeky stuff, and then we talk about like what can we improve, uh what could we do better, and like anything if you the more you invest, the better it gets.

Totally. And yeah, I think that's a key point because some people are turned off by sort of like uh quantification like they want their relationship 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 prior you you don't want to let the lack of quantification mean that you're not prioritizing it. Um, and so this is just an exercise to make sure that you're actually just like keeping accountable to how you want to be.

Exactly. It's uh be purposeful, get the thing you want. If you're a geek like us, then you measure it and you track everything. Uh, and if you just want to go have like a date and drink wine and talk about your relationship, that works too. I think it's just the people prioritize fitness or their work, but they never think about how do I prioritize my relationship? Like what's the what's the fitness or the workout or the yoga equivalent for my relationship?

Having been in many goal setting sessions with you, one of the things I think that you intuitively understand or have learned um and are often instilling in others is this idea of um prioritization. Like when people set goals, they set a lot of goals and they don't sort of think about, hey, what is the one that makes everything else much easier? Um and uh you know, what is the one the one thing that if we did would be a great year, a great quarter, whatever it is.

Who sets too many goals?

You know, me a little bit. Uh but uh but yeah.

I think my view is there's a power law in everything and power law in business, power law in venture, power law in your life. And there's typically one thing every month or quarter that if you accomplish is worth more than everything else combined. And figuring out what that one thing is uh is what you should do. Figure that thing out and then go all in on that. And not to say that having other goals isn't worthwhile, but if you haven't identified the one thing and gone all in to make that happen, then I think it's not optimized. I think it's also easier to kind of procrastinate on the most important thing in your life by having a a long list. Yeah.

And you do a bunch of different things, but there's that one thing. It's find your partner, it's start the business, it's fix my health. That really is more foundational than everything else.

So to that end, um I'm curious if you could share more, you know, frameworks or principles you live by in terms of time. Like for example, I I believe you put you try to stack meetings in, you know, in a day or in as few days as possible or something. What are what are certain sort of frameworks that are important for you in terms of time, energy, you know,

I mean high level is Brian Johnson wants to break the chains of biology or longevity. I want to break the chains of time and you know the question I asked myself is like what's the most valuable asset in the world? It's not gold or bitcoin or nvidia clusters. It's time. Uh we can always raise another round or do another trade but you can't raise another decade. And so if time is the primary asset uh and it's more foundational than everything else, we should focus on owning that and controlling it.

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

Yeah. I remember uh Keith Rabois shared with me this idea of like at the end of every week do a calendar audit of the past week like what are the meetings you had that you wish you wouldn't have and then just look at the next week.

I mean there's a place uh you know Athena assistants 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 those actually your goals. Yeah,

If not then next week we should adjust those things.

Yeah. I'm curious for your interpretation of meetings. Some people are like uh you know I I want to have as few meetings as possible. Me is not the most efficient. I'd rather do everything async. What what is your kind of

I mean Naval has a good line that's like uh a phone call is better than a meeting. A voice notes is better than a call. A text is better than a voice note. Uh I think in general that's true. And uh there's this it's almost like a generational thing where I feel like you're in this a little bit of like there's a reluctance to call people on the phone and it's just we do everything text and email but calling people is super effective. It's really high bandwidth. You can figure out in 5 minutes. And so uh I personally try to minimize meetings and then do more picking up the phone and talking to someone for five minutes. Um, when I'm in more chairman mode, then I prioritize as few meetings as possible and voice notes and um I uh I what I request is voice notes out and text message back because read listening to voice notes is slow.

It's assault as marketing. Yeah. Um yeah it is interest you u one of my favorite self-help books is the seven effective habits of how effective people and one of their you know principles maxims is this idea of like efficiency with when it comes to achieving uh you know tasks or accomplishing tasks but effectiveness when it comes to people and and so um you know the efficient path might not be the effective path because you might you sort of save some time on the front end but you might you know acrew sort of a debt on the on the back end. Yeah. And um yeah, it might be efficient to just send a text or something, but you know, keeping the dynamic. Yeah, phone calls are 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 couple months for a few days in person.

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 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 to get right whether it's your time at

thumbtack look is build your product customers raise capital build your team 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 if it's recruiting uh 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. Uh, you know, if your goal is to raise capital, your assistant could help project manage the the process of all of that. And so, you know, step one is you set your goals and then you break them down into subtasks. and your assistant won't be able to run the fund raise but can run components of it and your job is just to decompose things into the smallest part that you can hand off.

Maybe you should have some sort of like forward deployed uh you know sort of thing of what's it's not just the assistant but it's also someone that helps you like really get the most leverage out of it and watches you know your your activity. One of our learnings from this business when we first started it, we were like, we're just going to hire the best assistants, match them with clients, and boom, amazing. But we matched the first five assistants, and every single client said the same thing. How do I delegate calendar? How do I delegate inbox?

And so it became clear we need to invest more in actually teaching the clients how to delegate uh because that is as much of a constraint as the assistants. And we've got a few thousand assistants and clients. And if you look at the best performing assistants at Athena, they work for the best delegators. It's not a coincidence. The reason they're the best is because someone has figured out how to export their ideas, decompose projects, create SOPs in a way that helps the assistant fly and the more mediocre delegators uh struggle with that and need more training.

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

I mean one thing that is obvious as you hire execs is the more senior they go the better they are at interviewing almost by definition and so when you get to seuite 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 re 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 asked to see it and I say, "Hey, I'll share you share mine. You show me yours. I actually think this would be a cool kind of reference pro startup 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 an interview is just gonna be pretty good when you get to the senior level.

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

I mean, what I often tell people is, hey, I'm probably going to hire this person. Uh, and now tell me all the things you don't like about them or things that they could be better at. Cuz if you know, people are so biased to just tell you all the good things. You have to get them to uh to see it as a safe place to share strengths and weaknesses. And yeah, just do enough references until they start to sound the same. And once they start to sound the same, then you've got a signal.

Yeah. One question I like to ask is um what skill sets would be really important to complement this person with? Um which is 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 6 months or a year, you know, why would that be?

Yeah. 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? 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. Um 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 a you know 12 to 24 month period checks out.

Yeah. Why is that? I think it's this it's difficult to uh judge uh the interview process is not representative of the work they're doing. And that's ultimately what's broken about interviewing is interviewing should be someone doing the work they're going to do. Um I think it was like Weebly back in the day would actually have execs come work for two weeks to trial before they ever hired. That's difficult to pull off because people have other jobs. But I do think something like that makes a lot of sense. your interview process is just kind of irrelevant compared to what the work they're doing in lots of cases.

And Keith has this maxim that that's like um you 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 you know of not the uh trap of not taking enough risk or moving too slow.

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

So just like hiring uh seuite for one pro uh one part of the team I just tell them what the pain points in the org are and what I want to fix and I'm like come up with a plan like how would you fix this like if you we hire you you're then going to do it and that sort of practical work is more useful.

Yeah that's really interesting. What um going back to other sort of founder principles what is your stance on um transparency with the company like what's information that's helpful maybe going back to thumbtack days what's helpful for the the company to employees to know like what what are principles that that guide you know how much you share

yeah I mean default transparency is obviously the best but there's obviously some lines like there's uh you know at thumbtac there was a moment you may remember this decade ago where I woke up and I had a message from someone on our team in the Philippines and it said Thumbtac does not exist on the internet. I was like what? And I went to Google. You type in Thumbtac and nothing shows up. And we basically received the death penalty from Google.

Uh there was a misunderstanding. They thought we had done something wrong, but they like eliminated us from the internet. And so our traffic went to zero and our revenue went to zero. And I remember waking up and like I go to the office and there's a class of 25 new thumbtackers who it's their first day. I'm supposed to do the onboarding with them. There's a journalist like walking around outside trying to get a quote. And you know that's one of those times where you can't share everything. And so uh you want to ultimately be transparent but if I just walked into a new class and say hey the business might be dead uh that's not going to work. And so you have to kind of get a handle of the situation. uh you know the people who need to know it know it and then once there's a plan and a solution in place then the whole company uh is told

yeah that that makes sense. Um at Thumbtac you were a nonCEO co-founder and you lasted you know a decade or almost decade and you're still on the board of course. Um I feel like it's pretty rare when I think about co-founding teams that it feels like the nonCEO especially if not a CTO usually doesn't last you know over 5 years or something. Um I'm curious what's really important to get right in in co-founder relationships or how you think about advising you know companies you invest in.

Yeah. I mean the 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. Yeah. Um so

I think that's just the reality and uh you know it's good to know that going into starting a business. Uh 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. uh you know, no makeup sex, but it's still like uh yeah, there's highs, lows, and you want someone that ultimately you you really deeply trust because there's going to be stress and

um challenges, but as long as you trust the foundation, then you got a good a good thing to build on. I would say, you know, one of the biggest I if I called a mistake at Thumbtac, uh because I love my founders, but it's something I wouldn't recommend others do is we had four co-founders and one was technical. He left after like two years and then the other three were non-technical.

This is like the most idiotic way to start a technology business, but we had no idea what we're doing and uh you know, it worked out. And how did you divide and conquer between those three non-technical

uh we just kind of jumped on things is like whoever was good at something but it was no like clear executive.

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

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

Yeah, it was scary. I uh got into, you know, this good school. Seemed like that was a safe bet. I knew I wanted to start a business and uh, you know, if I went to business school, I knew that I'd have all this debt. 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, I was like, this is biggest mistake of your life. He said something like uh you can startups will come and go, but you can only come to Stanford once or something. This is a once in a lifetime opportunity. I never responded and I have it as a email in my this save that I'm just going to respond to whenever Thumbtac goes public and be like, I made the right decision. 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.

Yeah, totally. Okay, so there's EAS and then there chiefs of staffs. 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 um but seems hard to find the right person.

Yeah, there's no formal definition. And I think it's something that uh an EA is typically more administrative and taking things off your plate and uh chief of staff is more offensive 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 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 kind of get people who do more tours of duty and you get super high capability uh but you don't get the same longevity as an assistant.

What have you looked for in chief of staff or what's sort of the right, you know, there's sort of this tension between, you know, getting someone younger who's, you know, definitely initially going to do it for for a couple years um 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. Uh the intimacy and the compounding of that relationship is super important. And so you go deep and that means you probably don't find a founder because they're not going to be excited to do this. It's someone who's much more of a caretaker and is excited to be number two. And then a chief of staff I do pure slope where you know the person is going to move on in a couple years but they have yeah they could start a business but instead you get them by your side to help solve problems.

And there there are people you know like Lonsdale maybe like a lot or something who have you know chief of staff for like a year or two and then they start a company then they invest in them and they build kind of this reputation for for doing and then they have sort of these like you know um alumni almost chief of staff just kind of you know Peter Teals just kind of further

yeah Bezos has this someone follows him around that goes to every meeting and yeah it's cool

yeah let's talk about some 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 Alman, who who are folks that you've particularly learned something from even just watching from afar of like how do they build their world? How do they operate? I'll just say one for for

someone like Londale Til has done this really well. They sort of compound these certain talent networks. So, you know, whether it's like Stanford Review or just Stanford in general, um they're often hiring people from there and then involved in sort of these talent pipelines. they sort of, you know, created, you know, they're deep in the hackathon scene, but they just kind of build this proprietary compounding sort of talent base that they're constantly, you know, sort of um

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

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 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. Yeah.

And it's difficult to have big ambition. If you're just weighed down by DMV forms and passports, but once that's off your plate, then you raise your sights and you can be more ambitious and you know, then you go from assistant to a chief of staff and you just keep leveling up to, you know, until you're lonsdale or the president.

I I think another thing I've admired about some of these people is they um you know they remark hold remarkably few grudges like um you know apparently you know Peter Thiel like kicked Elon out of PayPal or something or you know like a lot of these people have had beefs you know decades ago and yet he ended up funding his next company and so people have very short memories if if someone you know mistreats them or they make a mist mistake or something they're quick to reconcile and just do business again over Yeah.

Yeah. I mean, look what uh President Vance said about President Trump before they were partners. It's I think there's Trump's actually quite forgiving or you know a lot of people say a lot of bad things about him and he'll continue to work with them as long as they change their mind.

Yeah. I think there's just a desire to win uh at all costs and uh yeah, grudges are not helpful.

Yeah. Even Trump and Elon, right? You getting into it and you know, reconciling, you know, TVD where it stands by by the time this comes out. And and then there are some people who seem to have pretty like uh you know Bill Gates has like you know pretty big team, pretty big operation.

Um but then it seemed like Bezos and Elon maybe have like pretty lean and 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. and he's like, "Connect me with your assistant." And Elon's like, "No, I am my assistant." Uh, it's I I hardly believe it, but Elon's just insane. So maybe he is that that way. I think most normal humans, if you want to get leverage, you have to delegate.

I mean, the one of the cool personal teams I saw is this guy who's a billionaire. He's runs this hedge fund and he has a team of 40. Uh he has eight personal uh executive assistants. The 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 uh principal one minute, it's well worth our time." And I'm like, that is so next level and definitely like that's something I would love to aspire to, but it's just, you know, the the the billionaire budget.

Yeah, it's pretty funny. Um also just in terms of prioritiz like um you know we're hiring you know assistants here and someone was saying oh you know do you want them to be in all meetings with you and I was like well if they're in meetings with me then they're not working like I want them to be like you know finding ways to give me leverage and take things off my plate.

I mean this is one of our visions at Athena is that you can have digital assistants that listen to you and work with you and are connected to your Zoom and your inbox and your calendar and can be mining all of that digital exhaust for things your assistant should work on. And so I mean your assistant can't possibly sit in every meeting if they're going to do anything, but if the digital uh the machine assistants are surveying it and pulling things out, that's a pretty cool combination.

Yeah. Yeah. I think it's interesting to look at how people build out their univer like for example, you know, Mark and Ben funnel everything through as Z and are all in on Z and of course have, you know, other intellectual or philanthropic interests, but mostly it's like consolidate.

Whereas someone like Peter Teal has this um he sort of fragments it a bit more you know like um you know founders fund but then other several other you know myith several other funds other company all sorts of like um initiatives that are you know somewhat collaborative but independent. Yeah. Um and he he sits on top but also it seems like he lets them you know he's not like CEO of of of them. Um, and he's got this sort of talent, you know, network that he's worked with for a long time that kind of like, uh, you know, goes in almost boomerangs across the the universe.

um lonsdale feels like he's more hands he's got the HBC universe but then his his um 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 Teal would do the sort of teal fellowship and la create a university or something teal is almost like early to stuff he creates a format for something um a template you know he does the hard work of sort of um you know field building intellect or like you know uh doing something that's in a controversial space or it's longevity or charter cities or um you know higher education and then um you know people like Lonsdale institutionalize it to to some degree.

Um and then yeah Elon you know it's been described also has this like SWAT team um you know of of people that help him from from company to company and he's just able to recruit you know world-class people to to lead these efforts.

Yeah. I think it comes it's like what's the right org structure? There's actually no right or structure. It's what's the right or structure for you as a founder and you know Mark 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 kind of wild and crazy ideas. Uh, and so I think, you know, Jensen Hang 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 Alman 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 my one of my friends about sort of this universal basic income company. My friend didn't end up doing it, but I was like, "Huh, that's interesting. Why is why is he even doing that?" He's like focused on waste and he's like

he 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.

Yeah. I mean one of the things that I think new founders or at least me as a new founder was like okay what are my weaknesses and how do I get better at them? But then a second time founder is like forget all of 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. The um there used to be this sort of skepticism of like hey you can't really and there still is actually you can't really incubate company like this the CEO has to be the co- the founder they have to drive it to where do you stand on on kind of that that debate.

I think the biggest companies aren't incubated because the biggest companies have a founder who is monomaniacal from the beginning and compounds it for 50 years.

Yeah totally and that's not incubation. incubation is kind of let me uh try a bunch of thing. It's not this monomaniacal power law commitment. So if you're just trying to build a trillion dollar business, I think that's not the way to do it.

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. Well, he's not going to probably have trillion dollar businesses, but he's going to have 50, you know, hundred million dollar businesses, which is still incredible, right?

Yeah. I think one bookcase is more of it's like uh breeding like, you know, Sam Alman in some sense incubated OpenAI and that it wasn't the main thing he was working on, but then once he identified that it could be, you know, this massive opportunity then then went all in all in with it.

Yeah. Yeah, I mean it's more like a venture portfolio and you know there's probably a bunch of stuff Peter Teal has done that we don't even remember uh because like sea studying and things like that because they just disappear into the ether and then things that work compound and so yeah I mean if you have the resources to launch 10 new things and then just double down on the one thing that's big every year that's a cool cool approach

right a decade ago Mark Andreessen wrote this blog post on productivity and they were asking him how you think about you meetings, scheduling, whatever. And he said, "You know what? I try not to schedule things in advance because I don't know how I'll feel, you know, next week and I want kind of want to do things like in flow." And so when, you know, people are trying to get my time, what I typically say is like, "Call me right now or feel free to check in next week and we'll see how I feel."

And it kind of is like better aligned with sort of the flow state. Um, and I mean that's the ultimate flex. It's like if if you can pull that off, that is definitely the ultimate way to live is you just work on whatever you want. The world opens up to you. You call

obviously it's hard for most uh new mortals to pull off. But yeah, if you can get to that level, that is the dream,

right? So then I I was for certain, you know, meetings that people cold reaching out or whatever. supposed to kind of try. It's It's like um I always anticipate that in a few more days I'll be like busier than I am or something or I'll have whereas like right now, yeah, I got time. Give me a call. Um but so I I tried that a little bit and then I Mark did a follow-up interview uh where someone asked him about that. Sure. Um

um um and he was like, "Oh, you know, that didn't work." Like I I tried but that didn't work. Now I'm just scheduled everything just back toback all day long.

I was like, "Oh, god damn it. You've been doing that." Um, and it's um, but he's, you know, he's also mastered uh, multitasking. And

I mean, I think people just, uh, the thing I think you can learn from Mark and other people is just, uh, challenge the defaults occasionally. And if you're in back-to-back meetings all the time, try this other system and see see if it works. Uh, I think most people just go with the flow. I think other thing is most people aren't vicious enough at saying no. Yeah.

And just being super hardcore is like, is that conference you're going to matter? Is that random? get to know you chat mean anything? Yeah, I think you just say no to most things. Um, you know, I've back in the Uber vers uh really scaling war days, I remember emailing Logan a question um 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 hardcornness is just like the right way to operate.

What have you learned in your extensive founder career about uh managing your own psychology, dealing with stress, dealing with the cognitive dissonance of, you know, having to present externally like things are amazing even when, you know, you're concerned about Google, you know, taking out your business. Um what um what advice might you have for others in terms of cultivating this?

Yeah, man. I think it's like a cold plunge or something. It's just you just shock therapy and eventually you it's just like you're bathed in existential fear all the time and you're like whatever, let's bring it on. Totally. Uh

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

And if you can stay in the game, you can eventually win. Yeah. And I think Thumbtac was very good at staying in the game so that we can eventually win.

Um 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, um, we're, you know, we might die. We only six months of payroll." Then it's like, "Oh my we're going to get sued."

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 revict them quarterly. It's just like that's actually what success is is like you're gonna have that stuff constantly and it becomes Yeah. Just part of business.

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

Yeah. That's where like I think co-founders are the best is is like it's the people you can be totally open with and be like, well, that situation's effed up. What? And someone you can trust and totally be on the ups and downs with.

Let's go to Athena and let's go where we started, which is sort of the intersection between uh humans and AI. How have you thought about building Athena given sort of developments in AI and what does that mean for for 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 uh 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 uh our vision here is this uh is you take the best of a human and best of a machine wrap it into one unified product and what the machine does will increase over time just like a self-driving car and so

the humans the UX it's on top uh it will become more the human assistant will focus more on project management and highle uh work uh and really be that like caretaker that empathy that partner and then the machine will increasingly do the more row mechanical administrative stuff and you know just as when you get into a Tesla, uh, you know, Elon made them with wheels, so with steering wheels, so you could drive them because they don't drive themselves, uh, when he started, but every time you get in the car, you're actually teaching the machine how to drive. Yeah.

And these models don't, uh, generalize well. You have to bring edge cases under distribution. And so every time you drive, the uh, the model gets more powerful. And the same is true in um, executive assistant. Our humans are driving. They're doing the tasks, but we're building machine models that are being improved by the way they act. And so the more your assistant does tasks for you, the more our models will improve and that'll allow the human to upgrade what they they work on to more high leverage stuff.

Yeah. Um that's exciting. So what what else uh can you share about plugs for the company or things to watch out for or for people who you know want to get assistance, you know? Yeah, look it uh I

just say if you don't have an assistant, you are the assistant. Step one, uh if you're starting a business, you should hire assistant. And if you've got 20 bucks a month, use Chat GPT. Yeah. If

you've got, you know, 10 bucks an hour, go on to Upwork and hire someone yourself. Uh if you hire someone yourself, I would say my main recommendation is you need to interview a lot of people. Uh you know, Athena, we have 50,000 assistants apply per month and we put them through a huge battery of tests and we hire like one in 300. So, if you're going to hire on yourself, make sure you interview not 10, but probably like 50 people.

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, 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, inerson assistant, and, you know, a fleet of Athena assistants in the cloud.

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