Designing An Ideal Life, Founding Thumbtack, 10x Delegation (Jonathan Swanson of Athena and Thumbtack)
Smart Friends Episode 99: Jonathan Swanson
I've wanted to do this interview for years, because this guy has life figured out.
Jonathan Swanson joins us to talk about building Athena from a side project into a nine-figure company, why every ambitious person should have an executive assistant, and some shocking personal delegation stories.
In this conversation, we cover the wild early days of Thumbtack, why delegation is a J-curve, and how Jonathan went from hiring one assistant to running a company that vets 50,000 applicants a month. We also dive into Athena’s AI pivot, how voice-based delegation is the most efficient, and the counterintuitive path to learning leverage.
Links to Platforms:
We discuss:
How Jonathan developed calm under extreme startup pressure
Athena’s evolution from side hustle to billion-dollar vision
Why great delegation is a skill, not magic
Surprising personal and family delegation use cases
Combining humans and AI for exponential leverage
This episode is for founders, operators, and anyone curious about buying back their time and expanding what they believe is possible with the right systems and support.
Quotes from Jonathan:
“My mind is an inner citadel. I’ve got a good mind, a wife that loves me, and everything else is gravy.”
“I started Athena with the sole goal of generating income for my wife and I to live off of.”
“The vision of Athena is the best human assistants powered by the best AI.”
“Humans are good UX. We’ve evolved to like humans.”
“You don’t build the first Tesla without a steering wheel.”
“We're building something that watches assistants work, not to replace them, but to augment them.”
“Delegation is a J-curve. It's slower at first, but compounds.”
“The cardinal sin of delegation is thinking, ‘It’s faster to do it myself.’”
“You can think of an assistant as a cognitive prosthesis.”
“Belief is the first limiter. Most people don’t believe time freedom is possible.”
“Ask yourself: If I had a hundred more hours a week, what would I do?”
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Learn more about Jonathan Swanson:
Additional episodes if you enjoyed:
Andrew Wilkinson: De-risking Leverage, Investing vs. Operating, and the Best Part About Business
What Traits Make a Thiel Fellow? (w/ Danielle Strachman, Co-Founder of Thiel Fellowship and 1517)
Episode Transcript:
Eric Jorgenson: Dude, I'm so excited you're finally on a podcast tour. I feel like you're generally an eccentric recluse.
Jonathan Swanson: Yeah, I prefer to be eccentric recluse, but I'm excited to talk about Athena, and we've got lots of stuff going on, so I feel like it's about time.
Eric Jorgenson: Awesome. My opening get-to-know-you question that I'm deeply curious about for you personally is like, who are your heroes? Who do you admire or did you admire growing up?
Jonathan Swanson: Oh, I love it. Marcus Aurelius, one of my first heroes. I listened to this podcast about him recently, and you've probably read his meditations. He's talking about how your mind is the inner citadel and your happiness should come from within. But reading about the history of him, he was writing these meditations while he's on the front lines of the Roman Empire at war running the largest empire in the world. And startups and life always has its challenges and crises. But thinking about him managing the largest empire at war, people dying all around him, and then he goes back to his tent with a candle and he's like, my mind is an inner citadel, like what, one of the strongest minds in human history. And yeah, I aspire to be like him.
Eric Jorgenson: That's awesome. Did you like come to him when you were enduring stress and like recognize that he was one of the best at it, or have you always just like appreciated that and that sort of formed...?
Jonathan Swanson: Yeah, I just always appreciated it. I feel like I'm more stoic by nature. Some people are more excitable than I am. I'm much steadier through ups and downs. So I think the philosophy just kind of resonated with me. And the more I learned about him, the more I'm like, man, he was a maniac that he could have such mental strength during such hard times.
Eric Jorgenson: That explains- I feel like one of your hallmarks is like operating coolly in chaos and at high scale. So, it makes sense that that's like...
Jonathan Swanson: Totally. I mean, one of my favorite stories from Thumbtack is, people will be like, what's your favorite time from scaling the business? And I'll be like, well, it was actually the most chaotic time. I woke up one morning and a team member in the Philippines said, we have zero traffic to our site. Not like one visitor, zero. And at the time, we were getting millions of visitors. And I'm like, well, something terrible has happened. And so we look into Google Analytics and traffic has gone to zero. And then when you searched Thumbtack in Google, like if you search Thumbtack, the word, Thumbtack Home Services, nothing showed up. So, we quickly realized Google had given us the death penalty effectively of de-indexing us. So you couldn't find us even if you wanted to. And I remember walking, we had a kind of crisis, and we're like planning that Sunday night. And then I go to the office Monday morning, and there's like 30 new employees, who it’s their first day. And I have to do like a new employee onboarding, while I'm like having these calls to investors to figure out what's going on. There's like a journalistic outside our office trying to ask questions about what's happened. It was obviously intense and chaotic, but when I look back at it, it's actually one of my favorite weeks because you're backed in the corner, and you do whatever you've got to freaking do, and the team rallies, and probably wouldn't have as good of memories if we died, but we survived, and you're like, yeah, you're capable of so much in those moments of intensity, even if they're more chaotic than you want at the moment.
Eric Jorgenson: And your mind is an inner citadel. And now you know that for sure. You've taken a test and passed.
Jonathan Swanson: Yeah. I mean, you've got your friends, you've got your family, you've got your kiddos. And I think in those moments of crisis, you're like, I'm going to fix it, whatever it takes. But I've got a wife that loves me. I've got kids. And I've got a good mind. And everything's going to be okay.
Eric Jorgenson: Yeah, that's awesome, awesome perspective. There's a whole amazing like oral history, I'm sure, of Thumbtack that I hope you do on many podcasts many times. And you and I, at least in association, go way back because like Zarly and Thumbtack were doing similar things at similar times and you absolutely whooped our ass. And my life has gotten much better when I decided to stop competing with you and start investing in you.
Jonathan Swanson: I don't think we whooped your ass. I think all of our asses got whooped.
Eric Jorgenson: It's a brutal market.
Jonathan Swanson: We're last man standing. It's just a hard business and it's fortunately scaled to great size and doing well now. But yeah, we all got an ass whooping along the way.
Eric Jorgenson: Yeah. The allure of home services has enticed many people into the swamp.
Jonathan Swanson: Exactly. Yeah. I mean, people will reach out and be like, oh, there's this new competitor. Are you worried? And I'm like, welcome to the jungle. It's a huge market. It's a trillion dollar TAM. That's why it's so exciting. And marketplaces are great businesses. But unlike Amazon, which can sell and ship products everywhere, humans are different. And so, you've got to get reviews and know who's the best, and they may be good today but not as good tomorrow. And the number of marketplaces is immense. We've got a thousand categories of services and hundreds of cities. So, it's actually like starting hundreds of thousands of marketplaces. Because if you have enough house cleaners in San Francisco, it doesn't mean you have enough plumbers in Denver, and you have to solve all of those liquidities over time. So, it took us longer than we expected when we started to solve those problems. But we ground it out, and now, yeah, the team's kicking ass and doing the best they've ever done, which is pretty cool to see. And one of my lessons from the Thumbtack journey is like, you just got to keep going. And even when things are hard, as long as you got another swing, eventually it'll work if it's the right idea. And we took a bunch of swings and eventually it started working.
Eric Jorgenson: Yeah, which is a very cool- It's interesting knowing you as long as I have to see the threads between like how the fruit of Thumbtack planted the seeds of Athena. I'm curious about the... When you started Athena, did you have any sense that you were starting another really big business, or were you just kind of like messing around?
Jonathan Swanson: I mean, there's founding stories, and then, you know this, the founding story kind of gets rewritten over time. The real-life founding story is I moved to chairman at Thumbtack, and Thumbtack will go public one day, but I was like, I don't really have much money. I've got a big lottery ticket that's going to be worth something, but I need to make some money until there's liquidity. And so, I started Athena with the sole goal of just generating income for my wife and I to live off of. We were traveling the world at the time, having some extra freedom. We didn't have kids yet. And it seemed like a cool business to start. I've always been obsessed with delegation, as you know. You and I geek out about it. And it's improved my life in immeasurable ways, both personally and professionally. And I was like, well, maybe I'll just help friends achieve the sort of things I've achieved with my assistant. And so, I put up a website we made in a day, tweeted out about it, and a thousand people signed up. And I was like, well, shit, I got to hire 1,000 assistants. And so, we started working on it and started off mostly as a cash flow business, and then it got bigger and bigger. And then, I found a CEO to come in who had built 25,000 person teams in the Philippines. And he helped scale us from two to a hundred million run rate and really took it to a scale that I was never envisioning at the beginning. But it just became obvious as we got further along that the opportunity is bigger and bigger. And man, like this could do billions of revenue. And yeah, so our ambitions grew as the company grew.
Eric Jorgenson: Yeah, it's been through a few, like the vision's probably been through a few iterations. Is that fair to say? You reach a local maxima or turn a corner, and you're like, oh, wait, this is either even bigger or different or has a broader application. What is it today, the vision of Athena?
Jonathan Swanson: A vision of Athena is the best human assistants powered by the best AI. So taking the best of human assistant combined with the increasingly powerful AI machine assistants and wrap it into one seamless product. So, you work with your human assistant one-to-one, just as always. That's the UX. Humans are good UX. We've evolved to like humans. But behind that human, we build machine assistants that will increasingly automate more and more so that your human assistant can graduate to do more complex, powerful things. And it's really taking the best of both. And my analogy is like with Tesla self-driving, Elon did not build the first Tesla without a steering wheel. You need a steering wheel to drive it, and the human's driving it, and that's Athena today. We have a human driving the tasks. But when you get into a Tesla, you're actually, and you're driving, you're actually feeding data into the neural network that trains the machine. And that's exactly what our humans are doing. So our human assistants are doing the tasks themselves. We're building machine intelligence that watches them as they work so that it can automate their work over time, not to replace the assistant, but to augment them and enhance them and allow them to do more than would ever be conceived possible before. And yeah, to your question of like original vision, that was not in the original vision. The original vision was the best human assistants. And then I think the next evolution was the best human assistants plus we teach you how to delegate because that was clearly a barrier for lots of people. It's like, oh, I want to get more leverage, but how do I do X, Y, Z? And so we started thinking about how to teach our clients to delegate. And when the AI moment came, we're like, wow, either we're going to be impacted by this negatively or we're going to ride the wave by merging with the machine. And so let's merge with the machine. That sounds way more fun.
Eric Jorgenson: Yeah. So, in the AI era, you've been studying this for a few years, so much of the moat then comes from the actual data that you're collecting and you have, I don't know, thousands, tens of thousands of assistants who are, by your analogy, driving Teslas. And what, so now you've got an AI watching what they do on their screen?
Jonathan Swanson: Yeah, we're building something that sits on the OS that watches them as they work and uses the basic agentic data to help train the machine to know what they're doing, help give them feedback, help be proactive. The machines are good at remembering everything, at being super proactive, having more time than a human. And a human is better at the relationship, at the strategy, at connecting the dots, the project management. And so it's going to be a combination of the both. And we can do lots of cool stuff that a human struggles to do but wants to do. So we could look through all of your calendar for the week ahead and identify things that the assistant could be proactively helping you with. We could look at all your emails you've sent related to Uber Eats, and we could know your food preferences. And so when your assistant orders you food, they can order the burrito you love without having to ask you. And so, there's lots of work to be done to build this in a privacy secure way that really works, but that's what we're building towards.
Eric Jorgenson: That's so cool. And this is like, for context, quite a big pivot over the last 18 months. You guys raised a huge round, restructured the company, built out a whole new tech team in order to do this... What was the, I don't know, encounter or information, how did you have that inflection point of like, I've got a- you had a big business at this time, like this thing was thriving, it was growing. And it doesn't go away, but like it takes a lot to make a huge direction change of a nine figure business.
Jonathan Swanson: I mean, it came because I had a friend who's working on the red team at Open AI. And this is before the history changing launch of Chat GPT. And this was the summer before. And he started texting me things that he was seeing the model was able to do, and they were jaw dropping as we all soon discovered many months later. And so, I was like radicalized by this. I hired a PhD in machine learning that summer to start tutoring me on LLMs and the progress and what was going to happen. And then, the Chat GPT launch happened, and it was as game changing as expected. And yeah, it's like then my immediate reaction was, okay, do we play defense and this thing comes and eats our business or disrupts us, or let's play offense and let's like go at it. And offense is way more fun. So, let's go. And so we had previously bootstrapped the business with my capital, no outside capital, and we're running kind of a freedom oriented business. And this was a moment where like, all right, if we want to ride this wave, we're going to have to raise some money and go bigger.
Eric Jorgenson: So, I mean, also like unique in a few ways, one, to only do one round of venture, which is I think all you've done so far. And then in this world of staffing agencies, which is a big market, a shockingly big market, but there's not that many people there with the Silicon Valley chops and background and insight that you had into the pace of technology and what's changing. So, to combine those things and tackle a huge market with huge data and the Silicon Valley operating background is like, is a really cool recipe. I'm just super excited about it.
Jonathan Swanson: Yeah. That's why people ask like, why isn't anyone else doing this? And if Elon Musk decides he wants to do this business, like he could figure it out for sure. But the reason it's not happening is it has this kind of Venn diagram of skills that's very unusual. And so, your YC founder is not going to hire 3,000 assistants like we've done. We vet 50,000 a month. It's like a huge funnel of talent. We have entities around the world. We got buildings where we train and interview assistants. So that's just like an operational thing that a typical YC founder isn't going to take on. And then the AI labs are pure software businesses, and they don't want to take that on. And then to your point, that BPOs or old school agencies, they don't have the ambition or the technology orientation to do it. So not to say anyone else can't do it. I'm sure people will try. But it feels like we just got to move fast, we got to make as much progress, and it's ours to take if we execute well.
Eric Jorgenson: Yeah, that's so awesome. So, what's brought you out of your normal enigma mode of staying out of the spotlight and got you on a small podcast tour?
Jonathan Swanson: Well, multiple things. But one of them is we've finally increased our supply capacity in a super meaningful way. And so, in the past, as you know, we've been very supply constrained. And so, you'd be like, hey, can I get a friend an assistant? I'll be like, yeah, we'll help them, but it's going to take us three months. And that's obviously painful because you want to help people right away. And so we spent this last year really dramatically expanding our supply capacity. We are primarily based in the Philippines at first. We've launched Kenya and scaling Kenya to a huge degree, launching Guatemala now as well. So we have new regions. We've also invested in these training centers that I mentioned, where people actually come in person for interviews. There's weeks of in-person training. That allows us to really capture much higher tier talent. Because if you're some of the best talent in a country and an agency reaches out to you as an assistant, but they don't have an entity, they don't provide local insurance, there's nothing real about them, you're not going to get the best talent, but if you've got a sexy building that you're going to come into, it's a real office, real entity, benefits and all those sorts of things, you can capture much better talent. So, we made big investments on that so that we can really get the best talent and scale it up. And so, for the first time, we're like, wow, we're open for business and we can grow the demand side a lot faster than we have in the past.
Eric Jorgenson: That's awesome. I refer people to Athena all the time, and a lot of times, there is a wait list, and a lot of times the best perk is like, yeah, I think I can get you to skip the wait list. I'm sure the growth rate when you're no longer supply constrained is going to hit even a new pace. How do you pick these countries? I remember texting either you or Chris or both from visiting South Africa. And it was, I think, before you were anywhere outside the Philippines. And I was like, oh my God, you guys have to expand to South Africa immediately. And you were like, we're thinking about it, we're working on it, we're traveling, we're looking at it. But that's such an interesting problem of you got this whole big world, Guatemala and Kenya, very specific.
Jonathan Swanson: Yeah. I mean, you want... We're looking for developing countries where you've got great talent and a more affordable rate than the United States, but where people are highly educated, so great education systems, need to speak English. So English is the primary language learned in school. And we typically look for places that have a large and swelling youth population, where there's lots of talented people looking for jobs. And part of our mission is to bring opportunity and jobs to good, talented people around the world. And so you want to move to a market where there's just tons of people looking for opportunity. And then there's lots of particularities about how safe is the country in the legal codes? And are there other credible businesses there? Have other people started companies in the space? Because if there's been nothing started there, it's hard to hire leadership. So, this has kind of been a challenge for the Canadian startup scene is like they now have Shopify, but pre-Shopify, it was like, where do you hire your CTO and your exec? Because all of that's happened in Silicon Valley. So, there's a few countries where there are other companies that have gone in, hired and trained that kind of first layer of leaders. And so we look for stuff like that. And then just the culture – is it a high trust, a respectful, hardworking, caring culture? I think an assistant is a caretaker in some ways. It's someone who gets things done. But they're caring about you. They're thinking about you. They're trying to make your life better. And so a culture where people have that sort of disposition is also helpful.
Eric Jorgenson: Yeah. Which is tough to measure, but you know it when you see it, I'm sure. And I mean, when you're doing that kind of volume too, I mean, 50,000 a month, you said?
Jonathan Swanson: Yeah, it's nuts.
Eric Jorgenson: It takes a lot of population to sustain that for a long period of time.
Jonathan Swanson: Totally. We joke we want to get 1% of a country one day. Fill up some football stadiums.
Eric Jorgenson: You get some smaller countries and knock that right out. What's Luxembourg doing? Okay. So, this is... I mean, it's just, it is wild the like scale you guys operate this kind of thing at. So, who is the, I don't know, core like customer on the demand side? Has that like changed significantly? I feel like I was one of those first thousand who reached out just because like I knew you and I was like, God, I need an EA. So I've been in it early, early, but I imagine there's thousands or tens of thousands by now.
Jonathan Swanson: Yeah, the core demo was my friends. I was just like emailing my friends, texting people. I joke that now that enough of my friends have an Athena EA, I can like surreptitiously plan like pranks and events. I can just like have their assistant book them a trip and put it on their calendar and everyone's just going to show up. So it started off as friends and then that naturally led to startup founders because most of you are my friends. And so, startup founders, there's 100,000 venture backed startups in the country. So, we're maybe a percent of that. So still a 10x to go in startups. But this year we moved and expanded into the next segment, which is SMB. There's not a hundred thousand SMBs in the country, but 30 million. Now, I don't know what fraction could have an assistant, maybe 10%, so many millions of dental clinics and supply stores and just the wild...
Eric Jorgenson: Home service businesses.
Jonathan Swanson: Yeah. Service businesses. I mean, even large construction companies. I actually just talked to a large construction company that's got a hundred employees that's looking for an assistant. So SMBs is now the next big segment. And then in the long term, enterprise is the kind of mega segment, this fortune 500. So we have some enterprise pilots with a couple of great companies going now. We're just starting work there and we want to expand a lot into that next year. I've talked to places like AIG and JP Morgan where they have a thousand or even five thousand assistants internally. And we can offer an offering that brings assistants to a whole layer of the team that doesn't have it today. And so maybe the VPs or C-suite have it, but directors always wish they can have assistants and now they're going to be able to because we have a different price point. And with our AI productivity, they can bring it to the people. So that's going to be a big focus for next year.
Eric Jorgenson: I remember somebody saying at some point along the line, anybody who earns more than $150,000 a year should have an EA, just as a rough approximation. And I was kind of like, oh, with Athena, that does become roughly approximate. If you're doing a math of however many tasks you do are worth, those sub $40 an hour tasks that are critical but not particularly fun, and if you don't have an EA, you are...
Jonathan Swanson: Yeah, I mean, I think the most obvious place to start is if you have a business or a place that can generate revenue, an assistant can be kind of your first hire to help you spend more time focused on revenue generation or your craft or the reason you started the business. Most people start the business to like build the product or do the thing they love. And there's lots of important work that's like scheduling and admin and email and accounting that you might not want to do. And so an assistant can help with that. For some people who are more cash constrained, I say, hey, the first thing your assistant could help you do is help you save money. And so, if you're not tracking your finances well, if you look through all your subscriptions, go find alternative vendors for your business, that's the way to do it. But then yeah, there's other people who are dual income, make 250K and have a busy life. And for them, it's more a luxury good of, yeah, I can spend more time with my kids and my family, and that would be awesome. And that's worth paying $3,000 a month to spend more time with my kids.
Eric Jorgenson: Yeah. Absolutely. Buying back your own time from the stuff that is less fun.
Jonathan Swanson: Yeah. I mean, I was talking to someone who's like, what if I could hire myself, would I hire myself? And for most founders, you would, because you believe in yourself and you think you're capable enough. And like, well, I just realized if I hire an assistant, I am hiring myself because my assistant is doing things that I'm doing now. And then I get more of me for the most important work that I want.
Eric Jorgenson: I like that. I'd hire me for some jobs, but not all of them. So... something that I think really drew me to Athena is just like, I came into this orbit when it was like very much a cult of personality around like you, and if you're comfortable with it as like a line of questioning, I think, and I've told so many people at Athena this, that like the most compelling stories or examples like come out of you and your CEO, Robert, and some of your other executives who are like unbelievably good delegators, not just in like, whatever, the mechanics of it, the tactics of it, but in terms of just like the agency and the courage and the experimentation and like all the different things that you guys try. And so, I'm excited that you're like, I don't know, out here talking about it. And I'm hoping we can spend some time on like you and your family and your stories of like what you do with like you have multiple EAs personally.
Jonathan Swanson: Half dozen.
Eric Jorgenson: Half dozen. Okay, six personal EAs for you or you and your family?
Jonathan Swanson: Yeah, for my family.
Eric Jorgenson: How does this all split up? Tell me what the... Tell me the org chart of Jonathan, Inc.
Jonathan Swanson: Yeah, I'll premise this with I grew up in the Midwest. My parents grew up on farms. I'm like Midwest boy. We did not have assistants in our house. We didn't have house cleaners, anything like that. So, I think if 18-year-old Jonathan heard that I had a half-dozen assistants, he'd be like, dude, what happened to you? But I mean, if I can just divert with a quick story, then we'll talk about what we work on. For me, this started in part, I went down this track in part because I worked at the White House after school. It was my first job. And I sat in the West Wing. I worked for the president's economic advisor. And I sat next to the president's executive assistant. And as you might imagine, the president's executive assistant is freaking insanely good. And so it just set my bar very high for what this EA partnership could look like. And then when I went to Thumbtack, I hired my first, and I was like, you know what, what if I had an assistant support team that was as good as the president? I'm not going to be the president, but maybe I'll accomplish a lot more things and maybe my life will be amazing. And so I just had this kind of idea that I could do that. And I started by hiring my first assistant in the Philippines, used to Upwork. I encourage people, if you don't have the capital for Athena, like just go do it on your own. I can give advice on how to do it. And I hired someone on Upwork. And just start with basic things like inbox, calendar, travel. And then I just started experimenting. I'm like, hey, every week, we're going to try something totally new. This week, I want you to help me try to make friends. I don't know many people outside of my work. Let's do a dinner party at my house every week, and you just invite someone new. And so, we invite random founders, people like you at the time, we'd have like the founders of Uber and Airbnb. These were just tiny startups at the time. And I made all my best friends from that. And I ended up meeting my wife Catherine through that, and it became more than just a dinner party. But that's how, the way I think about it is just like, what are my top personal and professional goals for the month ahead? And then how could my assistant help me possibly accomplish those goals? And not everything's going to work, you need to be experimental, you need to be okay with failure, you need to be able to break up tasks into subtasks and that sort of thing. But if you experiment enough, you'll just eventually layer on more and more things that work.
Eric Jorgenson: So how many- just pick an example, like does this work because you are a really good delegator and you're coming up with a goal that's meaningful to you and breaking it down into projects and subtasks? Or do you just speak a whim and your EAs are really good at breaking it down and figuring out not just what to do, but then how to do it?
Jonathan Swanson: Oh, it's a partnership. You've got to be good at delegating. And if you look at the best assistants at Athena, they just so happen to work for the best clients. It's not a coincidence. The clients who know how to delegate, who are experimental, who partner, who give their EA lots of feedback, those assistants become superpowered because they're given the partnership and the investment to get there. And so, yeah, I will tell clients, hey, if you just want to show up and like have everything magically work, not how the world works, but if you're willing to put the time in, invest and experiment, then it will get better and better. And it's a little bit like, in venture capital, we talk about the J curve. You invest, you have lots of losses, and then the winners compound. There's a J curve of delegation, which is it literally is faster and better to do something yourself the first time. And lots of people are like, I can do this faster or better, but the hundredth time, it's not faster and better. And so, you have to be willing to go through the training, the handoff, the mistakes, the breakage, the feedback to eventually get to the point of compounding benefits.
Eric Jorgenson: So, what are some of the most surprising things that you've delegated that people would be like- make them very uncomfortable to hear that you delegated?
Jonathan Swanson: So many things. Okay. So I'll answer your last question, which I didn't get to, and then we'll do that. So I have different assistants and we have them broken down by different areas. So one helps me work, email, inbox, et cetera. Another helps me with finances. So P&L, balance sheet, angel investments, payments. Another helps with home. And so, stuff's breaking, booking Thumbtack pros, all that sort of stuff. And then we have one for kids and travel. And then there's a chief of staff who sits on top and manages everything. And so, you start with one, and then as you get capacity, you add more and more. In terms of crazy stuff we've delegated, I mean, I'll give two examples. One, have you heard this Shanna Swan book Count Down? She was on Joe Rogan's podcast. The book is basically about how male testosterone levels have been decreasing 1% every year for 30 years. And that's led to lower fertility, all sorts of sperm count issues and stuff. And if you have young kids, her recommendation effectively is testosterone is falling because there's plastic everywhere, all through your house, in your soaps and detergents. And so I heard 20 minutes of this podcast. I'm like, well, I want to protect my boys, both figuratively and my actual children. And so I sent my assistant a note and said, hey, go watch this podcast, buy the book, read the book. Find all the recommendations, put the recommendations in a spreadsheet, and send it to me. So she sends it to me and it's a list of like 50 things you need to remove from your house. I'm like, okay, now work with our house cleaner to find all these things in the house, take them out, throw them away and order replacements. And then there's a couple cycles of this. This was like a six week project to fully execute and just like totally nuts to pull off and the sort of thing that would just like absolutely never do on your own, because like you just give up. It's just too hard. But if you have someone there to help you, they can do it. So that's kind of like a health oriented crazy one. A personal oriented one that I highly recommend for people is doing gifts to friends and family that you could otherwise not do. So, for my dad's 85th birthday, which is coming up in February, hopefully he's not listening to this, I have an assistant who is going through all of his Facebook friends and DMing all of them and asking for a memorable story or memory with my dad. And then she's collecting all of them. And then on his birthday, I'm going to give him a book with like hundreds of these things. And it's taking her weeks to collect all of it. But it's going to be one of the most meaningful gifts I ever give him. And it took me 30 seconds to come up with this idea. And now I have someone working on it for weeks to actually deliver it. And that is like superpower of leverage.
Eric Jorgenson: That's super cool. I think so many people I think a lot of times have an adverse, like have an aversion to it right off the bat of, like oh, you delegate your gift giving and... There's like an impersonal way to do that and then there's the like, holy shit, this would be impossible any other way. And that's a really cool story of like- So are there frameworks around that of like, how do you train yourself or come to the habit of thinking like, what do I do with 100x the hours? I feel like that's such a creative act to like have this broader scope of what becomes possible.
Jonathan Swanson: Yeah, so this is a counterintuitive learning that I've seen in myself and from the best delegators at Athena, which is lots of people think that you have ambition and unlimited vision for all the things you can accomplish. And so then you hire an assistant and that's how you accomplish them. But the causation is actually the reverse. It's as you get leverage, the cognitive load of all of the admin and little things in your life lifts. And for the first time, you raise your sights and you're like, whoa, I have time to do more things. I could give more generous gifts to my friends. I could start a new business. I could be more ambitious. And I think people's ambition is typically hemmed in by what they think is possible based on the tasks on their list. And so, I felt this personally as I've layered in more assistants, my ambition just kind of grows. I'm like, well, what if I do more and more and all these other things? And I didn't feel that way before. Cause there's times at Thumbtack where you're working so hard, you're just buried and you're like, I can't possibly take on something new. I'm just trying to figure out today. And so, my encouragement to people is like you just start by delegating. If you don't have enough money for even an assistant, start delegating to Chat GPT. You go to Chat GPT and you say here's my top two personal professional goals today or this week or this month. What are steps I could take to actually actualize this? And if you got a little more money, hire someone at Upwork for five bucks an hour, and that lets you start acting on it. If you got more money, then you can work with Athena or an in-person assistant, and you can get more and more leverage the more you pay. But I would just encourage you to, you got to start, and then it can compound from there.
Eric Jorgenson: Yeah. I mean, this is exactly what my leverage course and expanding the book and stuff is about. It's just trying to see your, a career is not even really the right word, but like life, your scope of work as like compounding and using well leverage over the long course, whether it's people or capital or tools or products or whatever, like figure out how to do some work today that will make tomorrow, make yourself more effective tomorrow. And Athena, I think, gets this more than any other company I've ever seen, like talks about it, builds playbooks, trains EAs in this, trains us like as customers, clients, whatever you call us, I know with certainty I'm the problem. I know I'm not in the top 10%, if not 50% of delegators, and I'm leaning on Athena and appreciate all the resources and work and effort gone into coaching me. I think it's a mistake, as you point out, to assume that the EA is just going to show up and magically know everything that they need to know about you and how to make your life easy.
Jonathan Swanson: Totally. Let me answer that question, but let me turn the light on because the sun’s setting, so it's getting a little... Yeah, you were saying the...
Eric Jorgenson: Appreciating the value of training me because I know I'm the problem.
Jonathan Swanson: Yeah. It’s a partnership. EA needs to be trained. Client needs to be trained. And the better, the more both invest, the better you get. And I think for- so like, what are the limiting factors for most people? I would say number one is belief that it's even possible to live a life of time abundance, to accomplish more, to have a hundred hours in the day. I think lots of people don't believe that's possible because they've never seen it or experienced it, and I probably wouldn't if I didn't experience it myself. But you have to have that belief, and you talk to people like me and others and you're like, all right, it actually is possible. So, I could do it. The next is just like the desire. Like, do you want that? Do you want to have more in your life? Do you want to spend less time on things? Do you want to start more businesses? And then the third is more practical, like tactical. How do you actually go about and do it? And that depends on your budget. And the more budget you have, the more you can spend. But there's ways for everyone to get started. And then there's also, I'd say, limiting beliefs. I feel guilty to have someone just focused on me. That's something some people sometimes think. And I tell people to flip that around of like, hey, when you don't delegate and you don't offload things, you're actually withholding a great paying job to someone who desperately is excited to have it. And our assistants are so excited to work with you for years and have a great paying job. And so the more you delegate, the more you're helping a good hearted person somewhere in the world. So that's like one limiting belief. Another is this, what I call the cardinal sin of delegation, which is the more you- or it's faster and better to do it myself. And it's the cardinal sin because it's true. But it's true the first time and not the hundredth time. And so you have to go through that J curve. And then I'd say the third mistake or limiting thing for people is they don't invest for the long term. And they think they can just try it for a couple months or try an assistant for six months and then try a new one. Like in venture, compounding is so good. Compounding gets all the good things in life. You make money, you build relationships, and you build powerful assistant partnerships. I've been working with one of mine for over a decade. She's like my little sister now. She knows everything about me. I love her. She's seen all the ups and downs. She's been in my inbox during days where you get a term sheet for $100 million and days where you're getting lawsuits and you think the company is going to die. And there's not many other people in the world other than my wife who've actually seen all of that. And so, that longevity and compounding is super powerful. So, you’ve got to sign up for the long game if you really want to get the big leverage.
Eric Jorgenson: Yeah. And I think, I mean, I'm three or four years in with my EA too. I testified to that and the importance of trust, to fully trust this person with all the information about your life in such that they can act as you in a bunch of different really important contexts. That comes with time and reps and that compounding is a really important part of it. If you'll indulge me again to double-click on the belief, if that's the first limiting belief or limiting factor, I think you and Robert, who's also been on the podcast a couple of years ago, are the best examples I've ever seen of this. And Ray Dalio actually talks about it too, but I don't know him. What does a day in your life actually, what does it look like to actually have 100 or 200 hours a day if you've got multiple EAs working with you? How do you set up your day when you have all these resources and how do you figure out where to allocate your time, especially between I imagine there's all this pressure to be productive with all that time that you're paying for to buy back, how do you think about your leisure time and your productivity and your health? What does a day in the life of a super highly leveraged person look like?
Jonathan Swanson: I started with one, got more over time, and I always felt this time constraint. There's just so much I want to do and not enough time to get it all done. Eventually, I had enough assistants who were helping me with different projects and offloading all the things for my life that it happened when I got sick. I had this moment where I was like, I actually don't know what to do to do this afternoon. I've got people handling everything. And that's how the ambition expands of like, whoa, okay, what can I do to be more proactive? What's a new business to start? How can I support my friends or family more? So that's the trajectory. I'm sorry, I just got distracted by a message over here. What was the original question?
Eric Jorgenson: I was just thinking about like a day in the life and how you determine between pleasure, leisure, business, like incremental time when you're spending so much to buy your time back.
Jonathan Swanson: Yeah. So it's been different, different times. Sometimes you're in intense work mode and you're like working a lot and your assistants helping take care of your life and family and kids. And then there's been other modes where I'm more in freedom mode and like I want to do half a day of meetings a week. So just meetings on Tuesday, no meetings the rest of the day. And I want you to protect me from as much as possible. So try to protect me from emails, messages, calls, handle them proactively. And the first I want to hear about a task is when it's done in some cases. And now that is very difficult to achieve. That's the like, I call it the Nirvana of delegation, like this clairvoyant delegation where you've mind melded so much with your assistant that they're able to anticipate the things you want, complete them, and then you only learn about it when it's done. And so you can't start there. You start with, here's the specific tasks I want. Then you typically graduate to here's a project. It's a bundle of tasks. I want you to figure out some of the tasks that I haven't even delegated. And then eventually you delegate to goal-based delegation where it's, hey, here's what I want to accomplish. I want to spend more time with my kids or more time learning tennis. Can you help me achieve my goal? And then, the next level I call process-based delegation, where you actually take your internal algorithm and you export it as you delegate. And this is often natural for systems thinkers but more difficult for others. So as an example, if you want to have your assistant help you plan a dinner party, if you say, hey, can you help me plan a dinner party? Eight new people, I want to make friends. If they're your new assistant, it's very unlikely they're going to deliver the dinner party you want. But if you say, hey, here's how I think about dinner parties. I want Eric there. I want eight other entrepreneurs who are like him. I want it to be a variety of industries. I want them to all have the same number of employees or investors. I find these people by going on Crunchbase or wherever. Here's literally an algorithm and a playbook and a step-by-step. And if you export the algorithm, the preferences, you create the step-by-step, then the output is going to be much more closely aligned with what you want. That takes more effort and work up front. And so, this is where like the best EAs are paired with the best clients because the clients who invest that time make their EA better.
Eric Jorgenson: And were there moments in that like scale up of the EA team or whatever you call it, like where you find you were overloading one EA with all the different context switching you were doing, and you found you got unblocked by being like, all right, I got one EA for work, I got one EA for life, I got one EA for home? That's one of the problems I have... I'm juggling too many things, and so I do a bad job of prioritizing with my EA, and then it's very hard for him to keep up with all the context switching that I'm doing because I'm already doing more than I should.
Jonathan Swanson: I mean, being an EA is a tough job. And we find people who are excited for the challenge, but you don't know what's going to come. It's like I'm going to be asked to help plan a podcast or plan a wedding today. We'll find out. So, I mean, I think you as a boss, it's important to help your team know how to prioritize and they don't know the priorities in your head unless you share them. And so, I think that the limit for lots of delegators is they just don't share enough context. I mean, this is true of talking to Chat GPT 2. It's like the model doesn't have enough context, it just can't work. And so you need to export as much thinking, context, preferences, prioritization as you possibly can, so that the human assistant or the machine assistant can deliver the results you want. And that takes a lot more effort, especially when you're busy, you're jumping between things, and you don't always feel like you have time. I mean, one tactical thing we talk a lot about at Athena, I don't know how much you do this, but voice-based delegation is much more powerful than written delegation. And the reason is because you can talk three times faster than you can type, so just more bandwidth. And you can do it in situations that are more difficult, walking between meetings, jumping up from a dinner.
Eric Jorgenson: Driving, working out.
Jonathan Swanson: Yeah. And you're more likely to say a lot more. And so if you just start rambling, you just share a lot more context about exactly what you want. And if you- that's the like kind of one tactical thing you can do as a delegator to typically uplevel the fastest is just move to voice based for almost everything. And if you do that, you'll get more context and more feedback naturally, and you won't even know it. And that will help your assistant be better.
Eric Jorgenson: Yeah. If you're just thinking about it as a bandwidth problem, what's the lowest friction way to just externalize all of those priorities, preferences, and processes, as you said.
Jonathan Swanson: Yeah. It's not Neurolink, but it's a step faster.
Eric Jorgenson: It's a lot better than thumbs.
Jonathan Swanson: Yeah, exactly. Thumbs are the worst. Voice, you're still grunting into the air, better. Eventually, we'll just mind meld and we'll have full digital replication, and delegation is going to be insane.
Eric Jorgenson: Yeah, I think... even there's a step in the middle that I think Facebook launched one consumer version already that like the bit rate of like mental typing, so you like imagine typing and there's like a wrist monitor that's tracking your like micro movements or whatever. This is already faster than typing, which is wild.
Jonathan Swanson: I mean, it's cool. I mean, one thing we've trialed that is going to be- it's going to take us some time to build, but is we built an internal demo of a system that watches your screen as you work, runs the images through an LLM to find things you could be delegating, and then proactively hands it off to your assistant to start working on as a machine-generated delegation. The person who built this internally has done it with his assistant, and the majority of his delegations are now machine generated, which is pretty cool. And now the assistant has to decide, is this relevant? Would Eric actually want my help with this? Maybe he'll do it himself. And the human is still paramount and always will be. But can the machine kind of identify opportunities more naturally and more automatically? Definitely. Doing this in a privacy secure way is difficult. So that's why it's not something we've launched. But that is where I think delegation ultimately goes is you're just working. And there's a machine assistant watching you and it finds things that the human could help you with.
Eric Jorgenson: Yeah, that is a really cool- I mean, that's similar, Rewind is a product that has basically that level of access, but it's stored locally. So yeah, I'm sure it's doable.
Jonathan Swanson: Yeah, Rewind and they run in Meta.
Eric Jorgenson: Oh, really? Oh, I didn't see that. Cool. Good for them. It's a really cool product.
Jonathan Swanson: Yeah. Perfect memory, perfect recall.
Eric Jorgenson: Yeah. Of everything digital, which so much of at least remote workers' lives are now. That's absolutely rad. How has- I mean, so much of what your EAs work on and you experience is also like deeply intertwined with family life and you've got a family. Are they just on this adventure of delegation with you and the EA is going to feel like part of the family and it's just like a big happy squad?
Jonathan Swanson: They are definitely part of the family, part of the crew. One of my assistants, we moved to a house for the summer in the mountains and she came to help us set up and she's connected with everyone. Yeah, she's part of the family. And my wife is a very good delegator, too. I mean, you asked like crazy stuff we delegated. One of the craziest things we've ever delegated was Catherine's idea, which is, when you have young kids at night, they sleep and sometimes they wake up and they're crying. And you have a baby monitor that wakes you up, and then you see, should I go in or should I wait? And Catherine's like, what if we weren't listening, but we had an assistant in the Philippines listening? That is insane. And I love it. We now have someone in the Philippines who watches our baby monitors at night. And if the kids need intervention from us, of course, we go in, they call us. But 90% of the time, they actually don't need intervention. It's just kind of like a cry or they go back to bed. And so, we have probably 10% the wake-ups at night that we used to have. And it's someone in the Philippines who's like, yeah, it's like an auntie who is part of the family now. That is black diamond delegating. I would not recommend that for everyone. We are a little crazy, but I think, yeah, it's been one of actually the favorite things we've ever delegated.
Eric Jorgenson: I do love those examples that just push your boundaries of your perception of the possible. And that's not so crazy because that was the seed of the idea that turned into Harbor, which Kevin took and started as a company now.
Jonathan Swanson: Yeah, that's right. I mean, he called me when he started the business, and he's like, hey, I read your blog post about this, and I'm going to start the business doing it. I'm like, hell yeah, that's awesome. And he has kind of a vision with nurses involved too. So, you can have a nurse or a doctor call in, which is even better.
Eric Jorgenson: Yeah. It's a really cool- it's a clever thing. And you never know the price that you're willing to put on sleep until you have a newborn in the house. And then all of a sudden, your willingness to pay is like, oh my God.
Jonathan Swanson: Totally. I mean, Brian Johnson says, I mean, he does a billion things, and he says sleep is the foundation of everything. Because if you don't sleep, then you don't exercise in the morning. If you don't exercise, you don't eat well. And then now your health is totally destroyed. And so sleep is the foundation of all of it. And I would actually say learning to manage your time is even more foundational than sleep, because people don't sleep much, not because they don't want to, but because they don't have time to. They're trying to stuff everything in the day. They got work. They got family. And so, if you're health-oriented, figuring out how to own your time with delegation then gives you the power to sleep, and then all the good things come from that.
Eric Jorgenson: They're working late, they're stressed about the open loops.
Jonathan Swanson: Yeah. There's this like cognitive load from all the things you have to do that weigh on you. And you can think of an assistant as almost like a cognitive prosthesis that is expanding the scope of your brain to not have to handle certain things and firewalling it from a bunch of these loops so that it can be calmer, have lower cortisol, more focused, and yeah, more prepared for more important stuff.
Eric Jorgenson: Awesome. So, as we wrap up here, the final question that I like to ask founders is like, give me the 2050 version of Athena. What's like the most wild kind of like limit of possible vision of what this company can become over like the limits of your imagination over like two to three decades?
Jonathan Swanson: Whoa, I love that question. I met a crazy delegator who is a billionaire. He is an investor. He has a personal team of 50. On that personal team of 50, eight of them are executive assistants. All of the executive assistants are hired from Princeton. And I asked the person leading the team, how do you decide what to prioritize? You have this huge team. What do you work on? And she said, if my team can spend 24 hours to save my principal one minute tomorrow, so he can spend one more minute with his investments, his family, his personal interests, it is well worth our time. And when I heard that, I was like, whoa, that is insane. That is like hashtag goals. But I think that is what's possible for all of humanity by 2050 is, not everyone's going to be a billionaire, but you're going to have a human assistant powered by Athena, and that human assistant is going to have thousands of machine assistants that are going out and running errands and checking things and double checking and remembering everything, and the human is still there as the UX as your counselor, but your Athena assistants can be managing, yeah, maybe a thousand of these machine assistants, and you're spending more time with your family or start five new businesses and you'll just have a lot more optionality in how you want to live your life.
Eric Jorgenson: That's awesome. Thank you so much for taking the time and leading the way and being such a shining example of delegation effectively done. I appreciate you and everything you built.
Jonathan Swanson: I appreciate you too. Thanks for all the support, and you are a good and natural delegator, even if you are very humble about it.
Eric Jorgenson: I'm working on it. I'm working on it. One day.
Jonathan Swanson: Awesome. Thanks for having me.