
Loading summary
Jonathan Swanson
I never had assistants or service providers or house cleaners in my house, and not a world I was part of. But when I graduated from school, I worked at the White House and the White House. I sat next to the President's executive assistants in the West Wing. And as you might imagine, these EAs were really good and it set my bar incredibly high. What if I had a team of assistants like the President has? Not the President, but what if I had that same team? What could I accomplish? I hired my first assistant in the Philippines. As we were scaling the business, she really transformed what I was capable of doing. Helped me scale the business, helped me scale myself. She helped me make friends out of work, helped me meet my wife. All sorts of amazing things. The most valuable asset in the world. It's not gold or Bitcoin or Nvidia clusters. It's time. We all have a fixed amount of time. It's forever fleeting. And Athena's mission is to give people more of that most valuable resource so they have more time to build their business sometime with their family, whatever matters most to them.
Alex Wilhelm
This week in Startups is brought to you by Gusto. Check out the online payroll and benefits experts with software built specifically for small business and startups. Try gusto and get 3 months free at gusto.com/ Crusoe Cloud Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit Crusoe AIBuild to reserve your capacity for the latest GPUs today and northwest Registered Agent. Starting your business should be simple. With Northwest Registered Agent, you can form your entire business Identity in just 10 clicks and 10 minutes. From LLCs to trademarks, domains to custom websites, they've got you covered. Get more privacy, more options and more. Done. Visit northwestregisteredagent.com twist today.
Jason Calacanis
Hey, everybody. Welcome back to this week in Startups. I'm your host, Jason Calacanis. With me again, Alex Wilhelm. And we have a special guest today. Let's get right back into it, folks. Jonathan Swanson. I met you, gosh, 12 years ago. I was doing a little thing called Open Angel Forum. You and our pal Marco were trying to build a little startup called Thumbtack, but you had a problem. You're trying to raise money. It was hard to raise money.
Jonathan Swanson
That's right. You. You said, jonathan, come pitch me and my friends and we'll see what we can do. And we met up at Steakhouse. We pitched you and a dozen other people and it catalyzed our angel round. We had been looking for money for A couple months. And you catalyzed the whole round. JCAL first investor in. And that set us off on a trajectory to build the business. We built now, which is doing around half a billion of revenue, very profitable, growing nicely, supporting hundreds of thousands of small business owners. So it's been a fun, fun journey.
Jason Calacanis
Amazing. It's really interesting what small acts can do in your life. Like, at that time, there was no angel list. And I just had lunch with Naval recently. We were reminiscing about, my Lord, how far the industry has come. But at that time, the angels there were like maybe a dozen in each of the major cities, a half dozen in New York, a half dozen in la, two dozen in San Francisco. And it was really hard to figure out who they were, but they were charging founders, Alex. $5,000 to go to Koretsu Forum and these other things.
Alex Wilhelm
That's right. It was pay to play back in the day.
Jonathan Swanson
It wasn't just that there weren't many the founders had to pay to pitch.
Jason Calacanis
It was bonkers. And you probably got pitched on this. Yeah, Jonathan.
Jonathan Swanson
Of course. And yeah, I think you started. It was open Angel Forum or something like that, which was you come pitch and we give you money, which is much better deal for the founders.
Jason Calacanis
Well, I just had this. I was talking to Ruloff at the time and Michael Moritz and the team at Sequoia, where I'm actually today, because we just had our accelerator class graduate. And I didn't have an accelerator back then, but I just did the very simple thing, which was take tell us your idea. And then here are actual real angel investors, not lawyers, accountants, recruiters, trying to sell you something. And you don't need to pay me. Why do you need to pay me? It's just burgers and beers. We do it at somebody's house. We'll have the angels pay because they're rich. The end. Full stop. And so very proud of all the work you did at Thumbtack. Tremendous success that company's become. The original idea, a marketplace for services. But it was like a directory a bit more. The first version was like a Yelp directory, just of services. Correct. And then it went to this cost per lead. Hey, tell us what you're trying to accomplish. Fill out a dossier of hey, I want to paint my house, or I want to paint the cabinets in the kitchen, et cetera. And then you could get really customized quotes. Yeah, exactly.
Jonathan Swanson
I mean, when we started Thumbtack, it was Amazon sells products. Where do I hire handyman, house cleaner, dj? Nothing existed and so we started Thumbtack to be the Amazon for services. Yeah, started as a directory, as you suggested, and it's increasingly become a booking engine where you come, you tell us what you want and we instantly match you with professionals with their reviews and prices and all that. So you can go from idea to actually hiring a pro as quickly as possible.
Jason Calacanis
Incredible. Really simple idea. I remember, you know, a lot of those early investments, Jonathan. They inform what I do when we have scaled the firm to a hundred investments a year, 150 investments a year, and one of them was Product Velocity or people who are really good at design. And I don't know if it was you or Marco or who on the team was the standard bearer of design and of Product Velocity, but when I saw those two things with your firm specifically, and then later with Calm and later with Superhuman, later with Robinhood, something clicked in my mind. Things are not designed well or UX is not magical. User experience doesn't happen by accident. It happens because somebody deliberately made it so. And I'm thinking about the first version of Thumbtack and when people were using Craigslist, somebody had the insight, well, what if somebody from Craigslist comes and robs your house, which was a thing in the past. People would then go to your house to give you a quote and then rob your house, you know, and you might do something stupid like, oh, the gate code's 1, 2, 3, 4. Go ahead, come on in. You had a verified ID. Somebody uploaded their driver's license or somebody. You verified their mailing address by sending a postcard to them. This was like mind blowing stuff at the time. Maybe talk a little bit about that and then we'll get into Athena.
Jonathan Swanson
I mean, Craigslist is wild west of the Internet anarchy. And it was good for its stage. But obviously for trusted interactions, you want to have background checks, you want to have professional license verified, you want to have reviews from 100 different customers. And that's how you actually know if someone's going to do a great job. So we invested in all that from the beginning so it could be the most trusted place to hire professionals. And I actually remember the first lunch after you invested. You came to our office and was like 12 of us and you said this exact same thing. You're like, I'm just been playing with the Path app. I don't remember this.
Alex Wilhelm
Oh, gosh.
Jonathan Swanson
Path had these delightful little interactions when you push things that just had this extra touch. And you told our whole team, adding that extra touch can add some magic to the experience. And I think the team took that to heart.
Jason Calacanis
I remember that really shitty office you had, and it was like a dumpy kitchen. And we were in the kitchen at like two or three awkwardly sized tables that didn't balance properly.
Jonathan Swanson
It was proper startup between 6th and 5th, which is between kind of nice square area at the time. And then like the end of civilization.
Jason Calacanis
Yes, yes, exactly.
Alex Wilhelm
So it does have a lot of those fault lines. How long were you in the tiny office, Jonathan?
Jason Calacanis
Starting a house?
Jonathan Swanson
We were house for a few years. I lived in the closet for two years. Fun fact. And then we moved to that office, which was actually an upgrade. Oh. We were in that office for a few more years and then, you know, five, six years in, we moved to a proper office. It was fun to invite friends to.
Jason Calacanis
And really, interestingly, it was one of my first five Sequoia Scout investments. I'm here at Sequoia today, where Rule of created the Scouts program. Both of them. And they used the Scouts program to explicitly come up with an early warning signal for quality startups. And they wound up doing your Series B.
Jonathan Swanson
That's right. Yep. I recognize that, officer. And they came in for our Series B and led a number of increasingly big rounds. And then amazing partners. I think when you talk to founders, everyone loves angel investors because they're founders and they're on your team and they know what you're going through. But when I talk to founders, I'm like, you want those people around the table, that's the first round. But then eventually you need a Sequoia or investor at that caliber because they really raise. Yeah. Your aspirations and your ambitions significantly.
Jason Calacanis
Unpack that. How so what was your experience directly with Rule, off the team at Sequoia, whatever. In terms of expanding?
Jonathan Swanson
The first thing is you walk into this office you're in, and when you walk in, you see the S1s of Google, Oracle, Instagram and all. All of these legendary companies. And then you see the photos of the founders from all of these legendary companies. And Sequoia tells you, we see every deal and our goal is to pass on everything. But the companies we think can be legendary can be generational. And, you know, we are always ambitious and we thought this could be a big business, but having an investor like that select you and then put you in that same realm, it just raises your ambitions. And you're like, all right, let's don't. Let's not go for 100 million in revenue, let's go for 10 billion.
Alex Wilhelm
There you go.
Jonathan Swanson
And let's Build? Yeah, let's build something that's generational, and that's something that Sequoia talks a lot about, is generational. Obviously, Sequoia Tree speaks to that. But you're not trying to build a business to flip in two years. That's not how you build something important. You gotta build something that lasts for generations, and they do a good job of really hyping up that potential.
Jason Calacanis
Being a founder is a lot of work. You have to focus on your fundraising. Then you gotta hire the perfect team. Oh, gosh. Product, market fit, finding your first customers. But all of this means nothing if you're not actually a real business that's structured properly, giving your investors and clients the confidence to partner with you at launch. We're constantly recommending Northwest Registered Agent to our founders because for just $39 plus state fees, they will act as your registered agent. That means they take care of all the paperwork, making sure your business remains compliant, protecting your privacy and more. And as a founder, hey, man, there are so many organizational odds and ends that you have to worry about, so why not have a partner who can focus on all those little details? Then you can obsess about your customers. And Northwest Registered Agent is even going to help you set up a phone line, a professional email account, and find. Find you a great domain name. So here's your call to action. Go to northwestregisteredagent.com twist to get your company set up the right way.
Let's shift to two years ago, you texted me, like, just coming out of the pandemic, said, hey, can we get something to eat? Jonathan, you know you were the first investor in thumbtack. Want to talk to you about my new project. And I said immediately, like, yes, let's do it. Yeah, take us back to that dinner and what you built with Athena.
Jonathan Swanson
Just to give a little background on it. The I grew up in the Midwest. Midwest boy. Parents were farmers. I never had assistance or service providers or house cleaners in my house. And not a world I was part of. But when I graduated from school, I worked at the White House, and the White House. I sat next to the president's executive assistants in the West Wing. And as you might imagine, these EAs were really good, and it set my bar incredibly high for what executive and an assistant partnership could look like and how transformative it could be. And so when I went to thumbtack, I said to myself, what if I had a team of assistants like the president has? Not the president, but what if I had that same team? What could I accomplish. And so at Thumbtack, I hired my first assistant in the Philippines. As we were scaling the business, she really transformed what I was capable of doing. Helped me scale the business, helped me scale myself. I can tell stories about how she helped me make friends out of work, helping me and my wife, all sorts of amazing things. And then as I moved to chairman at Thumbtack, I said, you know, the most meaningful thing for me to tackle would be to give people more time. The most valuable asset in the world. It's not gold or bitcoin or Nvidia clusters. It's time. We all have a fixed amount of time. It's forever fleeting. And Athena's mission is to give people more of that most valuable resource so they have more time to build their business, some time with their family, whatever matters most to them. And the way we do that is we match you with the best human assistants powered by the best AI.
Alex Wilhelm
I'm really impressed by how many assistants you currently have working for you. Jonathan, I think you told us you have six kind of a chief of staff and five others. How do you manage a cluster like that and what's the incremental value you get from each? You know, next assistant you add to your team.
Jonathan Swanson
I've never start with six. Everyone should start with one. What I say is if, if you don't have assistant, you are the assistant. So start with one should be your first hire if you're building a company. And if you don't have enough money to hire assistant, use ChatGPT as your assistant. Sure, I can give you advice on how to use that as your assistant, but once you have the cash for your first assistant, then you bring on a team to help offload the most immediately painful things. And so first assistant really helps take the pain away. That's passport renewals, scheduling inbox, all this admin. That is a cognitive load that holds you back. And as you add an increasing number of assistance, you can move from just taking the pain to actually raising the horizon of your goals and what you hope to accomplish. And I think most people live in a world of time constraint. Yes. Where they never have enough. Lots of people won't believe this because they haven't experienced it, but I've experienced it. It's possible to have time abundance. I only achieved this when I had a chief of staff in six. The chief of staff in three was not enough, but once I got to six, it was the first time where I was like, wow, there is someone handling every part of my life. My House, my kids, my travel, my work. I have time to dream big and think about what's next. So for my team, chief of staff sits on top. And then each EA specializes. I have one that focuses on finance, P and L angel investments.
Alex Wilhelm
I presume the average Athena customer, though, has. Has one. Probably. Is probably the median.
Jonathan Swanson
Yeah. Most people start with one and then they add a second or a third.
Alex Wilhelm
Oh, wow.
Jonathan Swanson
Co founder gets one.
Jason Calacanis
I have two. And what I decided to do in this grand experiment and to give people a background on this, they're $3,000 a month. Athena trains them. Athena matches them. If it's not a fit, they replace them. So I'll tell you my experience. Previously in the Valley, an EA is 100 to $150,000 a year. Most people do not want to be in that position for more than one year, six months, 18 months. They see it as like, I'm going to be an EA for a venture capitalist, a CEO, an executive, and I'm going to use it as a springboard. And therefore you're spending more time replacing your previous EA than you are with an EA. So they'll stay for 12 months and you spend another six months finding one. You find that one. Turns out they're not great. You overpaid them, you got to fire them. You got it then has people throw up their hands and say, I'm not going to have any A. Which is what most founders do. And this is why when you pitch me the concept of Athena, I said, are you raising? And you said, from you? Yes. I want you to be my first investor because it got lucky the first time. I need that lucky jcal first investment. Which when I say my heart filled, it was like bubbling up with joy because Jonathan sat across from me at a Greek restaurant as I'm eating octopus and said, you know, having you as our first investor, we always thought was like the magic luck charm. So would you do that for me again, for Athena? And I was like, would I be the first investor again for an incredibly successful entrepreneur with his best idea ever? Yes. Here's a million dollars. Please, Lord. That's why we have this incredibly loyal, great relationship. And you hear me talk about Athena because it's one of the great transformative products like Thumbtack was, I have two. And what's really amazing about it is I had given up on the concept of an EA2 is 75k or 72k. But you remove all the recruiting and training part. You do get what you put out. You. They're not in person so they're not getting coffee for you know, the person so you're not getting that. But it turns out 99% or 95% fully is can be done remote and.
Jonathan Swanson
Maybe one day we'll, we'll have assistant can tell operate a robot in your home. We were joking about this but we're like, actually maybe in the next few years that's possible.
Alex Wilhelm
Three probably.
Jason Calacanis
Well, you know, you bring this up when I was doing Mahalo when you were doing Thumbtack, we were all experimenting with the Philippines and other locations where information workers were doing really well. I've stacked two of them and I can tell you there are things that I do that are 75k to 150k positions that I've been able to train them to do. One of them is to sort inbound and tag inbound applications from founders like Thumbtack was and Jonathan and Marco were at one point applying and they are able to tag and say this company has product velocity. This company has technical co founder. This has a developer. They've worked together before. They're able to like do that organization layer. The reason this is important for me is there are jobs that that group of people are willing to do in the Philippines or whatever location it is that I found Americans just don't want to do. And what happens at work is when somebody doesn't want to do something, they'll do everything else and put that last even though it might be first on your list as the CEO. So they're so stoked to make you happy as an Athena assistant that when I ask them, get me this is a stupid thing, but I'm a foodie. People know that. I talk about it. When I went to Mexico City recently, I said, here are my subscriptions. Monocle.com, conde NS Traveler Eater. These are the publications I like to look for for hotels. I like design hotels, restaurants. I like high, I like low. I like the low street food. Like the best stuff that Anthony Bourdain might go after and then the high end. It's kind of like an Anthony Bourdain strategy. Putting all that aside, I said, I'm going to Mexico City. I want a high and a low. I want a 530 and a 7:30 reservation. Book it, research it from these places, rank it. Tell me which ones have Michelin stars. Tell me which ones are on Yelp. Tell me the rating here. This is like two or three days of work, maybe two days of work and then book 10 reservations. So I don't have to even think about.
Jonathan Swanson
You just show up whenever you want. You miss the ones you don't.
Jason Calacanis
And I cancel those to be good to the restaurant. It was unbelievable of an unlock. Now, if I had asked, I would have been embarrassed to ask an American to do this because I would seem.
Jonathan Swanson
And if you had had asked, they would have just said no.
Jason Calacanis
Yeah. They would have been like, are you. I'll get you one. But why? They would have questioned it.
Jonathan Swanson
I think this is a key unlock for lots of people. The first unlock is learning to give up control and thinking it's actually faster or better just to do this myself. And I call that the cardinal sin of delegation because it actually is faster and better to do yourself once. But the extra effort you put to delegate that first time, then train someone else how to do it and so you never have to do it again. The second thing that often catches delegators is this kind of guilt of like, is it okay for me to do this? It feels almost unfair or not right to put this on someone else. And we really reframe that. And we say when you're not delegating, you're actually withholding a good paying job to someone in the developing world who desperately wants it. And we hire people who desperately are excited to have the best paying job of their life and to work with a founder in this exciting life. And they're there to support you and they get to be part of that. And so when you're withholding these delegations, you're actually withholding this opportunity for someone to get paid and to. And to learn. Yeah, I think lots of people have to reframe that to have the confidence to lean into delegation.
Jason Calacanis
Launching a new company is all about finding your first customers and then just learning how to solve their problems. And that is going to put you on a relentless pace. And that means you're going to be releasing new products and features hopefully at a brisk pace or better. But my lord, the complexities of working with AI, it's going to slow your developers down. You're going to have to install new GPU drivers, they're going to be provisioning clusters. All of this detail oriented, labor intensive work can distract you from working on the thing that you're building your product. But now there's Crusoe. They are the AI factory that worries about your backend so you can focus on your code. And their hardware has been designed specifically for AI development. So they're going to make sure that your models run with unparalleled performance every time head to Crusoe AI build to apply and receive $100,000 in credits for virtualized Nvidia GB200 NVL72 on Crusoe Cloud pending availability. Okay, that's C R U S O E AI Build to apply and get those hundred thousand dollars in credits.
Alex Wilhelm
You know Jonathan, when I was thinking about Athena in the era of AI, AI agents and so forth, I kind of thought that the human component might get deprecated.
Jonathan Swanson
Bit.
Alex Wilhelm
But researching and just prepping for our chat today, it's very clear that you guys think that humans plus AI is going to be this enormous unlock. Does the introduction of AI though limit the number of humans that I might need? Like for example, Might you be 3 Athena assistants in 5 years if AI continues to improve as it does?
Jonathan Swanson
It's a natural question is where lots of people go, our view is the human's going to always be in front. That's the ux. Humans are good ux. We like working with them. But behind the human there are machine assistants we're building that will automate more and more. Yeah, and it's going to be very similar to how Tesla did it. When Elon started Tesla, he did not build the cars without a steering wheel. There's a steering wheel because he needs a human to drive it. And he's progressively added automation. And so first there's auto steering and lane control and auto braking. And then over time it takes over more and more. And even with Waymo today, which are as full self driving as we have, they're actually human drivers in the cloud who remotely operate the cars when they're needed. And so we think a very similar thing is going to play out.
Alex Wilhelm
So where are we on the path from lane assist to full self driving in terms of bringing AI into the assistant principal relationship?
Jonathan Swanson
We're day one, we're the lane assist. Humans are predominant and the machines are now starting in Q1 of this next year at Athena, they'll start reviewing and augmenting the task. So when you delegate to your assistant, the AI will find ways to help draft, push it forward, do a subtask and then over time that will increase. And our view is not that we should break this one to one match between a client and assistant, but rather the client should do more. You can have an assistant that's twice as capable, does twice as much, and you can start another business, spend more time doing other things. And so we're going to push that as far as it goes. Now, if you're talking like a decade from now where one human assistant feels like 20 assistants a day. Yeah. Then maybe one human can support multiple clients at the same time.
Jason Calacanis
Also realize this is like unlock number three, perhaps is this group of individuals will embrace AI tools faster than my American employees. In 80% of the cases, they are AI. First, I don't know if this is part of the training program, but I told them get the Comet browser from Perplexity. Why? Because it's agentic and you can do things like. And I gave them the prompt that I had made into a shortcut which is please visit monocle.com, conde nastraveler.com Eater Michelin Guide and give me the consensus amongst those websites for the best restaurants, for the best hotels and put them into a table and give me the link to it. So then they started doing that, which meant they, they started on second base with their research. They weren't manually researching. So maybe you could talk about how do you train Athena assistants and select them. Both of those things seem to be kind of important.
Jonathan Swanson
First, we do things the right way. So in every country we enter, we set up legal entities, we hire full employment, we have benefits, we pay very well. Other companies in the space kind of fly by night hiring contractors. We do it the right way and we do that because we want the top talent and it's how you retain and motivate great people. And so once we have that stuff in place, then we have this huge funnel of talent. So we get 50,000 assistants to apply to Athena per month. So this huge fire hose and we put them through a huge battery of tests, many automated, to assess them across lots of different dimensions. For the very top 1% of that, we invite them to in person training centers. So we built four story training centers in countries around the world. They're like beautiful startup park. People come in, they do their in person interviews and there they get, if they pass in person interview, then they enter a multi week training program that's run by the former head of University of Michigan business school. We call it Athena Academy. We've actually got it accredited, so it's a degree offering college. And so our assistants get free education as they work with you. And if they stay with us for five years, they'll get a MBA degree from us for free. So not only do you get someone to help you scale your startup or spend more time with your family, you get to support someone getting an MBA degree for free. And we absolutely invest a lot in AI and AI training and all the tools. In fact, I got Word from our partner at OpenAI, they obviously have a million businesses using them. They said Athena was the fastest ramp of any enterprise they've worked with and the highest utilization per employee. So it just went straight up because it's built exactly for our use case and our assistants are trained on how to maximize the use of it. And that's kind of off the shelf. And now what we're building next is we're integrating that into all of their workflows so it will happen more naturally and more automatically without them even having to go to ChatGPT.
Alex Wilhelm
Is that a piece of software you might break off later and sell as a standalone entity?
Jonathan Swanson
A hundred percent. That is our secret plan. We're effectively building workflow management that will optimize how fast they can work, the quality, et cetera. We think the only way to build this is with a human that lived with this full system. Once it's working to the degree we are proud of, then we will take it to market. And then any assistant in the world. 10 million could use this as kind of a $200 a month SaaS offering to double their productivity.
Alex Wilhelm
How fast is the company growing today? I know Jason's an investor so he buys access to the data. I don't, so I'm curious. Athena makes a lot of sense for a lot of people, I'm sure, but I don't have a good feel for how fast the business itself is growing in its current stage of maturity.
Jason Calacanis
We have a good story about this growth.
Jonathan Swanson
When jcal and I met for lunch at the Greek restaurant, I bootstrapped the business to that point with my own capital. And I asked Jaycal, will you be my first investor? And he said yes on the spot, which made me love him again. And we were at about a 40 million run rate then. Today I'm happy to share we're exceeded 100 million run rate. So we've grown quite nicely and expect to continue that growth into next year. JCAL and I have some special deals that we're cooking up. I don't know if we can share those things yet, but we're cooking up some deals that will set us up for a big bang next year.
Jason Calacanis
We had a crazy moment because Jonathan said, I also want to make you like an ambassador, you know, an influencer for the company. And I said, well, I've never done that before, but let me think about it. And so we did a deal. And when you hear me talk about Athena all the time, I always use my Athena Wow. To get like a free Couple of weeks. So if you go to Athena wow.com, you get a couple of free weeks. But the reason I did that was I wanted to see if, you know, the podcast both all in and this week in startups, if would that be able to kind of move the needle? Sure enough, when I mentioned it on all in, my bestie Chamath was like, tell me about this Athena thing. I need an assistant. He was going through the same pain and suffering I was, which was, I can't like just take hiring people in the Valleys. You hire somebody for an extraordinary salary and they hate you for it because they have to drive an hour because they can't afford to live in Atherton or Palo Alto or San Mateo or San Francisco. So he got one. So the two of us then talked about it and we got rid of. I guess Chris on your team was like, hey, can you stop talking about Athena? For three months we ran out of inventory. We have no more assistants left.
Jonathan Swanson
We had a waitlist for many, many months because of this. I was basically like, most of us are happy the supply team is crying because the fact that we had to go hire a thousand assistants and we can do that, but just takes more than a couple of days. So we spent last year investing heavily in the supply side of the business. So we opened multiple countries, not just the Philippines, Kenya, Guatemala. We're building these training centers and we now have the capacity to scale to a pretty ridiculous level.
Alex Wilhelm
And so how many a month, Jonathan? How many new assistants can you get through through Athena Academy and kind of onto the system per month or quarter right now?
Jonathan Swanson
So 500 is kind of the max before things start to break at the current capacity. But we got more buildings going up as we speak.
Jason Calacanis
I think it's smart, you know, when you're an entrepreneur and you get product market fit, you can break it, right? You can build the skyscraper too fast, right? When you start doing that and you don't have a strong foundation, bad things happen. You probably experienced this. Yeah, of course.
Jonathan Swanson
I mean, thumbtack. I mean, thumbtack's been through all the ups and downs of every startup and we're fortunate to be in the strongest position in its history. But there's some really close near misses in thumbtacks history that you probably know about.
Jason Calacanis
Permission granted. Tell us the. Tell us the story.
Jonathan Swanson
The most memorable moment is I woke up one morning and I had an email from someone in the Philippines that said, jonathan, I just searched for thumbtack in Google and there's no results. And I was like, what do you mean? They're like, when I search the word thumbtack.com, it does not show up.
Jason Calacanis
Oh.
Jonathan Swanson
And I'm like, whoa. And at this point, we were heavily dependent on traffic from Google. And by the way, Google's also an investor. And so I look at analytics and traffic has gone to zero. We don't know why. We run to the office, we call our emergency meeting. And this is kind of the madness of a startup life is I've got 30 new employees who I'm doing new employee onboarding with. I'm telling them about the history of the company and I'm taking calls from the press and there's literally a journalist who's outside asking what's going on because things are starting to spread. And basically there was misunderstanding. Google thought that we had done something inappropriate. They had given us the Google death penalty, which is not that you're deranked, but you don't exist.
Alex Wilhelm
Just fully unpersoned.
Jason Calacanis
Excommunicated. Yes. You're no longer recognized by the gods.
Jonathan Swanson
Exactly. It's like a black site.
Jason Calacanis
Yeah.
Jonathan Swanson
It was a very intense couple weeks. We had to do a bunch of work to prove that we were in the clear. But we eventually got there. And I mean, in the midst of this, I was supposed to be flying to a friend's wedding to propose to my wife. Had to cancel all of those things. But I tell people now it's one of the my best, it's one of my favorite experiences because your back is against the wall, you have no choice but to do whatever it freaking takes. And you just lock arms and you're like, we're gonna do it. And then when you come out, you take a little breather and you're like, that was insane. Let's not do it again. But it was actually kind of a fun experience.
Jason Calacanis
Launch is a fast growing organization. We've got more than a dozen employees working with me here in Austin and another dozen spread out all over the world. But there's so many moving parts when it comes to hiring and managing employees. There's the onboarding, of course, payroll. You gotta pay them. And listen, I've got all these podcasts to do. I don't have time for payroll, benefits, HR taxes, answering questions, nor do I want to hire a full time person and then have them do five hours of work a week. No, I have the perfect partner, Gusto. They're the all in one payroll and benefit product that's built just for your small business. Easy to use. It's Incredibly fast to get started. And it's designed specifically with remote offices in mind. And Gusto is not just giving you helpful tools. They're going that extra mile to keep your workers happy and keep everything running smooth, smoothly. And they're now offering level funded health plans to keep your insurance costs down and on demand pay to help workers get access to their cash faster without paying extra interest or hidden fees. So here's your call to action. We want you to try Gusto today. So we're giving you three months free when you run your first payroll. That's right, three months free. F R E. That's my favorite price, folks. Go to gusto.com twist that's gusto. G-U-S-T-O.com twist what an amazing service. And a partner. Great partner.
Amazing. If you're going to be an entrepreneur, you got to be prepared for these kind of things. I have two Athena assistants and what I did was I said, let's have them every Saturday and Sunday. They said, hey, Jake Al, you don't need people on Saturday and Sunday. I said, I have a plan. Number one, I can afford it. I can afford to build out this infrastructure 365 days a year, so I'm going to try. Athena was like, okay, we'll roll with it. Then I said, here are two or three things you can do when these are big data projects. One of them was to take every episode of this week in startups in chunks and put it into a Google notebook LLM, take all of my hits on CNBC and the press, every podcast I've ever appeared on, and put them into different notebook LLMs to make LLMs of my appearances so that producers can say, hey, what has Jake Al said about Apple over the years on cnbc? And they can pull it up. I never had that ability, but they also empower that. And then on the weekends I say, hey, can you look at the Top 100 Podcasts? Use this tool Descript or whatever tool you want to use, whatever add to and just go through the sponsors. And here's my new director of sales, Ricky, who's unbelievable. Go into pipedrive and see if we've talked to that customer. When's the last time we talked to them? And put into the slack room, hey, these are seven advertisers on these other podcasts and here's the last time we talked to them. That's a backstop for Ricky and I and for the sales team to know if we're missing and we don't, you know, I don't want to highly paid salespeople, six figure people listening to other podcasts and timestamping and doing that work. This has been unbelievable for the sales team. And so when you are not utilizing your Athena assistant, Jonathan, you can give them backstop projects and they do it now. Well, you say, of course. I didn't figure this out for six months.
Jonathan Swanson
You know what I tell people is like, when they're like how what should I use an assistant for? I say, first make a list of all the things you don't like doing, you don't like, paying bills, calendar, inbox, et cetera. Start there. And then once you have that list taken care of, then tell me what your personal professional goals are. You want to make more friends, I can tell you. Your assistant could help plan dinner parties at your house every week. You'll make a bunch of friends. You want to give a good gift to your dad. I have an assistant today. Hope my dad's not listening. Going through his entire Facebook account and DMing every friend, asking for touching story or memory of my dad from the last couple decades, collecting hundreds of these. And then on his birthday in a month, he's going to get a book from me. It's a collection of all these amazing notes from all his favorite people in his life. And this took me 10 seconds to come up with. It's going to take my assistant six weeks to execute the project. It's a huge project, but it's going to be one of the most meaningful gifts I'm ever able to give. Incredible to me that just like, it feels so good. I get to give someone a good income and I get to give my dad this like amazing gift.
Jason Calacanis
Oh my God. So they could go interview people, get that video, save it, clip it, and just have it prepped for a videographer, a documentarian. Oh my God. So genius. I mean, the possibilities around this, it's really cool. I will say the other thing that's worked out really well for me is I wanted to do an activity with my 15 year old. And so I said, hey, set up pickleball for 10 weeks in a row with an instructor. Then I want to do like archery or I want to do. I just rattled off ideas with my daughter. One of them was like rock climbing. So we came up with like four or five concepts that are hard activities to learn. You know, like there's some activities, like if you want to play, I don't know, checkers, you can just start playing. But there are some that are hard for the first Two days, like skiing, golf, rock climbing, pickleball. You gotta learn the rules. It's just like you suffer for two to five sessions and then you actually start to enjoy it. So this was a concept I had to build grit in my daughters and to have an experience for us to build grit together and then get through the other side. My daughter, now 15, can play pickleball and she knows how to score and, you know, like it took seven, eight times but really worked out. They did all that for me. They coordinated it all. They gave me four choices for each one and it was arduous. And then I tried to get an archery folks to come to the ranch and set up an archery. They got me all these quotes, whatever. It was just like too hard to do. Nobody wanted to do it. But then we found eventually, like other activities. Another way to say it is it would not have happened without the Athena assistant.
Alex Wilhelm
So it sounds like you can either have an Athena assistant for your family, say, that does all of this amazing stuff for you, or you could have one child in private kindergarten because they're, they're about the same cost.
Jason Calacanis
Now if you look at, you know, $36,000 a year, which is one fifth the price in San Francisco and one third the price in any other city for this level of executive support or half, you can be inefficient with it and not feel guilty. I think that's like one of the things. And you can experiment with it. Yeah.
Jonathan Swanson
And if you don't have a lot of cash, then the first thing you could have the assistant do is help you save money. So, hey, come in here. Look through all my subscriptions, look through all my receipts, Help me, help me find ways to save money. Wait on the, on the phone for three hours to get a refund for this sort of thing. So lots of our clients will start with that because if you can cut the cost of your assistant in half on day one, then great idea.
Jason Calacanis
Makes it even easier when you look at your, you know, 10 plus years building startups. And we had a great question come in from the audience about product market fit. Techno Chief 2000 watching the live stream YouTube.com search for this week in startups and put on the. After you subscribe, put on the bell and you'll get an alert when we go live. Techno Chief asks, how do you know an idea has real market pull versus founder delusion? When should a founder pivot and when should they double down? It's a very open ended sort of question here because you have micro pivots mini pivots, all kinds of interesting things that occur. So tell me about your experience with that.
Jonathan Swanson
You know, I, I heard someone describe it as, you know, you have product market fit when it feels like the market has you by the nostrils and it's just pulling you.
Jason Calacanis
And I, it's uncomfortable.
Jonathan Swanson
At Athena, the first time I experienced that we launched the service and I didn't, I didn't know how much demand there was going to be. And a thousand people signed up in the first 24 hours and I'm like, all right, that means we have to hire a thousand assistants. That's not product market fit yet. It's product market fit for the idea we got to now deliver on it. And once we went live and we started growing, our growth was driven entirely by referrals. We didn't do any paid marketing, any ads. Our favorite clients told their favorite friends and that's how it grew. And to me, that is the definition of product market fit. When your customers do the selling for you, then you got a market fit. And now it's possible to build big businesses that require huge sales teams and lots of ad spending. And that can be, you can build big billion dollar businesses that way. But my definition of product market fit is your customers market for you because they love it so much.
Alex Wilhelm
Jason, good definition.
Jason Calacanis
I think it's extremely tight. Andy Ratcliffe, who's been on the program Wealthfront founding partner at Sequoia, great firm. He talks about this nostril pulling as like people are calling your office and telling you I want to Athena assistance. I need them to work this, I need them by this date. And then I'm doing six more here. In other words, your sales team goes from founder led sales where Jonathan is like explaining to me the concept and we're brainstorming how to onboard people, whatever. And that's founder led sales, right? It's really hard, it's arduous. It's like product discovery mixed in with sales. Then you hire a sales team, you try to replicate that, you try to make it in a process, right? So you have product market fit, but the sales team's then saying like I sold these people, but these people won't budge. You kind of have semi product market fit. Then at a certain point you have a salesperson, it's scaling, say like this week in startups and our ads or founder university, we have product market fit. We know we do. So it's okay. Can we scale it, not break it and then make sure you don't sell it to the Wrong people. So you're fine tuning. Don't sell Athena assistants to people who can't afford it. Don't sell it to people who are bad at delegating and who are control freaks and will never change.
Jonathan Swanson
It's a great point. They're, you know, one of the things we say is Athena is for clients who want to invest because relationships compound and you get what you put into them. And if you just expect to show up and your life is automated, it's not how it works. I've spent a decade getting to this point where I have time, abundance and I have all this leverage. And you know what we tell people is you got to go full time, you got to go all in. You have to give your EA lots of feedback. You basically have to take your personal algorithms and export them from your head into your assistant through lots of feedback and suggestions of many months. And if you're willing to put that effort in, then we say, then we want to work with you. But if you don't want to put that effort in, you're not set up for success. And it doesn't matter how good the assistant is.
Alex Wilhelm
What percent of potential customers fail that test and you tell them essentially this is not going to be for you.
Jonathan Swanson
Well, we tell people on the way in, so lots of people just don't sign up and then the sales team probably disqualifies 10 to 15% who just don't feel like they're, they're going to put the effort in.
Jason Calacanis
Raul over at Superhuman, who, when I was doing open angel for him, I did rapportive. So he was part of that first cohort of just brilliant founders when the industry was probably 10% of the size it is now. So it was much easier to find a great investment because there just weren't that many founders and just weren't that many investors. It was like a more boutique industry, less competition, less competition for dollars, less people involved. More people involved for the right reasons, less people involved for the wrong reasons. On, on both sides of the table. If people do are not willing to do an onboarding for Superhuman, the email product which is now includes coda, includes Grammarly, and I'm obviously an investor now in that larger company because they got acquired and they rebranded as Superhuman, which is wild. You would just say, you know, if you're not willing to do a 30 minute onboarding and learn the quick keys and have us to show you how to use it, you're not going to get value from it. So I don't want to Take a dollar a day from you. It's just that easy.
Jonathan Swanson
Our first learning when we started this business was we'll recruit and train assistants and then we'll match them and maybe that's enough. And we matched with the very first client. And the first client's like, how do I delegate my inbox? How do I delete my calendar? How should I do this? And we did the second client and they said the exact same thing. And so then we said, okay, we need to teach the assistants to be well trained, but we actually have to invest just as much in teaching the clients how to delegate. And so we built a delegation program. We've actually launched this new formal coaching program where if you want for an additional amount, you can get a delegation coach who will meet with you at a regular frequency and help you know what your goals are. Think about how to use your assistant to delegate. Help you find roadblocks when something's not working, help you problem solve it. And that kind of ongoing investment in your own skill of delegation is the. Is the really the key to getting to the next.
Jason Calacanis
That's where it kind of unlocked for me. And this constant feedback is the key piece. Today my Athena assistants, one of them said, like, there was just like weird sentence in the summary. I like them to give a summary of my calendar every morning, every day. Check it, look for duplicates, look for issues, make sure the link to the location I'm going works on Google Maps. Because sometimes people invite me to something. They put in a weird address. I'm traveling in Singapore. You click on it, it doesn't work. And then I'm like, okay, I don't know where I'm going. So they click on that ahead of time. They check it in Uber. They make sure Uber is working in that country. There's a lot of little details I've given them, but they put in like a sentence that was written by AI. And I said, what's this? And they said, well, I put my started putting my communication to you in ChatGPT. I said, please don't do that. I would rather have like a mistake in your grammar. You can fix the grammar, but don't have it. Give me a sentence. Like, if you have time between these two meetings, you can use it to catch up. But I was like, don't give me AI slop. Not for me. Maybe somebody else likes to have a bunch of flowery language wrapped around what they're doing. Not for me. Don't ever do it again. I don't want AI Slop. I want crisp bullet points, but this is like, you have to be willing to say, I want Chris bullet points. I want to train my Athena assistant to do it the way I want to do it, yada, yada, yada.
Jonathan Swanson
And if you look at the best assistants at Athena, it's no coincidence that they work for the best clients. The clients who are really good at delegating, who are just maniacs about building systems, those assistants become the best, but it's actually a partnership is not that the assistant's the best, it's the combination is the best. And so, you know, when someone feels like their assistant's not right, we first investigate the system to make sure they have the capabilities. But then we also look into the client and say, hey, maybe you actually don't know how to delegate, right? And we're going to give you feedback on how to. How to get more leverage out of this person.
Jason Calacanis
It is super important.
To have a playbook and a checklist. This is why I always, every single person who comes to work for me, I make them read the checklist manifesto. Because Jack Dorsey had read and I don't know, some interview with him or heard him on a podcast, and he talked about this book and how he gives it to everybody at Square or Twitter. And it turns out, like, checklists really reduce mistakes. We had a mistake today with a company we were syndicating and we skipped a part of the checklist. And it's like, if you make a checklist for your Athena assistance, for your researchers, analysts, your yourself, the chances of you making a mistake in highly repetitive tasks goes down in a massive way.
Jonathan Swanson
It reduces mistakes. It also explains your thinking. Like, if, you know, you want to plan a dinner party, this is. You know, when I was at Thumbtack during the busy days, I told my assistant, I don't actually have any friends outside of Thumbtack. I just work here all the time. So I need you to help me make some friends. And so she's like, all right, I'll help you plan dinner parties at your house every other week. And if I just said, plan dinner parties, she couldn't have done a good job because she doesn't have the context. She doesn't know who to invite. But instead, I did what you said. I made a checklist. It's okay. I want six to eight people there. I want them to have just raised capital. Companies like Uber, Airbnb, who are, you know, at the time, just tiny little startups. Invite the founders. Here's the message. Get a chef off of Thumbtack and I want to walk home from work at 8pm, walk into my apartment and there'd be eight new people I don't know that I get to hang out with for that night. And I dialed in that algorithm, that checklist and eventually it was just autoplay. And then I'd be like, hey, whenever I land in a new city, have a dinner party waiting for me, people I'd like to meet. And then you're just kind of meeting everyone. I made most of my best friends from these dinners. I actually met my wife at one of these dinners. And that's the sort of stuff that it starts with a checklist sounds simple, but it can become something bigger.
Jason Calacanis
You have an Athena assistant watching the baby in the crib. Is this. Or if you were worried about your kid, would this is an idea you came up with? It's creepy, but brilliant.
Jonathan Swanson
This is black diamond delegating. I'd like to clarify.
Jason Calacanis
Okay, Black diamond, double black diamond or black diamond feels like double black.
Jonathan Swanson
I do raise my children. I don't delegate the raising and loving of my children. There are certain lines. This actually came from my wife. She was like, you know what? We have this baby monitor on and when the babies cry, 90% of the time they don't actually need us. They go back to bed a minute later. What if we had someone in the Philippines watching the baby monitor remotely? And then there's an algorithm, a checklist. If they cry for one minute, don't intervene. If they cry for two minutes, play a lullaby. If they cry for three minutes, give us a call and wake us up. And we still use that today. We've got four kids now and 90% of the time the remote assistant and can actually calm the situation down. And we don't have to be called. But of course if we're called, we go in and, and we help our kiddos.
Jason Calacanis
Interestingly, we have a company we invested in Deep Sentinel. What they do is they have cameras everywhere that are two way cameras. They built this hardware. Jonathan, you're going to think this is hilarious, but they had the insight you had, which is there, hey, there's people around the globe who, you know, are looking for work. And this is work you're probably not going to get an American to. Especially now when we have 4% unemployment. I mean, everybody wants to, you know, argue about this, but we still don't have a lot of people. So here's this security camera. If somebody's in front of it, it does a motion detection. That red light starts going In a circle, as you see on the screen here. Then the microphone turns on somebody, a remote security agent, I'm not sure where they use them, starts talking to them and says, hey, you're trespassing. Person in the black hoodie. Now, I, I don't know if they're using us or not, but in the beginning, maybe they were using people in the Philippines. But anyway, it was. The concept is somebody could be doing this remote. It turns out most people don't need an on prem security guard. And the on prem security guard falls asleep, plays candy crush chess. Reasonably. It's like a boring job to look at eight monitors.
Jonathan Swanson
Yeah. You can have one human watching multiple houses. Eventually you can have machines watching. And so you have machines plus humans.
Jason Calacanis
As a backstop, which I think is where they're at is, hey, an alarm goes off, there's motion. What type of motion is it? So my security systems tell me what type of motion it is. Oh, that's your gardener. I have the facial recognition for the gardener. I don't get an alert for that, but if it's an unknown and, and this literally happened, a new gardener was sent. I got an alert. Oh, new gardener. Great.
Jonathan Swanson
Yeah, you create lots, prevent lots of dangerous situations with my night watch situation with our kiddos. Like we've had times where one of the kids was climbing out of the crib and about to fall to the ground is the first time they'd ever been able to climb.
Jason Calacanis
Yeah.
Jonathan Swanson
And we wouldn't have known about it until we found them, you know, crying, but instead the night nurse called us and we ran over and grabbed them. And having that human in the loop is pretty cool.
Jason Calacanis
So genius. Here's a question from one of our noties. The noties, just so you know, Jonathan, are my true, true fans. They are the notification gang. So we call them noti gang Noti because they have the notifications turned on and they're the first to come to the live feed. So noti gang member Pilgs P I L G S says, hey team, does Athena work with medical space? How do they handle EMRs and other HIPAA type systems? And he's on every day, so shout out to pils.
Jonathan Swanson
Yeah, great question. Are. So our employees are recruited, trained, and then managed and replaced by us. But then once they join your team, they go through all of the legal and onboarding that you would put them through. So if you have specific, you know, systems or security or rules that they have to follow, just you treat them like any other employee and you know, for Most of our clients, most of the company doesn't even know this assistant is necessarily from Athena. They're fully integrated. It's just their Athena. It's just their assistant that we've recruited, trained, matched, and then increasingly will superpower with AI so we can work in lots of different verticals and situations. Now you have to be certified for all the health stuff. We can't do that for you. But assuming you are then our Athena assistant and can roll in behind what you already have in place, I can.
Jason Calacanis
Give an example of this. Because we are international, we have international partners. Had to lock down all of our data. I have operations not in the United, just in the United States, but I also have operations in the Middle east and Japan. Each of these countries has different privacy regulations. So I needed to lock down all of our computers. It's a little draconian. Some people are like, oh my God, spyware on a computer. It's like, hey, we work at a finance company. This is just table stakes. We have to travel around the world. Our Athena assistants have to be in our notion, they have to be in our Grammarly, our Slack, our superhuman. So they also have to. So I talked to Jonathan. I think we sent our own laptops or you gave them laptops. And then we put our software on it. We locked down their computers because they have, they have access. We can't have somebody submit a business plan to us or their financials or legal documents. We need to review and sign and then have them get hacked. And if they do get hacked, God forbid, we need to have a way to trace that and figure out how big the hack was, etc. So you guys were able to accommodate our stack?
Jonathan Swanson
Yeah, we purchase and deploy the laptop so that we can install security and controls and mobile device management and all the normal things you would, you'd expect so that you can be in control.
Jason Calacanis
Oh, right, you have your own concerns about that, right? You have to make sure that your Athena assistants are tight.
Jonathan Swanson
And this is why we set up real entity. People come in for interviews, we have driver's license and we're on the ground. And you know, when someone asks me, could something go wrong, like, look, if you hire an assistant in San Francisco, could something go wrong? Of course. So you need to use, you know, practical precautions. But if someone in San Francisco does something wrong, they face the full force of the law and they're deterred from doing that. We select the right humans, but we also do things the right way. So the incentives are right. So, so that everyone's protected.
Jason Calacanis
When we were doing Mahalo back in the day and I was building a human powered search engine backed by Sequoia and Ruloff was my backer here. And it didn't work out. We were too early. And we also had Google search problems. But one of the things we experimented with was in the Philippines hiring people to help us build out these search pages, like Wikipedia pages and comprehensive search. And we had this firm that we were experimenting with. We had 20 people on duty and they were telling us, this is what we pay the folks and this is our cut, right? So we had this arrangement because we are wearing boots on the ground. We actually wound up sending Mike Rhodes, one of the great employees I had there, to Manila to do training and shout out to Mike Rhodes. But that was after we had this problem, Jonathan, some of the people on the team, because I had mentioned, I think on this very podcast that I was what I was paying them and how great this, like, was said, we're not actually getting paid that amount. We're getting paid like a third of that amount. And I was like, what? And we go to the person, the person like, oh, no, no, it's a misunderstanding. We had these training people anyway. They were lying to us. They were being dishonest. We didn't have boots on the ground. We sent boots on the ground. You know, da, da, da. We wanted them in an office. We wanted to know their names. So then we said, okay. We came with this great system. They would send us pay slips. Three months later, same complaint, we get the pay slips, they were doctored. The person sent us their pays. Yes, it turns out that's crazy. It's not crazy when you're dealing with an emerging frontier world, which Mr. President, Donald Trump, even Jason, he recognizes, even Jason has these insights. He calls it the Third world. I call it frontier markets. I use the proper language. But listen, President Trump can use what he wants, okay, Precise language. In these markets. It's a little bit of the Wild West. So, like, there's the United States, there's like banana republics, and then the Philippines or India, they might be somewhere. But they call them the emerging markets or frontier markets for the reason you have to deal with this. And that's why Jonathan, actually having a partner like Jonathan and Athena makes a lot of sense. Because I don't want to deal with this stuff. I had to deal with that stuff.
Jonathan Swanson
Look, what I tell, I tell founders is I want every founder have an assistant. You don't have to use me if you don't have any budget, use ChatGPT and use it as your partner. Brainstorm, help you set goals. If you have budget for $5 an hour and that's all, then go on to upwork and one of these services and hire yourself. With the caveat that you need to interview hundreds of people and have lots of precautions for all the reasons you just said. Jason. Yes, that's always an option when you know, I hired the very first person in the Philippines off upwork at the time and interviewed a couple hundred people and you have to interview a lot like athena. We vet 400 people for everyone we hire. Wow. So if you're interviewing 10, you're probably not going to get that gym. But you can do that on your own. If you don't have budget, like I want you to do that, don't use Athena. But if you can afford $3,000 a month, then don't take the brain damage.
Jason Calacanis
Athena wow.com VIP is my VIP link going to keep it up for a little bit? Instead of getting two weeks free, you get four. It's the best deal in the world. And like I said, you get what you put in. If you're not willing to delegate and like put work into it, please don't do it. If you're on a budget, please don't do it. Go do upwork, find websites five or whatever you want. But this is the secret behind my productivity is my dual Athena 365 day coverage. Man, it is incredible for me, listen, I do my Tahoe trip. I don't want to say this because I got to gatekeep it, but it's hard when you go certain time periods. When I go to Niseco for skiing, it's hard to get reservations. So what do I do? Six weeks out, I set up my reservations for the week I'm planning on going. When I go to Tahoe, same thing. I booked these restaurants six weeks out. They know who I am. My feed assistants take time on the phone. I have a little script, yada yada. It's Jason Calcanis. It's coming in. You want to make your life easy as a founder and reclaim your energy. Jonathan, it is such a privilege and honor for me to be the first investor in two extraordinary unicorns that you and your partners, Marco and the teams have built.
Jonathan Swanson
Thank you for being first. We couldn't do without you. You've been amazing and excited to.
Jason Calacanis
Let's tell the truth. You could have done it without me and you would have done it without me. Maybe not the first one. It May have been harder with the first one, I'll give you that.
Jonathan Swanson
I don't know if that round would have been catalyzed. I mean, look, we wouldn't have given up, I tell you that. But we had been trying and you helped catalyze it. So I'm gonna give you credit on this one, okay?
Jason Calacanis
I take credit for the first, take no credit for the second. I like it. I'll split the difference with you. It's just great to know you. For those of you who are Founders out there, if you want to have the relationship Jonathan and I have had for a decade, it's very simple. Go to Founder University in Japan, Saudi or America. The sun never sets on the JCAL empire. I'm operating in three different time zones around the world now. Jonathan, I am scaling thanks to my Athena assistance. I love you, brother.
Jonathan Swanson
Love you. Thank you so much. Appreciate the support.
Jason Calacanis
We'll see you all next time. Come to Founder University. Why don't you come? Okay. Oh, no. Yeah, you should come and talk. You're gonna give a talk? That's why I'm gonna get your time now.
Jonathan Swanson
You Japan sounds fun. I love Japan.
Jason Calacanis
Second week in January. You could come be a mentor and then we could go hit this juice ski or not.
Jonathan Swanson
I do. I was actually on the ski team growing up. Slalom team. That is not far from Philippines.
Jason Calacanis
Let's talk about it could be a one, two punch. All right, everybody, we'll see you next time. Bye bye.
Host: Jason Calacanis
Guests: Jonathan Swanson (Athena, Thumbtack), Alex Wilhelm
Date: December 4, 2025
Episode Theme:
Exploring the transformative power of delegation, the evolution of executive assistance, and building scalable processes for founders and startups. Jonathan Swanson shares his journey from co-founding Thumbtack to starting Athena, a company aiming to give leaders “the most valuable asset—time.” The discussion covers lessons on delegation, the intersection of human and AI-powered assistance, and actionable strategies for founders.
Jonathan Swanson’s Thumbtack Journey
“You catalyzed the whole round. JCAL first investor in. … Now it's doing around half a billion of revenue, very profitable, growing nicely.” — Jonathan Swanson [02:19]
“At that time, the angels there were like maybe a dozen in each of the major cities … It was really hard to figure out who they were, but they were charging founders $5,000…” — Jason Calacanis [02:52]
Importance of Early Product Thoughts
“Adding that extra touch can add some magic to the experience.” — Jason Calacanis [06:53]
Office Stories & Growth Pains
“Having an investor like that select you … it just raises your ambitions. You're like, let's not go for 100 million in revenue, let's go for 10 billion.” — Jonathan Swanson [08:45]
Origin Story & Inspiration
“What if I had a team of assistants like the President has? … She [first assistant] really transformed what I was capable of doing … helped me make friends, helped me meet my wife.” — Jonathan Swanson [00:00, 11:05]
How Athena Works
Who Should Use an Assistant & How
“Everyone should start with one. … First assistant takes the pain away—passport renewals, scheduling, inbox.” — Jonathan Swanson [12:53]
“I only achieved [time abundance] when I had a chief of staff and six. … There is someone handling every part of my life.” — Jonathan Swanson [12:53]
Cost and Value Proposition
“Previously in the Valley, an EA is 100 to $150,000 a year … Athena trains them. Athena matches them… If it’s not a fit, they replace them.” — Jason Calacanis [14:23]
High Leverage Delegation
“When you're not delegating, you're actually withholding a good paying job to someone in the developing world…” — Jonathan Swanson [18:32]
Will AI Replace Human Assistants?
“Humans are good UX … but behind the human, there are machine assistants we’re building that will automate more and more. … Like Tesla: progressive automation, always a ‘steering wheel’ for some time.” — Jonathan Swanson [21:14]
Training & Selection
“I got word from our partner at OpenAI … they said Athena was the fastest ramp of any enterprise they’ve worked with and the highest utilization per employee.” — Jonathan Swanson [25:42]
Company Growth
“We’ve exceeded $100 million run rate. … Expect to continue that growth into next year.” — Jonathan Swanson [26:27]
Expanding Global Supply
“Traffic has gone to zero. … Google thought that we had done something inappropriate … the Google death penalty … not that you’re deranked, you don’t exist.” — Jonathan Swanson [29:15]
“You just lock arms and you’re like, we’re gonna do it.” — Jonathan Swanson [30:21]
Maximizing Value from Assistants
“It took me 10 seconds to come up with… going through my dad's Facebook to ask for memories; going to take my assistant six weeks to execute.” — Jonathan Swanson [33:55]
Measuring ROI & The Importance of Process
“Checklists really reduce mistakes … If you make a checklist for your Athena assistants … chances of you making a mistake in highly repetitive tasks goes down in a massive way.” — Jason Calacanis [44:39]
Defining Product-Market Fit
“You have product market fit when it feels like the market has you by the nostrils and it's just pulling you.” — Jonathan Swanson [37:55]
Qualities of Ideal Customers
Enterprise-Grade Security
Market Comparisons
“We vet 400 people for everyone we hire.” — Jonathan Swanson [54:04]
On Time:
“The most valuable asset in the world. It’s not gold or bitcoin or Nvidia clusters. It’s time.” — Jonathan Swanson [11:05]
Delegation as Leverage:
“If you don’t have an assistant, you ARE the assistant.” — Jonathan Swanson [12:53]
On Finding Product/Market Fit:
“You have product market fit when it feels like the market has you by the nostrils and it’s just pulling you.” — Jonathan Swanson [37:55]
On Overcoming Crisis:
“Traffic has gone to zero. … Google death penalty … you just lock arms and you’re like, we’re gonna do it.” — Jonathan Swanson [29:15-30:21]
On Delegation Guilt:
“When you’re not delegating, you’re actually withholding a good paying job to someone in the developing world who desperately wants it.” — Jonathan Swanson [18:32]
On AI’s Role:
“Humans are good UX … The client's in front, but behind the human, there are machine assistants we're building.” — Jonathan Swanson [21:14]
On Process:
“Checklists really reduce mistakes … for your Athena assistants … the chances of you making a mistake in highly repetitive tasks goes down in a massive way.” — Jason Calacanis [44:39]
Memorable Closing Exchange
Jason: "I love you, brother."
Jonathan: "Love you. Thank you so much. Appreciate the support."
[56:46]
If you want to reclaim your time and do more of what matters, consider how delegation—and the systems to support it—can unlock your next level. Whether through Athena or your own methods, the essential lesson is: You get what you put in.
Listen to the full episode for additional practical stories, advanced tips, and the full measure of this high-energy conversation.