Getting past the “Cardinal Sins of Delegating” with Jonathan Swanson of Athena | E2218

4 Dec 2025 · 57 min

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This Week in Startups - Episode Summary

Episode Title

Getting past the “Cardinal Sins of Delegating” with Jonathan Swanson of Athena | E2218

Description In this episode, Jason Calacanis interviews Jonathan Swanson, founder of Athena, a service that trains online assistants and pairs them with busy executives and founders. The discussion revolves around effective delegation, the challenges of hiring assistants, and insights from their shared entrepreneurial journeys.

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Key Takeaways

  1. The Importance of Delegation
  2. Delegating tasks is a skill that requires training and commitment.
  3. Jonathan emphasizes the transformation that delegating can bring, referencing his own experience with assistants.
  1. Introduction to Jonathan Swanson & Athena
  2. Jonathan Swanson shares his background, including his early experience at the White House and how it influenced his high standards for executive assistants (EAs).
  3. Athena's mission: To provide people with more time, the most valuable resource, by matching them with trained human assistants.
  1. Managing Multiple Assistants
  2. Jonathan discusses his experience managing six assistants, with each focusing on different aspects of his professional life.
  3. He advises starting with one assistant, emphasizing the cognitive load reduction it brings.
  1. Cardinal Sins of Delegation
  2. The episode explores common mistakes in delegation:
  3. Control Issues: Founders often believe it’s faster to do things themselves initially.
  4. Guilt: Founders feel guilty about delegating tasks to others, not realizing it provides valuable jobs.
  1. The Value of Time
  2. Time is portrayed as the most precious resource one can have.
  3. Jonathan argues that effective delegation allows founders to focus on what truly matters.
  1. Market Pull and Product-Market Fit
  2. Jonathan describes what market pull feels like for a startup, sharing the explosive growth Athena experienced upon launch.
  3. He defines product-market fit as conditions where customers advocate for your product because they love it.
  1. Training and Integrating Assistants
  2. Athena's unique training program, led by experienced educators, ensures assistants are well-prepared.
  3. The integration process allows assistants to seamlessly fit into a client’s existing workflows.
  1. AI and Human Assistance
  2. Discussion on the role of AI in enhancing the capabilities of human assistants.
  3. Jonathan believes that while AI will assist, the human touch remains critical to effective service.
  1. Challenges and Growth
  2. The conversation touches on the challenges of scaling a startup, with Jonathan sharing anecdotes from his previous venture, Thumbtack.
  3. Athena's growth trajectory, including surpassing a $100 million run rate, is highlighted.
  1. Building Relationships and Systems
  2. The episode concludes with a focus on the necessity of building relationships and systematic approaches to delegation to maximize productivity.

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Additional Insights

  • Investment in Training: Athena has invested in training for assistants, creating educational opportunities that benefit both the assistant and the clients.
  • Real-World Applications: Examples shared about personalized services, such as planning personal events and managing schedules, showcase the depth of assistance provided by Athena.
  • Cultural Sensitivity: The importance of understanding cultural dynamics when hiring assistants from different countries is emphasized.

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Conclusion This episode provides valuable insights into the art of delegation and the transformative power of effective assistantship, highlighting the experiences and lessons learned by both Jason Calacanis and Jonathan Swanson. It emphasizes the significant impact of managing time effectively through delegation, the importance of training, and the role of technology in modern assistance.

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Transcript

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0:00I never had assistants or service providers or house cleaners in my house, 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.

0:37She 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, spend time with their family, whatever matters most to them. 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 three months free at gusto.com slash twist.

1:15Crusoe Cloud. Crusoe is the AI factory company, reliable infrastructure and expert support. Visit crusoe.ai slash build 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 slash twist today. Hey everybody, welcome back to This Week in Starbs. I'm your host, Jason Calacanis.

1:56With 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. That's right. 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 of months and you catalyzed the whole round, JCal first investor in.

2:38And 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. Amazing. It's really interesting what small acts can do in your life. 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, angels, there were 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.

3:15And 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. Oh, that's right. It was pay to play back in the day. Yeah, it wasn't just that there weren't many. The founders had to pay to pitch. It was bonkers. And you probably got pitched on this. Yeah, Jonathan? 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. 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 tell us your idea.

3:57And 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 don't you need to pay me? It's just burgers and beers. We'll 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.

4:25Fill 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. I mean, when we started Thumbtack, it was Amazon sells products. Where do I hire? Hanuman, 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 the reviews and prices and all that. So you can go from idea to actually hiring a pro as quickly as possible.

5:02Incredible, really simple idea. I remember a lot of those early investments, Jonathan, they inform what I do when we have scaled the firm to 100 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 and 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.

5:44It 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. And you might do something stupid like, Oh, the gate code's 1234. 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.

6:17Maybe talk a little bit about that and then we'll get into Athena. 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 a hundred 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 that 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 it was like 12 of us.

6:48And you said this exact same thing. You're like, I'm just been playing with the path app. I remember this. Oh, yeah. And you're like, path had these delightful little interactions. when you push things, it 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. I remember that really shitty office you had. And it was like a dumpy kitchen. And we were in the kitchen at like two awkwardly sized tables that didn't balance properly. It was proper startup. Proper startup. Between 6th and 5th, which is between kind of nice square area at the time.

7:26and then the end of civilization. Yes, exactly. Someone does have a lot of those fault lines. How long were you in the tiny office, Jonathan? Starting a house. We were housed 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. We were in that office for a few more years. And then five, six years in, we moved to a proper office that was fun to invite friends to. And really interestingly, it was one of my first five Sequoia Scout investments. I'm here at Sequoia today where Ruloff created the Scouts program, both of them.

7:59And 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. 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 been 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 an investor at that caliber because they really raise your aspirations and your ambitions significantly.

8:40I unpack that. How so? What was your experience directly with rule off the team at Sequoia, whatever, in terms of expanding? 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 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.

9:15But 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 not go for a hundred million revenue. Let's go for 10 billion and 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 got to build something that lasts for generations. And they do a good job of really hyping up that potential. Being a founder is a lot of work.

9:50You have to focus on your fundraising. Then you got to 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?

10:30Then 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 you a great domain name. So here's your call to action. Go to Northwest, registeredagent.com slash 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. You said, hey, can we get something to eat? Jonathan, you know, you were the first investor in Thumbdeck. I 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.

11:05Just to give a little background on it. I grew up in the Midwest, Midwest boy, parents were farmers. I never had assistants or service providers or house cleaners in my house, 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 an 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?

11:44Not 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, help me meet 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.

12:20It'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, 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. 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 next assistant you add to your team?

12:53I've never start with six. Everyone should start with one. What I say is if you don't have an assistant, you are the assistant. So start with one. It 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 the 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.

13:25And 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 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. A 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.

14:03I have time to dream big and think about what's next. So for my team, Chief of Stats sits on top and then each EA specializes. I have one that focuses on finance, P &L, angel investments. I presume the average Athena customer, though, has one probably is probably the medium. Yeah, most people start with one and then they add a second or a third. Oh, wow. Co-founder gets one. 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.

14:37In the Valley, an EA is$100 ,000 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, as 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. It then has people throw up their hands and say, I'm not going to have an EA, which is what most founders do.

15:12And this is why when you pitched 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 he got lucky the first time. I need that lucky J-Cal 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. I was meeting an octopus and said, 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.

15:45Yes, 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 EA. Two is 75K or 72K. But you remove all the recruiting and training part. You do get what you put out. They're not in person, so they're not getting coffee for the person. So you're not getting that. But it turns out 99 % or 95 % fully can be done remote. And maybe one day we'll have Assistant Contella operate a robot in your home.

16:22We were joking about this, but we're like, actually, maybe in the next few years, that's possible. Three, probably. Well, 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.

16:55And 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 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.

17:32People know that I talk about it. When I went to Mexico City recently, I said, here are my subscriptions, monocle.com, Condé Nast 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, 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 730 reservation. Book it. Research it from these places. Rank it. Tell me which ones have Michelin stars.

18:02Tell 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 it. You just show up whenever you want. You miss the ones you don't. 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... And if you had asked, they would have just said no. Yeah, they would have been like, I'll get you one, but why? They would have questioned it. I think this is a key unlock for lots of people.

18:34The 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.

19:24And 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 learn. Yeah, I think lots of people have to reframe that to have the confidence to lean into delegation. 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.

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20:37Pending availability, Okay, that's C-R-U-S-O-E dot AI slash build to apply and get those hundred thousand dollars in credits. 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 a little bit. 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 three Athena assistants in five years if AI continues to improve as it does?

21:14It's a natural question. It's 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. 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.

21:44And 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. So where are we on the path from lane assist to full self-driving in terms of bringing AI into the assistant principal relationship? We're day one. We're the lane assist. Humans are predominant and the machines are now starting in Q1 of this next year. I think 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.

22:21And 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. 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.

23:02They are AI first. I don't know if this is part of the training program, but I told them get the comment 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, condenestraveler.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 started on second base with their research. They weren't manually researching.

23:36So maybe you could talk about how do you train Athena assistants and select them? Both of those things seem to be kind of important. 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.

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24:12So 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. me. We've actually got it accredited.

24:45So 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.

25:23So 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. Is that a piece of software you might break off later and sell as a standalone entity? 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.

25:56We think the only way to build this is with a human that live 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. 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. I think it 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. We have a good story about this growth.

26:27When J. Cal and I met for lunch at the Greek restaurant, I bootstrapped the business to that point with my own capital. And I asked J. Cal, will you be my first investor? And he said yes on the spot, which made me love him again. And we're 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.

27:02We 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 athenawow.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, would that be able to kind of move the needle? Well, sure enough, when I mentioned it on All In, my bestie Chamath was like, tell me about this Athena thing.

27:34I need an assistant. He was going through the same pain and suffering I was, which was, I can't, like just 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. We had a wait list for many, many months because of this.

28:07I was basically like, most of us are happy. The supply team is crying because of 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. And 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. And so - How many a month, Jonathan? How many new assistants can you get through Athena Academy and kind of onto the system per month or quarter right now?

28:39So 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. I think it's smart. 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, Jonathan. Of course. 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 Thumbtack's history that you probably know about.

29:13Permission granted. Tell us the story. 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. Uh-oh. 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.

29:45And this is kind of the madness of a startup life is I've got 30 new employees who I'm doing a new employee onboarding with. I'm telling them about the history of the company. And then 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 a 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. Just fully unpersoned. Wow. Excommunicated, yes. You're no longer recognized by the gods.

30:19Exactly. It's like a black site. Yeah. 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 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 going to do it. And then when you come out, you take a little breather.

30:51and you're like, that was insane. Let's not do it again, but it was actually kind of a fun experience. 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 got to 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.

31:23No, 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 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.

31:55We 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-E. That's my favorite price, folks. Go to gusto.com slash twist. That's Gusto, G-U-S-T-O.com slash 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, J. Cal, you don't need people on Saturday and Sunday. I said, I have a plan. Number one, I can afford it.

32:26I can afford to build out this infrastructure 365 days a year. So I'm going to try. Athena was like, OK, 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 J. Cal said about Apple over the years on CNBC? And they can pull it up. I never had that ability.

32:58But they also empowered 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 I do, 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 talk to them. That's a backstop for Ricky and I and for the sales team to know if we're missing. And I don't want highly paid salespeople, six-figure people listening to other podcasts and timestamping and doing that work.

33:35This 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. You say, of course, I didn't figure this out for six months. 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 and 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.

34:16You'll make a bunch of friends. You want to give a good gift to your dad? I have an assistant today. I hope my dad's not listening. Going through his entire Facebook account and DMing every friend, asking for a 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 gonna take my assistant six weeks to execute the project it's a huge project but it's gonna be one of the most meaningful gifts i'm ever able to give incredible to me that's 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 oh my god so they could go interview people get that video save it clip it and just have it prepped for a videographer or documentarian.

35:09Oh my God, it's so genius. I mean, the possibilities are endless. 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.

35:40But there are some that are hard for the first two days, like skiing, golf, rock climbing, pickleball. You got to 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 it really worked out. They did all that for me. They coordinated it all. They gave me four choices for each one.

36:09And 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 too hard to do. Nobody wanted to do it. But then we found eventually other activities. Another way to say it is it would not have happened without the Athena assistant. So it sounds like you can either have an Athena assistant for your family, say, that does all this amazing stuff for you, or you could have one child in private kindergarten because they're about the same cost now. If you look at$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.

36:48I think that's like one of the things. And you can experiment with it, yeah? 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 find ways to save money. Wait 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 it makes it even easier. When you look at your 10 plus years building startups, and we had a great question come in from the audience about product market fit, TechnoChief2000, 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.

37:36TechnoChief 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 bangs that occur. So tell me about your experience with that. You know, 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. It's uncomfortable. At Athena, the first time I experienced that, we launched the service and I didn't know how much demand there was going to be.

38:14and 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 product market fit. And now it's possible to build big businesses that require huge sales teams and lots of ad spending.

38:52And that can be, you can build billion dollar businesses that way. But my definition of product market fit is your customers market for you because they love it so much. Jason, good definition? 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 two Athena assistants. 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.

39:31And 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 a founder of 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.

39:59So you're fine tuning. Don't sell Athena assistance 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. It's a great point. 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.

40:32You have to give your 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 over 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. What percent of potential customers fail that test and you tell them essentially, this is not going to be for you? Well, we tell people on the way in. So lots of people just don't sign up.

41:03And then the sales team probably disqualifies 10 to 15 percent who just don't feel like they're going to put the effort in. Raul over at Superhuman, who when I was doing Open Angel for him, I did Reportive. 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 there 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 both sides of the table.

41:34If people 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 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. Our first learning when we started this business was we'll recruit and train the assistants and then we'll match them.

42:00And 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 delegate 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, OK, 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.

42:34Think 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 really the key to getting to the next level. 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, it 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.

43:10I'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 started putting my communication to you in chat. I said, please don't do that. I would rather have like a mistake in your grammar. You fix the grammar, but don't have it give me a sentence. And it's like, if you have time between these two meetings, you can use it to catch up.

43:42I 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 crisp bullet points. I want to train my Athena assistant to do it the way I want to do it. Yada, yada, yada. 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.

44:18But it's actually a partnership. It's not that the assistant's the best, it's that the combination is the best. And so when someone feels like their assistant's not right, we first investigate the assistant 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 get more leverage out of this person. 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 in, 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.

44:58And it turns out like checklists really reduce mistakes. We had a mistake today with a company we were syndicating and we skipped the part of the checklist. And it's like, you know, if you make a checklist for your Athena assistants, for your researchers, analysts, yourself, the chances of you making a mistake in highly repetitive tasks goes down in a massive way. 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.

45:31I 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 OK, I want six to eight people there. I want them to have just raise capital. Companies like Uber, Airbnb, who were, you know, at the time, just tiny little startups. Invite the founders. Here's the message. Get a chef off of Thumbtack.

45:59and I want to walk home from work at 8 p.m., walk into my apartment and there'll 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 can 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 the checklist. Sounds simple, but it can become something bigger.

46:28You 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. This is black diamond delegating. I'd like to clarify. Okay. Black diamond, double black diamond or black diamond? Feels like double black. I do raise my children. I don't delegate the raising and loving of my children. There are certain lines. This is 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 can actually calm the situation down and we don't have to be called.

47:27But of course, if we're called, we go in and we help our kiddos. 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, hey, there's people around the globe who are looking for work. And this is work you're probably not going to get an American to do, especially now when we have 4 % unemployment. I mean, everybody wants to argue about this, but we still don't have a lot of people. So here's this security camera.

47:55If 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 a person in the black hoodie. Now, 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, 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.

48:27It's like a boring job to look at eight monitors. Yeah, you can have one human watching multiple houses. Eventually, you can have machines watching. And so you have machines plus humans 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 this literally happened, a new gardener was sent. I got an alert. Oh, new gardener. Great. Yeah. You create lots of, prevent lots of dangerous situations with my night watch situation with our kiddos.

49:03Like we've had times where one of the kids was climbing out of the crib and about to fall to the ground. It was the first time they'd ever been able to climb. And we wouldn't have known about it until we found them, you know, crying. But instead the The night nurse called us and we ran over and grabbed them. And having that human in the loop is pretty cool. So genius. Here's a question from one of our nodies. The nodies, just so you know, Jonathan, are my true, true fans. They are the notification gang. So we call them Nody Gang, N-O-T-I, because they have the notifications turned on. And they're the first to come to the live feed.

49:37So Nody 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 Pilgs. Yeah, great question. 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 systems or security or rules that they have to follow, you treat them like any other employee. And for most of our clients, most of the company doesn't even know this assistant is necessarily from Athena.

50:14They'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 can roll in behind what you already have in place. I can 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 just in the United States, but I also have operations in the Middle East and Japan.

50:46Each 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 our computers. 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, so you gave them laptops, and then we put our software on it. We lock down their computers because 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.

51:23And if they do get hacked, God forbid, we need to have a way to trace that and figure out how big the hack was, et cetera. So you guys were able to accommodate our stack, 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'd expect so that you can be in control. Oh, right. You have your own concerns about that, right? You have to make sure that your Athena assistants are tight. And this is why we set up real entities. People come in for interviews. We have driver's license and we're on the ground. And when someone asks me, could something go wrong?

51:58I'm like, look, if you hire an assistant in San Francisco, could something go wrong? Of course. So you need to use 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 that everyone is protected. When we were doing Mahalo back in the day, I was building a human-powered search engine backed by Sequoia. And Rulof was my backer here. And it didn't work out. we were too early and we also had Google search problems.

52:27But one of the things we experimented with was in the Philippines, hiring people to help us build out these search pages, 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 were in 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.

53:02We're getting paid like a third of that amount. And I was like, what? And we go to the person, the person's 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, dah, dah, dah, dah. We wanted them in an office. We wanted to know their names. So then we said, okay, we came up 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 It turns out - That's crazy.

53:23It'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, and they call them the emerging markets or frontier markets for the reason. You have to deal with this.

53:57And 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. Look, what I tell founders is I want every founder to 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.

54:29Yes, that's always an option when you know, I hired the very first person in the Philippines off work at the time and interviewed a couple hundred people and you have to interview a lot like a Athena we've at 400 people for everyone we hire. Wow, you're interviewing 10. You're probably not going to get that gem 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. AthenaWow.com slash VIP is my VIP link. I'm going to keep it up for a little bit. Instead of getting two weeks free, you get four.

54:59It'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 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 Niseko 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.

55:36When I go to Tahoe, same thing. I book these restaurants six weeks out. They know who I am. My Athena assistants take time on the phone. want to have a little script, yada, yada, it's Jason Calcannon, 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. Thank you for being first. We couldn't do it without you. You've been amazing and excited to - Let's tell the truth. You could have done it without me and you would have done it without me.

56:08Maybe not the first one. It may have been harder with the first one. I'll 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 going to give you credit on this one. Okay, I take credit for the first, take no credit for the second. I like it. I'll split the difference with you, which is 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 J-Cal empire.

56:38I'm operating in three different time zones around the world now, Jonathan. I am scaling thanks to my Athena assistance. I love you, brother. Love you. Thank you so much. Appreciate the support. We'll see you all next time. Come to Founder.University. Why don't you come? Okay, we'll talk to you soon. Oh, no, yeah, you should come and talk. You're going to give a talk. That's why I'm going to get your time. Japan sounds fun. I love Japan. Second week in January, you could come be a mentor and then we could go hit the, do you ski or not? I do. I was actually on the ski team growing up, slalom team.

57:05It is not far from Philippines. Let's talk about it. Could be a one-two punch. All right, everybody. We'll see you next time. Bye-bye.

From the publisher

This Week In Startups is made possible by:

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Today’s show:

Delegating is its own unique skill, requiring training and a real investment of time and attention.

On TWiST, Jason chats for a full hour with the founder of one of his favorite startups, Athena, which trains online assistants and pairs them with busy founders and executives. (Jason has 2!)

But getting the MOST out of your executive assistants is less obvious than it looks. Jonathan unpacks some of the secrets to “Black Diamond Delegating,” and how he manages to keep 6 different high-level helpers operating at once.

Plus, Jason and Jonathan look back at the Open Angel Forum days, where Jason invested in Jonathan’s previous company, Thumbtack, praise the “Checklist Manifesto,” discuss the telltale signs you’ve achieved market pull, and lots more insights.

Timestamps:

(01:53) We’re joined by Jonathan Swanson from one of JCal’s fav startups, Athena!(02:02) Jason and Jonathan first met during the Open Angel Forum, when Jonathan was working on Thumbtack(06:44) Finding the “little touches” that can help make an app more delightful(9:47) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(12:05) The shift from Thumbtack to Athena was all about time(12:52) How Jonathan delegates to 6 exec assistants at once(14:22) Pricing Athena’s EAs: Jason runs the numbers(15:09) Why Athena made Jason believe in hiring assistants again(18:15) Getting past the “Cardinal Sins of Delegation”(19:38) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.(20:48) Will AI ever be able to replace Athena assistants?(23:41) Inside how Athena finds and trains assistants from around the world(27:01) How JCal became an Athena Ambassador… and almost crashed the system!(30:55) Gusto - Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at https://www.gusto.com/twist(32:11) The magic of having assistants work on “backstop projects” and creative tasks(37:14) How to know when you have achieved market pull(40:05) Why getting the most out of delegating takes real investment and training(44:36) More praise for the Checklist Manifesto(46:26) Jonathan gives us a peek at what “Black Diamond Delegation” looks like(52:14) Jason’s early experiences hiring overseas assistants, from the Mahalo days*Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.comCheck out the TWIST500: https://twist500.comSubscribe to This Week in Startups on Apple: https://rb.gy/v19fcp*Follow Lon:X: https://x.com/lons*Follow Alex:X: https://x.com/alexLinkedIn: https://www.linkedin.com/in/alexwilhelm/*Follow Jason:X: https://twitter.com/JasonLinkedIn: https://www.linkedin.com/in/jasoncalacanis/*Thank you to our partners:(9:47) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today!(19:38) Crusoe Cloud: Crusoe is the AI factory company. Reliable infrastructure and expert support. Visit https://crusoe.ai/build to reserve your capacity for the latest GPUs today.(30:55) Gusto - Check out the online payroll and benefits experts with software built specifically for small business and startups. Try Gusto today and get three months FREE at https://www.gusto.com/twist

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