Episode Summary
Executive Summary: Jason Calacanis interviews Jonathan Swanson, founder of Thumbtack and Athena. Swanson recounts his journey from Thumbtack's early days (now ~$500M revenue, profitable) to launching Athena, a service that provides trained, remote human assistants (augmented by AI) to executives and founders. Athena addresses the pain of finding and retaining quality assistants by hiring full-time employees in countries like the Philippines, Kenya, and Guatemala, training them at in-person centers, and matching them with clients for $3,000/month. The company has scaled to a $100M+ run rate, is 100% referral-driven, and emphasizes that delegation is a skill clients must invest in. Swanson shares personal stories of how assistants helped him make friends, meet his wife, and achieve 'time abundance,' and discusses the future blend of human and AI assistance.
Main Topics: The Thumbtack Journey & Origin Story: Swanson's background from White House to Thumbtack, meeting Calacanis, and the early days of Open Angel Forum. Thumbtack's evolution from directory to booking engine, and its current success. The Problem Athena Solves: Time Scarcity & the EA Gap: Discussion of time as the ultimate resource, the problem with traditional in-person EAs (high cost, low retention, reluctance to delegate), and the Athena solution: trained, remote, full-time assistants. Human + AI: The Future of Assistance: How AI will enhance human assistants but not replace them, using the Tesla/self-driving analogy. Athena's partnership with OpenAI and plans to build an internal AI workflow tool that could become a standalone product. The Art of Delegation & Getting the Most from Your Assistant: Advice on how to delegate effectively: start with tasks you dislike, build checklists, provide constant feedback, and invest in the assistant-client relationship. The concept of achieving 'time abundance' with multiple assistants. Athena's Business Model, Scale & Operations: Athena's hiring process (50k applications/month, 400:1 vetting), in-person training centers (Athena Academy with accredited MBA program), full employment model, and its growth from $40M to $100M+ run rate. Startup Crisis: The Google Death Penalty: Story of Thumbtack being hit by a Google penalty that set traffic to zero, and Swanson's advice on recognizing product-market fit (when customers market for you). Creative & Personal Use Cases for an Assistant: Creative uses: baby monitoring, dinner party planning, gift book creation, grit-building activities with kids. Emphasizing that assistants can help with personal goals, not just work.
Key Arguments: Time is the most valuable asset, and outsourcing tasks to skilled assistants is the best way to reclaim it. Most founders fail to delegate effectively because they lack a system or feel guilt; they must invest in learning to delegate and build checklists. A remote assistant model, using full-time employees in developing countries with proper training and legal structures, can provide higher quality and retention than in-person EAs in Silicon Valley. AI should augment human assistants (like lane assist) rather than replace them; the human remains the UX, and AI boosts their capabilities. Assistants should be a founder's first hire; if cash is tight, even using ChatGPT as an assistant is better than having none. Athena's 100% referral growth and high demand demonstrate product-market fit; clients must be willing to invest in the relationship for it to work.
Data Points: Thumbtack revenue: around half a billion - Thumbtack's current business metrics shared by Jonathan Swanson Athena run rate at investment: about 40 million - Athena's bootstrapped revenue run rate at the time of Jason's investment Athena run rate now: exceeding 100 million - Athena's current revenue run rate Assistant applications per month: 50,000 - Athena's monthly assistant applications Vetting ratio (applicants per hire): 400 to 1 - Athena's vetting ratio Max new assistants per month: 500 - Athena's maximum new assistant output per month at current capacity Growth source: 100% referral-driven - Athena's growth driver Monthly cost per assistant: $3,000 - Cost of an Athena assistant Annual cost per assistant: $36,000 - Annual cost of an Athena assistant Typical in-person EA salary in Silicon Valley: $100,000 - $150,000 per year - Comparison to in-person EA costs in the Valley Private kindergarten cost in SF: $36,000 per year - Comparison to San Francisco private kindergarten tuition Sales disqualification rate: 10-15% - Customer disqualification rate by sales team Traffic from Google after penalty: zero - Thumbtack's close call: Google traffic dropped to zero Signups in first 24 hours: 1,000 - Athena's first-day signups upon launch Jonathan's personal assistants: 6 (1 chief of staff + 5 specialists) - Number of Athena assistants Jonathan Swanson uses personally Fastest OpenAI enterprise ramp: Athena had the fastest ramp and highest utilization per employee - OpenAI's assessment of Athena's AI adoption Swanson's children: 4 - Number of kids in Swanson's family using the night-watch system
Pivotal Quotes: "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." — Jonathan Swanson: Swanson explains the value of time as a non-renewable resource and Athena's core mission. "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: Swanson reframes the guilt of delegating as providing opportunity to someone in the developing world. "My definition of product market fit is your customers market for you because they love it so much." — Jonathan Swanson: Swanson and Calacanis discuss the indicator of true product-market fit. "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." — Jason Calacanis: Calacanis reflects on the long-term partnership with Swanson, from Thumbtack to Athena.
Implications: Athena's model demonstrates a scalable, high-quality alternative to in-person EAs, making executive-level support accessible to more founders. The human-plus-AI approach suggests a future where remote, trained support teams become a standard productivity multiplier for knowledge workers, potentially reshaping how startups and executives operate.
From the Episode
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 be 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 of 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. Crusoe Cloud. Crusoe is the AI factory company, reliable infrastructure and expert support. Visit cruso.ai/slash build to reserve your capacity for the latest GPUs today. And Northwest registers.
But the extra effort you put to delegate that first time then trains 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 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
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, and 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, Wellfront, 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. 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,
About This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.