Meet the Slowest Startup Incubator in the World—Pumping Out Billion-dollar Companies episode artwork

EPISODE · Mar 4, 2026 · 45 MIN

Meet the Slowest Startup Incubator in the World—Pumping Out Billion-dollar Companies

from AI and I · host Dan Shipper

Silicon Valley loves billion-dollar moonshots and AI darlings. Sam Gerstenzang and Dan Friedman are doing something different—they're starting medical spas and funeral homes.On this episode of AI & I, Dan Shipper sat down with Gerstenzang and Friedman, partners at Boulton and Watt, which they call the "world's slowest startup incubator." Their model: Come up with an idea, achieve five or 10 million dollars in revenue themselves, then hand it off to a CEO who can take it to the next stage. They've used this playbook to build Moxie, a Series C company that helps nurses open their own medical spas, now with 600-plus customers and a 200-person team globally. Their second company, Meadow Memorials, is a contemporary funeral home with no physical real estate. It has become the largest provider of funeral services in California.Both businesses launched right around the arrival of ChatGPT—and neither was built with AI in mind. So how are they thinking about AI inside companies where the core work isn't going to change? In this conversation, Gerstenzang and Friedman share how they built an AI agent called Matthew Bolton to power their customer discovery process, why synthetic customer calls completely failed for them, and why they believe you shouldn't give anyone credit for using AI.If you found this episode interesting, please like, subscribe, comment, and share!Want even more?Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It's usually only for paying subscribers, but you can get it here for free.To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipperIntent is what comes after your IDE. Try it yourself: augmentcode.com/intentHead to granola.ai/every to get 3 months free.Ready to build a site that looks hand-coded—without hiring a developer? Launch your site for free at www.Framer.com, and use code DAN to get your first month of Pro on the house.Timestamps00:00:00 — Introduction and how Sam and Dan's paths first crossed00:01:40 — What it means to be “the world's slowest incubator”00:04:50 — Why Bolton and Watt runs companies to several million in revenue before handing off to a CEO00:07:30 — How specialization across the founding journey creates advantages00:10:40 — Building AI-durable businesses versus AI-native ones00:16:10 — How an AI agent transformed their customer discovery process00:19:30 — Where synthetic customer calls completely fail00:29:30 — Deploying AI inside established companies00:32:30 — Why newer projects see huge gains from AI while mature companies see 10 percent00:37:00 — A preview of what's next for Bolton and Watt

Silicon Valley loves billion-dollar moonshots and AI darlings. Sam Gerstenzang and Dan Friedman are doing something different—they're starting medical spas and funeral homes.On this episode of AI & I, Dan Shipper sat down with Gerstenzang and Friedman, partners at Boulton and Watt, which they call the "world's slowest startup incubator." Their model: Come up with an idea, achieve five or 10 million dollars in revenue themselves, then hand it off to a CEO who can take it to the next stage. They've used this playbook to build Moxie, a Series C company that helps nurses open their own medical spas, now with 600-plus customers and a 200-person team globally. Their second company, Meadow Memorials, is a contemporary funeral home with no physical real estate. It has become the largest provider of funeral services in California.Both businesses launched right around the arrival of ChatGPT—and neither was built with AI in mind. So how are they thinking about AI inside companies where the core work isn't going to change? In this conversation, Gerstenzang and Friedman share how they built an AI agent called Matthew Bolton to power their customer discovery process, why synthetic customer calls completely failed for them, and why they believe you shouldn't give anyone credit for using AI.If you found this episode interesting, please like, subscribe, comment, and share!Want even more?Sign up for Every to unlock our ultimate guide to prompting ChatGPT here: https://every.ck.page/ultimate-guide-to-prompting-chatgpt. It's usually only for paying subscribers, but you can get it here for free.To hear more from Dan Shipper:Subscribe to Every: https://every.to/subscribeFollow him on X: https://twitter.com/danshipperIntent is what comes after your IDE. Try it yourself: augmentcode.com/intentHead to granola.ai/every to get 3 months free.Ready to build a site that looks hand-coded—without hiring a developer? Launch your site for free at www.Framer.com, and use code DAN to get your first month of Pro on the house.Timestamps00:00:00 — Introduction and how Sam and Dan's paths first crossed00:01:40 — What it means to be “the world's slowest incubator”00:04:50 — Why Bolton and Watt runs companies to several million in revenue before handing off to a CEO00:07:30 — How specialization across the founding journey creates advantages00:10:40 — Building AI-durable businesses versus AI-native ones00:16:10 — How an AI agent transformed their customer discovery process00:19:30 — Where synthetic customer calls completely fail00:29:30 — Deploying AI inside established companies00:32:30 — Why newer projects see huge gains from AI while mature companies see 10 percent00:37:00 — A preview of what's next for Bolton and Watt

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Meet the Slowest Startup Incubator in the World—Pumping Out Billion-dollar Companies

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Silicon Valley loves billion-dollar moonshots and AI darlings. Sam Gerstenzang and Dan Friedman are doing something different—they're starting medical spas and funeral homes.On this episode of AI & I, Dan Shipper sat down with Gerstenzang and...

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