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

AI & I

Mar 04
AI & I

AI & I

Mar 04

Shownote

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/subscribe Follow him on X: https://twitter.com/danshipper Intent is what comes after your IDE. Try it yourself: augmentcode.com/intent Head 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. Timestamps 00:00:00 — Introduction and how Sam and Dan's paths first crossed 00:01:40 — 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 CEO 00:07:30 — How specialization across the founding journey creates advantages 00:10:40 — Building AI-durable businesses versus AI-native ones 00:16:10 — How an AI agent transformed their customer discovery process 00:19:30 — Where synthetic customer calls completely fail 00:29:30 — Deploying AI inside established companies 00:32:30 — Why newer projects see huge gains from AI while mature companies see 10 percent 00:37:00 — A preview of what's next for Bolton and Watt

Highlights

Sam Gerstenzang and Dan Friedman are redefining startup building—not with AI-first hype, but with patience, domain depth, and human-centered services in resilient industries like medical aesthetics and end-of-life care.
00:00
There are two types of companies in the AI era: those building the infrastructure and those applying it to real-world problems
04:28
Meadow Memorials is the largest funeral service provider in California and operates without physical real estate
04:54
Moxie launched before ChatGPT and built a self-sustaining business by focusing on market signals and iterative execution
07:31
Avoiding existential dread by not being directly responsible for the middle years of a single company
13:27
Med spa core work is not deeply affected by AI, despite early adoption of new medical technologies
18:52
Mega prompts generate business categories and assess viability, then narrow to a few for human validation
22:19
Matthew Bolton rereads the point of view, hypothesis tracker, and recent calls to update evidence for hypotheses and guide decision-making
29:35
Claude can cover a wider breadth but might not produce as interesting or new results as a human
35:00
Sam Gerstenzang's team trained an AI on his blog posts to reach out to candidates on LinkedIn
37:06
AI adoption in big companies focuses on internal exemplars, not broad transformation

Chapters

Introduction and how Sam and Dan's paths first crossed
00:00
What it means to be “the world's slowest incubator”
01:40
Why Bolton and Watt runs companies to several million in revenue before handing off to a CEO
04:50
How specialization across the founding journey creates advantages
07:30
Building AI-durable businesses versus AI-native ones
10:40
How an AI agent transformed their customer discovery process
16:10
Where synthetic customer calls completely fail
19:30
Deploying AI inside established companies
29:30
Why newer projects see huge gains from AI while mature companies see 10 percent
32:30
A preview of what's next for Bolton and Watt
37:00

Transcript

Dan Shipper: I love this, Oh, thanks. Dan Friedman: I feel like that's actually really meaningful. You know, I got to say, Sam and I this morning looked at each other and we were like, are we sure we should be on this podcast? There's two good companies t...