Meet the Slowest Startup Incubator in the World—Pumping Out Billion-dollar Companies (45 min)
- Release date: 2026-03-04
- Listen on Spotify: Open episode
- Episode description:
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
Summary
- 🚀 AI-Native vs. AI-Durable: Startups should pursue either cutting-edge AI innovations or resilient real-world businesses enhanced by AI, avoiding crowded AI-native spaces.
- 🧠 Discovery Revolutionized: AI mega-prompts and agents like Matthew Bolton accelerate idea research, call prep, and hypothesis validation with evidence-based rigor.
- ❌ Synthetic Customers Flop: AI fakes excessive enthusiasm, failing to capture real buyer psychology; human interviews are irreplaceable for validation.
- ⚙️ Smart AI Adoption: Expect peak outputs with AI available—no credit for usage alone; showcase examples to elevate team performance organically.
- 📈 Greenfield > Legacy Gains: AI shines in new experiments and prototypes, but mature systems see only incremental boosts, demanding targeted retooling.
Insights
What are the two most promising types of companies to start in the AI era?
Time: 0:11 – 17:07
Category: AI-Driven Innovation EconomyAnswer: Speakers identify AI-native companies that advance categories with AI at the core, and AI-durable companies that leverage AI effectively without altering their fundamental business model, like med spas or funeral homes. This distinction allows focus on resilient, real-world businesses accelerated by AI rather than purely speculative AI ventures. (Start at 0:11)
How can AI supercharge the early-stage company discovery process?
Time: 18:03 – 27:07
Category: AI-Driven Innovation EconomyAnswer: AI enables rapid vertical research via mega-prompts, outperforming manual Googling, and tools like the ‘Matthew Bolton’ agent prepare for customer calls, analyze transcripts, and update hypotheses with evidence quotes. This keeps founders rigorous and fact-based amid manic startup energy. (Start at 18:03)
Why do synthetic AI customers fail at validating business ideas?
Time: 21:23 – 22:34
Category: AI Bias & FairnessAnswer: AI personas always express overly positive feedback (10/10 enthusiasm) regardless of prompts to avoid sycophancy, lacking real psychological nuances of industry experts. Real customer interactions remain essential for true validation. (Start at 21:23)
How should teams adopt AI without falling into ‘Potemkin village’ traps?
Time: 33:37 – 38:03
Category: AI in Workforce DisruptionAnswer: Don’t reward mere AI usage; instead, expect optimal outputs assuming AI exists, seeding examples from early adopters and publicly sharing successes to raise the bar. This avoids bad AI-generated content while driving genuine productivity gains. (Start at 33:37)
Where does AI deliver the biggest wins in non-AI-native businesses?
Time: 34:50 – 39:13
Category: AI in Workforce DisruptionAnswer: Greenfield projects like landing pages, throwaway apps, and custom agents (e.g., SamGBT for recruiting) see massive speedups, while legacy integrations remain incremental. Engineers code faster, but deployment and maintenance persist as bottlenecks. (Start at 34:50)
Can advanced models like o1 radically transform mature engineering teams?
Time: 38:17 – 39:13
Category: AI in Workforce DisruptionAnswer: Even with o1, Series C teams report improvements but no ‘night and day’ shift, as newer engineers excel on greenfield but struggle with mature codebases. Retooling is needed to capture benefits beyond basic coding speed. (Start at 38:17)