AI durable vs AI native strategy

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.

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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