AI for Boring Businesses — Sam Gerstenzang

Gerstenzang, co-founder of incubator Boulton and Watt, argues that operationally complex businesses in regulated industries — funeral homes, medical spas, and similar — are better positioned for AI than typical VC-backed SaaS startups. His portfolio includes Meadow (funeral home with no physical locations, using wedding venues during the day) and Moxie (platform for nurses starting aesthetic medicine clinics, $25M Series C).

As software gets easier to build and public SaaS share prices drop 70%+, the pendulum swings toward companies with real-world operational complexity that AI can streamline but not replace. These businesses have high margins, regulatory moats, and operational barriers that make them defensible even as code becomes commoditized.

The piece reframes AI’s impact: instead of creating new pure-software businesses, the biggest opportunity may be applying AI to modernize industries that Silicon Valley has traditionally ignored because they require physical operations, regulatory compliance, and domain expertise.

RDCO Mapping

Reinforces our thesis from Tina He’s boring businesses piece. The “boring but defensible” pattern — regulated industries where operational complexity is the moat — is the exact thesis behind the Sanity Check positioning: data infrastructure is boring, invisible, and irreplaceable. Gerstenzang’s funeral-home-on-wedding-venues model is a great Data Dot candidate.