Jacob Heller, The $650M Exit Playbook

​Get ready for a night you'll be talking about for years, an off-the-record dinner with Jacob Heller, co-founder and CEO of Casetext, the AI-powered legal tech company that Thomson Reuters scooped up for **$650 million in cash** in 2023. One of the most celebrated exits in AI history, full stop. Jacob made waves at YC Startup School 2025 breaking down exactly how Casetext went from idea to acquisition, and now he's bringing that same raw, unfiltered conversation to your dinner table in Palo Alto.

​This is a rare chance to sit across from someone who's actually done it, who picked the right market, shipped AI products that real enterprises deployed at scale, and navigated the high-stakes art of selling a company at the top. Expect a candid dive into how to spot ideas that scale beyond demo day, what separates AI products customers actually use from ones they abandon, how to build enterprise value out of early momentum, the psychology of staying sharp across a long founder journey, and the real mechanics of negotiating a nine-figure acquisition.

​Only 10 seats available.
Each selected guest will be required to cover their dinner spot to confirm attendance.