Know the Deal. Episode 6

Shai Stern is a six-time founder who has spent his career building the back-office infrastructure that businesses depend on: company formation, compliance, insurance, and payments. His companies have collectively served tens of thousands of businesses, and he is now the Founder and CEO of Gotavi, a single platform that helps founders start and run a company across formation, compliance, insurance, payments, and AI. Stern joins Katya Fisher and John Lindsey to talk about the parts of a company that get zero applause but decide whether it survives. They get into why the "boring" side of business is actually where the money lives, what buyers are really paying for when they acquire a back-office company, why trust built over decades is the hardest thing to replicate with software or AI, and the hard-won lessons from six exits about knowing your cap table before you sign.