I'm Josh Schachter, and I'm writing a book about the relationships that make or break startups.
I’ve spent 20 years founding and building companies, most recently UpdateAI, which we sold to Gainsight in 2025. Across three of my own startups and a career in the trenches of startup-building for corporations, I kept arriving at the same conclusion: the moments that define a startup almost always come down to people.
And yet there's almost no practical playbook for founders on how to build and sustain the relationships that actually matter. With yourself, your cofounders, your team, your investors, your customers.
That's what the book is about. And this newsletter is how I'm sharing the journey.
I'm interviewing 50+ founders, collecting original research, and writing in real time. Every issue includes progress updates, insights from conversations with remarkable founders, things I'm wrestling with, and the occasional ask for help.
I publish once or twice a month. If this sounds interesting, subscribe. If it stops being interesting, unsubscribe. No hard feelings.
— Josh