I'm Josh Schachter, and I'm writing a book about the relationships that make or break startups.
Building a startup from the ground up isn't just work; it's the most intense professional gauntlet you'll ever run. Period. Some founders, like Zuckerberg, dive into the deep end at nineteen. Others show up with an MBA, a heavy business plan, and a stack of strategy bibles like Crossing the Chasm or The Lean Startup. I've walked all those paths, and I know exactly how much they weigh.
But here is the truth they don't tell you at the starting line: your "moments of truth", the high-stakes split seconds that decide if you scale or sink, almost always come down to People and Relationships.
My hunch? The founders who actually win aren't just building features; they are investing in human capital. They treat connection as their highest-yield asset, even when they don't have a name for it yet.
Ironically, I didn't learn this in a startup garage. I learned it during five years at Boston Consulting Group. At BCG, human capital isn't just an entry on a spreadsheet, it's the only asset. They don't just hire; they curate. They don't just manage; they grow. From intentional "counseling out" to lifelong alumni networks, they prioritize relational investment over the quick, transactional win. When I founded UpdateAI, my most recent startup, which we sold to Gainsight in 2025, that BCG ethos became my creative scaffolding. I took those human-first skills and baked them directly into the architecture of my own company.
As a founder, you have a level of relational influence no one else has. Call it mystique, call it gravity — when you speak, the community leans in. When you interview a candidate, they aren't just talking to a manager; they're talking to the person who started it all. This isn't just a perk; it's an imperative. Big firms can hire a "Chief Evangelist," but it's not the same. Your personal relationships are often heavier than the collective network of the entire firm. That is your soapbox. Use it.
To be clear: I'm not here to tell you that you must be human-first to succeed. Look at Elon. Or Jobs — a man with a prickly reputation who perhaps understood the human psyche better than almost anyone. And being a relational founder isn't a magic bullet. If you don't have product-market fit, you're still in for a rough ride. But relationships offer a distinct advantage.
And yet, there's almost no practical playbook for how to build and sustain the relationships that actually matter. With yourself, your co founders, your team, your investors, your customers.
That's what the book is about. I'm interviewing 50+ founders, collecting original research, and writing in real time. This newsletter is how I'm sharing the journey: 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