Book Update #1: What 30 Founders Taught Me So Far

Hey everyone,

This is the first update on my book about the relationships that make or break startups. If you're reading this, it's because you've been part of this journey, whether as an interviewee, a sounding board, an introducer, or a supporter. Thank you.

I want to keep you close to this process, so here's where things stand.

At any time message me and I’ll send you a chapter to read.

I've had the privilege of sitting down with some remarkable founders and investors. Here are some of the people who've contributed their stories so far:

Des Traynor, Godard Abel, Angel Cruzado, Or Offer, Guy Yalif, Cody Barbo, Mike Molinet, Manny Medina, Sam Jacobs, David Sable, Howard Morgan, Todd Olson, Zeb Evans, Henry Schuck, Scott Belsky, Kris Rudeegraap, Alina Vandenberghe, Alex Cox, Saar Yoskovitz, Amir Shevat, Scott Voigt, David Politis, Nick Mehta, Alexis Hennessy, Elias Torres, Alex Rubalcava, Julian Weisser, Colin Nederkoorn, Carole Robin, and more.

Every conversation has deepened my conviction that this book needs to exist.

How one act of kindness shaped a 28-year leadership philosophy
Elias Torres

In 1998, a woman named Deidre at IBM drove through the rain to make sure 21-year-old Elias, a first-generation immigrant from Nicaragua, found his hotel. She took him on a horse carriage ride through Central Park. He chose IBM because of her and stayed ten years. Nearly three decades later, his entire approach to recruiting and team-building traces back to that moment.

The loneliness of leadership
Colin Nederkoorn

Colin has been building Customer.io for 14 years. The thing that's sustained him? A small peer CEO group that meets in person twice a year. He describes the feeling of being in that room: "I have no weight. And that's a really hard feeling to get any other time." For founders, finding people who carry the same weight and can set it down together isn't a luxury. It's survival.

The co-founder decision most people get wrong
Julian Weisser

Most founder advice assumes you need a co-founder. Julian, who ran On Deck Founders and has seen hundreds of founding teams form, argues the opposite: "The presumption should be that you shouldn't have a co-founder unless it's beyond a reasonable doubt." Choosing a co-founder out of convention rather than conviction is one of the most expensive relationship mistakes a founder can make.

Designing good survey questions is hard. I want this book to be backed by quantitative data, not just stories. But building surveys that give me depth without discouraging busy founders from participating has been a real challenge. I also need questions flexible enough to survive as the book's chapters evolve. My current plan: publish shorter, focused mini-surveys over time rather than one massive questionnaire. More on that soon.

I've been deep in the weeds on the book's title, which sounds superficial but has turned into something much bigger.

My working title was The Relational Founder, but a writing coach recently challenged me: every founder thinks they're relational. There's no tension in the statement. A great title needs a more debatable insight, something that stakes a claim.

Right now I'm drawn to People First, Mission Always, a play on the military principle "mission first, people always." The subtitle I'm testing: Moments of Truth in a Founder's Journey. I also like The Human Advantage.

But honestly, the title question has sent me deeper. It's forced me to confront: what is the real thesis of this book? What's the underlying belief I'm validating? What do I want founders to walk away with?

That's what I'll be sitting with in the coming weeks.

Brett Queener also brought something to my attention yesterday that surprisingly no one else has yet: what does this book mean in the age of AI? Will relationships matter more or less? (Do you need relationships when agentic will almost guarantee decisions can be made via verifiable outcomes?). I’m going to look for ways to incorporate AI but without steering the gravity of this book off course.

Introductions. I'm looking for more exceptional, experienced founders who put relationships first and might be willing to sit for an interview. In particular, I need more ethnic and gender diversity in the founders represented in this book. It's been a challenge and I want to get it right. If someone comes to mind, reply to this email or make the intro directly.

Thanks for being part of this. I’m having so much fun. More soon.

- Josh