Hi Everyone,
Welcome to my second book update. It's a gorgeous Sunday morning in New York and I'm writing this from a small outdoor table at a French coffee shop on my street corner — the same one where I watched Malcolm Gladwell working on several occasions last summer. Dare to compare!
Where My Head Is
I've turned a corner on this project. I'm still interviewing illustrious founders, but I'm starting to focus on the actual writing. The goal: a finished first manuscript by the end of this summer, so I can stay on path to publish (the book still needs a name) within Q1 of next year. There's nothing special about Q1, but it's the goal I've set and I want to stick with it. (There's no engineering team to blame for delays this time around.)
It takes me 10–15 hours to draft each chapter — and that's before interviews or AI pattern synthesis. So call it one chapter per weekend; weekdays are too jam-packed to write in 30-minute slots between meetings. I'm assuming ~15 chapters (we'll ignore the 27 chapter outlines currently sitting in my Notion database). Then factor in the summer weekends I'll be traveling with my wife, Jess. I'm not going to do the math, but I think it equals "I'm fucked" on hitting my end-of-summer target. Oh well. I'm a founder. If impossible upfront targets held founders back, there'd be no unicorns.
Building a Book Like I Built a Company
I keep noticing parallels between founding a startup and writing a book — in how I approach both, and where each gets hard.
One of the blessings and curses of how I built UpdateAI: I went in with very few fixed assumptions about what I was building. I'd just left BCG's digital incubator, where strong hypotheses were the ultimate villain and the spine of every startup we built came from copious user interviews. So I did the same at UpdateAI. That approach led me to Customer Success and to so many meaningful connections that would serve the company well for years. But the flip side: I never, repeat never, felt I had an inner understanding of the problem I was solving. For most of our near-five-year journey, my vision for the company felt like the "wacky inflatable arms" guy in front of the used car dealership. I needed my own point of view instead of depending on the outside world to hand it to me.
Flash forward to this book. As I sat down last weekend to draft my first chapter (the first one sans AI), I realized how wide an aperture I'd allowed each chapter's theme to become — shaped entirely by the interview material I've been collecting. Same exact pattern as UpdateAI. The upside is great: I've built relationships with you all, and the stories are richer because I haven't forced any founder down a scripted path. But a blank, endless canvas is a brutal place to start each chapter.
So I've resolved on a few fronts:
I'm grateful for every interview I've done and the ones still ahead — I’m gladly seeing those through. But I'm done doing the insurance-salesman move of asking every founder for one more referral. I have enough material. The only intros I need now are additional points of view on vignettes already shared.
I'm taking the time upfront to outline my own thesis for each chapter — and to tell my own story. I'm the least-known founder in this book, something I'm proud of, and I don't want this to become a memoir. But my story is what gives each chapter its spine. And if I don't have a sense of where I'm going, how will I know when I've arrived?
I'm still using AI in earnest, but overuse of it has a way of dehumanizing the work. I'm no longer asking Claude to outline each chapter for me. Old-school style: I'm whipping out my notebook and outlining by hand, combing through every story brief myself (the AI-generated synthesis created after each interview). It brings me closer to the work. The AI is still there, just further in the background. Feels much better.
Since My Last Update
I've spoken to an additional 17 founders and subject-matter experts. So yeah, it's been busy. Here's that list — I pinch myself that these people have been so generous with their time.
Quotes from Recent Conversations that Caught My Eye
"Advisors are like barnacles. They grow on your boat, and they don't come off unless you scrape them off."
"You fall in love to start. You do diligence to logically back out."
"To be a good CEO here, do I need to be a bad person? Like, can I not be a good person and a good CEO at the same time? Do I have to choose?"
What I Need from You
I've finished a rough first draft of a chapter on the personal growth founders go through. I'd love to share it. If you want to read an early version — feedback welcome, but honestly not even required — just reach out.
I still want to supplement the stories with quantitative survey data. Rather than spam this group, I'd love to partner with other founder communities — VCs, meetups, accelerators — who have access to founders willing to take a short survey. Happy to sort out the right quid pro quo.
It's early, but I'm open to recommendations of podcasts or podcasters worth connecting with to help promote the book next year.
And of course, feel free to share this newsletter (www.joshschachter.com) with anyone who'd want to follow along.
Thank you all for your continued support. Still having a ton of fun.
- Josh