The Inner Game of Startups: Raw, weekly email on the mental side of building a company.

(“The Inner Game of Startups" is an obvious tip of the hat to the phenomenal book, "The Inner Game of Tennis", about the mental side of the sport.) This weekly newsletter isn’t just for you. It’s for me too. It's a selfish act. Not for money, but catharsis! After (mostly) bootstrapping one company to profitable growth then starting a new VC backed company in 2018, I felt like the crazy mind-game aspect of startups is under-appreciated, or at least not talked about until AFTER people are successful. I wanted to share the process WHILE I'm in the midst of it. But it's a little scary to be that open. That's where the idea for a paid newsletter on Substack came in. It's amazing what having it gated behind a small paywall does for making me more comfortable and open, and making the whole process more enjoyable! The goal is not to make a killing on a newsletter, it’s to create a filter so that subscribers are those who are keenly interested in knowing the weekly struggles of startup building, enough to put in a few bucks ($5 a month). It creates a high quality audience, and keeps me more attuned to what readers find valuable. I write a new issue every Friday. Building a great company is hard (Crash.co is my current company). And it’s kinda lonely too. I’m pretty open and transparent, and try not to put a spin on our progress and challenges. Still, the vast majority of startup experiences happen between the ears of the founders. You go through so much that no one really knows about. All the things you almost did but didn’t, the things you second guess, the deflating or inspiring conversations with investors or customers, the changes in plan, and the constant effort to manager your own mental game. I’m sorta tired of keeping it to myself, and writing is my favorite activity. So every week, I’m going to share exactly where we are, and what I’m thinking and feeling in real time. This is not a “How to” newsletter. Tons of people have had far more success than me building companies and many great books and podcasts exist with those kinds of publicly consumable tips. This is a “How it is” newsletter. I’ll be sharing my own, totally subjective experiences as we work to build a truly great company we can be proud of. I’d love to have you come along. I’d especially love questions from other founders, aspiring founders, customers, or investors. It better will help me tease out my own thoughts. Thanks!