In my life I haven't flashed many routes.
Second marriage. Seven companies that failed outright. Three that did okay. One that I've spent eight years building and still don't know how it ends.
In climbing, flashing means you climb a route perfectly on the first try. No falls, no rest, no prior attempts. Clean from the ground up. That's not my life. My life is the other thing — the redpoint. You study the route. You fall on it. You figure out exactly where you keep falling and why. And then you go back up.
Redpoint Rack has been my consulting LLC for years, but it started as something else entirely. When my wife Jennifer and I got married we were going to open a second-hand outdoor clothing store in Minneapolis. Mid to high-end gear — the stuff serious climbers and hikers actually want — consigned and sold for a fraction of retail. We formed the LLC, had logos designed, opened bank accounts. Couldn't pull it together. I liked the logo, so when I needed an entity for software consulting I used it. It stuck.
The name comes from the climbing term. A redpoint is when you complete a route cleanly — but only after you've previously fallen on it, projected it, figured out every hard move through failure. Most serious climbers spend the majority of their time projecting routes they can't yet climb. The redpoint is the payoff for all of that honest work.
That's what this is. Round two. I know the wall. I know every crux move. I know exactly where I fell and why.
For the last eight years I've been building a vertical SaaS company as CTO. I co-founded it. We took it from zero to eight figures in ARR over eight years on minimal outside capital. Learned more than I wanted to about governance, equity, what a cap table actually means versus what you're told it means, and the difference between a company built to return capital to shareholders and a company built to create a lifestyle.
I'm not going to name the company. I'm not going to name names. But I'm going to tell you everything I learned — because somebody should.
This newsletter is that. It's also the live story of what I'm building next — three software products, one small team, AI as leverage, and my wife and partner Jennifer running GTM in a way that consistently makes me feel like I wasted eight years doing it wrong.
Welcome to Redpoint Rack. The flash would have been cleaner. But we're here now.