The Climb Up Cringe Mountain

Every founder story you have been told is missing the middle. You get the garage and you get the stage. You never get the years in between where the person was mediocre and knew it, because that part does not sell and it does not flatter anyone. The highlight reel is not exactly a lie. It is just the two percent of the footage that looked good. The other ninety eight percent is cringe mountain, and they cut it because you would not have kept watching.

I build in public now on purpose. The scoreboard with the real numbers, the /now page, the rough version shipped before it is ready. Not because it is comfortable, but because the edited version is the lie, and the middle is where I actually live. If I only ever show you the summit, I am selling you the same story that kept me stuck at the bottom of the mountain for years.

My trail of cringe is long and specific. I was the second-grader trading Pokemon cards at recess. The fourth-grader running candy out of a backpack. The teenager flipping iPhones on Craigslist. At sixteen I was at Apple, learning for the first time what it looked like when a company actually loved its people.

Then came the ventures. Some worked. Most taught me things the ones that worked never could. There was a stretch where I was three million in debt, the companies running, the teams shipping, the calendar full, and me at 2 AM asking questions that had nothing to do with money. That night eventually became a 25,000-word essay and the spine of every decision since. But in the moment I was just on the mountain, in the fog, not yet aware it had a name.

I have another talk, Multiply Yourself, built on one idea: friction is not a wall, it is a compass pointing straight at where your leverage has been hiding the whole time. Cringe is friction you can feel in your own body. When you look back at last year’s work and wince, that wince is not shame. It is information.

It is the exact distance between who made that thing and who you are now. The people who never cringe are not more talented. They stopped moving, so the gap between past them and present them closed to zero. I would rather wince at last month than be comfortable with it for the rest of my life. Comfort with your old work is usually not a sign you arrived. It is a sign you stalled.

The middle is not a hallway you rush through to reach the room. The middle is the whole house. The launch is a day. The exit is a day. The middle is a decade, and it is where almost all of the time, the real work, and the person you become actually live.

One of my companies is a heating and cooling business in Las Vegas, and it keeps me honest in a way nothing else does, because you cannot fake your way past someone whose heat is out in July. That is the unglamorous middle made literal. The same boring rep, the same real problem, done well, on a Tuesday when no one is clapping. That is not beneath the work. That is the work.

There is a trap higher up the mountain. You get a little good, people start watching, and you feel the pull to protect the image instead of keep climbing. I have a talk called Best Expression about the costume you wake up in one day and did not choose, and the work it takes to take it off. Becoming a brand of yourself is quietly putting that costume back on.

It is the moment you step off the mountain and onto a stage, where the growth stops, because you have started performing the last version of you instead of building the next one. I do not want to be a perfectly packaged product. I would rather keep some cringe in the frame and stay a person who is visibly still figuring it out, because that is the only state in which anyone actually learns anything or trusts anyone.

I spend my spare hours on a ninety-year-old math problem called the Collatz Conjecture. Take any number, run it through a simple rule, and it seems to fall eventually to one. Nobody has proved why it must. I keep a principle from it that I have started calling the Santana Principle: sufficient awareness guarantees return. Enough honesty about where you actually are, and you find the way back.

That is what cringe mountain has taught me. The wince is awareness. It is the mountain telling you exactly where you are standing. Stay awake to it instead of hiding from it, and the climb always, eventually, leads home.

So if you are somewhere on cringe mountain right now, bad at the thing, embarrassed by your own middle, certain that everyone else skipped this part, I want to tell you plainly that they did not. There is no route around it. The view at the top is real, but it was never the point. The climb is the point. The cringe is proof you are still moving. Keep going. I am still climbing too.