Ex-Palantir CFO, "Silicon Valley Pornstar", and the Crisis of Masculinity

How much is too much

“I had a life many men dream of: money, titles, cars, women. Then one day it all came crashing down, and I realized that deep inside I was miserable, lonely, and scared.

Where did I go wrong? A lifetime of messages from society told me if I had those things I’d be a “real man” and happy.

It was all a lie.

After years of intense work and study, I learned I couldn’t find happiness in material possessions or validation from society. It only existed inside of myself. In my book, I share the story of how it happened: my rise, my fall, and my redemption.

It took almost losing everything I held dear in my life to learn these lessons, and as I climbed out of a very dark place, I realized I was not alone. Many of us struggle with similar stories. I share my story so those of you going through difficult times know you’re not alone. There is hope, and a way out of the dark.

We don’t need to be ashamed of our mistakes. We can embrace them, learn from them, and share them so we can learn from each other.  Perfection is not the goal. The goal is to keep climbing.

I wish you all the best on your journey.

-Jason Portnoy”

If life was a CV, Jason Portnoy had a stellar record. He began his career at PayPal, working closely with Peter Thiel, Elon Musk, Max Levchin, and Reid Hoffman. He served as the first CFO of Palantir Technologies and later founded Oakhouse Partners, a top-performing venture capital firm.

Despite having built a career largely on getting big decisions right consistently, he made colossal mistakes in his personal life. It started with his addiction to pornography. He talks about it at length in his book but the main point is that heavy dosage of pornographic content nudged him towards exploring more.

One day, while browsing Craigslist, he stumbled into a subgroup of people offering more than what pornography could offer. Things started off slowly but soon he was hooked.