142. The Truth Will Set You Free — A Conversation with Jason Portnoy

Everything seemed to be going right for Jason Portnoy. While studying engineering at Stanford, his career took a sharp and unexpected turn upward when he met the CEO of a new startup — a company that became PayPal. He was soon offered a job, jumped on the rocketship and didn’t look back. The years that followed led him to success after success, and Jason became a prominent figure in the high-flying worlds of tech and venture capital. The money and opportunities were endless. In the meantime, Jason got married and had his first child. He was living the dream.

But not everything was as it seemed. In fact, Jason was living a secret double life; one that had started with online pornography and led to a dark world of lies, deceptions, extramarital affairs, envelopes full of money, and casual hookups. Eventually, the two worlds collided, causing Jason to rethink everything: where he was, how he got there, and where he was going.

Jason has since turned his life completely around — largely influenced by his life coach, Jason learned that shame thrives in secrecy, that taking radical responsibility for one’s life really can change everything, and that in very literal ways, the truth really does set us free. He’s emerged with a new sense of spirituality and mission, and finds himself on a quest to live a life full of love and service.

Jason recently released a new memoir called Silicon Valley Porn Star, a deeply vulnerable and moving book. And in this episode, he joined us to tell his story. We’re deeply grateful to Jason for his willingness to share what he’s been through and what he’s learned. 

This episode is being released jointly with Jody Moore from Better Than Happy, and was co-hosted by Jody and Tim.