Jason Portnoy of PayPal, Palantir, and More — Porn Addiction, The Corrosiveness of Secrets, Healing Wounds, Escaping Shame Cycles, and Books to Change Your Life (#600)

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“Happiness isn’t something you find; it’s what’s left when you get rid of all the things that make you unhappy.”

— Jason Portnoy

Entrepreneur, venture capitalist, and author Jason Portnoy began his career at PayPal, working closely with technology icons like Peter Thiel, Elon Musk, Max Levchin, and Reid Hoffman. He served as the first chief financial officer of Palantir Technologies and later founded Oakhouse Partners, a top-performing venture capital firm.

Jason is sought after as a trusted advisor to technology company CEOs and has spoken on topics ranging from executive leadership to the intersections of technology and humanity. He holds engineering degrees from both Stanford University (MS) and the University of Colorado (BS).

His new book is Silicon Valley Porn Star.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, Google Podcasts, Stitcher, Amazon Musicor on your favorite podcast platform.

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The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#600: Jason Portnoy of PayPal, Palantir, and More — Porn Addiction, The Corrosiveness of Secrets, Healing Wounds, Escaping Shame Cycles, and Books to Change Your Life

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Want to hear another episode about navigating relationships? Listen to my first conversation with psychotherapist Esther Perel here in which we discuss polyamory, why happy people cheat, how to find (and convince) mentors who can change your life, what she’s learned from Holocaust survivors, and much more.

#241: The Relationship Episode: Sex, Love, Polyamory, Marriage, and More (with Esther Perel)

What was your favorite quote or lesson from this episode? Please let me know in the comments.



  • Connect with Jason Portnoy:



  • [04:45] A caffeine-free breakfast
  • [08:22] Background basics
  • [10:52] Education and career diversions
  • [16:51] Getting a job on the merits of an eclectic reading list and company t-shirt
  • [21:47] Early days at PayPal
  • [25:54] Lessons learned from Thiel, Hoffman, and Musk
  • [31:40] Why were so many disparate projects seeded by the PayPal diaspora?
  • [36:59] Peering into Palantir and the low-profile mindset
  • [41:22] Origins of the title Silicon Valley Porn Star
  • [44:02] Recognizing addiction, its escalating consequences, and its contributing factors
  • [53:50] Escaping self-imposed victimhood and rescuing the marriage
  • [1:05:52] Shared therapy and vocabulary
  • [1:08:06] Simplifying and subtracting
  • [1:15:20] Shame spirals and 12 steps (not South Africa)
  • [1:25:22] From Porn Star to The Monk with help via choice reading selections and Coach Melissa
  • [1:30:12] Reconciliation
  • [1:33:22] Most important keys to the repair process
  • [1:34:54] Safeguards against relapse
  • [1:38:02] Modern porn vs. “natural” urges
  • [1:40:11] What compelled Jason to write Silicon Valley Porn Star?
  • [1:44:51] Time for surrender: filling in the post-book timeline
  • [1:50:26] Enduring challenges
  • [1:51:49] Retreat lessons
  • [1:55:36] Jason’s billboard
  • [1:57:34] Books most gifted
  • [1:59:29] Good investments made
  • [2:02:03] The obscure side of Microsoft Excel
  • [2:04:36] What makes a great CFO?
  • [2:08:52] Finance: on the job vs. school
  • [2:11:21] Opening up to a partner about secrets we’ve been holding
  • [2:17:52] Parting thoughts


“Monks don’t have mortgages.”
— Jason Portnoy

“Simplify and subtract.”
— Jason Portnoy

“Happiness isn’t something you find. It’s what’s left when you get rid of all the things that make you unhappy.”
— Jason Portnoy

“So much of this stuff is going on, it’s below the surface. And I think if we talk about it with less shame and less judgment, it could be really healthy for all of us.”
— Jason Portnoy

“Just keep climbing.”
— Jason Portnoy

“Our default state is peacefulness. Our default state is happiness. You would say that children or kids are really good at reading people’s energy. They’re really good at assessing if someone’s safe or not. Animals have this sense. Why do they all have this sense, but adults don’t? What did we do? We put layers and layers of stuff around that core part of ourselves, that intuition. And in order to get back to that place, that default state of peacefulness or happiness or being in tune with others, we had to start peeling away those layers around the outside.”
— Jason Portnoy

“If I live a life of humility, of love for myself, and compassion for others, I can get through just about anything.”
— Jason Portnoy


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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9 Replies to “Jason Portnoy of PayPal, Palantir, and More — Porn Addiction, The Corrosiveness of Secrets, Healing Wounds, Escaping Shame Cycles, and Books to Change Your Life (#600)”

  1. Hi Tim- This interview was incredible. Jason’s vulnerability in opening up about his past with such a personal topic, was beyond inspiring. I agree with Jason, there is a huge need for people to see they are not alone, no one is perfect despite how it looks on the surface. You can seek help and find resources to work on an issue. Change is possible but it takes focused effort. Thank you for continuing to put out amazing content that betters the mind and thanks to Jason for sharing his story.

  2. I’m a therapist and there isn’t just one way to work with people but listening to how the life coach worked with this couple made me cringe to my core. I couldn’t help but think that, had the life coach not been working with both separated husband and wife at the same time for all those years, maybe this man would have had a chance to reveal the full story and get the help he needed sooner. He couldn’t tell his life coach because a part of him couldn’t trust that it wouldn’t get back to his wife. Instead there was a triangulation going on which is so unhelpful and damaging in many ways. This was really apparent when he said his wife didn’t believe him and the life coach didn’t believe him. I’m glad he doesn’t see it that way and it all is better now, but there is a reason therapists don’t do this and have boundaries and ground rules in place when working with couples. A safe contained relationship is so important…is this boundary violation worth the fast pseudo-progress that he thought he was having…? I don’t know but don’t think so…

    1. Having lived through an experience similar to Jason’s, I concur with everything you said. Coach Melissa’s approach made the process take much longer than needed.

  3. I appreciate the common denominator of ‘okay with vulnerability’ that so many of your interviewees have – Jason certainly in a big and inspiring way. In a world where sharing personal stories with strangers is now common place, it’s easy to overlook just how much TRUE COURAGE it takes to show up like he and so many others do on this show. Thanks to Tim leading the way whole-heatedly.

  4. Great episode. I will never forget the part Jason talks about climbing his mountain. There are moments when I forget to keep climbing and pressing forward. I really enjoyed hearing about Peter Thiel and Elon Musk. Thanks for the great content.

  5. Tim, thank you for this interview with Jason. The inner work themes discussed here are ones I discuss often in my women’s circles but rarely hear men discuss. In my personal inner work and coaching practice I often go deep. Often my male clients are more resistant to going there, wanting to focus on the tangible business metrics. I appreciate how you and Jason have affirmed the necessity — and relevance of the inner work to those tangible metrics and to the more important goal of living a fulfilling life. I will be sharing this with my clients. Thank you for your service and the work you do.