Jason Portnoy of PayPal, Palantir, and More — Porn Addiction, Sexaholics Anonymous, Shame Spirals, and His Path to Recovery and Redemption (#600)

“Just keep climbing.”

— 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!

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

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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.

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

SCROLL BELOW FOR LINKS AND SHOW NOTES…

SELECTED LINKS FROM THE EPISODE

• Connect with Jason Portnoy:

Website

• Silicon Valley Porn Star: A Memoir of Redemption and Rediscovering the Self by Jason Portnoy | Amazon
• Capitalism’s Favorite Drug by Michael Pollan | The Atlantic
• Why We Sleep: Unlocking the Power of Sleep and Dreams by Matthew Walker | Amazon
• This Is Your Mind on Plants by Michael Pollan | Amazon
• Michael Pollan — This Is Your Mind on Plants | The Tim Ferriss Show #520
• What Exactly Is a California Roll? | Cheap Traffic Attorneys
• Oakhouse Partners
• Hillsborough, New Jersey
• Chemical Engineers | Occupational Outlook Handbook
• University of Colorado Boulder
• The Man Who Taught Me How to Invest — Mike Maples | The Tim Ferriss Show #286
• A Guide to Sand Hill Road: The Epicenter of Venture Capital | Built In San Francisco
• Fogdog | Stanford Graduate School of Business
• PayPal | Wikipedia
• Palo Alto | Hobee’s Restaurant
• Of Mice and Men by John Steinbeck | Amazon
• Tao Te Ching by Lao Tzu | Amazon
• Books by Ernest Hemingway | Amazon
• The Art of War by Sun Tzu | Amazon
• BASES: Business Association of Stanford Entrepreneurial Students
• Financial Analysts | Occupational Outlook Handbook
• Masters of Scale: Surprising Truths from the World’s Most Successful Entrepreneurs by Reid Hoffman, June Cohen, and Deron Triff | Amazon
• Brian Chesky: Do Things That Don’t Scale | Masters of Scale with Reid Hoffman
• X.com | Wikipedia
• University Ave. in Palo Alto, California | Tripadvisor
• Rodin Sculpture Garden in Stanford, California | A Park a Day Bay Area
• The Stepford Wives by Ira Levin | Amazon
• The Truman Show | Prime Video
• Tesla, SpaceX, Boring Company: How Elon Musk’s Companies Work Together | CNBC
• Clarium Capital | Wikipedia
• What is an IPO Roadshow? | Bottle Rocket Media
• When Genius Failed: The Rise and Fall of Long-Term Capital Management by Roger Lowenstein | Amazon
• Ventures of the PayPal Mafia | Fleximize
• Palantir Technologies | Wikipedia
• The Top 10 Signs of Porn Addiction | Addiction Center
• What to Do When Porn Use Becomes a Problem | Psychology Today
• Craigslist Shuts Down Personals Section Because of Sex Trafficking Law | Esquire
• Fluoxetine (Prozac) | NAMI: National Alliance on Mental Illness
• The 30-Day Challenge: No Booze, No Masturbating (NOBNOM) | Tim Ferriss
• Recovery from Sex and Lust Addiction | Sexaholics Anonymous
• Dr. Gabor Maté — New Paradigms, Ayahuasca, and Redefining Addiction | The Tim Ferriss Show #298
• Autobiography of a Yogi (Self-Realization Fellowship) by Paramahansa Yogananda | Amazon
• The Sermon on the Mount: The Key to Success in Life by Emmet Fox | Amazon
• The Lost Booklets of Emmett Fox by Emmet Fox and Carl Tuchy Palmieri | Amazon
• The Seat of the Soul by Gary Zukav | Amazon
• Healing the Shame that Binds You by John Bradshaw | Amazon
• Love Warrior: A Memoir by Glennon Doyle | Amazon
• Women Who Love Too Much: When You Keep Wishing and Hoping He’ll Change by Robin Norwood | Amazon
• Idiom: Canary in the Coal Mine | Funky English
• What Is the “Normal” Frequency of Masturbation? | ISSM
• Is Porn Harmful? The Evidence, the Myths, and the Unknowns | BBC Future
• Do Porn Users Seek Out More Extreme Content Over Time? | Kinsey Institute
• They May Forget What You Said, But They Will Never Forget How You Made Them Feel | Quote Investigator
• The Power of Now: A Guide to Spiritual Enlightenment by Eckhart Tolle | Amazon
• Alcoholics Anonymous: The Big Book by Anonymous | Amazon
• Warren Buffett Was ‘Terrified’ of Public Speaking and Took 3 Steps to Conquer His Fear | Inc.com
• Career Advice from Peter Thiel’s Mentee | Business Insider
• Microsoft Excel Spreadsheet Software | Microsoft 365
• What Does a Chief Financial Officer (CFO) Do? | Investopedia

SHOW NOTES

• [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

MORE GUEST QUOTES FROM THE INTERVIEW

“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

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