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Tim Ferriss

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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Artist's rendering of Jason Portnoy.
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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 Music, or on your favorite podcast platform.

Brought to you by LinkedIn Marketing Solutions marketing platform with ~770M users, Athletic Greens all-in-one nutritional supplement, and Shopify global commerce platform providing tools to start, grow, market, and manage a retail business. More on all three below.

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

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#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

This episode is brought to you by LinkedIn Ads, the go-to tool for B2B marketers and advertisers who want to drive brand awareness, generate leads, or build long-term relationships that result in real business impact. To redeem your free $100 LinkedIn ad credit and launch your first campaign, go to LinkedIn.com/TFS!

This episode is brought to you by Shopify! Shopify is one of my favorite platforms and one of my favorite companies. Shopify is designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great-looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. Go to Shopify.com/Tim to sign up for a one-dollar-per-month trial period. It’s a great deal for a great service, so I encourage you to check it out. Take your business to the next level today by visiting Shopify.com/Tim.

This episode is brought to you by AG1! I get asked all the time, “If you could use only one supplement, what would it be?” My answer is usually AG1, my all-in-one nutritional insurance. I recommended it in The 4-Hour Body in 2010 and did not get paid to do so. Right now, get a FREE Welcome Kit, including Vitamin D3+K2 and AG1 Flavor Sampler, when you first subscribe. Visit DrinkAG1.com/Tim to claim this special offer today and receive your 1-year supply of Vitamin D—a vital nutrient for a strong immune system and strong bones!

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.

SCROLL BELOW FOR LINKS AND SHOW NOTES…

SELECTED LINKS FROM THE EPISODE

  • Connect with Jason Portnoy:

Website

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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