#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

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.  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! This episode is brought to you by LinkedIn Marketing Solutions, 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. With a community of more than 770 million professionals, LinkedIn is gigantic, but it can be hyper-specific. You have access to a diverse group of people all searching for things they need to grow professionally. LinkedIn has the marketing tools to help you target your customers with precision, right down to job title, company name, industry, etc. To redeem your free $100 LinkedIn ad credit and launch your first campaign, go to LinkedIn.com/TFS! * This episode is also brought to you by Shopify! Shopify is one of my favorite platforms and one of my favorite companies. Shopify is a platform 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. No coding or design experience required. More than a store, Shopify grows with you, and they never stop innovating, providing more and more tools to make your business better and your life easier. Go to Shopify.com/Tim for a FREE 14-day trial and get full access to Shopify’s entire suite of features. * This episode is also brought to you by Athletic Greens. I get asked all the time, “If you could use only one supplement, what would it be?” My answer is usually AG1 by Athletic Greens, my all-in-one nutritional insurance. I recommended it in The 4-Hour Body in 2010 and did not get paid to do so. I do my best with nutrient-dense meals, of course, but AG further covers my bases with vitamins, minerals, and whole-food-sourced micronutrients that support gut health and the immune system.  Right now, Athletic Greens is offering you their Vitamin D Liquid Formula free with your first subscription purchase—a vital nutrient for a strong immune system and strong bones. Visit AthleticGreens.com/Tim to claim this special offer today and receive the free Vitamin D Liquid Formula (and five free travel packs) with your first subscription purchase! That’s up to a one-year supply of Vitamin D as added value when you try their delicious and comprehensive all-in-one daily greens product. * [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 * For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast. For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Discover Tim’s books: tim.blog/books. 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