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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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[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

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