Jason Portnoy had it all. As the 34th employee at PayPal, he was at the heart of the startup boom in Silicon Valley, working alongside the likes of Elon Musk, Peter Thiel and Steve Chen. But despite skyrocketing success and an extravagant rock star lifestyle, behind closed doors the father and husband was quietly battling sex addiction. Shrouded with guilt and shame, Portnoy kept his struggles hidden until he decided to come clean with his book “Silicon Valley Porn Star.”
We CONNECTED with the author, entrepreneur and venture capitalist to talk about his journey of redemption as an investor, husband and father of two. His story offers an enlightening tale for anyone struggling with addiction in the dark.
Portnoy’s book is now available in Traditional Chinese translation.
00:00 Introduction
1:09 What was the energy like during the startup boom in Silicon Valley?
1:44 The culture at PayPal and the World Domination Index
2:59 How did your time at PayPal define success for you?
4:20 Silicon Valley Porn Star?
5:43 How did you manage your 'bad boy' lifestyle, hold down a job, handle family responsibilities and still function day to day?
7:09 How do you handle success with a startup when you reach it?
9:28 Would you change the way you have done things given what you know now?
11:16 Why do you think success led you down a slippery slope in your private life?
13:35 Why did you decide to go public given what's at stake?
17:00 Why did you translate the book into Traditional Chinese?
18:34 Do you think you can spur the conversation around addiction in Asia?
20:24 Lessons from Jason Portnoy's journey
21:47 Were you concerned people wouldn't take you seriously after revealing your journey?
23:18 Did anyone know about this other side of you at the time?
23:43 How much do you keep in touch with your old PayPal pals?
24:48 What advice do you have for maintaining relationships in the startup world?
28:07 Takeaways from working with Elon Musk
29:25 Advice for young entrepreneurs
30:52 What was it about PayPal that made people skyrocket?
32:24 What's the big takeaway from you book?
35:10 How do you define your current self?
37:39 Conclusion
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