#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 http://linkedin.com/tfs marketing platform with ~770M users, Athletic Greens http://athleticgreens.com/tim all-in-one nutritional supplement, and Shopify http://shopify.com/tim global commerce platform providing tools to start, grow, market, and manage a retail business. Entrepreneur, venture capitalist, and author Jason Portnoy http://jasonportnoy.com/ 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 https://www.amazon.com/Silicon-Valley-Porn-Star-Rediscovering/dp/154453213X/?tag=offsitoftimfe-20. Please enjoy! This episode is brought to you by LinkedIn Marketing Solutions https://linkedin.com/TFS, the go-to tool for B2B marketers and advertisers https://linkedin.com/TFS 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 https://linkedin.com/TFS 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 https://linkedin.com/TFS 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 https://linkedin.com/TFS! * This episode is also brought to you by Shopify http://shopify.com/tim! Shopify http://shopify.com/tim is one of my favorite platforms and one of my favorite companies. Shopify http://shopify.com/tim 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 http://shopify.com/tim. * This episode is also brought to you by Athletic Greens https://www.athleticgreens.com/tim. I get asked all the time, “If you could use only one supplement, what would it be?” My answer is usually AG1 https://www.athleticgreens.com/tim by Athletic Greens https://www.athleticgreens.com/tim, 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 https://www.athleticgreens.com/tim further covers my bases with vitamins, minerals, and whole-food-sourced micronutrients that support gut health and the immune system. Right now, Athletic Greens https://www.athleticgreens.com/tim 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 https://www.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 http://tim.blog/podcast, please visit tim.blog/podcast https://tim.blog/podcast/?utm_source=podcast&utm_medium=podcast&utm_campaign=podcast-description. For deals from sponsors of The Tim Ferriss Show http://tim.blog/podcast, please visit tim.blog/podcast-sponsors http://tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday https://go.tim.blog/5-bullet-friday-1/. For transcripts of episodes, go to tim.blog/transcripts http://tim.blog/transcripts. Discover Tim’s books: tim.blog/books http://tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss https://twitter.com/tferriss Instagram: instagram.com/timferriss https://instagram.com/timferriss/ YouTube: youtube.com/timferriss https://www.youtube.com/timferriss Facebook: facebook.com/timferriss https://www.facebook.com/TimFerriss/ LinkedIn: linkedin.com/in/timferriss http://linkedin.com/in/timferriss Past guests on The Tim Ferriss Show http://tim.blog/podcast include Jerry Seinfeld https://tim.blog/2020/12/08/jerry-seinfeld/, Hugh Jackman https://tim.blog/2020/06/26/hugh-jackman/, Dr. Jane Goodall https://tim.blog/2020/04/16/jane-goodall/, LeBron James https://tim.blog/2018/11/27/lebron-james-mike-mancias/, Kevin Hart https://tim.blog/2020/05/20/kevin-hart/, Doris Kearns Goodwin https://tim.blog/2018/09/07/doris-kearns-goodwin-leadership/, Jamie Foxx https://tim.blog/2015/12/06/jamie-foxx/, Matthew McConaughey https://tim.blog/2020/10/19/matthew-mcconaughey/, Esther Perel https://tim.blog/2017/05/21/esther-perel/, Elizabeth Gilbert https://tim.blog/2020/05/08/elizabeth-gilbert/, Terry Crews https://tim.blog/2017/12/20/terry-crews-how-to-have-do-and-be-all-you-want/, Sia https://tim.blog/2020/08/12/sia/, Yuval Noah Harari https://tim.blog/2020/10/27/yuval-noah-harari/, Malcolm Gladwell https://tim.blog/2016/06/21/malcolm-gladwell/, Madeleine Albright https://tim.blog/2020/05/27/secretary-madeleine-albright/, Cheryl Strayed https://tim.blog/2017/03/30/cheryl-strayed/, Jim Collins https://tim.blog/2019/02/18/jim-collins/, Mary Karr, https://tim.blog/2020/11/11/mary-karr/ Maria Popova https://tim.blog/2014/10/21/brain-pickings/, Sam Harris https://tim.blog/2020/05/15/sam-harris-2/, Michael Phelps https://tim.blog/2021/01/21/michael-phelps-grant-hackett/, Bob Iger https://tim.blog/2020/01/16/bob-iger/, Edward Norton https://tim.blog/2019/10/31/edward-norton-motherless-brooklyn/, Arnold Schwarzenegger https://tim.blog/2015/02/02/arnold-schwarzenegger/, Neil Strauss https://tim.blog/2014/06/24/neil-strauss/, Ken Burns https://tim.blog/2019/09/12/ken-burns/, Maria Sharapova https://tim.blog/2017/08/26/maria-sharapova/, Marc Andreessen https://tim.blog/2016/05/29/marc-andreessen/, Neil Gaiman https://tim.blog/2019/03/28/neil-gaiman/, Neil de Grasse Tyson https://tim.blog/2019/10/03/neil-degrasse-tyson/, Jocko Willink https://tim.blog/2016/09/21/jocko-willink-on-discipline-leadership-and-overcoming-doubt/, Daniel Ek https://tim.blog/2020/12/03/daniel-ek/, Kelly Slater https://tim.blog/2020/09/08/kelly-slater/, Dr. Peter Attia https://tim.blog/2019/11/27/peter-attia-fasting-metformin-longevity/, Seth Godin https://tim.blog/2016/02/10/seth-godin/, Howard Marks https://tim.blog/2018/09/25/howard-marks/, Dr. Brené Brown https://tim.blog/2020/02/06/brene-brown-striving-self-acceptance-saving-marriages/, Eric Schmidt https://tim.blog/2019/04/09/eric-schmidt/, Michael Lewis https://tim.blog/2020/05/01/michael-lewis/, Joe Gebbia https://tim.blog/2018/03/08/joe-gebbia-co-founder-of-airbnb/, Michael Pollan https://tim.blog/2018/05/06/michael-pollan-how-to-change-your-mind/, Dr. Jordan Peterson https://tim.blog/2021/03/01/jordan-peterson/, Vince Vaughn https://tim.blog/2017/05/31/vince-vaughn/, Brian Koppelman https://tim.blog/2020/04/23/brian-koppelman/, Ramit Sethi https://tim.blog/2019/05/07/ramit-sethi/, Dax Shepard https://tim.blog/2020/11/18/dax-shepard/, Tony Robbins https://tim.blog/2014/10/15/money-master-the-game/, Jim Dethmer https://tim.blog/2020/05/18/jim-dethmer/, Dan Harris https://tim.blog/2020/11/19/dan-harris/, Ray Dalio https://tim.blog/2017/09/13/ray-dalio/, Naval Ravikant https://tim.blog/2015/08/18/the-evolutionary-angel-naval-ravikant/, Vitalik Buterin https://tim.blog/2021/03/08/vitalik-buterin-naval-ravikant/, Elizabeth Lesser https://tim.blog/2021/03/16/elizabeth-lesser/, Amanda Palmer https://tim.blog/2019/04/18/amanda-palmer-2/, Katie Haun https://tim.blog/2021/02/18/katie-haun/, Sir Richard Branson https://tim.blog/2017/10/09/richard-branson/, Chuck Palahniuk https://tim.blog/2020/09/02/chuck-palahniuk/, Arianna Huffington https://tim.blog/2017/10/18/arianna-huffington/, Reid Hoffman https://tim.blog/2015/08/31/the-oracle-of-silicon-valley-reid-hoffman-plus-michael-mccullough/, Bill Burr https://tim.blog/2017/09/17/bill-burr/, Whitney Cummings https://tim.blog/2015/06/26/whitney-cummings/, Rick Rubin https://tim.blog/2015/05/15/rick-rubin/, Dr. Vivek Murthy https://tim.blog/2020/03/26/vivek-murthy/, Darren Aronofsky https://tim.blog/2017/09/09/darren-aronofsky/, and many more. 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Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Tim Ferriss?

  This episode is brought to you by Shopify. Shopify is one of my favorite companies out there, one of my favorite platforms ever. And let's get into it. Shopify is a platform, as I mentioned, designed for anyone to sell anything, anywhere, giving entrepreneurs the resources once reserved for big business. So what does that mean? That means in no time flat, you can have a great looking online store that brings your ideas, products, and so on to life. And you can have the tools to manage your day to day business and drive sales. This is all possible without any coding or design experience whatsoever. Shopify instantly lets you accept all major payment methods. Shopify has thousands of integrations and third-party apps from on-demand printing to accounting to advanced chatbots, anything you can imagine.

• 0:44Tim Ferriss?

  They probably have a way to plug and play and make it happen. Shopify is what I wish I had had when I was venturing into e-commerce way back in the early 2000s. What they've done is pretty remarkable. I first met the founder, Toby, in 2008, when I became an advisor, and it's been spectacular. I've loved watching Shopify go from roughly 10 to 15 employees at the time to 7,000 plus today, serving customers in 175 countries with total sales on the platform exceeding $400 billion. But what does that really mean? That means every 28 seconds, more or less, a small business owner makes their first sale on Shopify. More people in more places of all ages every single day.

• 1:27Tim Ferriss?

  They power millions of entrepreneurs from their first sale all the way to full scale. And you would recognize a lot of large companies that also use them who started small. So get started by building and customizing your online store, again, with no coding or design experience required. Access powerful tools to help you find customers, drive sales, and manage your day to day. Gain knowledge and confidence with extensive resources to help you succeed. And I've actually been involved with some of that way back in the day, which was awesome, the Build a Business competition and other things. Plus, with 24/7 support, you're never alone. And let's face it, being an entrepreneur can be lonely, but you have support, you have resources, you don't need to feel alone in this case.

• 2:10Tim Ferriss?

  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. That's S-H-O-P-I-F-Y.com/Tim. All lowercase for a free 14-day trial and get full access to Shopify's entire suite of features. Start selling on Shopify today. Go to Shopify.com/Tim right now and check it out. They have a lot to offer. Shopify.com/Tim.

• 2:44Tim Ferriss?

  This episode is brought to you by Athletic Greens. I get asked all the time what I would take if I could only take one supplement. The answer is invariably Athletic Greens. I view it as all-in-one nutritional insurance. I recommended it, in fact, in The Four Hour Body. This is more than 10 years ago and I did not get paid to do so. With approximately 75 vitamins, minerals, and whole food sourced ingredients, you'd be very hard pressed to find a more nutrient-dense and comprehensive formula on the market. It has multivitamins, multimineral, greens complex, probiotics and prebiotics for gut health, an immunity formula, digestive enzymes, adaptogens, and much more. I usually take it once or twice a day just to make sure I've covered my bases if I miss anything I'm not aware of.

• 3:28Tim Ferriss?

  Of course, I focus on nutrient-dense meals to begin with. That's the basis. But Athletic Greens makes it easy to get a lot of nutrition when whole foods aren't readily available. From travel packets, I always have them in my bag when I'm zipping around. Right now Athletic Greens is giving my audience a special offer on top of their all-in-one formula, which is a free vitamin D supplement and five free travel packs with your first subscription purchase. Many of us are deficient in vitamin D. I've found that true for myself, which is usually produced in our bodies from sun exposure. So adding a vitamin D supplement to your daily routine is a great option for additional immune support. Support your immunity, gut health, and energy by visiting AthleticGreens.com/Tim.

• 4:12Tim Ferriss?

  You'll receive up to a year's supply of vitamin D and five free travel packs with your subscription. Again, that's AthleticGreens.com/Tim.

• 4:22Speaker 01

  At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question?

• 4:29Tim Ferriss?

  No, it is an inappropriate time.

• 4:33Tim Ferriss?

  Why don't you just tell me what you had for breakfast as a starting point? What did you have for breakfast?

• 4:49Speaker 01

  I had these amazing scrambled eggs and sausage and fruit and orange juice.

• 5:00Tim Ferriss?

  Sounds like a very complete breakfast.

• 5:03Speaker 01

  It was very complete, except it's missing the coffee. I love coffee, but I'm not drinking coffee right now because it was interfering with my sleep.

• 5:10Tim Ferriss?

  Hmm. Let's just talk about that for a second. So caffeine, sleep, sleep is my number one priority right now.

• 5:17Speaker 01

  Yeah.

• 5:18Tim Ferriss?

  How did you end up removing caffeine? Because that can be sometimes difficult. Did you just go cold turkey?

• 5:25Speaker 01

  I just went cold turkey. I was only drinking a cup of coffee with breakfast in the morning. Maybe a cup of decaf in the afternoon.

• 5:33Tim Ferriss?

  Yeah.

• 5:33Speaker 01

  But then I was having trouble sleeping the last few months and I kept thinking it was just kind of stress and nerves around the book launch and all of this stuff, this uncharted territory. And then finally, about eight days ago, I was like, maybe it's caffeine. Let me just not have coffee today. And that night I slept so hard I drooled on my pillow.

• 5:57Tim Ferriss?

  One cup?

• 5:58Speaker 01

  Yeah. That was it. And I think it affects different people differently, right?

• 6:02Tim Ferriss?

  Yeah, it does. And I have genetically a predisposition, or I suppose it's kind of a determinism to caffeine fast metabolism. So I clear it, or I used to clear it very quickly, but as you age, your ability to clear it, I suppose, through the liver and through other means diminishes. So in effect, the half-life of caffeine gets longer as you get older. So I've been coming to the same conclusion. I'm reading. Why We Sleep, I think it is by Matt Walker right now.

• 6:34Speaker 01

  Mm hmm.

• 6:35Tim Ferriss?

  And he mentioned this, and I've been progressively cutting back on caffeine, but god damn, do I love stimulants. It's hard.

• 6:43Speaker 01

  Well, I love, I love coffee. So the second night I slept so deeply, it was like disorienting. I woke up in the middle of the night. I felt like I was drowning in the ocean and I was like, no, don't, don't send me back, back there. And then I fell asleep again and I've just been sleeping like a baby for the last week.

• 7:01Tim Ferriss?

  All right.

• 7:01Speaker 01

  And I did this once before I went a whole year, but then I started drinking coffee again.

• 7:05Tim Ferriss?

  You went a whole year without coffee?

• 7:07Speaker 01

  Yeah.

• 7:08Tim Ferriss?

  Wow. Incredible control. Well, I can stay off the caffeine wagon for a few weeks at a time.

• 7:15Speaker 01

  Okay.

• 7:16Tim Ferriss?

  And then I develop a tolerance so quickly. Once I have one cup, what will generally happen is I'm having it in, say, a restaurant. If I have it in a coffee shop, it's safer because you have to pay for the second cup. In a restaurant.

• 7:28Speaker 01

  You just keep going.

• 7:29Tim Ferriss?

  The endless cup of coffee phenomenon starts to manifest. And then I've had three cups. And then before I know it, if I have a day without caffeine, I just feel like I'm asleep on my feet. Right? Because caffeine blocks, or I shouldn't say, eh, in effect, like blocks adenosine, which builds up over time in your system and creates this sleep pressure.

• 7:51Speaker 01

  Yes.

• 7:52Tim Ferriss?

  And it, I think it's an antagonist, or it might be, officially occupies the receptor that adenosine is.

• 7:58Speaker 01

  Did you read Michael Pollan's latest book?

• 8:01Tim Ferriss?

  I think so. I believe so. This would have been.

• 8:04Speaker 01

  This is your mind on plants?

• 8:05Tim Ferriss?

  Morphine, caffeine and mescaline.

• 8:07Speaker 01

  That's right. Yeah.

• 8:08Tim Ferriss?

  Yes.

• 8:08Speaker 01

  Yeah.

• 8:09Tim Ferriss?

  Yeah.

• 8:09Speaker 01

  He talks about that. Yeah.

• 8:10Tim Ferriss?

  It was great.

• 8:11Speaker 01

  Any aversion to me mentioning other books, authors, anything like that?

• 8:16Tim Ferriss?

  No, please do. Please do. So let's, let's set some context here.

• 8:19Speaker 01

  Yeah, let's do it.

• 8:20Tim Ferriss?

  And we might just start the interview with what we just did.

• 8:22Speaker 01

  We're just going to get a rolling start here.

• 8:23Tim Ferriss?

  Yeah, this is like the California roll. Uh, as the police officer once told me, the nonstop stop at a stop sign where you're just gonna take down to five. I don't recommend this, folks. Talk to your local law enforcement before you try anything like that. My guest today, Jason Portnoy. Nice to see you. And we are here in. Beautiful Austin, Texas at the moment. Who is Jason? 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, AKA CFO, of Palantir Technologies and later founded Oak House Partners, a top performing venture capital firm. Jason is sought after as a trusted advisor to technology company CEOs

• 9:08Tim Ferriss?

  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. That is BS, not BS's in, you guys should know what I mean by now. His new book, which we will get to, is Silicon Valley Porn Star. What a title. And we will certainly delve into the origins of that. But let's start with the basics first. Just paint a picture, and this is the kind of boring foundational work for this interview, but you're gonna have to do a lot of this stuff in other interviews, so might as well get some practice in.

• 9:46Speaker 01

  Sure.

• 9:46Tim Ferriss?

  Where'd you grow up? Basics of the family, just the connective tissue of childhood, maybe just a little bit of that to get us started.

• 9:54Speaker 01

  I grew up in the suburbs of New Jersey, a town called Hillsborough, New Jersey. My parents both worked. I had a sister, or still have a sister, who's about five years older than me. We had a couple cats, a family dog. It was pretty quintessential suburban life. There were sidewalks on the street. I played with my friends on the street. We had a pool in the backyard. It was great.

• 10:16Tim Ferriss?

  What did your parents do professionally?

• 10:18Speaker 01

  They were both chemists, interestingly.

• 10:21Tim Ferriss?

  Chemists. And did you follow in those footsteps?

• 10:25Speaker 01

  I did. When I went off to college, I didn't really know exactly what I wanted to do, but I liked chemistry and I liked math. And my dad suggested, why don't you do chemical engineering? Because it will be a blending of those two things. And so I said, great. Actually, then I looked up on a table of starting salaries for different majors. And at the time, chemical engineers made the highest starting salary of any major in college. And I said, that's perfect.

• 10:50Tim Ferriss?

  Sounds good. Sign me up. For those who don't know, what does a chemical engineer do? And what is chemical engineering?

• 10:59Speaker 01

  I would be lying if I said I knew exactly because I never worked as a chemical engineer. So I studied it. When I was studying that in college, a lot of it was around things in the oil and gas industry. And so I think at a high level, you could say a chemist might figure something out in a laboratory, some kind of chemical process, and then a chemical engineer might be responsible for figuring out how to mass produce that thing. So a chemist maybe makes a little bit in a vial, but how do you make tons and tons and tons of this stuff? It's actually really challenging because you have heat and thermal dynamics and all kinds of stuff like that.

• 11:38Tim Ferriss?

  I would imagine with the energy sector and hydrocarbon industries in Texas, there are probably a lot of chemical engineers in Texas.

• 11:46Speaker 01

  A lot, yes.

• 11:47Tim Ferriss?

  There must be.

• 11:47Speaker 01

  Yeah.

• 11:48Tim Ferriss?

  When did you diverge from your preordained, high-paying career as a chemical engineer?

• 11:56Speaker 01

  Well, it probably started in college when I was an undergrad. I was at University of Colorado at Boulder. And at some point, my dad, always giving me suggestions on what to study, said, maybe you should get a minor in business so you at least learn the basics. And the minor in business that I got was like one accounting class, one finance class, one macroeconomics class, one microeconomics class, and so on and so forth. And then, when I went off to grad school, if you think about what I had studied as an undergrad, I had chemistry, math, and now business. And I liked the intersection of the math and the business more than I liked the intersection of the other, any of the other things. And

• 12:40Speaker 01

  so I got a master's degree at Stanford in a field that was really a combination of math and business.

• 12:46Tim Ferriss?

  What is the, like ORF, ORF? No?

• 12:50Speaker 01

  So, different schools, call it by different names. Sometimes you'll hear operations research. Sometimes you'll hear industrial engineering. A lot of times, those departments are combined. So it'll be IEOR, industrial engineering and operations research. Stanford's department, I forget the name when I first got there, but the name changed to management science and engineering. And so my, that's why technically my degree is in.

• 13:14Tim Ferriss?

  And you went straight from undergrad to grad school?

• 13:18Speaker 01

  I did.

• 13:18Tim Ferriss?

  All right. What was your thinking behind that? What was the, at least tentative, plan or hope or?

• 13:26Tim Ferriss?

  Thinking if any behind that.

• 13:28Speaker 01

  I just thought that's what everyone did. I didn't know that there was any, I didn't know that there was any other way. My parents had all gone to graduate school and they had gone directly after undergrad and I just thought that's what you did.

• 13:41Tim Ferriss?

  That's what someone does.

• 13:42Speaker 01

  Yeah. And I actually, I really had tried to get into a PhD program. I thought that that was my destiny and I didn't. And I was really upset about that. And for the first year, when I was in graduate school, I was trying so hard to get into the PhD program and I couldn't. And looking back, I think it's probably a good thing. I think the life of a PhD researcher probably wouldn't have suited me as well as, as the direction I've gone in.

• 14:09Tim Ferriss?

  I had a friend of mine on a long time ago on the podcast named Mike Maples, Mike Maples, Jr., who was the first person to introduce me to angel investing and explain in some respect how the basics work.

• 14:23Speaker 01

  He's a good teacher.

• 14:23Tim Ferriss?

  He's, yeah, I owe Mike a lot. And I remember, I think it was Mike who said on the podcast, sorry, Mike, if I'm misquoting it, but it's a pretty good quote. So you can take the half credit anyway. He said something like, sometimes we need life to save us from what we want.

• 14:39Speaker 01

  Right.

• 14:39Tim Ferriss?

  And that might be an example of that.

• 14:41Speaker 01

  Absolutely.

• 14:42Tim Ferriss?

  So you didn't get into this PhD program. There you are at Stanford. What are some of the more formative things or impactful occasions that come about while you're at Stanford?

• 14:58Speaker 01

  So I went directly from undergrad, but what I found was most of my classmates had not. So a lot of them had gone and had some kind of prior work experience before coming to grad school. Consulting was a big one. Investment banking was a big one. Some of them had family businesses that they helped run.

• 15:16Tim Ferriss?

  Now, are these people in your program? Are they people who are at the Graduate School of Business, GSB?

• 15:23Speaker 01

  Both. So the program that I was in had classes co-listed with the GSB. So I was sometimes attending classes in the GSB and sometimes you had GSB students in our classes. And a lot of these people had some. Prior work experience and after a while, after a few months in school, I realized it was really helpful for them because they could contextualize the things that we were learning. And whereas for me, it was all very abstract. And so I decided I wanted to get a job and that if I should continue like that.

• 15:55Tim Ferriss?

  Just continue. I get pretty bored interviewing myself.

• 15:57Speaker 01

  Well, actually, there was, there was a, there was a career fair around that time. So this was just to set the stage, I guess. It was late 1999. The dot com boom is in full swing. All these companies have tons of capital from Sand Hill Road, venture capital investors, and they're hiring like crazy and they're on Stanford's campus. So there's a career fair. There's a guy running around in a dog costume. I think the company was called Fog Dog. I thought it was hilarious and I really wanted to work there.

• 16:28Tim Ferriss?

  So the dog outfit worked.

• 16:30Speaker 01

  The dog outfit worked. So I applied there, didn't get a job there. So maybe again, life sending me the right things. I don't know. Shortly after that, I submitted my resume to a company that was advertising in a newsletter called Confinity. And then I got invited in for a job interview and that company later turned into PayPal.

• 16:51Tim Ferriss?

  So let's talk about this job interview.

• 16:55Speaker 01

  Oh, yeah.

• 16:55Tim Ferriss?

  Let me shake out my notes. Here we go. Perfect segue. So you interviewed with the CEO of Confinity. I'm going to read this literally, who hired you because of your reading list, or at least partially, that was a factor. So who was that CEO? What was the company at the time, right? What did it do? And most interesting to me perhaps is the reading list. I'd love to know what was on the reading list.

• 17:17Speaker 01

  Well, you jokingly said, I got hired because of the reading list, but he later joked that I got hired because I wore a company T-shirt to the interview.

• 17:26Tim Ferriss?

  Oh, no kidding.

• 17:26Speaker 01

  But a very good natured joke. So the company was called Confinity. It was a company that had been started by Peter Thiel and Max Levchin. And the intention was to allow people to beam money to each other on their Palm Pilots. That was the way the product worked. I guess the intention was it was really the beginning of a cryptographic currency because they were going to digitize currency, make it easy to transfer money all around the world, very frictionless. All of that stuff was way over my head at the time. My first interview was with Peter at a Hobie's Restaurant in Palo Alto, California.

• 18:08Tim Ferriss?

  Just for those who don't know, so Hobie's back in the day was a famous meeting place, famous deal making spot. There are a handful of these and there's one in Woodside also, you know, the handful of these spots, but Hobie's, God, it brings back the memories, sorry to interrupt.

• 18:27Speaker 01

  No, it's okay.

• 18:27Tim Ferriss?

  That is where Mike and I used to meet for lunch to talk about this kind of stuff.

• 18:32Speaker 01

  There you go.

• 18:33Tim Ferriss?

  So wow, Hobie's, haven't thought about that. Okay, so you guys meet at Hobie's?

• 18:36Speaker 01

  So we meet at Hobie's. I'm wearing the company T-shirt that I got from a buddy on campus. He thinks that's pretty hilarious and he's telling me all about his background and Confinity's plans. And again, a lot of it's going over my head, but it sounds very cool and very interesting and he's very nice. And then I casually mentioned that I had traveled around Europe the prior summer with my girlfriend and I had taken a backpack full of books to read. And then he's like, well, what were the books? And then that's all we talked about for the entire interview was what books I had read, what did I learn from them, what was interesting from them.

• 19:15Tim Ferriss?

  What were some of the books?

• 19:16Speaker 01

  I think one was of Mice and Men. There was a bunch of Hemingway books. I remember that. I remember I read The Art of War. I remember I read The Tao Te Ching. So it was a pretty eclectic mix of different things that I had just accumulated. People said, oh, you should read this book. Oh, you should read this book. And I had a list of them. And before I left for my trip, I went to a used bookstore and bought a whole bunch of them.

• 19:42Tim Ferriss?

  It's an eclectic portfolio of books.

• 19:45Speaker 01

  Yeah, it was. It was. It was interesting.

• 19:47Tim Ferriss?

  Of the books?

• 19:47Speaker 01

  A lot of train rides in Europe.

• 19:49Tim Ferriss?

  Yeah. Of the books and the train rides, was there any particular, at that point in your life, that had stuck with you for any particular reason or that was memorable?

• 19:58Speaker 01

  The Hemingway books really stuck with me for a while. I can't recall exactly why because it's been some time, but maybe just the imagery, the way he was writing, what he was writing about, like Bullfighting in Spain and things. It was really, and I was probably reading that while I was on a train in Spain.

• 20:16Tim Ferriss?

  Totally.

• 20:16Speaker 01

  So there was something about that whole thing. The Art of War was definitely kind of fascinating as well. There were others. I'm sorry, I can't remember more.

• 20:24Tim Ferriss?

  No, that's fine. Hemingway, I'm just getting about to step back into Hemingway after a hiatus of 10 plus years for a whole bunch of reasons. I'm going to be spending more time in Africa and want to read a number of his books, but he's one of these sort of victims of his own success. I mean, in more ways than one, certainly, but you know, it's, he became so popular that he became unfashionable among critics, but he also won the Nobel Prize for literature. I think he was really, really good in so many respects and then got widely copied. So it seemed less unique, maybe once factoring in the many copycats who followed. But at the time, incredible storyteller and certainly maybe better modeled as a writer

• 21:08Tim Ferriss?

  than as a lifestyle.

• 21:10Speaker 01

  Sure.

• 21:11Tim Ferriss?

  Potentially.

• 21:11Speaker 01

  You know.

• 21:13Tim Ferriss?

  The newsletter, I just want to piece together a few things. So you get an email about this job opening.

• 21:18Speaker 01

  Yeah. So I'm part of something called BASIS. It's the Business Association of Stanford Engineering Students. They have a one credit, or I'm pretty sure it was one credit seminar on Friday afternoons where they bring in speakers from Silicon Valley, mostly business leaders. So I signed up to get this one credit and I was attending these, you know, Friday afternoon lectures essentially. And then there's a mailing list associated with that. And so that's where I got this.

• 21:47Tim Ferriss?

  What was the job position?

• 21:49Speaker 01

  Financial analyst.

• 21:50Tim Ferriss?

  Financial analyst?

• 21:52Speaker 01

  Yes.

• 21:52Tim Ferriss?

  All right. So you ended up, how were you notified that you got this job?

• 21:58Speaker 01

  So I have my breakfast with Peter. We talk about the book. I jokingly say, I must have read the right books because I get an email later that day, hey, great news. We'd like you to come in for some additional interviews. So I go in, I don't know, a few days later, I meet with a lot more people on the team. And then I get hired and I start working there, January 3rd of 2000. So this interviewing stuff happened in December. I start working in January. I mean, I have some fun stories from back then.

• 22:29Tim Ferriss?

  Well, I like fun stories.

• 22:31Speaker 01

  Well, one of the funny things, so back then, people could add money to their PayPal account in different ways. You could use a credit card, you could use a check, you could use a bank transfer and you could get your money out of PayPal in those same ways. And so, so back then, a lot of stuff was still manual. So at the end of the week, I would get a list spit out on a printer of checks that we had to write and I would go and I would type each one into QuickBooks and type in, you know, the name of the account, how much money. We had one printer in the office, so I'd have to go load the checks into the printer,

• 23:11Speaker 01

  call the CFO on his desk phone, maybe cellphone and tell him to hit print. Then he would sign them all by hand and then I would stuff them in envelopes and send them out.

• 23:23Tim Ferriss?

  Wow.

• 23:24Speaker 01

  Yeah. So that was, those were very early days. We had, I think when I started, we had about 14,000 PayPal users.

• 23:31Tim Ferriss?

  That's incredible.

• 23:32Speaker 01

  Yeah, it was crazy.

• 23:33Tim Ferriss?

  Do you have any idea? I don't, but do you have any guesstimate for at the end of your tenure, how many users there were, or even now, how many users there are? Do you have any idea?

• 23:42Speaker 01

  I don't remember. At this point, it has to be hundreds of millions.

• 23:45Tim Ferriss?

  It's a lot.

• 23:46Speaker 01

  Yeah, it's a lot.

• 23:47Tim Ferriss?

  It's a big number. This makes me want to recommend to folks, reading the first episode ever of Masters of Scale with Reid Hoffman, who also plays a role in this, in this whole story. Where he interviews Brian Chesky and they talk about doing things that don't scale in the beginning.

• 24:09Speaker 01

  That was something that didn't scale.

• 24:10Tim Ferriss?

  Yeah, doing a lot of things in the beginning that don't scale.

• 24:13Speaker 01

  Yeah.

• 24:14Tim Ferriss?

  And I'll leave it to people to listen to that, but you were in the office at that time. Who else is in the office with you?

• 24:23Speaker 01

  Peter's there, Max Levchin's there. There's probably, I think I was employee 34, so I don't want to list off 33 other people.

• 24:34Tim Ferriss?

  But names that people would recognize, much like we read in your, in your bio.

• 24:38Speaker 01

  Yeah, sure.

• 24:40Tim Ferriss?

  And was Reed around at the time?

• 24:42Speaker 01

  No.

• 24:43Tim Ferriss?

  Not yet.

• 24:43Speaker 01

  Not yet. I don't think Reed was around yet. And Elon existed very nearby. So he had started a company called X.com and that company was in an office also on University Avenue in Palo Alto, but down the street.

• 25:01Tim Ferriss?

  Mm hmm.

• 25:02Speaker 01

  And so when I started at PayPal, the two companies had not combined yet.

• 25:07Tim Ferriss?

  So for those who just want to imagine a visual here, so University Avenue is like the downtown strip in Palo Alto. I mean, strip makes it sound a lot bigger than it actually is. Very beautiful. And if you travel down to one end, you're not that far from Palm Drive, which is this incredibly picturesque drive that leads you into Stanford campus with these immaculate palm trees sort of arching up over either side with the Rodin Sculpture Garden on the right-hand side. It's, it's truly

• 25:43Speaker 01

  It's pretty amazing.

• 25:43Tim Ferriss?

  An incredible sight.

• 25:44Speaker 01

  It's, it's about as sort of Stepford Wives, like Truman Show, as you can get, but it's

• 25:51Tim Ferriss?

  a beautiful place. I used to spend a lot of time there. What are some of the?

• 25:57Tim Ferriss?

  Lessons you learned or interesting practices that you observed with Peter?

• 26:03Speaker 01

  Well, one of the biggest things I noticed frankly with Peter, certainly with Reed, also with Elon over time, is that they were never only doing one thing at a time, which I thought was very interesting because I would have thought logically, oh, you're doing this thing, you focus on this thing and you do this thing. But for them, and this is now spanning, not just when I started, but I was at PayPal for about three years. So just kind of spanning that three-year timeframe, watching them, they always tended to be doing multiple things. And I feel like they got a lot of benefit out of doing that because they would be getting exposed to different ideas, or solving different

• 26:47Speaker 01

  problems, or meeting different people. There was just all this stuff that they were interacting with, and then they would bring that back with them into the PayPal office.

• 26:58Tim Ferriss?

  When you say different types of things or multiple things, so it wouldn't be two PayPal-specific things? Or would it just be two divergent things within the realm of possible things you could do? Or could you give an example?

• 27:09Speaker 01

  Well, like in Peter's case, he was, he had been running a hedge fund slash VC fund prior to PayPal starting, had met Max, Max had this idea, they decided that they were going to work on it together. Peter invested money out of his fund to help launch the thing. And he still had the fund on the side, you know, probably wasn't more, I shouldn't even guess what percentage of his time. It wasn't a lot, but he still had something else that got a little bit of his attention while he was building PayPal. In Reed's case, I don't remember in detail, but I mean, even if you just look at Elon today,

• 27:52Tim Ferriss?

  Sure.

• 27:52Speaker 01

  You know, he has

• 27:54Tim Ferriss?

  Busy boy.

• 27:54Speaker 01

  Yeah, super busy. Well, even busier, I guess, the last couple of weeks. But even rewind 10 years, if he just had SpaceX and Tesla, I mean, those are two really big creations that he's working on. But I'm sure that he's pulling from one, you know, he's learning things from one that he's applying to the other. And so I think there's

• 28:14Tim Ferriss?

  There's a lot of transfer.

• 28:15Speaker 01

  Some benefit there, yeah.

• 28:17Tim Ferriss?

  You know, I'd read, let me just pull this up here, that Peter would give employees titles and levels of responsibility that reflected their potential, not their current ability.

• 28:27Speaker 01

  Mm hmm.

• 28:28Tim Ferriss?

  Could you elaborate?

• 28:30Speaker 01

  You know, I was on the receiving end of that. So I was at PayPal for about three years. Company goes public, then gets acquired by eBay. And five or six of us leave to go help Peter start his hedge fund again.

• 28:44Tim Ferriss?

  So this is Clarion?

• 28:46Speaker 01

  Clarion Capital, yeah. So he's going to go back to his fund, he renames it, and decides he wants to build this. This is going to be his next project. And so when I get there, this is pretty funny. So I'd worked pretty closely with Peter because I was on the, I was a financial analyst, and then I was the vice president of financial planning and analysis at PayPal. And so I was working a lot on the corporate financial model. When the company went public, that was kind of a cornerstone of the IPO roadshow presentation. And I got to go sit in on some of those meetings, which was really cool. But anyway, I got to work really closely with him. And so when I said I was interested to go over to Clarion, I didn't know what a hedge fund was, really.

• 29:30Speaker 01

  And he told me to read this book called When Genius Failed, which is about-

• 29:34Tim Ferriss?

  Oh, it's about long-term capital management?

• 29:35Speaker 01

  Long-term capital management. So that was, and then I thought-

• 29:38Tim Ferriss?

  Just some light inspirational reading?

• 29:40Speaker 01

  Yeah, just, I was like, I don't really know what hedge funds do. He's like, go read this book.

• 29:44Tim Ferriss?

  Yeah, great.

• 29:45Speaker 01

  So I read the book. And I was like, okay, now I have a rough idea what hedge funds do. And then I thought I had to read the Wall Street Journal every morning. And I was so diligent about that for a while. It was, and looking back, it's kind of comical, but I would just, I was like, this is my education. Like, this is how I'm going to do it. And so, and then I'm like, well, what should my title be? He's like, well, you should be the CFO. I'm like, I don't, I don't know anything about this. He was like, you'll pick it up quick. You know, he had a lot of confidence and faith, and we had worked together for, you know, pretty closely for a while by that point. And so I feel like that was a good example. You know, I think he was, he was thinking, where could I be, you know, in several years?

• 30:27Speaker 01

  If, if we stayed on some kind of trajectory, not what was my current ability at the time.

• 30:32Tim Ferriss?

  And is that something you've seen him do with other people in the sense that it's something? It's maybe easy for him to give because I'm just, I'm trying to imagine the thought process behind it. Because at least I've only met him a few times, but Peter strikes me as a very deliberate person in so many ways. What do you think the thought process is behind that? Is it that it's easy to give? If it doesn't work out, obviously, you know, the employment can always be terminated. So.

• 30:59Speaker 01

  Yeah, I don't want to speak too much for him.

• 31:01Tim Ferriss?

  No, I don't, not speaking for him, but if you were to speculate.

• 31:03Speaker 01

  Well, and because I know him is very thoughtful. I feel like he likes to invest in things that other people don't realize yet.

• 31:12Tim Ferriss?

  Sure, he's very good at it.

• 31:13Speaker 01

  And so he does the same thing with people. So he meets a person.

• 31:17Tim Ferriss?

  That's a cool way to look at it.

• 31:18Speaker 01

  He says, I think this person has potential that other people don't see yet. I'm going to take a chance and I'm going to maybe help cultivate that potential in them. So if you look over the course of his career, he's launched so many people off in different directions in different things. And I think that's why. And it could be, there's a lot, a lot of people ask like, what was it about PayPal? Why was it so special? There were so many other companies.

• 31:46Tim Ferriss?

  Now, meaning like the constellation of then largely unknown superstars? Or just what PayPal became itself as a company?

• 31:55Speaker 01

  The former.

• 31:56Tim Ferriss?

  Okay.

• 31:56Speaker 01

  Yeah, so why did the PayPal diaspora go off and start all of these amazing companies? Yelp, Yammer, Palantir, SpaceX, Tesla, YouTube? And I apologize to any of my PayPal friends if I'm leaving someone's company out.

• 32:15Tim Ferriss?

  It's really, it's just really insane.

• 32:16Speaker 01

  The list is just crazy.

• 32:17Tim Ferriss?

  Yeah.

• 32:17Speaker 01

  And people always ask the question, why was that the case? And I'm not sure there's one answer, but part of it could be the idea that there was a lot of latent talent in these individuals that had been identified by the people who were hiring them.

• 32:33Tim Ferriss?

  A lot of potential energy that people didn't see.

• 32:36Speaker 01

  Yeah.

• 32:37Tim Ferriss?

  Let's talk about that for a second. What did you observe, if anything, about the?

• 32:43Tim Ferriss?

  Hiring process, right? You came in at thirty something.

• 32:47Speaker 01

  Mm hmm.

• 32:47Tim Ferriss?

  And

• 32:48Speaker 01

  Thirty four.

• 32:48Tim Ferriss?

  Right, thirty four. And some of the names that people would recognize were not yet fixtures.

• 32:53Speaker 01

  Right.

• 32:53Tim Ferriss?

  At that point. What else did you observe about kind of team assembly? Whether it's at PayPal or at Clarion or elsewhere?

• 33:04Speaker 01

  So two things come to mind right away. One is hiring for general ability. And I'm not exactly sure how to say that, but as opposed to saying, does this person have the very specific skills to do this very specific job? It would be more focused on, is this person just exceptional in lots of different ways? Because if they are, they're going to be exceptional at whatever job they have to do. And a lot of my experience in a working environment is at startups.

• 33:39Tim Ferriss?

  Yeah.

• 33:39Speaker 01

  Where even Clarion Capital was a startup. It was a hedge fund, but it was a startup. And so you often have to wear different hats. You often have to switch context a lot. And you kind of just have to be a good all around utility player for some number of years until the organization scales to the point where you start hiring more specialized roles. So that was one thing, I think, hiring for like general capability as opposed to specific skill set. I think another thing, certainly at PayPal, was, and at Palantir to a large degree, people who didn't have specific experience in the industry that the business was in, which sounds very kind of counterproductive, not counterproductive, but

• 34:23Tim Ferriss?

  Counterintuitive.

• 34:23Speaker 01

  Counterintuitive, thanks. So at PayPal, PayPal merged with X.com and X.com had a lot of former financial industry people. And over time, gradually, the executives from the PayPal team, who had no prior experience in the financial services industry, wound up ascending in the corporate, you know, culture and hierarchy. And I think possibly because they weren't weighed down by legacy ideas of how things should be done. It's done this way. Why? Because it's always been done this way. Whereas someone like Reid Hoffman would say, well, that doesn't make any sense. We should do it this way because this is the right way. And that served PayPal really well.

• 35:09Tim Ferriss?

  For people who are interested, I love Reid. I've spent a bit of time with him and he's been on the podcast. And if I remember correctly, at some point, Peter would refer to him as firefighter in chief.

• 35:20Speaker 01

  Yeah.

• 35:21Tim Ferriss?

  And I mean, Reid is so composed. He's just, every time I see him, he's got this big smile. He's very calm, but just the amount, like the volume of problems that needed to be solved.

• 35:36Speaker 01

  Oh, yeah. No, he is a force of nature.

• 35:38Tim Ferriss?

  So incredible.

• 35:43Tim Ferriss?

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• 36:26Tim Ferriss?

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• 36:59Tim Ferriss?

  You've mentioned a name a couple of times now that I'd love to shift to. For people who know it and for those who don't, because I'm sure a lot want Palantir. So Palantir is a very interesting company. How did you end up at Palantir? And what does Palantir do?

• 37:16Speaker 01

  So I was at Clarium Capital, Peter's hedge fund. And at the time, he and four other people co-founded a company called Palantir. And that's how I found out about it. So Peter invested in it. And while I was at Clarium, we were also, me and others, were helping Peter build a family office. And so we were starting to manage some of his investments. Manage just means he had breakfast with someone, agreed to invest in their company, and then would send an email to us and say, hey, make it happen. And so we would do those things. So that's how I first met the CEO of Palantir. That's how I first found out about the company. I was super excited about it right from the beginning.

• 37:57Speaker 01

  And what the company does is uses, and you know, Palantir as a company is very...

• 38:07Tim Ferriss?

  Secretive?

• 38:07Speaker 01

  Secretive, yeah. And has a low profile. So I want to be really respectful of that.

• 38:14Tim Ferriss?

  Sure, yeah. And we won't do the unauthorized investigative journalism piece, but just so people have an idea.

• 38:21Speaker 01

  Yeah, so at a high level, at the highest level, they help people who have really big, biggest of the big disparate data sources. Disparate meaning they've got data in silos all over the place. They help them bring that data together into one cohesive place so that they can extract insights out of that data. And the thing that we would talk about is it's not necessarily the answers. It's what questions can you ask of the data that really starts to define the value of that data? And so Palantir would pride itself on saying, we allow you to ask more and more interesting questions from your data.

• 39:05Tim Ferriss?

  I appreciate that answer, and I'm going to stand in for the audience who might want just a little bit more.

• 39:09Speaker 01

  Oh, sure.

• 39:11Tim Ferriss?

  Again, we're not going to spend a ton of time on this, but just enough. Vast technological capabilities, right? You have fantastic technologists and fantastic technology and platform that's been built. Is it fair to say that most of the customers are governments in some capacity or another?

• 39:25Speaker 01

  I think were, so certainly started out that way. But I know that they've made a lot of progress in diversifying their business lines into commercial spaces.

• 39:34Tim Ferriss?

  Got it.

• 39:35Speaker 01

  I couldn't tell you the percentage difference.

• 39:37Tim Ferriss?

  Yeah.

• 39:37Speaker 01

  So I think two percentages, there'd be like US versus foreign would be one question. And then government versus commercial.

• 39:44Tim Ferriss?

  Yeah.

• 39:44Speaker 01

  And I don't feel versed enough on, on the data today. But certainly at the beginning, the first customers were the US government.

• 39:53Tim Ferriss?

  Yeah.

• 39:53Speaker 01

  Who was really struggling, remember, this was not that long after nine 11. And one of the things that we learned from the nine 11 experience was that, yes, we had all of this data, but we couldn't do anything with it.

• 40:07Tim Ferriss?

  Yeah, it's not information, it's just data.

• 40:09Speaker 01

  It was just raw data. And so that was one of the reasons Palantir was, was formed, was to help with that problem.

• 40:16Tim Ferriss?

  I'm just deeply, and again, we're not going to fixate on this, but deeply fascinated by businesses, or people for that matter, who opt for low profile. I just, it's endlessly interesting to me, right? Like if you have, whether it's like a Daniel Day Lewis, who just like disappears for five years at a time, then comes out with this amazing movie and then disappears for another three or four years.

• 40:38Speaker 01

  I love that guy.

• 40:38Tim Ferriss?

  Or a business, whether it's a Palantir, or I'm not going to mention them because it would annoy the people involved, but some of these hedge fund shops, right? They're like little, well, I shouldn't say little, but there are certain quant shops especially that really do not want any publicity whatsoever.

• 40:56Speaker 01

  Right.

• 40:56Tim Ferriss?

  And it's because that is so contrary to, I think, the trends that exist and the social pressure that exists in this modern age, right? With social, with broadcasting. I find it deeply interesting, especially when very smart people are involved, because you kind of assume there are rational arguments for why they do it. So let's maybe segue from here. Think it makes sense to the title of the book. And we can use that as a tool for making a sort of scene shift here. So Silicon Valley porn star so far Silicon Valley has come up. Porn star has not come up.

• 41:41Tim Ferriss?

  So unless I'm missing something in the the resume on LinkedIn, I don't think that you had this like short stint in between undergrad and grad school.

• 41:51Speaker 01

  I did not.

• 41:52Tim Ferriss?

  Okay, so fact check accurate. Why porn star? And you can answer this in any way that you like, but just to give us an idea of why this wording.

• 42:04Speaker 01

  Yeah, sure. Well, it goes well together. No, it certainly gets people's attention.

• 42:10Tim Ferriss?

  Yeah.

• 42:11Speaker 01

  The name porn star came from my life coach. And we haven't really talked much about the book yet, but I went on this journey. And part of that journey was a realization that I was addicted to online porn. And after several years of trying to stop the habit and not being able to, I finally realized that I should tell my life coach this because maybe she could help me. And I told her and we started working on this as as part of my work.

• 42:52Speaker 01

  And she has this technique or tool where we would, we would say that a person has a lot of identities in their universe. And if something is happening in your life that you want to take a closer look at, you you might assign that behavior to a specific identity. And what it does is kind of takes it off of you. And so then you can look at it with a little less shame and maybe a little less judgment and say, hey, I'm not a bad person. This identity of mine is doing this thing that I don't like. Let's figure out why. And she called that identity porn star. And the first time she said it, we both laughed and it was funny.

• 43:37Speaker 01

  And then then the name stuck. And then. In subsequent coaching sessions, we'd get on the phone and she'd say, so how's PornStar doing this week? And just like the levity around it and her curiosity around it actually encouraged me to start sharing things that were otherwise would have been very embarrassing to share. And that was really what started a lot of my healing.

• 44:02Tim Ferriss?

  Let's roll back the clock and look at where PornStar enters stage left, in a sense. So when did you first recognize that you had addiction or any issues related to pornography?

• 44:21Speaker 01

  You know, it probably wasn't until 2013 or 14, when, when I felt like this might be a problem. I started looking at porn in 1997, I think, whenever I got my first laptop in college.

• 44:38Tim Ferriss?

  Sure.

• 44:39Speaker 01

  And I had an internet connection and it was super slow and it was, the pictures took a long time to load. That's when I started looking at porn.

• 44:49Tim Ferriss?

  Right.

• 44:49Speaker 01

  Online. And then I just continued. I just thought it was normal.

• 44:53Tim Ferriss?

  Yeah.

• 44:53Speaker 01

  Every guy does this, right? The volume of content is infinite, effectively. If you're immersed in it, you just feel like, oh, everyone's doing this. And so the problem for me turned out to be that it didn't just stop with the porn. And it was a little bit of kind of a, I say in the book, it was a gateway drug for me. So at some point, still images weren't good enough. Then it was, then video, download speeds increased and then there's video. Oh, that's good. But then at some point, even that wasn't enough for me. And then I started looking for hookups. And this is when I was in a committed relationship

• 45:36Speaker 01

  with my girlfriend, who's now my wife. And that is really when the snowball started to pick up steam. So it was one thing to look at porn, I felt, and maybe not tell my girlfriend about it. I mean, how many guys do that, right?

• 45:53Tim Ferriss?

  Right.

• 45:54Speaker 01

  Seems like a pretty-

• 45:55Tim Ferriss?

  Low percentage.

• 45:56Speaker 01

  I don't know about that.

• 45:58Tim Ferriss?

  Well, no, no, no, I mean, what I mean is it's a low percentage where like, hi, honey. How was your day? And you're eating burritos with your significant other and they're like, let me tell you the porn I looked at over my lunch break.

• 46:08Speaker 01

  That's low percentage. That's the low percentage. Yeah. So.

• 46:10Tim Ferriss?

  The number of our generation suffered through very slow, like you practically dial up speeds to download like a three second clip and you don't know what it's going to be. Think that's like near a hundred percent.

• 46:22Speaker 01

  Yeah, it's pretty high.

• 46:23Tim Ferriss?

  Yeah.

• 46:24Speaker 01

  And so it was one thing to keep that a secret and lie about that. But once I started hooking up with people in the real world.

• 46:34Tim Ferriss?

  Yeah.

• 46:34Speaker 01

  That kind of took it to a whole new level. And then I got into what I would refer to as a shame cycle.

• 46:41Tim Ferriss?

  Yeah.

• 46:41Speaker 01

  And I didn't know it then, and it took me a long time to figure that out and get out of it. But that's when that started.

• 46:48Tim Ferriss?

  Now, the, and I think you described this in the book, but did the hookups begin with your lease on your apartment expiring and prompting you to go on Craigslist?

• 47:05Speaker 01

  Yeah, that's, that's exactly right. So my apartment lease was going to expire soon. I went on to Craigslist to look for a new apartment. That's what everyone did back then in, in the Bay area. And I noticed this new, I don't know how new it was, but I had never noticed it before. There was a link in the personal section called casual encounters. Maybe it even had a little news sign next to it or something. I don't know. And I was like, oh, that's interesting. And I clicked on it. And it was just pages and pages of people looking for hookups.

• 47:36Tim Ferriss?

  Wild.

• 47:37Speaker 01

  Yeah.

• 47:38Tim Ferriss?

  Now, in retrospect, and maybe you knew this at the time, but what were the factors contributing to this behavior? If you want to.

• 47:48Speaker 01

  Yeah, absolutely.

• 47:49Tim Ferriss?

  Explore that in any way that makes sense.

• 47:50Speaker 01

  Yeah. I didn't understand it at the time. It took me a very long time to, to understand what was going on under the surface. And you know, this goes to kind of one of the major themes of the book, which is this idea that unhealed traumas from our childhood.

• 48:10Speaker 01

  Can really affect our behaviors as we grow into adults. So I believe we are all kind of programmed in our childhood. And then we go out into the wild and we experience new situations. And we compare the situation to our programming to figure out what we're supposed to do. This is a very adaptive human psyche development. I don't think any of that's controversial. And I had some traumas in my childhood that I didn't even really understand at the time were as traumatic to me as they were. The first was when my parents got divorced when I was young. I was four, five or six years old. My father moved away. And that, I think it affected me.

• 48:55Speaker 01

  You know, I didn't understand how it affected me until I was in my 30s. So it took a really long time. But I think whenever, again, I don't think this is super controversial to say, when a primary caregiver leaves, it is very difficult on a child. The second thing that happened for me was that my mother, once I got into about middle school age, it started a little bit before that, but sixth grade was my first awareness of it, really. She started battling with depression. And so she was in bed a lot, medicated. The medical community was really still trying to figure out what to do with depression and anxiety. Still are.

• 49:39Speaker 01

  I feel like they still are. But there was all these medications, Prozac, other things. And so when she was home, she was, she was kind of distant. You know, she was like either in bed or if she was awake and walking around, she was a little bit distant, maybe not fully there because of this medication stuff. And, you know, there were good times, but then there were not so good times. And I think that lasted pretty much through most of, all of middle school and most of high school. And, you know, those are formative years for kids. We're trying to figure ourselves out. And

• 50:21Speaker 01

  I think that affected me too. And I don't, I want to be really clear. And I say this in at the, towards the end of my book, I don't blame my parents for the things that I did as an adult. It's not their fault. I'm just showing the linkage between an unhealed childhood trauma that then maybe impacts your behavior as you get older.

• 50:44Tim Ferriss?

  If you don't mind, and you can feel free to decline, like when it was, when your behaviors later, right, so we're flashing forward, got to the point where you were like, wow, this is a problem. And I don't know if you did that on your own, or if it was someone pointing something out to you, but what did your life slash behavior look like?

• 51:07Speaker 01

  The moment where it really felt like I was kind of spinning out of control. Just rewinding a little bit, I'd been at PayPal for about three years, made some money, not that much, even by, by today's standards, certainly, but more than I thought I would see in, you know, my twenties.

• 51:24Tim Ferriss?

  Yeah.

• 51:24Speaker 01

  So I was still pretty young. And then I went to Clarium Capital, Peter Thiel's hedge fund, hedge fund did really well. And I made big bonuses. And I started investing that money in startups. So again, there's like more money flowing in, Peter's worth is climbing, and he's becoming more famous. And, and I was part of that group working for him. And so it felt like we were, you know, close to this guy who's becoming kind of a celebrity.

• 51:53Tim Ferriss?

  Yeah.

• 51:53Speaker 01

  In some ways. And then, you know, you mix in the money, and I feel like my ego just started to really grow and to swell. And then I went to Palantir, and then Palantir became kind of Peter's next big thing, a big Silicon Valley story. I'm the CFO. Anne-Marie and I invested a bunch of my bonus money from Clarium into Palantir early on.

• 52:16Tim Ferriss?

  Yeah.

• 52:17Speaker 01

  And so we were making a lot of money on paper. And my ego just was, was swelling. And I just, I thought I could do anything. I thought I deserved anything I wanted. And that was the first kind of peak of bad behavior where I was just spinning like a top. I just had lost all direction.

• 52:38Tim Ferriss?

  Now, if, if you don't want me getting into specifics,

• 52:40Speaker 01

  No, it's good.

• 52:41Tim Ferriss?

  Were you? Masturbating twice a day to pornography, was it a couple of times a week? Because it is common, right? And you pointed out when we spoke before you came here for this conversation, that a number of years ago, I had this blog post about the, I think it was no booze, no masturbating 30 day challenge. But you know, I've thought enough about this, realizing that it can become a crutch or a salve or a compulsion, that it's interesting to me.

• 53:11Speaker 01

  Yes, but I feel like I was way off the deep end relative to that.

• 53:16Tim Ferriss?

  Yeah, so let's, let's hear about it.

• 53:17Speaker 01

  So it went from, you know, I've already said it went from porn to Craigslist.

• 53:23Tim Ferriss?

  Yep.

• 53:24Speaker 01

  And then Craigslist at some point turned into online escort websites.

• 53:28Tim Ferriss?

  Yep.

• 53:29Speaker 01

  And then, you know, I had that kind of going on in the background in addition to porn.

• 53:35Tim Ferriss?

  Yep.

• 53:35Speaker 01

  And then I wound up meeting someone at an event and starting an affair.

• 53:41Tim Ferriss?

  Yeah.

• 53:41Speaker 01

  And that lasted for months. And so all of this stuff is happening. I don't even know how I had time for all of that.

• 53:47Tim Ferriss?

  Yeah, I was wondering.

• 53:49Speaker 01

  Yeah.

• 53:49Tim Ferriss?

  It's a lot of time.

• 53:50Speaker 01

  Yeah. Looking back, I don't know how I was doing that. I guess the way I was doing it was I completely disappeared on Ann Marie. I was just gone.

• 54:00Tim Ferriss?

  That's your wife?

• 54:01Speaker 01

  She's now my wife, yes. And, and actually, we were married at the time that these things were happening by then. And I was just gone, like in a different world.

• 54:12Tim Ferriss?

  At the time, what was the story you told yourself about those behaviors? In other words, was the self narrative, wow, I'm spinning like a top. This is out of control. I don't know what to do at that point. Or was the story different?

• 54:27Speaker 01

  The story was different. The story had evolved out of, in our relationship, I wanted to have sex more frequently than Ann Marie did. And at some point, it turned into like resentment that we're not having as much sex in our relationship as I want. And I'm a successful man and successful men go out and they get what they want. And so I am entitled to this thing that I want and I'm going to go out and get it because I deserve to. And that was the narrative I was telling myself in my head.

• 55:06Tim Ferriss?

  When did that change?

• 55:09Speaker 01

  It changed about six months after our daughter was born and I had disappeared on her and then our daughter was born, which of course very, you know, is a big event in, in any family and we were just far apart at that point and I could feel that at the time I blamed it a lot on how much I was working. But The distance, the feeling of Yeah, the distance and the feeling. I, I wasn't even, yes, I was doing these bad things, but they couldn't be contributing to the distance because she doesn't know about them. I mean, that doesn't make any sense. It sounds ridiculous when I say it.

• 55:52Speaker 01

  But that's the narrative that was playing in my head. And so about six months after our daughter was born, maybe seven months. We were so far apart, I felt like I either need to quit my job or I'm going to get divorced. It was that clear and I decided I'm going to quit my job and I don't want to get divorced. I'm going to quit my job. I'm going to try to, you know, turn this around and I started working with a marriage therapist. She started talking to a marriage therapist, then, you know, there was a, there were a bunch of different therapists in the mix and then I wound up finding this life coach.

• 56:33Speaker 01

  But there's actually, there's, there's another trigger there. So I quit my job. And I think I stopped in January of 2010. Then I was home and it took me a while to kind of detox and decompress from Palantir, which had been a very intense work environment. But after four or five months, we just weren't getting closer. And I started wondering like, what's going on here? And I, and I asked Anne Marie like, hey, I, I stopped working so I could be home so that we could try to reconnect. And she was like, you can't just expect me to go back to the way things were and I didn't really have a good thing.

• 57:18Speaker 01

  And it turned out that she was having an affair. And I kind of discovered that. And that was a big aha moment as well, kind of a big wake up call. And she had been in her affair for quite some time. And that was this huge kind of explosion that happened. And then she moved out and we separated and shared time with our daughter, split, you know, we each had her two or three days at a time. And we both started working with this life coach.

• 57:52Tim Ferriss?

  With the same woman?

• 57:52Speaker 01

  Same woman, yeah, which I know is unique and a little bit unusual, but it worked for us. May not work for everyone, but it worked for us.

• 57:59Tim Ferriss?

  Now, you met her first, this life coach?

• 58:02Speaker 01

  I did.

• 58:02Tim Ferriss?

  Did you, did you persuade Anne Marie to then use the same life coach?

• 58:09Speaker 01

  No, I called her. So I had been talking with a therapist for, I don't remember how many months, four to six months before I had my first session with this life coach.

• 58:20Tim Ferriss?

  And just so we have a name, this is Melissa?

• 58:21Speaker 01

  Her name's Melissa, yeah. And I went to my first session with her. And I felt like I got more out of one hour with her than I had gotten out of months of therapy, months of like what I would call traditional therapy.

• 58:37Tim Ferriss?

  Right.

• 58:37Speaker 01

  And I'm not trying to say that to say anything bad about the therapist I was talking to. I'm sure they're great and they did help me to some degree. But I got more out of that one hour than I had in months. And so I was so excited that I, when I got to the parking lot, I called Anne Marie. And we still had enough communication lines open for this. We were coordinating schedules for our daughter and things like that. And I said, I just have to tell you about this session I just had with this life coach. I didn't know what a life coach was. And I told her, and she said, wow, you got all of that out of one hour? It's like, yeah. She said, well, maybe I should see this woman

• 59:18Speaker 01

  too. I was like, sure, why not? And so then she started and then we just continued.

• 59:24Tim Ferriss?

  Now, how initially, and I know some of the details of this, did you meet Melissa? How did that come to pass?

• 59:32Speaker 01

  Yeah, so I had.

• 59:35Tim Ferriss?

  Divine intervention in the form of an EA?

• 59:37Speaker 01

  Yes, absolutely. So I had an EA when I was at Palantir.

• 59:41Tim Ferriss?

  Executive assistant.

• 59:42Speaker 01

  Yes, executive assistant, amazing woman, her name's Julie. A tremendous business partner for me when I was at Palantir. And she could see that things weren't right. So in this period, you know, she could see the things were not right, you know, because she was kind of intimately involved in things that were going on with me at work and

• 1:00:01Tim Ferriss?

  In the sense that she just with her daily constant interactions with you could just feel that something was off?

• 1:00:07Speaker 01

  Yes, exactly. She was like, are you okay? You know, and keep in mind, I'm CFO of this fast growing Silicon Valley company. I'm also have all this philandering activity going on on the side. Plus I have a newborn at home. I had a lot going on. She didn't know all of that, but she could just tell that I was like falling apart or fraying at the seams. It just, I was not healthy. And she was like, are you okay? I was like, I don't think I'm okay. I don't think I'm okay. Why do you ask? You know? And then she said, you know, there's this woman that I know who kind of helps people

• 1:00:50Speaker 01

  in times of crisis or transition and maybe you should talk to her. And that's kind of how that started.

• 1:00:59Tim Ferriss?

  Wow. What was the EA's name again?

• 1:01:01Speaker 01

  Her name's Julie.

• 1:01:02Tim Ferriss?

  So Julie gets chocolates, chocolates every year.

• 1:01:04Speaker 01

  She's awesome. Yeah.

• 1:01:07Tim Ferriss?

  All right. So there's this explosion.

• 1:01:11Tim Ferriss?

  There are discoveries. Now I should ask, when you learned about her affair, did you at that point share?

• 1:01:22Tim Ferriss?

  What you had been up to or were up to, or did that, did that not happen until later?

• 1:01:27Speaker 01

  I did not share what I was doing. And that made some of the things that happened much later all the more painful. But no, I didn't. I played the victim. I said, oh my gosh, my wife's having an affair. I told my sister, I told my parents, told my friends. Woe is me. Can you believe it? I just, I just, I had no idea. I would never expected her to do something like that. I mean, I just played into that whole thing. And that was one of the things Melissa called me out on in that first session.

• 1:02:00Tim Ferriss?

  Oh, in the very first session?

• 1:02:01Speaker 01

  Very first session. She said, you feel like, you know, because I'm telling her the story. I share this in the book. I'm telling her the story. And the whole time I'm telling her the story, I'm just expecting her to be like, oh, you poor thing. Oh, you know, wow, that's, you know, how does that make you feel? That sort of thing? So I'm like telling her bits of the story, waiting for this feedback that the rest of the world had given me, the sympathy. And I'm not getting any of it. And I'm like, okay, what's going on here? And she's like, and when I finally stopped talking, she's like, you feel like a victim. It seems like you have this victim thing going. I'm like, yes, I'm a victim. You know, very good. You're

• 1:02:41Tim Ferriss?

  Catching on.

• 1:02:42Speaker 01

  You're catching on. You're following me. And, uh, but little did I know that, you know, she was going to take that in the exact opposite direction. I thought it was going to go. It's like, yeah, no, you've created this for yourself. And I was like, how does she know? Or, you know, I think maybe my first reaction is, what are you talking about? You know, she's like, you've created the condition in your life for this to happen. And then later in the session, like, before you come back next week, I want you to write down all of your secrets. I was like, how does she know I have secrets? And it scared the shit out of me.

• 1:03:16Tim Ferriss?

  Yeah.

• 1:03:16Speaker 01

  And she was kind of on to me right from the beginning.

• 1:03:20Tim Ferriss?

  From day one.

• 1:03:20Speaker 01

  From day one.

• 1:03:22Tim Ferriss?

  So how did things then unfold? Because you've, you've come back together with your wife, but we're skipping some in between chapters. It's, you are both meeting with Melissa.

• 1:03:37Tim Ferriss?

  What are some of the key developments or moments in say, the, just making up a number here? Six months after you both start working with Melissa?

• 1:03:49Speaker 01

  Well, Anne-Marie was pretty clear that she did not want to end her relationship that she was in. That was, of course, very difficult to hear. And then I wound up starting to date. And I had a couple of dating relationships much.

• 1:04:04Tim Ferriss?

  And you were, when you say separated, were you geographically separate? Were you also divorced at that point?

• 1:04:10Speaker 01

  We were not divorced.

• 1:04:10Tim Ferriss?

  Got it.

• 1:04:11Speaker 01

  And we didn't know if we were getting divorced or not. And at first, there was this, I don't know if it's a cultural thing, but it's like, when something like this happens in a lot of relationships, the tendency is like, that's it, we're getting divorced.

• 1:04:24Tim Ferriss?

  Right.

• 1:04:25Speaker 01

  I don't remember where the advice came from. It could have been from Melissa. Certainly Melissa's advice was, don't make any big decisions for a few months. And I think that was kind of code for like, don't decide to get divorced. Don't completely change everything. Like, there's a lot of work to be done. There's a lot of work that has to be done.

• 1:04:43Tim Ferriss?

  Yeah, let's not go nuclear immediately.

• 1:04:44Speaker 01

  Yes, let's not go nuclear immediately. So we were separated and Marie moved out and had an apartment. It was not that far away, a mile away in San Francisco or something like that. And so we're talking to Melissa, let's say in that first six months. And most of the time it's separate. I'm pretty sure back in those days, most of our sessions were separate, although some of them were together. But really, we're, we're doing our own individual work. And one of the things that was interesting about it was we were learning a whole new vocabulary in the work that Melissa was doing. And we had to stay in touch because we were coordinating our daughter's schedule.

• 1:05:23Speaker 01

  And not to put too much pressure on her, but she really held us together during that time. Because if we didn't have her, I think we could have easily drifted in, in different directions. So because of her, it kind of kept our lines of communication open. And we would share sometimes, you know, something we might have learned in one of our sessions.

• 1:05:50Tim Ferriss?

  Here's a question, just on a, sort of on a technical level. And I'm asking because my girlfriend and I have also at times used the same, let's say therapist.

• 1:05:59Speaker 01

  Yeah.

• 1:06:00Tim Ferriss?

  And

• 1:06:02Tim Ferriss?

  The therapist, to his credit, set certain rules upfront in what could be shared or would be shared or would not be shared sort of across the solo sessions. Did you guys have any type of agreement, for instance, like that anything was on the table? So anything that came up in your session could be shared with Anne-Marie and vice versa? Or that nothing would be shared unless there was sort of explicit permission granted?

• 1:06:27Speaker 01

  The latter. Nothing would be shared unless there was explicit permission. That's changed now.

• 1:06:32Tim Ferriss?

  Yeah.

• 1:06:33Speaker 01

  But back then, you know, this whole thing had blown apart and we were not there.

• 1:06:39Tim Ferriss?

  For sure.

• 1:06:40Speaker 01

  Yeah.

• 1:06:40Tim Ferriss?

  No, I think it makes a hell of a lot of sense. I was just curious.

• 1:06:43Speaker 01

  Yeah. And Melissa might say, is it okay if I share this thing?

• 1:06:47Tim Ferriss?

  Right.

• 1:06:47Speaker 01

  And yeah, but we tried, she did encourage us to share with each other.

• 1:06:52Tim Ferriss?

  Can you give any examples of the shared vocabulary? I want to see if there's maybe a concept or language that you could give us as an example.

• 1:07:01Speaker 01

  Well, one of those would be this idea that, you know, like she told me, you're not a victim. You've created this situation in your life and I'm going to help you figure out why. Part of what's embedded in that is this idea that you are kind of responsible for everything that happens in your life. And so that would be a good example where in those first six months, yes, it was, the revelation was that Anne-Marie had been having an affair. I never came clean on my other behavior, but I started to at least take responsibility for my disappearances related to work.

• 1:07:43Tim Ferriss?

  Right.

• 1:07:43Speaker 01

  And having no boundaries around my work. And she, I can't remember details of what her side of that would have been. And I wouldn't, I wouldn't want to speak for her too much anyway.

• 1:07:55Tim Ferriss?

  For sure.

• 1:07:55Speaker 01

  Yeah. But that was one for me, this idea that. I am responsible and I need to take, I'm not a victim. I need to take responsibility for everything that's happening. And another vocabulary thing that came up during that time was this idea to simplify and subtract, which for me took on a whole lot of meaning. When I started my first VC fund, I named it Subtraction Capital. I was just doing way too many things and I needed to subtract and simplify. And I think Anne Marie had certain things in her work where she also had to subtract and simplify.

• 1:08:33Tim Ferriss?

  What type of work was she doing?

• 1:08:34Speaker 01

  When I said work just then, I meant her work with.

• 1:08:36Tim Ferriss?

  Oh, the personal work. I see. Right.

• 1:08:38Speaker 01

  Yeah.

• 1:08:39Tim Ferriss?

  Since this is, I literally have a little sign that I got when I was in Truckee at some point with this guy named Chris Saka, a great guy, good friend. And we went to a diner and there was, it was full of all these tchotchkes. And there was this hand painted sign that said, simplify. And I hack, like haggled and negotiated to buy this from this diner and put it in my house.

• 1:09:01Speaker 01

  Smart.

• 1:09:01Tim Ferriss?

  Which I have now.

• 1:09:02Speaker 01

  Smart.

• 1:09:02Tim Ferriss?

  I think sometimes I'm better at looking at it than I am at implementing it. But I'm curious for you, what were some of the meaningful subtractions that were made? And how did you choose what to subtract?

• 1:09:14Speaker 01

  I would say it's kind of like peeling an onion or something. It's just layers and layers and layers. Like, once you get on this subtraction mentality and mindset, or simplification mindset, you think you're simplifying and you go through and you, and you do a bunch of stuff. And then some months later, you realize, oh my gosh, now I'm going to start simplifying at a totally different level. I'll make this more tangible. So at first it was, so I had left Palantir and I couldn't detox immediately. Or like, I couldn't just cold turkey stop working. So I started trying to get all these consulting jobs.

• 1:09:49Tim Ferriss?

  Right, right. You couldn't go from sixth gear to first gear.

• 1:09:52Speaker 01

  Yeah, yeah. And I just, so. And I was scared that if I didn't keep working, I wouldn't be able to get another job when I was ready to go back to work, all these fears. And so I had to start doing less stuff. And so as those consulting jobs ended, I didn't get new ones. I started unsubscribing to all of the email newsletters that I was subscribed to. I didn't really, never watched a ton of TV, but I pretty much stopped watching TV entirely. And I got a lot more selective. I used to do lots of lunches and breakfasts and dinners. I don't know if it was just me, or if it was Silicon Valley culture, I'm not sure.

• 1:10:36Tim Ferriss?

  It's a lot of the latter, I think.

• 1:10:38Speaker 01

  Okay.

• 1:10:38Tim Ferriss?

  For sure.

• 1:10:38Speaker 01

  Yeah. And I was really wrapped up in that. And, and so I had to stop doing that stuff, too. That was another big thing that I kind of subtracted.

• 1:10:47Tim Ferriss?

  Now, what was your technique or go to language for that? You're just like, I'm sorry.

• 1:10:54Speaker 01

  Yeah.

• 1:10:54Tim Ferriss?

  Consider me dead for the next two months, or was it, I'm sorry, I have a conflict. Can't, can't make this work.

• 1:11:01Speaker 01

  Nothing blanket. It was always just like a one off thing, like, sorry, I can't make it. Or, you know, frankly, I think I was the one doing a lot of the fighting back then.

• 1:11:11Tim Ferriss?

  Interesting. Okay, right. You were doing a lot of that.

• 1:11:13Speaker 01

  Cause there was like a badge of honor. It was like all these lunches and dinners and breakfasts. I'm so busy. Look how important I am. Oh, I'm so amazing. And, and so I just kind of had to stop, just stop, period, and be more still. And that's hard to do.

• 1:11:30Tim Ferriss?

  How did Melissa sell this to you?

• 1:11:35Speaker 01

  Yeah. She said, you're efforting your way through life. And I was just livid.

• 1:11:46Speaker 01

  I was like, what are you talking about? You know, I have gotten where I am because I work so hard. I was never the smartest kid in my classes. I was not the smartest person at PayPal. I was definitely not the smartest person at Clarion. I got where I was because I hustled my butt off. I just worked really hard. And so for her to say, you're efforting your way through life was like, your whole strategy is wrong. You know, hitting me in the core. And I remember one time she was telling me this and I was like, well, I can't just sit on the couch and meditate monks don't have mortgages. And then she cracked up. I should have gotten a T-shirt with that on it monks don't have mortgages.

• 1:12:28Speaker 01

  But that was how I felt. It was like, I don't know what the spiritual stuff is you're talking about. I can't meditate. I don't have time to meditate. I've got bills to pay. And so she said, you're efforting your way through life. I promise you, there's a way to create just as much abundance in your life, if not more, with much less effort. And once I got through the fireworks of disagreement, I still didn't believe her. I was like, yeah, sure, whatever.

• 1:12:58Tim Ferriss?

  Yeah.

• 1:12:58Speaker 01

  But also, I really wanted to save my marriage.

• 1:13:01Tim Ferriss?

  Yeah.

• 1:13:02Speaker 01

  And I didn't want to lose my daughter or just be in half of her life or whatever the arrangement would have been. And so I was willing to try it and say, okay, let me try it. And I did. And I started subtracting.

• 1:13:18Tim Ferriss?

  Is there a particular process that she uses to aid you with that subtraction? Or is there, are there any filters you apply? Or is it, are you just turned loose with the instruction to subtract?

• 1:13:33Speaker 01

  What I recall from then, it's a little fuzzy because it was a long time ago. But one of the things I recall was this idea that she taught me that our default state, she wouldn't use that language, but in my words, our default state is peacefulness. Our default state is happiness. You know, you would say that kids are really good at reading people's energy. They're really good at assessing like if someone's safe or not, animals have this sense. Why do they all have this sense, but adults don't? Like, what did we do? We, we put layers and layers of stuff around that core.

• 1:14:16Speaker 01

  Part of ourselves, that intuition and that in order to get back to that place, that like default state of peacefulness or happiness or being in tune with others, we had to start peeling away those layers around the outside. We had to start subtracting those layers. And so that was part of the conversation. And so it was, well, just look around your life for things that aren't serving you anymore. Could be a relationship, it could be a job, it could be a habit, could be whatever. If it's not serving you and it's not making you happy, get rid of it. So happiness isn't something you find, it's what's left when you get rid of all the things that make you unhappy.

• 1:15:00Tim Ferriss?

  Right. Just sitting with that for a second. Yeah, I like that. It's just removing all of the detritus and rust and nonsense that is gathered around.

• 1:15:15Speaker 01

  Yeah.

• 1:15:16Tim Ferriss?

  What is the sort of default core?

• 1:15:18Speaker 01

  Yeah.

• 1:15:20Tim Ferriss?

  Let's introduce an acronym, SA, not South Africa, Sexaholics Anonymous in this case. Where did that enter the picture and did it enter the picture before or after you came clean with your wife about sort of your side of things?

• 1:15:39Speaker 01

  Her fair revelation comes in early 2010. We're separated for a while. I never reveal what's going on with me. We get back together after about a year and a half and I'm on good behavior for a while, but then I start in with the bad behavior again. And in 2014, something happens where I kind of sort of get caught, but I'm able to say, this never happened before, it'll never happen again. And then in early 2015, I get caught again, and this time she doesn't believe me, Melissa doesn't believe me. At that point,

• 1:16:20Speaker 01

  I have come clean with Melissa about porn. It had been about a year that I was saying, like, I want to work on this porn habit. I don't think it's helping me. I think I need to get rid of it. I think I need to subtract it. And so I get caught in early 2015 and it's pretty devastating because after everything Anne-Marie and I had been through.

• 1:16:43Speaker 01

  It was like she just started feeling like, I don't even know this person. Who is this person? Is there something he's not telling? And Melissa understood it too. And I'd kind of spiraled again into a place where I felt like I had kind of lost control of my life. And she said on the phone to me one day.

• 1:17:08Tim Ferriss?

  She being?

• 1:17:09Speaker 01

  She be Melissa.

• 1:17:09Tim Ferriss?

  Awesome.

• 1:17:10Speaker 01

  You know, we don't believe you. And if you don't share your secrets, you'll stay sick. And if you want to move forward, you're gonna have to share your secrets. And that's when I finally came clean. That's when I kind of, the floodgates opened. And I said, okay, it's not the first time this has happened. Said, how many times has this happened? I said, I can't even count. I don't know. How long has this been going on? Since I can remember, it'd been going on for a very long time by then. And I started crying and said, I have a serious problem and I don't know how to stop and I don't know what to do.

• 1:17:52Speaker 01

  And she was the one who suggested I check out a 12-step program. And that's how, you know, a few nights later, or maybe even that night, I remember, I started researching 12-step programs for sex addiction. And found myself on the Sexaholics Anonymous website, reading the material and just shocked at how accurately it described my life.

• 1:18:18Tim Ferriss?

  And place us in time then, that was roughly when?

• 1:18:22Speaker 01

  That was February of 2015.

• 1:18:25Tim Ferriss?

  What is your participation looked like or attendance? I'm not sure the right term to use.

• 1:18:31Speaker 01

  Sure.

• 1:18:31Tim Ferriss?

  Since then?

• 1:18:32Speaker 01

  Since then. So I attended, at the beginning, I attended meetings, several meetings a day for weeks, trying to find a meeting and a place and a group of people that really resonated most with me. And frankly, it was a lifeline for me because when I revealed this stuff. You know, I had to move out.

• 1:18:53Tim Ferriss?

  Yeah.

• 1:18:53Speaker 01

  Again, it was very devastating and I was very lost and very scared. And SA became kind of a lifeline because it was a group of people who were suffering through the same thing that I was suffering through. And so I was there several times a day at the very beginning. That settled into, you know, a few meetings a week. And I probably did that for a year or a year and a half. And then our family moved in 2017. We moved to Singapore for six months for my work and I stopped going to meetings. And then when I came back, I didn't pick it up again. And I, I feel okay with that.

• 1:19:36Speaker 01

  The biggest things I took away from the experience. So there's kind of two things that I want to remark there. One, the biggest thing I took away was if I live a life of humility and with love for myself and compassion for others, I will have a good life. I don't need to worry about anything else. Like if anyone gets to a really, really bad, dark place, if you focused on those three things, you can climb out of that.

• 1:20:06Tim Ferriss?

  One more time, can you repeat those?

• 1:20:09Speaker 01

  If I live a life of humility, of love for myself and compassion for others, you can get through just about anything, I think. And so this concept of surrendering, I mean, that's the humility piece.

• 1:20:23Tim Ferriss?

  Right.

• 1:20:24Speaker 01

  Was just so helpful and so important.

• 1:20:28Tim Ferriss?

  You said there were two pieces.

• 1:20:29Speaker 01

  Yes, there were two pieces. And at this very moment, I can't remember the second piece. I'm so sorry.

• 1:20:34Tim Ferriss?

  No, that's okay. It's okay. We can come back to it.

• 1:20:37Speaker 01

  Yeah.

• 1:20:37Tim Ferriss?

  So let's think about this. So I was asking you about your participation and attendance since 2015. We flash forward, Singapore due to work, came back. You didn't pick it back up, but I feel okay with that.

• 1:20:49Speaker 01

  I feel okay with that. And now I remember the second thing.

• 1:20:51Tim Ferriss?

  That was my intention.

• 1:20:52Speaker 01

  Yeah, thanks for the reminder. So I feel like these addiction topic is a, it's a huge topic, right? We could have talked for an hour just about that.

• 1:21:02Tim Ferriss?

  Oh, yeah, many hours.

• 1:21:04Speaker 01

  And.

• 1:21:06Speaker 01

  I feel like, having gone through that experience, and so I often ask myself, I feel like the cultural narrative, a lot of times with addiction is, you know, once an addict, always an addict. And it becomes this label that you label yourself for the rest of your life. I'm not sure how I feel about that. The way I've thought about this is, in my experience, what led me into that addictive cycle was shame. And I feel like if I had to label it with a different word, I would call it a shame cycle. So there's some kind of core shame that happens. And then we go do some kind

• 1:21:50Speaker 01

  of behavior to distract ourselves from feeling that shame, so we don't have to feel it. We do some kind of behavior that maybe isn't good. We feel ashamed of that behavior. Now there's more shame. Now we go back, we act out again, so that we can distract ourselves, you know, and avoid feeling that shame. And you get into this cycle, and it just piles on. And I think that this is what we have come to term an addiction. I do feel like it is possible, with internal work, to go back and understand all of the layers of shame, and eventually get back to understanding the root cause of shame,

• 1:22:31Speaker 01

  and really actually break that addictive shame cycle. And I would, I would build on that also, just having spent some time looking at different modalities for treating various types of addiction. I would say that there's the shame spiral, and there's also a sort of pain shame spiral, right? Where, as a doctor named Gabor Maté would talk about asking why, not why the addiction, but why the pain. So people using, there's certainly sort of a shame on shame spiral, as you described, which is the first time I've heard that described. And I think it absolutely would resonate with a lot of people listening who experience this. And then there's the sort of pain.

• 1:23:12Tim Ferriss?

  Escape or numb the pain?

• 1:23:15Speaker 01

  Mm hmm.

• 1:23:15Tim Ferriss?

  And then the shame subsequent to using a coping mechanism that is not

• 1:23:22Tim Ferriss?

  good in quotation marks, or that is bad in quotation marks, that is not socially acceptable, like heroin use, for instance, could be anything else. I mean, there are a million different ways. It could be an eating disorder. It could be, you name it.

• 1:23:33Speaker 01

  Mm hmm.

• 1:23:34Tim Ferriss?

  And I agree with you and not a therapist, not an M D. I don't play one on the internet, but I do believe that you can, with the proper guidance and tools, in many instances, maybe not all, but go back, identify the root, kind of kernel, causes that you're describing.

• 1:23:56Speaker 01

  Mm hmm.

• 1:23:57Tim Ferriss?

  And then metabolize or recontextualize or somehow contend with those in such a way that you remove like the initiator in that first piece of the chain.

• 1:24:07Speaker 01

  Mm hmm.

• 1:24:08Tim Ferriss?

  So now you're describing these meetings, 2016, you're in Singapore. At that point, are you still?

• 1:24:16Speaker 01

  2017.

• 1:24:16Tim Ferriss?

  Seventeen?

• 1:24:17Speaker 01

  Seventeen.

• 1:24:18Tim Ferriss?

  So 2017, at this point, are you guys still apart?

• 1:24:21Speaker 01

  No. So we, so I move out in early 2015, February, and I go into this really intensive retreat. So I'm living by myself. I shut down most of what I'm doing for work. I just do the, like, the bare minimum stuff that I need to do to keep the, it's a V C firm, to kind of keep things moving forward. I have to share what's happening with my business associates, which is incredibly embarrassing. And so I shut down as much as I can. And I start reprogramming myself, I guess. I, I start journaling very intensively. So I'm

• 1:25:01Speaker 01

  going to essay meetings, you know, at least a few times a week. I'm journaling very intensively. I stopped lifting weights at the gym. I start going to yoga several times a week. Actually, I mean, sometimes it was twice a day. I stopped eating meat. I stopped drinking alcohol. I just changed everything. I go to bed when it gets dark and then I Wake up when it's dark and I journal to candlelight.

• 1:25:23Tim Ferriss?

  Monks do have mortgages.

• 1:25:24Speaker 01

  Monks do have mortgages. Yes, and Melissa joked that at some point during that retreat that I was on, she's like, I'm not going to call you porn star anymore. And now you're the monk. And I really was living this kind of monkish life. I was just tuning everything out, only reading like spiritual books. Autobiography of a yogi was one of them. More stuff, books by Emmett Fox.

• 1:25:49Tim Ferriss?

  I don't know Emmett Fox. I probably should.

• 1:25:51Speaker 01

  Oh, yeah. I like him a lot.

• 1:25:53Tim Ferriss?

  Any, any starting point?

• 1:25:55Speaker 01

  I like The Sermon on the Mount, and there's also a book called The Lost Booklets of Emmett Fox. The biggest thing I take away from, from Emmett Fox is this, just reinforcing this idea that what is happening in your life situation, or in your external universe, as, as Anne Marie and I would say, is only a reflection of what is happening in your interior universe or inside yourself. And so that became very important to me at that time because I had to change. I was running off the programming or, or I was in a shame cycle, however you want to describe it. You know, the society had told me I needed money, cars and women to be happy and successful.

• 1:26:38Speaker 01

  So I thought I should go out and get those things. And then I was miserable. Like, all of these things were crashing down and I had to change my life. And he was telling me, in addition to Melissa telling me, you have to change inside yourself first.

• 1:26:53Tim Ferriss?

  So Melissa was still engaged at this point?

• 1:26:55Speaker 01

  Yes. I still talk to Melissa every week.

• 1:26:58Tim Ferriss?

  Right. And during this ascetic, sort of reclusive, I don't want to say reclusive, but that's not fair. Retreat phase.

• 1:27:06Speaker 01

  Yeah.

• 1:27:06Tim Ferriss?

  You were still engaged with her on a regular basis?

• 1:27:08Speaker 01

  On a regular basis. In fact, every time she had a cancellation, she would text me and I didn't have anything else to do except work on myself. And so I would take it. So I had several coaching sessions a week.

• 1:27:20Tim Ferriss?

  During that period, I'm very interested in the things that worked. I'm also wondering, were there any dead ends? Like you try, anything that you tried where you're like, actually, this is counterproductive? Because you changed a lot of things.

• 1:27:33Speaker 01

  I changed everything.

• 1:27:34Tim Ferriss?

  Yeah.

• 1:27:35Speaker 01

  I changed everything. I changed my diet. I changed my sleep habits. I changed my workout habits. I changed the people I talked to, the work I did. I changed everything.

• 1:27:44Tim Ferriss?

  Let me ask a question that comes to mind. How much of that, if any, was? Consciously or subconsciously, a desire and a renewed ability to look at yourself differently. Does that make sense? Like Bill sort of allowing you to regain maybe confidence or self-respect so that you could do the work necessary, right? When you change so many things, when you change everything, you're basically unrecognizable.

• 1:28:10Speaker 01

  Right.

• 1:28:11Tim Ferriss?

  Compared to the person that you were, behaviorally speaking.

• 1:28:15Speaker 01

  I felt like it was out of necessity that I had been living with this set of beliefs of what would make me happy. I had been lying. I was full of shame. I was in danger of my career was at risk because I was taking bigger risks with what I was doing in terms of the philandering and stuff. And I was probably risking my health. I was probably risking my safety. I was definitely risking my marriage. Like, everything that I cared about was at risk. And so I think I just didn't want to lose it all.

• 1:28:53Tim Ferriss?

  And that was 2000.

• 1:28:55Speaker 01

  It was early, early 2015.

• 1:28:57Tim Ferriss?

  Early 2015. At what point, so I just have some notes here. These are, these are from your book. Two books, The Seed of the Soul.

• 1:29:04Speaker 01

  Hmm.

• 1:29:06Tim Ferriss?

  And then that first one is Gary.

• 1:29:10Speaker 01

  Zukov.

• 1:29:11Tim Ferriss?

  Zukov. And then Healing the Shame That Bind You.

• 1:29:14Speaker 01

  Yeah, so those, those came in later. I would say another book that was really instrumental when I was in the deepest part of my journey was Love Warrior by Glennon Doyle. So, I mean, and I read so many books during that time, but the ones that really stuck out were Autobiography of a Yogi, Emmett Fox's books, and Glennon Doyle's book, Love Warrior. And Love Warrior, you want me to tell you?

• 1:29:41Tim Ferriss?

  Please.

• 1:29:41Speaker 01

  Yeah, Love Warrior.

• 1:29:44Speaker 01

  Glennon, you know, if you haven't read the book, she just shares her story and is very vulnerable. And I was in a very dark place and trying to figure out like, how did this happen to me? How did I get here? And there's some themes of that in her book as well. And it just really helped me feel less alone. And like, there was some kind of path that I could take to get out of this. How did you end up coming back together with Anne Marie? So during that time, you know, she, at first, I thought we were getting divorced.

• 1:30:24Speaker 01

  Like, I just thought there was no way we're going to recover from this. And Melissa said, "Hey, Anne Marie, if you were engaged in this co-creation with Jason for so long, you must have been getting something out of it. You created this in your life, and I'm going to help you figure out why." It's the same message, right? The message is the same for everyone. And she recommended a book to the two of us called Women Who Love Too Much by Robin Norwood. I've heard a lot about this book. I've never, I've never read it. It's a great book. Yeah. And in that book, she talks about how women who are in families with an addicted

• 1:31:07Speaker 01

  parent, and Anne Marie's father suffered with alcohol and drug addiction when he was younger, when she was younger and he was younger, and they tend to get into relationships with other addicts or people who are not emotionally available in some way. And, you know, addiction definitely does that to a person. And so, as odd as it sounds, it was a very comfortable place for Anne Marie to be with a guy who was not fully emotionally present. Because if I had been fully emotionally present, it would have been very uncomfortable. Unfamiliar. Unfamiliar and uncomfortable. And so, we read that book, and it really...

• 1:31:53Speaker 01

  Changed the way we thought about everything that was happening. And she started to understand this as well. But she was also, she also got very clear, you know, with her boundaries. Like, you need to fix this. You need to climb out of this. I understand you're on a journey. I understand you have work to do. But if I ever feel like you're not working and you're not taking this seriously, then we'll get divorced. It was that clear. And I was like, yes, ma'am. Like, I am going to do this. And I really wanted to get well. I didn't want to lose her and I didn't want to lose my daughter.

• 1:32:29Tim Ferriss?

  When did Melissa reach out to Anne Marie? Or were they also having an ongoing?

• 1:32:36Speaker 01

  Ongoing, oh, yeah. When I started way back in 2010, when I started working with Melissa, Anne Marie started working with her around the same time. And we both still talk to her on a weekly basis. So she was, during that time, we had a lot of joint sessions during this time in early 2015. And then by August of 2015, we came back together. So I was only on retreat. It seems like a short amount of time. It was for four and a half months, but it was really intense and it felt like a very long time. And we both changed a lot during that time, me a lot more than Anne Marie.

• 1:33:15Speaker 01

  And we came back together and have been together ever since and it's been beautiful.

• 1:33:22Tim Ferriss?

  What have been some of the most important keys to the repair process? Repairing trust in both, in both directions?

• 1:33:34Speaker 01

  Right.

• 1:33:34Tim Ferriss?

  But particularly after getting back together, after the retreat, are there particular things that come to mind when I ask that?

• 1:33:44Speaker 01

  Yeah, it took a long time. You know, more for her to trust me again.

• 1:33:49Tim Ferriss?

  Yeah.

• 1:33:51Speaker 01

  It took time. It just took time.

• 1:33:52Tim Ferriss?

  I can imagine her also just being, not just distrusting at various points, but also really pissed off.

• 1:33:59Speaker 01

  Yeah.

• 1:33:59Tim Ferriss?

  That you had, and I'm not casting judgment here, but that you had kept your secrets while condemning her.

• 1:34:07Speaker 01

  Absolutely. That was horrible. It was just horrible thing for me to have done. That's what made it so devastating.

• 1:34:14Tim Ferriss?

  Yeah. Were there any particular steps or any particular conversations?

• 1:34:21Tim Ferriss?

  You know, aside from time healing all wounds, right? Which, which may or may not be true. Maybe deliberate practice heals a lot of wounds. But what were some of the things that helped?

• 1:34:29Speaker 01

  Yeah, and, and to your point about healing wounds, Anne Marie has said this, and I thought it was kind of a lovely way to put it, or an interesting way to put it, that yes, time heals those wounds, but you still have scars.

• 1:34:42Tim Ferriss?

  Yeah.

• 1:34:43Speaker 01

  You know, we still know what happened. And it's all been part of our journey. And we appreciate everything that our journey has taught us. But those things still happened and they were still painful.

• 1:34:54Tim Ferriss?

  What safeguards do you put in place? I'm just imagining, there's ubiquitous, high-speed Wi-Fi everywhere.

• 1:35:03Speaker 01

  Mm hmm.

• 1:35:03Tim Ferriss?

  You have laptops, right? And if pornography on some level is like the gateway drug that opens Pandora's box.

• 1:35:10Speaker 01

  Mm hmm.

• 1:35:11Tim Ferriss?

  What are some of the rules and

• 1:35:15Tim Ferriss?

  parameters or guide rails that you have for yourself?

• 1:35:20Speaker 01

  Nothing technology related. So I don't have special filters on my phone or anything like that. So I went, so 2015, this whole thing blew open. I moved back in kind of mid-year, let's say August, late summer. I went two full years without looking at porn at all. I didn't even think of it. I think one day I woke up, I was like, oh, my gosh, it's been six months since I looked at porn.

• 1:35:42Tim Ferriss?

  Yeah.

• 1:35:43Speaker 01

  Well, actually, in the very dark first period, it was, it was hard. But anyway, at some point, it was like, it just disappeared. It was off the radar and it was, I didn't have special filters on my phone. I just never went into it. And then I don't remember what happened, but I got kind of called back to it. But this time I was really open about it with both Melissa and Anne Marie. Said, hey, this interesting thing happened. I wanted to look at porn again. And so that was interesting. And in my conversations with Melissa, it was like, this thing is here to teach you something. If you're going to engage with it, you need to get curious.

• 1:36:26Speaker 01

  How am I feeling when this is calling me? How am I feeling when it's happening? How do I feel afterwards? And as I started to get more curious about it, that's essentially like turning the lights on. It's not fun when the lights are on.

• 1:36:40Tim Ferriss?

  That's very, yeah, no.

• 1:36:44Speaker 01

  Takes all the fun out of it.

• 1:36:45Tim Ferriss?

  Yeah, de-sexifies the process.

• 1:36:46Speaker 01

  Absolutely. And so, so it has been that process. So it, you know, it's been a long time since it's come knocking. I would be lying if I said it has never, that it never came knocking again. I would say probably on average, once or twice a year.

• 1:37:03Tim Ferriss?

  Yeah.

• 1:37:03Speaker 01

  Something happens, but when that happens.

• 1:37:05Tim Ferriss?

  Birthday, morning of the birthday?

• 1:37:07Speaker 01

  No. But when that happens, I get curious about it.

• 1:37:12Tim Ferriss?

  Yeah.

• 1:37:13Speaker 01

  What's going on in my life? Usually there's something that's happening that I'm, maybe I'm in resistance to. Maybe there's something I'm afraid of. But these things kind of operating somewhat subconsciously that I'm not really aware of. And this becomes the canary in the coal mine. It tells me something's not right. And that becomes an entry point into my work. And so I don't want to have filters or rules or anything like that. My belief as it relates to these kinds of things is if it's calling me, there's a deeper reason. And if I just avoid it, then I'll never really understand what that deeper reason is.

• 1:37:51Tim Ferriss?

  Not only that, but it strikes me that if you are suppressing, it's probably going to like squeeze out some corner of that box. You're trying to compartmentalize it into, and it'll manifest in some other way.

• 1:38:02Speaker 01

  That's right.

• 1:38:02Tim Ferriss?

  Now, let me just play devil's advocate though.

• 1:38:05Speaker 01

  Yeah.

• 1:38:05Tim Ferriss?

  Sexual drive, very fundamental, right? To human existence. And I could see if pushing that to an extreme, you could end up.

• 1:38:18Tim Ferriss?

  Inflicting a narrative of shame on yourself, even if you, let's say, want to masturbate. Which I think is a very natural impulse on a whole lot of levels. So this, this is not to get too super granular, but are you permitted or do you allow yourself to masturbate? And porn assisted masturbating is sort of a separate class because I do think those experiences are very different, right? I mean, as I think most men would agree. I mean, because you like, if you look at porn today versus porn five years ago versus porn 10 years ago, I mean, it's like an arms race. It is so extreme and it just gets more and more extreme.

• 1:38:58Speaker 01

  It's really just, yes.

• 1:38:59Tim Ferriss?

  And it's, and it's not all

• 1:39:01Speaker 01

  No.

• 1:39:02Tim Ferriss?

  over the top, but a lot of it is so extreme that it

• 1:39:05Speaker 01

  It's very dehumanizing.

• 1:39:06Tim Ferriss?

  It's, it can be dehumanizing and also at the very least is

• 1:39:10Speaker 01

  Desensitizing.

• 1:39:11Tim Ferriss?

  Desensitizing to the point that even very exciting sex on any normal level really can't compete in the mind with what you can get instantaneously online. I mean, it's, it's very, very challenging, right?

• 1:39:27Speaker 01

  Right.

• 1:39:28Tim Ferriss?

  How do you think about any of that?

• 1:39:30Speaker 01

  I think masturbation is kind of a normal thing.

• 1:39:34Tim Ferriss?

  Yeah.

• 1:39:34Speaker 01

  And probably, yeah, I don't have any specific issues with that. What I do think is very bad is porn.

• 1:39:44Tim Ferriss?

  Yep.

• 1:39:45Speaker 01

  In any amount, at any time, I think that zero is the right amount. I think it is toxic. I think it is hurting our young men.

• 1:39:55Tim Ferriss?

  Yeah, I agree.

• 1:39:56Speaker 01

  I think it is hurting young women. I think it's just bad, just all around. And I think masturbation is fine, but I, I think anything with porn is not good.

• 1:40:07Tim Ferriss?

  Yeah, don't put it on steroids with the porn assistance. Why do this book? Because these are subjects that most people would love to avoid talking about publicly.

• 1:40:17Speaker 01

  That's it. That's like a great reason to do it. I feel like we should be talking about these things more. That that's not why I did it, but I, as I'm experiencing the process of putting this book out into the world, it is amazing. You know, I was sitting next to someone on a plane, this woman on a plane. It was a plane taking off from LA. So everyone's in the entertainment business and she's like, oh, is that a manuscript? I was like, yeah, it's mine. I wrote a book and I'm, I'm reading it. What's it about? And I'm thinking, well, here we go. Here we go. You know, I'm going to have to start telling people soon. And so I tell her and then she starts opening up to me about things that have happened in her life and with her family.

• 1:41:01Speaker 01

  And it was like, 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.

• 1:41:12Tim Ferriss?

  Yeah.

• 1:41:12Speaker 01

  That's not exactly why I wrote it. There are a group of people out there, men and women, who are hurting. Maybe they're locked in some kind of shame cycle. Maybe they have been chasing after the things that society told them to chase after and they got those things and then realized they were miserable. And then when that happens, it's very disorienting, as I said earlier, and can be very scary. And they could be in a very dark place. And I hope that for them, this is a beacon of hope that says, hey, I'm not perfect either. It's okay. None of us are perfect. There's a way out that you can change. And if you look inside and go on that inward journey, you can heal and you can find your

• 1:41:57Speaker 01

  way out of this place. I think there's a secondary group, which is young men. I hope that this can be a little bit of a cautionary tale of what not to do. I just kind of blindly followed this thing that society was telling me. I thought society was telling me money, cars and women. I know for other young men, it's different things who grow up in different, different areas. But for me, it was money, cars and women. And I should have challenged that assumption. I should not have just blindly followed that because that didn't make me happy. And then I think the last group that I feel like this could potentially help are couples. Because Anne Marie and I went through some very, very difficult things.

• 1:42:40Speaker 01

  But we used those difficult experiences as opportunities to grow, to, you know, learn about ourselves, to heal ourselves, to grow as individuals, and then to grow as a couple. And I feel like if this could inspire a couple out there to get more honest with each other and hold some space for each other to not be perfect and to that you can make a mistake in a committed relationship and it doesn't have to mean the end of a relationship. I feel like that would be a good thing.

• 1:43:11Tim Ferriss?

  I think it'd be a tremendously, tremendously powerful thing. I mean, I think, I'm not that old, but I'm 44, 45. I forget, I'm getting old enough that I forget how old I am, that I've been able to see a whole cohort of my close friends get married, get divorced, get married, have trials and tribulations and all sorts of challenges. And I feel like the questions that you raise in your, in this conversation, in the book, in your story, the challenges that you talk about are in many ways, in some form or another, ubiquitous, right? It's just you don't hear, at least I don't hear many people talking about them openly.

• 1:43:56Tim Ferriss?

  But the fact of the matter is. It's everywhere.

• 1:44:00Speaker 01

  It's everywhere. And I say this in the afterword of the book. I say, my story was a story about getting lost in this porn thing and sex addiction and things like that. And then finding myself, you know, starting to heal and then finding myself. There's some intermediate steps as well that you mentioned earlier. There's like the pain and then there's the self medicating to avoid the pain. And then there's the kind of redemption and self discovery that can happen afterwards. And I feel like that's a universal story. I feel like so many people have that story. And that's one of the reasons I wanted to share it.

• 1:44:38Tim Ferriss?

  The porn star's journey.

• 1:44:40Speaker 01

  Yeah.

• 1:44:41Tim Ferriss?

  And the monk.

• 1:44:41Speaker 01

  It's a good title. Monks have mortgages. Monks don't have mortgages. That's right.

• 1:44:46Tim Ferriss?

  I was just thinking about your retreat.

• 1:44:48Speaker 01

  Yeah.

• 1:44:48Tim Ferriss?

  And the, the contrast. So the timeline then plays out in the book, leaves us, I believe, April 2015.

• 1:44:58Speaker 01

  Yeah, August 2015.

• 1:45:00Tim Ferriss?

  August. Yeah, that was close.

• 1:45:01Speaker 01

  Yeah.

• 1:45:02Tim Ferriss?

  It started with an A. So what have the years since looked like? And specifically, I'd love for you to comment at some point on what has been most challenging for you? And also, I know you don't want to speak for her, but for Anne Marie, what has been challenging? Because I bring this up for a very specific reason, and that is, when we talk about these stories of redemption, sometimes, this could be related to a particular, this might sound like a strange example, but like a particular surgery, a particular type of cancer treatment, a particular type of psychedelic therapy for, say, complex PTSD, where people hear these stories of redemption, but sometimes mistakenly believe.

• 1:45:49Tim Ferriss?

  That everything is solved.

• 1:45:51Speaker 01

  Hmm.

• 1:45:52Tim Ferriss?

  And it's sometimes helpful to set expectations that, hey, you're still gonna have to like row the rowboat and there's probably gonna be more work involved.

• 1:46:02Speaker 01

  It is a lifetime journey.

• 1:46:03Tim Ferriss?

  Right.

• 1:46:04Speaker 01

  You know, and there's no end to reach.

• 1:46:07Tim Ferriss?

  Yeah.

• 1:46:08Speaker 01

  And so I would say, the way I've described it is, in the early part, it was like, I'm, you know, we like to use the metaphor of climbing our spiritual mountain. So I'm climbing my mountain and there's like giant boulders blocking my path that I can't get past or, and the only way to get past them is to crawl through some dark cave where there's something really scary in there and I'm scared. And so in the early part of the climb, it was like that. Once you get past those kinds of parts, it gets a lot more subtle. There was a whole phase after all of this stuff where I feel like every three or four, maybe six months, something else would happen where the answer for me was like, you need to surrender even more.

• 1:46:52Tim Ferriss?

  And could you just remind me what that means to you, to surrender? Maybe you have an example you could share, any example where you're like, okay, universes, I get it.

• 1:47:04Speaker 01

  Yeah.

• 1:47:04Tim Ferriss?

  This is time for me to surrender.

• 1:47:05Speaker 01

  I feel terrible that I'm not, I'm not coming up with an example.

• 1:47:10Tim Ferriss?

  I'll tell you what, I think I can, I think I could get us there laterally.

• 1:47:13Speaker 01

  Yeah.

• 1:47:14Tim Ferriss?

  Think of, can you think of a time where you were doing the opposite of surrendering?

• 1:47:18Speaker 01

  Just like hanging.

• 1:47:19Tim Ferriss?

  Efforting the shit out of it.

• 1:47:20Speaker 01

  Yeah. Maybe in my venture capital work.

• 1:47:25Tim Ferriss?

  Okay.

• 1:47:25Speaker 01

  I mean, we have two funds. I tried so hard with my business partner to raise our second fund and we came in way short of our target and I was just working so hard and so, putting so much effort into that. And then after it didn't happen, after it didn't manifest, and I know there's a school of thought out there that's like, well, that means you didn't work hard enough and you just need to work harder next time and so on and so forth. But I kind of took it as a sign of like, maybe this just isn't the right thing for me.

• 1:47:58Tim Ferriss?

  Yeah.

• 1:47:58Speaker 01

  Like, maybe I need to do something different. And so maybe I need to let go of that thing. And then I did. And then I decided I was gonna write a book. And now this book thing is taking me in a completely new direction that's very fun, very exciting, very engaging.

• 1:48:15Speaker 01

  And I'm so thankful.

• 1:48:16Tim Ferriss?

  Yeah.

• 1:48:17Speaker 01

  And I think that came from letting go of that thing and kind of surrendering and saying, I need to listen to this sign.

• 1:48:23Tim Ferriss?

  Yeah, that makes me think of something that Seth Godin, the author, does a lot more than just write, but this author, he's famous for many, many books. He's written, God knows how many, I don't know, 20, 30, who knows, but Seth is one of the wisest people I know. And he's crafted a very unique life for himself, along with his amazing wife. And the way he's parented is really, really unusual, I think, impressive. And he, at some point, told this story of me of pushing boulders downhill instead of uphill. And he tells the story of this woman who'd been trying to sell some type of, I'm gonna get the details

• 1:49:06Tim Ferriss?

  wrong, but sell some type of toy concept, I don't know if it was a board game or something else, to all of these various types of manufacturers to license the idea. And it was just no after no after no after no. And he recommended just pivoting ever so slightly to something that was already getting all sorts of rave support from, I want to say, handful of friends or family, and to take a different approach and to push, basically not to do the hard thing, because it allows you to prove what you can achieve by working hard. And she ended up having this massive success. And it was by looking for the path of

• 1:49:44Speaker 01

  Less resistance, yes. And, you know, that's been a concept for me over time, too, this idea of conservation of energy.

• 1:49:51Tim Ferriss?

  Yeah.

• 1:49:52Speaker 01

  And saying, if it's that hard, maybe it's not the right thing to do. And yes, move in the direction of the thing that's coming easier. Because the first version is like, kind of a controlling version. It's like, I know what the answer is supposed to be, and I have to manifest that answer. Whereas the second version is more of a surrender approach and saying, I don't know what the answer is going to be. I'm gonna move in this direction.

• 1:50:21Tim Ferriss?

  Yeah.

• 1:50:22Speaker 01

  And that has, that has served me well.

• 1:50:26Tim Ferriss?

  What continues to be, or over the last, say, five years, what are some of the things that are still, that you still find challenging? I could think of a way to phrase that differently.

• 1:50:38Speaker 01

  No, no, it's a good question. I still have a tendency to be in my head more than I would like. I would like to embody my body more than I do, but it does not come easily for me and I have to work at it. I think partly related to that, I probably have a tendency to make myself busy sometimes as opposed to just having a little bit more stillness in my life. And so I think to me, all that means is those are actually good things in my opinion, because those are entry points for the work.

• 1:51:20Speaker 01

  I feel like the most difficult times of this kind of inward work and journey have been the times where I didn't really feel like I had a good entry point.

• 1:51:29Tim Ferriss?

  You don't have enough grist for the mill.

• 1:51:31Speaker 01

  Yeah, because then it's like, well, I know I need to keep climbing my mountain, but I'm not exactly sure what direction to go. So then you just put one foot in front of the other for a while and then something pops up that's not good or not serving you or you don't like. And then say, oh, okay, there's an entry point. And so sometimes those are a gift.

• 1:51:49Tim Ferriss?

  Is there anything that has stuck in particular from your retreat period, your four and a half months or whatever it was? Is there, is there anything, because you changed everything?

• 1:52:02Speaker 01

  Yeah, changed everything.

• 1:52:04Tim Ferriss?

  Were there any particular things that have stuck in part or wholly after that?

• 1:52:10Speaker 01

  You know, probably subtract, subtract, subtract, simplify, simplify, simplify. Like I, every day I feel like I just, I'm waking up saying, what do I not need to be doing anymore? What shouldn't I be doing anymore? Is there a relationship that's not serving me anymore?

• 1:52:27Tim Ferriss?

  Now, let's take that last example, because this is one that I know people have tremendous difficulty with.

• 1:52:32Speaker 01

  They do.

• 1:52:33Tim Ferriss?

  So, okay, you identify a relationship that's not serving you anymore. Let's, for the sake of argument, just say it's not your most significant other.

• 1:52:41Speaker 01

  Right.

• 1:52:41Tim Ferriss?

  Let's just say it's not that, but you identify friend X, and you're just like, yeah, this has run its course. What do you do then?

• 1:52:49Speaker 01

  I think for me that the signal is, there's a great quote from Maya Angelou. I'm probably gonna get it wrong, but it's something like this. People will forget what you say, they will forget what you do, but they'll never forget how you make them feel.

• 1:53:04Tim Ferriss?

  Mm-hmm.

• 1:53:05Speaker 01

  And if there's someone in your life, coworker, friend, family member, whatever, where every time you interact with that person, you kind of leave the interaction not feeling good.

• 1:53:18Tim Ferriss?

  Yeah.

• 1:53:19Speaker 01

  That's your body's intelligence. That's what, when I say I want to embody my body more, I want to listen to those signals.

• 1:53:24Tim Ferriss?

  For sure.

• 1:53:25Speaker 01

  Because the more I've done that, by the way, the better I feel like I perform in like a board meeting or with an entrepreneur, because I'm picking up on much subtler signals.

• 1:53:37Tim Ferriss?

  Yeah.

• 1:53:37Speaker 01

  My mind is quieter, and I'm picking that stuff up. So if you notice that, then I'm not sure I understand why it's hard now.

• 1:53:48Tim Ferriss?

  Well, tell me what you do, and then we'll find out.

• 1:53:51Speaker 01

  I think you just let it, I think you just let it go.

• 1:53:55Tim Ferriss?

  Right. Okay, so you're like, all right, I don't want to throw, there are probably a lot of Joes out there.

• 1:54:02Speaker 01

  We don't want to throw Joe under the bus?

• 1:54:03Tim Ferriss?

  Augustus. All right, Augustus. You're like, Augustus, every time I go to barbecue with this guy, invites me out for coffee. I come away and I just feel slightly drained.

• 1:54:11Speaker 01

  Well, the next time you get invited, maybe you're too busy to go.

• 1:54:14Tim Ferriss?

  Okay, and then he invites you the next week.

• 1:54:16Speaker 01

  And then maybe you're too busy to go.

• 1:54:18Tim Ferriss?

  Okay, and eventually you hope that Augustus just gets the signal.

• 1:54:22Speaker 01

  Yeah, I think so. I mean, you could take the other approach, which is, hey, when we spend time together, I don't really feel good afterwards, or that feels like a tall order. I don't have the guts to do that.

• 1:54:34Tim Ferriss?

  Okay, got it. All right, so it's the slow fade.

• 1:54:37Speaker 01

  I think so. I think these things just fade. And what I feel like... You know, a lot of people are resistant to this. You really did. In my opinion, you hit the nail on the head. This is the one that people are the most resistant to. They pride themselves on, I've been friends with this person since kindergarten. It's like a badge of honor.

• 1:54:56Tim Ferriss?

  Yeah.

• 1:54:56Speaker 01

  But people change.

• 1:54:58Tim Ferriss?

  Yeah.

• 1:54:59Speaker 01

  And maybe it does make sense to be friends with someone from first grade. But maybe it doesn't. Maybe by keeping yourself locked in that orbit, you're not allowing yourself to change. Or that person's not changing. And so when you let go of these things, it doesn't have to be mean. It can still be beautiful, but it also opens up space for a new relationship to enter that is a match for where you are now. Or if there's a gap there for a little while and you change, and then there's a new relationship that starts based on the new person that you are.

• 1:55:36Tim Ferriss?

  Let's shift gears a little bit, just to some broader questions, if that works for you.

• 1:55:42Speaker 01

  Yeah.

• 1:55:43Tim Ferriss?

  And then we can always come back to some more of the specific. But since, you know, I mentioned before we started recording, I was like, yeah, sometimes I ask these questions of a lot of my guests. Sometimes they don't really go anywhere. And I'll take the fall for that. We can always edit it out. But I mentioned the billboard question and you said, oh, I have an answer for that. So I haven't heard it yet. So to repeat the question that a lot of folks have heard, if you could put a quote, a message, word, question, image, whatever, non-commercial, on a billboard, again, metaphorically, to get a message out to billions of people, assuming they all understand it, what might you put on that billboard?

• 1:56:23Speaker 01

  This idea of climbing our spiritual mountain has just become so fundamental to our life that I would say something like, keep climbing your mountain, or don't stop climbing.

• 1:56:38Tim Ferriss?

  Don't stop climbing.

• 1:56:39Speaker 01

  Maybe keep climbing your mountain, or just keep climbing. That might be the...

• 1:56:43Tim Ferriss?

  Just keep climbing.

• 1:56:44Speaker 01

  There are so many questions over the last, you said, what have the last seven years been like? And after those big boulders and caves, there's more subtle stuff, but it's still there. There's still work. And there's so many times I'd ask Emery a question, should I do this or should I do that? You know, maybe it's a business question, could be related to whatever. Usually a business question. And her response would be, just keep climbing. And I'd be so frustrated and annoyed, be like,

• 1:57:16Speaker 01

  And then, and then I would be like, no, no, no, just, just keep climbing. You'll, the answer will reveal itself. Just keep climbing. And then I would go away and I would keep climbing. And sure enough, it would resolve or the answer would resolve. It's, it would present itself.

• 1:57:34Tim Ferriss?

  What books, I mean, soon the answer will likely be your own book, but putting your own book aside, what books have you gifted the most or recommended the most to other people?

• 1:57:47Speaker 01

  Love Warrior, the one I talked about earlier by Glennon Doyle. The Power of Now by Eckhart Tolle. That book changed my life, blew my mind. If you're going to read that book, take it slow, in my opinion. I can't tell you how many people I've met where they're talking to me about some issue or problem in their life. And I'm like, you should read The Power of Now. And they're like, oh, I read it. And I'm like, no, you didn't. You need to read it again. Because if you really read it, you wouldn't be saying what you're saying right now. There's a book into that in 18, maybe really trying to let go of, of the shame that I carried. Because even after I was healing myself, I still had a lot of shame for a long time.

• 1:58:31Speaker 01

  I was very embarrassed about the things that I had done.

• 1:58:35Tim Ferriss?

  So the shame was, for my own clarity, was the pornography and the cheating.

• 1:58:41Speaker 01

  The cheating, yeah. Yeah, absolutely. Very embarrassed, upset with myself, ashamed.

• 1:58:48Tim Ferriss?

  Yeah.

• 1:58:49Speaker 01

  And there's a book called Healing the Shame That Bind You.

• 1:58:52Tim Ferriss?

  Right.

• 1:58:53Speaker 01

  By John Bradshaw. Amazing book. And by the way, I read these books more than once. Like, some of these I've read four or five times, because I'll read them once a year, come back to them. Those are three that really stand out as having been really impactful. Another one, really just The Sexaholics Anonymous, the 12-step program literature, which is all the same, by the way, for every 12-step program. So I wound up reading the, the Blue Book of Alcoholics Anonymous. And that was amazing.

• 1:59:23Tim Ferriss?

  I've been meaning to read that for some time now.

• 1:59:26Speaker 01

  Yeah, it was, it was very powerful.

• 1:59:29Tim Ferriss?

  Let's talk about investments, but not perhaps in the traditional sense. So outside of the financial investments, can you think of a particularly, any very good investment that you've made worthwhile? Could be time, could be energy. Not to quote Warren Buffett, but I will. He talks about his best investment being investing in a Dale Carnegie speaking course. Uh huh. Cause it's sort of a multiplier for all of your other powers.

• 1:59:59Speaker 01

  Mm hmm.

• 2:00:00Tim Ferriss?

  That might be part of his like aw shucks grandpa shtick that he does. So who knows? But nonetheless, you get the idea for other people. The answer varies widely, but do any, any examples or options come to mind?

• 2:00:13Speaker 01

  Absolutely.

• 2:00:13Tim Ferriss?

  All right.

• 2:00:14Speaker 01

  It's hard to give these in order because they're, they're tied for first place, I would say.

• 2:00:20Tim Ferriss?

  Perfect.

• 2:00:21Speaker 01

  I've paid a lot of money for life coaching work.

• 2:00:24Tim Ferriss?

  Yeah.

• 2:00:24Speaker 01

  You know, over 10 years, it has been worth every penny. It has been worth so much more. That was an investment in myself that is just, has been priceless. And so to anyone out there who wants to talk to a therapist or a life coach or something, and who uses, if you can afford it, but you're kind of choosing not to afford it because you're worried about the cost, or you don't want to spend the money on it, I would rethink that because that work made me a more successful financial investor. And so all of that has come back to me, you know? If you just want to use the dollars, it's come back to me. But as far as what it's done for my relationships with my wife and my children, that's priceless. And so that's a good segue.

• 2:01:10Speaker 01

  The second one is I have invested a lot of time over the last seven years in my relationship with my wife and with my kids. In fact, I feel like my kids, I often get asked when I tell people I'm kind of phasing out of being a venture capitalist, like, well, what are you gonna do? You're just gonna get bored. And like, no, I have two kids. And helping launch two humans into the world is actually a huge responsibility. Like, I don't think we all appreciate sometimes how big of a responsibility that is. And investing in them and investing in their relationship, my relationships with them,

• 2:01:52Speaker 01

  has been the best investment in addition to the coaching work, like those things. That's how someone asked me recently, like, how do you define success for yourself? It's like, those relationships, that's it.

• 2:02:03Tim Ferriss?

  So if I may, take us from the sublime to the ridiculous for a second?

• 2:02:08Speaker 01

  Please.

• 2:02:09Tim Ferriss?

  I want to ask you about Excel, Microsoft Excel.

• 2:02:12Speaker 01

  Oh, sure.

• 2:02:16Tim Ferriss?

  This is from, I'm reading here, I want to see if this is any way ties in, because I'm also curious about the sort of early investments. So this is from Business Insider piece from God knows when. It's a piece called Career Advice from Peter Thiel's Mentee, or at least that's what they called it in the URL. Who knows what they ended up calling the headline? So on my first day at the company, nobody knew what I should do. A chemical engineering major who knew a little about business, it turns out that I did have one really valuable skill at the time. I knew a lot about Microsoft Excel. One of my undergraduate professors, and this is where the name comes in.

• 2:02:48Speaker 01

  Yeah.

• 2:02:49Tim Ferriss?

  Dr. David Clough.

• 2:02:51Speaker 01

  Clough.

• 2:02:52Tim Ferriss?

  C L O U G H. It insisted that we all learn a lot of the more powerful and sometimes obscure features of Excel.

• 2:02:59Speaker 01

  Yes. So when I got to PayPal, yeah, I was, I was a finance major, you know, I had been a chemical engineering major, and then I was in this kind of quasi-finance business graduate degree program. And

• 2:03:14Speaker 01

  Like I said earlier, the focus was not on hiring necessarily a specific skillset.

• 2:03:19Tim Ferriss?

  General capacity.

• 2:03:21Speaker 01

  Hiring on general capacity. So they saw something in me and said, we don't know exactly what he's going to do, but just get him in here.

• 2:03:27Tim Ferriss?

  Yeah.

• 2:03:28Speaker 01

  And so I went in and the first day I was like, what should I do? And the controller, the accounting controller in the finance team was like, well, something about a general ledger. And I was like, what's a general ledger? And she looked at me like, you've got to be kidding me. Like, what, who are you? And so anyway, I was started doing some stuff in Excel, tracking metrics, basically. Cause there was this daily report that would come out of the system and I would start, started keeping track of it every day. And then sending around graphs to everyone. And I was just good with Excel and that kind of launched my career at PayPal. So I have a lot of gratitude for, for Professor Clough and I owe him a lot.

• 2:04:10Tim Ferriss?

  So he was a professor of what?

• 2:04:13Speaker 01

  He was in the chemical engineering department at University of Colorado. And in, as I again mentioned earlier, in chemical engineering, you have like thermodynamics stuff. You have a lot of calculus, differential equations, like things that start to use some of the more obscure features and functions in Excel.

• 2:04:31Tim Ferriss?

  Yeah.

• 2:04:32Speaker 01

  And he always insisted that we learn that stuff.

• 2:04:36Tim Ferriss?

  So here's a question I've never actually had a chance to ask anyone and it just occurred to me, I should probably ask. I don't know a lot of CFOs or people who have been CFOs. What makes, and we can abstract this, I was going to ask what makes a great CFO, but you could also answer that by giving maybe an example, like thinking of someone in your mind of, of someone who's a superstar CFO and what differentiates one from the next?

• 2:05:03Speaker 01

  Oh, sure.

• 2:05:04Tim Ferriss?

  Cause I can think of CFOs and you have these, all of these different archetypes, right? But then in the CFO category, even CMO, I can imagine certain things, but I'm not a, certainly not a mathematician. I'm certainly not an accountant. I don't even begin to understand, or I can't pretend to understand what a CFO does day to day. So I don't know what differentiates one from another, right? Cause I'm like, well, like, all right, you got like first in, first out. You got some accounting principles. You got to make sure you behave on some level for like the SEC and certain circumstances. I'm like,

• 2:05:39Speaker 01

  What differentiates them? Yeah, so it's not a one size fits all thing. Yeah. Right? So different companies need different things. So the CFO of Boeing is probably a much different skill set than the CEO of PayPal. Or the CFO. I'm sorry CFO. Yeah. The CFO of a of a company that's building airplanes or something else. Right. Um, is different than the skill set of someone in financial services to some degree. So I have coached a lot of financial leaders from managers up to C level. And the way I explain this to them, because you meet a lot of VPs in all different roles, VP of marketing or VP of finance, and they all think they, well, they want to be the C level.

• 2:06:24Speaker 01

  So I'm the VP of finance. I want to be the CFO. I'm the VP of marketing. I want to be the CMO. What separates the VP from the C level? In my opinion, the shorthand I give them is that the C stands for confidence. And it's not necessarily that the CFO knows more about the technical accounting or the technical financial analysis or the treasury function or whatever is happening. But there's something about the energy that they carry, whether that comes from experience or it's just innate to them. But there's something about the energy they carry that when they walk in the room, it inspires confidence.

• 2:07:08Speaker 01

  And I think that's the C. And so, but again, these things are different for different companies at different stages. If I had to pick an amazing CFO, I would pick my boss when I was at PayPal. And I'm not just saying that, you know, to be obsequious. He was amazing. His name's Roloff Botha. Oh, yeah. He's now the head of Sequoia Capital globally. So it's not a fluke. He has been exceptional his entire life. I mean, I didn't know when he was younger before PayPal. We actually, funny enough, we overlapped at one of those classes at Stanford one time. So when we met each other at PayPal, it's like, oh, I recognize you. You know, I saw you in class, but he was an amazing boss, an amazing mentor.

• 2:07:51Speaker 01

  And for what PayPal needed at that time, an incredible CFO, because one of the biggest issues PayPal had was fraud in the early days and people defrauding the system. And he had been trained as an actuary and really understood like risk management and cohort analysis and things that none of us knew anything about. And he brought that to bear at PayPal. And it was a, I mean, priceless contribution. He was, he was amazing and he's just a great human.

• 2:08:22Tim Ferriss?

  Very, very bright guy. I maybe met him once in like 2009, like hello, goodbye kind of thing at some like, God knows what Silicon Valley event.

• 2:08:31Speaker 01

  He's busy.

• 2:08:32Tim Ferriss?

  Oh, he, yeah, but I've, I've heard so many good things.

• 2:08:35Speaker 01

  Yeah.

• 2:08:35Tim Ferriss?

  About him. What are some of the other things that you observed in him or learned from him? You said a great boss. What made him a great boss?

• 2:08:43Speaker 01

  You know, I was so young. It wasn't just a, he taught me so much about finance, but he also.

• 2:08:50Tim Ferriss?

  May I ask a silly question?

• 2:08:51Speaker 01

  Yeah.

• 2:08:52Tim Ferriss?

  What do you learn about finance on the job, on the ground in an environment like that that you don't learn in school? I know that might seem really stupid, but I'm just wondering.

• 2:09:01Speaker 01

  Well, in school, when we learned about financial modeling, it was more equation based. As it almost sounds silly when I say that, but when I got to PayPal, Roloff had built a very detailed financial model in Excel that really turns out to be like a very sophisticated accounting tabulation of everything that's happening in the business, which you can then use to forecast what's going to happen based on.

• 2:09:29Tim Ferriss?

  If you tweak this cell.

• 2:09:31Speaker 01

  Based on certain assumptions.

• 2:09:32Tim Ferriss?

  Right.

• 2:09:33Speaker 01

  And then you can do sensitivity analysis and things like that. And so it went from being this like esoteric concept to really tangible and really powerful. The other thing that he did for me that I still thank him for to this day was.

• 2:09:52Speaker 01

  He brought me along to so many meetings that he was attending.

• 2:09:56Tim Ferriss?

  Oh, that's a gift.

• 2:09:57Speaker 01

  It was such a gift and most of the time I just sat there. But like, I probably made the spreadsheet or printed the things out on the printer or helped him prepare for the meeting. And then he would say, well, you can come with me and I would go in and I would sit and I would listen. And I learned so much about how he had those conversations with people, sometimes difficult conversations. You know, the subtlety, the art of the softer side of, of business. When he was interacting with the investment banks, he would invite me to listen in on those phone calls or attend some of those meetings. And man, I learned so much.

• 2:10:37Tim Ferriss?

  I have to imagine, just knowing some of the stories, the early day stories from when I had Reid Hoffman on the show, that some of those conversations with investment banks must have been fascinating.

• 2:10:50Speaker 01

  Absolutely. Yes, yes, yes.

• 2:10:53Tim Ferriss?

  PayPal, PayPal had a lot going on.

• 2:10:55Speaker 01

  We had a lot going on.

• 2:10:56Tim Ferriss?

  Yeah. Oh, man, what an exciting journey you have had. Of course, with the bad with the good and the down with the up, but nonetheless.

• 2:11:08Speaker 01

  I would not trade it for anything. I know I went through this really weird thing into the dark. The porn stuff, the sex stuff, but man, it taught me so much.

• 2:11:22Tim Ferriss?

  So, closing question-ish, I always caveat that because I'm prone to saying, last question and then a half hour later, we're still going. Men and women listening, or if I want to be a little less, what is it, cisgendered? Just people listening who are in relationships, committed relationships, and they think to themselves.

• 2:11:43Tim Ferriss?

  I should have a conversation about this with my partner.

• 2:11:46Speaker 01

  Oh, I hope they do.

• 2:11:47Tim Ferriss?

  Right? Now, whether they have secrets, or they wonder if their partner has secrets, or anything in between. What advice would you give them in terms of how to open those conversations? Or when, or if to open those conversations?

• 2:12:08Speaker 01

  Yeah, this actually fits in with a question you asked earlier that I didn't really get to, which is like, the healing process and how do you trust someone again? And I think there's several different sides of it. One side is when you're looking at that other person, maybe don't necessarily see them as that person in that moment, but see them as a soul that's on a journey through this life, that is learning lessons and trying to figure out what those lessons are and trying to learn them. So Gary Zukoff says this in Seed of the Soul, that in the old days, marriages were based on like, maybe political affiliation,

• 2:12:53Speaker 01

  or maybe survival necessity in the very earliest days. And then it was like alliances and political stuff. And then it was love. You know, we were in this phase where like marriage is all about love. But his feeling was that in the future, what will define a successful marriage is mutual commitment to each other's spiritual growth. And so when you're in that relationship, if you can take yourself out of it for a moment, and say, we are two souls moving through this lifetime together, and we're both learning lessons. What are these lessons? How can we learn from each other? How can we help each other?

• 2:13:34Speaker 01

  Then, when the person reveals a secret that might be hurtful to you, you might be able to absorb it a little bit, instead of get immediately getting angry or immediately taking it personally.

• 2:13:48Speaker 01

  And absorbing it is another way of saying, holding that space. Right? You might be able to hold that space for that other person. And that is a gift and that is intimacy. And that is what it means to work together in a relationship. Cause you're in a relationship for a reason. The universe has brought you two together for a reason. You're supposed to be learning things from each other. And so help each other in that learning. Don't just say, you did the wrong thing, I'm out. Because guess what? Both of you are going to go on to repeat the same things. Until you learn the lesson. So why not just stick with each other a little bit longer?

• 2:14:31Speaker 01

  I understand that there are some relationships that maybe shouldn't proceed. Like especially if there's abuse or something like that. That's very serious. But I do think in our modern society, there is a tendency to pull the ripcord. Pretty early.

• 2:14:47Tim Ferriss?

  So I'm gonna come back to this thread. And this is related, but this is a very specific question. I'd love to know your thoughts on, which is. Let's just say, since we're sitting here, we're talking about your story. Let's just say it's a male who has issues with porn. Maybe it's gone beyond porn, wants to open up and be vulnerable and honest with his partner. Would you recommend they have that conversation? And then take the next steps towards, say, addressing some of those issues? Or would you suggest they potentially start with a 12 step program?

• 2:15:30Tim Ferriss?

  Take these steps to begin addressing the issues and then have the conversation?

• 2:15:35Speaker 01

  My first reaction is, and it's, it's hard. I try to be careful to generalize because I know it worked for us. But doesn't mean it would work for everyone, you know? But the way it unfolded for us was that we had this third party intermediary.

• 2:15:50Tim Ferriss?

  Right.

• 2:15:51Speaker 01

  Neutral third party intermediary who told us at the very beginning. I think we did have a joint session fairly early in our coaching. And she said, I'm never going to pick sides. I don't really care if you guys get divorced or stay together. I just want to help you both become well and healthy and whole individuals. Because if you're healthy and whole and well, if you decide to get divorced, it'll be fine. You won't need tons of lawyers. It'll just get divorced. And if you decide to stay together, it'd be beautiful. So it'll be beautiful either way. I think it's good to have an intermediary to help you through something like that because it helps. I think it can help.

• 2:16:34Tim Ferriss?

  Yeah, sees can get a little rough, I imagine. Any other thoughts for people who want to open a conversation, whether it's asking a partner? Right? Turning to them and asking whether they say it's related to pornography? And not to be too much of a spoiler, but be prepared for an affirmative answer, I'd say in most cases.

• 2:16:58Speaker 01

  Right, right, right.

• 2:16:59Tim Ferriss?

  Yeah, don't be shocked.

• 2:17:00Speaker 01

  Do you look at porn?

• 2:17:02Tim Ferriss?

  Yeah, just to just go into that expecting a yes. But any other recommendations for people who might want to have a conversation around these topics?

• 2:17:12Speaker 01

  Well, I mean, aside from potentially trying to find someone who can be a trusted third-party intermediary that can kind of help you hold space for each other. I mean, my other recommendation is that my healing, again, it's hard to generalize. My healing started when I finally started to reveal my secrets. And I feel like the sooner the better. Yeah, the sooner the better. Try to find someone who can help you through it. Try to hold space for each other and try to grow that way, you know, in love.

• 2:17:52Tim Ferriss?

  Well, Jason, you can be found at Jason Portnoy, P O R T N O Y dot com. That's the general departure point for all good things. The new book Silicon Valley Porn Star, which is easy to remember. So you definitely have that going for you with the book. It's a memorable title. Is there anything else that you would like to add? Any closing comments, public complaints you'd like to make about this podcast and how it's gone? Or requests of the audience, anything you'd like to point attention to? Anything at all that you'd like to add before we draw this to a close?

• 2:18:32Speaker 01

  You know, I think I would like to, I'd like to thank Anne Marie for being such an amazing life partner and for allowing me to go through what I went through and for holding that space and then for encouraging me with this book writing process and supporting me through that. She's just been amazing and incredible. So, thank you.

• 2:18:58Tim Ferriss?

  Perfect way to end. Jason, thank you so much for sharing your story and taking the time with me also. This has been an enjoyable conversation and enlightening conversation. I've taken a lot of notes myself. I've highlighted a number of different books, including your own. And I think that by writing this book, by having these conversations, you will do a lot of good. Because, as we covered earlier, these types of challenges are ubiquitous. The conversations may seem few and far between, but the challenges, the issues, you know, the caves and the boulders that we're talking about are ubiquitous and have existed in

• 2:19:43Tim Ferriss?

  some form or another for a very long time. A lot of these, not all of them, but I do think it's a service to put them on the table as subjects that can be discussed.

• 2:19:55Speaker 01

  Well, I appreciate you saying that. And I really appreciate you using your platform as a venue to do that.

• 2:20:02Tim Ferriss?

  My pleasure entirely. And for folks who are listening, we will include links to everything we've discussed, of course, including Silicon Valley Porn Star and all of the various resources, names, et cetera, in the show notes per usual at tim.blog/podcast. And until next time, be a little bit kinder than is necessary to others and to yourself. And thanks for tuning in.

• 2:20:29Tim Ferriss?

  Hey guys, this is Tim again. Just one more thing before you take off, and that is Five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? Between one and a half and two million people subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half-page that I send out every Friday to share the coolest things I've found or discovered, or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums perhaps, gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange esoteric things end up in my field,

• 2:21:14Tim Ferriss?

  and then I test them, and then I share them with you. So if that sounds fun, again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about. If you'd like to try it out, just go to tim.blog/friday, type that into your browser, tim.blog/friday, drop in your email, and you'll get the very next one. Thanks for listening. This episode is brought to you by Shopify. Shopify is one of my favorite companies out there, one of my favorite platforms ever. And let's get into it. Shopify is a platform, as I mentioned, designed for anyone to sell anything, anywhere, giving entrepreneurs the resources once reserved for big business. So what does that mean? That means in no time

• 2:21:56Tim Ferriss?

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• 2:22:38Tim Ferriss?

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• 2:23:19Tim Ferriss?

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• 2:24:02Tim Ferriss?

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• 2:24:47Tim Ferriss?

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• 2:25:28Tim Ferriss?

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