The Tim Ferriss Show - #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

Episode Date: June 15, 2022

Brought to you by LinkedIn Marketing Solutions marketing platform with ~770M users, Athletic Greens all-in-one nutritional supplement, and Shopify global commerc...e platform providing tools to start, grow, market, and manage a retail business. Entrepreneur, venture capitalist, and author Jason Portnoy began his career at PayPal, working closely with technology icons like Peter Thiel, Elon Musk, Max Levchin, and Reid Hoffman. He served as the first chief financial officer of Palantir Technologies and later founded Oakhouse Partners, a top-performing venture capital firm.Jason is sought after as a trusted advisor to technology company CEOs and has spoken on topics ranging from executive leadership to the intersections of technology and humanity. He holds engineering degrees from both Stanford University (MS) and the University of Colorado (BS).His new book is Silicon Valley Porn Star.Please enjoy!This episode is brought to you by LinkedIn Marketing Solutions, the go-to tool for B2B marketers and advertisers who want to drive brand awareness, generate leads, or build long-term relationships that result in real business impact.With a community of more than 770 million professionals, LinkedIn is gigantic, but it can be hyper-specific. You have access to a diverse group of people all searching for things they need to grow professionally. LinkedIn has the marketing tools to help you target your customers with precision, right down to job title, company name, industry, etc. To redeem your free $100 LinkedIn ad credit and launch your first campaign, go to LinkedIn.com/TFS!*This episode is also brought to you by Shopify! Shopify is one of my favorite platforms and one of my favorite companies. Shopify is a platform designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. No coding or design experience required.More than a store, Shopify grows with you, and they never stop innovating, providing more and more tools to make your business better and your life easier. Go to Shopify.com/Tim for a FREE 14-day trial and get full access to Shopify’s entire suite of features.*This episode is also brought to you by Athletic Greens. I get asked all the time, “If you could use only one supplement, what would it be?” My answer is usually AG1 by Athletic Greens, my all-in-one nutritional insurance. I recommended it in The 4-Hour Body in 2010 and did not get paid to do so. I do my best with nutrient-dense meals, of course, but AG further covers my bases with vitamins, minerals, and whole-food-sourced micronutrients that support gut health and the immune system. Right now, Athletic Greens is offering you their Vitamin D Liquid Formula free with your first subscription purchase—a vital nutrient for a strong immune system and strong bones. Visit AthleticGreens.com/Tim to claim this special offer today and receive the free Vitamin D Liquid Formula (and five free travel packs) with your first subscription purchase! That’s up to a one-year supply of Vitamin D as added value when you try their delicious and comprehensive all-in-one daily greens product.*[04:45] A caffeine-free breakfast[08:22] Background basics[10:52] Education and career diversions[16:51] Getting a job on the merits of an eclectic reading list and company t-shirt[21:47] Early days at PayPal[25:54] Lessons learned from Thiel, Hoffman, and Musk[31:40] Why were so many disparate projects seeded by the PayPal diaspora?[36:59] Peering into Palantir and the low-profile mindset[41:22] Origins of the title Silicon Valley Porn Star[44:02] Recognizing addiction, its escalating consequences, and its contributing factors[53:50] Escaping self-imposed victimhood and rescuing the marriage[1:05:52] Shared therapy and vocabulary[1:08:06] Simplifying and subtracting[1:15:20] Shame spirals and 12 steps (not South Africa)[1:25:22] From Porn Star to The Monk with help via choice reading selections and Coach Melissa[1:30:12] Reconciliation[1:33:22] Most important keys to the repair process[1:34:54] Safeguards against relapse[1:38:02] Modern porn vs. “natural” urges[1:40:11] What compelled Jason to write Silicon Valley Porn Star?[1:44:51] Time for surrender: filling in the post-book timeline[1:50:26] Enduring challenges[1:51:49] Retreat lessons[1:55:36] Jason’s billboard[1:57:34] Books most gifted[1:59:29] Good investments made[2:02:03] The obscure side of Microsoft Excel[2:04:36] What makes a great CFO?[2:08:52] Finance: on the job vs. school[2:11:21] Opening up to a partner about secrets we’ve been holding[2:17:52] Parting thoughts*For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast.For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsorsSign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissYouTube: youtube.com/timferrissFacebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Starting point is 00:00:00 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
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Starting point is 00:01:18 a small business owner makes their first sale on Shopify. More people in more places of all ages every single day. 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.
Starting point is 00:02:02 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. 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 slash Tim, that's S-H-O-P-I-F-Y.com slash 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 slash Tim right now and check it out. They have a lot to offer. Shopify.com slash Tim. 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
Starting point is 00:02:55 as all-in-one nutritional insurance. I recommended it, in fact, in the 4-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. 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
Starting point is 00:03:36 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 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 slash Tim. 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 slash Tim.
Starting point is 00:04:22 At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you just tell me what you had for breakfast as a starting point what do you have for breakfast i had these amazing scrambled eggs and sausage and fruit and orange juice sounds like a very complete breakfast it was very 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. Let's just talk about that for a second. So caffeine, sleep, sleep is my number one priority right now. How did you end up removing caffeine? Because that can be sometimes difficult. You just go cold turkey. 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.
Starting point is 00:05:33 Yeah. 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, 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. One cup. Yeah. That was it. And I think it affects different people differently, right?
Starting point is 00:06:01 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. And he mentioned this, and I've been progressively cutting back on caffeine, but God damn, do I love stimulants. It's hard. Well, I love coffee. So the
Starting point is 00:06:45 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. All right. And I did this once before I went a whole year. But then I started drinking coffee again. You went a whole year without coffee? Yeah. Wow. Incredible control.
Starting point is 00:07:10 Well, I can stay off the caffeine wagon for a few weeks at a time. Okay. 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.
Starting point is 00:07:27 In a restaurant, 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. Because caffeine blocks, or I shouldn't say in effect like blocks adenosine which builds up over time in your system and creates this sleep pressure yes and it uh i think it's an antagonist or it might be officially occupies the receptor that adenosine is did you read michael poland's latest book i think so i. I believe so. This would have been... This is your mind on plants? Morphine, caffeine, and mescaline.
Starting point is 00:08:07 That's right, yeah. Yes. Yeah. He talks about that. It was great. Any aversion to me mentioning other books, authors, anything like that? No, please do. Please do.
Starting point is 00:08:18 So let's set some context here. Yeah, let's do it. And we might just start the interview with what we just did. We're just going to get a rolling start here. Yeah, this is like the California roll. As the police officer once told me, the non-stop stop at a stop sign where you're just going to take down to five. I don't recommend this, folks. Talk to your local law enforcement before you try anything like that.
Starting point is 00:08:36 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,
Starting point is 00:09:00 and later founded Oak House 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. That is BS, not BSs, and you guys should know what I mean by now. His new book, which we will get to, is Silicon Valley Porn Star.
Starting point is 00:09:28 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. You're going to have to do a lot of this stuff in other interviews. So, might as well get some practice in. 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. I grew up in the suburbs of New Jersey, a town called Hillsborough, New Jersey.
Starting point is 00:09:58 My parents both worked. I had a sister or still have sister, who's about five years older than me. We had a couple cats, a family dog. It was pretty kind of 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. What did your parents do professionally? They were both chemists, interestingly.
Starting point is 00:10:21 Chemists. And did you follow in those footsteps? 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. Sounds good.
Starting point is 00:10:51 Sign me up. For those who don't know, what does a chemical engineer do? And what is chemical engineering? 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
Starting point is 00:11:24 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. I'd imagine with the energy sector and hydrocarbon industries in Texas, there are probably a lot of chemical engineers in Texas. A lot, yes. There must be. When did you diverge from your preordained high-paying career as a chemical engineer? Well, it probably started in college when I was an undergrad. I was at University of
Starting point is 00:12:00 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 one accounting class, one finance class, one macroeconomics class, one microeconomics class, and soconomics 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 so i got a master's degree at Stanford in a field that was really a combination of math and business. What is the ORF? No. So different schools call it by different names. Sometimes
Starting point is 00:12:53 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 that's what technically my degree is in. And you went straight from undergrad to grad school? I did. All right. What was your thinking behind that? What was the at least tentative plan or hope
Starting point is 00:13:24 or thinking, if any, behind that? What was the at least tentative plan or hope or thinking, if any, behind that? I just thought that's what everyone did. 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. That's what someone does. 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.
Starting point is 00:13:59 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 the direction I've gone in. I had a friend of mine on a long time ago on the podcast named Mike Maples, Mike Maples Jr. Oh, yeah. Who was the first person to introduce me
Starting point is 00:14:18 to angel investing and explain in some respect how the basics were. He's a good teacher. He is. 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 you, but it's a pretty good quote,
Starting point is 00:14:32 so you can take half credit anyway. He said something like, sometimes we need life to save us from what we want. Right. And that might be an example of that. Absolutely. So you didn't get into this PhD program. There you are at Stanford.
Starting point is 00:14:47 What are some of the more formative things or impactful occasions that come about while you're at Stanford? 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.
Starting point is 00:15:16 Now, are these people in your program or are they people who are at the graduate school of business? 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. Got it. And a lot of these people had some prior work experience. And after a while, after a few months in school,
Starting point is 00:15:41 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 is- Just continue. I get pretty bored interviewing myself.
Starting point is 00:15:57 Well, actually 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. So the dog outfit worked.
Starting point is 00:16:31 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. So let's talk about this job interview. Oh yeah.
Starting point is 00:16:55 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 your reading list, or at least partially, that was a factor. So who was that CEO? What was the company at the time? 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. 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. Oh, no kidding. Okay. Very good natured joke. So the company was called
Starting point is 00:17:31 Confinity. It was a company that had been started by Peter Thiel and Max Levchin. And the intention was to allow people to be 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. Just for those who don't know, Hobie's back in the day was a famous meeting place, famous deal-making spot. There were a handful of these.
Starting point is 00:18:19 And there's one in Woodside also. You know, the handful of these spots. But Hobie's, God, I'm bringing back the memories. Sorry to interrupt. That is where Mike and I used to meet for lunch to talk about this kind of stuff. So wow, Hobies, haven't thought about that. Okay. So you guys meet at Hobies. So we meet at Hobies. 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
Starting point is 00:18:53 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? What were some of the books? 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,
Starting point is 00:19:35 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. It's an eclectic portfolio of books. Yeah, it was. It was interesting. There's a lot of train rides in Europe. Yeah. Of the books and the train rides,
Starting point is 00:19:52 was there any particular at that point in your life that had stuck with you for any particular reason or that was memorable? 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.
Starting point is 00:20:16 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. 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 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 than as a lifestyle. Sure. Potentially. The newsletter, I just want
Starting point is 00:21:14 to piece together a few things. So you get an email about this job opening. 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 Friday afternoon lectures, essentially. And then there's a mailing list associated with that, and so that's where I got this. What was the job position? Financial analyst. Financial analyst. Yes. All right. So you ended up, how were you notified that you got this job?
Starting point is 00:21:58 So I have my breakfast with Peter. We talk about the book. I jokingly say I must've 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. Well, I like fun stories. 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 back then, a lot of stuff
Starting point is 00:22:50 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 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, call the CFO on his desk phone, maybe cell phone, 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. Wow. and then I would stuff them in envelopes and send them out. Yeah, so those were very early days. We had, I think when I started, we had about 14,000 PayPal users.
Starting point is 00:23:31 That's incredible. Yeah, it was crazy. 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?
Starting point is 00:23:42 I don't remember. At this point, it has to be hundreds of millions.'s a lot yeah it's a lot 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 absolutely in this whole story where he interviews b Chesky and they talk about doing things that don't scale in the beginning. That was something that didn't scale. Yeah. Doing a lot of things in the beginning that don't scale. 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? Peter's there. Max Levchin's there. There's probably,
Starting point is 00:24:27 I think I was employee 34. So I don't want to list off 33 other people. But names that people would recognize, much like we read in your bio. Yeah, sure. And was Reed around at the time? No. Not yet.
Starting point is 00:24:43 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. And so when I started at PayPal,
Starting point is 00:25:04 the two companies had not combined yet. 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,
Starting point is 00:25:24 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 truly an incredible sight. It's about as sort as Stepford Wives
Starting point is 00:25:48 like Truman Show as you can get, but it's a beautiful place. I used to spend a lot of time there. What are some of the lessons you learned or interesting practices that you observed with Peter? 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
Starting point is 00:26:35 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 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. 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? 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? Well, like in Peter's case, he had been running a hedge fund slash VC fund prior to PayPal starting,
Starting point is 00:27:19 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, he has... Busy boy. 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
Starting point is 00:28:12 he's applying to the other. And so I think there's a lot of transfer and benefit there. Yeah. You know, I 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. Could you elaborate? 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. 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 had worked pretty closely with Peter
Starting point is 00:29:00 because 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. And he told me to read this book called When Genius Failed, which is about long-term capital management. And then I thought, this is some light inspirational reading. I was like, I don't really know what hedge funds do.
Starting point is 00:29:43 He's like, go read this book. 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 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
Starting point is 00:30:21 you know I think he was he was thinking thinking, where could I be, you know, in several years, if we stayed on some kind of trajectory, not what was my current ability at the time. And is that something you've seen him do with other people? I mean, in the sense that it's something that'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?
Starting point is 00:30:52 Is it that it's easy to give? If it doesn't work out, obviously, the employment can always be terminated. Yeah, I don't want to speak too much for him. No, I'm not speaking for him, but if you were to speculate. Well, and because I know him is very thoughtful thoughtful i feel like he likes to invest in things that other people don't realize yet sure he's very good at it and so he does the same thing with people
Starting point is 00:31:15 so he meets a person that's a cool way 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.
Starting point is 00:31:37 And I think that's why. And it could be, there's a lot of people ask like, what was it about PayPal? Why was it so special? There were so many other companies. Meaning the constellation of then largely unknown superstars, or just what PayPal became itself as a company?
Starting point is 00:31:55 The former. 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. But it's just, the list is just crazy. And people always ask the question, why was that the case? And I'm not sure there's one answer,
Starting point is 00:32:22 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. A lot of potential energy that people didn't see. Yeah. Let's talk about that for a second. What did you observe, if anything, about the hiring process, right? You came in at 30 something.
Starting point is 00:32:48 34. Right, 34. And some of the names that people would recognize were not yet fixtures at that point. What else did you observe about kind of team assembly, whether it's at PayPal or at Clarion or elsewhere? 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,
Starting point is 00:33:18 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 where even Clarion Capital was a startup. It was a hedge fund, 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
Starting point is 00:34:01 thing. I think hiring for like general capability as opposed to specific skillset. 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 counterintuitive things. 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 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.
Starting point is 00:34:58 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. For people who are interested, I love Reed. 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. 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. Oh yeah. He is a force of nature. So incredible. Just a quick thanks to one of our sponsors and we'll be right back to the show. This episode is brought to you by LinkedIn Marketing Solutions. Time and place are
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Starting point is 00:37:13 And what does Palantir do? So I was at Clarion 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.
Starting point is 00:37:49 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. And what the company does is uses and you know palantir as a company is very secretive secretive yeah and and and and has a low profile so i want to be really respectful of sure yeah we know when we won't do the unauthorized uh you know investigative journalism piece but just people have an idea 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
Starting point is 00:38:54 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. I appreciate that answer. And I'm going to stand in for the audience who might want just a little bit more. 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? I think were.
Starting point is 00:39:26 So certainly it started out that way. But I know that they've made a lot of progress in diversifying their business lines into commercial spaces. I couldn't tell you the percentage difference. So I think two percentages, there'd be like US versus foreign would be one question, and then government versus commercial. And I don't feel versed
Starting point is 00:39:45 enough on on the data today but certainly at the beginning the first customers were the u.s government who was really struggling remember this was not that long after 9-11 and one of the things that we learned from the 9-11 experience was that, yes, we had all of this data, but we couldn't do anything with it. Yeah, it's not information. It's just data. It was just raw data. And so that was one of the reasons Palantir was formed, was to help with that problem. I'm just deeply, and again, we're not going to fixate on this, but deeply fascinated by businesses, or people for that 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
Starting point is 00:40:33 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 guy 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 there are like little well i shouldn't say little but there are certain quant shops especially that really do not want any publicity whatsoever 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. I think it makes sense to the
Starting point is 00:41:28 title of the book. And we can use that as a tool for making a sort of scene shift here. So Silicon Valley porn stars so far, Silicon Valley has come up. Porn star has not come up. So unless I'm missing something in the resume on LinkedIn, I don't think that you had this short stint in between undergrad and grad school. I did not. Okay, so fact check, accurate. Why Pornstar?
Starting point is 00:41:58 And you can answer this in any way that you like, but just to give us an idea of why this wording is in the book title. Yeah, sure. Well, it goes well together. No, it certainly gets people's attention. Yeah. The name porn star came from my life coach. And we haven't really talked much about the book yet,
Starting point is 00:42:20 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 part of my work. And if something is happening in your life that you want to take a closer look at, 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.
Starting point is 00:43:29 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. And 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. 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
Starting point is 00:44:19 pornography? 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 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 right online and then i just continued i just thought it was normal yeah 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 video download speeds
Starting point is 00:45:24 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 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? It seems like a pretty... Low percentage. I don't know about that.
Starting point is 00:45:58 Well, no, no. No, I mean, what I mean is it's a low percentage. You're 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. That's low percentage. That's a low percentage who are 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. That's low percentage. That's the low percentage. Yeah, so the high percentage.
Starting point is 00:46:10 The number of our generation suffered through very slow, practically dial-up speeds to download a three-second clip and you don't know what it's going to be. I think that's near 100%. Yeah, it's pretty high. 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, that kind of took it to a whole new level. And then I got into what I would refer to as a shame cycle. Yeah. And I didn't know it then.
Starting point is 00:46:42 And it took me a long time to figure that out and get out of it. But that's when that started. Now, I think you describe this in the book, but did the hookups begin with your lease on your apartment expiring and prompting you to go on Craigslist? Yeah, 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 the Bay Area. And I noticed this new, I don't know how new it was, but I had never noticed it before. There's a link in the personal section called casual encounters. Maybe it even had a little new 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.
Starting point is 00:47:36 Wild. Yeah. Now in retrospect, and maybe you knew this at the time, but what were the factors contributing to this behavior, which is this idea that unhealed traumas from our childhood can really affect our behaviors as we grow into adults. So I believe we're 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 or five or six years old, my father moved away. And that, I think it affected me. I didn't understand how it affected me until I was in my thirties. 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
Starting point is 00:49:12 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. 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's 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 I think that affected me too. And I don't,
Starting point is 00:50:24 I want to be really clear. And I say this towards the end of too. And I don't, I want to be really clear, and I say this 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. If you don't mind, and you can feel free to decline, that then maybe impacts your behavior as you get older. If you don't mind, and you can feel free to decline,
Starting point is 00:50:51 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? 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 today's standards, certainly, but more than I thought I would see in my 20s. So I was still pretty young.
Starting point is 00:51:26 And then I went to Clarion Capital, Peter Thiel's hedge fund. The hedge fund did really well. And I made big bonuses. And I started investing that money in startups. So again, there's more money flowing in. Peter's worth is climbing. And he's becoming more famous. And I was part of that group working for him. And so it felt like we were close to this guy who's becoming kind of a celebrity in some ways.
Starting point is 00:51:54 And then 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 and Marie and I invested a bunch of my bonus money from Clarion into Palantir early on. 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.
Starting point is 00:52:35 I just had lost all direction. Now, if you don't mind me getting into specifics, were you masturbating twice a day? Did 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 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. Yes. But I feel like I was way off the deep end relative to that. Yeah. So let's hear about it.
Starting point is 00:53:18 So it went from, I've already said it went from porn to Craigslist. Yeah. And then Craigslist at some point turned into online escort websites. Yeah. And then I had that kind of going on in the background in addition to porn. Yep. And then I wound up meeting someone at an event and starting an affair. Yeah. 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. Yeah, I was affair. Yeah. And that lasted for months. And so all of this stuff is happening.
Starting point is 00:53:45 I don't even know how I had time for all of that. I was wondering. Yeah. That's a lot of time. 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 Emory. I was just gone.
Starting point is 00:54:00 That's your wife. She's now my wife, yes. 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. 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 the story was different the story had evolved out of
Starting point is 00:54:32 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.
Starting point is 00:55:06 When did that change? It changed about six months after our daughter was born and I had disappeared on her. And then our daughter was born, which is of course very, you know, is a big event 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. The distance, the feeling of distance. Yeah, the distance and the feeling. 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, 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.
Starting point is 00:56:14 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 there was a bunch of different therapists in the mix. And then I wound up finding this life coach. But there's actually another trigger there. So I quit my job. 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 asked Anne-Marieie like, hey, I stopped working
Starting point is 00:57:06 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. 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.
Starting point is 00:57:34 And that was this huge kind of explosion that happened. And then she moved out and we separated and shared time with our daughter, you know we each had her two or three days at a time and we both started working with this life coach with the same woman 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 now you met her first this life coach? I did. Did you persuade Anne-Marie to then use the same life coach? No, I called her. So I had been talking with a therapist for, I don't remember how many months,
Starting point is 00:58:15 four to six months before I had my first session with this life coach. And just so we have a name, this is Melissa? 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. Right. And I'm not trying to say that to say anything bad about the therapist I was talking to. I'm sure they're
Starting point is 00:58:41 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 went, when I got to the parking lot, I called Ann 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? I was like, yeah. She said, well, maybe I should see this woman too. I was like, sure, why not? And so then she started and then we just continued now how initially and i know some of the details of this did you meet melissa how did that come to pass yeah so i had divine intervention in the form
Starting point is 00:59:36 of an ea yes absolutely so i had an ea when i was at palantir executive assistant yes executive assistant amazing woman her name's julie a tremendous business partner for me when I was at Palantir. Executive assistant. 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 in the sense that she just, with her daily constant interactions with you, could just feel that something was off. Yes, exactly. She was like, are you okay? And keep in mind, I'm CFO of this fast-growing Silicon Valley company. I also have all this
Starting point is 01:00:17 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, I don't think I'm okay. Why do you ask? You know? And then she said, she said, there's this woman that I know who kind of helps people in times of crisis or transition, and maybe you should talk to her. And that's kind of how that started. Wow. What was the EA's name again? Her name's Julie. So Julie gets chocolates every year. She's awesome. Yeah. All right. So there's this explosion. There are discoveries. Now I should ask, when you learned about her affair, did you at that point share
Starting point is 01:01:20 what you had been up to or were up to? Or did that not happen until later? 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 had no idea. I would never expect her to do something like that.
Starting point is 01:01:54 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. Oh, in the very first session? In the very first session. She said, you feel like, you know, cause 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,
Starting point is 01:02:16 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 catching on 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,
Starting point is 01:02:57 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. Yeah. And she was kind of onto me right from the beginning. From day one. From day one. So how did things then unfold? Because you've come back together with your wife, but we're skipping some in-between chapters. You are both meeting with Melissa. What are some of the key developments or moments
Starting point is 01:03:42 in, say, just making up a number here six months after you both start working with melissa well ann 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 dating relationships much you much, you know, Melissa, you were, when you say separated, were you geographically separate? Were you also divorced at that point? We were not divorced. Got it. 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. Right. I don't remember where the advice came from it could have been from melissa
Starting point is 01:04:28 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 let's not go nuclear immediately yes let's not go nuclear immediately. 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.
Starting point is 01:05:01 I'm pretty sure back in those days, most of our sessions were separate, although some of them were together, but really 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 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 different directions.
Starting point is 01:05:38 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 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 yeah and the therapist to his credit set certain rules up front and 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
Starting point is 01:06:20 session could be shared with ann marie vice versa, or that nothing would be shared unless there was sort of explicit permission granted? The latter. Nothing would be shared unless there was explicit permission. That's changed now. Yeah. But back then, you know, this whole thing had blown apart and we were not there. For sure. Yeah. No, I think it makes a hell of a lot of sense. I was just curious. Yeah. And Melissa might say, is it okay if I share this thing? Right. Yeah. But she did encourage us to share with each other. Can you give any examples of the shared vocabulary? I want to see if there's maybe a concept or
Starting point is 01:06:57 language that you could give as an example. Well, one of those would be this idea that, 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, the revelation was that Anne-Marie had been having an affair. I never came clean on my other behavior,
Starting point is 01:07:36 but I started to at least take responsibility for my disappearances related to work 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 want to speak for her too much anyway. For sure. Yeah.
Starting point is 01:07:55 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
Starting point is 01:08:27 Anne-Marie had certain things in her work where she also had to subtract and simplify. What type of work was she doing? When I said work just then, I meant her work with Melissa. Oh, the personal work. I see. Right. Yeah. 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, a good friend. And we went to a diner and it was full of all these tchotchkes and there was this hand-painted sign that said simplify. And I haggled and negotiated to buy this from this diner and put it in my house. Smart.
Starting point is 01:09:01 Which I have now. Smart. put in my house, which I have now. 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? 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 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.
Starting point is 01:09:35 I'll make this more tangible. So at first it was, so I had left Palantir and I couldn't detox immediately or I couldn't just cold turkey stop working. So I started trying to get all these consulting jobs. Right, right. You couldn't go from sixth gear to first gear. Yeah, yeah. 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 watch 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. It's a lot of the latter,
Starting point is 01:10:37 I think. Okay. For sure. Yeah. And I was really wrapped up in that. And so I had to stop doing that stuff too. That was another big thing that I kind of subtracted. Now, what was your technique or go-to language for that? You're just like, I'm sorry. Consider me dead for the next two months. Or was it, sorry, I have a conflict. Can't make this work. 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 inviting back then. Okay, right.
Starting point is 01:11:12 You were doing a lot of that. Because 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 so I just kind of had to stop. Just stop, period. And be more still. And that of had to stop. Just stop, period.
Starting point is 01:11:26 And be more still. And that's hard to do. How did Melissa sell this to you? Right? Uh-huh. Yeah. She said, you're efforting your way through life. And I was just livid.
Starting point is 01:11:49 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,
Starting point is 01:12:19 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 on it. 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. But that was how I felt. I was like, I don't know what this 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.
Starting point is 01:12:41 I promise you there is 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, sure, whatever. But also, I really wanted to save my marriage. 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. Is there a particular process that she uses to aid you with that subtraction?
Starting point is 01:13:24 Or is there, are there any filters you apply or is it are you just turned loose with the instruction to to subtract 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 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 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 part of ourselves that intuition and that in order to get back to that place, that like default state of peacefulness or happiness
Starting point is 01:14:26 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.
Starting point is 01:14:57 It's what's left when you get rid of all the things that make you unhappy. 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 yeah what is the sort of default core yeah let's introduce an acronym essay, not South Africa, sexaholics anonymous in this case, where did that enter the picture?
Starting point is 01:15:30 And did it enter the picture before or after you came clean with your wife about sort of your side of things? 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.
Starting point is 01:15:59 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, 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 Ann Marina had been through, it was like she just started feeling like,
Starting point is 01:16:46 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 kind of lost control of my life. And she said on the phone to me one day she being she be melissa you know we don't believe you and if you don't share your secrets you'll stay sick and if you
Starting point is 01:17:19 want to move forward you're going to 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 I've been going on for a very long time by then. And I started crying. I said, I have a serious problem, and I don't know how to stop, and I don't know what to do.
Starting point is 01:17:54 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 don't 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. And place us in time then, that was roughly when that was February of 2015 what is your participation looked like or attendance I'm not sure the right term to use sure since then since then so I attended at the beginning I attended meetings several meetings a day for weeks trying to find
Starting point is 01:18:41 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. Yeah. 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.
Starting point is 01:19:33 And I feel okay with that. 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,
Starting point is 01:20:06 you can climb out of that. So one more time, can you repeat those? 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, was just so helpful and so important. You said there were two pieces. Yes, there were two pieces. And at this very moment, I can't remember the second piece.
Starting point is 01:20:34 I'm so sorry. No, that's okay. It's okay. We can come back to it. Yeah. So let's think about this. So I was asking you about your participation and attendance since 2015. We flashed forward, Singapore, due to work, came back.
Starting point is 01:20:46 You didn't pick it back up, but I feel okay with that. I feel okay with that. And now I remember the second thing. That was my intention. Yeah, thanks for the reminder. So I feel like these addiction topic, it's a huge topic, right? We could talk for an hour just about that.
Starting point is 01:21:02 Oh yeah, many hours and i feel like having gone through that experience and 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 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
Starting point is 01:22:01 more shame. Now we go back, we act out again so that we can distract ourselves 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 and really actually break that addictive shame cycle. And 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 Mate would talk about asking not why the addiction, but why the pain. So people using,
Starting point is 01:22:58 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 escape or numb the pain and then the shame subsequent to using a coping mechanism that is not 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.
Starting point is 01:23:34 And I agree with you, and not a therapist, not an MD. 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, and then metabolize or recontextualize
Starting point is 01:24:00 or somehow contend with those in such a way that you remove the initiator in that first piece of the chain. So now you're describing these meetings, 2016, you're in Singapore. At that point, are you still- 2017. 17.
Starting point is 01:24:18 So 2017, at this point, are you guys still apart? No. 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 bare minimum stuff that I need to do to keep the, it's a VC 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
Starting point is 01:24:52 and I start reprogramming myself, I guess. I start journaling very intensively. So I'm going to essay meetings at least a few times a week. I'm journaling very intensively. I stopped'm going to essay meetings 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 change everything. I go to bed when it gets dark and then I wake up when it's dark and I journal to candlelight. So monks do have mortgages.
Starting point is 01:25:24 Monks do have mortgages monks do have mortgages in this case 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. I don't know Emmett Fox. I probably should. Oh yeah.
Starting point is 01:25:52 I like him a lot. Any starting point? 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 Emmett Fox is this, just reinforcing this idea that what is happening in your life situation or in your external universe, 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 I was in a shame cycle, however you want to
Starting point is 01:26:31 describe it. The society had told me I needed money, cars, and women to be happy and successful. So I thought I should go out and get those things. And then I was miserable. 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. So Melissa was still engaged at this point. So while you're-
Starting point is 01:26:56 I still talk to Melissa every week. Right. And during this ascetic sort of reclusive, I don't want to say reclusive, maybe that's not fair. Retreat. Retreat phase. Yeah.
Starting point is 01:27:06 You were still engaged with her on a regular basis? 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. During that period, I'm very interested in the things that worked. I'm also wondering, were there any dead ends? Anything that you tried where you're like, actually, this is counterproductive? Because you changed a lot of things. I changed everything. I changed everything. I changed my diet. I changed my sleep habits.
Starting point is 01:27:38 I changed my workout habits. I changed the people I talked to, the work I did. I changed everything. 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 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 compared to the person that you were, behaviorally speaking. 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 a 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.
Starting point is 01:28:47 And so I think I just didn't want to lose it all. And that was 2000. It was early, early 2015, early 2015. At what point, so I just have some notes here. These are,
Starting point is 01:29:02 these are from your book, two books, the seat of the soul. And then that first one is Gary Zukav, and then Healing the Shame That Binds You. Yeah. So 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
Starting point is 01:29:31 were Autobiography of a Yogi, Emmett Fox's books, and Glennon Doyle's book, Love Warrior. Love Warrior. And Love Warrior, you want me to tell you? Please. Yeah, Love Warrior, Glennon, if you haven't read the book,
Starting point is 01:29:52 she just shares her story and is very vulnerable. And I was in a very dark place and trying to figure out, 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, at first I thought we were getting divorced. 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
Starting point is 01:30:53 of us called Women Who Love Too Much by Robin Norwood. I've heard a lot about this book. I've never read it. It's a great book. And in that book, she talks about how women who are in families with an addicted 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
Starting point is 01:31:51 really 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 with her boundaries. 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.
Starting point is 01:32:19 And I was like, yes, ma'am. 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. When did Melissa reach out to Anne-Marie or were they also having an ongoing conversation? 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
Starting point is 01:33:04 four, 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. And we came back together and have been together ever since and it's been beautiful what have been some of the most important keys to the repair process like repairing trust in both in both directions right but particularly after getting back together after the retreat are there particular things that come to mind when I ask that? Yeah, it took a long time. You know, more for her to trust me again. Yeah. It took time. It just took time. I can imagine her also just being, not just distrusting at various points, but also really pissed off that you had, and I'm not casting judgment here, but that you had kept your secrets while condemning her. Absolutely.
Starting point is 01:34:08 That was horrible. It was just a horrible thing for me to have done. That's what made it so devastating. Yeah. Were there any particular steps or any particular conversations, aside from time healing all wounds, right? Which may or may not be true maybe deliberate practice heals a lot of wounds but what were some of the things that helped
Starting point is 01:34:29 yeah and and to your point about healing wounds and ann 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 yeah 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 happen and they were still painful. What safeguards do you put in place? I'm just imagining there's ubiquitous high-speed wifi everywhere. You have laptops, right? And if pornography on some level is like the gateway drug that opens Pandora's box, what are some of the rules and parameters or guide rails that you have for yourself? Nothing technology related. So I don't have special
Starting point is 01:35:23 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 like yeah well actually in the very dark first period it was it was hard um 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
Starting point is 01:36:06 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. 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. It takes all the fun out of it. Yeah. It de-sexifies the process. Absolutely. And so, it has been that process. So, it's been a long time since it's come knocking. I would be lying if I said that it never came knocking again. I would say probably on average once or twice a year
Starting point is 01:37:02 something happens. But when that happens... Birthday, morning of the birthday. No. But when that happens, I get curious about it. What's going on in my life? Usually there's something that's happening that 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 that tells me something's a deeper reason and if i just avoid it then i'll never really understand what that deeper reason is 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 that's right now let me just play devil's advocate though
Starting point is 01:38:05 yeah sexual drive very fundamental right to human existence and i could see if pushing that to an extreme you could end up 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 it's really just yes and it's and it's not all no over the, but a lot of it is so extreme that it desensitizes you.
Starting point is 01:39:07 It can be dehumanizing. And also, at the very least, it's 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 very, very challenging, right? So how do you think about any of that?
Starting point is 01:39:30 I think masturbation is kind of a normal thing. And probably, yeah, I don't have any specific issues with that. What I do think is very bad is porn yeah 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 yeah I agree I think it is hurting young women I think it's just bad just all around and I think masturbation is fine, but I think anything with porn is not good. Yeah. Don't put it on steroids with the porn assistants. Why do this book? Because these are subjects that most people would love to avoid talking about publicly. That's a great reason to do it. I feel like we should be talking about these things more. That's not why I did it, but as I'm experiencing the process of putting this book out into the world, it is amazing.
Starting point is 01:40:32 I was sitting next to someone 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 reading it. What's it about? And I'm thinking, well, here we go. Here we go. 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. 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. 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
Starting point is 01:41:24 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
Starting point is 01:41:57 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 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
Starting point is 01:42:33 like this could potentially help are couples because Anne-Marie and I went through some very, very difficult things, 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. 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
Starting point is 01:43:25 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 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. But the fact of the matter is, it's everywhere. 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. The porn star's journey. Yeah. It's a good title. Monks have mortgages. Monks don't have mortgages that's right i was just
Starting point is 01:44:46 thinking about your retreat yeah and the the contrast so the timeline that plays out in the book leaves us i believe april 2015 is that right august 2015 august yeah i was close. Yeah. 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,
Starting point is 01:45:43 where people hear these stories of redemption but sometimes mistakenly believe that everything is solved. And it's sometimes helpful to set expectations that, hey, you're still going to have to row the rowboat and there's probably going to be more work involved. It is a lifetime journey. Right.
Starting point is 01:46:04 And there's no end to reach. 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,
Starting point is 01:46:31 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 or maybe six months, something else would happen where the answer for me was like, you need to surrender even more. 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. Yeah. This is time for me to surrender.
Starting point is 01:47:05 I feel terrible that I, I'm not, I'm not coming up with a example. I'll tell you what, I think I can, I think I could get us there laterally. Yeah. Think of, can you think of a time where you were doing the opposite of surrendering or you were like efforting the shit out of it. Yeah. Maybe in my venture capital work. Okay. 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.
Starting point is 01:47:53 But I kind of took it as a sign of like, maybe this just isn't the right thing for me. Yeah. 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 going to write a book. And now this book thing is taking me in a completely new direction. That's very fun, very exciting, very engaging. And I'm so thankful. And I think that came from letting go of that thing and kind of surrendering and saying, I need to listen to this sign.
Starting point is 01:48:23 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
Starting point is 01:49:02 who'd been trying to sell some type of i'm gonna get the details 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
Starting point is 01:49:44 less resistance yes and you know that's been a concept for me over time too this idea of conservation of energy yeah 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 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 going to move in this direction yeah And that has served me well. What continues to be, or over the last, say, five years, what are some of the things that are still,
Starting point is 01:50:33 that you still find challenging? I could think of a way to phrase that differently. 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. 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. 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. You don't have enough grist for the mill. Yeah. Cause 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
Starting point is 01:51:39 then something pops up that's not good or not serving you or you don't like and they say oh okay there's an entry point and so sometimes those are a gift 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 yeah Yeah, I changed everything. Were there any particular things that have stuck in part or wholly after that? You know, probably subtract, subtract, subtract, simplify, simplify, simplify. Every day I feel like 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?
Starting point is 01:52:27 Now, let's take that last example because this is one that I know people have tremendous difficulty with. They do. 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.
Starting point is 01:52:41 Right. 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 i think for me that the signal is there's a great quote from maya angelou i'm probably going to 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. And if there's someone in your life, coworker, friend, family member, whatever, where every time you interacted with that person, you kind of leave the interaction,
Starting point is 01:53:21 not feeling good. Yeah. 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 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. Yeah. My mind is quieter and I'm, I'm picking that stuff up. So if you notice that, then I'm not sure I understand why it's hard. Well, tell me what you do. Yeah. Then we'll find out. I think you just let it go. Right.
Starting point is 01:53:56 Okay. So you're like, all right, I don't want to throw. There are probably a lot of Joes out there. We don't want to throw Joe under the bus. Augustus. All right. Augustus. You're right, Augustus. You're like, Augustus, every time I go to barbecue with this guy, he invites me out for coffee.
Starting point is 01:54:09 I come away and I just feel slightly drained. Well, the next time you get invited, maybe you're too busy to go. Okay. And then he invites you the next week. And then maybe you're too busy to go. Okay. And eventually you hope that Augustus just gets the signal. Yeah, I think so.
Starting point is 01:54:23 I mean, you could take the other approach, which is, hey, when we spend time together, I don't really feel good afterwards. That feels like a tall order. I don't have the guts to do that. Okay, got it. All right, so it's the slow fade. I think so.
Starting point is 01:54:38 I think these things just fade. And what I feel like, 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 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.
Starting point is 01:54:56 Yeah. But people change. Yeah. 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. 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
Starting point is 01:55:24 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. Let's shift gears a little bit just to some broader questions, if that works for you. Yeah. And then we can always come back to some more of the specific. But since 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.
Starting point is 01:55:56 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? This idea of climbing our spiritual
Starting point is 01:56:25 mountain has just become so fundamental to our life that I would say something like, keep climbing your mountain or don't stop climbing. Don't stop climbing. Maybe keep climbing your mountain or just keep climbing. That might be the... Just keep climbing. There are so many questions over the last you said what 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 amory a question should i do this or should i do that you know it's maybe it's a business question could be related to whatever usually a a business question. And her response would be,
Starting point is 01:57:07 just keep climbing. And I'd be so frustrated and annoyed. I'd be like, what are you talking about? Yeah, you're like, okay, Yoda. Come on, I'm trying to make a choice here. And then I would be like, no, no, no, just keep climbing. The answer will reveal itself. Just keep climbing. And then I would go away and I would 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 would present itself. Yeah. Hmm. 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 love warrior the one i talked about earlier by glennon doyle the power of now by eckhart tolle
Starting point is 01:57:53 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 um 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.
Starting point is 01:58:31 I was very embarrassed about the things that I had done. So the shame was for my own clarity was the pornography and the cheating and the cheating. Yeah. So on. Yeah, absolutely. Very embarrassed, upset with myself, ashamed. Yeah. And there's a book called Healing the Shame That Binds You by John Bradshaw. Amazing book. And by the way, I read these books more than once. Some of these I've read
Starting point is 01:59:00 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 blue book of Alcoholics Anonymous and that was amazing. I've been meaning to read that for some time now. Yeah, it was very powerful. 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.
Starting point is 01:59:49 Not to quote Warren Buffett, but I will. He talks about his best investment being investing in a Dale Carnegie speaking course because it's sort of a multiplier for all of your other powers. 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 examples or options come to mind? Absolutely.
Starting point is 02:00:14 It's hard to give these in order because they're tied for first place, I would say. Perfect. I've paid a lot of money for life coaching work over 10 years. It has been worth every penny. It has been worth so much more. That was an investment in myself that 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
Starting point is 02:00:56 investor. And so all of that has come back to me. 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. The second one is I have invested a lot of time over the last seven years in my relationship with my wife and like my kids, I often get asked when I tell people I'm kind of sometimes how big of a responsibility that is and investing in them and investing in their relationship my relationships with them 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 so if I may take us from the sublime to the ridiculous for a second, please, I want to ask you about Excel, Microsoft Excel. Oh, sure.
Starting point is 02:02:16 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 a 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,
Starting point is 02:02:37 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, Dr. David Clough,
Starting point is 02:02:52 C-L-O-U-G-H, had insisted that we all learn a lot of the more powerful and sometimes obscure features of Excel. Yes. So when I got to PayPal, yeah, 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
Starting point is 02:03:12 and like I said earlier the focus was not on hiring necessarily a specific skill set general capacity 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. Yeah. And so I went in and the first day I was like, what should I do? And the controller, the accounting controller
Starting point is 02:03:34 and 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, who are you? And so anyway, I started doing some stuff in Excel, tracking metrics basically, because there was this daily report
Starting point is 02:03:54 that would come out of the system and I would start 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 Professor Clough and I owe him a lot. So he was a professor of what?
Starting point is 02:04:13 He was in the chemical engineering department at University of Colorado. And as I again mentioned earlier, in chemical engineering, you have like thermodynamic stuff. You have a lot of calculus, differential equations, things that start to use some of the more obscure features and functions in Excel. And he always insisted that we learn that stuff. So here's a question I've never actually had a chance to ask anyone, and it just occurred to me
Starting point is 02:04:40 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 someone who's a superstar CFO
Starting point is 02:04:59 and what differentiates one from the next. Because I can think of CFOs and you have all these different archetypes, right? Mm-hmm. But then in the CFO category, even CMO, I can imagine certain things, but I'm certainly not a mathematician.
Starting point is 02:05:20 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 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? Because I'm like, well, like, all right, you got like first in, first out. You got some accounting principles.
Starting point is 02:05:34 You got to make sure you behave on some level for like the SEC in certain circumstances. I'm like, what differentiates them? Yeah, so it's not a one size fits all thing, 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. Oh, sorry, CFO.
Starting point is 02:05:53 The CFO of a company that's building airplanes or something else 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. 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
Starting point is 02:06:47 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. And I think that's, 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 that to be obsequious. He was amazing. His name's Rolof Botha. 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.
Starting point is 02:07:38 We actually, funny enough, we overlapped at one of those classes at Stanford one time. So when we met each other at PayPal, I was like, oh, I recognize you. I saw you in class. But he was an amazing boss, an amazing mentor. 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 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 priceless contribution.
Starting point is 02:08:20 He was amazing. And he's just a great human. Very, very bright guy. I maybe met him once in 2009, like, hello, goodbye kind of thing. It's some God knows what Silicon Valley event. He's busy. Oh, yeah. But I've heard so many good things 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? You know, I was so young. It wasn't just, he taught me so much about finance,
Starting point is 02:08:49 but he also- May I ask a silly question? Yeah, yeah. 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.
Starting point is 02:09:01 Well, in school, when we learned about financial modeling, it was more equation-based. 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 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- If you tweak this cell. Based on certain assumptions. Right. 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
Starting point is 02:09:46 that I still thank him for to this day was he brought me along to so many meetings that he was attending. Oh, that's a gift. It was such a gift. And most of the time I just sat there, but I probably made the spreadsheet or printed the things out on the printer or helped him prepare for the meeting.
Starting point is 02:10:08 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 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. I have to imagine just knowing some of the stories, the early days stories from when I had Reed Hoffman on the show, that some of those conversations with investment banks must have been fascinating.
Starting point is 02:10:50 Absolutely. Yes, yes, yes. PayPal had a lot going on. We had a lot going on. Yeah. Oh man.
Starting point is 02:10:57 What an exciting journey you have had, of course, with the bad, with the good and the down with the up, but nonetheless. 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.
Starting point is 02:11:22 So closing question-ish, I always caveat that because I'm prone to saying last question and 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, I should have a conversation about this with my partner. Oh, I hope they do. Right? Now, whether they have secrets
Starting point is 02:11:50 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 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 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,
Starting point is 02:12:27 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 zukov says this in seed of the soul that in the old days marriages were based on like maybe political affiliation 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 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. 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?
Starting point is 02:13:34 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 immediately getting angry or immediately taking it personally. 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. Because 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? I understand that there are some
Starting point is 02:14:32 relationships that maybe shouldn't proceed, 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. So I'm going to 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, 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, take these steps to begin addressing the issues,
Starting point is 02:15:33 and then have the conversation? My first reaction is, and it's hard, I try to be careful to generalize. Because I know what worked for us, but it 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, 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.
Starting point is 02:16:19 It'll just get divorced. And if you decide to stay together, it'll 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. Yeah. C's can get a little rough, I imagine. Any other thoughts for people who want to open a conversation, whether it's asking a partner, 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,
Starting point is 02:16:57 I'd say in most cases. Oh, right, right, right. Yeah, don't be shocked. Do you look at porn? Yeah, just go into that expecting a yes. But any other recommendations for people who might want to have a conversation around these topics 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
Starting point is 02:17:27 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 in love. Well, Jason, you can be found at jasonportnoy.com. That's for the general departure point for all good things. The new book, Silicon Valley Porn Star,
Starting point is 02:18:04 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? You know, I think I would like to, I'd like to thank Anne-Marie
Starting point is 02:18:36 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. 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, an enlightening conversation. I've taken a lot of notes myself. I've highlighted a number of different books, including your own.
Starting point is 02:19:26 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 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. Well, I appreciate you saying that. And I really appreciate you using your platform as a venue to do that. My pleasure entirely. And for folks who are listening, we will include links to everything we've discussed, of course, including Silicon Valley Pornstar and all of the various resources, names, et cetera, in the show notes per usual at
Starting point is 02:20:17 tim.blog slash podcast. And until next time, be a little bit kinder than is necessary to others and to yourself. And thanks for tuning in. 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
Starting point is 02:20:44 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, and then I test them, and then I share them with you.
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