The Tim Ferriss Show Transcripts: Jason Portnoy of PayPal, Palantir, and More — Porn Addiction, The Corrosiveness of Secrets, Healing Wounds, Escaping Shame Cycles, and Books to Change Your Life (#600)

Please enjoy this transcript of my interview with entrepreneur, venture capitalist, and author Jason Portnoy. Jason 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.

Transcripts may contain a few typos. With many episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, Google Podcasts, Stitcher, Amazon Musicor on your favorite podcast platform.

#600: Jason Portnoy of PayPal, Palantir, and More — Porn Addiction, Sexaholics Anonymous, Shame Spirals, and His Path to Recovery and Redemption


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Tim Ferriss: Okay, so we should be recording. Why don’t you just tell me what you had for breakfast as a starting point. What did you have for breakfast?

Jason Portnoy: I had these amazing scrambled eggs, and sausage, and fruit, and orange juice.

Tim Ferriss: Sounds like a very complete breakfast.

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

Tim Ferriss: Well, let’s just talk about that for a second. So caffeine, sleep. Sleep is my number one priority right now.

Jason Portnoy: Yeah. Same.

Tim Ferriss: How did you end up removing caffeine? Because that can be sometimes difficult. Or you just go cold turkey?

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

Tim Ferriss: One cup. Yeah.

Jason Portnoy: That was it. And I think it affects different people differently, right?

Tim Ferriss: Yeah. It does. And I have, genetically, a predisposition, or I suppose it’s 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, 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.

Jason Portnoy: Well, I love coffee. And so the second night, I slept so deeply it was 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 send me back there.” And then I fell asleep again, and I’ve just been sleeping like a baby for the last week.

Tim Ferriss: Wow. All right.

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

Tim Ferriss: You went a whole year without coffee.

Jason Portnoy: Yeah.

Tim Ferriss: Wow. Incredible control. What discipline.

Jason Portnoy: No, actually, what’s that?

Tim Ferriss: What discipline.

Jason Portnoy: Oh, okay.

Tim Ferriss: Well, I can stay off the caffeine wagon for few weeks at a time. And then I develop a tolerance so quickly. Once I have one cup, what’ll generally happen is, I’m having it in, say, a restaurant. If I have it in a coffee shop, it’s safer because you have to pay for the second cup. In a restaurant — 

Jason Portnoy: You just keep going.

Tim Ferriss: — the endless cup of coffee phenomenon starts to manifest and then I’ve had three cups. And then before I know it, if I have a day without caffeine, I just feel like I’m asleep on my feet.

Jason Portnoy: Oh, wow.

Tim Ferriss: Right? Because caffeine blocks, or I shouldn’t say — in effect, blocks adenosine, which builds up over time in your system and creates this sleep pressure. And I think it’s an antagonist or it might be — it actually occupies the receptor that adenosine is — 

Jason Portnoy: Did you read Michael Pollan’s latest book?

Tim Ferriss: I think so.

Jason Portnoy: Okay.

Tim Ferriss: I believe so. This would’ve been — 

Jason Portnoy: This is Your Mind on Plants.

Tim Ferriss: Morphine, caffeine, and mescaline.

Jason Portnoy: That’s right. Yeah.

Tim Ferriss: Yes.

Jason Portnoy: Yeah.

Tim Ferriss: Yeah.

Jason Portnoy: He talks about that.

Tim Ferriss: It was great. Yeah.

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

Tim Ferriss: No. No, no. Please do. Please do it. So let’s set some context here.

Jason Portnoy: Yeah, let’s do it.

Tim Ferriss: And we might just start the interview with what we just did.

Jason Portnoy: We’re just going to get a rolling start here.

Tim Ferriss: Yeah. This is like the California roll. A police officer once told me the non-stop stop is 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. My guest today, Jason Portnoy, nice to see you.

Jason Portnoy: Good to be here.

Tim Ferriss: 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 chief — try that again. He served as the first chief — so used to saying CFO. I can’t read that entire thing.

Jason Portnoy: Okay, you can say CFO.

Tim Ferriss: He served as the first chief financial officer, AKA CFO, 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. That is BS, not BS as in — you guys should know what I mean by now. His new book, which we will get to, is Silicon Valley Porn Star. What a title. And we will certainly delve into the origins of that. But let’s start with the basics first. Just paint a picture. And this is the boring foundational work for this interview, but you’re going to have to do a lot of this stuff in other interviews. So you might as well get some practice in.

Jason Portnoy: Sure.

Tim Ferriss: Where’d you grow up? Basics of the family.

Jason Portnoy: Sure.

Tim Ferriss: Just the connective tissue of childhood. Maybe just a little bit of that to get us started.

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

Tim Ferriss: What did your parents do professionally?

Jason Portnoy: They were both chemists, interestingly.

Tim Ferriss: Chemists. And did you follow in those footsteps?

Jason Portnoy: 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.”

Tim Ferriss: “Sounds good. Sign me up.” For those who don’t know, what does a chemical engineer do? And what is chemical engineering?

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

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

Jason Portnoy: A lot. Yes.

Tim Ferriss: There must be.

Jason Portnoy: Yeah.

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

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

Tim Ferriss: What is the — ORF? O-R-F?

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

Tim Ferriss: And you went straight from undergrad to grad school?

Jason Portnoy: I did.

Tim Ferriss: All right. What was your thinking behind that? What was the at least tentative plan, or hope, or thinking, if any, behind that?

Jason Portnoy: 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.

Tim Ferriss: That’s what someone does.

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

Tim Ferriss: I had a friend of mine on a long time ago on the podcast named Mike Maples. Mike Maples, Jr. — 

Jason Portnoy: Oh, yeah.

Tim Ferriss: — who was the first person to introduce me to angel investing and explain in some respect how the basics worked.

Jason Portnoy: He’s a good teacher.

Tim Ferriss: Yeah, I owe Mike a lot. And I remember, I think it was Mike who said on the podcast, sorry, Mike, if I’m misquoting it, but it’s a pretty good quote, so you can take half credit anyway. He said something like, “Sometimes we need life to save us from what we want.”

Jason Portnoy: Right.

Tim Ferriss: And that might be an example of that.

Jason Portnoy: Absolutely. Yeah.

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

Jason Portnoy: Yeah, 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.

Tim Ferriss: Now are these people in your program? Are they people who are at the graduate school of business, GSB?

Jason Portnoy: Both.

Tim Ferriss: Both.

Jason Portnoy: 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.

Tim Ferriss: Got it.

Jason Portnoy: And a lot of these people had some prior work experience. And after a while, after a few months in school, I realized it was really helpful for them because they could contextualize the things that we were learning. And whereas for me, it was all very abstract. And so I decided I wanted to get a job. And that, if I should continue, that is — 

Tim Ferriss: Please continue.

Jason Portnoy: Yeah. So there was a — 

Tim Ferriss: I get pretty bored interviewing myself, so yeah, please.

Jason Portnoy: 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 Fogdog. I thought it was hilarious. And I really wanted to work there.

Tim Ferriss: So the dog outfit worked.

Jason Portnoy: 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.

Tim Ferriss: So let’s talk about this job interview.

Jason Portnoy: Oh, yeah.

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

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

Tim Ferriss: Oh, no kidding. Okay.

Jason Portnoy: But a very good-natured joke. So the company was called Confinity. It was a company that had been started by Peter Thiel and Max Levchin. And the intention was to allow people to beam money to each other on their PalmPilots. 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. But my first interview was with Peter at a Hobee’s restaurant in Palo Alto, California.

Tim Ferriss: Hobee’s? Just for those who don’t know, so Hobee’s, back in the day, was a famous meeting place, famous deal making spot.

Jason Portnoy: Yeah.

Tim Ferriss: There were a handful of these, and there’s one in Woodside also. A handful of these spots, but Hobee’s — God, this is bringing back the memories. Sorry to interrupt.

Jason Portnoy: No, it’s okay.

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

Jason Portnoy: There you go.

Tim Ferriss: So, wow. Hobee’s, haven’t thought about that. Okay. So you guys meet at Hobee’s.

Jason Portnoy: So we meet at Hobee’s, I’m wearing the company t-shirt that I got from a buddy on campus. He thinks that’s pretty hilarious. And he’s telling me all about his background and Confinity’s plans. And again, a lot of it’s going over my head, but it sounds very cool and very interesting. And he’s very nice. And then I casually mention 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.

Tim Ferriss: What were some of the books?

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

Tim Ferriss: It’s an eclectic portfolio of books.

Jason Portnoy: Yeah. It was. It was interesting. A lot of train rides in Europe.

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

Jason Portnoy: 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 the bull fighting in Spain and things. And I was probably reading that while I was on a train in Spain.

Tim Ferriss: Totally.

Jason Portnoy: So there was something about that whole thing. The Art of War was definitely fascinating as well. Man, there were others. I’m sorry. I can’t remember more.

Tim Ferriss: No, that’s fine. Hemingway, I’m just 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 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, right? 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.

Jason Portnoy: Sure.

Tim Ferriss: Potentially. So the newsletter, I just want to piece together a few things. So you get an email about this job opening.

Jason Portnoy: Yes. So I’m part of something called BASES. 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. And 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.

Tim Ferriss: What was the job position?

Jason Portnoy: Financial analyst.

Tim Ferriss: Financial analyst.

Jason Portnoy: Yes.

Tim Ferriss: All right. So you ended up — how were you notified that you got this job?

Jason Portnoy: Well, so I had my breakfast with Peter. We talk about the books. I jokingly say, “I must have read the right books,” because I get an email later that day, “Hey, great news. We’d like you to come in for some additional interviews.” So I go in, I don’t know, a few days later, and I meet with a lot more people on the team. And then I get hired and I start working there January third of 2000. So this interviewing stuff happened in December. I start working in January. I mean, I have some fun stories from back then if you’re — 

Tim Ferriss: Well, I like fun stories.

Jason Portnoy: 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 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. And then, 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 him in envelopes and send them out.

Tim Ferriss: Wow.

Jason Portnoy: Yeah. So those were very early days. I think when I started, we had about 14,000 PayPal users.

Tim Ferriss: That’s incredible.

Jason Portnoy: Yeah. It was crazy.

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

Jason Portnoy: I don’t remember. At this point, it has to be hundreds of millions I would think.

Tim Ferriss: That’s a lot.

Jason Portnoy: Yeah. It’s a lot. It’s a big number.

Tim Ferriss: It’s a big number. And 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 — 

Jason Portnoy: Absolutely, yeah.

Tim Ferriss: — in this whole story where he interviews Brian Chesky, and they talk about doing things that don’t scale in the beginning.

Jason Portnoy: That was something that didn’t scale.

Tim Ferriss: 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?

Jason Portnoy: Peter’s there. Max Levchin’s there. I think I was employee 34. So I don’t want to list off 33 other people.

Tim Ferriss: No. But names that people would recognize, much like we read in your bio.

Jason Portnoy: Yeah, sure.

Tim Ferriss: And was Reid around at that time?

Jason Portnoy: No.

Tim Ferriss: Not yet.

Jason Portnoy: Not yet. I don’t think Reid was around yet. And Elon existed very nearby. So he had started a company called 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, the two companies had not combined yet.

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

Jason Portnoy: That’s pretty amazing.

Tim Ferriss: — an incredible sight.

Jason Portnoy: Yeah.

Tim Ferriss: It’s about as Stepford Wives, 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?

Jason Portnoy: Well, one of the biggest things I noticed, frankly with Peter, certainly with Reid, 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’ve 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 spanning that three year timeframe, watching them, they always tended to be doing multiple things. And I feel like they got a lot of benefit out of doing that because they would be getting exposed to different ideas, or solving different 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.

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

Jason Portnoy: Well, in Peter’s case, he had been running a hedge fund / VC fund prior to PayPal starting. Had met Max. Max had this idea. They decided that they were going to work on it together. Peter invested money out of his fund to help launch the thing. And he still had the fund on the side. It 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 Reid’s case, I don’t remember in detail, but I mean, even if you just look at Elon today — 

Tim Ferriss: Sure.

Jason Portnoy: He has — 

Tim Ferriss: He’s a busy, busy, busy boy.

Jason Portnoy: Yeah. Super busy. Well, even busier, I guess, the last couple 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 — he’s learning things from one that he’s applying to the other. And so I think there’s potentially some benefit there.

Tim Ferriss: Right, there’s a lot of transfer.

Jason Portnoy: Yeah.

Tim Ferriss: I’d read, let me just pull this up here, that Peter would give employees titles and levels of responsibility that reflected their potential, not their current ability. Could you elaborate on that?

Jason Portnoy: Well, I was a perfect recipient. I was on the receiving end of that. So I was at PayPal for about three years, the company goes public, then gets acquired by eBay. And five or six of us leave to go help Peter start his hedge fund again.

Tim Ferriss: This is Clarium?

Jason Portnoy: Clarium Capital, yeah. So he’s going to go back to his fund. He renames it, and decides he wants to build this. This is going to be his next project. And so when I get there, this is pretty funny. So I had worked pretty closely with Peter 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 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 Clarium, 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 — 

Tim Ferriss: Oh, it’s about long term capital management.

Jason Portnoy: Long term capital management. And then I thought — 

Tim Ferriss: Just some light inspirational reading.

Jason Portnoy: Yeah. I was like, “I don’t really know what hedge funds do.” He’s like, “Go read this book.”

Tim Ferriss: Great.

Jason Portnoy: 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. And looking back, it’s kind of comical, but I would just — I was like, “This is my education. This is how I’m going to do this.” 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 know anything about this.” And he was like, “You’ll pick it up quick.” He had a lot of confidence and faith, and we had worked together pretty closely for a while by that point. And so I feel like that was a good example. I think he was thinking, “Where could I be in several years if we stayed on some kind of trajectory?” Not what was my current ability at the time.

Tim Ferriss: And is that something you’ve seen him do with other people 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? Is it that it’s easy to give? If it doesn’t work out, obviously, the employment can always be terminated. So how would you — 

Jason Portnoy: Yeah, I don’t want to speak too much for him, because he’s — 

Tim Ferriss: No, not speaking for him, but if you were to speculate.

Jason Portnoy: Well, because I know him as very thoughtful. And he’s very thoughtful. And so I feel like he likes to invest in things that other people don’t realize yet.

Tim Ferriss: Sure. He’s very good at it.

Jason Portnoy: And so he does the same thing with people. So he meets a person — 

Tim Ferriss: That’s a cool way to go about it.

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

Tim Ferriss: Why was that — now, meaning the constellation of then largely unknown superstars, or just what PayPal became itself as a company?

Jason Portnoy: The former.

Tim Ferriss: Okay.

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

Tim Ferriss: It’s just really — 

Jason Portnoy: The list is just crazy.

Tim Ferriss: Yeah.

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

Tim Ferriss: Yeah. A lot of potential energy that people didn’t see.

Jason Portnoy: Yeah.

Tim Ferriss: Well 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 — 

Jason Portnoy: Mm-hmm, 34.

Tim Ferriss: Right, 34. And some of the names that people would recognize were not yet fixtures at that point. What else did you observe about team assembly, whether it’s at PayPal or Clarium or elsewhere?

Jason Portnoy: Yeah. So two things come to mind right away. One is hiring for general ability. And I’m not exactly sure how to say that, but as opposed to saying, “Does this person have the very specific skills to do this very specific job,” it would be more focused on, “Is this person just exceptional, in lots of different ways?” Because if they are, they’re going to be exceptional at whatever job they have to do.

And a lot of my experience in a working environment is at startups, where even Clarium Capital was a startup. It was a hedge fund. It was a startup. And so people, 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.

Tim Ferriss: Right.

Jason Portnoy: So that was one thing, I think, hiring for general capability, as opposed to specific skillset. I think another thing, certainly at PayPal, 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 counter — not counterproductive but — 

Tim Ferriss: Counterintuitive.

Jason Portnoy: Counterintuitive, thanks. And so at PayPal, PayPal merged with, and 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,” 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.” You know?

Tim Ferriss: Yeah.

Jason Portnoy: And that served PayPal really well.

Tim Ferriss: For people who are interested, I love Reid. I’ve spent a bit of time with him and he’s been on the podcast, and if I remember correctly, at some point Peter would refer to him as Firefighter in Chief.

Jason Portnoy: Yeah.

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

Jason Portnoy: Oh, yeah. No, he is a force of nature, absolutely.

Tim Ferriss: So incredible.

Tim Ferriss: You’ve mentioned a name a couple of times now, that I’d love to shift to. For people who know it and for those who don’t, because I’m sure a lot won’t, Palantir.

Jason Portnoy: Oh, yeah.

Tim Ferriss: Palantir is a very interesting company. How did you end up at Palantir, and what does Palantir do?

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

Tim Ferriss: Secretive?

Jason Portnoy: Secretive, yeah, and has a low profile. So I want to be really respectful of that.

Tim Ferriss: Sure. Yeah. We won’t do the unauthorized investigative journalism piece, but just so people have an idea.

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

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

Jason Portnoy: Oh, sure.

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

Jason Portnoy: I don’t know. I wouldn’t know. I think were, so it certainly started out that way, but I know that they’ve made a lot of progress in diversifying their business lines into commercial spaces.

Tim Ferriss: Got it.

Jason Portnoy: I couldn’t tell you the percentage difference, so I think two percentages — there’d be US versus foreign, would be one question, and then government versus commercial. And I don’t feel versed enough on the data today. But certainly at the beginning, the first customers were the US 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 because — 

Tim Ferriss: Yeah, it’s not information, it’s just data.

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

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

Jason Portnoy: I love that guy.

Tim Ferriss: — or a business, whether it’s a Palantir or, I’m not going to mention them just because it would annoy the people involved, but some of these hedge fund shops. Right? They’re like little — well, I shouldn’t say little, but there are certain quant shops especially, that really do not want any publicity whatsoever. 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, deeply interesting, especially when very smart people are involved, because you would 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 title of the book. And we can use that as a tool for making a sort of scene shift here. So, Silicon Valley Porn Star. So far, Silicon Valley has come up, Porn Star has not come up. 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 — 

Jason Portnoy: I did not.

Tim Ferriss: Okay. So, fact check, accurate. Why Porn Star? And you can answer this in any way that you like, but just to give us an idea of why this wording that’s in the book title.

Jason Portnoy: Yeah, sure. Well, it goes well together. No. It certainly gets people’s attention.

Tim Ferriss: Yeah.

Jason Portnoy: The name “Porn Star” came from my life coach. And we haven’t really talked much about the book yet, but I went on this journey, and part of that journey was a realization that I was addicted to online porn. And after several years of trying to stop the habit and not being able to, I finally realized that I should tell my life coach this, because maybe she could help me.

And I told her, and we started working on this as part of my work. And she has this technique, or tool, where we would say that a person has a lot of identities in their universe. And if something is happening in your life that you want to take a closer look at, you might assign that behavior to a specific identity. And what it does is it 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 am not a bad person. This identity of mine is doing this thing that I don’t like. Let’s figure out why.”

And she called that identity Porn Star. The first time she said it, we both laughed, 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 Porn Star doing this week?” And just the levity around it and her curiosity around it actually encouraged me to start sharing things that otherwise would have been just very embarrassing to share. And that was really what started a lot of my healing.

Tim Ferriss: So let’s roll back the clock and look at where Porn Star enters stage left, in a sense. When did you first recognize that you had addiction or any issues related to pornography?

Jason Portnoy: Whew. It probably wasn’t until 2013 or ’14, 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.

Tim Ferriss: Sure.

Jason Portnoy: And I had an internet connection, and it was super slow, and the pictures took a long time to load. And that’s when I started looking at porn online. And then I just continued. I just thought it was normal.

Tim Ferriss: Yeah.

Jason Portnoy: Every guy does this. The volume of content is infinite, effectively, so you just get — if you’re immersed in it, you just feel like, “Oh, everyone’s doing this.” But 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 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?

Tim Ferriss: Right. It seems like a pretty low percentage.

Jason Portnoy: I don’t know about that.

Tim Ferriss: Well, no, no. What I mean is it’s a low percentage for 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.”

Jason Portnoy: Yeah, makes sense. Okay.

Tim Ferriss: That’s low percentage.

Jason Portnoy: That’s the low percentage. Yeah. So the high percentage — 

Tim Ferriss: The number who, 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 percent.

Jason Portnoy: Yeah, it’s pretty high.

Tim Ferriss: Yeah.

Jason Portnoy: 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.

Tim Ferriss: Yeah.

Jason Portnoy: And I didn’t know it then, and it took me a long time to figure that out and get out of it, but that’s when that started.

Tim Ferriss: Now, the — and I think you describe this in the book, but did the hookups begin with your lease on your apartment expiring, and prompted you to go onto Craigslist?

Jason Portnoy: Yeah, that’s exactly right. So my apartment lease was going to expire soon. I went onto 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 Personals 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. And, yeah.

Tim Ferriss: Wild.

Jason Portnoy: Yeah.

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

Jason Portnoy: Yeah, absolutely.

Tim Ferriss: — explore that in any way that makes sense.

Jason Portnoy: Yeah. It’s a great question. I didn’t understand it at the time. It took me a very long time to understand what was going on under the surface, but I think — and this goes to one of the major themes of the book, which is this idea that unhealed traumas from our childhood can really affect our behaviors as we grow into adults. So I believe we are all kind of programmed in our childhood, and then we go out into the wild and we experience new situations, and we compare the situation to our programming to figure out what we’re supposed to do. It’s 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 30s, so it took a really long time, but I think whenever — again, I don’t think this is super controversial to say. When a primary caregiver leaves, it is very difficult on a child.

The second thing that happened for me was that my mother, once I got into the middle 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, and I feel like they still are. 

Tim Ferriss: Yeah, still are.

Jason Portnoy: But there was all these medications, Prozac, other things — and so when she was home, she was kind of distant. She was either in bed or, if she was awake and walking around, she was a little bit distant, maybe not fully there because of this medication stuff. And 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 those are formative years for kids. We’re trying to figure ourselves out. And I think that affected me too.

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.

Tim Ferriss: If you don’t, and feel free to decline, when it was — when your behaviors later, as 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/behavior look like?

Jason Portnoy: Yeah. The moment where it really felt like I was kind of spinning out of control?

Tim Ferriss: Mm-hmm.

Jason Portnoy: Just rewinding a little bit, I had 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. And then I went to Clarium Capital. Peter Thiel’s 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, it feels like, and he is 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. 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 Peter’s next big thing, a big Silicon Valley story. I’m the CFO. Anne Marie and I invested a bunch of my bonus from Clarium into Palantir, early on. And so we were making a lot of money on paper. And my ego just was swelling, and I just, I thought I could do anything. I thought I deserved anything I wanted. And that’s when — that was the first kind of peak of bad behavior, where I was just spinning like a top. I just had lost all direction.

Tim Ferriss: Now, if you don’t want me getting into specifics — 

Jason Portnoy: No, it’s good.

Tim Ferriss: I mean, were you, like, masturbating twice a day to pornography? Was it a couple 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 No Booze, 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. Right?

Jason Portnoy: Yes. This was not — but I feel like I was way off the deep end, relative to that.

Tim Ferriss: Yeah. So let’s hear about it.

Jason Portnoy: Yeah. I’ve already said it went from porn to Craigslist.

Tim Ferriss: Yeah.

Jason Portnoy: And then Craigslist, at some point, turned into online escort websites.

Tim Ferriss: Yeah.

Jason Portnoy: And then I had that going on in the background, in addition to porn, and then I wound up meeting someone at an event and starting an affair. And that lasted for months. And so all of this stuff is happening. I don’t even know I had time for all of that.

Tim Ferriss: Yeah, I was wondering.

Jason Portnoy: Yeah.

Tim Ferriss: That’s a lot of time.

Jason Portnoy: Yeah. Looking back, I don’t know how I was doing that. I guess the way I was doing it was I had completely disappeared on Anne Marie. I was just gone. I was — 

Tim Ferriss: That’s your wife.

Jason Portnoy: She is 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.

Tim Ferriss: At the time, what was the story you told yourself about those behaviors? In other words, was the self-narrative, “Wow, this spinning like a top, this is out of control. I don’t know what to do,” at that point? Or was the story different?

Jason Portnoy: The story was different. The story had evolved out of — in our relationship, I wanted to have sex more frequently than Anne Marie did. And at some point, it turned into 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.

Tim Ferriss: When did that change?

Jason Portnoy: It changed about six months after our daughter was born. I had just disappeared. I had disappeared on her. And then our daughter was born, which of course 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, but that — 

Tim Ferriss: The distance, the feeling of distance.

Jason Portnoy: Yeah, the distance and the doing. I wasn’t even — like, 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. I’m going to quit my job. I’m going to try to turn this around.” And I started working with a marriage therapist. She started talking to a marriage therapist. Then there were a bunch of different therapists in the mix, and then I wound up finding this life coach. But there was actually, there’s another trigger there, where — 

So I quit my job. I think I stopped in January of 2010. And 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, “What’s going on here?” And I asked Anne Marie, like, “Hey, I stopped working so I could be home, so that we could try to reconnect,” and she was like, “You can’t just expect me to go back to the way things were. And I didn’t really have a good thing.”

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

Tim Ferriss: The same woman?

Jason Portnoy: The same woman, yeah, which I know is unique and a little bit unusual, but it worked for us. It may not work for everyone, but it worked for us.

Tim Ferriss: Now, you met her first, this life coach?

Jason Portnoy: I did. Yes.

Tim Ferriss: Did you persuade Anne Marie to then use the same life coach?

Jason Portnoy: No. I called her — so I had been talking with a therapist for, I don’t remember how many months, four to six months before I had my first session with this life coach.

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

Jason Portnoy: 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 what I would call traditional therapy.

Tim Ferriss: Right.

Jason Portnoy: And I’m not trying to say that to say anything bad about the therapists I was talking to. I’m sure they’re great, and they did help me to some degree, but I got more out of that one hour than I had in months. And so I was so excited that, when I got to the parking, I called Anne Marie. And we still had enough communication lines open for this. We were coordinating schedules for our daughter and things like that. And I said, “I just have to tell you about this session I just had with this life coach.” I didn’t know what a life coach was.

And I told her, and she said, “Wow. You got all of that out of one hour?” 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.

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

Jason Portnoy: Yeah. So I had — 

Tim Ferriss: Divine intervention in the form of an EA.

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

Tim Ferriss: Executive Assistant.

Jason Portnoy: 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, she could see that things were not right, because she was kind of intimately involved in things that were going on with me at work.

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

Jason Portnoy: Yeah. 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 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 falling apart or fraying at the seams. I was not healthy. And she was like, “Are you okay?” I was like, “I don’t think I’m okay. I don’t think I’m okay. Why do you ask?” And then 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.

Tim Ferriss: Wow. What was the EA’s name again?

Jason Portnoy: Her name’s Julie.

Tim Ferriss: So Julie gets chocolates every year.

Jason Portnoy: She’s awesome, yeah.

Tim Ferriss: 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 what you had been up to or were up to? Or did that not happen until later?

Jason Portnoy: 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 had no idea. I would never have expected her to do something like that. I just played into that whole thing. And that was one of the things Melissa called me out on in that first session.

Tim Ferriss: Oh, in the very first session?

Jason Portnoy: In the very first session. I share this in the book. I’m telling her this story and the whole time I’m telling her the story, I’m just expecting her to be like, “Oh, you poor thing. Wow, how does that make you feel?” That sort of thing. So I’m telling her bits of the story waiting for this feedback that the rest of the world had given me, this sympathy, and I’m not getting any of it. And I’m like, “Okay, what’s going on here?” 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!” Very good. You’re — 

Tim Ferriss: You’re catching on.

Jason Portnoy: You’re catching on. You’re following me. But little did I know that 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 I think maybe my first reaction is, “What are you talking about?” She’s like, “You’ve created the conditions in your life for this to happen.” And then later in the session, “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. And she was kind of on to me right from the beginning.

Tim Ferriss: From day one.

Jason Portnoy: From day one.

Tim Ferriss: So how did things then unfold? Because you’ve come back together with your wife, but we’re skipping some in between chapters, right? You are both meeting with Melissa. What are some of the key developments or moments in say, just making up a number here, six months after you both start working with Melissa?

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

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

Jason Portnoy: We were not divorced.

Tim Ferriss: Got it.

Jason Portnoy: 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 when something like this happens in a lot of relationships, the tendency is that’s it, we’re getting divorced. I don’t remember where the advice came from. It could have been from Melissa. Certainly Melissa’s advice was don’t make any big decisions for a few months. And I think that was code for don’t decide to get divorced. Don’t completely change everything. There’s a lot of work to be done. There’s a lot of work that has to be done here.

Tim Ferriss: Let’s not go nuclear immediately.

Jason Portnoy: Yes, let’s not go nuclear immediately. So we were separated. Anne Marie moved out and had an apartment. It was not that far away, a mile away in San Francisco or something like that. And so we’re talking to Melissa, let’s say in that first six months, and most of the time it’s separate. I’m pretty sure back in those days, most of our sessions were separate. Although some of them were together, but really we’re 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 it was nice. 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. But so because of her, it kind of kept our lines of communication open and we would share sometimes something we might have learned in one of our sessions.

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

Jason Portnoy: The latter. Nothing would be shared unless there was explicit permission. That’s changed now, but back then this whole thing had blown apart and we were not there yet.

Tim Ferriss: For sure. Yeah, I think it makes a hell of a lot of sense. I was just curious.

Jason Portnoy: Yeah. And Melissa might say, “Is it okay if I share this thing?” But she did encourage us to share with each other.

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

Jason Portnoy: Well, one of those would be this idea that 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, 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’ve been, and I wouldn’t want to speak for her too much anyway, but that was one for me. This idea that I am responsible and 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 the 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 because of this. But I was just doing way too many things and I needed to subtract and simplify. And I think Anne Marie had certain things in her work where she also had to subtract and simplify.

Tim Ferriss: What type of work was she doing?

Jason Portnoy: Well when I said work just then I meant her work with Melissa.

Tim Ferriss: Oh, the personal work. I see. Right.

Jason Portnoy: Yeah.

Tim Ferriss: I literally have a little sign that I got when I was a trucky at some point with this guy named Chris Sacca, a great guy, good friend, and we went to a diner and there was, it was full of all these tchotchkes and there was this hand painted sign that “Simplify.” And I haggled and negotiated to buy this from this diner and put it in my house.

Jason Portnoy: Smart.

Tim Ferriss: Which I have now.

Jason Portnoy: Smart.

Tim Ferriss: I think sometimes I’m better at looking at it than I am at implementing it, but I’m curious for you, what were some of the meaningful subtractions that were made? And how did you choose what to subtract?

Jason Portnoy: Yeah, I would say it’s kind of like peeling an onion or something. It’s just layers and layers and layers. 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. And 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.

Tim Ferriss: Right. Right. You couldn’t go from sixth gear to first gear.

Jason Portnoy: 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, had 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 never watched a ton of TV, but I pretty much stopped watching TV entirely. And I got a lot more selective. I used to do lots of lunches and breakfasts and dinners. I don’t know if it was just me or if it was Silicon Valley culture. I’m not sure.

Tim Ferriss: It’s a lot of the latter I think.

Jason Portnoy: Okay.

Tim Ferriss: For sure.

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

Tim Ferriss: 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.”

Jason Portnoy: Nothing blanket. It was always just a one-off thing. Like, “Sorry, I can’t make it.” Or, frankly, I think I was the one doing a lot of the inviting back then.

Tim Ferriss: Interesting. Okay. Right. You were doing a lot of the — 

Jason Portnoy: Because that was a badge of honor was 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 had to stop, just stop, period, and be more still. And that’s hard to do.

Tim Ferriss: So how did Melissa sell this to you? Right.

Jason Portnoy: Well, she said, “You’re efforting your way through life.” And I was just livid. I was like, “What are you talking about? 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. Hitting me in the core. And I remember one time she was telling me this, and I was like, “Well, I can’t just sit on the couch and meditate. Monks don’t have mortgages.” And then she cracked up. I should have gotten a t-shirt with that on it. Monks don’t have mortgages.

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. So she said, “You’re efforting your way through life. I promise you there’s a way to create just as much abundance in your life, if not more, with much less effort.” And once I got through the fireworks of disagreement, I still didn’t believe her. I was like, “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’ve been. And so I was willing to try it and say, “Okay, let me try it.” And I did, and I started subtracting.

Tim Ferriss: Is there a particular process that she uses to aid you with that subtraction? Are there any filters you apply or are you just turned loose with the instruction to subtract?

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

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

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

Jason Portnoy: Yeah.

Tim Ferriss: What is the sort of default core.

Jason Portnoy: Yeah.

Tim Ferriss: So let’s introduce an acronym ESSAY: Not South Africa. Sexaholics Anonymous in this case. Where did that enter the picture? And did it enter the picture before or after you came clean with your wife about your side of things?

Jason Portnoy: Yeah, so her affair revelation comes in early 2010. We’re separated for a while. I never reveal what’s going on with me. We get back together after about a year and a half, and I’m on good behavior for a while. But then I start in with the bad behavior again. And in 2014, something happens where I 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, “I want to work on this porn habit. I don’t think it’s helping me. I think I need to get rid of it. I think I need to subtract it.”

And so I get caught in early 2015, and it’s pretty devastating. Because after everything Anne Marie and I had been through, she just started feeling like, “I don’t even know this person. Who is this person? There’s something he’s not telling.” And Melissa understood it, too. And I had kind of spiraled again into a place where I felt like I had kind of lost control of my life. And Melissa said on the phone to me one day, “We don’t believe you, and if you don’t share your secrets, you’ll stay sick. And if you want to move forward, you’re going to have to share your secrets.” And that’s when I finally came clean. That’s when the flood gates opened and I said, “Okay, it’s not the first time this has happened.”

She said, “How many times has this happened?” I said, “I can’t even count. I don’t know.” “How long has this been going on?” “Since I can remember.” It had 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.” And she was the one who suggested I check out a 12-step program, and that’s how 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.

Tim Ferriss: Place us in time, then. That was roughly when?

Jason Portnoy: That was February of 2015.

Tim Ferriss: And what has your participation looked like or attendance, I’m not sure the right term to use, since then?

Jason Portnoy: Since then. So at the beginning, I attended several meetings a day for weeks trying to find a meeting and a place and a group of people that really resonated most with me. And, frankly, it was a lifeline for me because when I revealed this stuff, I had to move out. This, again, is 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 a few meetings a week. And I probably did that for a year or a year and a half. And then our family moved. In 2017, we moved to Singapore for six months for my work and I stopped going to meetings.

And then when I came back, I didn’t pick it up again. And I 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. If anyone gets to a really, really bad, dark place, if you focus on those three things, you can climb out of that.

Tim Ferriss: One more time. Can you repeat those?

Jason Portnoy: 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, that’s the humility piece, was just so helpful and so important. Yeah. So that was — 

Tim Ferriss: You said there were two pieces.

Jason Portnoy: Yes. There were two pieces. And at this very moment, I can’t remember the second piece. I’m so sorry.

Tim Ferriss: No, that’s okay. It’s okay. We can come back to it. 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. You didn’t pick it back up, but I feel okay with that.

Jason Portnoy: I feel okay with that, and now I remember the second thing.

Tim Ferriss: That was my intention.

Jason Portnoy: Yeah, thanks for the reminder. So I feel like this addiction topic, it’s a huge topic, right? We could talk for an hour just about that.

Tim Ferriss: Oh, yeah. Many hours.

Jason Portnoy: And I feel like having gone through that experience, and so I often ask myself, I feel like the cultural narrative, a lot of times with addiction is 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 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.

Tim Ferriss: 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 whereas Dr. Gabor Maté would talk about asking: “Not why the addiction, but why the pain?” So people using — and 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. There are a million different ways. Could be an eating disorder. It could be you name it. 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 re-contextualize 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 — 

Jason Portnoy: 2017.

Tim Ferriss: You said 2017, at this point, are you guys still apart?

Jason Portnoy: 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, 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. So I shut down as much as I can, and I start reprogramming myself I guess. I start journaling very intensively. So I’m going to SA meetings at least a few times a week, I’m journaling very intensively, I stop 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.

Tim Ferriss: So monks do have mortgages.

Jason Portnoy: Monks do have mortgages in this case. Yes, and Melissa joked that at some point during that retreat that I was on, she was like, “I’m not going to call you Porn Star anymore. Now you’re The Monk.” And I really was living this kind of monkish life. I was just tuning everything out, only reading spiritual books, Autobiography of a Yogi was one of them, books by Emmet Fox.

Tim Ferriss: I don’t know Emmet Fox. I probably should.

Jason Portnoy: Oh, yeah. I like him a lot.

Tim Ferriss: Any starting point?

Jason Portnoy: I like The Sermon on the Mount, and there’s also a book called The Lost Booklets of Emmet Fox. And I’d say the biggest thing I take away from Emmet 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 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.”

Tim Ferriss: So Melissa was still engaged at this point?

Jason Portnoy: Yes.

Tim Ferriss: So while you’re — 

Jason Portnoy: I still talk to Melissa every week.

Tim Ferriss: Right. And during this aesthetic reclusive, I don’t want to say reclusive, maybe that’s not fair.

Jason Portnoy: Retreat.

Tim Ferriss: Retreat phase.

Jason Portnoy: Yeah.

Tim Ferriss: You were still engaged with her on a regular basis.

Jason Portnoy: 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.

Tim Ferriss: And 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.

Jason Portnoy: I changed everything.

Tim Ferriss: Yeah.

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

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

Jason Portnoy: Right.

Tim Ferriss: Compared to the person that you were, behaviorally speaking.

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

Tim Ferriss: And that was 2000 — 

Jason Portnoy: It was early 2015.

Tim Ferriss: Early 2015. At what point — just have some notes here. These are from your book, two books, The Seat of the Soul and then that first one is Gary Zukav.

Jason Portnoy: Zukav, mm-hmm (affirmative).

Tim Ferriss: Zukav and then Healing the Shame That Binds You.

Jason Portnoy: 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. And I read so many books during that time, but the ones that really stuck out were Autobiography of a Yogi, Emmet Fox’s books, and Glennon Doyle’s book Love Warrior.

Tim Ferriss: Love Warrior.

Jason Portnoy: And Love Warrior, you want me to tell you?

Tim Ferriss: Please.

Jason Portnoy: Yeah. Love Warrior, Glennon, if you haven’t read the book, she just shares her story and is very vulnerable. And I was in a very dark place and trying to figure out 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.

Tim Ferriss: How did you end up coming back together with Anne Marie?

Jason Portnoy: 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 was the same message. The message is the same for everyone. And she recommended a book to the two of us called Women Who Love Too Much by Robin Norwood.

Tim Ferriss: I’ve heard a lot about this book. I’ve never read it.

Jason Portnoy: It’s a great book.

Tim Ferriss: Yeah.

Jason Portnoy: 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 and 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. Addiction definitely does that to a person. And so it was actually 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’ve been very uncomfortable for her.

Tim Ferriss: Unfamiliar.

Jason Portnoy: Unfamiliar and uncomfortable. And so we read that book and it really changed the way we thought about everything that was happening. And she started to understand this as well, but she also got very clear with her boundaries. You need to start, you need to fix this, you need to climb out of this. I understand you’re on a journey, I understand you have work to do but if I ever feel like you’re not working and you’re not taking this seriously, then we’ll get divorced. It was that clear. And I was like, “Yes, ma’am. 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.

Tim Ferriss: So when did Melissa reach out to Anne Marie, or were they also having an ongoing — 

Jason Portnoy: Ongoing. Oh, yeah.

Tim Ferriss: — conversation.

Jason Portnoy: 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. 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 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.

Tim Ferriss: What have been some of the most important keys to the repair process? Repairing trust in both directions.

Jason Portnoy: Right.

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

Jason Portnoy: Yeah, it took a long time, more for her to trust me again.

Tim Ferriss: Yeah.

Jason Portnoy: It took time. It just took time.

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

Jason Portnoy: Yeah.

Tim Ferriss: That you had — and I’m not casting judgment here, but that you had kept your secrets while condemning her.

Jason Portnoy: Absolutely. That was horrible. It was just a horrible thing for me to have done. That’s what made it so devastating.

Tim Ferriss: Yeah. Were there any particular steps or any particular conversations, aside from time healing all wounds, which may or may not be true, maybe deliberate practice heals a lot of wounds, but what were some of the things that helped?

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

Tim Ferriss: Yeah, for sure.

Jason Portnoy: We still know what happened and we still — and it’s all been part of our journey and we appreciate everything that our journey has taught us, but those things still happened and they were still painful.

Tim Ferriss: What safeguards do you put in place? I’m just imagining. There’s ubiquitous high speed wi-fi everywhere, you have laptops, and if pornography on some level is the gateway drug that opens Pandora’s box, what are some of the rules and parameters or guide rails that you have for yourself?

Jason Portnoy: Sure, nothing technology related. So I don’t have special filters on my phone or anything like that. So 2015, this whole thing blew open. I moved back in midyear, 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.” Well, actually in the very dark first period, it was hard. But anyway, at some point it was like it just disappeared. It was off the radar and 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 called back to it. But this time I was really open about it with both Melissa and Anne Marie. I 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.

Tim Ferriss: Sounds very — yeah. No, it — 

Jason Portnoy: It takes all the fun out of it.

Tim Ferriss: Yeah, it de-sexy-fies the process.

Jason Portnoy: Absolutely. And so it has been that process. And so now 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 something happens. But when that happens — 

Tim Ferriss: Birthday. Morning of the birthday.

Jason Portnoy: No.

Tim Ferriss: Just kidding.

Jason Portnoy: 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 not right. And that becomes an entry point into my work. And so I don’t want to have filters or rules or anything like that. My belief as it relates to these kinds of things is if it’s calling me, there’s a deeper reason. And if I just avoid it, then I’ll never really understand what that deeper reason is.

Tim Ferriss: Not only that, but it strikes me that if you are suppressing, it’s probably going to squeeze out some corner of that box you’re trying to compartmentalize it into.

Jason Portnoy: There you go.

Tim Ferriss: And it’ll manifest in some other way.

Jason Portnoy: That’s right.

Tim Ferriss: Now, let me just play devil’s advocate though.

Jason Portnoy: Yeah.

Tim Ferriss: Sexual drive, very fundamental to human existence.

Jason Portnoy: Sure.

Tim Ferriss: And so 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 is not to get too super granular. But are you permitted or do you allow yourself to masturbate, and is porn-assisted masturbating a separate class? Because I do think those experiences are very different, as I think most men would agree. If you look at porn today versus porn five years ago versus porn 10 years ago, it’s like an arms race. It is so extreme and it just gets more and more extreme.

Jason Portnoy: It’s really just — yes.

Tim Ferriss: And it’s not all over the top, but a lot of it is so extreme that it desensitizes you.

Jason Portnoy: It’s very dehumanizing.

Tim Ferriss: It can be dehumanizing and it also, at the very least is — 

Jason Portnoy: Desensitizing, yeah.

Tim Ferriss: — desensitizing to the point that sex, any, even very exciting sex on any normal level really can’t compete in the mind with what you can get instantaneous online. It’s very, very challenging. Right?

Jason Portnoy: Right.

Tim Ferriss: So how do you think about any of that?

Jason Portnoy: Well, I agree. I think masturbation is a normal thing and probably I don’t have any specific issues with that. What I do think is very bad is porn 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.

Tim Ferriss: Yeah, I agree with that.

Jason Portnoy: I think it is hurting young women. I think it’s just bad, just all around. And I don’t think — again, yeah, so I think masturbation is fine, but I think anything with porn is not good.

Tim Ferriss: Yeah. Don’t put it on steroids with the porn assistance. Why do this book? Because these are subjects that most people would love to avoid talking about publicly.

Jason Portnoy: That’s a great reason to do it. There’s this — 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. I was sitting next to someone on a plane, this woman on a plane, it was a plane taking off from L.A., 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 — 

Tim Ferriss: Here we go.

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

Tim Ferriss: I think it’d be a tremendously powerful thing. I think I’m not that old, but I’m 44, 45. I forget. I’m getting old enough that I forget how old I am. That I’ve been able to see a whole cohort of my close friends get married, get divorced, get married, have trials and tribulations and all sorts of challenges. And I feel like the questions that you raise in this conversation, in the book, in your story, the challenges that you talk about are in many ways, in some form or another, ubiquitous. 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.

Jason Portnoy: It’s everywhere. And I say this in the afterward 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, starting to heal and then finding myself. Well, there’s some intermediate steps as well that you mentioned earlier. There’s the pain and then there’s the self-medicating to avoid the pain, and then there’s the 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.

Tim Ferriss: The Porn Star’s Journey.

Jason Portnoy: Yeah, As a Monk.

Tim Ferriss: It’s a good title. Monks Have Mortgages.

Jason Portnoy: Monks Don’t Have Mortgages. That’s right.

Tim Ferriss: I was just thinking about your retreat.

Jason Portnoy: Yeah.

Tim Ferriss: And the contrast. So the timeline that plays out in the book leaves us, I believe April, 2015. Is that right?

Jason Portnoy: August, 2015.

Tim Ferriss: August.

Jason Portnoy: Yeah.

Tim Ferriss: Okay, I was close.

Jason Portnoy: Yeah.

Tim Ferriss: I knew 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, surgery, a particular type of cancer treatment, a particular type of psychedelic therapy for, say, complex PTSD, where people hear these stories of redemption but sometimes mistakenly believe that everything is solved. And I think it’s sometimes helpful to set expectations that, “Hey, you’re still going to have to like row the rowboat and there’s probably going to be more work involved.”

Jason Portnoy: Well, it is a lifetime journey.

Tim Ferriss: Right.

Jason Portnoy: And you can never reach, 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, we like to use the metaphor climbing our spiritual mountain. So I’m climbing my mountain and there’s giant boulders blocking my path that I can’t get past and the only way to get past them is to crawl through some dark cave where there’s something really scary in there. And I’m scared. And so in the early part of the climb, it was like that. Once you get past those kinds of parts, it gets a lot more subtle. There was a whole phase after all of this stuff where I feel like surrender, I felt 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.”

Tim Ferriss: And could you just remind me what that means to you, to surrender? And maybe you have an example you could share. Any example where you’re like, “Okay, universes, I get it.”

Jason Portnoy: Yeah.

Tim Ferriss: This is time for me to surrender.

Jason Portnoy: I feel terrible that I’m not coming up with an example.

Tim Ferriss: I’ll tell you what.

Jason Portnoy: Right away.

Tim Ferriss: I think I could get us there laterally.

Jason Portnoy: Yeah.

Tim Ferriss: Can you think of a time where you were doing the opposite of surrendering? Just efforting the shit out of it?

Jason Portnoy: Yeah, maybe in my venture capital work.

Tim Ferriss: Okay.

Jason Portnoy: 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 putting so much effort into that. And then after it didn’t happen, after it didn’t manifest, and I know there’s a school of thought out there that’s like, “Well, that means you didn’t work hard enough and you just need to work harder next time, and so on and so forth.” But I took it as a sign of maybe this just isn’t the right thing for me.

Tim Ferriss: Yeah.

Jason Portnoy: 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.

Tim Ferriss: Yeah.

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

Tim Ferriss: Yeah. That makes me think of something that Seth Godin, the author, he 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 and I think impressive. And he, at some point, told this story of me of pushing boulders downhill instead of uphill, and he tells the story of this woman who’d been trying to sell some type of — I’m going to 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, a 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 less — 

Jason Portnoy: Least resistance. Yes.

Tim Ferriss: Of less resistance.

Jason Portnoy: And that’s been a concept for me over time too, this idea of conservation of energy. 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. And so because the first version is kind of a controlling version. It’s like, “I know what the answer’s supposed to be and I have to manifest that answer.” Whereas the second version is more of a surrender approach and saying, “I don’t know what the answer’s going to be. I’m going to move in this direction.” And I think that has served me well.

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

Jason Portnoy: No, no, it’s a good question. I still have a tendency to be in my head more than I would like. I would like to embody my body more than I do, but it does not come easily for me and I have to work at it. I think partly related to that, I probably have a tendency to make myself busy sometimes as opposed to just having a little bit more stillness in my life. And so I think to me, all that means is those are actually good things in my opinion, because those are entry points for the work. I feel like the most difficult times of this inward work and journey have been the times where I didn’t really feel like I had a good entry point.

Tim Ferriss: You don’t have enough grist for the mill.

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

Tim Ferriss: Is there anything that has stuck in particular from your retreat period, your four and a half months or whatever it was? Is there anything? Because you changed everything.

Jason Portnoy: Yeah, it changed everything.

Tim Ferriss: It was — were there any particular things that have stuck in part or wholly after that?

Jason Portnoy: 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?”

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

Jason Portnoy: They do.

Tim Ferriss: Okay.

Jason Portnoy: They do.

Tim Ferriss: 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. Let’s just say it’s not that, but you identify friend X and you’re just like, “Yeah, this has run its course.”

Jason Portnoy: Well, I think the — so — 

Tim Ferriss: What do you do then?

Jason Portnoy: What do you do? 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 leave the interaction not feeling good, 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.

Tim Ferriss: For sure.

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

Tim Ferriss: Yeah, agreed.

Jason Portnoy: If my mind is quieter and I’m picking that stuff up. And so where was I?

Tim Ferriss: So the question was let’s say you’re like, “Wow, this is not a full body yes to Joe. I need to get rid of Joe.”

Jason Portnoy: And so if you noticed that then I’m not sure I understand why it’s hard.

Tim Ferriss: Well, tell me what you do and then we’ll find out.

Jason Portnoy: I think you just let it go.

Tim Ferriss: Right.

Jason Portnoy: You just — 

Tim Ferriss: Okay. So you’re like, “All right, I don’t want to throw — there are probably a lot of Joes out there.

Jason Portnoy: We don’t want to throw Joe under the bus.

Tim Ferriss: Augustus. All right, Augustus. You’re like, “Augustus, every time I go to a barbecue with this guy, he invites me out for coffee. I come away and I just feel slightly drained.”

Jason Portnoy: Well, the next time you get invited, maybe you’re too busy to go.

Tim Ferriss: Okay. And then he invites you the next week.

Jason Portnoy: And then maybe you’re too busy to go.

Tim Ferriss: Okay. And eventually you hope that Augustus just gets the signal.

Jason Portnoy: Yeah, I think so. I mean, you could take the other approach, which is, “Hey, when we spend time together, I don’t really feel good afterwards.” That feels like a tall order. I don’t have the guts to do that.

Tim Ferriss: Okay. Got it. All right. So it’s the slow fade.

Jason Portnoy: I think so. I think these things just fade. And 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 that people are the most resistant to. They pride themselves on, “I’ve been friends with this person since kindergarten.”

Tim Ferriss: Right.

Jason Portnoy: It’s like a badge of honor.

Tim Ferriss: Yeah.

Jason Portnoy: But people change.

Tim Ferriss: Yeah.

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

Tim Ferriss: Let’s shift gears a little bit just to some broader questions, if that works for you.

Jason Portnoy: Yeah.

Tim Ferriss: 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 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, a word, a 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?

Jason Portnoy: Yeah. So this idea of climbing our spiritual mountain has just become so fundamental to our life that I would say something like, “Keep climbing your mountain,” or, “Don’t stop climbing.”

Tim Ferriss: Don’t stop climbing.

Jason Portnoy: Maybe, “Keep climbing your mountain,” or, “Just keep climbing.” That might be it. “Just keep climbing.” Yeah. There’s so many questions over the last — you said, “What have the last seven years been like?” And after those big boulders and caves, there’s more subtle stuff, but it’s still there. There’s still work. And there’s so many times I’d ask Anne Marie a question. “Should I do this or should I do that?” Maybe it’s a business question. It could be related to whatever. Usually a business question. And her response would be, “Just keep climbing.” And I’d be so frustrated and annoyed. I’d be like — 

Tim Ferriss: Yeah. You’re like — 

Jason Portnoy: “Okay, Yoda.”

Tim Ferriss: “Come on. I’m trying to make a choice here.”

Jason Portnoy: Yeah. Yeah, yeah. And then she 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 and sure enough it would resolve, or the answer would resolve itself. It would present itself.

Tim Ferriss: Yeah. 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?

Jason Portnoy: That’s Love Warrior, the one I talked about earlier by Glennon Doyle.

Tim Ferriss: Yeah. Glennon Doyle.

Jason Portnoy: The Power of Now by Eckhart Tolle. That book changed my life, blew my mind. If you’re going to read that book, take it slow in my opinion. I can’t tell you how many people I’ve met where they’re talking to me about some issue or problem in their life and I’m like, “You should read The Power of Now,” and they’re like, “Oh, I read it.” And I’m like, “No, you didn’t. You need to read it again. Because if you really read it, you wouldn’t be saying what you’re saying right now.” So those. There’s a book in 2018, maybe, really trying to let go of the shame that I carried. Because even after I was healing myself, I still had a lot of shame for a long time. I was very embarrassed about the things that I had done.

Tim Ferriss: So the shame was, just for my own clarity, was the pornography and the cheating — 

Jason Portnoy: The cheating. Yeah.

Tim Ferriss: — and so on.

Jason Portnoy: Yeah, absolutely. Very embarrassed, upset with myself, ashamed.

Tim Ferriss: Yeah.

Jason Portnoy: And there’s a book called Healing the Shame That Binds You — 

Tim Ferriss: Right. John Bradshaw.

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

Tim Ferriss: I’ve been meaning to read that for some time now.

Jason Portnoy: Yeah. It was very powerful.

Tim Ferriss: Let’s talk about investments, but not perhaps in the traditional sense. So, outside of the financial investments, can you think of a particularly any very good investment that you’ve made worthwhile? It could be time. It could be energy. Not to quote Warren Buffett, but I will. He talks about his best investment being investing in a Dale Carnegie speaking course, because it’s a multiplier for all of your other powers. That might be part of his “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?

Jason Portnoy: Absolutely. It’s hard to give these in order because they’re, tied for first place, I would say.

Tim Ferriss: Perfect.

Jason Portnoy: The investment. 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 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 with my kids. In fact, I feel like my kids — I often get asked when I tell people I’m kind of phasing out of being a venture capitalist, they’re like, “Well, what are you going to do? You’re just going to get bored.” I’m like, “No, I have two kids.” And helping launch two humans into the world is actually a huge responsibility. I don’t think we all appreciate sometimes how big of a responsibility that is. And investing in them and investing in my relationships with them has been the best investment, in addition to the coaching work. Those things. Someone asked me recently, “How do you define success for yourself?” It’s those relationships. That’s it?

Tim Ferriss: That’s it.

Jason Portnoy: Yeah.

Tim Ferriss: So if I may take us from the sublime to the ridiculous for a second?

Jason Portnoy: Please.

Tim Ferriss: I want to ask you about Microsoft Excel.

Jason Portnoy: Oh, sure.

Tim Ferriss: So, my God. All right. So I’m reading here. I want to see if this is any way ties in, because I’m also curious about the early investments. So this is from a Business Insider piece from God knows when. It was a piece called “Career Advice from Peter Thiel’s Mentee,” or at least that’s what they called it in the URL. Who knows what they ended up calling the headline. So: 

“On my first day at the company, nobody knew what I should do. A chemical engineering major who knew a little about business?

“It turns out that I did have one really valuable skill at that time: I knew a lot about Microsoft Excel.

“One of my undergraduate professors —

And this is where the name comes in: 

“Dr. David Clough — 

Jason Portnoy: Clough.

Tim Ferriss: — C-L-O-U-G-H. 

“…had insisted that we all learn a lot of the more powerful (and sometimes obscure) features of Excel.”

Jason Portnoy: Yes. So when I got to PayPal, yeah, I was a finance major. I had been a chemical engineering major. And then I was in this kind of quasi-finance business graduate degree program. And like I said earlier, the focus was not on hiring necessarily a specific skillset. It was — 

Tim Ferriss: General capacity

Jason Portnoy: — 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.” And so I went in and the first day I was like, “What should I do?” And the accounting controller 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. What? What? Who are you?” And so anyway, I started doing some stuff in Excel, tracking metrics, basically, because there was this daily report that would come out of the system and I started keeping track of it every day and then sending around graphs to everyone. And I was just good with Excel and that kind of launched my career at PayPal. So I have a lot of gratitude for professor Clough and I owe him a lot.

Tim Ferriss: So he was a professor of what?

Jason Portnoy: He was in the chemical engineering department at University of Colorado. And as I, again, mentioned earlier, in chemical engineering you have 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.

Tim Ferriss: So here’s a question I’ve never actually had a chance to ask anyone, and it just occurred to me I should probably ask. So I don’t know a lot of CFOs or people who have been CFOs. 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, thinking of someone in your mind of someone who’s a superstar CFO and what differentiates one from the next.

Jason Portnoy: Oh, sure.

Tim Ferriss: Because I can think of CFOs and you have all these different archetypes, right?

Jason Portnoy: Mm-hmm (affirmative).

Tim Ferriss: But then in the CFO category, right? Even CMO, I can imagine certain things. But I’m certainly not a mathematician. I’m certainly not an accountant. I don’t even begin to understand or I can’t pretend to understand what a CFO does day-to-day. So I don’t know what differentiates one from another, right?

Jason Portnoy: Mm-hmm (affirmative).

Tim Ferriss: Because I’m like, “Well, all right, you got first in, first out. You got some accounting principles. You got to make sure you behave on some level for the SEC in certain circumstances.” I’m like, “What differentiates them?”

Jason Portnoy: 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 skillset than the CEO of PayPal.

Tim Ferriss: Or the CFO.

Jason Portnoy: Oh, sorry. The CFO. The CFO. The CFO of a company that’s building airplanes or something else is different than the skillset 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 want to be the C-level. So I’m the VP of finance. I want be the CFO. I’m the VP of marketing. I want be the CMO. What separates the VP from the C-level? In my opinion, the shorthand I give them is that the C stands for confidence. And it’s not necessarily that the CFO knows more about the technical accounting or the technical financial analysis or the treasury function or whatever is happening.

But there’s something about the energy that they carry, whether that comes from experience or it’s just innate to them, but there’s something about the energy they carry that when they walk in the room, it inspires confidence. And I think that’s the key. 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 to be obsequious. He was amazing. His name’s — 

Tim Ferriss: Who?

Jason Portnoy: His name’s Roelof Botha.

Tim Ferriss: Oh, yeah?

Jason Portnoy: He’s now the head of Sequoia Capital — 

Tim Ferriss: Sequoia.

Jason Portnoy: — globally. So it’s not a fluke. He has been exceptional his entire life. I mean, I didn’t know him when he was younger before PayPal. We actually, funnily 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, I mean, priceless contribution. He was amazing, and he’s just a great human.

Tim Ferriss: Yeah. He’s a very, very bright guy. I maybe met him once in 2009, like “Hello, goodbye” kind of thing in some God knows what Silicon Valley event, but — 

Jason Portnoy: He’s busy.

Tim Ferriss: Oh, yeah. But I’ve heard so many good things — 

Jason Portnoy: Yeah. He’s brilliant.

Tim Ferriss: — about him. What are some of the other things that you observed in him or learned from him? You said a great boss. What made him a great boss?

Jason Portnoy: I was so young. It wasn’t just he taught me so much about finance, but he also — 

Tim Ferriss: May I ask a silly question?

Jason Portnoy: Yeah, yeah.

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

Jason Portnoy: 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, Roelof 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 — 

Tim Ferriss: If you tweak this cell.

Jason Portnoy: Based on certain assumptions.

Tim Ferriss: Right.

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

Tim Ferriss: Oh, that’s a gift. A gift.

Jason Portnoy: 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. 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, 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.

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

Jason Portnoy: Absolutely. Yes, yes, yes.

Tim Ferriss: PayPal had a lot going on.

Jason Portnoy: We had a lot going on. Yeah.

Tim Ferriss: Oh, man. What an exciting journey you have had. Of course, with the bad with the good and the down with the up. But nonetheless — 

Jason Portnoy: 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.

Tim Ferriss: Okay. So closing question-ish. I always caveat that, because I’m prone to saying, “Last question,” and then a half hour later we’re still going. Men and women listening. Or if I want to be a little less, what is it, cisgendered, just people listening who are in relationships, committed relationships, and they think to themselves, “I should have a conversation about this with my partner.”

Jason Portnoy: Oh, I hope they do.

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

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

Tim Ferriss: Yeah. An alliance.

Jason Portnoy: — maybe survival necessity in the various or earliest days. And then it was alliances and political stuff. And then it was love. 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 a mutual commitment to each other’s spiritual growth. And so when you’re in that relationship, if you can take yourself out of it for a moment and say, “We are two souls moving through this lifetime together and we’re both learning lessons. What are these lessons? How can we learn from each other? How can we help each other?” 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, right? 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 relationships that maybe shouldn’t proceed, especially if there’s abuse or something like. That’s very serious. But I do think in our modern society, there is a tendency to pull the rip cord pretty early.

Tim Ferriss: 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 and we’re talking about your story, let’s just say it’s a male who has issues with porn, maybe it’s gone beyond porn, who 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, and then have that conversation?

Jason Portnoy: Well, if you’re in a relationship my first reaction is — and it’s hard. I try to be careful to generalize.

Tim Ferriss: For sure. For sure.

Jason Portnoy: Because I know what worked for us, but it doesn’t mean it would work for everyone, you know?

Tim Ferriss: Yeah.

Jason Portnoy: But the way it unfolded for us was that we had this third party intermediary, a 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. You’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.

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

Jason Portnoy: Oh, right, right, right.

Tim Ferriss: Yeah. Don’t be shocked.

Jason Portnoy: “Do you look at porn?”

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

Jason Portnoy: Well, I mean, aside from potentially trying to find someone who can be a trusted third party intermediary that can help you hold space for each other, I mean, my other recommendation is that my healing, again, it’s hard to generalize, my healing started when I finally started to reveal my secrets. And I feel like the sooner, the better. So, 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.

Tim Ferriss: Well, Jason, you can be found at jasonportnoy, P-O-R-T-N-O-Y dot com. That’s for the general departure point for all good things. The new book, Silicon Valley Porn Star, which is easy to remember so you have that going for you with the book, is 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?

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

Tim Ferriss: Perfect way to end. Jason, thank you so much for sharing your story and taking the time with me also. This has been an enjoyable conversation, an enlightening conversation. I’ve taken a lot of notes myself. I’ve highlighted a number of different books, including your own. And I think that by writing this book, by having these conversations, you will do a lot of good.

Jason Portnoy: Oh, thanks.

Tim Ferriss: Because as we covered earlier, these types of challenges are ubiquitous. The conversations may seem few and far between, but the challenges, the issues, 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.

Jason Portnoy: Well, I appreciate you saying that, and I really appreciate you using your platform as a venue to do that.

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

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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