[00:00] Jason Portnoy: She had gone out with her friends after we had been together and her mother didn’t know where she was, but somehow through phone records thought that she was with me and I didn’t know where she was. And it was very scared cuz I, strange woman calling me and basically threatening to come after me. I had to tell my wife, that is a longer story.

[00:19] Jason Portnoy: I go through it in the book, but I had to tell my wife about it. And that was the beginning of.

[00:28] Jim Harshaw, Jr.: Welcome to another episode of Success Through Failure. This is your host, Jim Harshaw, Jr. and today I bring you, Jason Portnoy. Jason grew up in the suburbs of New Jersey and pretty much followed the script that you’re supposed to follow, right? He strove for success, you know, went to Stanford, and then eventually found himself in Silicon Valley in the middle of what’s called the PayPal Mafia.

[00:52] Jim Harshaw, Jr.: And he, you know, worked early in his career with visionaries like Peter Teal and Elon Musk and Max Le and Reed Hoffman, and a lot of other sort of visionaries and big names of Silicon Valley and the tech world. And this kind of launched him into this Silicon Valley career and life of wealth and prestige that he really never even dreamed of grown up.

[01:14] Jim Harshaw, Jr.: You know, he had stock options in PayPal and flashy cars in this amazing family that on the outside everything looked perfect, but on the inside he had unhealed traumas from his past that left him tortured, and he just ascended into this dark world of pornography and sex that eventually pushed him and his life and his marriage to the edge.

[01:33] Jim Harshaw, Jr.: And in his book, “Silicon Valley Porn Star,” he shares this personal transformation from a life. Affairs and just superficial access to one of living through his values and renewing relationships. His journey is fascinating. He shares it in our conversation today, as well as in his book. This journey just really sheds light on a crisis of masculinity in our own world where so many men quest for unlimited power and success.

[02:03] Jim Harshaw, Jr.: And these are gateways to addiction and dependency and just unhinged behavior. So no matter your profession or your position in life, Jason’s story is gonna inspire you to look inside of yourself and find your own path to success and fulfillment in becoming the person that you truly want to be. Give this episode a share.

[02:22] Jim Harshaw, Jr.: That’s how this thing grows. This podcast, I get amazing guests like Jason, his agent actually reach out to me for this episode, for this interview, but we can. Get these great guests because you share the podcast. And podcasts grow by word of mouth. So if you could give it a retweet, give it a share, tell a friend to check out the Success Through Failure podcast.

[02:42] Jim Harshaw, Jr.: Thank you in advance for that. Now let’s get to our interview with Jason Portnoy. You had this incredible rise through Silicon Valley. You started working at PayPal and you got to work with these entrepreneurs who went on to be what we know is visionaries today. You know Peter Thiel, Elon Musk, Max Levchin, and Reid Hoffman.

[03:02] Jim Harshaw, Jr.: What was it like working with those guys and tell us about that sort of meteoric rise you had in the tech.

[03:07] Jason Portnoy: It was pretty intense. If I had to use one word that comes to mind when I think about all of those guys, it was intense in a lot of cases. They were, they were also always working on multiple projects, which I thought was interesting.

[03:20] Jason Portnoy: And they were learning from one thing and applying it to the other thing. Not all of them, and not all the time, but that was something I observed. But they were also just very intense, very focused, even if they had multiple project. They were giving those things a lot of time and attention and not really putting much time and attention to other places.

[03:40] Jason Portnoy: So it was very intense.

[03:41] Jim Harshaw, Jr.: So I’m a coach and I help people kind of, you know, set goals in multiple areas of their lives and try to live balanced successful lives. Like would you say these guys were like out of balance? I mean, are they sort of forsaking their home life for their work and their business?

[03:57] Jim Harshaw, Jr.: Are they not working out? Are they kinda. Single minded focus or did you see that some of them were, were different and maybe more balanced than others?

[04:05] Jason Portnoy: Well, I know, and even speaking for myself during those years, I was way out of balance and not just because of the things I wrote about in my book, but I do think that by that measure of balance, they probably were kind of out of balance and would take a more temporal view of balance, meaning I might be out of balance.

[04:27] Jason Portnoy: This year and next year, but I’ll be able to recoup some of that the following year when this project ends and before I start the next project or something like that. I mean, I, I can’t speak for these guys, but I don’t think they think in terms of, you know, am I balanced? Am I not balanced? They don’t even, I think, pause to think that it’s just go, go, go, go, go.

[04:50] Jason Portnoy: And I don’t mean that as a criticism, it was just an observation.

[04:53] Jim Harshaw, Jr.: Yeah, well these guys are making dents in the universe. I mean, and that’s kind of what’s required.

[04:57] Jason Portnoy: I would think. Yes. It’s hard to do. It takes a lot of work. I mean, I don’t know if anyone works harder than those four guys you mentioned. Did you

[05:07] Jim Harshaw, Jr.: know, or did you have any inkling in the early days before these guys where you know, were the big names that they are today or later became, did you have an idea that these guys might go on to do

[05:18] Jason Portnoy: huge things?

[05:19] Jason Portnoy: No. No, no. I mean, there was a moment when I was at PayPal where I started there working part-time when I was a graduate student and when I started, we. 15 or 17,000 PayPal accounts, and that was in January. January, 2000. And by March we had a party at the office when we hit a hundred thousand users. And then we had another party when we hit a million users, which is like very shortly after we hit a hundred thousand.

[05:48] Jason Portnoy: And I remember it was one of those parties, I looked around the office and I was like, this is an amazing group of. and I think I should drop out of school and work here. And that was kind of that pivotal moment where I was like, I think I should be here cuz I can always go back to school. So there was something special about it, the people and the culture.

[06:10] Jason Portnoy: But no, I mean, when I was working very closely with Peter and Elon and Reed and Max, I didn’t know. Elon was gonna become one of the most legendary entrepreneurs, certainly of our generation. Right. It’s kind of been fascinating to watch how everyone’s grown and changed. So you had tremendous success there.

[06:32] Jim Harshaw, Jr.: I read a quote from Mike Tyson and he said that the best three years of his life were actually in prison. He said he could have gotten 30 million for a fight, but he’d be willing to just give it all away, to get back his balance and his peace. And this is the quote he said, that she said, God punishes you by giving you everything that you want to see if you can handle.

[06:53] Jim Harshaw, Jr.: Do you feel like you got everything that you had wanted

[06:57] Jason Portnoy: at that time? Yes. And that’s such an interesting quote. And by the way, when I hear a story like, oh, he left 30 million on the table, and that seems crazy. Well, if his net worth was $300 million, then maybe that’s not so crazy. So you always have to keep that in context.

[07:14] Jason Portnoy: But I think that when I hear that quote, it makes me think about what I experienced because I did get everything I. And what I wanted when I was a young man was more money, faster cars and hot women. Like I thought that those things were gonna make me happy and a real man, and so God or the universe or whatever, gave me those things.

[07:39] Jason Portnoy: And when I got those things, I was miserable. And so it’s interesting to hear that quote from him. When I hear to see if you can handle it, I feel like what he’s talking about there is you get everything you want and then you realize you’re still not happy. This happened with, uh, I think Andre Agassi famous tennis player, you know, at the height of his career, realizing it didn’t change who he was as a person and he wasn’t really happy.

[08:08] Jason Portnoy: And so I, I think that’s interesting.

[08:11] Jim Harshaw, Jr.: And so how did you handle it? You know, there’s porn addiction and that led to sex addiction, kind of, you know, you went down a dark path. How did that start and walk us down that path if you could.

[08:21] Jason Portnoy: Yeah, sure. So for me, I started looking at online porn when I was in college, when I got my first laptop, and you know, continued doing that into my twenties, late twenties.

[08:35] Jason Portnoy: And when I was working at PayPal and I started to make some money and it kind of went to my head. And kind of expanded my ego and I felt like, well, I’m a young man now I’m making some money. I feel entitled to whatever it is I want in the world, whether it’s cars or women or whatever. And. I feel like I didn’t handle it well.

[09:00] Jason Portnoy: I don’t feel like I had a very strong foundation. And so, you know, as I started making money as a young man, I feel like I just kind of went off the rails and chased after these things that I thought were gonna make me happy. And as I started doing that, I had a girlfriend who then became my fiance, who then became my wife.

[09:21] Jason Portnoy: And I started, you know, first with the porn and then with the hookups and the cheating. And I started to develop a lot of guilt and a lot of shame around those things. And the way I handled that was to just go deeper into the porn, deeper into the hookups, to numb myself from feeling those feelings of guilt and shame.

[09:44] Jason Portnoy: And to distract myself from feeling those feelings. And that’s how I wound up in this very addictive cycle that I kind of write about in my book.

[09:52] Jim Harshaw, Jr.: Yeah. This, this shame cycle you talk about. Can you take us to a moment? Like, was there a moment where you felt like it was rock bottom or you really knew this is a major problem?

[10:06] Jim Harshaw, Jr.: Can you take us to a moment that was like maybe your darkest place?

[10:10] Jason Portnoy: There’s two that come to mind. Well, one felt very dark at the time where my daughter had been born and we were all home. I was home on paternity leave. And leading up to this point, I had been engaging in affairs and hookups and things like that, but I tried to turn all that stuff off.

[10:30] Jason Portnoy: I felt like I’m a dad now. I need to clean up my act, I need to change, and all of those things. And I was on paternity leave and I was home. And the vibrancy of being present was just too much for me because again, up until that point, I had just been spinning like a top, so I didn’t have to connect with anything or anyone.

[10:53] Jason Portnoy: And I left my apartment and I went and hooked up with an escort. And when I went home, I felt something change inside of me. I was so disgusted with myself. It was the first time I think I felt truly disgusted with myself. It was like, this is a new low and you have a problem and this needs to change. So that was one.

[11:15] Jason Portnoy: It turns out I did change a little bit. Things got a little bit better for a little while, but years later, I, and I still hadn’t resolved the root causes of these things. I started in with my bad behavior again, and it was later around 2015, early 2015 when I got caught cheating and I had to come out and tell my wife that, you know, this wasn’t the first time and it was really devastating for our relationship and I had to move out.

[11:49] Jason Portnoy: I thought we were gonna get divorced. I thought I was going to harm my career. And so that was at risk and I was in a really dark place at that moment. I was very scared and very confused. Very disoriented, I think is another word. What

[12:05] Jim Harshaw, Jr.: happened? How did you get caught? What, uh, was the circumstance? If you don’t mind sharing.

[12:10] Jason Portnoy: Well, I get into something with the receptionist from the gym where I’m working out, and she is a young woman who still lives at home with her mom, and I get a phone call from the. Saying, well first of all, she says, where is my daughter? Because she had gone out with her friends after we had been together and her mother didn’t know where she was, but somehow through phone records thought that she was with me and I didn’t know where she was.

[12:39] Jason Portnoy: And it was very scary, cuz I. Was a strange woman calling me and basically threatening to come after me. And so that was very scary. And then I had to tell my wife, that is a longer story. I go through it in the book, but I had to tell my wife about it. And that was the beginning of the end.

[12:58] Jim Harshaw, Jr.: Quick interruption. Hey, if you like what you’re hearing, be sure to get the notes, quotes, and links in the action plan from this episode. Just go to JimHarshawJr.com/action. That’s JimHarshawJr.com/action to get your free copy of the action plan. Now, back to the show. So you mentioned that you hadn’t resolved the underlying causes, the root causes that first time. What were the root causes?

[13:26] Jason Portnoy: I’m not even sure I understand today, all the root causes. I feel like this is a journey of like peeling an onion. You know, there’s just layers and layers and layers and layers. But I do feel like I have peeled enough layers to feel like there was some traumas in my childhood that really affected.

[13:47] Jason Portnoy: My parents got divorced when I was young, five years old or so. My father left and moved across the country and I really didn’t see him much. And then when I got into like middle school years and a little bit before that, my mother started to battle with depression and was. Either gone in hospitals or home in bed, or kind of walking around a little bit like a zombie because of all the medication that she was on.

[14:16] Jason Portnoy: And so then my mom kind of left my life. I had a stepfather who helped take care of me, but my dad and my mom kind of left. And that really affected me and I didn’t understand how much that affected me until I got into my thirties and started trying to unravel like, well, why am I doing these things? And really, I was trying to fill some kind of hole inside of myself.

[14:42] Jason Portnoy: Maybe when a primary caregiver leaves, it’s very traumatic for a child. This is not controversial anymore to say. And you know, I don’t want to go into all the ways the mechanics exactly of how it affects cuz I’m not a doctor. But it left a hole in me and I was trying to fill that hole through validation from society.

[15:05] Jason Portnoy: Or, you know, trying to get love from these women that I was hooking up with or trying to numb that pain through pornography. And that’s how I got into those cycles was, you know, trying to fill that hole. And so what I had to learn. Was that the way to fill that hole or that gap was to give myself that love that I felt like I was trying to get from the outside world.

[15:34] Jason Portnoy: That validation, and that really is the core of the journey that I went on, which becomes kind of a spiritual journey that’s, uh, this recognition that of not just a brain and a body. There’s a spirit or a soul that exists that animates me that I need to build a relationship with. And once I started doing that, then the desire for all of these things just fell off, you know, no more desire to try to get that validation from society or numb myself from pornography and things like that.

[16:10] Jim Harshaw, Jr.: And so your wife finds out, how does she respond? Obviously not well, but tell us about. How that felt and how those, you know, ensuing days and weeks went, I felt

[16:23] Jason Portnoy: horrible. She was devastated because there had been a time prior to this darkest time where we had separated and tried to get more honest with each other, and we came back together, and then sometime later I reveal that I still had all these secrets that I hadn’t shared.

[16:47] Jason Portnoy: Even when we went through a kind of a rough patch in our marriage.

[16:51] Jim Harshaw, Jr.: So you had shared some secrets, but not everything.

[16:54] Jason Portnoy: I hadn’t shared any secrets in that first period. And to talk about that first period, you know I mentioned there was kind of like a mini dark period where I had this feeling of disgust with myself shortly after.

[17:09] Jason Portnoy: Or maybe six months after that, I quit my job because my marriage was kind of falling apart. At that point, I quit my job and about six months after that found out that my wife was having an affair. and that’s when we separated the first time and I played the victim and said, oh, you know, woe is me. She’s gone out and done this thing.

[17:34] Jason Portnoy: I haven’t done anything wrong. Or maybe I was just working too much, but I never shared all the stuff that I had been doing. And so then when we got back together and then some years later, You know, I get caught and have to reveal that I had been cheating all along the way. It was just devastating. I mean, I don’t know how, how else to say it.

[17:53] Jason Portnoy: It was just devastating for her and very difficult. And you

[17:57] Jim Harshaw, Jr.: worked with a coach named Melissa. What was her role in your healing?

[18:04] Jason Portnoy: Well, she is pivotal role. I started talking to her. Right around the time that I was kind of, I was quitting my job and trying to repair things with my wife, Ann Marie, and she was the one who started to introduce me to this idea that there is a spiritual side of me or a soul animating me that I needed to build a relationship with and that I had been neglecting that.

[18:32] Jason Portnoy: She also introduced some other concepts that were very helpful, like simplification. You need to simplify your life. Another major concept was secrets. Like we all hear this, like secrets will make you sick or something like that. But she really went after that very, very hard. And the first session I had with her, my homework was to write down all of my secrets.

[18:57] Jason Portnoy: And I remember I looked at her thinking. Oh my gosh, how does she know I have secrets? How, how does she know? And she, and it was like she was onto me from the beginning. And yeah, so those were kind of three of the primary things. And it was through working with her that we started peeling all of these layers of the onion.

[19:17] Jason Portnoy: And you know, I kind of believe, cuz it took some time, and I’ve been working with her for four or five years before I got kind of caught and had the real. Moment where I had to really change and I feel like all that work was just preparation. Cause it was kind of like my soul or my spirit wanted me to get caught and knew that the only way for me to move forward and to really heal was to acknowledge what was going on below the surface was to get cut and to bring all that stuff that was in the dark out into.

[19:55] Jason Portnoy: and she was just instrumental on helping me get to a place where I was ready to do that. And then once I got there and I was in that rock bottom moment, she was so instrumental in helping me rebuild my relationship with myself. Like who am I?

[20:10] Jim Harshaw, Jr.: And she also worked with Ann Marie, right? Your wife.

[20:13] Jason Portnoy: Yes. So it’s unusual, I know for people to work, you know, to have a coach or a therapist that’s working with both sides of the relationship.

[20:22] Jason Portnoy: But it worked for. And having that shared vocabulary helped Ann Marie and I stay in communication, talking with both of us, helped Melissa understand both of us, and really connect dots around what’s really happening. And we still talk to her every week, both of us, not together separately, but over the years.

[20:46] Jason Portnoy: We have had times where we’ve had, especially back then when we were really in a mess, at trying to untangle all this stuff. We had a lot of joint sessions and that was really fascinating and sometimes it’s just sitting and listening to that other person process something. It was fascinating for both of us. A lot of tears. It was amazing.

[21:08] Jim Harshaw, Jr.: What do you say to the person who doesn’t work with a coach? Doesn’t see a therapist. My wife and I have a marriage therapist and it’s just, So amazing to have that resource in our lives and in our marriage. What do you say to the person who doesn’t have that person or those resources in their life?

[21:27] Jason Portnoy: I feel so strongly that they should, I can’t emphasize this enough. I think modern life is complicated. We used to live in these like different kind of social units. You like caveman days where you know, we had these tribes and there was mixed ages and there was different support systems and like so much of that is gone and broken down at this point.

[21:51] Jason Portnoy: And the modern world is complicated. We’re getting bombarded all the time with messages from people who have commercial interests that may not align with what’s really best for us. And those things can be very distracting. And I think it’s so important to have a place, a person you can talk to who doesn’t have an agenda on you.

[22:17] Jason Portnoy: And that’s, I think, the most important thing. So you can talk to your spouse, but your spouse wants to remain your spouse probably, hopefully. And there’s an agenda there. It’s like there’s a limit to where that conversation can go because of that. It’s the same with a. A friend wants to stay your friend.

[22:35] Jason Portnoy: And so there’s a limit to where that conversation can go and finding a coach or therapist, especially one who doesn’t need you in their practice, because they have a very successful practice. And so they don’t have an agenda of like, I need to keep you as a client. And certainly that’s Melissa’s case, who’s got people, you know, banging down her door.

[22:54] Jason Portnoy: So she’s gonna tell it like it is. She’s gonna hold me accountable, call me out on my bullshit, push me out of my comfort zone. Um, in ways that a friend or a parent or a spouse won’t, and I think it’s so important to have that person to do that.

[23:11] Jim Harshaw, Jr.: And she would tell you, and, and she told this to Ann Marie, also, you’ve said that you are responsible for the circumstances in your life.

[23:20] Jim Harshaw, Jr.: Like, ouch. You know, like, I don’t think a lot of people are ready or willing to hear that, but you listen and you embrace.

[23:28] Jason Portnoy: Yeah, I did listen. I, and not, maybe not at the very beginning, but eventually I did begin to internalize that and agree with that. And there’s an interesting thing about this though, is you said a lot of people aren’t willing to accept that, but there’s two layers of it.

[23:45] Jason Portnoy: And so it’s even like doubly hard to accept, which is there’s a surface level of what I think I want. and what I think I’m doing that’s affecting the circumstances of my life, but there’s a subconscious layer of what I don’t even realize that I want and what I don’t even realize that I’m creating in my life for reasons that I don’t even understand because there might be some buried trauma in.

[24:16] Jason Portnoy: That’s causing, you know, these things to manifest. Or there might be some buried fear in there that is again, causing these things to manifest in our outside world. And so, yes, her message was you are responsible, and it might be something that you’ve consciously done and it might be something you’ve subconsciously done, but in either case, I’m gonna help you figure out why you’re doing it so that you can make a conscious decision.

[24:45] Jason Portnoy: To change it. And more often than not, I think it’s the subconscious stuff that we don’t even understand is affecting our behaviors and our life circumstances. And so that was a big part of the work with her, was trying to turn off that conscious brain, start digging into that subconscious stuff, bringing it up to the surface so you could address it again consciously, and then letting it go back down in kind of a different form.

[25:13] Jason Portnoy: And it was really fascinating work. I, I can geek out on this stuff, but it was fascinating.

[25:19] Jim Harshaw, Jr.: There’s a great quote, one of my favorite quotes is, until you make the unconscious conscious, it will control your life and you will call it fate.

[25:25] Jason Portnoy: Perfect. That’s exactly right.

[25:28] Jim Harshaw, Jr.: It captures it right? Because, you know, we all live these lives and we have these default modes that we operate on, and they’re based off of formative experiences and, and all of the experiences and knowledge and inputs we had had in our lives. And so we don’t know. We don’t know what we don’t know. We don’t know. The water that we swim in is different than the water that the next person swims in cuz it’s just all around us and we don’t, we can’t tell.

[25:56] Jim Harshaw, Jr.: I came across a great quote just yesterday by I was a friend of mine, Michael Chandler. He’s a UFC fighter. He said A man or a woman cannot consistently perform in a manner that is inconsistent with the way they see themselves. and that is like this inner work that we all have to do on ourselves regardless of where we’re at, right?

[26:20] Jim Harshaw, Jr.: Is to understand I’m here where I’m at and, and we all have somewhere where we want to go, right? Goals, you know, whether it’s career, relationship, health, some mixture of that. And if we want to perform in a manner that’s inconsistent, With the way that we see ourselves, we’re not gonna be able to do it very long until we do this deep work that you’ve done, Jason and that Anne Marie did.

[26:45] Jim Harshaw, Jr.: And like when you do this kind of deep work, then you can make real change.

[26:50] Jason Portnoy: So not only that, but you were saying, you know, we all have a goal. Like maybe it’s career, maybe it’s relationship, maybe it’s something else. What I have experienced. is that if I make the internal work, which I refer to in my book as climbing my spiritual mountain, but we can call it the internal journey, the internal work, whatever, personal growth work, whatever.

[27:16] Jason Portnoy: What I found is that if I make that my primary goal, all of the other goals almost, I won’t say they don’t matter, but they almost don’t. Because if that is your primary objective is to grow in consciousness, grow in understanding, grow in the depth of knowing yourself, grow in love for yourself. What I have experienced again is that everything else in my life has fallen into place professionally, relationship-wise, you know, my health, everything.

[27:55] Jason Portnoy: That it turns out that’s the core. And so even if you have goals, like whether they’re career goals or thing goals like a car or house or whatever, or relationship goals, those goals are based on your current level of consciousness. And so if you focus on trying to change your consciousness and you know, continue to elevate your conscious, those goals will also start to change.

[28:24] Jason Portnoy: So when I say everything falls into place, it doesn’t necessarily mean you start getting all the things you wanted because a funny thing happens. You start wanting different things, and certainly that’s what I experienced. That’s a good segue back was once I started doing this internal work, I didn’t want more money.

[28:42] Jason Portnoy: I didn’t want more cars. Mike Tyson started doing that internal work and realized, I don’t want more money. Like didn’t matter how much he had, he just knew he didn’t want more, and I think that’s interesting. I

[28:56] Jim Harshaw, Jr.: reflect back on my wrestling career at Virginia and my goal. For all my career had been to be an All-American, really to be a national champion, which is the top of the podium, but all-American is top eight and it’s sort of a mark of success.

[29:09] Jim Harshaw, Jr.: And I had wanted that so much and I did all of the things, like I checked all the boxes, like, you know, went to practice every day. I did extra practice every day. I showed up early, I stayed late. I rehabbed my injuries diligently. I watched film. I lifted weights with the team. I lifted weights extra. I got up early, I did extra conditioning.

[29:27] Jim Harshaw, Jr.: I ran my, like, everything, you name it, I did it. Except for the deep work, the mindset work. And once I finally started with working with a sports psychologist to sort of uncover what was actually holding me back, it’s not that like I need to do more curls or that I need to learn a new technique.

[29:46] Jim Harshaw, Jr.: Those weren’t the things like I. Been wrestling for a decade and a half. Like those weren’t the things, you know, you could certainly always improve on those, but the thing that I finally learned is that I was afraid of failure. Hence, you teach what you need, right? The success through failure, right? I still, like, this is still something I’ve, I’m always working to push away is this fear of failure.

[30:05] Jim Harshaw, Jr.: And I’ve internalized it at this point, but. Certainly at that point in my career, my wrestling career, I was just afraid to fail and I, I, once I finally uncovered that and was able to put that baggage down, it was free. And certainly I still wanted the goal, but I wanted that less. And what I really wanted to do instead was just to be the best version of myself.

[30:27] Jim Harshaw, Jr.: I just wanted to step on the mat and like let everything happen that could possibly happen and give my best. And walk off the mat and, and be satisfied in knowing that. And then look at the score and go, did I win or lose? Like relay? I, I wanted to focus on who I was and being the best version of myself.

[30:43] Jim Harshaw, Jr.: And gosh, when you can do that, the level of satisfaction that you can get in the world and in your life, regardless of what’s in your bank account or what awards are hanging on your wall or what place is next to your name in the, as a wrestler like. It just brings a joyful way of living. I never had so much fun wrestling as I did my senior year in college.

[31:07] Jason Portnoy: This is such a great story and I, I mean, I’m, I have this ear to ear smile for anyone who can’t see me right now. That is a beautiful story and also kind of brings home this idea also. at some point, like you said, you want, you still wanted those things and those things were still nice, but you wanted them less and you weren’t defining who you were by them.

[31:32] Jason Portnoy: And as you continue going, you know, deeper and deeper, eventually you start to feel like this whole experience we’re having it is, it’s kind of a game. Those models matter, but they don’t matter in the long run, right? The car I wanted so badly mattered, but it really doesn’t matter in the long run. What matters is that relationship with yourself, the relationship you have with your family, the joyfulness that you experience your life with, and being in service to.

[32:07] Jason Portnoy: And those are the things that it turns out that actually give us so much happiness, so much purpose, so much fulfillment. And when you have that and you’re happy, you know you’re gonna be successful at whatever it is you’re doing. The universe is going to provide whatever it is that you need, you know, to live, et cetera, et cetera. So that’s,

[32:30] Jim Harshaw, Jr.: So Jason, you made some serious changes. You said you made a ton of changes. You went to what you called retreat mode, and you said you changed everything. I’ve been curious, been really interested in asking you this question like, were those changes a means to an end, or did the changes happen internally and those were a result of the changes?

[32:51] Jason Portnoy: I do believe very fundamentally that if we want to change something in the circumstances of our life, We have to first change it inside of ourselves and then it will manifest in our external universe. You experienced this firsthand. You wanted to win more matches or have more fun doing what you were doing, and.

[33:13] Jason Portnoy: You did the internal work, you changed something inside of yourself, you let go of that fear and then it manifested as better performance. I’m very confident, like without even knowing your record, I’m sure

[33:25] Jim Harshaw, Jr.: you performed better. Yep. And I became an All-American. I became the thing that I actually wanted actually happened when I actually let it go.

[33:31] Jason Portnoy: So that’s how this works. That is the mechanism, uh, for how this works. I do feel like there are moments where the. Circumstances of our life are at such an extreme boiling point. You know, we have to set some rules and boundaries. We have to insulate ourselves. When a caterpillar is getting ready to turn into a butterfly, it wraps itself in a protective cocoon.

[33:59] Jason Portnoy: It insulates itself from the world so that it can go through its metamorphosis. And so in my case, I was so off balance. I was so far out of my integrity, right? Lying, cheating, the guilt, the shame, the embarrassment. I couldn’t stop. I was lost. It was just in such a dark place. I had to insulate myself. And so that’s why I moved out of the house.

[34:28] Jason Portnoy: I moved into a little apartment by myself. Uh, I shut down as much as I could professionally. I stopped talking to my friends. I stopped talking to my family. I changed what I was reading. I changed what I was eating. I changed the way I was exercising. I changed my sleep patterns. I mean, when I say I kind of changed everything, that’s what, those are the things I’m referring to.

[34:51] Jason Portnoy: And I just went into this retreat. My life coach joked that I was living like a monk and I kind of was, and that was necessary for me to go through. Some early period of my metamorphosis where until I could come out and stand on my own two feet, a little more sturdy. So I do think for people, again, if there’s something you want to change, like, uh, career, relationship, whatever, you know, you do some internal work and then the change will manifest in your life.

[35:25] Jason Portnoy: But if you’re in an extreme place, like an addiction that is taken over your life or something like that, Then you might have to insulate. For a while so that you can heal enough to get back

[35:40] Jim Harshaw, Jr.: out there. Yeah. And to put this into the wrestling context, it’s like I was doing all of the things externally that I needed to do.

[35:47] Jim Harshaw, Jr.: Like if I stopped going to wrestling practice and started hanging out, going to a book club instead, changing those external things wasn’t good. You know, I had to do the external things like go to practice, watch film, lift weights, show up early, stay late, and the internal work. So when you put these two together, then real change happens.

[36:03] Jim Harshaw, Jr.: So how did you rebuild trust? She found out about you. You also found out about her affair, and so how did you rebuild that

[36:11] Jason Portnoy: trust? So for me to trust Ann Marie again was, that was never a thing. I mean, she is an amazing woman. She’s so trustworthy. She was so honest about her affair and how she got into it.

[36:30] Jason Portnoy: And she did the work with Melissa to understand like why she got into it, how she got into it, what lessons she needed to learn from that experience. And then when it was over, it was a creation that she had to move through After that. It was never like, well, she’s gonna go have another affair. It was that thought.

[36:47] Jason Portnoy: Never crossed my mind. My thing was different. It took a long time for her to trust me again, but to be candid. I think the hardest thing was to rebuild trust with myself because I had been in a place where I was completely out of control and I had tried so hard to control my behavior, but then every single time would let myself down and quote unquote, fail.

[37:15] Jason Portnoy: Right. Like, I’m not gonna look at any more porn, and then I’d look at porn again. I’m not gonna do any more hookups, and then hookups again. And so all of that, until this kind of pivotal moment where I then went on retreat, lived like a monk and started to heal, I had to trust myself again and believe, you know, so I would say, well, it’s been, you know, X amount of time since I looked at porn or, or since I had a hookup, but it could happen next.

[37:45] Jason Portnoy: Or it could happen next month. This is, I’ve been in this place so many times where I thought I was past it, but I really wasn’t. And that took a long time. It took, you know, probably a solid two to three years almost to do that. Yeah.

[38:00] Jim Harshaw, Jr.: Where are you at today with all of this?

[38:02] Jason Portnoy: Well, I feel so lucky to have gone through this.

[38:09] Jason Portnoy: I know that sounds maybe weird, but. I feel so lucky that I was forced to start to build that relationship with myself and come to terms with, you know, any traumas from my past and how they might have been affecting me and raising my consciousness and all of those things, and learning this whole new vocabulary.

[38:30] Jason Portnoy: It’s been such an amazing journey and as we talked about earlier, the more of that work you do. The more you start to feel like an observer in the world and the more the things that you cared so much about, you don’t care as much about. And so I now find myself in a place where I feel very content with.

[38:52] Jason Portnoy: My life, my relationships, my professional work. I feel very content. And so what do you do when you’re content? You are in service to others. You can be in service to others. And I feel like that’s my job now. My job now is, you know, writing this book. I say it at the end of the book. I felt like it was my first significant act of service to share these messages.

[39:16] Jason Portnoy: There are a lot of men out there who are really struggling with this. and women who are in relationship with those men and women who are struggling with this as well. And so I wanted them to feel less alone and like there’s a path out of that dark place and have some hope. And then I also think it can be a cautionary tale for young men and women like, you know, this is what not to do. So that’s where I am.

[39:43] Jim Harshaw, Jr.: This book and, and your story, Jason, and you sharing, you’re being willing to share. This is such a powerful legacy and it’s, I’m just grateful that you’re sharing this with the world. Cause I think it’s gonna reach in, in touch and already has a lot of people. What is the success through failure lesson here?

[40:01] Jim Harshaw, Jr.: You went from incredible professional success to personal failure and I feel like you’re back to a place, at least from the outside looking in. Of success on both sides. What’s the lesson for the listener? The success through failure lesson for maybe for the listener who has failed or is failing. in some area of their life? Maybe along the lines like where you struggled.

[40:26] Jason Portnoy: Yeah, so I think one of the biggest lessons was that in my opinion now there is no distinction between personal and professional. It’s all the same. And even though I had by a lot of outward measures, some professional success, There were lots of ways I had underperformed professionally.

[40:46] Jason Portnoy: It’s kind of like you can’t run the experiment twice. So had I been in a different place, maybe I would’ve been even more successful professionally or something like that. And the reason I say that is that since I’ve gone on this journey, it has dramatically changed the way I operate professionally as well.

[41:05] Jason Portnoy: Not just in my personal relationships, but in my professional relationships. And I have been much more successful profess. So that goes back to that point. If you get the core right and you do that internal work, it affects everything and it kind of levels up your game in all aspects of your life because it’s all connected.

[41:24] Jason Portnoy: So that’s one point I wanna make. But to answer the question more specifically, like what’s the success through failure lesson failure. It’s a gift because the failure just means you are bumping up against the limitations of your programming. And so it’s a gift because it shows you where you have to start working to reprogram yourself and move past that hurdle.

[41:54] Jason Portnoy: you know that thing that is a failure. So it’s such a funny word because it has such like a negative connotation. I failed, I’m a failure, you know, all of these things. I went through a period where like I went through a long period where I didn’t look at any porn, and then it came back at one point a couple years ago and I was so upset and I felt like such a failure, and my life coach was like, no, no, no, no, no.

[42:20] Jason Portnoy: You are not the same person. You were two years. You’re such a different person. You have not failed. This thing is here to teach you something. Be happy it has arrived again, because now we have an entry point. And certainly that was the case. And it was so true, like it became a doorway to an entirely another level of growing. So failure is a gift. Maybe that’s the message. It’s a gift.

[42:47] Jim Harshaw, Jr.: I’ve been hosting this podcast a long time, Jason, that might be the best definition and explanation of failure that I’ve.

[42:55] Jason Portnoy: Yes. Oh, that’s awesome. That’s awesome.

[42:58] Jim Harshaw, Jr.: Are there any habits that you do that you feel have really kept you on track? Anything that you do on a regular basis that you feel really are keys to your success?

[43:10] Jason Portnoy: You know, aside from like trying to get enough sleep and eat pretty healthy and all of those things, try to get some exercise, all that stuff. But I think that I have been. Pretty open to taking risks in my life or going into like uncharted areas without a lot of certainty.

[43:32] Jason Portnoy: So an example would be like when I dropped out of college to go work at PayPal, it was like, I’m at Stanford University getting an amazing education. My parents were like, you’re gonna drop outta Stanford and go work at a startup. And this was like back before startups were a thing.

[43:50] Jim Harshaw, Jr.: Elon who?

[43:51] Jason Portnoy: Yeah, exactly, exactly. So, Being willing to do that, I think helped me when someone said, Hey, there’s this life coach I know who I think can be helpful to you. And I was like, I don’t even know what a life coach is, but sure, why not? I’ll go have a conversation. Well, that conversation changed my life and then the life coach telling me, you’re efforting your way through life.

[44:17] Jason Portnoy: You can create more abundance for yourself with less effort. And I was like, you’re out of your mind. But there was a part of me that was willing to listen to that and say, well, maybe she’s right. Let me at least explore it before I judge it and shoot it down. And so I think this willingness to explore uncharted territory, if I had to summarize it, has been really helpful for me.

[44:41] Jim Harshaw, Jr.: For the listener who. Has really bought into what you’re talking about here and your philosophy and, and is dealing with their own struggles. Maybe it’s addiction, maybe it’s something else. Is there an action item or one or two things that you might recommend that they can do, something they can do to start getting to a better place in their life in the next, say 24 to 48 hours?

[45:02] Jason Portnoy: Yes. If there is a person who’s struggling with some kind of debilitating thing, like an addiction or something like that, my strong advice is find a place where you can tell all of your secrets. That is when you will start healing. That is when. It’ll start getting better, and it’s probably not your spouse, your friend, your parent, your child.

[45:28] Jason Portnoy: It’s probably a therapist or a coach or a 12-step program. But find any place where you can let all of your secrets out, because when they’re inside of you and you’re not in your integrity, they’re like eroding you from the inside. So that’s a big one, is let your secrets. For someone who’s not in a, a critical place like that, but who’s just like, Hey, I, I like my life, but I want to be better at this, or I want more of this, or whatever, whatever.

[46:02] Jason Portnoy: I feel like simplification is probably one of the most important things for reaching those kinds of goals, is just, and I, my first venture capital fund, by the way, was called subtraction. Because we were all about focus, and we just wanted to do a small number of things, but do them really well. And so it was like I wake up every day still sometimes saying, what can I get rid of today?

[46:31] Jason Portnoy: What am I doing that’s not serving me? What is a bad use of my time? What is, you know, what’s not moving me forward? And subtract, subtract, simplify, simplify, simplify. And it’s amazing when you recover more and more of your. Time and brain cycles that might be involved in these distractions. You get a lot more powerful when you’re channeling your energy into those few things that are really that meaningful.

[46:57] Jason Portnoy: Your relationships, your professional work, your health, et cetera. You just become more powerful. You become more like a laser than a floodlight. That’s the analogy is your energy’s gonna be a lot more powerful if you, if you have a simple situ.

[47:16] Jim Harshaw, Jr.: Jason, thank you so much for sharing your pain, for sharing your failures, and for sharing your recovery and your story. The world is a better place for it. Thank you.

[47:28] Jason Portnoy: Thank you so much. Thanks for having me on the show. I really appreciate it. It’s been fun.

[47:32] Jim Harshaw, Jr.: Likewise. Thanks for listening. If you want to apply these principles into your life, let’s talk. You can see the limited spaces that are open on my calendar at JimHarshawJr.com/apply where you can sign up for a free one-time coaching call directly with me.

[47:50] Jim Harshaw, Jr.: And don’t forget to grab your action plan. Just go to JimHarshawJr.com/action. And lastly, iTunes tends to suggest podcasts with more ratings and reviews more often. You would totally make my day if you give me a reigning in review. Those go a long way in helping me grow the podcast. Just open up your podcast app.

[48:11] Jim Harshaw, Jr.: If you have an iPhone, do a search for success through failure, select it, and then scroll the whole way to the bottom where you can leave the podcast, a rating and a review. Now, I hope this isn’t just another podcast episode for you. I hope you take action on what you learned here today. Good luck and thanks for listening.

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