From modest roots in the suburbs of New Jersey, Jason Portnoy followed a script carefully crafted by society and found himself in the middle of the PayPal mafia, launched into a Silicon Valley career of wealth and prestige that he never dreamed of. Stock options, flashy cars, an amazing family, on the outside, his life looked perfect but unhealed traumas from his past left him tortured, descending into a dark world of pornography and sex that eventually pushed him to the edge.

In Silicon Valley Porn Star, Jason willingly shares his personal transformation from a life of extramarital affairs and superficial excess to one of chosen values and renewed relationships. His journey sheds light on a crisis of masculinity in our modern world where quests for unlimited power and success are gateways to addiction, dependency and unhinged behavior. No matter your profession or your position in life, Jason’s story will inspire you to look within, to find your own path towards fulfillment and become the person you want to be. 

Here’s my conversation with Jason Portnoy.

Welcome to The Author Hour Podcast, I’m your host Benji Block and today, we are joined by Jason Portnoy. He just authored a new book titled Silicon Valley Porn Star: A Memoir of Redemption and Rediscovering the Self. Quite the title, got a lot to chat about today but Jason, welcome to Author Hour.

Jason Portnoy: Thanks for having me.

Benji Block: Jason, we can start with just a bit of your résumé before we get to the book itself and so, I’ll say, from a high level, it includes a couple of engineering degrees, Stanford, University of Colorado, you had time at PayPal, you’re an entrepreneur, a venture capitalist, you’ve worked up close with some top names in business so we could stick to business books but you went memoir instead and specifically a memoir of redemption and rediscovering self. Tell me a bit about what prompts a book like this. Like, why now, Jason?

Jason Portnoy: Well, I felt like I had this kind of crazy journey that today, when I look back on it, it feels like a whole entirely different life. I got to a point where I started sharing it with people, especially young men that I was working closely with as kind of a cautionary tale of what not to do or folks and at some point, I just thought, I need to write this down. I think I need to write this down, I think it can help people to learn from some of the stuff that I went through and part of my journey as I got to the other side of my journey was this really deep feeling that I have everything I need and all I want to do now is be in service.

So, what can I do to be in service to the world? And it felt like sharing a story and I hope that it helps people that would make me feel like I’m being in service.

Benji Block: Yeah, I mean this in the best way possible but when I prep for interviews, I usually take a bit of time, I’m trying to understand where the author’s coming from and because of the number of interviews I do, it’s kind of, “All right, next book, next hour, I got to do something different” but you ruin the last few days of my life because this is one that you sink your teeth into.

With that being said, as an interviewer, when I am doing something with a memoir, there’s a number of ways we can go because you have all of your life really that you’re looking back at. To me, your childhood is very interesting and provide some context. We know, again, because of that high level, like, where your life ended up, saw some massive success but rewind with me and let’s go back to your childhood. Tell me a little bit about Jason as a kid?

Jason Portnoy: Yeah, I feel, the way I’ve described it to people that the story is, I was just a humble kid from the suburbs of New Jersey and that’s where I grew up. When I was very young, we were in a very rural area where it was further out kind of in the woods, closer to upstate New York but then, when I was in sixth grade, we moved to kind of the quintessential suburb in the middle of the state. 

You know, sidewalks, half the houses had pools, it was very close to a lot of agricultural land so there was that element as well but anyways, kind of a quintessential suburb and I grew up doing kind of – I feel like the standard things that the kid in that scenario might do. I played soccer, I was a Boy Scout, I was on the swim team, you know, lots of different activities and I feel like it was just pretty down the fairway in that regard.

Benji Block: I want to talk about your family dynamic as well because it’s one that I think there’s several pieces and components to it. So from one aspect, outside looking in it’s like, “Oh, this is a typical family kind of growing up” But then, if you look under the surface, there’s a number of things happening and dysfunction.

I want to actually run through and this is going to require some imagination but I want to run an exercise real quick. I want you to imagine you’re 13 years old and I want you to tell me if you’re imagining your home at that age, introduce me to the main characters and then in your imagination, when I’m walking you through this exercise, tell me what rooms those characters are in, in your head.

Jason Portnoy: Wow, this is great. I’m in my house, my mom battled with depression for a lot of my youth and she’s probably in her room in bed and as a result of that, you know, there’s this sense that the house needs to stay quiet. So the house is kind of often very quiet, somewhat dark, my stepfather is probably in the basement working. He had a home office who did a lot of consulting work and my sister’s probably gone.

When I was 13, she was 19, so she was off at school or with her friends or something else. I wound up spending a lot of time alone as a kid and I think the point you were making earlier that from the outside, it did look like this kind of normal thing. I think this happens to a lot of us, frankly.

It seems like everything’s fine on the outside, but then, when you start to scratch below the surface, there’s this boy, he’s kind of confused, his mom’s not really well but she looks fine. You know, it’s not like she has a broken leg so can’t really understand what’s wrong with her, alone a fair amount, watching TV, maybe going to play outside with friends and not really understanding that something’s not quite right here and it took me years, decades really, to understand what that did to me.

The Root of Influences

Benji Block: The complexity of the story as well is, and you just said it really well, there’s essentially two lives happening because there’s one of outer success and there’s one where you’re – whether you know it or not, there’s parts of ego at play, there’s hurt kid at play, there’s what we can keep a secret at play and those, as I’m looking at your story, I’m going, “Man, what do we talk about first?” Because we could talk outer success.

Jason Portnoy: Yeah, and there’s another thing I play which is, I was kind of – I feel like I was kind of fertile ground, I was very impressionable and so, kind of fertile ground for all of these stereotypes and societal norms and pressures and influences to take root. Again, I didn’t quite understand all of that at the time.

It was only when I started to grow into adulthood and I think if I may, I’ll offer some direction here for that, which is, what really started to happen for me is I got launched out into the world as this kid from New Jersey who just wanted to go and be successful. I didn’t even know what that meant and I kind of did all the things I thought I was supposed to do.

So I went to college, I got a degree in chemical engineering, I got good grades, then I went to Stanford, I hustled my ass off and got good grades there and then I got a job and I made a bunch of money when I was young and I kind of gotten to this mode where I felt like I was doing all the right things but then sometime later, I realized I still wasn’t happy and that was really where part of the story kind of starts. 

It’s like, I went out, I thought, “If I get lots of money and I have a really cool car and a beautiful wife and a family and a house and all of these things, I’m going to be happy. I’m going to be a real man and I’m going to be happy.” and I went out and I got those things and I was miserable and that was really disorienting and scary, frankly.

Benji Block: It is a fascinating spot to be in when you reach what you thought was success and it doesn’t feel like success. I found, there was a line in the book that I particularly from – there was like a big fight in the house the night before, you’re a kid and you say that, “I desperately wanted to get lost with them, being the kids on the playground, in the games that they were playing but I can’t, I hold back.”

And then you say, “I won’t be able to manage the flood of emotions, I have to keep some distance and I have to stay in control.” That phrasing to me, I have to keep some distance, I have to stay in control. If I fast forward in your story and I’m going, what are like some of the high-level lessons. To me, when you’re trying to figure out what is a man, how will I be this successful man, control becomes a pretty key word, doesn’t it?

Jason Portnoy: Absolutely, I do feel, and I feel like the controlling element can manifest in a lot of different ways for different men, depending on their background and the culture that they’re raised in. I think in some places, control and power is seen through money. In some places, control and power is seen through like physical size, the strongest guy wins sort of thing. So I think it manifests in different ways without the core, there is this power element and this control element of being able to control what’s going on around you.

Benji Block: Okay, so I want to fast forward because we don’t have all the time in the world but your junior year, you get busted selling weed and so as I’m reading that part, I’m going, “How the heck is this guy going to end up with two engineering degrees?” like, get me there. 

Jason Portnoy: I was an entrepreneur. I was an entrepreneur way back then.

Benji Block: Yes, that’s exactly right but tell me what correlates into then, you go into Stanford and University of Colorado, what’s the interest that sparked there to that further education?

Jason Portnoy: I was doing these really silly things in high school but I was very lucky I got caught and I feel like – and you know because you read the whole story, getting caught happens a few times and when I look back on my life, it is those moments when I got caught that are the most priceless moments. It was like, “Thank God I got caught” because if I didn’t, I would have just kept going down, I think, the wrong path.

So I got caught selling pot at school and I got suspended and they tried to expel me but I wound up just getting suspended for a long period of time and during that time, I got tutored and I had to get separated from all of the people and places that I had been hanging out with and going and I really turned my life around in a small way.

I mean, I was still pretty young and said, “Hey, I want to go to a good school, I want to get a good education, I want to get a good job when I’m older” and my parents were all chemists and my dad said, “Hey, you should try chemical engineering” and I love to ski and so I looked up what schools had great skiing and great chemical engineering and University of Colorado was one of them and so that’s how I wound up in Colorado.

Benji Block: I want to go back to what you said a minute ago about getting caught being essentially priceless and that being a key pattern in your story and we’ll get to some of the other times you got caught. But does it end up in a place of fear at all, Jason, that you’re going, “I see this pattern where I had to get caught to change” or what is that bring up in you now, looking back?

Jason Portnoy: Well, I think that I try not to talk to esoterically but I do feel like there are forces at play that are bigger than we are and that in some way, they’re sending us these signals to kind of wakeup a little bit. “Hey, you’re kind of going down the wrong path, maybe you want to go that way.” They send you little notices and signals and you have to pay attention to them and getting caught is just one of those that’s harder to ignore.

Relationships: With Others and With Yourself

Benji Block: Harder to ignore, can be extremely painful but again, ends up being pretty helpful and priceless for you. Yeah, it’s in your college years, right? That you meet Anne Marie, your wife?

Jason Portnoy: Yes, freshman year.

Benji Block: Tell us a little bit about meeting her?

Jason Portnoy: Man, it is just I think, the classic opposites attract. She is this graceful, soft-spoken, amazing woman who grew up in Guam so she looks different than anyone I’ve been around, she’s just different. Her energy is just so different from anyone I grown up around or been around and conversely, she meets me and I’m probably wearing like white jeans and my ears pierced, I’ve got like a gold chain, I’m listening to Metallica or something, I don’t know, but it was that I’m from New Jersey and I’m super rough around the edges and we just met each other and it was instant. We were just connected.

Benji Block: So now, you have a woman by your side, you’re walking through these — what turns into some great years. Again, we’re going, we got two lives happening but let’s talk about the success because after college and some key connections happening, you see massive, massive career acceleration, you’ve gained financial success, fancy car, which was a big deal in your mind, right? You had to have the car and then her thing was traveling around the world which eventually you even have the opportunity to do that.

Your parents are looking at you, they’re proud and so you’re doing essentially what you would say, again, people are going, “Man, Jason’s doing this right, he’s doing the right things.” What’s wrong with that story?

Jason Portnoy: Yeah, what’s wrong with that story is that there’s a whole alter ego, shadow life that I start living. At some point, it probably starts back in college and it kind of ballooned and as my wealth increases and my career success increases and I’m just gaining, you might call it confidence but it might be more like, my ego is just swelling and I start to kind of go off the rails. I’m like, “I can do whatever I want, I’m successful, I deserve it.” 

The way this started for me was, this alter ego kind of started back in college with online porn and I stumbled into it and it became a habit and it was a habit for a very long time and then again, as my ego started to swell, it started turning into going on to Craigslist, which at the time had a casual encounters section where people would go for hookups and so I started doing that sort of thing.

It kind of snowballed from there and I’m happy to go into it, I don’t know how much you want to leave for the book. It snowballed from there and it was all a secret. Ann Marie didn’t know. You know, her and I were together for years and years, she didn’t know that these things were happening and so I was lying, then you’re starting with the guilt and then starts the shame and you wind up in kind of a shame cycle and all of that started. 

Benji Block: There is so much to this story. One thing you talk about is that you never really outgrew some of the childhood habits and coping mechanisms. What are some of those things that maybe did you think you would outgrow them but then you just see them kind of continuing the pattern and the cycle? 

Jason Portnoy: Well, I don’t think much of it was anything I was thinking about. So I think a lot of these things affected me and I think affect a lot of us on a quite subconscious level. There’s these, you know, we get programmed in our youth and then we start living our lives based off of the programming and then we go out into the wild and then we encounter a situation that’s new to us, we compare it to our programming to figure out what we should do. 

It is a very adaptive trait for our brains and then at some point, well in my case, I reached the point where the programming wasn’t serving me anymore and that’s when everything started to breakdown but I think what I had carried forward from my youth was this ability to compartmentalize. So I had segmented myself off, there is the Jason everyone sees and then there’s the Jason that comes out at night and they were two different people. 

Benji Block: You have this balloon to use that metaphor, that’s essentially in the dark. You mentioned your ego swells, you mentioned thrill seeking, which again, in both of those it’s in my head. It’s a balloon getting bigger and bigger, so if your ego is swelling, you are thrill seeking, eventually, the bigger thing you’ve done isn’t enough and that’s what creates seemingly and always escalating behavior. 

Jason Portnoy: Appetite, right? It’s like this insatiable appetite, that’s right and it’s just never enough and I think I absolutely fell into that and it wasn’t until many, many years later and I was in coaching with my life coach, who I talk a lot about in my book. She was an incredible start, you know, a part of my story. I still remember this to this day, there was one conversation and she had been coaching me for years at that point. 

I was talking about something and making money something and she said, “How much money do you need?” and she had no idea how much I had. She said, “How much do you need?” and I realized I had never really asked that question. The only answer would have been more and it would have never mattered where I was. For accomplishments, money, whatever you’re measuring yourself by, it would have never mattered. 

I would have just said more and that’s because what I learned later was that there is a void inside of myself, kind of a hole in myself that I was trying to fill with all of these external things and what I had to learn was that all of the successes and credentials and titles and money and cars, women, all of that stuff none of it would fill that hole. The only way for me to fill that hole was to start tuning all of that stuff out and start to look inside myself and understand myself and understand where these things were coming from and that’s when I started to heal that. 

Benji Block: When someone is doing the work that you are talking about, that internal work, at first it seems so daunting because you have been looking externally for so long that to then turn inward, the way I would describe it is a silence where you’re like, “I don’t even know what I think.” Did you experience that or how would you explain as you turned inward what those first emotions, what those first feelings were? 

Jason Portnoy: I did experience that and the first emotions were fear. It was very scary because my whole life I thought this is what it was about, money, cars and women, more money, more cars, more women, whatever. I thought that what it was all about and when I realized that it wasn’t about that, it was very scary and I started looking inside myself and you know, it was a very long process. 

I think one of the things I have learned and then I shared with some people is to move at your own pace and I think people kind of underestimate how long it takes because if they think it is going to take a long time then they’re afraid to start, you know? 

Benji Block: 100 percent. It is earth-shattering, it’s foundation-breaking. 

Jason Portnoy: That’s right and so we’re tending to look for this quicker fix like I am willing to go to therapy for six months and I’ll be fine. And so for me, there was a few years of coaching before I started to really turn inward and then all of those things were I’m just going I had to clean up a lot of other stuff on the surface before I could start turning inward and what that looked like during those years was simplification of my life. 

In fact, when I started my venture capital firm in 2012, I named it Subtraction Capital and everyone laughed. I laugh about it now, everyone laughs, you can’t subtract the money, you can’t start a financial services company called subtraction but anyway, the reason subtraction was so important to me at the time was that it was the journey that I was on to simplify my life. Unsubscribing to all the email stuff, turning off social media entirely so that I could find that quiet place. 

You correctly identify that there is a silence, there is a stillness when you start to do that. It has to mirror what’s happening in your outside world. It is very hard to have stillness and quiet inside if you are outside world is very chaotic and vice-versa. 

Understanding The True Intimacy Comes From Honesty and Holding Space For One Another

Benji Block: One thing I want to throw in there too is it’s really hard for the voices to be quiet if there’s a lack of honesty internally. If I was boiling down what I experienced reading this book, this is a story of coming truly clean and honest because there is really no way to go inward if you aren’t willing to be honest with yourself and with the people close to you. I don’t want to give away your entire story, Jason, because we want people to go read it but tell me what your journey has been like with honesty. 

Jason Portnoy: That is the hard part and for me, you know, I’ve got to this point where I had to be honest. I just couldn’t maintain the dual thing anymore and I had to look inside and I had to look at those parts of me that I didn’t like and I had to be really honest with myself about what I was seeing and this life coach I mentioned, I talk about it in the book was so instrumental in that. You know, there were times where I’d said, “You’re just a mirror.” 

She was just a mirror or holding up a mirror and showing me and encouraging me to love myself and saying I know in a way you don’t like what you see right now but you need to love what you see if you are going to move in that direction of healing that. That was a really big part of it. 

Benji Block: How long are you working with her? This is again, the process takes time. So even before you can be totally honest with her and then just give us the timeline of that even with Anne Marie because that’s a key component that you mentioned. It’s the timing of all of this. 

Jason Portnoy: Yeah, so Anne Marie and I have a daughter in 2009 and about six months or a year after that, we’re really struggling in our marriage. That’s the first time I started going out to seek help, talked to a couple of different therapist but eventually meet this life coach and it takes a few years of coaching work before we are starting to be a lot more honest with each other and a lot more honest with ourselves. 

Then it wasn’t until the beginning of 2015, so about six years later that I am finally ready to really come clean, that I really understand that if I am going to move forward in a life that I want to live where I am not just running off of my programming from when I was young but I’m cleaning all these stuff up and moving forward in a healthier way with integrity, the only way to do that is to tell my secrets. 

That’s the only way forward. If I keep my secrets, I will stay sick and if I stay sick, I will stay on this path into a dark place. It was just that clear. 

Benji Block: Secrets lead to sickness but that’s the story of life, right? It’s like who can we let fully see us, fully know us and fully love us and that journey, which is why I wanted to start with your childhood at the beginning of this. There is so many things that happen along the way that go reinforce these ways of thinking that lead to sickness. Well, no matter if it was meant to or not and I think that is the unfolding of life’s narrative right there. 

Jason Portnoy: Yeah, I have lots of different hopes around the book but one of the things I really hope is that it encourages men or couples to be more honest with each other, to hold a space with each other. You can imagine a conversation where a husband or a wife decides that they are ready to reveal something, to be more honest with their partner and the partner’s reaction is like rage and they’re hurt and they’re angry and “It’s over and we’re getting divorced” and blah-blah-blah. 

If there’s a way, you know I hope that by reading this, it can show that there is a way for couples to move through some of these really difficult things and hold space for each other, not take it personally and realize that each of them is on some journey. That their soul is on some kind of journey and they can hold the space for their partner and that is a really powerful thing and what Anne Marie and I found in our relationship is that was true intimacy. 

Intimacy was not what happened at night. The true intimacy was being really honest with each other and holding space for each other and that’s what really has made our relationship what it is today. 

So, Why The Porn Star Title?

Benji Block: We’ve gone 30 plus minutes without addressing why you named the book what you named it. So let me, with that all as backstory, Silicon Valley Porn Star, give me the reason for that title and why that made the most sense for you. 

Jason Portnoy: You know, when I first admitted to my life coach that I was struggling with porn and then I felt like I wanted to stop looking at porn but I couldn’t and she had this method of working with me where we would kind of assign a behavior to an identity inside my universe so that I wouldn’t have to think about it so personally and feel so much guilt and shame. I could be a little bit more objective. 

She one day, just kind of as a joke, she nicknamed this identity of mine Porn Star and we laughed and then we would get on the phone for a coaching session and she’s going to be like, “So how’s Porn Star this week?” she just wanted to get caught up on the gossip and frankly like her levity around it and then I would start sharing really embarrassing things that I don’t think I would have shared otherwise and so that’s where the name Porn Star came from. 

Then my career grew up in Silicon Valley, it is a really big part of my life and my story and I just felt like the pairing of the two would definitely get people’s attention. 

Benji Block: It does, it rightfully does and I – whoa, there is a lot there. Let me ask you as we start to wrap, you’re talking to an audience where there’s those that are addicted. So I want to chat around porn addiction for a second before we just leave this conversation entirely. You see it as not just something you were looking at but you describe it as an addiction, as a drug and there is many that would resonate with that. 

Jason Portnoy: As a gateway drug.

Benji Block: It is a gateway drug and it was a gateway drug for you, yet walk me through how you view porn now with how massive of an impact it’s had and an imprint it’s left on your life. 

Jason Portnoy: I look back on my journey, I am not necessarily proud of it but I kind of appreciate it for what it taught me and what I learned and having been engaged in that stuff and in that place, I feel like I can interact with others who might be in a dark place with no judgment because I have kind of been there. I do feel very thankful for that but these days, I think porn is just bad news. 

I know that in some corners of society, it’s become a little bit more accepted or maybe just tolerated. It’s like it’s here and it’s going to stay and everyone watches it and all that stuff but I think it’s really toxic. It is really dangerous, it is really damaging. You know, I don’t think there is any way a man can sit and consume online pornography and then walk into an environment with women, whether it’s at work or anywhere and it not affect the way that they interact with women. 

At this point, I feel like the acceptable amount of is zero. I think it’s hurting men, I think it’s hurting women. 

Benji Block: It’s a conversation we got to be having more often and it’s one of the harder conversations to have, so thank you for braving that wilderness and trying to cross that chasm and bring others with you to have the conversation. Jason, when someone has completed this book, what are you hoping they feel? What are you hoping they’re invited into? I would love to hear your thoughts on the readers that are going to experience this whole story. 

Jason Portnoy: Yeah, well, if they are in a dark place, I hope they feel like there’s some hope that they can change. They should change at their own pace, they shouldn’t try to rush it. It is a lifelong journey of change. I hope they feel like there’s hope. I hope for some young men, maybe it is a cautionary tale of what not to do like maybe take a harder look at what society is telling you, you need to have to be happy and don’t just take society’s word for it but really think about it for yourself. 

Like I said earlier, I do hope that for couples it provides an example of a couple that went through some really difficult things but held the space for each other and made it through. 

Benji Block: Well, I can say having read it, this is a book you won’t want to put down and is one that I do believe accomplishes what Jason just said around hope and I see the path for couples to have much more genuine honest conversations after reading a story like this one. So Jason, thank you for doing the work and continuing to press on towards being the most honest version of yourself and I commend you for that journey. 

For those that want to continue to stay connected, obviously we’d say go get the book, you can do that on Amazon but where can people reach out? Maybe it’s a website or what’s best for that.

Jason Portnoy: So my website is jasonportnoy.com and there’s a contact page and some other additional information and I’d be happy to hear from people and hear their stories. 

Benji Block: Again, the title of the book, Silicon Valley Porn Star: A Memoire of Redemption and Rediscovering the Self. Jason Portnoy, I can’t say thanks enough for stopping by Author Hour today man. 

Jason Portnoy: Thanks, Benji, this is fun.