This memoir of redemption reveals the deep-seated issues of stereotypes and addiction in the tech world, urging a reevaluation of values in the pursuit of success.

BY AVA BLIXT

In 2016, Taiwan announced its ambitions to become Asia’s Silicon Valley. If successful, the government’s plan of connecting Taiwan with global high-tech R&D communities and “seizing opportunities in next-generation industries” could cement its position as a global tech leader.  

For the people living and working somewhere like the Bay Area, it can seem impossible not to be swept up in status-chasing and other shark-like behavior. And for those who hope to be among the winners in Taiwan’s Silicon Valley project, Jason Portnoy’s memoir Silicon Valley Porn Star (now available in traditional Chinese) is a recommended read.  

On paper, Portnoy is a great success. He 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 CFO of Palantir Technologies and later founded Oakhouse Partners, a top-performing venture capital firm.  

But he is also a recovering sex addict whose marriage and career were nearly destroyed by his addiction. This is the main story told in Silicon Valley Porn Star. 

In this thought-provoking memoir, Portnoy describes the feeling of being caught in what Richard Yates once coined “the hopeless emptiness.” Portnoy sacrifices his marriage for a job that lacks meaning and constantly makes him feel like a failure. He’s got the money, the car, the women, and the title – yet he feels empty inside, and his self-destructive behavior only exacerbates with time.  

One of the book’s central topics is shame and its damaging effects on our lives, a matter Portnoy tackles with an intensely personal style. Rather than relying on abstract theories, he provides practical and relatable experiences that help readers connect with the story. Another standout feature of the book is the author’s candor in tackling his issues head-on. He doesn’t sugarcoat or minimize the rigorous effort required to overcome addiction and trauma. It’s a clear reminder that change is possible, but only if we are prepared to confront painful truths and rebuild our lives. 

With clarity resulting from years of therapy and coaching, Portnoy includes the moments that move the book forward without lingering on the minute details. His language is clear-cut, and apart from the occasional change of tense, it doesn’t distract from the impactful story he shares. He’s humble, real, and raw in his recollections.  

The themes of Silicon Valley Porn Star span the guilt of outperforming your parents, the detrimental effects of not acknowledging uncomfortable feelings, the dangers of self-medication and addiction, and the universal struggle of finding one’s place in the world. But two themes are particularly pertinent – how the concept of “manhood” hurts men, and how it hurts women even more.  

Throughout the book, Portnoy asks himself what it means to be a man, a concept so elusive he thinks he’ll never understand it. Lacking a sense of identity, he repeatedly mirrors himself against others. The first to be subjected is a cop. Portnoy writes: “He is good; I am bad. He commands respect; I pretend like I deserve it. He is a man; I am a boy.” Most often, however, Portnoy juxtaposes himself against his wife. On their wedding day, he recalls thinking of her as a “queen,” adding that he doesn’t feel like a king himself. 

Equally important is whom he chooses not to compare himself with. These are the men he views with unequivocal admiration. One example is Silicon Valley billionaire Peter Thiel, Portnoy’s boss first at PayPal and later at Clarium. Portnoy describes Thiel as kind, warm, and having a “Midas touch.”  

Thiel has become a contentious figure through the years. In 2016, he stirred controversy by bankrolling a lawsuit against the blog Gawker Media – known for its critical and ruthless examination of those in power – ultimately leading it to bankruptcy. Critics have argued that Thiel’s money gave other billionaires a blueprint for silencing media outlets they dislike. Despite being the first outsider investor in Facebook, Thiel has also made business choices seemingly conflicting with his interest in the social media platform. In 2019, he backed the startup Clearview AI, which scrapes internet profiles to create a facial recognition tool for law enforcement. Facebook stated its policy prohibits such scraping and asked the company to stop using its data.  

In the 1990s, Thiel co-authored a book stating that when alcohol is involved in a rape case, “it is unclear who should be held responsible.” (Thiel later apologized.)   

The dearth of critical examination of men like Thiel is given greater meaning when Portnoy reveals his initial incomprehension of sexual harassment and assault, particularly in the workplace. This ignorance manifests when Portnoy finds himself in trouble with one of his portfolio companies after trying to sleep with a young female employee. The woman considers pressing charges, lawyers are involved, and Portnoy envisions the headline: “Venture Capitalist Hits on Portfolio Company Employee.”  

To Portnoy, it seems at first to be not much more than an embarrassing indiscretion that could potentially harm his reputation. Reality – particularly post-#MeToo – is much more dire. He is lucky not to be sued or prosecuted.  

Recognizing the unequal power dynamics at play when an older, married man propositions a young woman over whom he has direct financial power, Portnoy later becomes aware that he is sending the message that men are not to be trusted, that “men are predators and only after one thing. Men are weak. Or worse, I am implying that [the women’s] only worth is their sexuality.” 

In Taipei’s business world, such occurrences are all too common – most women here will have a story to tell. Last year, a friend of mine accepted an invitation to dinner by a couple of business acquaintances, during which she was drugged and sexually assaulted. Other female friends have been sexually harassed by members of their organizations, only to be told by management that nothing could be done about it, and that perhaps they should “keep their distance from these people” at future events.  

Can’t blame a guy for trying, right? 

We may have a female president, but it’s still common for men in Taiwan – citizens and foreign nationals alike – to pay for “dinner girls” to accompany them at business events. At karaoke parlors, women are neatly lined up like products on a shelf, as the men pick out those they prefer for the night. Mistresses are called “second wives,” and few people raise eyebrows when they hear about a wealthy businessman’s decision to “baoyang,” or reserve an escort who will adjust her schedule to suit his and provide sexual services only to him.  

For many men, it’s hard to resist or avoid these situations. “Everyone else” is doing it, and it’s often in those dark rooms that the real deals are brokered. Consequently, women hardly stand a chance. Their role in these rooms is to be a commodity, not an equal partner. 

Sexism and chauvinism are more widespread in Taipei than Covid ever was, and few have the power or interest to fight it. Last year the Legislative Yuan passed amendments to three bills relating to sexual harassment. But that is not enough when the problem is deeply embedded in society. As Taiwan aims to become “Asia’s Silicon Valley,” we could do more not to embrace the worst parts of the culture. 

For Portnoy, escaping the toxic culture of “manhood” involves confronting his addiction, reconciling with his family, making healthy choices, and asking himself what success is to him and not others. It’s a long, arduous journey, but it’s one that saves his life. 

Silicon Valley Porn Star provides a compelling case study on challenging both a toxic culture and one’s own damaging tendencies. I know many men – and women – who would benefit from reading this book. I’m sure you do as well.