Ben Narasin: The Tenacity of Zenefits and Giving Lady Gaga a Boardseat

Sample Track by S-TZU: Delta DollarsFrom Teenage Hustler to Dot-Com PioneerBen Narasin’s journey is a testament to reinvention and resilience. From his early days as a 12-year-old hustler with entrepreneurial ambitions to becoming the founder of Tenacity Venture Capital, Narasin’s path is marked by conviction, adaptability, and a deep empathy for founders. By his teens, he was already innovating and finding ways to make money, but it was the launch of Fashionmall.com in 1993 that set him apart. Envisioning a future where fashion and the internet would intersect, Narasin led Fashionmall.com to become one of the first e-commerce companies to go public in 1999. When the dot-com bubble burst, he made the rare founder-first decision to take the company private, ensuring liquidity for all stakeholders and demonstrating his commitment to doing what’s right, even in turbulent times.Reflecting on his journey, Narasin notes, “Long journey, lots of overnight successes in the world that take decades.” After establishing himself on the East Coast, he moved to Silicon Valley, drawn by its unique entrepreneurial culture. Trading the title of CEO for that of venture capitalist, Narasin joined TriplePoint Ventures, Canvas Ventures, and later NEA, one of the world’s largest VC firms. Despite the shift, he remained an entrepreneur at heart, living vicariously through the founders he backed. This founder empathy became his superpower, enabling him to identify and nurture talent that would shape the future of technology.Me, Myself, and I: The Solo GP LifeAs a solo General Partner, Narasin injects humor and candor into his work. “I argue with myself all the time. People often ask, where’s your team? Well, I say, it’s right here. All three of us are here. Me, myself, and I.” This independence allows him to scrutinize his own decisions, constantly challenging his assumptions and refining his approach. “One of the nice things about being a solo GP is you only have yourself to answer to, for the most part. I mean, truth is the ultimate defense.”Narasin is known for his extreme selectivity, reviewing 10,000 pitches in two years but funding only six. In the previous year, he made just one investment out of thousands of pitches. His performance metrics are exceptional: a 13X MOIC, 97% IRR, and a 63–74% Seed-to-Series A progression rate. “I’m a bit overly neurotic and picky,” he admits. “Even with that, about a third of the companies don’t make it. So, you know, there is no such thing as a sure thing.” His portfolio includes standout companies like Dropcam, Zenefits, TellApart, Kabbage, and Vungle, underscoring his ability to back exceptional founders.CrossFit and Scaling Startups: Pukey the Clown vs. Uncle RhabdoTo describe the relentless demands of entrepreneurship, Narasin often uses CrossFit metaphors. “Startups demand everything,” he explains. “There’s no room for work-life balance. If you’re not collapsed on the floor at the end of the day, panting for breath, you probably haven’t put in enough effort.” He likens entrepreneurship to intense physical training, where resilience, discipline, and the ability to endure setbacks are crucial. Narasin also emphasizes the role of luck and timing: “You have to be smart, you have to work hard, but you will need some luck along the way. And the harder you work, the luckier you’ll be.” His IPO journey, where every day and decision mattered, reinforced the importance of relentless effort.Celebrity Capital: The Art of AuthenticityNarasin offers a nuanced perspective on celebrity involvement in venture capital. He recalls initial skepticism about Ashton Kutcher's entry into startup investing but came to respect Kutcher’s commitment and the strong team he built. Similarly, he questions the value of celebrity-led investment rounds, noting that true impact requires time, expertise, and dedication. “There are people that have made tremendous amounts of money investing in startups, and if being the celebrity that they are gets them access... there are a finite amount of things a successful investor has to do and do well, and they’re very time-consuming, they’re very hard.” For Narasin, authenticity and a willingness to roll up one’s sleeves matter far more than fame.* On Ashton Kutcher:“I remember when Ashton first came onto the scene, I ran into him at Y Combinator, had to be 15 plus years ago, and I remember being sort of quizzical. I’m not really a... first of all, I’m not into any sport, and I’m not really into celebrities, but I was like, huh, so I went over and said, what are you doing here? And he said, oh, I, you know, I’m interested in getting into some of the startup investing. And I remember thinking, Well...”* On Lady Gaga:“She said, Lady Gaga wants to invest. I was like, okay. She said, actually, she wants to lead the round. And I remember saying, why does that help you? Like, what is the chance Lady Gaga will have time to help you when you need help? ... But the idea of being a lead was something I was quizzical about, because that takes a very specific and rigorous set of realities that you want to do to create the right documents, because you’re setting terms for everybody in the round. And unless, unbeknownst to me, she had done quite a few of these, or had people that had as a partner, which is usually what happens, the celebrity partners with the person with the business experience.” Get full access to Seantzu at seantzu.substack.com/subscribe