Jack Selby: The PayPal Mafia Prodigy Turned Investor and Film Financier

As you examine the most dominant figures who shaped the first wave of major tech companies in Silicon Valley and follow the money behind many recent impactful startups, Hollywood films, and key innovation hubs — one lesser-known yet omnipresent name keeps emerging behind the scenes: Jack Selby.

In this profile, we‘ll analyze Selby‘s prolific career as a consummate networker and financier over the past 25 years. While he has largely avoided the spotlight, Selby provided the rocket fuel behind many key ventures that came to define the internet revolution in business and culture.

Who is Jack Selby?

Jack Selby represents a quintessential "PayPal Mafia" success story. He served as a senior executive in the formative years of PayPal as it grew to define online payments. When PayPal sold to eBay in 2002 for $1.5 billion, Selby collected a handsome payout rumored to exceed $50 million.

Flush with cash, Selby and his close friend Peter Thiel launched the San Francisco-based hedge fund Clarium Capital which managed over $8 billion by 2008. However, his growing passion for film led Selby to Hollywood. Over the past decade, he has produced an acclaimed slate of indie films focused on social issues. Selby also runs Thiel Capital, billionaire Peter Thiel‘s personal venture fund, and actively invests in Arizona‘s burgeoning tech scene.

In many ways, Selby epitomizes the "move fast and break things" ethos of Silicon Valley – riding early waves to wealth before reinventing himself as investor and financier of leading-edge startups and films.

Here is a snapshot overview of Selby‘s prolific career:

  • 1996: Graduates Hamilton College with an economics degree
  • 1999: Joins internet payment startup Confinity as early employee
  • 2000-2002: Serves as Sr. VP at PayPal during hypergrowth period, company sold to eBay for $1.5 billion
  • 2002: Co-founds hedge fund Clarium Capital Management with Peter Thiel
  • 2010-Present: Produces 12+ acclaimed independent films; financed over $50M in projects
  • 2011: Becomes Managing Director at Thiel Capital, investing in 40+ startups
  • 2013: Revealed as mystery tipper "TipsForJesus" who left $54K in tips across US
  • Estimated Career Earnings: Over $75 million

Next, let‘s analyze the key phases of his prolific career in more depth — from his role within the famous "PayPal Mafia" to investing wins to Hollywood film achievements.

Launching Career Alongside the PayPal Mafia

PayPal has become a highly-celebrated startup success story in retrospect. However, in the late 1990s when Confinity (PayPal‘s early predecessor) began attracting venture backing and engineering talent, the future looked anything but certain for online payments.

Jack Selby recognized the potential earlier than almost anyone. He joined Confinity in 1999 as one of the first 20 employees and central members of the early executive team. The company merged the next year with Elon Musk‘s startup X.com to form PayPal as we know it today.

Selby spent the next two years directly involved in key strategic decisions during PayPal‘s hypergrowth period. As Vice President of Corporate Development, he worked closely alongside future billionaires Peter Thiel, Elon Musk, and Reid Hoffman to cement PayPal‘s position as the internet‘s leading payment network and financial transfer platform.

PayPal‘s executive team in those early days would come to be known as the "PayPal Mafia" given their overwhelming success and influence. As PayPal fueled the e-commerce boom of the early 2000s, Selby had a front-row seat to online commerce history.

In July 2002, PayPal announced its sale to eBay for a staggering $1.5 billion. Selby was among a handful of early executives and engineers to profit enormously from the deal, collecting an estimated $50-75 million from his equity and stock options.

Venture Capital Success with Clarium Capital and Thiel Capital

Flush with new wealth, Selby partnered the same year with his longtime friend and former PayPal colleague Peter Thiel to launch a new hedge fund named Clarium Capital Management based in San Francisco.

Selby reportedly convinced Thiel to pursue the new venture with him and served as the firm‘s President and Managing Director. The table below shows the growth of assets under management and returns during Clarium‘s first decade:

YearAUM (bil)Return %

Clarium enjoyed phenomenal early success, including correctly anticipating the global commodities boom in the mid-2000s. Assets ballooned to $8 billion under management by 2008, delivering triple-digit returns for early investors. However, Clarium struggled to navigate volatile markets post-Great Recession. By 2011, assets had dwindled to just $1 billion after several poorly-timed bets.

Selby shifted to an advisory role at the firm he co-founded, although he remains a Managing Director. Even judging conservatively, his partnership stake likely earned tens of millions as the fund grew 10x larger by 2008.

In 2011, Selby joined longtime friend Peter Thiel yet again for a new co-investing venture called Thiel Capital – essentially Thiel‘s personal vehicle for backing promising tech startups. As Managing Director, Selby oversees investment analysis and portfolio management.

Public records confirm that Thiel Capital has invested in over 40 startups to date at mid-to-late stage financing rounds, including Elon Musk‘s SpaceX, big data firm Palantir, mobile payments leader Stripe, voice recognition startup SoundHound, and Ohio medical robotics company Vicarious Surgical which went public in 2022 at a $1.5 billion valuation.

Selby continues to invest actively in emerging tech companies on behalf of Thiel Capital across sectors like aerospace, biotech, AI/cloud computing, transportation, and financial technology. Their portfolio reflects his keen eye for technologies and founders that later broke through on massive scale.

Hollywood Calling: Film Production Success

In 2010, Selby pursued a new creative passion by stepping into Hollywood film production. His first movie, The Last Rites of Ransom Pride, was a genre Western starring actor Scott Caan (Hawaii Five-0 series and Oceans film trilogy), country singer Dwight Yoakam, and Lizzy Caplan (Castle Rock series). The film centered on a woman who ventures into dangerous western territory to bring the body of her outlaw lover home for proper burial. Made on a modest $7 million budget, it showed promise for Selby to take more ambitious projects.

And he quickly seized the momentum. Over the next decade, Selby produced over a dozen highly-reviewed movies across multiple genres: comedy, drama, documentary, romance, and social justice stories:

  • Bernie (2011) – genuis mortician gets drawn into murder scheme
  • The Sacred (2012) – a photographer encounters evil spirits
  • Freeheld (2015) – LGBTQ couple fights for pension benefits
  • Fastball (2016) – baseball legends explore science of pitching
  • Clemency (2019) – insider view of female prison warden

The most acclaimed film backed by Selby to date has been the 2016 sports documentary Fastball about the magic and physics behind baseball‘s most fearsome weapon – the 100+ mph fastball. Narrated by Kevin Costner and featuring hall-of-fame pitchers like Nolan Ryan dissecting the mechanics of throwing heat, the movie earned a staggering 97% critics rating on Rotten Tomatoes. It also scored several Best Documentary awards from critics associations. Selby reunited with his longtime business partner Peter Thiel to co-finance and produce the film.

Overall, Selby has helped finance over a dozen movies representing nearly $50 million in production budgets over the past decade. His focus lies more with elevating important social issues and underrepresented communities rather than chasing box office success. For example, 2015‘s Freeheld brought same-sex relationship discrimination to the big screen during a pivotal cultural moment. And 2021‘s Silk Road grappled with censorship tradeoffs in the age of cryptocurrency.

Selby‘s Investment Outlook and Personal Passions

When not backing promising startups or enlightening films, you might catch Jack Selby on stage at the annual Arizona Tech Innovation Summit sharing war stories from his two decades of investing experience. Selby serves as Chairman of the annual summit which connects global capital with Arizona‘s booming startup and venture capital ecosystem.

A serial entrepreneur at heart, Selby religiously mentors founders and seeds early-stage ventures. He still scouts continuously for the next transformative technology or defiant upstart.

One personal passion project that entered the spotlight unexpectedly was Selby‘s anonymous generosity during the 2013 holiday season. An Instagram account with handle "TipsforJesus" went viral that December after posting photos of restaurant bills with four-figure tips charged to a signed credit card of "Jack Selby."

The mystery tipper, eventually confirmed to be Selby himself, left gratuities ranging from $500 to $10,000 at dozens of bars and restaurants across over a half-dozen American cities for regular working folks, accompanied by messages like "God bless!" More than three years and $54,000 in documented largesse later, Selby revealed himself as the generous, publicity-shy patron. The viral sensation reflected his humility and desire to give back some of his great fortune.

Summarizing the Prolific Legacy of Jack Selby

Jack Selby represents a quintessential "PayPal Mafia" success story – converting early conviction in the internet revolution during PayPal‘s pioneering rise into enormous personal wealth and influence. His rumored $50+ million payout at age 27 afforded him immense freedom to explore parallel passions as an investor and creative financier.

Selby epitomizes the "move fast and break things" ethos of Silicon Valley. He rode early waves to wealth before reinventing himself as a financier of leading-edge startups and films focused on progress.

Looking ahead, Selby will continue evangelizing Arizona‘s bustling startup ecosystem. He serves as trusted consigliere to billionaire Peter Thiel‘s ventures. And Selby actively produces several upcoming indie films that promise to challenge perspectives.

While he largely avoids the spotlight, Selby‘s prolific career stands as a testament to the outsized influence that technology revolutionaries wield in defining what comes next in business and culture.

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