So you want to make it big as an entrepreneur in Silicon Valley? Allow me to introduce Ken Howery – the quintessential strategic pioneer who leveraged opportune timing, financial acumen and an elite network to achieve massive returns across multiple blockbuster startups over the past two decades.
In just four years, Howery rapidly transformed online payments pioneer PayPal from a fledgling startup into a billion dollar public company. He then parlayed early bets on emerging giants like Facebook into his next smash hit – the growth stage investment fund Founders Fund surfing the Web 2.0 wave to over $3 billion assets under management.
Even while investing in hundreds of startups, he still found time to serve his country abroad as Ambassador to Sweden. Ever wondered how certain brilliant businessmen have a knack for being at the right place at the right time to ride almost every technological wave accelerating global disruption? Ken Howery represents that rare breed of visionary who shapes revolutions as much as he profits from them.
The Early Years: Houston to Stanford
Long before making fortunes in Silicon Valley, Ken Howery spent his early years in Houston, Texas. Described as studious and ambitious from a young age, he immersed himself in various high school activities like student council and model United Nations. He graduated as Valedictorian before heading west to Stanford University in 1994.
Transitioning to the intellectually-charged environment at Stanford, Howery continued his active involvement in student organizations like the Stanford Review while contemplating potential career paths. Surrounded by children of Silicon Valley luminaries and early internet pioneers, he found inspiration in alumni legends like Jerry Yang who had created pioneering search engine Yahoo! just a few years prior.
Stanford’s entrepreneurial culture and location at the heart of global technology innovation undoubtedly motivated Howery to recognize emerging online payment networks as the next potential goldmine. Combined with his financial management skills and strategic prowess, the stage was set for him to play a starring role as an internet pioneer in the late 1990s dot-com boom.
Launching PayPal and Taking it Public: The First Big Score
When Peter Thiel approached fellow Stanford alum Ken Howery in 1998 to get involved with his online payments startup idea, Howery didn’t hesitate to join despite having limited prior experience. He saw enormous potential to disrupt a hugely inefficient global payments market relying on antiquated tools like checks and money orders.
Teaming up with the talented likes of Elon Musk and Max Levchin in addition to Thiel, Howery served as the company‘s first Chief Financial Officer while it underwent several name changes before being christened PayPal.
As CFO, he navigated key funding rounds, established budgets and operating plans, handled legal and HR matters, and communicated value propositions to prospective investors. Howery managed finances prudently even as headcount and infrastructure scaled exponentially to support surging adoption.
PayPal’s triumphant public listing just four years later attracted enormous publicity in addition to marking a major payday for early employees and investors. By taking the company public in rocky market conditions, Howery played a pivotal role in cementing PayPal’s image as an attractive acquisition target. His financial stewardship and leadership helped maximize that valuation when eBay ultimately snapped up PayPal later in 2002 for $1.5 billion.
The Thiel Mafia: Cultivating the Network
Ken Howery’s professional association with Peter Thiel predated even their PayPal journey, having worked together earlier at Stanford Review. That relationship profoundly impacted his career trajectory in the decade after PayPal’s sale, as Howery repeatedly turned to Thiel as friend, mentor and business partner across various new ventures.
Following brief post-acquisition stints at eBay and hedge fund Clarium Capital, their most successful collaboration involved co-founding venture capital firm Founders Fund with other members of the so-called PayPal Mafia.
“Ever wondered how certain brilliant businessmen have a knack for being at the right place at the right time to ride almost every technological wave accelerating global disruption? Ken Howery represents that rare breed of visionary who shapes revolutions as much as he profits from them.”
While Thiel provided the initial concept and seed capital, Howery took charge of daily operations as Managing Partner rapidly scaling the fund to over $3 billion under management by 2014. Unlike most VC firms focused narrowly on tech, Founders Fund embraced ambitious scientific ventures like biotech and aerospace explore outsized growth frontiers.
Their early bets on emerging giants like Facebook, SpaceX and Spotify generated phenomenal returns – especially once founders like Mark Zuckerberg came to Howery for later stage funding. As Facebook’s first institutional investor, Founders Fund multiplied their initial millions into a billion dollar windfall over time.
| Year | Fund Size | # Investments |
|---|---|---|
| 2016 | $1.3 billion | >80 |
| 2010 | $750 million | >50 |
| 2008 | $250 million | >20 |
Howery’s close ties with Thiel and other PayPal alumni like Elon Musk facilitated access to the most promising startups. By pooling expertise and activating networks, their mafia outperformed most peers – directing startups strategically and accelerating growth.
Strengthening Alliances Abroad as Ambassador
In 2019, President Trump unexpectedly nominated Howery as Ambassador to Sweden. Eager to strengthen economic ties with Sweden’s vibrant startup ecosystem while gaining new overseas experience, he took a sabbatical from investing to serve abroad.
Stationed in Sweden for close to eighteen months, Howery focused on initiatives like expanding 5G infrastructure cooperation leveraging Swedish gearmaker Ericsson and facilitating more military exchanges.
He also regularly engaged with Nordic venture capital and startup communities to nurture US ties with rising geographies. While the role allowed little discretion to reinvent policy strategy, Howery made vital incremental progress engaging with business and technology stakeholders.
The ambassador posting expanded his spheres of influence within European innovation circles while showcasing his versatility as a diplomat compared with strictly business-focused PayPal mafiosos.
Principles for Success
Certain key traits and philosophies have enabled Ken Howery to repeatedly create and harness breakout opportunities over the past twenty-plus years:
Surround Yourself with Smart People Obsessed with Problem-Solving
He invested as much in teams exhibiting intellectual curiosity, creativity and tenacity as ideas themselves. He fostered cultures allowing talented people to experiment often and learn rapidly.
Spot Trends Early and Ride Momentum
He identified promising spaces like online payments and social networking so early that risky ideas became slam-dunk growth engines once traction surfaced.
Maximize Options in Uncertain Environments
He diversified across sectors and cultivated optionality to double down on emerging winners. Founders Fund made over 200 investments from biotech to fintech to space.
Activize Networks
He activated his PayPal mafia relationships to gain privileged access to the next batch of promising startups like Facebook.
While luck undoubtedly played some role across his ventures, Ken Howery made his own luck – spotting opportunities, assembling talented teams around promising ideas, and generating momentum further accelerated by well-timed partnerships.
So aspiring entrepreneur, take notes! Because this is the playbook that created billions in value and transformed entire industries over time. Rinse and repeat across enough waves, and perhaps you may also earn that Silicon Valley legend status!
