The Winding Path of Silicon Valley Insider Andrew McCormack

Andrew McCormack has never quite captured the public imagination like his longtime friend and business partner Peter Thiel. But over 20+ years spent crisscrossing the tech and finance worlds, McCormack has quietly become one of the most consistently successful investors that even industry insiders barely know. His journey from banking PayPal‘s founders to writing seed checks to the next generation of fintech unicorns reveals much about the ever-evolving DNA of Silicon Valley itself.

Let‘s trace the origin story and winding career path that molded McCormack into a quintessential Valley insider.

A Pedigreed Start

Long before technology dominated life in Northern California, McCormack was an ambitious teenager on the East Coast determined to gain that elusive acceptance letter from an elite university. He secured his prestigious academic pedigree at the Loomis Chaffee prep school before heads down to the University of Pennsylvania‘s Wharton School of Business in 1994.

Emerging in 1998 with an Ivy League degree in political science, McCormack appeared well-positioned for a consulting job or safe corporate gig. But the tales of overnight internet riches lured him to ditch that playbook and head West to sunny California just as the dot-com frenzy neared its peak. The tech gold rush was on and digital pioneers with more ideas than business acumen badly needed operators like McCormack to turn their visions into reality.

His Ivy League connections landed McCormack meetings all over San Francisco and Silicon Valley as he searched for the right startup ride. In early 2001 opportunity came knocking when an early PayPal employee departed and 29-year old CEO Peter Thiel went hunting for a replacement. Enter 25-year old Andrew McCormack who smoothly slid into an operational role as employee #13 at a company on the verge of revolutionizing digital payments.

Betting on PayPal‘s Breakthrough

PayPal represented a classic early internet company with brilliant technical founders and an earth-shattering idea but little business acumen to realize their global vision. Enter operational wunderkinds like Andrew McCormack who took Max Levchin and Peter Thiel‘s payments concept and rapidly built the business model, compliance infrastructure, and plan to raise significant venture funding.

The talented Mr. McCormack quickly gained the trust of executives like Peter Thiel before proving instrumental in charting PayPal‘s path to the public markets in the run-up to their 2002 IPO. Yet after weathering the dot-com crash, that offering turned instead into a $1.5 billion exit with young eBay acquiring the payments upstart to bolt-on to their online marketplace empire.

In the span of less than two years, McCormack‘s gamble on PayPal looked genius as former colleagues like Elon Musk, Peter Thiel and Reid Hoffman tapped their newfound fortunes to found SpaceX, Palantir and LinkedIn respectively. For his part, McCormack parlayed trusted status as Thiel‘s right-hand staffer into a VC career full of blockbuster deals over the next 20 years across Silicon Valley‘s evolving landscape.

From Global Macro to Fine Dining

Given their tight partnership enabling PayPal‘s success, it was little surprise that McCormack joined up with Peter Thiel‘s next venture, global macro hedge fund Clarium Capital in 2002. However, perhaps realizing sooner than his boss that scratch paper models were no match for fast-moving markets, McCormack switched gears dramatically in 2003.

Alongside several friends with no prior restaurant experience, McCormack launched the Sprezzatura Restaurant Group which delivered two popular Bay Area eateries before selling at the market‘s peak in 2008. This detour showed McCormack‘s operating chops by building and exiting a bricks-and-mortar business requiring processes and attention to detail that web-based startups rarely emphasize. With an appetite to get back into high-growth technology, McCormack wouldn‘t have to wait long before Thiel came calling again.

Rejoining Forces to Search for the Next Big Thing

By 2008, PayPal co-founder Peter Thiel already regretted shifting away from the entrepreneurial scene to launch a massive hedge fund. As the global economy careened into crisis that year, he refocused on investing in innovative startups via Thiel Capital as Facebook and SpaceX hinted at his golden touch as a seed-stage VC. Thiel‘s longtime right-hand man Andrew McCormack was a natural fit to identify promising student entrepreneurs and niche technologies while leaving the Hollywood-esque drama to his famous boss.

This next chapter let McCormack float between Thiel‘s ever-increasing portfolio companies in search of the next PayPal while getting his feet wet with corporate development roles at Yahoo! and eCount. But soon it would be time to build something of his own again. Thus in 2010, McCormack and two other Thiel proteges spun out to found Valar Ventures with the mission to systematically identify software‘s next unicorns.

Finding Today‘s PayPals

As newly minted VCs coming out of the PayPal mafia family tree, the Valar Ventures gang focused on backing startups leveraging technology to drive transformation across industries. They key criterion was for disruption-ready business models versus chasing hype in AI, crypto or other fleeting trends.

This laser focus led Valar to uncover stellar companies like global money transfer platform Wise early on alongside other upstarts aiming to build the picks and shovels enabling innovation from banking to accounting software FINTECHS. Check out the list below for a sample of fintech players that may be tomorrow‘s PayPal thanks to backing from McCormack and his team.

McCormack‘s journey has seen him traversenetscape‘s boom and bust before finding his tribe with PayPal‘s mafia. Whereas most washed out after the dot-com crash, his resilience and multiplying connections positioned perfectly to latch onto successor tech trends like social and crypto. Provided he maintains proximity to payers like his longtime friend Peter Thiel, expect McCormack to keep identifying emerging niches before the mainstream catches on.

With a running start toward the half-century mark, the indefatigable McCormack appears to have plenty left in the tank. Wherever the nexus of technology and finance migrates next, this iconoclast turned influencer turned global venture investor will be there hunting for outstanding founders before anyone else. PayPal made McCormack a millionaire on paper, but his second act may still shine brightest if one of Valar‘s bets becomes fintech‘s next hundred billion dollar baby!