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Eric M. Jackson: The PayPal Pioneer Shaping Tech‘s Future

As one of the earliest employees of PayPal, Eric M. Jackson played a crucial role in building the online payments juggernaut that would go on to shape the future of money and technology. A member of the famed "PayPal Mafia" alongside titans like Elon Musk, Peter Thiel, and Reid Hoffman, Jackson has leveraged his experience into a dynamic career as an entrepreneur, investor, author, and tech policy commentator.

While he may not be a household name on par with some of his PayPal peers, Jackson has quietly become one of the most influential and multifaceted figures in the technology world. His insider account of PayPal‘s meteoric rise and his incisive critiques of Silicon Valley have established him as a leading voice on the industry‘s past and future.

Formative Years at Stanford and Arthur Andersen

Born in the late 1970s, Eric Jackson grew up immersed in the dawning digital revolution. A precocious student, he enrolled at Stanford University in the mid-1990s, graduating with honors in economics in 1998.

At Stanford, Jackson honed his analytical skills and rubbed elbows with brilliant classmates, many of whom would go on to the upper echelons of Silicon Valley. Foreshadowing his later success, he was an active member of student organizations like the Stanford Review, a conservative publication co-founded by Peter Thiel.

Fresh out of college, Jackson cut his teeth in the business world at blue-chip accounting firm Arthur Andersen (before its collapse in the Enron scandal). As a financial consultant specializing in litigation and corporate restructuring, he gained valuable experience navigating high-stakes deals and turnaround situations.

But the entrepreneurial Jackson soon felt the pull of the red-hot dot-com boom. A nascent online payment startup called PayPal was beginning to disrupt the stagnant banking industry – and Jackson wanted in on the action. In 1999, he joined PayPal as one of the company‘s first 20 employees, working under then-CEO Peter Thiel.

PayPal‘s Revolutionary Rise

When Eric Jackson came aboard, PayPal was still a scrappy startup burning through cash. But fueled by an unconventional vision to create a new digital currency, the company was poised for explosive growth.

With his keen grasp of the business and tireless work ethic, Jackson quickly emerged as a rising star at PayPal. He ascended from a business development role to leading the marketing team as the Senior Director of U.S. Marketing and eventually President of Marketing.

At a critical juncture for the startup, Jackson devised and executed a brilliant strategy to convert the power sellers on eBay‘s online marketplace into PayPal users. By forging a close partnership with eBay, PayPal was able to tap into a massive network of buyers and sellers who needed a trusted way to send and receive payments.

The eBay alliance proved to be the rocket fuel PayPal needed to achieve escape velocity. Between 2000 and 2002, the company‘s user base skyrocketed from 1 million to 20 million as e-commerce exploded.

Another pillar of PayPal‘s rapid rise was the overhaul of its pricing model led by Jackson. Under the new regime, users could send money for free and PayPal only charged to receive commercial payments – a transformational move to onboard customers en masse.

"We needed to do something bold and innovative to provide a clear reason for signing up. So we made the decision that we were just going to make payments free for everyone. That turned out to be hugely advantageous." -Eric Jackson on PayPal‘s pricing strategy

Behind the scenes, Jackson and his colleagues were locked in an all-consuming battle to scale the company amid cut-throat competition and mounting regulatory scrutiny. In his 2004 book The PayPal Wars, Jackson vividly recounts the "insanely intense" culture of 18-hour workdays, power struggles, and eureka breakthroughs that defined PayPal‘s against-all-odds triumph.

After a blockbuster IPO in early 2002, PayPal was acquired by eBay just a few months later for a whopping $1.5 billion. The deal minted millionaires out of the founding team and cemented PayPal‘s place in the annals of Silicon Valley disruption.

Reflecting on the acquisition in The PayPal Wars, Jackson describes conflicting emotions of exhaustion and elation: "We had built an amazing business, and I felt fortunate to have been a part of it. At the same time, a voice in the back of my head reminded me that we were selling at what was probably a low point in our potential."

Networks Effects of the PayPal Mafia

The famous PayPal Mafia has often been hailed as one of most extraordinary collections of business talent in history – and for good reason. By one estimate, the group‘s members have been involved in companies with an aggregate valuation of over $500 billion.

After the sale to eBay, PayPal‘s overachiever alumni diaspora scattered throughout tech to found and fund an astonishing number of industry-shaking startups. The sheer magnitude of ventures spawned by ex-PayPal employees is staggering:

  • Tesla and SpaceX (Elon Musk)
  • Palantir and Founders Fund (Peter Thiel)
  • LinkedIn (Reid Hoffman)
  • YouTube (Steve Chen, Chad Hurley, Jawed Karim)
  • Yelp (Jeremy Stoppelman, Russel Simmons)
  • Yammer (David Sacks)
  • Slide (Max Levchin)
  • Kiva (Premal Shah)
  • And dozens of other startups and VC firms

As acclaimed author and Silicon Valley historian Margaret O‘Mara put it: "PayPal created the template of the modern tech company…They were the first startup that really identified as a network, not just a product or a company, but an interwoven network of people and ideas."

Although he may not have the same marquee name recognition as some PayPal peers, Eric Jackson has been a vital node in that influential network. Both as an active angel investor and a connector, he has leveraged his PayPal pedigree and relationships into an impressive array of successful ventures.

New Frontiers in Media and Enterprise Software

After his tour of duty at PayPal, one of Jackson‘s first major undertakings was to give an insider‘s account of the company‘s turbulent history in the 2004 book The PayPal Wars: Battles with eBay, the Media, the Mafia, and the Rest of Planet Earth.

The gripping tell-all was hailed as a "must read" by tech luminaries and earned praise for its candid depiction of the personalities and power struggles behind PayPal‘s ascent. Demonstrating Jackson‘s flair as a storyteller, the book established him as perhaps the foremost chronicler of the PayPal Mafia‘s early exploits.

Emboldened by the book‘s success, Jackson ventured into the media world himself by launching the conservative online publishing upstart World Ahead Media in 2004. With Jackson at the helm as CEO, World Ahead released books and documentaries aimed at promoting free market ideas and challenging what he saw as liberal orthodoxy.

The company‘s most notable releases included works by right-wing firebrands like David Horowitz, Dinesh D‘Souza and Michelle Malkin. While World Ahead‘s unapologetically partisan stances limited its mainstream reach, Jackson grew the niche outfit to nearly $1 million in annual revenue within a few years. In 2008, the company was sold to the arch-conservative (and conspiratorially-tinged) website WorldNetDaily.

Despite the politically charged nature of World Ahead, its acquisition capped off an entrepreneurial success for Jackson. And he was far from done making his mark on the worlds of tech and business.

Returning to his Silicon Valley roots in 2010, Jackson co-founded CapLinked, a startup aiming to streamline the cumbersome process of managing financial deals and documents. Built on his experience wrangling high-stakes transactions at PayPal and Andersen, Jackson designed CapLinked as a "virtual data room" for enterprises engaged in capital raises, asset sales, M&A, and other complex dealings to securely share information.

Under Jackson‘s leadership as CEO, CapLinked has grown into a thriving software-as-a-service business used by 250,000+ professionals and over half of the Fortune 1000. With clients ranging from tech stalwarts like Dropbox and Roku to major banks and investment funds, CapLinked has established itself as a vital tool powering financial activity behind the scenes.

Crypto Evangelist and Tech Investor

More recently, Jackson has trained his sights on the white-hot world of cryptocurrency and blockchain technology. In 2018, he founded TransitNet to tackle one of the biggest challenges facing the burgeoning crypto economy: the lack of secure and user-friendly solutions for managing digital asset ownership.

Leveraging cutting-edge cryptography and distributed ledger technology, TransitNet is building a decentralized title registry system to establish "proof of ownership" for crypto wallets and coin holdings. As the ecosystem of bitcoin, ethereum and other digital tokens goes mainstream, Jackson sees an acute need for a "single source of truth" to prevent fraud and protect consumers.

While TransitNet is still in its early stages, the venture represents Jackson‘s hallmark foresight and willingness to dive headfirst into uncharted tech territorry. With the total value of the cryptocurrency market now exceeding $1 trillion, he is betting that solving the asset ownership conundrum could become a major business.

Not content to merely build startups, Jackson has also become an active tech investor through his hedge fund EMJ Capital. Launched in 2017, the Toronto-based firm manages a concentrated portfolio of long and short positions in public tech companies.

With assets approaching $100 million, EMJ looks for "technology companies undergoing rapid change and innovation" in which to deploy capital and engage in activist campaigns. Some of its major holdings have included Netflix, Facebook, Alibaba, Square and Twitter.

As a frequent commentator on financial media outlets like CNBC and Fox Business, Jackson argues that public tech companies are often fundamentally misunderstood and mispriced by the market. Drawing on his operating experience and network of Silicon Valley insiders, he takes high-conviction positions and pushes management teams to make bolder moves to drive shareholder value.

Conservative Crusader Against Big Tech

Although he has achieved entrepreneurial success across a range of tech domains, Eric Jackson is hardly a cheerleader for the industry‘s reigning giants. Once a beneficiary of the internet‘s democratic promise, he has emerged as a vocal critic of what he sees as an alarming concentration of power in the hands of a few unaccountable tech corporations.

As a frequent talking head on conservative outlets like Fox News and Newsmax, Jackson contends that companies like Google, Facebook and Amazon have accrued far too much control over people‘s personal data, online experiences and even political views. He alleges that Big Tech‘s increasingly partisan censorship of voices on the right represents an existential threat to free speech.

"The executives at these companies are not elected, but in some ways are more powerful than many government officials. We need to have a serious debate about the role we want a handful of corporations to have in controlling information and reshaping society." -Eric Jackson

While still an avowed believer in free market principles, Jackson has called for updated antitrust regulations to foster more competition in the tech industry. He points to the overwhelming market share of Google in search and online advertising as a textbook example of monopolistic behavior that should invite government scrutiny.

Drawing on his experience as an outnumbered conservative in liberal-leaning Silicon Valley, Jackson argues that dominant tech platforms have stifled the viewpoint diversity necessary for innovation to thrive. Citing PayPal‘s initial hostility from regulators and the banking establishment, he believes that today‘s incumbents are pulling up the ladder behind them.

As more policymakers and the public at large awaken to the unintended consequences of a tech landscape controlled by a few coastal behemoths, Jackson‘s brand of right-leaning tech skepticism is gaining traction. With the threat of antitrust lawsuits looming over Big Tech, his call to break up powerful companies in the name of fostering competition may not sound so crazy after all.

A PayPal Posterboy Eyes What‘s Next

Now in his mid-40s, Eric Jackson has come a long way from the ambitious young Stanford graduate who took a flyer on an unknown payments startup. With an estimated net worth in the millions (albeit a far cry from centibillionaires like Elon Musk), he has earned his place in the rarefied ranks of the PayPal Mafia.

But for the restless serial entrepreneur, the trappings of tech moguldom seem to hold little appeal. True to his risk-taking roots, Jackson still relishes the challenge of building disruptive new ventures from scratch and evangelizing the next wave of game-changing technologies.

As a proud husband and father of a young daughter, Jackson has indicated that he tries to maintain more work-life balance than in his early startup days. But he still keeps an exhausting schedule between his CEO duties at TransitNet, oversight of EMJ Capital, and frequent media appearances and speaking gigs.

Looking ahead, Jackson is closely monitoring the evolution of crypto/blockchain technologies and the decentralized "Web3" ecosystem that many believe will reshape the internet as we know it. Ever the PayPal pugilist, he seems to savor the coming clash between the crypto upstarts and entrenched tech titans and financial institutions.

Reflecting on the lessons of his own remarkable journey, Jackson argues that entrepreneurs must be prepared to weather blistering attacks from the establishment.

"If you‘re doing something worthwhile, it‘s going to be controversial. You have to have the confidence and conviction to see it through. In my experience, the biggest opportunities are the ones that very few people, including experts, can see in the beginning." -Eric Jackson

Armed with his hard-won knowledge from the front lines of the dot-com revolution, Eric M. Jackson remains a uniquely credible and provocative voice on the future of technology. As the boundaries blur between tech and every other sphere of life, his insights on innovation, disruption and policy are essential reading for founders, investors and anyone trying to make sense of the digital world he helped create.