Accidental disruption: Max Levchin discusses how close PayPal was to never existing at all; Max Levchin: I learned to code in the Soviet Union by writing clones of Tetris and Snake.. on paper

Accidental disruption: Max Levchin discusses how close PayPal was to never existing at all

ON MARCH 13, 2014

PayPal’s status as one of the most successful pre dot-com crash companies is beyond dispute. But for the billions in value that it created and the impact that it’s had in revolutionizing digital payments, it’s remarkable to consider how close the company came to never existing.

It wasn’t just teetering on the brink of insolvency, something that every startup encounters at some point. Rather, PayPal was never intended to be a payments company, but started out as an encryption solution for early Palm Pilots. The little known stories of the multiple pivots that led the company to the payments promised land is nothing if not remarkable.

Speaking at tonight’s PandoMonthly fireside chat in San Francisco, PayPal co-founder and former-CTO Max Levchin shared the story of his first meeting with Peter Thiel. As a recent computer science graduate of the University of Illinois, Levchin attended a small lecture by Thiel at Stanford and ultimately ended up pitching him over breakfast a few days later.

“I was one of the first developers of the PDA… and I was like one day, everyone is gonna use these at work,” Levchin recalls telling Thiel. “[I said] what do you think they’re gonna do when the man is gonna try to read their documents, when their customers are gonna steal all their data? They’re gonna encrypt it. And I’m gonna invent all the crypto.”

Thiel bought into the concept and wrote the first check for the company that would ultimately become PayPal, from his hedge fund meant to invest in public stocks. After developing mountains of “very ingenious” code, in Levchin’s words, the pair pitched Palm on embracing the software and were shut down summarily.

“They were like, ‘No one will use this in the enterprise, this is a personal device, it has calendars and notes,’” Levchin says. “We were distraught for the first time because we had to go out and raise money.”

After a desperate brainstorming session centered around other uses for encryption code on handheld devices, Levchin and Thiel settled on the concept of beaming digitally-signed, secure personal IOUs between palm pilots using their infrared ports.

“The payments thing began very earnestly with these IOUs,” Levchin says.

The idea was so revolutionary that PayPal ultimately raised a $6 million Series A round in 1999 from BlueRun Ventures. The company even beamed the capital for its first round between Palm Pilots, marking the first time in history money was ever transferred electronically. Although it was far less trendy at the time, PayPal was also likely the first ever mobile-first company as well. It was at Reid Hoffman’s insistence and only for demonstration purposes that the company even built a Web version of its product.

“We were like, ‘here’s how it works if you don’t have a Palm Pilot, but go get yourself a palm pilot and beam some payments,’” Levchin says. “We were very throwaway about the non-mobile demo on the website, it was really poorly built… Reid was like, not everyone has a Palm Pilot, I think they have about two million units in circulation, the Web is bigger than that.”

In one of the most astounding examples of unintended consequences, it was the Web version that caught on – thankfully given that it was approximately 15 years before handheld devices really became mainstream. The earliest influxes of meaningful payment volume to PayPal came from eBay, Levchin recalls, but the company’s first reaction was to try to ban it out of fear of being associated with a secondhand marketplace. It wasn’t until a user emailed asking for a copy of PayPal’s logo to feature on its listings pages that the company realized that there may be an opportunity worth exploring in ecommerce.

As luck would have it, this realization coincided with the altogether unrelated decision by PayPal to offer new users a $10 credit for signing up and another $10 for referrals. By making withdrawals more difficult than deposits, PayPal was able to keep much of this capital in the system and, in effect, seed the marketplace. But the byproduct was that many eBay merchants decided to pocket the $10 and in turn offer buyers free shipping.

“[Free shipping] is what [buyers] crave – they don’t understand $10 off, but they get free shipping, they love that” Levchin says. “That was basically the original explosion of PayPal on eBay, everyone got free shipping.”

Of course this was the beginning of big things for PayPal and set the company off on a path that would ultimately see it being acquired by eBay for $1.5 billion just two years later. Like many startups, there were countless instances along the way in which PayPal could have failed. What’s remarkable, however, is just how unintentional the concept of revolutionizing the payments industry really was.

It’s often said that it’s better to be lucky than good. Fortunately for PayPal, Levchin, Thiel, and the company’s other early execs were both lucky and good. It wasn’t just the company and its investors that won big, however. Silicon Valley has been impacted significantly by the emergence of the eponymous PayPal mafia that the company’s success spawned.


Max Levchin: I learned to code in the Soviet Union by writing clones of Tetris and Snake…. on paper

ON MARCH 13, 2014

Max Levchin learned to code in the 80s, while growing up in Soviet-controlled Ukraine. He left the country by train after the Chernobyl nuclear disaster into now occupied Crimea in 1986, before his family finally fled to Chicago under political asylum in 1991.

At tonight’s Pando Monthly event in San Francisco, he talked about his journey — both literally and metaphorically.

Top of Form

Bottom of Form

Growing up in Kiev, Levchin’s mother worked in the radiology lab for the Institute of Food Science, testing pollution levels in foodstuffs. A formative moment in Levchin’s life was when the Soviets flew a primitive EP11 computer in for his mother to use so she didn’t have to write things down. It was this device, and a primitive scientific calculator on which Levchin first came to understand the power of programming. Speaking about the calculator (his favorite device because “I could take it home with me”) he said…

“There was keycode ‘K’ [on the calculator], the first letter of the Russian word for indirect. You use the key to say, ‘take whatever is in that register and do whatever it is you want to do with that,’ so you can refer to things that you don’t know about yet. The machine could be instructed to do things in the future.”

Levchin was inspired. He didn’t want to be a teacher anymore: he wanted to be a computer programmer.

It would be years before Levchin would have access to a computer again. “The vast majority of programming I did, I was… working on [paper] notepads. I would write programs that would span [multiple] notepads. I wrote a clone of Tetris, a clone of snake,” Levchin said.

“I have no idea if they were good because I was not able to actually run them.”

All of his early programming efforts used machine code, not BASIC or anything similar. “There was no easy way. No shortcuts. There was not an option to write a go to statement. It was very, very explicit. Very procedural programming. It probably made me slightly elitist. It certainly made me tenacious as I never really had another option,” he said.

Levchin laughed when asked about whether his background had made more insufferable as a CTO.



Max Levchin: Slide “drained the crap out of me”

ON MARCH 13, 2014

In the year between leaving PayPal in 2003 and starting Slide in 2004, Max Levchin was in bad shape. The woman he would eventually marry took a break from their relationship. Friends would find themselves on the receiving end of long rants and have to excuse themselves to go back to work, because it was Tuesday afternoon and they still had jobs.

At tonight’s Pando Monthly, Levchin said it was his desire to escape the post-PayPal shadow that led him to starting Slide, a social apps and games company.

“I think it would have always been a disappointment because I just don’t care about games. I played a really good games company CEO because I had to. But it drained the crap out of me. I couldn’t play games if my life depended on it,” Levchin said.

Pointing to his PayPal co-founder, Elon Musk, Levchin said that without [enthusiasm] there’s always a ceiling to how far you can go. “Elon wants to die on Mars. Not because it is fun to die, but because that is fucking important,” he said.

Slide had a successful exit, selling to Google in 2010. Even if he couldn’t admit it to himself at the time, Levchin said that PayPal’s legacy impacted how he thought about business and what he felt that success ultimately looked like.

“I measured success since the day I started building start ups in the number of people that used my product and thought it was good,” Levchin said. Slide was popular, at one point one of the 10 biggest entities on the web.

“But what I was secretly measuring myself against, that goal was to top PayPal. The goal was to get a big group of people to benefit from what I’m working on every day. But in the back of my I’m thinking it has to be that and bigger than PayPal.”

In 2010, Levchin had two options for Slide: sell or re-capitalize the company and accept some blood letting. He looked around his executive team and saw that people were exhausted. The hopes for big success were fading. He never thought about leaving, but worried that people who’d worked hard might leave for years with nothing to show for it.

“I finally said, look, I may have been leading you through the desert but here’s a bit of an oasis,” Levchin said.

Was he relieved when Google stepped in and bought Slide?



About bambooinnovator
Kee Koon Boon (“KB”) is the co-founder and director of HERO Investment Management which provides specialized fund management and investment advisory services to the ARCHEA Asia HERO Innovators Fund (, the only Asian SMID-cap tech-focused fund in the industry. KB is an internationally featured investor rooted in the principles of value investing for over a decade as a fund manager and analyst in the Asian capital markets who started his career at a boutique hedge fund in Singapore where he was with the firm since 2002 and was also part of the core investment committee in significantly outperforming the index in the 10-year-plus-old flagship Asian fund. He was also the portfolio manager for Asia-Pacific equities at Korea’s largest mutual fund company. Prior to setting up the H.E.R.O. Innovators Fund, KB was the Chief Investment Officer & CEO of a Singapore Registered Fund Management Company (RFMC) where he is responsible for listed Asian equity investments. KB had taught accounting at the Singapore Management University (SMU) as a faculty member and also pioneered the 15-week course on Accounting Fraud in Asia as an official module at SMU. KB remains grateful and honored to be invited by Singapore’s financial regulator Monetary Authority of Singapore (MAS) to present to their top management team about implementing a world’s first fact-based forward-looking fraud detection framework to bring about benefits for the capital markets in Singapore and for the public and investment community. KB also served the community in sharing his insights in writing articles about value investing and corporate governance in the media that include Business Times, Straits Times, Jakarta Post, Manual of Ideas, Investopedia, TedXWallStreet. He had also presented in top investment, banking and finance conferences in America, Italy, Sydney, Cape Town, HK, China. He has trained CEOs, entrepreneurs, CFOs, management executives in business strategy & business model innovation in Singapore, HK and China.

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