My Crypto Conversion, Part One

It didn’t happen overnight. Far from it.

If it has been said that we are in a “crypto winter,” then surely the FTX debacle is something like our winter solstice: the darkest day of the darkest season.

And yet I’m optimistic. I still believe that crypto represents the future. 

Why?

Recently, I realized that in order to explain how I came to be a true crypto believer, there is simply no shortcut. Some people’s crypto stories may be simple –– they bought Bitcoin early and held –– but mine is far from that. I came to crypto and Web3 through a long, winding, and indirect journey: and one that began with deep skepticism, maybe a bit of annoyance, and some meaningful companionship with my partner Bettina Warburg.

It’s a journey that actually requires two posts to unpack, starting with this one. And the story starts some 15 years ago, in Texas.

2008-2010: “You Smell Like A Product Guy.”

I went to UT Austin, the first of my family to attend college. I was working multiple jobs to put myself through school, but had dreams of something bigger. In the mid-2000s, Google was soaring, Facebook had just come out, and PayPal was conquering the payments space –– so of course, I wanted to become a tech entrepreneur. Soon my roommates and I spotted an opportunity: existing payment solutions (like PayPal) couldn’t accommodate political campaigns, which rarely had sufficient operating history. We entered the market with a tool that helped political campaigns navigate this limitation. Soon, using our tooling, politicians were able to capitalize on media cycles and online fundraising, in some cases raising hundreds of thousands of dollars (eventually millions) in mere hours.

Feeling I had struck upon something powerful, in late 2009 I packed up a UHaul and drove to Silicon Valley. Within a year or so, I was showing my growth chart to a venture investor named Mike Maples, who introduced me to LinkedIn’s Reid Hoffman. After a few minutes of conversation, Reid looked me up and down and said, “You smell like a product guy.” He was in –– and I was the Silicon Valley equivalent of a made man. We rebranded the company as Rally.org, which went on to become a major crowdfunding tool for political campaigns, and landed me a spot on the Forbes’s list of “most promising CEO’s under 35.” A one point, 50% of all US political contributions on the internet ran through my company - barrier destroyed.

This is how my story begins: as a Reid Hoffman-certified “product guy,” a mid-aughts tech entrepreneur like the many you read about in those years. My ambitions weren’t small, by any means: I was interested in reinventing political fundraising. But I wasn’t yet interested in the sort of massive problems I would later come to associate with crypto: inventing new currencies, rewriting the entire internet, or fundamentally re-engineering notions as abstract as trust. By 2008, it didn’t occur to me to think about those ideas.

2010-2012: A Broken Payment System Called “Bitcoin”

I probably first heard the word “Bitcoin” around 2009, but it was one of countless buzzwords floating around at Bay Area parties at the time. I took only a passing interest; a founder buttonholed me at a cocktail party one night and told me it was “the future of payments,” and since I was in the payments space, I decided to look into it. I did some Googling, and rapidly it felt like you needed a Ph.D. in computer science degree just to acquire a single Bitcoin. I had spent my young career trying to make transacting money easier, not harder. This Bitcoin thing didn’t feel to me like the future of anything; it just felt like a broken payment system.

But a few years later, I started to pay slightly more attention. A particular political campaign wanted to begin accepting Bitcoin as a form of political donation, and it took the matter to the Federal Election Commission, whose pronouncements we followed very closely at Rally.org. To my surprise, the FEC ruled that political campaigns could accept Bitcoin, as a form of in-kind contribution.

I remember thinking, Huh, if the FEC –– the oldest, stodgiest organization on the planet –– is willing to make that ruling, then… maybe there’s a there there. So I started digging back into Bitcoin again. Still, its uses seemed rather limited. What exactly was so wildly transformative about digital currency? I could see limited uses, but I was unconvinced it was a game-changer. I still remained, basically, what you would call a crypto-skeptic.

2013: A Memorable Flight

In 2013, British Airways invited me to participate in a fun little stunt: a “hackathon in the sky.” One hundred fifty Silicon Valley leaders were invited aboard a flight from San Francisco to London, and I was one of them. We were meant to come up with ideas for how to promote STEM education, a trending (and important) cause.

I was seated in business class, just opposite a young woman who said she worked for a think tank. She didn’t look like a technologist or entrepreneur; she looked like a researcher or academic. She introduced herself as Bettina Warburg.

The young woman worked for something called the Institute for the Future, where she was tasked with forecasting the ten-year future of governance, as a concept. Since I was also working in politics, we had a lot to talk about.

We spoke for the entire 14-hour flight, contributing almost nothing to our poor teammates earnest endeavors to promote STEM. Our conversation was wide-ranging, touching on tech, politics, and culture. It kept coming back to cryptocurrency –– or more properly, crypto more broadly.

At one point, Bettina said: “I think crypto is a major narrative in the future of governance.”

This was interesting. Bettina made persuasive a case that had been promulgated by several theorists: that the technology that undergirded Bitcoin –– so-called “blockchain technology” that I will explain on a technical level in a future post –– could theoretically be used for purposes well beyond payments, including improving governance. For instance, a theorist named Nick Szabo had recently posited that blockchain technology could create what he called “smart contracts,” or binding agreements that could be automatically enforced.

“So you’re telling me you could automate governance?” I asked Bettina. As someone who spent countless hours relitigating simple governance matters with the board of my own startup, I immediately saw the utility of such an option. “A firm is basically a nexus of contracts,” Bettina said. It’s true: by-laws are essentially contracts, or “if-then” statements that govern the firm. The notion of automating some or all of them was exciting to me. My brain whirred.

Our hackathon-in-the-sky team. Bettina (front-right) and I (rear-center) did none of the heavy lifting.

Our plane landed in Heathrow, Bettina and I were separated amidst the hubbub; I proceeded to Berlin, where I had some meetings for Rally.org. For all I knew, my in-flight conversation partner and I would never see each other again. But as the months went by, I thought about our fascinating conversation many times. 

Then, a year and a half later, in early 2015, my life would take a major new direction –– which will be the subject of part two of this post, to come next week.