The insane story of Dan Conway.

You know those crazy videos where someone goes skydiving or performs parkour stunts on the edge of a skyscraper? The ones that give you sweaty palms just watching them?

That’s what it feels like reading about a middle-aged guy with a family who sank his entire fortune into a brand spanking new digital currency that just popped into existence.

But that’s exactly what Dan Conway, a former middle manager slaving away in corporate America did back in 2016. He put his family’s life savings into a new crypto called Ethereum.

Now, in retrospect, this may not seem like the absolute worst, most insane idea anyone’s every had to make a fortune. Since its inception at around $2 in 2015, Ethereum has climbed to as high as almost $4700 back in November, 2021. It currently sits at just over $2300.

But we’re talking almost ten years ago. When Bitcoin and the entire crypto market were still in its toddler years. It was the wild west.

Conway’s idea was partly inspired by Bitcoin’s shocking success in 2013, when it ran from under $100 to over $1000 in a matter of months. Could Ethereum perhaps replicate the same sort of mindboggling returns? That was the big question.

At the time, Conway was 45, “quietly desperate,” and slaving away as a corporate middle manger in San Francisco, making $150,000 a year. He was married with three kids, had about $100,000 in savings, and some built-up equity in his home. While not destitute by any means, Conway was like a lot of people willing to do anything to escape the 9–5 grind. Making matters worse (or better, depending on your POV), Conway had a somewhat addictive personality. He’d struggled with alcohol and drugs. He was even in a 12-step program.

But he was able to channel his “mania” into a new obsession — this strange new cryptocurrency. As he learned more, he became more confident that ETH could potentially replicate Bitcoin’s success from years earlier. His belief was partly due to his experience working for Macromedia in the ’90s, the company behind Flash. He was familiar with how a new tech product with the right developers can suddenly catch on and rapidly soak up market share.

Still, ETH was so new that even his friends in the San Francisco tech world didn’t believe in it.

“Most of my friends in tech — folks working at places like Google, Apple, and Uber — were dismissive of blockchain. Few of them had heard of Ethereum. When I told a buddy of mine that I was considering investing in cryptocurrency, he broke out in laughter, as if I’d admitted I was hedging my future on Smurfberries or Scooby Snacks.” (Source)

Nonetheless, in mid-2016, Conway went to his bank Wells Fargo and transferred his family’s entire life savings to the new crypto exchange Gemini (founded by the Winklevoss twins) for nearly $7,000 ETH tokens, at a price of about $14.

Then something catastrophic happened.

All of a month later an Ethereum project got hacked and Conway’s $100,000 investment sank to less than $40K. It was a harsh welcome to the world of crypto. While most people might have capitulated, the sudden reversal only cemented Conway’s belief in ETH’s potential. He doubled down. Big time. By sinking over $200,000 of home equity into the dip. Now he was all in at $300K but at an average price of about $11 a token.

As it turns out, the frightening flash crash was the pivot point. Over the course of the next year crypto saw a return of the bull market. Ethereum climbed from its bargain basement price of $8 to over $1,300.

By the time Conway cashed out in late 2017 into early 2018, his risky bet had turned into $10 million.

However, there was a huge personal toll to pay on the path to decamillionare status. Conway admits to a lot of emotional volatility, obsessively tracking ETH’s price, and late soul-searching nights worrying about his crypto account getting hacked. He was fired from his job. He even wound up in the emergency room with a “panic event.”

I find Dan Conway’s story equally thrilling and inspiring. Even somewhat relatable. I had some success with Ethereum, Bitcoin, and other cryptos myself back in 2020. It was reading stories like his that motivated me to finally step outside the comfort zone of my more conservative investing style, and take a little risk on this new asset class. I started with Bitcoin when it was under $10,000, and then Ethereum when it was sub-$500. While my returns aren’t nearly as high as Conway’s, I’ve still done okay. Time will tell whether the crypto market will undergo another face-melting run like before.

Conway is a unique personality. Very few people would be willing to go all in on something so unproven as a new crypto token like he did. Especially at 45, with three kids, a wife, and a mortgage, living in one of the most expensive areas of the country. There’s something very admirable about that. Reminscent of the Old West gold rush prospectors, or the family’s that traveled West on the Oregon trail.

However, Conway is very aware of his good luck:

“I banked everything I had on a relatively unproven technology and got out at the right time. For every story like mine, there are hundreds of others about people who lost it all. I know that could’ve easily been me.

At the same time, I’m no blackjack player. My investment wasn’t purely a blind gamble that came up aces. I was, and am, a true believer in crypto — and I had the right mix of courageousness and craziness to take a big risk.” (Source)

Since striking it rich in crypto, Conway has retired to a more normal life. He’s written a book called Confessions of a Crypto Millionaire. If you want to read more, you can also check out his first-person account of all the action in The Hustle.

Would you be willing to go all in on an investment you believe in? Was Conway crazy or ahead of the curve?