Reddit cofounder reveals his best-ever investment — and his biggest flops
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- Alexis Ohanian said his early investment in Ethereum's pre-token sale is now worth $17.1 million.
- The Reddit cofounder called it his best-ever investment.
- Ohanian cited past investments in Zenefits and Clubhouse as two that didn't pan out.
Alexis Ohanian recently revealed his single-best investment — and also some financial moves he now regrets.
In a podcast interview with venture capitalist Harry Stebbings, the Reddit cofounder said that he made millions from investing early in Ethereum.
Ohanian said he invested $10,000 at the company's pre-token sale — which turned out to be a highly lucrative move as the company's cryptocurrency, ether (ETH), is now the second largest in the world by market cap.
At the time of the podcast recording, Ohanian said his ether stake is now worth $17.1 million.
The SevenSevenSix venture capital firm founder also said that, along with some ether, he also sold a lot of bitcoin — another profitable move for a more romantic reason.
"I sold it for a wedding and engagement ring and all that stuff, so it was a good investment," he said.
Ohanian got engaged to tennis champion Serena Williams in 2016, and the two married the following year.
Biggest investment regrets
While he successfully predicted Ethereum's rise, financial risks don't always pay off — and Ohanian talked about some examples of when he wished he had exited an investment sooner.
Ohanian said one of his biggest investing regrets is Clubhouse, the social audio app that gained mass popularity during the COVID-19 lockdown. The startup raised over $100 million and at one point enjoyed a reported $4 billion valuation.
The app, which reached over 10 million downloads, inspired competing features such as Spaces on X, then Twitter, and Spotify's Greenroom.
"I had like the Series A," Ohanian said. "And I remember when that multibillion-dollar round came up, I actually put more money in because I'm an idiot."
However, the post-pandemic return to normal life and outdoor socializing hit Clubhouse particularly hard, with daily downloads and users dropping significantly by 2021.
But the "one that hurt the most" for Ohanian was the online HR platform TriNet Zenefits, formerly called Zenefits.
After launching in 2013, Zenefits quickly became one of Silicon Valley's unicorn startups. Within two years, the company raised over $500 million and was valued at $4.5 billion until it started unraveling amid various controversies.
In 2016, Fidelity marked down the value of several startups it had investments in, including Zenefits, by as much as 38%, The Wall Street Journal reported.
"We could have returned the fund once over whenever the Fidelity markdown was," Ohanian said. "Literally putting an SPV together to sell Zenefits, and then the Fidelity markdown happened, and it killed the SPV."
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