Reddit co-founder reveals his best investment ever

At the time of the podcast recording, Ohanian said his ether stake is now worth $17.1 million.

The Venture capital firm SevenSevenSix the 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 ring, engagement ring and all that stuff, so it was a good investment,” he said.

Ohanian became engaged to tennis champion Serena Williams in 2016, and the two married the following year.

Biggest investment regrets

While he successfully predicted Ethereum’s growth, financial risks don’t always pay off — and Ohanian talked about a few examples of when he wished he had exited an investment sooner.

Ohanian said one of his biggest investment regrets is Clubhouse, the social audio app that gained mass popularity during the COVID-19 lockdown. The startup has raised more than $100 million and at one point enjoyed a reported valuation of $4 billion.

The app, which has reached more than 10 million downloads, inspired competing features like Spaces on X, then Twitter and Spotify’s Greenroom.

“We had like Series A,” Ohanian said. “And I remember when that multi-billion dollar round came out, I actually put more money in because I’m an idiot.”

However, the post-pandemic return to normal life and socializing outdoors has hit Clubhouse particularly hard, with daily downloads and users dropping significantly through 2021.

But “the one that hurt the most” for Ohanian was TriNet’s online HR platform Zenefits, formerly Zenefits.

After launching in 2013, Zenefits quickly became one of Silicon Valley’s unicorn startups. Within two years, the company raised more than $500 million and was valued at $4.5 billion before it began to unravel amid various controversies.

In 2016, Fidelity slashed the value of several startups in which it had investments, including Zenefits, by as much as 38 percent, The Wall Street Journal reported.

“We could have returned the fund once whenever there was a Fidelity discount,” Ohanian said. “We literally set up an SPV to sell Zenefits, and then the Fidelity downgrade happened and it killed the SPV.”