Joe McCann got into crypto trading and, within two years, he seemed to have it made. McCann’s fund Asymmetric raised money in 2022 from the likes of Marc Andreessen and Circle and, during the crypto boom period that marked Donald Trump’s return to the White House, the fund nearly doubled in value. But then things unraveled.
Joe McCann made a career out of doing things his way.
McCann liked to portray Asymmetric, which had both a venture and a liquid arm, as financially responsible but culturally hip. “I was a DJ and threw raves and had a couple record labels and my brother and I had a clothing line together … I was the CTO at one of the top ad agencies in New York City” before founding Asymmetric, McCann said on the podcast, calling his exposure to the “creative side of humanity” an edge in crypto investing.
For a while, all of this translated to healthy returns. In 2024, the value of Asymmetric’s liquid book swelled from roughly $195 million to $395 million, a person familiar with the firm’s finances told Fortune. Asymmetric’s numbers still lagged Bitcoin’s 121% return that year, however.
As Asymmetric began to struggle in 2025, McCann latched onto a crypto fad known as digital asset treasury companies, popularized by Michael Saylor’s Strategy, formerly Microstrategy. In a July note, he informed investors that “shifting market dynamics” meant Asymmetric would drop its active trading strategy and plow its remaining resources into building a treasury of the cryptocurrency Solana.
But following his catastrophic trip to Tanzania, McCann’s problems now run much deeper than his crypto fortunes. The family of McCann’s late fiancée is demanding answers surrounding her death, and McCann is currently stuck in Tanzania.
In a podcast appearance right in the middle of Joe McCann’s banner 2024, the Asymmetric chief made the case for one key risk all traders need to manage: the risk of losing everything.
“Seeking asymmetry—like, asymmetric upside, limited to no downside—should be coupled with avoiding the risk of ruin,” McCann said.
