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.

By July of 2025, Asymmetric’s liquid fund had lost significant value, leading McCann to funnel investors into a new venture that failed to pan out. Then, early this month, reports emerged that McCann’s fiancée, the influencer Ashly Robinson, had died while on vacation with McCann at a luxury resort in Tanzania. Robinson’s death was initially attributed to suicide, but the police have reportedly seized McCann’s passport and are questioning him as part of an ongoing investigation.

McCann and a young influencer

Robinson, who goes by Ashlee Jenae online, took up with McCann in November 2024, one of her Instagram posts suggests. At that time, McCann’s crypto firm was at the zenith of its success. McCann, who did not return multiple text messages seeking comment, had previously been married in 2018 to Shea Jackson, a woman 10 years his junior who worked in marketing. The pair eventually split, and two founders who took venture investments from Asymmetric’s venture fund told Fortune that some of McCann’s stake had been transferred to Jackson. Jackson did not return a request for comment. McCann also has a daughter, according to his X posts.

McCann began bringing Robinson, who was 15 years his junior, to crypto events, and she began posting images of him on her social media accounts. Robinson’s online profiles show her and McCann jetsetting among exotic locations as Robinson embraced the “soft life,” a self-care focused social media trend. “Chapter 31 and I’m exactly where i need to be,” read her final Instagram post, which showed her feeding a giraffe in Tanzania. Two days earlier, the 30-year-old had posted a video of McCann, 45, proposing to her as a lion stalked forward in the foreground.

According to a report from local police, the pair checked into the luxury Zuri Zanzibar hotel on April 6 but, following a disagreement, hotel staff reportedly moved McCann to a room separate from Robinson’s. On April 8, Robinson was found unconscious in her room by a room service attendant and rushed to the hospital. Tanzanian police attributed her death to suicide.

McCann, who has not been formally accused of wrongdoing, had his passport withheld by local authorities and is being questioned by police, according to the police report. Robinson’s family called her death suspicious in a statement.

A crack-up at McCann’s crypto firm

Joe McCann made a career out of doing things his way.

Born in 1980, McCann attended Portland State University, where he studied philosophy, particularly enjoying Nietzsche and Schopenhauer. He spent the first decade-plus of his career in tech and finance, eventually becoming CEO of a software company that was acquired in 2019. After a stint at Microsoft, McCann became a CEO once again after launching a crypto fund—telling himself he would do things “a little bit different this time,” according to a 2024 podcast interview.

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.

In interviews, McCann boasted of notching huge returns on a flash-in-the-pan memecoin called BONK. He boosted his cultural cred by hanging out with the rapper Iggy Azalea and cheerleading that artist’s ill-fated crypto project. He briefly advertised an Asymmetric-themed merch line, with an expensive looking promotional video to boot.

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.

Despite the outsize returns, there was discontent inside Asymmetric. Founding member and key trader Chris Cecere quit the firm despite Asymmetric’s blowout returns in 2024, according to a person who spoke with Cecere. Cecere did not return a request for comment.

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.

Investors were invited to an information session for the company on July 22 but, the same day, an unhappy limited partner posted the firm’s nearly 80% year-to-date loss on X. Soon after, the Solana scheme was scrapped. One former Asymmetric investor told Fortune that as the liquid fund wound down, the return they received from the fund was less than the principal they had invested. Today, Asymmetric’s website lists two venture funds and a special purpose vehicle for Circle equity. The “Team” page on Asymmetric’s website has been taken down, and an Asymmetric general partner did not return a request for comment.

Even as Asymmetric floundered, McCann remained active in the crypto world, often posting several times a day to his more than 100,000 X followers. In March of this year, the crypto firm MG Stover acquired Asymmetric Information, a crypto analytics firm founded by McCann.

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.