Kevin Ryan knows how to change his mind.

Consider psychedelics: Ryan—often called “the Godfather of NYC Tech”—was once skeptical that psychedelics could be viable treatments for depression or PTSD. But in 2018, he read Michael Pollan’s How to Change Your Mind and encountered a wave of data. Now, he’s a key backer of the Yale Center for Psychedelic Research and cofounded Transcend Therapeutics, a psychoactive drug maker that sold in June for $1.2 billion.

“What I think about is where the world’s going five to ten years from now, and then we need to make a bet when it’s not obvious,” Ryan said. “If it’s obvious, it’s worth $20 billion and it’s too late. So, we’re making bets early. Psychedelics are a perfect example of that.”

Ryan, throughout his career, has cofounded dozens of companies (including MongoDB, Business Insider, Gilt Groupe, and Zola). Many began as incubations through the venture firm he originally founded as a family office in 2007, AlleyCorp. The firm took on outside investors for the first time in 2024, with a $250 million fund that Term Sheet broke the news on. (A source familiar with the firm’s financials said that previous investments have generated an all-time 60% IRR.) Now, as the venture capital landscape has evolved rapidly over the last couple of years, AlleyCorp is back with its $335 million second fund, the firm exclusively told Fortune.