Just a decade removed from his time as an MIT undergrad, the Chinese immigrant was riding high in the crypto world after landing on the Forbes 30 Under 30 list, and he had his own blockchain-focused venture firm, Shima Capital. In a short time, Gao raised $200 million from finance heavyweights like Bill Ackman and prominent crypto firms including Dragonfly and Galaxy, soon becoming one of the most active investors in crypto by participating in more than 300 deals. Gao’s ascent was meteoric. But he also cut crucial corners. Gao has not yet been charged with any crime but the onetime rising star of the crypto scene is struggling to raise further capital and his firm has seen an exodus of top talent. He began his financial career at Morgan Stanley doing mergers and acquisitions. In his spare time, he invested in startups, often collaborating with a well-connected fellow entrepreneur named Adam Struck. Gao worked at the venture giant New Enterprise Associates and briefly enrolled at Stanford’s business school before dropping out to join Struck’s venture firm in Santa Monica full-time. In late 2022, Shima’s investors began to discover the existence of the ownership structure, as well as the valuation disparities, leading them to raise alarm bells with Shima’s management. Shima’s compliance issues could also have legal ramifications for Gao and his company.