In this episode of The Collector’s Compass, Alyx sits down with one of his closest friends and a trusted voice from both his personal and professional life, Eric Sterns, to unpack a question more people are asking quietly but few address openly: when does investing stop being investing—and start behaving like gambling?

Eric is the Head of Corporate Development at Viant Technology, with experience spanning investment banking, capital markets, M&A, and corporate finance. He has deep familiarity with traditional investing, day trading, crypto, NFTs, and speculative assets—and like Alyx, he reentered the sports card hobby in early 2020, right as markets, collectibles, and risk-taking behaviors collided at full speed.

Together, Alyx and Eric explore how the last 5–6 years reshaped our relationship with risk. From commission-fr ...