From tutoring math as a UBC engineering student to scaling a real estate portfolio from $5M to $60M, Jesse Peng (Class of 2011) has built his career at the intersection of technology, strategy, and bold decision-making.

In this episode, Jesse opens up about the failed startups that shaped him, the pressure to live up to expectations, and the mindset shifts that helped him move across industries. His journey spans digital marketing, real estate investing and now collectible technology. As a pioneer in the trading card and collectibles space, he’s focused on disrupting a multi-billion-dollar industry through transparency, passion, and community impact.

We talk about risk, resilience, “winner’s tilt,” and why poker might be the ultimate training ground for entrepreneurship. Most of all, Jesse shares why building something meaningful — not just profitable — is the real measure of success.