E301: Why Generating Alpha is So Hard

After 300 interviews with the world’s top investors, what does alpha actually look like and why is it almost never what people think it is? In this special episode, the roles are reversed. David Weisburd, host of How I Invest and Co-Founder of Weisburd Capital, steps into the guest seat as his co-founder Curtis Pierce takes over as host. Together, they unpack the most important lessons David has learned from more than 300 conversations with CIOs, LPs, GPs, founders, and allocators representing trillions in assets. The discussion centers on why real alpha is hard, boring, and often low-status, how structural advantages drive sustainable outperformance, and why governance and portfolio construction matter more than any single trade.