Roger Ehrenberg ran DB Advisors, Deutsche Bank’s $6 billion multi-manager hedge fund platform, overseeing around 20 trading teams across statistical arbitrage, high-frequency trading, CTA, and special situations. He went on to found IA Ventures and now runs Game Changers Ventures. In this episode of Odds on Open, Ethan Kho and Roger get into how risk was allocated across pods before the Millennium and Citadel era, and why correlations go to one in a crisis. They also cover the LTCM lesson on time-horizon diversification and how to size positions when semiconductor volatility is running far above historical norms. They debate whether small, nimble managers or scaled multi-manager platforms capture the alpha from AI, and why the best small funds look like high-Sharpe volatility market makers that can’t scale.The second half moves into venture capital through the lens of a former hedge fund risk manager. Topics include Cliff Asness’s “volatility laundering” critique, right to win in a market where VC money is all chasing AI momentum, slugging percentage versus hit rate, portfolio concentration with 25 shots on goal, follow-on and pro rata discipline, and when to sell secondaries. Roger explains where venture process errors come from and the founder pattern behind his biggest winners. He also makes the contrarian case for investing outside the crowded AI infrastructure trade, compares today’s interconnected AI capex to 2007–08 rather than the dot-com bubble, and gives career advice for students and junior analysts whose skills are being commoditized by AI. If you care about hedge funds, quant trading, portfolio construction, risk management, or early-stage investing, this one is for you.