Garnet Heraman brings three decades of experience as a founder, operator, and venture investor to a conversation that cuts through the noise of the startup and VC world.A 3× exited entrepreneur who built his career from a scholarship kid in New York to co-founding Aperture VC — one of the largest fintech funds led by diverse managers — Garnet shares what actually drives venture outcomes, what most founders misunderstand about fundraising, and why timing is often more important than the idea itself.We get into his framework for backing companies, including the rare “contrarian technocrat” profile, how great teams balance vision with execution, and what separates founders who can truly sell a market opportunity from those who can’t. He also explains how venture capital is becoming a barbell business, why most funds can’t compete in the LLM race, and where smaller, faster players can win in the AI era — particularly in vertical, highly regulated industries.The conversation moves beyond theory into real pattern recognition: spotting Uber-like ideas too early, betting on founders before the data exists, and knowing when not to take venture money at all.If you’re building in sports, fintech, or any emerging tech category, this episode is a masterclass in how investors think, how cycles actually work, and how to position your company for the next 3–5 years.

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“What did the council decide on item 42?” — answered with the speaker and the moment.

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