Dan Teran and James Gettinger joined Risk Reversal to talk about Gutter Capital's $75M Fund III and the second cohort of Elbow Grease. They trace Gutter's roots back to the 110+ angel investments they made and explain why the firm has stayed deliberately concentrated, rather than chasing scale. Dan shares what he learned building and selling Managed by Q to WeWork, and James talks through a decade he spent as a professional gambler and how that shaped a more quantitative approach to investing. The two make the case that venture has grown consensus-driven with rising seed prices andcapital piling into a handful of mega-funds, which has made it harder for non-traditional founders to raise. It's a clear look at why Gutter bets early and started its Elbow Grease accelerator to work hands-on with committed early-stage founders that don't fit the typical VC mold.