068 RRE Ventures: James Robinson on Investing in Sports

James Robinson from RRE Ventures joins the podcast to break down what investors are actually looking for in sports tech right now.We get into his path from the Boston Bruins and Octagon into venture, and how that operator perspective shapes how he evaluates companies today.RRE has been around for over 30 years and is one of the more established early-stage firms in the market, with over $2.5B in assets under management, 400+ portfolio companies, and 125+ exits. James shares why most founders get it wrong when pitching, the difference between solving a real pain point vs. building something “nice to have,” and how to stand out when reaching out to investors.We also talk about where sports is heading in 2026, from identity and payments to venue intelligence, and why the biggest opportunities aren’t in fan-facing products, but in the infrastructure powering the entire ecosystem.If you’re building in sports or thinking about raising capital, this is a practical conversation on what actually matters.