Host John Watters sits down with longtime friend Jay Leek, Managing Partner of SYN Ventures, to trace his path from building computers in his family's business in West Texas to operating roles at Nokia, Equifax, and Blackstone, where he became the first CISO in private equity. Jay explains how those experiences shaped his move into full time investing, and shares how he evaluates founding teams, why timing now carries as much weight as team and technology, and how AI is reshaping the attack surface and the role of the engineer. Takeaways: Evaluate teams first. Jay's four Ts framework, team, total addressable market, technology, and timing, puts team ahead of everything else, since a strong team will find a way around obstacles instead of giving up.Expect a stumble. Every company Jay has invested in has faced a setback at some point, and how a team recovers matters far more than avoiding the setback altogether.Separate testing from production. Jay's longstanding rule for portfolio companies is to never confuse a production environment with a glorified QA environment, a lesson that applies well beyond startups.Watch how teams adapt to AI first development. The role of the engineer is shifting from writing code to managing outcomes, and founders who can embrace that shift are better positioned for what comes next.Treat timing as its own discipline. Markets and technology are moving fast enough that timing now deserves the same weight as team, market, and technology when assessing an opportunity.Build from operating experience. SYN Ventures was built around partners with decades of firsthand experience as CISOs, CEOs, and founders, which shapes how they support the companies they back.Take calculated risks early. Jay reflects that developing comfort with risk earlier in a career, and recovering quickly from missteps, can meaningfully accelerate long term growth.Quote of the Show: “A smart team will jump over it, break it down, crawl around it, run around it, do whatever they need to do.” - Jay LeekLinks: LinkedIn: linkedin.com/in/jayleekWebsite: synventures.comWays to Tune In: Podcast Website: https://wattersedgepodcast.com/ Spotify: https://open.spotify.com/show/033ZejaonpOuVPFh8m350w Apple Podcasts: https://podcasts.apple.com/podcast/watters-edge-1e65430c-e5c4-4c35-a520-bf0d90571f3b/id6796840936 Amazon Music: https://music.amazon.com/podcasts/4b3bebed-655d-42a7-82de-021519c4ccea iHeart Radio: https://iheart.com/podcast/340198973/ YouTube: https://www.youtube.com/@WattersEdgePodcast
