Fintech Storytelling, Building Credit & Credibility with Andrew Endicott, Gilgamesh Ventures

We sat down with Andrew Endicott, GP at Gilgamesh Ventures and former co-founder and president of Petal—one of the earliest fintech companies to challenge traditional credit underwriting by using cash-flow data instead of credit scores.It’s one of those conversations that looks like a fintech episode on the surface, but ends up being something deeper: a discussion about how people make decisions inside complex systems, how founders earn trust over time, and why Latin America continues to produce some of the most compelling fintech businesses in the world.Andrew brings a rare mix of perspectives to the table. He’s a lawyer by training, a founder who built inside U.S. financial regulation, and now an investor who’s spent years developing pattern recognition across the U.S. and Latin America. He’s thoughtful without being academic, opinionated without being dogmatic—and refreshingly honest about what he doesn’t know.We talk about fintech complexity, regulatory tradeoffs, the capital cycle behind lending businesses, storytelling as companies scale, and the “light-bulb moment” that led to Gilgamesh’s LatAm thesis. We also wander into employee compensation, investor psychology, and why spending time away from screens might be one of the most underrated founder skills.If you’re a founder building in fintech—or an investor trying to understand why some teams win and others stall—this episode is pure gold.