Gabe Stengel is the co-founder and CEO of Rogo, the AI platform for finance. He believes the best investors will spend the next several years reinventing their firms around AI, and Rogo is trying to build the infrastructure that allows them to do it. We discuss how Rogo evolved alongside the frontier models, why the last mile and the harness around the models matter so much, what happens when every portfolio manager can deploy thousands of agents against a problem, and how AI could transform the way capital is raised, assets are priced, and deals get done. We also cover which investing skills become more valuable as AI improves, the move from seat-based to outcome-based pricing, Rogo’s internal company brain called Shrek, the 40 investor rejections Gabe received before his Series A, why building in applied AI requires extraordinary aggression, and what it takes to become a black hole for talent and capital. Please enjoy my conversation with Gabe Stengel. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at colossus.com/subscribe. ----- Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to ramp.com/invest to sign up for free and get a $250 welcome bonus. ----- Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to vanta.com/invest. ----- WorkOS is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Visit ridgeline.ai. ----- Editing and post-production work for this episode was provided by The Podcast Consultant. Timestamps: (00:00:00) Welcome to Invest Like The Best (00:01:24) The Model Eras of Rogo (00:04:15) Why the Last Mile Mattered (00:06:14) Who’s Using Rogo Right Now (00:10:55) Which Investor Skills Still Matter (00:12:23) Inside Rogo's Data Stack (00:14:33) Competing With the Frontier Labs (00:16:57) Why the Harness Matters Most (00:18:05) What Makes a Vertical AI Winner (00:22:00) How Firms Buy AI Software (00:23:43) From Seats to Outcome Pricing (00:31:19) Auditability Beats Accuracy (00:32:55) Scaling Enterprise Sales Fast (00:34:48) Meet Shrek, Rogo's Company Brain (00:35:49) The Pitch to Great Talent (00:39:37) What Chewing Glass Feels Like (00:42:18) Forty Investor Rejections (00:47:41) Finance's Innovator's Dilemma (00:50:22) Questions Every Firm Should Ask (00:53:09) What Remains Most Uncertain (00:56:46) Becoming a Black Hole for Talent (00:57:56) The Kindest Thing
