Gabe Stengel - Building Investing Superintelligence
September 22, 2026
AI Summary
5 min readGabe Stengel, founder and CEO of Rogo, spent the early years of his company building a product that didn't work. The models weren't capable enough. But he was betting on a trajectory: that the raw intelligence of frontier models would eventually catch up to the vision of an AI analyst for Wall Street. When OpenAI's o1-pro and then Anthropic's Opus 4.5 arrived, they did. Rogo went from a clunky demo to a tool that investment bankers and dealmakers describe as "transforming the way I work." The lesson Stengel draws is that if you were right about the end state and built toward it, when the models get there, the product becomes magical. The hard part is surviving the gap.
The Core Insight: Private Markets Are a Plumbing Problem
Stengel’s central strategic bet is that the biggest opportunity in financial AI is not in public equities, where data is standardized and much of the workflow is already automated. It is in private markets—mergers, acquisitions, fundraising, and deal execution—where coordination is still done by humans, data is unstructured, and the "plumbing" of compliance, audit trails, and data rooms is fragmented and manual.
Continue reading the full summary in the app — free to try.
Read Full Summary →Free • No credit card required
Never miss an episode of Invest Like the Best with Patrick O'Shaughnessy
Get every new episode summarized in your inbox — free, ~5 minutes to read.
No spam. Unsubscribe anytime.
What you'll learn
- 1 (00:00) **Sponsor Break - Ramp, Work OS**
- 2 (01:12) **The Trajectory of Investing Superintelligence** - Gabe Stengel describes the arc from early failures to today’s functional product.
- 3 (05:35) **Designing for the Wall Street Workflow** - Details on the specific UX decisions that drive adoption in banking.
- 4 (07:33) **The Real-World Use Case: Deal Makers** - A breakdown of who uses Rogo and for what primary purpose.
- 5 (09:48) **Why Private Markets Over Public Equities** - Explaining the strategic choice of market focus.
- 6 (12:17) **Skills That Will (and Won’t) Matter for Investors** - A direct take on the future of the investment professional.
- 7 (15:03) **The Rogo Assembly Line: Data, Models, and Harness** - How the system architecture has evolved from a Rube Goldberg machine to a streamlined system.
+ Full timestamped outline available in the app
Show Notes
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, Cu
More from this podcast
Invest Like the Best with Patrick O'Shaughnessy →