E215: The Pursuit of Uncorrelated Returns in Venture Capital w/Dan Kimerling

Can venture capital be reinvented to deliver alpha without relying on “heroic assumptions”? In this episode, I go deep with Daniel Kimerling, Founder and Managing Partner of Deciens Capital, on his mission to build a different kind of venture fund—one focused on highly concentrated, long-duration bets in financial services. Dan explains why Deciens is unapologetically “get rich or die trying,” how his team avoids the venture hamster wheel of markups and momentum rounds, and why he believes the next generation of financial institutions (not just fintech apps) will be the true power-law winners. We cover his philosophy on portfolio construction, long timelines, liquidity vs. exits, and how Deciens publishes its playbooks openly to challenge orthodoxy. Highlights: Why Deciens aims to be an uncorrelated alpha stream within venture capital Radical transparency: aligning with LPs upfront on asymmetric return expectations Portfolio construction based on computational simulations; choosing concentration over diversification Targeting 10–15 companies per fund, with a model designed to deliver 5x net returns The case for financial services as venture’s overlooked mega-sector (20% of global GDP) Examples from the portfolio: Chipper Cash, Treasury Prime, Tint Insurance, Sidecar, SimplyWise, Generous Energy The “venture hamster wheel” of markups and why Deciens rejects it Why liquidity and exits aren’t the same—and why dividends can be just as powerful 14-year fund timelines aligned with LPs like pensions and sovereigns that can go long duration Deciens as a movement: defying orthodoxy, building with aligned entrepreneurs, and embracing authenticity Guest Bio: Daniel Kimerling is the Founder and Managing Partner of Deciens Capital, a first-principles venture firm backed by sovereign wealth funds, endowments, and pensions. Deciens is known for its concentrated focus on financial services—backing both fintechs (like Chipper Cash and Treasury Prime) and next-generation financial institutions (from insurance to asset management). Prior to founding Deciens, Dan co-founded Standard Treasury (acquired by Silicon Valley Bank) and served as GM of API Banking at SVB. A published writer and frequent speaker, he is recognized for challenging conventional VC orthodoxy through essays like Defying Orthodoxy and Betting on Convexity. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . #VentureCapital #VC #Startups #OpenLP #AssetManagement Stay Connected: X / Twitter: David Weisburd: @dweisburd LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Daniel Kimelring: https://www.linkedin.com/in/dkimerling/ Links: Deciens Capital: https://deciens.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . (0:00) Preview (0:52) Deciens's Capital's investment strategy and portfolio examples (3:00) Deciens's uncorrelated venture strategy and high-risk, high-reward philosophy (5:24) Managing LP expectations with transparency and communication (7:00) Nontraditional portfolio construction and computational simulations (9:45) Process of constructing a portfolio and the conservative approach (14:13) The potential of financial services companies and ecosystem background (20:01) Liquidity strategies and exit planning for non-traditional investments (22:49) Aligning strategy with LPs and venture return competition (26:28) Small fund size counterarguments and the importance of investment asymmetry (29:24) Long-duration investment timelines and compound growth (33:34) Structural alpha advantages and venture fund strategies (38:23) Learnings from closing Fund three and viewing Deciens as a movement (42:04) Pitfalls of traditional venture capital models (46:01) Advice to a younger self on the importance of differentiation (51:28) Creating durable alpha and structural advantages (55:11) The impact of the need for validation on investment decisions (59:21) Aligning firm success with charitable goals and personal motivation (1:01:22) Closing remarks