second-time-founder
(6)
Apurv Bansal Took the Long Way Back to Building
He sold a startup, went to Harvard, joined Google, became a venture capitalist, and still felt pulled toward the founder’s chair. Zenskar is what happened when Apurv Bansal finally stopped circling and chose a problem built for a long game.
Deepti Yenireddy Is Teaching AI to Read the Physical World
From oil-field instruments to construction drawings, the Boon founder has spent two decades turning stubborn, real-world data into software people can inspect, correct and trust.
Matt Watson
Matt Watson is the co-founder and CEO of Origin, a Boston-based fintech that in September 2025 launched what it calls the first SEC-regulated AI financial advisor. A former Citigroup high-yield credit trader who previously co-founded Indio Technologies (acquired by Applied Systems in 2019), Watson has raised more than $75 million for Origin from Founders Fund, Felicis, General Catalyst and 01A to make certified-financial-planner-quality advice available to people who normally can't afford it.
Catherine Jiang
Catherine Jiang is the founder and CEO of Dill, a Y Combinator-backed (W23) software company that helps construction suppliers automate accounts receivable, online payments, credit applications, and lien rights management to get paid faster. A second-time founder, she previously co-founded SiteTrace (acquired by BuildCentrix) and was a product manager at Yelp. She holds a B.S. in Symbolic Systems from Stanford. Dill launched in 2023 serving foodservice distributors and later refocused on the construction supply chain, where late payments and paper-based invoicing choke cash flow.
Othman Ouenes
Othman Ouenes is the CEO and co-founder of Fidari, an oncology-first care infrastructure company whose name means 'in my home' in Arabic. A second-time healthcare founder, he previously co-founded QURE Healthcare (acquired by TRC Healthcare), where he spent roughly twelve years building clinical-measurement software. Born in France to a Moroccan mother and French-Algerian father and raised in the United States, he studied Human Biology at Stanford and now lives in Santa Fe, New Mexico, where he also serves as a part-time firefighter. Fidari combines AI-driven workflow automation with human navigation to help health systems coordinate supportive cancer care, capture billing, and connect patients to home-based services.
Tom Petit
Tom Petit is the co-founder and CEO of Didero, a New York company building an agentic AI procurement platform that sits on top of a manufacturer's existing systems and quietly does the routine work of running a supply chain. A Belgian who came of age in Texas, he trained in computational mathematics at Stanford and Cambridge, did data science at Airbnb and HelloFresh, and co-founded the real-estate fintech Landis before turning to the unglamorous world of purchase orders and supplier emails. In February 2026 Didero raised a $30M Series A co-led by Chemistry and Headline, with Microsoft's M12 participating, bringing total funding to roughly $37M.