Connor Ryan, Partner at Bridge Venture Fund, shares his insights on investing in overlooked markets and the importance of sustainable unit economics. He explains why he prioritizes revenue quality over aggressive growth, the difference between projected and demonstrated product-market fit, and how Bridge Venture Fund supports startups tackling inefficiencies in industries like legal tech and sports sponsorship analytics. Connor also discusses the asymmetric risks in venture capital and how VCs can better support founders, even when things don’t go as planned.

In this episode, you’ll learn:
[02:27] From private equity to venture capital—Connor’s unconventional path and why he invests in overlooked industries

[07:06] How Bridge Venture Fund identifies overlooked industries ripe for innovation

[12:28] The two key questions Connor asks in every pitch meeting

[16:52] How legal tech startups like CaseText are transforming traditional workflows

[17:32] Why non-lead VCs like Bridge Venture Fund have to move fast but still maintain rigorous diligence

[22:38] The most common reason Connor passes on startups: weak unit economics and misleading LTV/CAC assumptions

[27:49] Connor’s perspective on venture capital’s asymmetric risk and why founders bear the brunt of failure

The non-profit organization that Connor is passionate about: World Wildlife Fund

About Connor Ryan

Connor Ryan is a Partner at Bridge Venture Fund, where he focuses on investing in startups serving overlooked and underserved industries. Before joining Bridge, he worked in private equity and investment banking, gaining deep insights into business model sustainability and market inefficiencies. Connor holds an MBA from Northwestern University’s Kellogg School of Management and is passionate about supporting founders who bring real innovation to lagging industries.

About Bridge Venture Fund

Bridge Venture Fund is a Chicago-based early-stage VC firm investing in startups that serve industries underserved by innovation. With a focus on sustainable unit economics and market-defining solutions, the firm has backed companies in legal tech, sports sponsorship analytics, retail, and more. Notable investments include CaseText (acquired by Thomson Reuters) and Trajektory.

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