Investor Stories 470: Passing on Uber, Perplexity, and Fintech's Breakout Winners — The Stories Behind the Misses (Orthlieb, Callaghan, Byunn)
From The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified by Nick Moran
April 9, 2026 · 6 min
About this episode
Investors share stories of missed investment opportunities and the reasons behind their decisions.
On this special segment of The Full Ratchet, the following Investors are featured: Ben Orthlieb of Blue Moon Jon Callaghan of True Ventures Eric Byunn of Centana Growth Each investor highlights a situation where they decided not to invest, why they passed, and how it played out. The host of The Full Ratchet is Nick Moran of New Stack Ventures , a venture capital firm committed to investing in founders outside of the Bay Area. We're proud to partner with Ramp , the modern finance automation platform. Book a demo and get $150—no strings attached . Want to keep up to date with The Full Ratchet? Follow us on social . You can learn more about New Stack Ventures by visiting our LinkedIn and Twitter .
People in this episode
Host: Nick Moran
Guests: Ben Orthlieb, Jon Callaghan, Eric Byunn
Topics covered
- venture capital
- startup investing
- investment decisions
- missed opportunities
- fintech
Keywords
- Uber
- Perplexity
- fintech
- investment stories
- venture capital
Sponsors
Ramp
Mentioned in this episode
Organizations: Blue Moon, True Ventures, Centana Growth, New Stack Ventures
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