The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified Investor Stories 470: Passing on Uber, Perplexity, and Fintech's Breakout Winners — The Stories Behind the Misses (Orthlieb, Callaghan, Byunn)
Apr 9, 2026
Jon Callaghan, longtime VC at True Ventures, recalls passing on Uber at seed for lack of a clear CEO. Ben Orthlieb, early-stage investor at Blue Moon, shares a disciplined pass on Perplexity during an aggressive raise. They trade candid stories about leadership, price discipline, timing, and how execution can overturn initial doubts.
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Passing On Perplexity Over Price And Time
- Ben Orthlieb passed on investing in Perplexity during their $90M raise because of price discipline concerns.
- He also lacked time to evaluate founder personality and questioned whether early LLMs were commoditized, making it a defensive pass.
Protagonist Over Product For VC Conviction
- A founder acting as a committed protagonist matters more than an early promising product for some VCs.
- Callaghan notes his firm's requirement for a leader drove the pass even when the product and early signals were strong.
Passing On Early Uber For Lack Of A Leader
- Jon Callaghan passed on Uber at seed because there was no clear CEO or protagonist at the time.
- He had used the product and knew Garrett but the founders treated it like a project not a company until Travis became CEO later.