The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified Investor Stories 444. The Biggest Misses in VC: Passing on Airbnb, Overlooking Skype, and Arriving Hours After Postman Closed (Maples, Okike, Mohapatra)
Dec 4, 2025
This segment features Mike Maples Jr., a venture capitalist known for his early-stage investments, who reflects on his decision to pass on Airbnb in 2008 and the valuable lessons learned. Nnamdi Okike, partner at 645 Ventures, reveals how founder concerns led him to overlook Skype early on, impacting his investment trajectory. Hemant Mohapatra from Lightspeed India shares his regret about missing out on Postman due to a delayed decision, emphasizing the importance of acting swiftly when conviction strikes. A compelling discussion on lessons learned in venture capital!
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Missing Airbnb In 2008
- Mike Maples, Jr. passed on Airbed and Breakfast (Airbnb) in 2008 after a confused meeting and product issues.
- He later reflected on that miss in his book Pattern Breakers and redeemed with a Lyft investment.
First Impressions Skew Big Bets
- Early product demos can make or break first impressions for investors, even if the idea later proves massive.
- Reflecting on misses helps investors recalibrate pattern recognition and investment instincts.
Passing On Early Skype
- Nnamdi Okike passed on Skype early due to the founders' prior legal baggage from Kazaa and timing misfit with his firm.
- The company later exited for $2.5 billion, which he recalls as a costly class from business school.
