Investors Reflect on Missed Opportunities with Uber
- Gary Vaynerchuk expressed regret over not investing in Uber during its early stages, recognizing that he could have made millions.
- He passed up the opportunity to invest in the ridesharing giant not once, but twice.
- Vaynerchuk's reflections highlight the challenges of making investment decisions in the fast-evolving tech landscape.
In a recent LinkedIn post, Gary Vaynerchuk, CEO of Vaynerchuk Media, expressed regret over not investing in Uber, a company now valued at approximately $138 billion. Vaynerchuk described this decision as "one of the greatest mistakes of my investing career." Back in 2009, Uber's co-founders sought funding at a mere $10 million valuation, and had Vaynerchuk invested $25,000, his stake would now be worth around $345.1 million. Despite his friendship with Uber's founders, Travis Kalanick and Garrett Camp, Vaynerchuk initially declined to participate in the angel investment round due to doubts about the company's direction. However, after testing the app in 2011, he recognized Uber's true value proposition: it wasn't just about transportation, but about saving time for users. He noted that the app significantly reduced the friction involved in hailing a cab, emphasizing that people prioritize time above all else. Vaynerchuk is not alone in his regret. Mark Cuban, another prominent investor, also turned down an opportunity to fund Uber at the same $10 million valuation. Although he had previously invested $1.7 million in Kalanick's earlier venture, Red Swoosh, Cuban sought to invest at a much higher valuation of $5 billion, which Kalanick did not accept. Cuban lamented that a $250,000 investment at the lower valuation could have yielded billions today.