Gary Vaynerchuk, co-founder of Resy and CEO of Vaynerchuk Media, recently shared his regret about not investing in Uber during its early stages, a decision he considers one of his biggest investment mistakes.

In a LinkedIn post last week, Vaynerchuk lamented passing on two opportunities to invest in Uber’s angel round when the company was valued at just $10 million. Today, Uber boasts a market capitalization of approximately $138 billion, making it one of the most valuable tech companies globally.

Despite being acquainted with Uber’s co-founders, Travis Kalanick and Garrett Camp, Vaynerchuk opted out of investing initially due to doubts about the company’s direction. Reflecting on his decision, he admitted to CNBC Make It in 2019 that he was skeptical because Kalanick and Camp were juggling full-time jobs while building Uber, a scenario reminiscent of Vaynerchuk’s own failed side hustles.

However, Vaynerchuk reconsidered his stance two years later after experiencing Uber firsthand when his brother AJ took the first Uber ride in New York City in 2011. This moment marked a realization for Vaynerchuk: Uber wasn’t just providing transportation but selling convenience and time-saving solutions in a mobile era.

“Uber sells us time,” Vaynerchuk emphasized in his LinkedIn post. By allowing users to summon rides via mobile phones, Uber effectively reduces the friction associated with traditional taxi services, aligning with modern consumer demands where time is paramount.

Vaynerchuk’s missed opportunity to invest in Uber echoes similar regrets from other notable investors, including Mark Cuban, who also declined to invest at Uber’s $10 million valuation despite recognizing its disruptive potential in the transportation industry.

Investment decisions like these underscore the challenges and uncertainties inherent in early-stage investing, where foresight and timing play critical roles in realizing substantial returns. As Vaynerchuk reflects on his experience with Uber, it serves as a reminder of the volatile nature of investment opportunities and the importance of conviction in seizing them when they arise.