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Out of Office: Gary Vaynerchuk on Entrepreneurship, “Street Smarts”, & the Future of Tech

Last Updated: April 26, 2023

Gary Vaynerchuk, the digital media visionary, angel investor, and CEO of VaynerMedia, talks to Rich and Gianni about why he often values street smarts over Ivy League degrees in business, the perils of lacking self-awareness, the key lessons he learned as a teen working in his family’s wine business, and the technology he’s confident will revolutionize the consumer experience. He also discusses his early days in tech, including networking at SXSW and the rise of Tumblr, Twitter, and Facebook, and how athletes and entertainers have contributed to it being “cool” to be a businessman.