

The Boardroom: Out of Office | Interview with Rich Kleiman
Nov 27, 2020
In this engaging conversation, Gary Vaynerchuk, a dynamic entrepreneur known for VaynerMedia, joins Rich Kleiman, an entrepreneur and podcast host, to discuss the power of street smarts versus formal education. They dive into self-awareness as a crucial element for success in business, share key lessons from Gary's early days in the family wine business, and explore how technology is set to transform consumer experiences. The duo also reflects on aging, the journey of entrepreneurship, and the importance of personal accountability in leadership.
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GaryVee's Origin Story
- Gary Vaynerchuk's journey included growing his family's wine business from $4M to $60M using early internet marketing.
- He then transitioned to angel investing, funding companies like Twitter, Tumblr, and Facebook, changing his trajectory.
Conviction in Early Investments
- Gary Vaynerchuk's success with angel investing wasn't a whim but a result of years of internet marketing experience and conviction.
- He saw the potential of platforms like Tumblr and Facebook early on, investing heavily based on his observations.
Street Smarts vs. Ivy League
- Value street smarts and resilience over academic pedigree when evaluating entrepreneurs.
- Formal education doesn't always prepare founders for real-world business challenges like handling setbacks.