Key Takeaways
- Gary Vee is not afraid to "go backwards" and is willing to bet big when he sees major opportunities, like his early investments in Facebook, Tumblr, and Twitter
- Gary believes attention is the most valuable and "mispriced" asset, and he is constantly analyzing platforms, culture, and how to best capture and leverage attention
- Gary has a "safety net" of $1 million, but is willing to bet the rest of his wealth on big opportunities he believes in strongly
- Gary is inspired more by people facing major adversity and hardship with resilience and grit, rather than by famous entrepreneurs and billionaires
- Gary sees a lot of potential in emerging technologies like AI-generated audio/podcasts and believes language translation will be a huge growth driver for platforms in the future
Introduction
In this episode, Sam Parr and Shaan Puri sit down with Gary Vaynerchuk to discuss a wide range of topics, from Gary's early investments that paid off big, to his mindset around risk-taking and going "backwards", to who inspires him most. The conversation provides a fascinating glimpse into Gary's thought processes, his views on the future of technology and attention, and the psychology of successful entrepreneurs.
Topics Discussed
Gary's High School Report Card & Turnaround (1:31)
- Gary openly shares his poor high school grades, including failing German all four years and getting a D in speech class
- He attributes this to not doing any homework and being more focused on working in his family's liquor store and selling baseball cards
- Gary believes if he was growing up today, his teachers may have been more encouraging about his entrepreneurial instincts rather than labeling him a "loser" or "garbage man"
Emerging Technologies & Attention (5:31)
- Gary is excited about an app called "Break the Web" that provides a real-time feed of trending topics and cultural moments
- He sees attention as the most valuable and "mispriced" asset, and is constantly analyzing platforms, culture, and how to best capture and leverage attention
- Gary believes language translation will be a huge growth driver for platforms in the future, citing Facebook's early success after localizing to different languages
Adult Camps vs. Conferences (16:23)
- Sam and Shaan describe their "My First Million" adult summer camp, where they rent a house and bring in trainers to put attendees through NBA-style workouts
- The goal is to create a fun, competitive environment that avoids the typical "networking" and "conference" vibe
- Gary is intrigued by the concept and shares his own love of losing the first game in pickup basketball to get himself fired up to win the next one
Millionaires vs. Billionaires (20:06)
- Gary believes the key difference between someone with a $10M business vs. a $100M+ net worth is often risk tolerance and fear of "going backwards"
- He is somewhat romanticized by the idea of being okay with it all "falling down" and having to rebuild from nothing
- Gary sees a lot of serendipity and luck involved in business success, and wonders how his path may have been different if his family owned a supermarket instead of a liquor store
Gary's Investment Portfolio & Safety Net (28:43)
- Gary keeps a $1 million "safety net", but is willing to bet the rest of his wealth on big opportunities he believes in strongly
- He is not afraid to go "all in" on investments he feels passionately about, similar to his early Facebook investment
- Gary sees this willingness to take big risks as a key driver of his success, though he acknowledges it's not a strategy for everyone
Gratitude & Mindset (31:41)
- Gary and the hosts discuss the importance of gratitude, with Gary emphasizing the value of "micro" gratitude in everyday moments vs. just being grateful in a "macro" sense
- Gary sees his own mindset as being very open to "winning and losing" and not getting too attached to his professional success or identity
- He is inspired more by people facing major adversity with resilience and grit, rather than famous entrepreneurs and billionaires
Gary's Best Investment (37:45)
- Gary's best investment by far has been his Facebook stock, which he has never sold a single share of since investing in the company's Series B round
- He attributes this success to his focus on investing in the person (Mark Zuckerberg) rather than just the idea or business
Perspectives on Zuckerberg, Logan Paul (39:08)
- Gary believes Zuckerberg is "uncomfortably underrated" and had an incredible understanding of attention as a key asset
- On Logan Paul, Gary sees him as a natural entertainer and performer who will likely continue to evolve and cross over into mainstream success, similar to The Rock or Will Smith
Who Inspires Gary (45:44)
- Gary is more inspired by people facing major adversity with resilience and accountability, rather than famous entrepreneurs
- He admires the "bodega owner energy" of people who are just trying to provide for their families and live a good life, rather than seeking fame and attention
Conclusion
This conversation with Gary Vaynerchuk provides a unique window into the mindset and decision-making of a highly successful serial entrepreneur. Key takeaways include Gary's willingness to take big risks on opportunities he believes in strongly, his fascination with attention and emerging technologies, and his admiration for people facing adversity with grit and resilience.
Throughout the discussion, Gary shares insights on his own unconventional path to success, the role of luck and serendipity in business, and the importance of gratitude and maintaining the right perspective. His passion for entrepreneurship and his ability to see the world through a distinct lens make him a compelling and thought-provoking figure in the startup and tech community.