Podcast Summary

In Search Of Excellence

Host: Randall Kaplan
Guest: Gary Vaynerchuk (“Gary Vee”)
Episode: $2 Billion Dollar Taco, Live Shopping, and Customer Service | E171
Date: August 16, 2025

Episode Overview

In this episode, Randall Kaplan has a candid, wide-ranging conversation with serial entrepreneur, investor, and branding expert Gary Vaynerchuk (Gary Vee). They dig into Gary’s journey from the family liquor store to angel investing in transformative startups (Twitter, Facebook), why he believes live shopping is the next American retail juggernaut, lessons in customer service, investing, preparation, work ethic, and his ultimate aim to buy the New York Jets. It's a masterclass in entrepreneurial thinking and leadership, loaded with stories, actionable insights, and no-nonsense Gary Vee advice.

Key Discussion Points and Insights

1. Early Angel Investments & the Twitter/Facebook Backstory

• Gary recounts his early video advocating for Twitter, which led to his first investment opportunity.
• Blaine Cook, Twitter’s first CTO, offered Gary, Fred Wilson, and Kevin Rose the chance to buy his Twitter shares after deciding to leave the company.
• Gary's advice to Cook:

  “I tried to talk him out of it. I said, I think you’re making a huge mistake. ...I could see he was making an emotional decision.” (00:04)

• The missed value: Cook left “$702 billion on the table.” (00:31)
• Dinner with Mark Zuckerberg after speaking at Facebook led to another pivotal moment:

  “Sister Randy called me...Would you like to buy some Facebook equity? I literally took 80% of my savings and invested in Facebook.” (00:50, 22:11)

2. Spotting Trends & First Mover Advantage

• Gary’s superpower is identifying “where the attention is” and moving faster than legacy competitors.
• He compares the rise of email and website-based selling in wine (late 90s) to his current conviction in live social shopping:

  “If you ask me right now, out of all the optionality in the world… live shopping is at the tippy top of my list.” (02:15) “I view these trends like poker and I view live shopping...like having the nuts in poker... You go all in because you’ve won.” (03:32)

• He asserts that current American brands underestimate the tidal wave coming via platforms like TikTok Shop, Whatnot, and soon Meta.

3. Culture & Customer Service: The Legend of the Snowstorm Wine Delivery

• A key leadership lesson: create company culture through direct actions, not just storytelling or posters.
• Story: On the busiest holiday, Gary personally delivered a case of wine to an elderly customer in a snowstorm, sacrificing thousands in sales that hour to make a lasting point about customer service.

  “Don’t make a fucking poster and put it in the hallway...do an action.” (05:08) “I might have lost $20,000 in sales that hour, but I’ve helped my dad make millions since.” (09:01)

• This became internal myth and a foundational example for his team.

4. The Origin of VaynerMedia & Scaling Through Opportunity

• Consulting gig at ESPN after amassing a Twitter following opened his eyes to enterprise ignorance about social media:

  “I couldn’t believe the biggest companies in the world didn’t understand social media.” (12:10)

• Out of necessity and opportunity (“had no money”), he and his brother AJ set up a consultancy, later VaynerMedia.
• Early collaborative work (such as giving a quote for Buddy Media) landed him seven figures after its sale to Salesforce.
• VaynerMedia flourished, “now a $350 million a year revenue business with 2,000+ employees.” (14:16)

5. Angel Investing Philosophy

• Gary’s progression as an investor:

  “Early on, I went for the horse. Then I went for the jockey. Now it requires both...the operator and the idea.” (23:03)

• Most pitches come via network, not cold outreach. He prefers dialog and gut feel over elaborate decks:

  “I don’t even consume decks. My team knows this... What really gets me is if somebody says something that I believe in that I can follow up with a couple of questions and they can answer it.” (24:35)

• Contrasts with Kaplan's focus on extreme preparation and impressive presentation materials. Both agree on the importance of substance over show.

6. The Science and Art of Attention in Marketing

• Insights from Gary’s books “Jab, Jab, Jab, Right Hook” and the latest, “Day Trading Attention.”
• Believes the best social media post can outperform all but the Super Bowl in terms of impact:

  “The best social media organic post...is a more important form of advertising than any television commercial...outside of Super Bowl.” (27:34)

• Super Bowl remains the absolute king for pure attention, if creative is strong:

  “The creative is always going to be the variable of success.” (29:05)

7. Foundations of Success: Work Ethic, Passion, and Preparation

• On choosing work ethic, talent or passion:

  “Yes. Of the three, work ethic is controllable and it’s something that I get scared that people try to downplay.” (29:22)

• Warns against using “wellness” as an excuse for inaction:

  “I am worried people are using health and wellness and mental health...as weapons to create entitlement or laziness.” (30:50)

• Preparation:

  “What baffles all my top executives...is I go into meetings cold and dominate them. They think I do no prep...It’s the only thing I do. The reason I can walk into any brand and crush a meeting is because most business is not that complicated.” (31:48) “The ultimate preparation is to actually be a practitioner.” (33:51)

8. Goals, Money, and Personal Motivation

• Chasing the New York Jets has been a lifelong ambition, but adaptability is crucial:

  “The chase of it is the great enjoyment. It’s a lot of fun to chase that football team...but you need the ability to adjust and not be rigid.” (34:31)

• On the pursuit of money:

  “There is just no correlation in any kind of common sense way of money and happiness. It just doesn’t. It’s black and white.” (36:11)

• Only true fulfillment comes from meaning, not wealth for its own sake — a message he feels people “need to see for themselves” to learn.

9. Relationships, Values, & Legacy

• Acknowledges the pride of his parents and how making them proud is "probably my strength and my weakness.” (37:11)
• Favorite/funniest moments include judging Miss America and first TV appearances — “I am not detached from how miraculous my life has been.” (38:38)
• Highest ambition:

  “I want everybody that I love to show up to my funeral with a very good feeling in their stomach about who I was.” (38:02)

10. Rapid-Fire / “Filma Bling to Excellence” (Lightning Round, 37:45–43:55)

• Biggest lesson: “Losing is the thing you should always strive for because it makes winning a lot easier.” (37:47)
• Number one professional goal: “Buy the New York Jets.” (37:58)
• Biggest regret: “Not spending even more time with the people I love.” (38:15)
• Advice to kids: “Be a good human being on their terms, not how you want to define it.” (38:29)
• Key trait that defines his success: “Tenacity...I’m fucking tenacious and it matters.” (40:43)
• Who would you meet: “Vince McMahon...I want to talk to him about character development.” (41:31)
• Advice to 21-year-old self: “Don’t do a single thing different.” (43:28)

Notable Quotes & Memorable Moments

• “I might have lost $20,000 in sales that hour, but I’ve helped my dad make millions since.” (09:01)
• “Actions carry enormous weight. Every leader should...go out of their way for the most hyperbolized executions of those things so that it becomes lore.” (09:17)
• “I literally made seven figures to give a quote.” (14:16)
• “Preparation is the only thing. The reason I do such narrow things is they’re the things I’m preparing on at all times.” (32:35)
• “There is just no correlation...of money and happiness. It’s black and white.” (36:11)
• “Tenacity...I’m fucking tenacious and it matters.” (40:43)

Timestamps for Major Segments

• Twitter/Facebook investment stories: 00:00–01:00, 21:09–22:51
• Live Shopping as the Next Big Thing: 01:34–04:54
• The Customer Service Snowstorm Story: 05:07–09:37
• VaynerMedia and Entrepreneurial Scaling: 10:56–16:06
• Philosophy on Angel Investing: 23:03–26:18
• Content, Social Media, and Attention: 27:10–29:15
• Work Ethic, Preparation: 29:15–34:13
• Money, Success, and Motivation: 34:13–36:11
• Rapid-fire/Values and Advice: 37:45–43:55

Conclusion

Gary Vee’s approach to life and business is defined by relentless curiosity, tenacity, and a willingness to take principled risks. His advice, war stories, and clear trend-spotting acumen offer a wealth of inspiration for entrepreneurs, business leaders, and anyone in search of excellence. The episode is packed with wisdom on making bold moves, serving customers, preparing for success, and prioritizing meaning over money — all delivered with Gary’s signature candor and unfiltered style.