In Search of Excellence – E170

Guest: Gary Vaynerchuk ("Gary Vee")
Host: Randall Kaplan
Date: August 16, 2025

Episode Overview

This episode features serial entrepreneur and social media icon Gary Vaynerchuk, tracing his journey from Soviet immigrant to CEO. Host Randall Kaplan and Gary discuss the immigrant mentality, Gary's early entrepreneurial experiences, family values, overcoming adversity, and the mindset required to achieve lasting excellence and legacy. The conversation is candid, emotional, and filled with actionable insights about resilience, gratitude, work ethic, and the compounding impact of small breaks—and setbacks—throughout life.

Key Topics & Insights

1. The Power of Family & Early Immigrant Experiences

• Jack, Bob, and Arlene: Pivotal Family Figures

  • Gary recounts the role of Jack Siegelman (a distant relative who first left the USSR for America) and his children, Bob and Arlene, in helping his family get a foothold in the US.
  • Quote:

    “Self made is a very funny thing because it’s unbelievably true, but also very contextual...luck is timing, serendipity is an ingredient, but just one small ingredient of the outcome.” – Gary (06:22)

  • Arlene bought Gary’s father his first car and helped him land a stocking job at the family liquor store—the start of the Vaynerchuk family trajectory in America.
  • [02:09–06:52]

• Gary’s Mother: Resilience Personified

  • Gary’s mother, Tamara, lost her own parents young and endured immense hardship in the Soviet Union, yet became Gary’s emotional rock.
  • Quote:

    “She is the strongest person I know. She’s just incredibly strong, and she made me very strong...everything that I know is a core ingredient to why I’m successful.” – Gary (08:00)

  • [06:52–09:24]

2. The Importance of Encouragement and Mindset

• Gary’s Upbringing: Daily Affirmations
  • His mother constantly communicated her belief in him, reinforcing that he was special, had a “golden heart,” and was capable of anything.
  • Quote:

    “There was probably not a day in my life between 5 and 15 where my mother didn’t give me some version of that: ‘I believe in you’.” – Gary (09:33)

  • [09:24–10:31]

3. Childhood, Adversity, and Defining Moments

• The Knitted Jersey Story

  • Growing up poor, Gary’s mother worked late nights to knit him a Jets jersey after explaining they couldn't afford to buy one.
  • Quote:

    “It’s got a number five, it’s got my name Gary on the back, and it is my prized possession...it’s just a little head nod to my mom, who is my hero.” – Gary (14:27)

  • [10:31–15:05]

• Poverty and Motivation

  • Gary clarifies that not having money didn’t directly drive his ambition; he always had the entrepreneurial “bug”—it was in his DNA.
  • Quote:

    “It’s hard to be hungry when you’re constantly fed...but for me it wasn’t need or envy, I have a curiosity in my stomach.” – Gary (17:00, 19:36)

  • [16:33–20:49]

• Bullying and Resilience

  • Shares stories of being bullied, including a harrowing memory of being forced to drink from a can of urine. Despite adversity, bullying never penetrated his core—he remains resilient and optimistic.
  • Quotes:

    “Bullying has never penetrated me...it’s a good story that paints a picture that not everything is rosy, but I can give you a lot of those events.” – Gary (23:48)
    “I want to win, but I don’t want you to lose.” – Gary (25:33)

  • [20:49–26:47]

4. The Entrepreneurial “Gene”—Nature vs. Nurture

• Gary’s Childhood Hustles

  • Lemonade stands (with “franchising”), selling candy, caroling, and selling picked flowers to neighbors—demonstrating early entrepreneurial instincts.
  • Quote:

    “Entrepreneurial talent is one of them...if you match people with and without natural talent and they all put in the same amount of work, the ones with talent win. Talent’s part of the entrepreneurial equation.” – Gary (27:49, 29:38)

  • [26:47–31:10]

• Entrepreneurship as Talent vs. Teachability

  • Gary argues that while everyone can improve, some are naturally wired for entrepreneurship—just as in singing or sports.
  • “But do I believe that if I was matched up with somebody who has less or more natural entrepreneurial talent and we all put in the same amount of work, that there’s a higher propensity that I would have that success? Yeah, I believe that.” – Gary (29:38)

5. Turning Points: Baseball Cards & the Wine Business

• From Card Trading to Commerce

  • The sixth-grade baseball card club gave Gary his first taste of business, leading to card shows, price guides, and a discovery of market merit.
  • Quote:

    “That was like game changing. And then I did a card show...I had the bug.” – Gary (31:53, 33:30)

  • [31:10–35:08]

• Setbacks: From Profitable Cards to $2/Hour

  • After poor grades, Gary’s father forced him to work in the family liquor store, earning $2/hr instead of hundreds at card shows.
  • Initial resentment eventually transformed into appreciation after Gary saw parallels between wine collecting and card collecting.
  • [35:08–36:48]

• Learning Honesty and Integrity in Sales

  • A moment when Gary exaggerated wine sales numbers led to a stern lesson from his father about truthfulness—key to Gary’s future business values.
  • Quote:

    “If you embellish to my dad, you’ve done a catastrophic lie. He’s very rigid when it comes to lying, embellishing...he tweaked and tightened me because I think it’s made me more respectful.” – Gary (38:33)

  • [36:48–39:48]

6. Overcoming "Loser" Labels

• School Struggles vs. Market Success
  • D and F student, considered a future failure by peers’ parents; Gary found validation through real market success selling cards and wine.
  • Quote:

    “We were all propagandaed and brainwashed...that your college where you go to college is the singular black and white proxy to being successful.” – Gary (41:41)

  • [39:48–42:52]

7. Pivotal Moment: Discovering the Internet

• Freshman Year at Mount Ida College: The AOL Epiphany
  • Gary’s first exposure to the internet in his dorm was transformative.
  • Quote:

    “I just knew. I literally remember seeing the reflection of my own face in the monitor saying, ‘this is it.’” – Gary (44:01)

  • He immediately realized the web’s potential for commerce, deciding to bring his family’s wine business online.
  • Distinguishes between the “immigrant kid” drive to succeed for the family and the typical American mindset.
  • [43:04–46:48]

Notable Quotes & Memorable Moments

| Timestamp | Speaker | Quote/Highlight | |-----------|---------|---------------------------------------------------------------------------------| | 06:22 | Gary | “Self made is a very funny thing because it’s unbelievably true, but also very contextual…” | | 09:33 | Gary | “There was probably not a day in my life between 5 and 15 where my mother didn’t give me some version of that: ‘I believe in you’…” | | 14:27 | Gary | “It’s got a number five...it is my prized possession...a head nod to my mom, who is my hero.” | | 19:36 | Gary | “For me it wasn’t envy or need...I have a curiosity in my stomach.” | | 23:48 | Gary | “Bullying has never penetrated me...it’s a good story that paints a picture that not everything is rosy…” | | 25:33 | Gary | “I want to win, but I don’t want you to lose.” | | 29:38 | Gary | “Do I believe...talent’s part of the entrepreneurial equation? Yeah, I believe that.” | | 38:33 | Gary | “If you embellish to my dad, you’ve done a catastrophic lie...he tweaked and tightened me…” | | 41:41 | Gary | “We were all propagandaed and brainwashed...where you go to college...undisputed proxy to being successful.” | | 44:01 | Gary | “I literally remember seeing the reflection of my own face in the monitor, saying, ‘this is it.’” |

Timestamps – Major Segments

• 02:09–06:52 Family immigration story, gratitude for distant relatives and early breaks
• 06:52–10:31 The influence of Gary’s mother, encouragement, and development of self-belief
• 10:31–16:47 Growing up poor, the Jets jersey, childhood dreams and adversity
• 16:47–20:49 Motivation, the role of money, and DNA vs. environment
• 20:49–26:47 Bullying, adversity, and coping mechanisms
• 26:47–31:10 Childhood entrepreneurship and the “gene” for hustle
• 31:10–35:08 Baseball cards and discovery of market economics; first real business wins
• 35:08–39:48 Forced transition to wine store, setbacks and learning integrity
• 39:48–43:04 Academic struggle, overcoming labels, importance of real-world validation
• 43:04–46:48 Discovering the internet, realizing the path to modern entrepreneurship

Episode Tone

Candid, introspective, direct, occasionally emotional, with moments of humor and signature Gary Vee energy.

Conclusion

This episode is an intimate look at how upbringing, adversity, and immigrant values shaped Gary Vee’s mindset and trajectory. Listeners gain insights into the compounding effects of small kindnesses, the enduring power of encouragement and self-belief, and why authentic entrepreneurial drive matters more than circumstance. The conversation is filled with honest reflection, memorable stories, and practical wisdom—a must-listen for anyone interested in resilience, legacy, and building something from nothing.

(Stay tuned for Part Two.)