The GaryVee Audio Experience
Episode: Why Humility is the #1 Skill a CEO Can Have
Date: February 9, 2026
Host: Gary Vaynerchuk
Overview
This episode of The GaryVee Audio Experience brings together a table of entrepreneurs, content creators, and subject-matter experts for a candid, high-energy mastermind with Gary Vaynerchuk. The central theme revolves around humility as the key trait for any CEO, but the discussion dives deep into practical strategies for personal brand growth, scaling digital businesses, hiring, and, most importantly, detaching self-worth from business outcomes. Gary brings his trademark straightforwardness, peppered with analogies and real talk about staying authentic, playing the long game, and the power of humility in navigating both success and setbacks.
Key Discussion Points & Insights
1. Building & Detaching from Your "Sandcastle"
- Gary’s Sandcastle Analogy:
- Quote: “I'm wildly curious how big I can make it. Nothing else, none of it defines me because I have my definition somewhere else. Definition is if people think I'm a good guy.” (00:00)
- Gary likens business building to kids constructing sandcastles on the beach—joy in creation, but detachment from the result. This mindset keeps his ego in check regardless of the outcome.
2. Navigating Career Pivots & Content Creation
- Teacher considering a career pivot worries about losing the hands-on fulfillment of teaching.
- Gary’s Advice: You can replicate "in the trenches" experience via nonprofit work, bootcamps, or physical events (01:14–03:14).
- Quote: “You can replicate growing up at 18 to 22 now. Not by getting into $100,000 in debt... You can grow up. You don't have to be a teacher to be in the trenches. You can replicate it in a different way. You understand?” (02:03)
3. From Social Media Hesitation to Business Boom
- Mobile Editing Entrepreneur's Story:
- Deleted Instagram, returned, sensed opportunity in mobile editing, built a $99 product, scaled to six figures/month (04:32–05:47).
- Gary’s Advice on Scaling: Focus on serving individual customers (“the pebbles”) before jumping to big clients (“the boulders”), but keep options open (06:20–07:46).
- Quote: “I want you to build more leverage with the pebbles for a little bit longer. The boulders are always there. Does that make sense?” (06:18)
4. Standing Out in a Sea of Education & Branding
- UGC Coach shares the struggle of being unique in an info-saturated market.
- Gary’s Take: Relentlessly be yourself—polarizing delivery is good. Authenticity will ultimately “convert” skeptics (10:38–11:42).
- Quote: “It is full obsession or full fuck you. But I am who I am...” (10:38)
- Leveraging testimonials is valuable in moderation but shouldn’t dominate content (14:05–14:13).
5. Women's Health: Content to Community to Brand
- Women's Health Practitioner shares rise from health struggles to bestselling author/entrepreneur.
- Built brand by vlogging personal journey and responding to audience demand for digital guides (15:00–16:29).
- Gary on Scaling: Focus on hiring a COO/operations head over a cofounder initially (17:21–18:18).
- Quote: “You don't marry the first person that you think you want to date. You date them. You could get a head of operations... No, I would not do a cofounder.” (17:45)
6. Burnout, Leverage, and the Right Hires
- Real Estate Agent discusses burnout and personal brand/family juggle.
- Gary on Delegation: Hiring isn’t enough—hire the right person, keep tuning your roles.
- Quote: “You have to hire the right employees, and you have to learn how to become a better boss.” (24:43)
- Reinvest as much as possible if aiming to build an empire (the answer to “What % should I reinvest?”).
7. Curiosity as Motivation, Not Validation
- Gary’s Why for Building “an Empire:”
- “I'm wildly curious how big I can make it. Nothing else. Straight curiosity. I'm just wondering... That's it.” (27:53–29:03)
- Detachment: The business or persona (“GaryVee”) doesn’t define him; he’s driven purely by the challenge.
8. Humility, Feedback, & Longevity
- Gary’s Core Principle for Success:
- “My greatest skill set by far is humility. It's not obvious... I don't hear all of you when you say I'm the best, which allows me to not hear you when you say I'm the worst.” (31:12)
- True durability comes from tuning out both praise and criticism and defining yourself by your own principles, not fleeting success.
9. Scaling Teams Authentically
- Hire to Your Nature:
- Night owls should hire other night owls; empathy is key for leadership, as long as there is no hypocrisy (36:54–39:03).
- “Hire vampires.” (37:05, 37:20)
10. Coaching: Practice vs. Theory
- Does a Coach Need to “Do” What They Teach?
- Not strictly, but it’s more credible if they do.
- Quote: “I do not think that is required, but I think it is really epic when you do do and have gone through and do know.” (39:52)
11. Brand Longevity & The Gold Rush of Social Reach
- Sustaining a Brand:
- Don’t play a role—be yourself and remain unjudging, through hot and cold streaks (41:44–42:39).
- Urgency: Social media reach is a gold rush—build your brand hard while opportunity lasts because the window won’t last forever (43:24–end).
Notable Quotes & Timestamps
-
On Detachment & Motivation:
- “I'm wildly curious how big I can make it. Nothing else, none of it defines me because I have my definition somewhere else.” – Gary (00:00)
-
On Replacing "In the Trenches" Experience:
- “You don't have to be a teacher to be in the trenches. You can replicate it in a different way. You understand?” – Gary (02:03)
-
On Leveraging Community vs. Big Clients:
- “Keep building leverage with the pebbles… the boulders are always there.” – Gary (06:18)
-
On Being Polarizing & Authentic:
- “It is full obsession or full fuck you. But I am who I am...” – Gary (10:38)
-
On Delegation & Hiring:
- “You have to hire the right employees, and you have to learn how to become a better boss.” – Gary (24:43)
- “You don't marry the first person that you think you want to date.” – Gary (17:45)
-
On Leadership:
- “My greatest skill set by far is humility. It's not obvious... I can't take your judgments, your praise or your shitting on me to the field. I've got to play the game.” – Gary (31:12)
-
On Team Culture:
- “If I'm a bat, hire vampires.” – Gary (37:05)
-
On Coaching:
- “I do not think that is required, but I think it is really epic when you do do and have gone through and do know.” – Gary (39:52)
-
On Brand Longevity & Urgency:
- “This is the gold rush of attention... so if I'm right, how hard do you think you should go the next five to seven years to build your brand, your person? Very hard. The end.” – Gary (43:24)
Noteworthy Moments & Timestamps
- The Sandcastle Motivation Analogy: 00:00, 27:53–29:03
- Delegation & Burnout Real Talk: 22:26–24:29
- Hiring for Personal Strengths (Night Owls): 36:54–39:03
- Importance of Humility: 31:12–32:41
- The Value of Authenticity in Content: 10:38–11:42
- Brand-building Urgency/Gold Rush Metaphor: 43:24 to end
Conclusion
Gary closes with a call to embrace humility, relentlessly double down on self-awareness, and go as hard as possible on brand-building while the unprecedented window of social reach is open. His advice, tough love, and business analogies remain rooted in authenticity and curiosity—not ego or legacy. For CEOs and creators alike, humility—combined with gritty consistency—is the number one determinant of long-term impact and peace.
Recommended for:
Entrepreneurs facing scaling pains, those grappling with delegation, content creators overwhelmed by competition, and anyone craving inspiration on detaching identity from business success—told in Gary’s honest, encouraging, NSFW style.