Podcast Summary

The GaryVee Audio Experience
Episode Title: The Truth About Your Energy, Insecurity, and That Thing You've Failed at for 10 Years
Host: Gary Vaynerchuk
Release Date: October 8, 2025

Episode Overview

This episode of The GaryVee Audio Experience centers on energy, insecurity, and persistence in the face of long-term struggles. Gary takes listener questions, offers practical and emotional advice, and is joined by entrepreneur Michael Chernow for a conversation about wellness, investing, and shifting your habits for better outcomes. The episode dives deep into how to overcome internal barriers, the importance of patience and self-worth, and the harsh realities of ambition, all conveyed in Gary’s distinct, no-nonsense style.

Key Discussion Points & Insights

1. Investing in Collectibles and Spotting Trends

[01:57 - 04:52]

• Gary explains his bullishness on rare fictional character trading cards, citing the evolution of nerd culture and the growing intersection between comic con, sports cards, and collectibles.
• Patience in Collecting:
  • Gary emphasizes the importance of patience in the collectibles market, using stories of investments like a Ronaldo rookie card as examples of how timing is crucial.
  • “When you have patience with collectibles and you see something, you know, oftentimes it works out. ... If you’re looking for a quick flip, you know, sometimes it works out tremendous and sometimes it works out terrible.” — Gary, [03:35]
• Thesis: The next wave for trading cards is fictional character rookie cards (e.g., Batman, Spider-Man, Shrek).

2. Entrepreneurship, Crowdfunding, and Creatures of Habit

With Michael Chernow
[04:52 - 13:51]

• Michael Chernow talks about launching a crowdfund for Creatures of Habit, his wellness brand focused on healthy habits and nutrition.
• Gary and Michael emphasize giving the community early investment opportunities, made possible by StartEngine and the democratization of private investing (thanks to the JOBS Act).
  • “All the opportunities I had in investing in Twitter and Facebook... the JOBS Act allowed people to invest in companies.” — Gary, [08:12]
• Michael shares an origin story:
  • He DM’d Gary to pitch an exclusive deal with his restaurants for Empathy Wines, leading to their partnership — a masterclass on taking initiative and creating value.
  • “I’m just here to tell you, take the swing.” — Michael Chernow, [11:10]
  • Memorable Moment: Michael’s story about his son running a museum/gift shop with found objects from the yard, illustrating that entrepreneurial spirit is often innate.

3. Advice for Women in Entrepreneurship

[13:56 - 22:31]

• Gary addresses the double standards faced by female entrepreneurs.
• Key insight: Everyone faces insecurity and bias in different ways.
  • “That men are just as insecure as women? No shit.” — Gary, [14:10]
• Don’t waste energy convincing the ‘broken’.
  • “Anyone who does that to you isn’t someone you want to be associated with anyway. ... Why are you wasting your time on someone that doesn’t believe in you? Who gives a shit?” — Gary, [16:13]
• Entrepreneurship as a great equalizer:
  • “The market decides… It doesn’t know if you’re black, white, Hispanic, or Russian, girl or boy. It’s just a blank market.” — Gary, [21:04]
• Flaws and Fixers: Gary talks about his own tendency to be a fixer, a trait he associates with both men and women.

4. On Insecurity and Loneliness

[22:31 - 27:22]

• Gary tells a listener that feeling alone at a table is a sign of insecurity, not an unchangeable social status.
  • “You need to work on yourself. You’re deeply insecure.” — Gary, [22:43]
• On self-worth:
  • “I do not understand the concept of not being your biggest fan.” — Gary, [23:38]
• Memorable, light moment: Gary uses the example of comparing a listener to George Clooney, explaining that everyone is someone’s type and that personal validation shouldn’t be externally dictated.

5. Pursuing Your Dream Despite Family & Financial Pressure

Conversation with Melanie
[27:22 - 34:45]

• Melanie, a 23-year-old from the Philippines, dreams of being a pop girl group member but feels drained by financial pressures and family expectations.
• Gary calls out her belief that she doesn’t have enough energy:
  • “You’re peddling some bullshit on me… Do you know that you have unlimited energy?” — Gary, [29:36]
• Dreams feed energy:
  • “The dream is gonna fucking feed you. Right now, you’re not being fed, so you don’t have enough energy. You’re mixing it up.” — Gary, [32:47]
• Key advice: If you want a dream, you don’t get to take vacations — dreams are taken, not given.
• Try the dream and work to avoid regrets later in life.

6. Knowing When to Quit

[35:07 - 37:48]

• A listener named Vic asks about persisting after a decade of no progress.
• Gary’s unfiltered response:
  • “You should quit. 10 years, Vic. ... You’ve been failing for a decade at this thing. This thing’s fucking not gonna work. 10 years, Vic.” — Gary, [35:16]
• Memorable Moment: Gary’s humorous side rant about how turkeys and hippos are more dangerous than they seem, blending analogies about persistence and letting go.

7. Scarcity vs. Awareness in Art

[37:48 - 39:05]

• Gary debunks the myth that awareness kills scarcity:
  • “Awareness is required to create scarcity. ... She’s got it twisted. She thinks that awareness takes away the mystique to create scarcity. Scarcity is not a byproduct of awareness.” — Gary, [38:44]
• Memorable quote:
  • “Everyone here who knows what the Mona Lisa is, raise your hand. Oh, weird. Everyone fucking knows.” — Gary, [39:03]

Notable Quotes

• “When you have patience with collectibles and you see something, you know, oftentimes it works out.” — Gary [03:35]
• “I’m just here to tell you, take the swing.” — Michael Chernow [11:10]
• “Anyone who does that to you isn’t someone you want to be associated with anyway.” — Gary [16:13]
• “The dream is gonna fucking feed you. Right now, you’re not being fed, so you don’t have enough energy.” — Gary [32:47]
• “You should quit. 10 years, Vic.” — Gary [35:16]
• “Awareness is required to create scarcity.” — Gary [38:44]

Timestamps for Key Segments

| Segment | Timestamp | |----------------------------------------------|------------| | Collectibles & Cards | 01:57–04:52| | Creatures of Habit & Entrepreneurship | 04:52–13:51| | Advice for Women in Entrepreneurship | 13:56–22:31| | On Insecurity & Self-worth | 22:31–27:22| | Melanie’s Dream & Family Pressure | 27:22–34:45| | When to Quit | 35:07–37:48| | Scarcity and Awareness in Art | 37:48–39:05|

Tone & Style

Gary’s signature direct, energetic, and sometimes brash manner is a throughline in this episode: blunt truths, motivational pushes, and frequent use of analogies and humor ("turkeys are nasty motherfuckers", “Karma... I love business. ... It’s just how the world works.”).

Final Takeaways

• Energy and motivation are self-generated, especially when tied to pursuing genuine dreams.
• Don’t let insecurity, societal narratives, or external voices dictate your worth or direction.
• Sometimes, quitting is the courageous and strategic move (especially after a decade).
• Opportunities are more accessible than ever, and building winning habits often starts by simply taking a shot or DM’ing someone.
• Awareness creates, not diminishes, value.

For anyone craving straight talk on energy, insecurity, and the realities of chasing (or letting go of) dreams, this episode delivers the classic GaryVee blend of hard truths and unwavering encouragement.