Podcast Summary:
The GaryVee Audio Experience
Episode Title: The Career Advice Nobody Tells You
Host: Gary Vaynerchuk
Date: September 8, 2025
Episode Overview
This episode features Gary Vaynerchuk in an open Q&A with residents participating in VaynerMedia’s incubator program. The discussion centers on authentic career development, handling uncertainty, internal and external expectations, networking, diversity and inclusion, resilience, and actionable advice for young (and not-so-young) professionals. Gary emphasizes the value of intent, self-awareness, and the practical truth that career journeys are non-linear.
Key Discussion Points & Insights
1. The Origin of the Residency Program
(00:13–04:05)
- Gary explains the motivation behind creating VaynerMedia’s residency/incubator for young professionals, describing it as “selfless, selfish behavior.”
- The intent is to create a win-win: providing genuine opportunity for young people locked out of the industry while also potentially identifying future hires for VaynerMedia.
- Quote:
“We’re paying to train you—like, real talk. So it’s a real fucking winning move for a lot of people, obviously… I’m just hoping to make it a win-win for everyone. And in general, that’s how I think about business ideas.”
– Gary Vaynerchuk ([02:11])
2. Making Networking Comfortable & Effective
(04:06–07:42)
- Gary underscores that the best way to build connections is through shared interests, not just work conversations.
- He encourages residents to get comfortable with discomfort, likening networking for introverts to how he approaches working out and eating well—which he does out of necessity, not enjoyment.
- “Most people don’t network well because they’re scared of rejection. But this is a nice place. People are nice here. So saying hi is a fruitful concept.”
– Gary Vaynerchuk ([06:52])
3. Grace with Yourself During Career Changes
(07:52–12:08)
- Gary dives deep into the need for self-compassion, especially for those transitioning careers or feeling behind.
- He emphasizes that most external judgments, including hiring decisions, are deeply subjective and often serendipitous.
- Quote:
"Why would you not show yourself grace? The rest of the world is shitting on you at all times. Why not be kind to yourself? Don’t join in.”
– Gary Vaynerchuk ([09:29]) - He urges listeners to break free from the need for outside validation—even from loved ones.
4. Navigating Expectations as an Immigrant or First-Generation Professional
(12:22–14:07)
- Gary shares his experience as an immigrant, noting the cultural weight of familial expectations but stressing that ultimately, personal happiness must come first.
- "You could admire and love your parents the most … but you cannot live for them. And the second you stop living for them and live for your happiness, you actually deliver to your parents what they wanted all along."
– Gary Vaynerchuk ([13:00])
5. Patience Versus Complacency & Starting Late
(14:16–17:20)
- Addresses concerns about starting careers late or being "behind".
- Gary draws from his own story (starting VaynerMedia in his mid-30s with no office or money) to debunk the myth of linear timelines.
- “Everyone, when I talk about patience, I do not talk about complacency. They're two different words. I am patient, but I’m obnoxiously ambitious, and I go hard every day.”
– Gary Vaynerchuk ([15:13]) - He suggests using one's unique journey as a narrative asset when reaching out to future employers.
6. The Most Important Takeaway from Vayner
(17:24–18:43)
- Gary hopes employees realize they don’t have to work for environments that make them miserable:
"That you don’t have to work somewhere where you don’t feel good… there’s a way to go hard but not be in an environment that makes you unhappy or anxious." ([17:39])
- He values practical, contemporary skills over theoretical learning.
7. Advice to Younger Self & Perfectionism
(18:43–22:21)
- Gary identifies his past inability to be candid as his biggest regret.
- He encourages listeners to take risks and get comfortable with mistakes, emphasizing that fear of making mistakes leads to stagnation.
- “You gotta get comfortable with making mistakes, otherwise you’ll always be lower middle management.”
– Gary Vaynerchuk ([21:21])
8. Social Media’s Ever-Changing Landscape
(22:26–24:05)
- Gary’s key to keeping VaynerMedia relevant is adaptability: he doesn’t try to predict trends but moves quickly when attention shifts (e.g., TikTok).
- He plans for the future (e.g., VR) but is “practitioner-led” and reactive to real change.
9. Leading with Humility & Letting Go of Attachments
(24:10–26:16)
- Gary highlights humility as a core leadership trait—being open to being wrong and not getting attached to his ideas.
- “Humility is the single most important trait for a leader besides conviction… If I get stuck on my own shit, the world doesn’t care about my feelings.”
– Gary Vaynerchuk ([25:13])
10. Daily Gratitude Practices
(26:16–27:54)
- Gary roots daily gratitude in perspective—specifically, reflecting every day on the health and safety of his family.
- This practice helps him contextualize stress and anxiety.
11. Diversity, Inclusion, and DEI as a Business Imperative
(27:56–30:19)
- He foregrounds DEI as essential to the ethos and success of VaynerMedia, not a checkbox.
- “It’s very easy to prioritize it. When you prioritize it, it’s just like, why is our culture good? Because I care for it to be good.”
– Gary Vaynerchuk ([28:53])
12. Resilience, Fear, and Mental Health vs. Hustle Culture
(31:34–39:16)
- Gary describes his approach to fear as internalizing and shedding it through gratitude and self-awareness, not projecting it onto others.
- He deconstructs the contemporary conflation of ambition with burnout, asserting that hard work only becomes toxic if it’s disconnected from passion.
- “Hard work is remarkably enjoyable when you like what you’re doing and it’s not when you don’t… Don’t burn yourself out, don’t even do it.”
– Gary Vaynerchuk ([34:43]) - He sees insecurity and entitlement—not work ethic—as the real roots of workplace malaise and societal depression.
13. Entrepreneurial Lessons from Building Resy
(39:19–41:55)
- Gary and Ben Leventhal won the NYC restaurant reservation market by focusing on creating the best product and securing the most desirable venues.
- The key insight: Success in two-way marketplaces is about quality of supply and driving demand.
14. Discovering Your Passion Through Experimentation
(41:55–44:42)
- Gary advises recent graduates and young professionals to “taste” as many activities and roles as possible to discover passions.
- “You gotta go eat oysters and sweetbreads and uni and tacos and banana. Like, you have to eat shit. Right? Same with this … Join every club, everything… unless you’re tasting, you don’t know.” ([44:10])
15. Dealing with Rejection and Building True Humility
(44:56–47:03)
- Gary contends that the ability to handle rejection comes from internal humility and detachment from others’ opinions—while also not over-estimating your own.
- “I don’t give a shit about other people’s opinions, but I also don’t think my shit’s right.”
– Gary Vaynerchuk ([47:03])
Memorable Quotes & Moments
-
On Intent:
“When I think about the net net happiness and retention of this company, we’re out of control good for ad land and I’m proud of that. And I think the only way that happens is intent.”
([03:41]) -
On Grace:
“The relationship you have with yourself is literally the whole game.”
([09:16]) -
On Risk and Experimentation:
"You should be spending... people who really dwell or... are passionate, excited about finding their thing. Well, you've got to find it. So... go do a ballroom dancing class, right? Take a course on Coursera for, like, accounting... Unless you're tasting, you don't know."
([44:00]) -
On DEI:
"It’s good for business."
([28:35])
Timestamps for Key Segments
- 00:13 – Why Gary Created the Residency Program
- 04:06 – Making Networking Comfortable
- 07:52 – Self-Compassion and Grace
- 12:22 – Advice for Immigrants/First-Generation Professionals
- 14:16 – Patience, Complacency, and "Late" Starters
- 18:43 – The Biggest Lesson for Gary’s Younger Self
- 22:43 – Adapting to the Social Media Landscape
- 24:10 – Letting Go of Ideas as a Leader
- 26:16 – Practicing Daily Gratitude
- 27:56 – DEI as Imperative
- 31:34 – Handling Fear & Mental Health Versus Hustle
- 39:19 – Building and Winning with Resy
- 41:55 – Discovering Your Passion by "Tasting"
- 44:56 – Handling Rejection and Developing Humility
Final Takeaways
Gary Vee’s candid, high-energy style illuminates a modern, human-centric approach to career building: Intent matters more than background; humility trumps performance perfection; experimenting widely leads to discoverable passion; and a truly sustainable hustle is rooted in joy and alignment. For any early-career or mid-career professional, these lessons demystify the myth of prescribed paths and re-center fulfillment, real self-worth, and resilience as the ultimate career wins.