The GaryVee Audio Experience

Episode: Career Pivots, Entrepreneurship and Overcoming Fear | Tea with GaryVee Ep. #85
Date: September 17, 2025
Host: Gary Vaynerchuk

Overview

In this dynamic episode of "Tea with GaryVee," Gary Vaynerchuk takes live questions from audience members about career pivots, overcoming personal obstacles, entrepreneurship, social media strategy, prioritizing experience vs. money, navigating family dynamics, and the realities of building businesses (and personal brands) in today’s environment. With his signature directness, Gary addresses the roots of hesitancy, the dangers of enabling negativity, and the myth that you need to choose between stability and passion. The episode is packed with tough love, memorable analogies, and candid advice for anyone who feels stuck or uncertain about their next move.

Key Discussion Points & Insights

1. Completing What You Start: Is it a Lack of Resilience or Self-Awareness?

(01:37–03:32)

• Caller (Taya, 36): Struggles to finish what she starts—wondering if it’s a flaw or a sign of good self-awareness.
• Gary’s Take:
  • You could be lacking resilience or consistency, or you might just have strong self-awareness about your interests.
  • Don’t beat yourself up for pivoting on creative/offensive tasks; focus energy on the black-and-white responsibilities in your life.
  • Quote: “Either you’re soft and insecure, or you’re self-aware and confident. I don’t know. But I don’t beat myself up when I don’t finish tasks when they’re creative and on offense.” (02:22, Gary)

2. Loving People with Boundaries: Cutting Negativity, Not Loyalty

(03:32–06:14)

• Caller (John): How to love someone deeply without their negativity overwhelming you.
• Gary’s Take:
  • Limit the time spent with negative people, even family; loving someone doesn’t equal enabling their behavior.
  • Loyalty often gets confused with enabling toxicity. Real love might mean tough conversations, candor, and even stepping away if necessary.
  • Quote: “Being loyal to your toxic mom doesn’t mean to sit and enable her toxic behavior… the actual requirement is to have candor with them and try to help them.” (05:14, Gary)
  • The importance of accountability for the atmosphere you cultivate around you and not falling into victimhood or endless complaining.

3. Building a Personal Brand While Working a Corporate Job

(06:14–07:43)

• Caller (Maria): Wants to establish a presence online without disrupting her corporate standing.
• Gary’s Advice:
  • Share professional, non-controversial content; keep personal life off social if you want privacy.
  • Don’t post for algorithmic validation—post what aligns with your genuine self.
  • Quote: “The theme of today’s morning so far is: you’re in control. Until you realize that, you lose.” (07:27, Gary)

4. Pursuing a Passion with Practicality: Dual Paths and Regret

(07:43–08:33)

• Caller (Luke, 25): Loves both finance and music, fears he’ll never ‘make it’ in music.
• Gary’s Take:
  • At 25, you have the energy to go after both your job and your passion. Don’t give in to regret—start creating even when no one listens.
  • You don’t have to choose one; balance both as long as you can.

5. Entrepreneurship: Marketing for Clients AND Recruitment

(08:33–16:03)

• Caller (Rainia): Leads a B2B sales group and wonders whether to market her product or her business for recruitment.
• Gary's Core Points:
  • Always "and," not "or" — market both to drive business and find the right talent.
  • Customize your marketing to each platform and type of audience.
  • Consistency and volume are key (“Are you posting 8, 10, 12 times a day or not?”).
  • On Recruitment:
    • Don’t waste energy convincing people to love sales if they don’t already have the DNA for it. Look for people who are naturally drawn to it.
    • Quote: “Sales is a fucking DNA game. You are either a fucking salesman or you are not… Get that word ‘convince’ out of your fucking vocabulary.” (13:06–15:49, Gary)
  • The importance of not chasing views, but rather doing the basics that work.

6. Experience Versus Money: What Really Matters?

(16:13–19:57)

• Caller (Parker, 24): Struggling to choose between a higher salary or gaining experience.
• Gary’s Perspective:
  • Experience is more consistent and valuable long-term; money can be a destructive catalyst if internal foundations aren’t solid.
  • Many chase easy money, but if you’re broken inside, sudden wealth will only amplify problems.
  • Memorable Rant: Calls out “insurance scams” as an example of the money-game mindset he saw growing up, connecting it to the naïve belief that money solves everything.
  • Quote: “Until you fucking get your fundamentals right internally, you have no shot. Go win the lotto. Why do so many lotto winners lose? …Experience is a hell of a lot better than money.” (19:27, Gary)

7. Dabbling Versus Doubling Down (The “Real” Business vs. Speculation and Passion Projects)

(19:57–32:03)

• Caller (Chris Lyons): Paid off his mortgage via meme coins, runs a tire shop, and builds a personal brand. Struggles to focus and feels confused about where to invest energy.
• Gary’s Core Advice:
  • If you have a real, cash-positive business that takes little time, don’t neglect it in favor of gambling on speculative projects.
  • Brilliant “relationship” analogy: Stable business = reliable partner; risky, adrenaline-fueled projects = fleeting excitement.
  • Quote: “You have this reliable, wonderful, solid girl… and over here you’ve got a fucking stripper… addicted to the glitter… what do you think’s going to happen, brother?” (23:23, Gary)
  • Don’t build your brand on lucky breaks—focus on long-term value and sustainable plays.
  • Social content creation: Spend more time feeding the scroll (posting) than consuming it. Use consumption purposefully.
  • Quote: “A lot of people spend all their time consuming the scroll instead of feeding the scroll.” (30:24, Gary)
  • Incremental gains from focusing on efficiency, not just time spent.

8. Taking (or Rejecting) Family Support: Boundaries and Ownership

(32:03–36:43)

• Caller (Jimmy): Feels “forced” to take money from parents; wonders if he needs to cut ties to break free.
• Gary’s Candid Take:
  • You have total agency—no parent can force you to accept money if you don’t want it.
  • Some parents use money to manipulate/control—but refusing is still an option.
  • Quote: “Jimmy, you’re a grown ass man. What are you talking about? Forcing you? What, your mom rolls up, punches you in the head and stuffs dollars in your fucking pants?” (32:35, Gary)
  • Points out that real freedom sometimes requires uncomfortable decisions, but in most cases, you can just “say no” and set boundaries.

Notable Quotes & Memorable Moments

• On Accountability: “In life, you either act, or you complain and blame. And I just think living a life grounded in blaming and complaining is a very unhappy life.” (05:56, Gary)
• On Social Media: "People post things that really expose that they're addicted to the insecurities of the algorithm." (06:55, Gary)
• On Sales Recruitment: “You do not want someone on your sales team that you have to convince to get excited about sales.” (13:13, Gary)
• On Experience vs Money: “Experience is dramatically more universal and more consistent than money. Money is a catalyst. The problem is it could be a catalyst for bad.” (16:27, Gary)
• On Focus: "It's not about working more hours. It's… being more effective… A lot of people that are playing in crypto or any genre that plays out online... end up spending all their time consuming the scroll instead of feeding the scroll." (30:24, Gary)
• On Personal Freedom: "You can do whatever the fuck you want… There are people who aggressively as parents, try to push money down their kids throat for one reason: to parent their kids in perpetuity… Every spoiled kid… can just say no." (33:16–34:17, Gary)

Episode Highlights by Timestamp

• 01:37 — Taya: Finishing what you start; resilience vs self-awareness
• 03:32 — John: Balancing love and boundaries with negative friends/family
• 06:14 — Maria: Posting on social media while keeping a low corporate profile
• 07:43 — Luke: Pursuing passion projects without quitting your job
• 08:33-16:03 — Rainia: When to market for business vs recruitment; sales DNA; volume/consistency of posting
• 16:13 — Parker: Experience vs. money; growing up with a money-chasing mindset
• 19:57 — Chris Lyons: Doing too much, speculation vs real business, personal branding, social content efficiency
• 32:03 — Jimmy: Rejecting parental financial “help”; family boundaries and self-ownership

Tone & Takeaways

Gary is classic Gary in this episode: no-nonsense, direct, profane, and deeply empathetic beneath the tough talk. He emphasizes personal responsibility, the value of long-term thinking, and the need for self-awareness—while also challenging listeners to take real action, set boundaries, and drop the excuses, regardless of their circumstances.