The GaryVee Audio Experience

Episode: Losing Your Job, Finding Your Purpose, and Why Posting on LinkedIn Changes Everything

Date: November 12, 2025
Host: Gary Vaynerchuk

Episode Overview

This episode of Tea with GaryVee hones in on some of the most urgent and real-life challenges people face today: losing a job, contemplating career pivots, starting something new, and dealing with doubt or external shifts (like AI replacing jobs). Gary brings his signature mix of tough love, practicality, and encouragement, hammering home the power of self-awareness, “offense” (marketing), being proactive on LinkedIn/social, and—importantly—giving yourself grace during periods of personal difficulty.

Listeners hear Gary answer live questions from callers, covering everything from being laid off at 44, managing stress at work, when to go full-time on a side hustle, failure, insecurity around creating content, and living with chronic illness as a business owner. As always, Gary’s tone is direct, engaging, and empathetic.

Key Discussion Points & Insights

1. Job Loss and The New Reality of Work

• AI & Market Shifts: Gary warns that many will lose their jobs in the next 18 months, not just due to AI but broader economic shifts. ("The biggest companies are getting bigger...AI is a really big deal." – 00:23)
• What to Do First When You’re Let Go:
  • Don’t default to sending resumes.
  • GO HARD on creating content on LinkedIn around your expertise.
  • Share your knowledge: “We must put out LinkedIn content around what you know, what you like, what you care about.” (00:53)
• Memorable Quote:
  • “Fucking LinkedIn’s your answer...your basic resume is not going to cut it.” (01:33)

2. Passion Project vs. Full-on Business

• Balancing Regret and Financial Anxiety:
  • Gary says the key is weighing your risk tolerance versus your regret tolerance. There’s no magic moment to "quit"; it’s about your signals and situations.
  • Watch out for delusion: “Too many people are delusional and think they're rappers...for 20 years and it's not there.” (03:12)
  • The savior is MARKETING: “Businesses need marketing. Marketing is the offense of business.” (03:34)
• Tactic:
  • Ramp up your social media to drive sales. Consume the “Attention” guide on GaryVee.com for practical content tips.

3. Managing Job Misery When You Can’t Afford to Quit

• Practical Steps:
  • “Quitting your job when you're in his situation is not practical. Quitting your job after you've applied to 900 banks...that's practical.” (05:34)
  • Apply to every bank/hardware store in a 40-mile radius!
• Dealing with Complainer Mentality:
  • “Complaining doesn't work. All you do is...rolling in your own. Get another banking job, man. It's real out here.” (08:21)
• Tough Love:
  • “Everything’s hard. Once you fall in love with hard, it gets good.” (08:40)

4. Knowing When to Go All-In on a Side Hustle

• Case Study – Jake’s Edutainment Business:
  • Side hustle: Animatronic dinosaur shows for kids, $170k in revenue with high margins, part-time effort.
  • Gary’s Take: Jake should quit his job and go all-in; he has savings and the business is profitable.
• Memorable Exchange:
  • “What are you thinking about? I think about a lot of shit too, but you need to do, bro.” (13:13)
  • “The reason you don’t want to leave your job is you know it’s a joke.” (17:06)
• Backup Plan:
  • “If it fails, you learn you’re not an entrepreneur and come work at Vayner. You make less money, but you’ll learn.” (17:14)
• Takeaway: Don’t cling to easy but stagnating work when your side hustle shows real momentum.

5. Starting from Zero as a Creator

• Overcoming Insecurity:
  • “Your money means nothing...Posting on social and starting is completely based on self-esteem and insecurity.” (18:35)
  • Everyone’s excuse for not posting (not smart enough/attractive enough/afraid of judgment) boils down to insecurity.
  • “Almost every single person watching this right now is not posting because they're insecure. Period. End of Story.” (18:40)
• Advice:
  • Start anyway; being broke, young, or inexperienced isn’t a barrier to starting.

6. Building Your Brand/Practice as a Psychotherapist (or Other Professional)

• Algorithm & Platform Mastery:
  • “You gotta get better...If you're not growing, you're not as good right now as you were in 2020.”
  • Practical: Try new formats, more platforms, and adapt to cultural shifts (platforms, algorithms, culture). (21:08)
• Quote:
  • “The algorithm is not hurting everyone, it's hurting everyone who's not good.” (22:34)

7. Making Money Online (Even Later in Life)

• Best Opportunity Now: Live Social Shopping
  • “I believe live social shopping is the number one way that people can make...” (25:45)
  • Platforms: Whatnot, TikTok Shop, Twitch, TalkShopLive, eBay, etc.
  • Particularly achievable for retirees via flipping, thrift shopping, antiques, or live-sales.

8. Advice for Young People with Non-Active Interests (Salvatore’s Mom)

• Do the Work:
  • “If your 16-year-old wants to be a mechanic, you make him do it. Break your dishwasher and have him fix it.” (29:13)

9. How to Ease Anxiety for Immigrants and Immigrant Advocates

• Core Message: Focus on What You Can Control
  • “You can't control anything, actually. You must adjust to reality.” (33:00)
  • Happiness and opportunity are not tied to location—America is not the variable, you are.
• Quote:
  • “America is not the variable of happiness. You are the variable of happiness...” (35:36)

10. Business Ownership with Chronic Illness

• Grace Over Guilt:
  • “Give yourself grace...You can't hustle 18 hours a day, 365 days a year.” (36:53)
  • You’re not weak or lazy for navigating personal limitations. Don’t dwell in it, but don’t punish yourself either.
• VeeFriends Reference:
  • “Graceful Goldfish—underrated VeeFriend. I can’t wait to develop that character.” (36:59)

11. Protecting Your Brand in the Age of Deepfakes

• Embrace, Don’t Fear the Tech:
  • “I'm going to use deepfakes to build my brand...You can lawyer up or you can take a surfboard and ride it.” (41:15)
• Future-Proofing:
  • Gary plans to allow fans to generate videos of him, flipping the risk into an opportunity.

Notable Quotes & Memorable Moments

• On job search and LinkedIn:
  • “We must put out LinkedIn content around what you know, what you like, what you care about. That's just like it.” (00:53)
• On delaying action:
  • “You thinking about it means nothing. I've literally given you a full parachute...” (13:33)
• On content creation fears:
  • “Almost every single person watching this right now is not posting because they're insecure.” (18:40)
• On entrepreneurship risk:
  • “If it fails, you learn that you’re not an entrepreneur and you come work at Vayner. You make less money, but you'll learn.” (17:14)
• On controlling your destiny:
  • “America is not the variable of happiness. You are the variable of happiness...” (35:36)
• On chronic illness and hustle culture:
  • “You can't hustle 18 hours a day, 365 days a year. You just can't. ... Give yourself grace.” (36:53)
• On new opportunities:
  • “Live social shopping is the biggest opportunity in the world right now.” (26:03)
• On deepfake anxiety:
  • “You can lawyer up or you can take a surfboard and ride it.” (41:18)

Timestamps for Important Segments

• (00:21 - 01:50): Gary on why LinkedIn content is the modern job search.
• (02:50 - 03:44): Deciding passion vs. business & marketing’s centrality to success.
• (05:29 - 08:50): Job misery, practicality vs. quitting, “Complainer City USA.”
• (09:34 - 17:49): Jake’s dilemma: when to quit a job for a growing side business.
• (18:15 - 19:10): Starting out as a broke and inexperienced content creator.
• (21:08 - 24:29): Building a personal brand and business as a psychologist; “platforms, algorithms, culture.”
• (25:31 - 27:02): The 70-year-old asking about AI/earnings and Gary’s live social shopping thesis.
• (29:13 - 29:52): Salvatore's mom and encouraging real hands-on learning.
• (31:08 - 35:36): The Immigration Answer Show segment—Gary’s advice for immigrant wellbeing.
• (36:53 - 38:12): Advice on entrepreneurship with chronic illness; giving yourself grace.
• (41:07 - 42:40): Deepfakes: embracing technological changes to build your brand.

Summary Takeaways

• Proactive digital presence (especially on LinkedIn) is essential in a shifting job market.
• No one is coming to save you: marketing/social is offense, and you need to play to win.
• Grace—not guilt—is necessary when circumstances (health, loss, adversity) slow you down.
• Start messy; don’t let insecurity delay you from creating and sharing content.
• Leverage current trends (like live social shopping) for entrepreneurial upside, no matter your age.
• Embrace technological shifts (even scary ones like deepfakes) to stay relevant.
• Happiness and success ultimately stem from your choices and perspective more than outside conditions.

Gary’s mix of direct challenge and empathetic support makes this an essential listen for anyone navigating career disruption, side hustles, self-doubt, or a rapidly changing digital economy.