Why Most People Never Quit Their Job & Start Their Business (and How To Finally Do It)
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this episode of Tea with Gary Vee, Gary addresses viewers' questions about overcoming trauma, business growth strategies, and entrepreneurial decision-making. (01:47) The standout moment features Paul from West Texas, who built a garage cleanout business earning $699 per job in just one month. (33:56) Gary challenges Paul to quit his marketing director job and pursue his successful business full-time, revealing that Paul's fear of failure stems from a previous business loss during COVID-19. (45:26) Throughout the episode, Gary emphasizes the importance of taking action over consuming negative content, networking through direct outreach, and recognizing when you're a "winner putting on loser makeup."
- Core Theme: Overcoming fear and self-doubt to pursue proven business opportunities, while addressing the psychological barriers that prevent entrepreneurs from scaling successful ventures.
Speakers
Gary Vaynerchuk (Gary Vee)
Entrepreneur, investor, and CEO of VaynerMedia, a digital marketing agency. Gary built his family's wine business from $3 million to $60 million through early adoption of e-commerce and video content. He's also the founder of VeeFriends, an NFT project, and serves as an advisor and investor in numerous startups including Stan Store.
Paul Garza
34-year-old marketing director from West Texas who recently launched a garage cleanout and resale business. Previously ran a marketing agency that served oilfield companies before COVID-19 impacted the industry. Father of three children and demonstrates strong marketing skills through successful Facebook advertising for his new venture.
Key Takeaways
Stop Consuming Negativity to Overcome Trauma
Gary emphasizes that people struggling with trauma don't always need expensive therapy - they need to change their information diet. (02:18) He argues that consuming optimistic, practical content while exercising and changing social circles can be as effective as professional help. The key insight is learning to separate external negativity from personal worth - understanding that abuse or mistreatment reflects the perpetrator, not the victim. This approach requires actively choosing positive content over fear-based media that keeps people "locked" in cycles of anxiety.
Volume and Form Matter More Than Perfect Strategy
Using the analogy of physical fitness, Gary explains that business success requires both massive volume of action and proper execution form. (10:50) He describes doing 25 employees worth of content testing daily, contrasting this with people who post "one on their grid every four days because they aesthetically want it to look good." The photographer guest learned that sending 3-4,000 LinkedIn messages to marketing executives is necessary, not just six Instagram DMs. Success demands uncomfortable levels of outreach combined with personalized, relationship-building approaches rather than immediate sales pitches.
Humility Is a Secret Competitive Weapon
Gary identifies humility as "an incredibly rare weapon of choice these days" when discussing the photographer's reluctance to appear on small podcasts. (16:30) He explains that the person who breaks out from their peer group is often the one willing to take judgment from others while doing things others consider "beneath them." This principle applies to taking small speaking opportunities, meeting with interns who may become future executives, and being willing to "get some dirt under those pretty fingernails" rather than waiting for opportunities to come to you.
Recognize When You're a Winner in Loser's Clothing
Paul's story reveals how successful people can sabotage themselves by imposing artificial limitations based on past failures. (49:18) Despite earning $699 per garage cleanout job with 16 successful completions in one month, Paul remained in his marketing job due to fear from a COVID-19 business failure. Gary's "common sense game" demonstrated that Paul was "the best version of a loser" - a capable winner wearing "loser makeup." This happens when people give more weight to past failures than current proven success, often using family or security as excuses for their own fear.
Create Security Through Action, Not Avoidance
Rather than staying in comfortable positions out of fear, Gary advocates creating security through strategic action. (40:26) For Paul, this meant front-loading bookings through aggressive advertising to create a pipeline of guaranteed work before leaving his job. Gary also pointed out that Paul could always find another marketing job if his business failed, and that his previous experience overcoming business failure actually made him more qualified, not less. True security comes from proving your capabilities and creating multiple pathways forward, not from clinging to single sources of income.
Statistics & Facts
- Paul earned $699 per garage cleanout job and completed 16 jobs in just one month of operation with no competition in his West Texas market area. (35:52)
- Gary mentioned having 25 employees dedicated to content testing and posting throughout the day, demonstrating the volume required for effective social media marketing. (11:18)
- Gary stated he has taken 40,000 business meetings over his career, with only 137 leading to meaningful business relationships, highlighting the importance of volume in networking. (21:15)
