If You’re Scared to Ask for the Sale, Listen to This
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 dynamic TikTok Live session, entrepreneur Gary Vaynerchuk answers audience questions covering everything from family business dynamics to building personal brands and overcoming heartbreak. (00:59) Gary emphasizes that family time should always come before money in business relationships, warning that choosing ego and profit over family creates lasting tension. He tackles tough questions about entrepreneurship, revealing it's "much harder than you think" and shouldn't be romanticized by social media portrayals. (02:28) The session covers practical advice on social media content creation, local marketing strategies for service businesses, and breaking into competitive industries like sports media. Gary also discusses his upcoming 2025 plans to increase his content presence and continues building the VeeFriends universe.
- Main themes include prioritizing family relationships in business, the harsh realities of entrepreneurship, practical social media strategies, and the importance of asking for what you want without fear of rejection.
Speakers
Gary Vaynerchuk
Gary Vaynerchuk is a serial entrepreneur, five-time New York Times bestselling author, and CEO of VaynerMedia, a full-service advertising agency. He's also the creator of VeeFriends, an NFT and intellectual property company focused on meaningful collectibles and community building. Gary transformed his family's wine business from $3M to $60M through early adoption of social media marketing and has been a pioneer in the creator economy space since writing "Crush It!" in 2009.
Key Takeaways
Prioritize Family Time Over Money in Business
Gary emphasizes that in family businesses, the most important principle is putting family relationships above financial gain. (01:09) He states "Family time over everything" and explains that while working with family gives you meaningful time together, the biggest mistake is choosing money and ego over family relationships, which creates lasting tension. This principle applies whether you're working directly with family members or making business decisions that affect family time. Gary personally has no regrets about the time spent working with his father and brother AJ, viewing it as quality family time rather than just work.
Entrepreneurship is Harder Than Social Media Portrays
Gary delivers a reality check about entrepreneurship, stating "There's nothing harder than being an entrepreneur" and warning not to let social media fool you. (02:28) He shares a personal example of a 40-something entrepreneur with a remarkable, practical startup who recently went out of business, illustrating how even experienced, capable entrepreneurs can fail. This takeaway serves as both a warning for aspiring entrepreneurs to prepare mentally for the challenges and validation for current entrepreneurs struggling with difficulties - it really is as hard as it feels.
Use Local Social Media Marketing for Service Businesses
For service-based businesses like plumbing or auto repair, Gary recommends a specific social media strategy: create organic content showing your expertise, then amplify successful posts with targeted local advertising. (05:38) The strategy involves posting helpful content (like "here's what I do well" or "here's how you could avoid needing a mechanic"), identifying posts that get good organic engagement (5,000-10,000 views), then spending $100-500 to promote those posts within a 20-mile radius. This approach combines authentic expertise with strategic paid promotion to generate local leads cost-effectively.
Combat Analysis Paralysis with Decisive Action
When faced with multiple business ideas, Gary's advice is simple: "Roll the dice. Flip a coin. Throw a dart." (10:31) He compares people who say they have too many ideas to pick from to a scared sixth-grader making excuses to avoid asking someone out - they're using "too many options" as an excuse to avoid the risk of failure. Gary emphasizes that the fear of choosing wrong is actually preventing any progress at all. The key insight is that execution and learning matter more than perfect initial selection, and any action is better than paralysis.
Ask for What You Want Without Fear
Gary demonstrates comfort with asking for sales during the live stream, directly requesting that viewers who've been helped by his content purchase his $25 comic pack. (09:08) He explains this mirrors his confidence in business situations - he's comfortable asking for the sale, making requests, and putting himself out there because he's not scared of rejection. However, he admits this confidence didn't extend to personal situations in his youth, like asking girls out. The takeaway is that developing comfort with asking for what you want - whether in sales, business opportunities, or personal situations - is crucial for success.
Statistics & Facts
- Gary mentions that "literally 50% of dudes and 8% of women want to be in sports media on earth right now," illustrating the massive competition in that industry. (19:02)
- Gary reveals his high school GPA was 1.67 and he was ranked 243 out of 254 in his class, demonstrating that academic performance doesn't predict entrepreneurial success. (24:57)
- Gary states he's been "doing this for thirty years" when discussing building community and social media presence, emphasizing the long-term commitment required for success. (26:06)
