In 'Crush It!', Gary Vaynerchuk shows readers how to harness the power of the Internet to make their entrepreneurial dreams come true. The book focuses on utilizing new, free tools on the Internet to capitalize on branding and developing a business. Gary shares his own experiences, from building his family's wine shop into a national industry leader to transforming his life and earning potential by building his personal brand. The book emphasizes the importance of identifying and pursuing your passions, using social media effectively, and maintaining a hardworking and authentic approach to business.
#AskGaryVee is a book that compiles questions and answers from Gary Vaynerchuk's YouTube show of the same name. It provides practical advice on marketing, social media, entrepreneurship, and leadership, drawing from Vaynerchuk's experiences as a successful entrepreneur. The book covers a wide range of topics, including work-life balance, personal branding, and effective use of digital platforms.
In 'The Thank You Economy,' Gary Vaynerchuk explores the evolution of today's marketplace, emphasizing the importance of social interactions and customer care in building successful businesses. The book highlights how companies can scale personal, one-on-one attention to their entire customer base using social media platforms. Vaynerchuk argues that businesses must shift their culture to be more customer-aware and fan-friendly, leveraging word-of-mouth power to drive growth and profit. The book is filled with real-world examples and data-driven evidence, making it a valuable resource for business owners and managers looking to adapt to the new business era.
A Note from James:
So I’ve been doing this podcast for a long time—over 1500 episodes—and I’ve spoken to everyone from billionaires to best-selling authors, athletes to entrepreneurs. But there are a handful of episodes that still ring in my ears years later. One of them was Episode 156 with Gary Vaynerchuk.
I was just re-listening to it while pulling together notes for a potential book, and I realized this conversation is timeless. It’s not about hype. It’s about freedom. Gary’s blueprint—learn, build, create community, stay self-aware—is the real deal. No shortcuts. No tricks. Just pure, actionable wisdom. Whether you’re 23 or 53, if you're serious about building the life you want, this one’s worth a listen.
Send it to your kids. Your friends. Your future self.
Thanks again for listening.
Episode Description:
In this re-release of one of the most downloaded episodes of The James Altucher Show, James sits down with Gary Vaynerchuk just before the release of his book #AskGaryVee. What unfolds is a candid, highly tactical conversation about business, content creation, self-awareness, and the true meaning of entrepreneurship.
Gary breaks down his framework for success—from selling wine via YouTube in the early 2000s to launching VaynerMedia and investing in Facebook, Twitter, and Tumblr. He also explains why patience, practicality, and micro-failure are essential ingredients for long-term freedom.
This isn’t motivational fluff. It’s the strategy, mindset, and playbook of someone who’s been in the trenches—and is still hungry.
What You’ll Learn:
- Why "entrepreneurship" is really just a path to freedom—not fast cash
- How Gary made (and learned from) multiple startup failures in 2009
- Why content marketing is about sincerity, not SEO hacks
- How to test new business ideas through arbitrage—like flipping Jets gear on Amazon
- A tactical breakdown of self-awareness (and how to get it from people you trust)
Timestamped Chapters:
- [00:00] Leisure vs. Freedom: What You’re Really Trading
- [01:00] Recommending Competitors as a Sales Tactic
- [03:00] Early YouTube, Wine Library, and ROI Before Social Was “Social”
- [06:00] Entrepreneurship vs. Lifestyle Marketing
- [08:00] Ego, Confidence, and What Scares Gary Vee
- [10:00] The Trainwreck Year: 2009 and Four Failed Startups
- [12:00] Experiments, Micro-Failures, and Million-Dollar Misses
- [14:00] Offense vs. Defense in Business
- [15:00] Building Trust Through Sincerity in Content
- [18:00] Self-Awareness: Gary’s Most Important Entrepreneurial Trait
- [22:00] The Real Numbers: What It Means to Be in the 1%
- [25:00] Leisure Costs More Than You Think
- [29:00] Why Gary Loves Losing and Chasing More Than Winning
- [34:00] The Self-Awareness Dinner Party Hack
- [38:00] Redefining Success: From $213K to $87K and Happy
- [42:00] Clouds and Dirt: Finding Your North Star and Executing in the Weeds
- [43:00] The Arbitrage Blueprint: eBay to Amazon
- [47:00] Community Building Through Twitter and Micro-Engagement
- [49:00] Jab, Jab, Jab, Right Hook (And What People Get Wrong About It)
- [52:00] Avoiding Negative Energy in Business and Relationships
- [54:00] Tactical Social Media Growth: Commenting, Listening, Engaging
- [56:00] Scaling Beyond Arbitrage: Events, Podcasts, Products
Additional Resources:
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