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.
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