I asked Gary Vaynerchuk when he last cried.

He said funerals. And once, in 1998, when the Jets lost a heartbreaker in overtime.

That’s it.

No tears over business failures. No existential breakdowns over missed opportunities. Just the Jets.

Gary came back on my podcast to talk about freedom. Not Ferraris or 8-figure exits.

Real freedom.

Like picking your kid up from school at 3 p.m. without asking permission. Like never again attending a meeting about toothpaste brand engagement.

He believes entrepreneurship is just that—freedom. And that most people are too soft to earn it. Not because they can’t. Because they won’t give up leisure.

They won’t skip Netflix or poker night. They want freedom without sacrifice.

A cheat code. A blueprint without bruises.

He talks about practicality like it’s a religion. Forget trying to be the next Zuckerberg.

Build a mustard brand. Sell niche t-shirts on Ebay. Make $88K doing something weird and personal. That’s not failure. That’s winning on your own terms.

Not Money. Not Fame.

I distilled Gary’s method into four steps.

He didn’t lay them out this way, but they were behind everything we talked about:

1. Learn something real. Not “read three Medium posts.” Actually do something for 5–10 years.

2. Document the journey. Use content to become a lighthouse. People like lighthouses.

3. Build community. Talk to every follower like they’re your only follower. At least until you can’t.

4. Ask them to do something. Buy the shirt. Share the post. Come to the con. Vote. Whatever.

Most people get it backwards. They start with the pitch.

Gary starts with the “dirt.”

The daily work. The eBay listings. The DMs. The comments. The boring stuff that builds trust. It’s what most people avoid. Because it doesn’t feel like winning.

Until it is.

Gary didn’t start by selling. He started by talking. About wine. About the Jets. About flipping Pokémon cards. The selling came later. After the trust.

Too many people want to be rich without being useful.

They sell courses about selling courses. They fake lifestyles they never lived. And when it all falls apart, they blame the game instead of the mirror.

He said something else that stuck with me. If you’re not actively trying to put yourself out of business, you’re playing defense.

Amazon arbitrage will die. So will content platforms. So will the fads. So will your current edge. So be early to the next thing. Always.

We talked about patience. About the fantasy of the 1% and the reality that $400K a year puts you in it. We talked about side hustles built after work. About how he used to record Wine Library TV from 7 p.m. to 2 a.m. while still working full-time.

We ended where we started: with freedom.

Not money. Not fame.

Freedom.

To live how you want. To never ask permission again.

To cry only when it really matters.

Thanks, Gary.

Click here for the full conversation.

If you know anything about Gary, you know you’ll be motivated by the end.