Inside My $50K Investment with Gary Vee’s Team: How I Make Smart Business Investments

Have you ever sat through a sales pitch thinking you knew what was coming… only to be hit with a $50,000 price tag? 😳 Yeah, SAME.

In this episode, I’m pulling back the curtain on one of the biggest financial decisions I made this year: investing in a professional development program with Gary Vaynerchuk and his team. It was a big leap, a big number, and (spoiler alert!) a BIG shift in how I approach business investments moving forward.

If you're trying to figure out whether investing in your personal or professional growth is worth it, I'm breaking down the exact 3-part framework I use before I spend a dime:

1️⃣ Highlight the Differences: Why every investment needs to teach me something new to be worth it.

2️⃣ Access Matters: How being in the right room can change your life (and how to get those warm intros that open doors).

3️⃣ Proximity is Power: Why simply being near greatness can accelerate your success more than you think.

You'll also hear what I learned watching Gary Vee move behind the scenes (like, literally sitting back and studying his team in action 👀), how small gestures reveal big leadership lessons, and why saying “hi” can be a secret superpower in business.

Whether you're spending $500 or $50,000 on your growth, this episode will help you make smarter, bolder, and more strategic decisions to get the most out of every dollar.

Friend, if you’re in the “digging phase”—building, dreaming, working before anyone sees it—this is your sign: Keep digging. Keep growing. Your skyscraper moment is coming.

And if you haven't left a review for the show yet, consider this your loving nudge across the internet. It would mean the world. ❤️

Click >>PLAY<< to hear all of this and:

[00:45] Why a $50,000 pitch almost scared me off—and why I leaned in instead

[01:47] The #1 question I ask before making ANY investment

[03:40] How objective-setting and leadership assessments changed my mind

[04:31] Why ACCESS (and warm introductions) are more valuable than any brochure

[06:29] How PROXIMITY alone can change your business trajectory

[08:10] Watching Gary Vee move behind the scenes—and what I learned

[12:17] The biggest leadership lesson I learned from Gary in just 20 seconds

[13:55] My full 3-step framework for making smart, strategic investments

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