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? 😳 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’s team. It was a big leap, a big number, and (spoiler alert!) a BIG shift in how I approach business investments.

If you're wondering whether investing in your growth is worth it, I’m sharing the 3-part framework I use before I spend a dime:

1️⃣ Highlight the Differences: Why every investment must teach me something new.

2️⃣ Access Matters: How the right room can change your life.

3️⃣ Proximity is Power: Why being near greatness accelerates success.

Plus, you’ll hear what I learned from watching Gary Vee behind the scenes, how small gestures reveal leadership, and why “hi” can be a secret business superpower.

Whether you're spending $500 or $50,000, this episode will help you make bolder, smarter investments.

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, consider this your loving nudge. ❤️

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

Listen to Related Episodes or Links Mentioned:

• Nonverbal Communication Secrets That Drive Sales and Build Trust with Blake Eastman
• How to Reclaim Your Time and Boost Business Productivity with Nick Sonnenberg
• My 1-1 Call with Gary Vaynerchuck

📧 Join my Newsletter for a weekly cocktail of insider business strategy, personal reflections, and the journey of being a thought leader. 📧

Click >>PLAY<< to listen now!

For full show notes, visit jasminestar.com/podcast/episode549