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

Jun 3, 2025

Discover the transformative impact of a $50,000 investment in professional development with insights from Gary Vee's team. Learn a powerful three-part framework to evaluate business investments: understanding unique offerings, the significance of networking, and the influence of proximity to successful individuals. Hear firsthand experiences on how leadership qualities and small gestures can lead to greater success. If you're in the early stages of your entrepreneurial journey, this conversation encourages persistence and bold decision-making.

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ADVICE

Highlight Differences for ROI

Before investing in a program, highlight how it differs from past experiences.
Ensure every investment offers at least one new learning or positive ROI.

ANECDOTE

Paid to Save $100K

Jasmine spent $15,000 consulting a SaaS expert who advised against a feature development.
This avoided an estimated $100,000 expense, proving the value of costly advice.

ADVICE

Prioritize Access to Networks

Consider how much access a program provides to valuable people and networks.
Seek programs offering warm introductions to amplify your growth.

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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

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

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