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 EastmanHow to Reclaim Your Time and Boost Business Productivity with Nick SonnenbergMy 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