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

3 Jun 2025 · 15 min

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The Jasmine Star Show: Episode Summary

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

Episode Description In this episode, Jasmine Star discusses her significant investment in a professional development program with Gary Vaynerchuk’s team, totaling $50,000. She shares her decision-making process, a three-part framework for evaluating investments, and insights gained from observing Gary Vee in action.

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Key Themes

  1. Investment Decision-Making

Jasmine reveals her three-part framework for making strategic decisions regarding investments:

  • Highlight the Differences: Assess what new knowledge or skills will be gained and how they differ from past experiences.
  • Access Matters: Evaluate the networking opportunities and warm introductions that come with the investment.
  • Proximity is Power: Understand the value of being close to influential people and organizations for personal and professional growth.
  1. Personal Growth Through Investments
  2. Jasmine emphasizes the importance of learning something new from every investment. Even small insights can lead to significant transformations in business practices.
  3. She shares a personal experience where spending $15,000 to consult an expert saved her over $100,000 by preventing a poor investment decision.
  1. Networking and Access
  2. The podcast stresses the value of access to industry leaders. Jasmine highlights how warm introductions can lead to opportunities that reshape one's business trajectory.
  3. She provides examples of networking successes that stemmed from her investments.
  1. Proximity to Greatness
  2. Discussing her experiences with Gary Vaynerchuk, Jasmine notes the importance of observing successful individuals’ behaviors and strategies in real-time.
  3. She describes her approach to learning through proximity, emphasizing 'energetic osmosis'—the idea that being around successful people positively influences one’s mindset and strategies.
  1. Leadership Insights
  2. Jasmine shares a pivotal lesson learned from Gary Vee about the simplicity and power of a personal greeting. Acknowledging and connecting with people can build meaningful relationships.

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Episode Highlights

  • Initial Investment Reaction: Jasmine recounts her surprise at the $50,000 price tag during the sales pitch.
  • Investment Framework: Each part of her framework is explored in detail, demonstrating how she applies it to her investment decisions.
  • Observational Learning: Jasmine illustrates how watching Gary interact with his team and the way he conducts business offered invaluable lessons in leadership and professionalism.

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Takeaways

  • Framework for Smart Investments: Use Jasmine's three-part evaluation to determine if an investment aligns with your growth goals.
  • Importance of Learning: Focus on the potential for growth with each investment, remembering that even a single insight can change the course of your business.
  • Networking as a Key Resource: Seek opportunities that provide access to influential networks for future collaborations and learning.
  • Value of Proximity: Strive to be near individuals who inspire and challenge you, as their influence can significantly affect your success.

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Call to Action Jasmine encourages listeners to reflect on their investment choices and to apply her framework as a guideline for future decisions. She also invites feedback through podcast reviews, emphasizing their importance to the show’s impact.

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For more insights and to listen to the episode, visit [The Jasmine Star Show](https://podcasts.apple.com/us/podcast/the-jasmine-star-show/id1479619320).

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Transcript

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0:00If you've been feeling stuck in your business and wondering if you're the reason it's not growing faster, I have something for you. I'm hosting a free, no-pitch, live class called Three Money Beliefs That Made Me Millions. And I'm sharing the exact mindset shifts that helped me go from million-dollar years to million-dollar months. This isn't fluff. It is a surprising strategy that changed everything for me, and I want to share it with you. Like I said, no pitch, no fluff, just you and me talking about how we shift our beliefs around money to make you millions. Save your seat now at jasminestar.com forward slash millions.

0:32I can't wait to see you there. I think that proximity, me watching and seeing what they're doing, is a massive game changer. The closer that I can get to the person or the organization, the more I learn. Okay, imagine this. You're sitting on what you know to be a pitch. They're pitching you. And you think to yourself, I can't prepare for the pitch. I'm ready for the pitch. I'm very well aware of how one pitches and how one receives a pitch. No, we're not talking about baseball. We're talking about business. Welcome to the Jasmine Starr Show. Today, we're going to be talking about the considerations that I factor in when it comes to making a financial decision and investment for personal and or business development.

1:11So let's go back to this pitch. I am sitting there on a call. We're on Zoom. And I'm expecting that I'm going to be pitched as part of a professional development program offered by way of Gary Vaynerchuk and VaynerMedia. And I think I'm going to know how much this is going to be. So just imagine my surprise when they go through this beautiful, amazing, like basically glorious layup of a business offer. And then I ask, well, how much? And then they respond,$50 ,000 for four months. And I was like, I was not ready for that. I wasn't ready for that. And so if that number is a little bit big to you, or maybe you are at a point in your business journey where you're trying to decide what do I actually invest in, I'm going to walk you through my three-part framework of how I make financial considerations for the things that I invest in.

1:58Number one, whenever I am presented with an offer, I want to go through and I immediately start highlighting the differences. I am not afraid to invest in personal or professional development. I'm not afraid of it. I just need to know that when I'm going to spend money and when I'm going to spend a lot of money, I want to know how different it is from things I've done in the past. So I want to make sure that everything I do has a positive ROI, my return on investment. And I'm very proud to say that everything I've invested in, I've got a positive ROI. Maybe not in traditional sense. I remember I spent, I know this is kind of crazy, but it was worth it to me.

2:31I spent$15 ,000 to spend a day with somebody who helps build SaaS businesses. And so I spent$15 ,000 with him to pressure test this idea that I had in expansions and feature sets. And he said, actually, I don't even think that you should do that because this is how much I actually think it's going to cost you. So we didn't move forward with this feature set development. And so I paid$15 ,000 for somebody to tell me not to do something. But at the end of the day, I think I probably saved well over$100 ,000 not making that decision. So is that a positive ROI? In my book, yeah. I saved a lot of money.

3:04So it's just the terms in which I decide my investments and say, highlight the differences. And can I make sure that there's going to be a positive ROI? I want to make sure that I am learning one new thing from every time I make an investment. Now, for some people, which I totally get in respect, learning one thing is not enough. In my mind, if I learn one thing, it could actually transform the entirety of my business. And my goal after every time I invest in something, however the meetings unfold, is it coaching, is it a group meeting, is it an event, whatever it is, I just wanna make sure that I walk away that I'm 1 % better.

3:38So the first thing that I'm considering is highlighting the differences. How is this different than anything else that I've done? So when I am using this criteria, I'm gonna use this example that when I invested to learn from Gary Vaynerchuk and his team, I logically laid out how is this offer different than anything else that I have done I want to make sure that some of the things that they went through in their sales pitch was Objective setting right? They said you have to come in with a clear framework of what are your objectives through this program Any other program? It's crazy to say but any other program nobody has ever started off by saying What are your objectives and we want to make sure your objectives are in line with ours?

4:14That was immediately different The second biggest difference is they made you go through a leadership assessment I have never done a leadership assessment. I was very intimidated. They were asking these questions of how do you process conflict? How direct are you? And I thought to myself, okay, this is very different. So they wanted to identify my strengths and my weaknesses, and they wanted to give me a clear path to leadership performance increases and better feedback from the team. The third thing was executive coaching. Now, I have a business coach, and it's different than executive coaching, at least in my mind.

4:45I had never gone through a formal group program with executive coaching. So those three things, those three things, objective setting, the leadership assessment and executive group coaching, I had never done it that way. So that was immediate difference. So I was like, okay, part one of my framework, we're locked in. The second thing that I consider when it comes to making an investment for professional personal development is access. I'm at a point in my career where I want to expand my network and I want to do it strategically. And I'll be very clear as a brown girl, as a female founder, as somebody who's bootstrapped, I don't run in very traditional powerful circles so that if I have the opportunity to get access to a group of people, a think tank, anybody who's doing something pretty incredible in the world, that's weighted high for me on my personal schedule.

5:30So I want to network, but I actually don't know how this program was offering me access that I had wanted. Could this opportunity introduce me to meet other people and leaders that I would find interesting? So what happens is when I do programs like this, when I go to conferences or invest, I wanna always think in terms of, can I get warm introductions to people who are there in the room? Warm introductions. So every time I'm looking at a personal or professional development, I'm saying, can I get a warm introduction? So one of the breakdowns of this particular program was they had industry leaders come in and give like a weekly training.

6:04And so in my mind, I thought to myself, wow, for people who I'm learning from, I could get a warm introduction. So I wanna go through two examples of warm introductions that radically flipped my world upside down. First is a shout out to Blake Eastman. Blake Eastman came on my podcast to talk about nonverbal communication and leadership. We got so much great feedback from that podcast. I'll be sure to link it in the show notes. And then a second warm introduction I got was from Nick Sonnenberg. Nick Sonnenberg was also on the podcast and he was talking about creating systems and SOPs in your business.

6:35I'll be sure to link to his show in the show notes. I look at those introductions and then here's the beautiful thing. is the warm introduction from a program that I invested in turned into warm introductions from Nick and Blake to other people to be on the podcast. So when I'm looking at making an investment, I ask myself, how much access do I get and what could I do to maximize that access? The third thing that I'm looking for when it comes to professional or personal development is proximity. Now, I'm gonna be very clear. This is not for everybody. It is just a high marker for me. So for me, I want to be very close to the person or the organization who is running it.

7:16I think that proximity, me watching and seeing what they're doing is a massive game changer. The closer that I can get to the person or the organization, the more I learn. And here's the beautiful thing. I don't need one-on-one coaching through a program unless I was investing in it. If I'm investing in a group program, if I'm investing in a conference, no problem. I'm not going to get one-on-one. But proximity, how close could I see them? And so I think that there's this word that I like to use called energetic osmosis. Your energy will impact my energy. And when I'm around energy, I feel it differently.

7:46And that has a big impact over how I show up professionally. So I learn the most just by watching. So if I can just watch people or teams move, then I know that that proximity is going to be worth it. I don't think that I'm necessarily book smart. I think I'm street smart. So having been grown up, like on the streets, you could see human behavior and you could read between the lines. So part of this program was that I would get a 15 minute one-on-one call with Gary Vaynerchuk. That was super high value for me. Number one, because of proximity, but more than anything, if I knew that we were gonna get one-on-one time with him and he was gonna be going to a few of our events, I would be able to look at him.

8:28And so you're all thinking like, what do you actually mean? No, no, no. I mean, just stare at him. I mean to watch how does he move in a room? How does somebody of that caliber work in a room, talk in a room and move in a room? Okay, so I wrote down a few things that I was like, you guys are gonna think that I'm next level scary. Listen, I'm just telling you like how I make investments is proximity and watching a person move. So I had that one-on-one call. I'm gonna link in the show notes how I had that one-on-one call with Gary and I'm gonna talk, I'll share it here on the episode. I shared it here on the podcast before, but it's worth a shout out so that you could see the behind the scenes of what that one-on-one call looked like and it's in the show notes.

9:02But I know that when I have the opportunity to get close to somebody, I really sprint towards that because all I need to do is just be close enough to watch how they move. Okay, so here's an example of how I watched him move. The very first in-person event was in New York City. He had just launched his book and it was at New York Stock Exchange that we got to ring in his book launch and it was like a big to-do and it was a lot of fun. And then the second day, he opened up his apartment building. They have like a lounge VIP area for guests to come in. And so he opened up his apartment building for us to go to his apartment building in New York City.

9:38And what we got to do there was go through sessions from his team teaching us. And then we got to have lunch with Gary and his fiance, Mona. But let me tell you, from an outsider's perspective, I don't, I think I maybe said hi. I think I said hi, Gary. I think I said two words to him the whole day. But I was able to see how big of a team does he travel with. So he's in his city. I counted how many people he rolls with that was important to me I saw his videographer and I saw what his videographer thought was important to be capturing Because if I ever get the opportunity to travel or work for the videographer in a roaming situation I want to be able to tell the videographer These are the things that are important and I don't want to have to think about what you're recording as long as you know So I was watching when did he pick up his camera?

10:19When was he rolling? What kind of b-roll was he getting was he recording ambient conversations? I was digesting all of this I saw how he treated staff He was very kind. He looked everybody in the eye and he said thank you profusely to every single person. I saw how his team strategically worked the event. So the team was there as part of the event. And then Gary enters the room and that changes the alchemy. I wanted to see like how is his team supporting him when he becomes the center focus of the room. I'm watching all of it. I was also watching like where did he sit? So we had two tables during the lunch.

10:54I wanted to see what table is he sitting at? Where is he sitting yet? Where is his team strategically placed? I noticed that his team sat all at different areas of the tables. And I'm going to share this part because it's a little bit creepy. I was sitting next to one of the organizers of the event and he was texting other team members on the team in real time. And he was saying, let's make sure that we prioritize one of the female founders asking a question. Like I saw his text message because what happens in sometimes groups like this is that sometimes guys have a tendency to jump in faster or be a little bit louder.

11:27So his team member was telling the other team members, hey, let's balance this out. Let's make sure that everybody has a turn, but let's make sure that we insert, let's call on a female founder next. You don't get that type of information without proximity. You don't get how a person's team, you don't get the behind the scenes propping up of somebody to do what it is they do and build in that capacity. So I saw how he highlighted his fiance. Mona was there with us and he was always saying really nice glowing things and incorporating her into the conversation as also as an entrepreneur. And he, I saw how he organized, we did one-on-one photos with him.

12:01I saw how him and his team navigated one-on-one photo, one-on-one photo, one-on-one photo. He got it really done fast. He was so kind, but then he made a quick exit. I liked seeing that stuff. I liked to see how very powerful, rich, and successful people move in the world by making people feel kind, supported. I wanted to see how his team showed up. I wanted to see the behind the scenes. All of that was proximity. And I think I probably said to him two words that day. So one of the things that was really important was the biggest takeaway was the leadership lessons that I learned. And one of the kindest leadership lessons that I learned is to always say hi.

12:41So at the last event that we were together as a group, it was something called VCon and it was in Los Angeles. And part of being at the group, we got an invitation to the meta party. So Metta hosted a party. It was on a rooftop in Hollywood. And I showed up at the event by myself. I hung out with a few people and I'm just an introvert. And so I ended up leaving early. So the group was hanging out. I was trying to slip out through the back. And one thing that I noticed was Gary was sitting in like a U-shaped booth. And his chief of staff saw me. And I look at the table. And I'm trying to sneak out through the back.

13:12The table was not even close to where the party was. It was a little bit close, a little bit far. And I make eye contact and I notice that it's Gary. And then I immediately like look away because I'm awkward. And he says, Jasmine, he gets up and his chief of staff come over and they just say hi. It was probably a 20 second exchange. And he said, are you having a good time? Are you good here? And I was like, yes, thank you so much. And then he went back and he sat down and continued the conversations. And I said goodbye to his chief of staff. And I thought to myself, a real leader just looks people in the eye and says hi.

13:41Doesn't make a career out of it. Doesn't use any excess words. All he simply says is, I see you. I appreciate you and you're moving on. So I want to make sure that if you know somebody who is making an investment in their personal or professional development, share this three-part framework with them. They might really appreciate it. So to recap, number one, in order for you to decide if you want to use this framework is number one, are there significant differences between anything else you've done in the past? If it's a yes, it's a yes. Number two, do you get access to networks or warm intros as part of it.

14:16If it's a yes, it's a yes for me. And the last and final thing is, do you get proximity to a person or a team that will have an impact and expedite how quickly you are advancing personally and professionally? If the answer is a yes, it's a yes. I want to say thank you so much for watching and listening to The Jasmine Star Show. And for those of you who leave a review, thank you. We read the reviews. They have a wild, wild impact on what it is we do. So if you haven't left a review, This is me looking at you across the internet and saying, don't let me down. I would love to hear and read one of your future reviews on the podcast soon.

14:49Thank you.

From the publisher

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:

📧 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

Join my free, no-pitch live class called 3 Money Beliefs That Made Me Millions, and I’m sharing the exact mindset shifts that helped me go from million-dollar years to million-dollar months.

Save your seat -> JasmineStar.com/millions


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