What Joining My First Mastermind Taught Me (and Why It Changed Everything)

Have you ever looked around a room full of successful entrepreneurs and thought, “I don’t belong here”?

That moment hit hard the first time I considered joining a mastermind — and saw the $25,000 price tag.

In this episode, I’m sharing the raw truth of investing in my very first mastermind: the doubts, the imposter syndrome, and the terrifying leap that turned into a $255,000 launch just six months later.

At the time, I had never invested in peer coaching or business education. I had built my company solo — no courses, no mentors, no community. But I knew something had to change.

What happened next challenged everything: my beliefs about money, my mindset around growth, and what’s actually possible when you're the least experienced person in the room.

If you've ever questioned whether masterminds are worth it, felt intimidated in high-level rooms, or wondered if you're ready to invest in yourself… this episode is your permission slip.

You're not underqualified. You’re just getting started.

Click play to hear all of this and:

[00:40] The definition of a mastermind — and how it reframes business growth

[02:02] Feeling under-qualified to join a high-level room of entrepreneurs

[03:32] The initial shock of a $25,000 price tag — and the debate that followed

[04:41] A simple mindset shift: What if the investment could be earned back?

[05:56] How proximity to brilliant minds led to a $255K launch in six months

[07:30] How cultural and financial background influences risk-taking in business

[08:25] The unexpected benefits of being the least experienced in the room

🎧 Listen to the full episode, How a Mastermind Changed the Trajectory of My Business (and how it can do the same for you): Part 1, >>HERE<<

Listen to Related Episodes:

• 5 Mindset Shifts for Business Growth
• How I Maximize My Experiences and Investments to Reach My Next Level as a CEO
• How a Mastermind Changed the Trajectory of My Business (and how it can do the same for you): Part 2

Are you a 7-figure business owner ready to create a powerful brand, learn high-level marketing strategies, and build systems that scale alongside a group of talented 7-figure entrepreneurs? Then you must click >>HERE<< to check out my mastermind and add your name to the waitlist to be first to know when applications open up.

For full show notes, visit jasminestar.com/podcast/episode624

Transcript

Rosy Shephard 00:00:00  Hey there and welcome back to the Jasmine Start show. You're about to hear a special repurposed episode pulled from one of our most powerful conversations to date. One more Jasmine gets real about a pivotal moment in her entrepreneurial journey, investing in her very first mastermind. She shares what it was like to be the most underqualified person in the room. Her words, not ours. The mindset shift that helped her make a $25,000 investment, and how it ultimately turned into a $255,000 launch. If you've ever wondered whether masterminds are worth the investment, or if you felt intimidated by rooms full of bigger business owners, this episode is for you. Let's dive in.

Jasmine Star 00:00:40  I had never heard of the word mastermind, but when I learned its definition, I knew I had to be part of one. So I first heard the definition of a mastermind by a gentleman by the name of James Wedmore, and this is his quote. A mastermind is the amplification of like minded people coming together for a similar purpose. It's the notion that the sum is greater than the parts.

Jasmine Star 00:01:03  That one plus one plus one doesn't equal three. Eight equals 30. This happens when you surround yourself with other smart people and begin the process of peer coaching. End quote. Okay, so you know your girls in the hood, you know your goal is simple. So in short, what I read as part of this is that a mastermind is an opportunity to get around in an environment that allows your dreams to foster, and then get a clear plan of action to bring it to life. And so it was a blog post that I had come across, and then I started digging into what a mastermind was, who was going to them, what type of people found them interesting. And then I started digging into their websites, their blogs, their social. And I realized that this was a different caliber of a business person, that by 2015, I had been met with plenty of success. It was great, but I knew there was something more. What that was, I had no idea, but I knew that there was something more.

Jasmine Star 00:02:02  So in 2015, I was a small business owner with a partner and one employee. I wasn't even sure I was ready. Like, I wasn't even sure I was qualified for the master ride, but let's not even go there. Okay, so I wasn't sure that I was ready. I was qualified, and beyond that I wasn't even sure I was ready to invest. So why don't you hand me your cup and your saucer? Because I'm about to pour some tea. I'm about to get very transparent with you. I have not mentioned this outside publicly, but here on the podcast, I feel like I could go deeper with people and be 100% myself 100% of the time. So I started my first business in 2006, and by the time I considered a mastermind a full nine years later, I hadn't ever, not once invested in peer coaching or an online course. I had built my business entirely alone, and it was lonely. And I've spoken about that before, but I really want to hone in and where I was doing it entirely alone and not having a barometer of could I be doing this different? Could I be doing this better? So looking back, I wasted almost a decade of business growth opportunities by not investing in education, by, you know, not realizing that there is a different path or a different track that I could take that actually could be giving me more than I was doing on my own.

Jasmine Star 00:03:32  So when I applied in, I was accepted to my first mastermind. I debated investing because it was far more than I was comfortable with. I mean, the price tag, quite literally. It made my eyes twitch when I read the price tag. Initially, I turned to my husband and my business partner and I was like, oh, I think there's a typo. You see, they actually added an extra zero. This must be wrong. But it wasn't. So after debating with myself, you know, because like myself was the only person in this like decision making process because I was like, are you going to be all in? I came to the following conclusion if I learned one new way to grow my business. I mean, let's just be real. If I weren't learned one new way to make more money in the mastermind, it would pay back what I invested. You know, oftentimes people were like, oh, you know, there's this decision making process that I go to, and I weigh the pros and cons and like, how do I make this the simplest decision as possible? And I asked myself, do you think that you have the capacity to do something as part of this mastermind that would empower you to pay back the mastermind in the answer that I thought back then was yes.

Jasmine Star 00:04:41  So with that, I set my mind to building a revenue stream that made $25,000. Yeah, that was the cost of the mastermind. And that number is not a big number. It's a huge number. And that was for somebody who had never invested in their business in any type of education. It was so far out of reach. It was so bigger than my mind had ever thought. I was just like, this scares me beyond all measure. And so I was like, okay, can I do this? So the answer became within six months I created a new project and I launched it, but it didn't earn $25,000. It earned $255,000. Yeah. $255,000. And we yielded that after six months of work. But a one week cart opened. Being surrounded by brilliant people in the mastermind, it challenged my beliefs. It forced me to work in new ways. It cleared a path for me to create something new in an entirely new way. So I want to go back and offer a little bit of insight as to where I was at this time in my career.

Jasmine Star 00:05:56  So my husband and I, we are living in Orange County at this point in time, and money for us has always been this interesting thing in our lives. We are both children of immigrants. We hail from Mexican American families. My husband's mom is Chinese, his father is Mexican, but his mom was raised in Mexico. My mom was Puerto Rican, my dad is Mexican, and all of our families, like they came here and they worked very, very, very hard and they did the best they could. But it is not in any way, shape or form a way that you would look back in life and be like, well, they had a little extras for vacation, you know, it's like family dinners were like, kids get in the car. We're going big tonight. We're not going to Mickey D's. We're going to Carl's Jr, to which we would all be like, can we get a.

Jasmine Star 00:06:50  Western bacon burger?

Jasmine Star 00:06:52  No, no, of course, of course. You can't get that.

Jasmine Star 00:06:54  You're gonna get a cheeseburger. Of course you're not going to get the bacon. Who has money for the bacon? So for us, having a successful business was really a massive change in our lives and in our families. It was we were doing things that a lot of our families did not understand. They were in full support of, but they really didn't quite understand everything. And so when it came time for us to actually grow our business. JD and I did our best, but we were really depending on what we can source from the internet. We were not around other people who were doing what we wanted to do in bigger, newer, different ways. So I flew to San Francisco, which is where the first mastermind had met, and we stayed in this hotel called the Clift Hotel. At the time, it was like really brand new, swanky. It was right down in downtown, and I remember walking in and in the lobby, they had these massive oversized chairs and tables. And when I say like oversized, I don't mean like oversized for a seven foot person.

Jasmine Star 00:07:58  I mean, it's like oversized for like a 40 foot person. And so it feels like you're walking almost into a museum and they have these really cool elevators. And I went up to my room, I didn't know anybody and went down this bright purple hallway. And I went into my room and I laid on this bed and I thought to myself, you just made the biggest mistake. Like, what are you doing? You have no idea what you're doing. Then I talk to myself, you know. Out of that negative talk and went to the penthouse. And there I met 20 other entrepreneurs. And let me tell you everything I thought on that bed. Oh, it was right. I was so out of my league. I walked into this room and I realized that they could have been speaking Japanese. I had no idea what they were saying. And this is not for a sake of, like, exaggeration. No, quite literally, I had no idea. Like, I understand these words are English, but the way that you're putting them all together, I don't know what any of this means.

Jasmine Star 00:09:03  I don't know about forecasting. I don't know about funnels. I don't know about cost per leads or earnings per leads. I don't know about setting budgets. I don't know about funnels. What is a webinar? What is an email sequence? What's an email provider? What what what. All of these things. And they were just talking about retargeting and their strategies. And I'm like, oh girl, is it too late to get a refund? Like, I'm not lying. I was quiet. I am pretty sure that on the first day of a two day mastermind, I didn't say a single word. I'm pretty sure people were like, I don't think that girl talks. And I've always been raised to believe that it is better to keep your mouth shut and be presumed a fool, than to open your mouth and confirm it. Okay, so I was just scribbling notes like what is EPL? What is a funnel? Figure out how to do a webinar. Like literally I knew nothing and so half of me was like, I am in so far over my head, you got to get out.

Jasmine Star 00:10:09  You are wildly uncomfortable blaring alarm signals. You feel unsafe, go back to safety. And so in the break, because at the end of a very long day, you take like an hour break before you go out to dinner. I went up to the hotel room and I called my husband and I told him, like, very much like an eight year old at summer camp, like, I want to go home. Like, please let me go home. Like I'm going to.

Jasmine Star 00:10:35  Change my ticket. I need to go home.

Jasmine Star 00:10:36  And very wise of JD, he said, well, just finish the weekend. You're already there. So if you assume that you're not going to get anything or learn anything or say anything, that's fine, but just finish it. So I did, but I didn't do that before, just scribbling down in my journal how I was thinking and feeling and my greatest concerns. And it was in the process of journaling that I wrote everything down. And then I went back and I said, do you think you have the capacity to figure out all the things you don't know? And the answer was yes.

Jasmine Star 00:11:14  I didn't think it was going to be easy, but the answer was yes. And so with that, I went to dinner that night. I got to meet really brilliant people. And then the next day, instead of going into the room being like, I don't know, I don't know.

Jasmine Star 00:11:29  This is so hard. I'm frustrated. I'm alone, I'm scared.

Jasmine Star 00:11:31  I feel like I'm failing. I feel like I'm drowning in a sea of a knowingness. I simply just started writing a bunch of things that I had to figure out, and that was the safety net. That was the boy that was the lifesaver was, I don't know any of this, but I think I could figure it out and like, lo and behold, Google became my best friend. So when I said that I wanted to create a revenue stream that yielded, that brought in $25,000, that was the amount that I had spent on the mastermind. And then it ended up six months later, earning $255,000. That was on the back of I don't know what I'm doing.

Jasmine Star 00:12:18  I believe I can figure it out. And then I tried it. But here's the crazy thing. When you are surrounded by people who challenge your beliefs. When you're surrounded by people who forced you to work in new ways because you're like, oh, my old ways got me here, the new ways will get me there. And then these people really cleared a path for me to create something entirely new in my business. It opened my eyes not just to $225,000, but I launched that same project again four months later, and it earned $325,000. So maybe you come from a family where that is acceptable, normal, given, expected. But I have to tell you that in the matter of less than a year for somebody to make that amount of money, it was life changing. I didn't even dream that big. In 2015, I realized the difference in what I had a business online to what? I was building an online business. Oh, so what's the difference? I'm so glad you asked. Okay, so I had built a personal brand and I had built a business online, but I realized that I was the one who was trading dollars for hours in the mastermind.

Jasmine Star 00:13:46  I learned that an online business is set up. So you have a system in place that work for you, and they scale over time. This meant less of my time and more revenue.

Rosy Shephard 00:13:58  If that didn't light a fire under you, I don't know what will. That first mastermind wasn't just a financial leap. It was a mindset shift that set the foundation for everything Jasmine would go on to build in her business, and it's proof that sometimes the biggest breakthroughs happen outside your comfort zone. And if this episode spoke to you, we'd love for you to share it with a friend or leave a review letting us know what resonated most. And if you're curious about how Jasmine helped seven figure founders grow and scale their businesses today, check out the links in the show notes to learn more.