Why the Best Entrepreneurs Keep Investing in Themselves

Have you ever looked at the price tag of a conference, mastermind, or coach and wondered, "Is it really worth it?" I’ve asked myself that same question every single time I’ve invested in my own growth.

In this episode, I’m sharing the biggest mindset shifts I took away from attending the Forward Conference—and why I believe the greatest return on investment isn’t the information you receive, but the person you become. From watching successful entrepreneurs think in real time to hearing honest insights from leaders who are still figuring things out, I was reminded that confidence isn’t built through certainty—it’s built through action.

If you've been waiting until you feel "ready" to make your next big move, this conversation might be exactly the perspective shift you need.

Things I Cover:

• Why the best entrepreneurs never stop investing in themselves
• The real ROI of conferences, masterminds, and coaching
• How confidence is built through action—not having all the answers
• Why the right room can change your business faster than another course
• The hidden power of proximity and surrounding yourself with high-level thinkers
• How investing in yourself transforms your identity as a leader
• The "Play Bigger Principle" that has shaped my growth for years
• A challenge to help you identify the room you've been avoiding—and why it may be the one you need most

If this episode encouraged you, share it with another entrepreneur who needs the reminder to bet on themselves. And if you're looking for a community that challenges you to grow, implement, and truly play bigger, I'd love to connect with you.

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Transcript

Watching how successful people think, watching how they solve problems, watching what's possible. And sometimes one conversation changes your trajectory more than an entire keynote. And that's why I continue to invest. Not because I need another notebook full of ideas, but because every time I put myself in a bigger room, I leave as a bigger leader.

How many times have you ever looked at a conference, a coach, a mastermind and thought, gosh, it's just so expensive. And you know what? I get it because every time I write a check to invest in myself, I feel it too. But here's what I learned after more than 20 years in business. The entrepreneurs who build the biggest businesses aren't necessarily the smartest. They're the ones who never stop putting themselves in rooms that force them to Play Bigger.

And I was reminded of this again this week at the Forward Conference hosted by my friend Neil, and today I want to share why I believe investing in yourself is one of the highest return decisions you will ever make. Let's dive in. Welcome back to the Play Bigger podcast. I'm Raquel Quinet and if you're new here, this podcast is all about helping entrepreneurs build better systems, leverage AI, create more freedom so they ultimately can Play Bigger.

This isn't going to be a recap of everything that happened at Ford. There were incredible speakers, amazing content and so many, just so, many tactical takeaways, but that's not what stayed with me. Every year I leave this conference with one or two ideas that completely changed the way I think. And this year was no different. So I have attended Ford probably for the last three or four years. And honestly, every year I walk in thinking there's no way they can make this better than last year. And somehow Neil always does. 

Neil and his team have mastered something that very few people understand they just don't create an event, they create an experience. Every detail matters, the energy, the environment, the conversations, the people you're surrounded by, and then out walks the surprise guest.

Yes, if you follow me on social, you probably see it. Leila Hermosy was at Forward this year. And if you know me, you know I absolutely love Leila. Not because she's famous, not because she's built incredible businesses, but because she's so unapologetic and she isn't trying to impress anyone. She isn't trying to sound smarter than everyone. She's just super direct, no fluffed, honest, and she's super confident, authentic.

And what I love the most when I saw her in person is she will openly tell you she doesn't have it all figured out. And that hit me. I was like, wow, I always thought that very, very successful people have things figured out. And what I realized, especially in this conference is like she admittedly said, I don't even know where I'm going to be in five years. We are just figuring some things out. We're doing a TV series.

I don't know if it's going to pan out. I don't know if we wasted money yet. I don't know if it's going to be a hit because they haven't beta tested. They haven't looked at the data, but they were willing to take the action to test it all. And because so many entrepreneurs believe confidence comes from having all the answers and knowing all the right things. But watching her reminded me that isn't what confidence is all about. Confidence is about taking action confidence doesn't come before action. So I think one of the biggest lies entrepreneurs believe is once I know enough, then Raquel, I'll be confident.

Confidence doesn't come from certainty. Confidence comes from keeping promises to yourself, taking action, making decisions, learning, adjusting, then doing it again. The entrepreneurs we admire aren't fearless. They all have some type of fear. They just built enough evidence that they can figure things out. And that's a completely different mindset. The other lesson that I learned is that the room matters more than the content.

Here's something I don't think enough people talk about. People ask me all the time, Raquel, was the conference worth it?

Honestly, the content is just a little part of the value. some of the biggest breakthroughs I have ever had happened during conversations between sessions at dinner in the hallway, meeting someone I had never met otherwise, watching how successful people think, watching how they solve problems, watching what's possible. And sometimes one conversation changes your trajectory more than an entire keynote. And that's why I continue to invest. Not because I need another notebook full of ideas, but because every time I put myself in a bigger room, I leave as a bigger leader. And believe it or not, as I looked at the lineup, Sharon, he was a person that I hired and coached me and mentored me. Kent, he was a person I had worked for, mentored me, coached me. And

I got to meet Ed Milet when I was working for Kent. So I had heard some of his stories already, but it always hits me different. And lesson number three is investment changes identity. People think you're paying for information. Guess what? You're not. You're paying for some kind of person who invests in growth. Every time you bet on yourself, you send yourself a message. I'm worth investing in that changes how you show up, how you make decisions, how you lead, how you charge, how you hire and how you think the investment isn't what changes you. The decision does when you decide to invest and it scares you a little bit, guess what? You start acting a little different.

And here's this week's like Play Bigger principle cause you know, I love to give you some kind of like thought behind all of this is the entrepreneurs who grow the fastest, guess what? Are not collecting more information. They are collecting, especially right now, better environments. Information is everywhere. Transformation actually happens in proximity. The right room compresses years of learning in just one conversation and the right coach helps you avoid mistakes you didn't even know you were about to make.

The right community raises your standards simply by being just around it. And that's why I continue investing in myself year after year, not because I've arrived, but because I never want to stop growing.

So here's my Play Bigger challenge for you: Ask yourself, what room have I been talking myself out of joining? Maybe it's because it's price too high. It's the investment. Maybe it's you just don't feel ready or maybe your business is not in a safe quote unquote safe place or maybe you're afraid you won't fit in, but that's exactly the room you actually need to be in. The best opportunities in my journey didn't come from staying comfortable.

They happened because I walked in rooms that absolutely stretch me. So one of the things I admire the most about entrepreneurs I respect isn't how much money they made. It's how they never stop being students. They never think they have it all figured out. They keep reading, they keep learning, they keep investing, they keep listening to podcasts, they keep evolving and every single time they do, they come back so much better.

And that's what I want for you, not just a bigger business, but a bigger life. One that you're constantly growing into the person your future requires. Because when you build better, you don't just build better businesses, you build the freedom to truly Play bigger.

And if this episode resonated with you, I want you to share it with another entrepreneur who needs to hear it. And if you're looking for a room filled with entrepreneurs who are committed to growing, implementing and building better businesses together, I invite you to go to letsplaybigger.com or send me a DM because we always have different things going on in our community. And until next time, I want you to keep building better, keep betting on yourself and truly keep Playing Bigger, my friend.