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Published on:

22nd Nov 2025

The $200M Lesson: Are You Paddling... or Riding the Wave?

After a conversation with a friend who built a $200 million gym franchise empire, this episode explores the age-old debate about hard work in entrepreneurship. Is it all about grinding 80 hours a week, or can you meditate your way to success with just a few hours of deep work? The answer lies in a powerful surfing metaphor: business success isn't about choosing one approach—it's about recognizing which season you're in. Learn how to identify whether you're in a paddling phase or a wave-riding phase, and why trying to do both at the wrong time can actually sabotage your results.

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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Transcript
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Speaker 1

I just finished a walk with a good friend of mine and who's built a $200 million gym empire, you know, around the States. As a as a franchise owner. And we were talking about hard work and, like,

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Speaker 1

what hard work is when it comes to entrepreneurship, when it comes to business. And you've got two really loud voices right on opposite ends of the the continuum.

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Speaker 1

And, you know, on the one hand, you've got hustle culture that says you've got to grind 80 hours a week, seven days a week,

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Speaker 1

no friends. All sacrifice. Like just just keep going. It's, it's an effort based argument. And on the other end of the continuum, we've got, you know, Zen hippies that that tell you it's okay.

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Speaker 1

You just got to work, you know, couple hours of deep work in the morning, and then, you know, you're set. You can you can meditate and drink margaritas all day. And, you know, it's it's easy and it's simple and it's not about effort. And, you know, as we were talking about it,

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Speaker 1

he dropped a metaphor that I thought was really powerful.

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Speaker 1

And it was, he said, you know, I, I look at it like surfing, right? Like you, you got a, you got to paddle like hell, like to, to get out there. And if you've been surfing and, and, you know, like you get out there like you're, you're going to, you're going to work like there's a reason surfers are, are fit for it typically.

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Speaker 1

Right. Like it's it's a lot of energy. It's a lot of effort to get out there. And you put in all that effort. And then sometimes you wait. Sometimes you're there. You you catch the the right wave right away. You set up, you ride that wave and you know you're going to hit some really big waves, you're going to hit some smaller waves.

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Speaker 1

But either way, chances are that that wave, for the most part, is like comes to an end to to some degree. And, you know, you, you, you basically get out, you you paddle again, you get back up and you do it again. And it's just part of the process. And it's not really a, hey, it's, it's a it's all about paddling or not.

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Speaker 1

It's all about riding the wave like it's about both. Because, you know, when you talk about a lot of these, these things that you see online about hard work and you know what it is that actually works like that, it's more nuanced than what you're what you see, obviously. But what this what this kind of highlighted for me is the different seasons that you go through as an entrepreneur, as a business owner, you know, you you go through these seasons where you feel like

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Speaker 1

paddling your ass off and you're

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Speaker 1

all the effort is going in.

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You're not catching many waves. It doesn't feel like it's worth it until it does. Right. And then you've got seasons where you catch the wave and it's it's next level and you're, you know, you're riding it and you're,

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Speaker 1

appreciate it on like you're, you're enjoying it. And it also like to me it's like this metaphor kind of captures the input in the output.

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Speaker 1

Like the input is all the effort, the output is the wave. And the reality is it's a cycle and it's just different seasons. And so the question really becomes like, which season are you in? Not which argument is right? Or you know, what is hard work or what's the right way. It's what season are you in? And if you have a wave right now, write it like lean into it, have fun, enjoy it.

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Speaker 1

Like don't feel like you've got to to paddle just for the sake of paddle. Like you're going to fuck up the wave, right? If you don't have a wave,

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Speaker 1

maybe it's time to to start paddling.

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Speaker 1

Get to it. It'll be worth it. You get your wave eventually and, hope it helps. Audios.

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About the Podcast

Repeatable Revenue
A podcast for MSPs and B2B business owners who want to scale sales.

Repeatable Revenue is hosted by Ray J. Green, an investor, entrepreneur, and strategic growth advisor to MSPs and B2B businesses. He's led national small business for the U.S. Chamber of Commerce, run turnarounds as a CEO for private equity groups, and advised 100s of MSPs and B2B businesses on how to build sales teams and scale sales from Cabo, where he now lives with his family.

This podcast is a collection of interviews, lessons learned, and other infotainment to help you build your business... and the best version of yourself.