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Published on:

5th Sep 2025

The MSP Growth Strategy No One Talks About (Compounding Wins)

I share how downloading a "Couch to 5K" app - despite being able to run half marathons - taught me a powerful lesson about achieving big goals in business.

After hitting a mental block that kept sabotaging my runs, I discovered that starting embarrassingly easy and building small, consistent wins creates unstoppable momentum. This same principle of breaking down massive business goals into bite-sized, achievable steps helps you develop a winning habit that compounds over time, whether you're trying to scale from $1M to $10M or launch that outbound sales operation you've been putting off.

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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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Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

Transcript

00;00;00;01 - 00;00;27;36

Unknown

So there was a guy who's raced in a dozen half marathons. Some of them hung over, frankly. And I've I've raced in triathlons and I'm downloading an app that is actually designed to train people who can't run around the block. I'm going to share why doing something like embarrassingly easy was exactly what I needed to do. And how the same principle can help you unlock those huge, hairy, audacious goals that you have in your business.

00;00;27;37 - 00;00;48;32

Unknown

Hey what's up? I'm Ray green, founder of MSP Sales Partners and for as long as I can remember, I've had this rule of thumb. Like I need to maintain half marathon conditioning. Like that's just my my basic rule. Like, as long as I can run half marathon on command, I feel pretty good about myself now. Sometimes I've been significantly better than that.

00;00;48;33 - 00;01;07;38

Unknown

Sometimes I've had to struggle to get there. But generally speaking, from a physical standpoint, I've always been able to run a half marathon, or at least in my in my recent history, I recently ran into this blocker with running just in general. I would start running and I would get, you know, two minutes in, three minutes in, and all of a sudden I'd start like, oh, you know what?

00;01;07;38 - 00;01;21;15

Unknown

I forgot to do whatever the hell I was, right? And I feel like, let me, let me stop for just a second. I'd and grab my phone and let me just hammer this out real quick. And I never really get back to running. And then, you know, the next day I'd say, you know. Oh, yeah, like this time, this time I'm for real.

00;01;21;20 - 00;01;36;28

Unknown

So I'd go out and I would, you know, I'd start my I'd start running and I'd get 4 or 5 minutes in and the same thing would happen, right? Like it's like this. There's like, the secret to do list somewhere in the back of my head that I can call upon. Tell me, avoid doing whatever it is that I'm doing today.

00;01;36;43 - 00;01;48;47

Unknown

Right? Like if I'm doing something today and I just want to procrastinate or I want to avoid it, there's like this secret list somewhere in the back of my head that says, oh, hey, remember all of this shit that you were supposed to be doing before you hit? Let's do that now. Let's do that now. Let's do that now.

00;01;48;47 - 00;02;11;57

Unknown

I started to, like, realize this. And I said, you know what? Like, I've I've got to change this. I don't like where this is going. And it had nothing to do with physical conditioning. Right. It wasn't like I would start running and be like, oh my God, I can't, I can't breathe. It was it was like I'd just get going and I was either bored, I didn't want to do it, and it wasn't even incredibly hard.

00;02;12;01 - 00;02;34;16

Unknown

It was I wanted to have achieved the goal, but there was some mental blocker that was that I was plateauing at right and I kept butting up against. I've never been one to to be a huge excuse maker. In fact, like most of the time, like when it's one of my pet peeves when I hear people making excuses, you know, like I'm on the outside looking in, I could be like, if I'm coaching myself, I'd be like, hey, don't you see the pattern?

00;02;34;19 - 00;02;52;02

Unknown

Don't you see what's happening here? Whatever the hell that blocker is, it's it is keeping you from achieving the thing that you want, right? So I you I go out and I download this, this app coach to five K right. And I get the app and I tell my wife, I said hey I'm going to, I'm going to start running the couch to five K app.

00;02;52;13 - 00;03;23;56

Unknown

And she looks at me and she's like, okay. And because the couch to five K if you're not familiar with it, it's a program where they can't. They help you condition and train from not being able to run at all to being able to run A5K. Right. And they do that by like interval training. So they they'll they'll have you run, you know, for one minute, you know, and then they'll have you walk for five minutes and have you run for one hour, you know, and like and so you do that and then the next time you do that they'll have you run for, you know, 90s and then it'll just kind of inch up

00;03;23;56 - 00;03;38;21

Unknown

an inch, up an inch up. And when my, when I told my wife about it, she said, well, babe, like you, you know, this has nothing to do with your ability to run, like, just go do it. I said, I get it, I get it. I'm like, I'm hitting this blocker. And I said, you know what I'm going to do?

00;03;38;21 - 00;03;52;56

Unknown

I'm going to I'm going to find a way through it. Like, I'm not going to accept this. I'm not going to accept, like the little mental tricks that are that are happening in my head. Whatever the reason is, right? You just got to find a way through it. So this was my this was my solution. So I go out and I start running.

00;03;53;09 - 00;04;10;32

Unknown

Right? And I would get out there and I would run for a minute and it would say do. And it would tell me, all right, it's time to walk for four minutes. No bullshit. Like I felt like I feel like I'm cheating right now. And in the back of my mind, I'm thinking, this is too easy. Like I'm supposed to be pushing myself.

00;04;10;32 - 00;04;30;51

Unknown

I'm supposed to be, like, pushing the limits. I'm supposed to be like finding what my limitations are and then, like, entering those. And I'm not supposed to be going backwards like me, you know? I'm just going to I'm going to trust the system. Like I'm I'm going to test this theory. I'm going to start with something easy, and I'm going to end up and I'm going to work my way through this app, and I'm going to work my way through the next version of the app and the next version of the app.

00;04;30;51 - 00;04;46;09

Unknown

Back to where I know I am physically and mentally. I just need to to kind of catch up and like, blast through these walls, right? So like occasionally I would, I would skip one, right? I'd get to a point of like, okay, like I did one and two and I'm like, all right, I know I can do the fourth one.

00;04;46;19 - 00;05;21;33

Unknown

Like I don't need to do the third. And so I kind of went through the five K version pretty quickly. As I was doing that, I was compounding wins, right? So instead of every time going out to run and hitting that three minute wall, that five minute wall is as dumb as it sounds like. It wasn't physical, but I was just like, kept hitting this thing instead of hitting that and quitting and then leaving with that being the record, what I did was I went easy and decided to build up, and what I was doing was building the wins.

00;05;21;33 - 00;05;39;32

Unknown

I was building the habit of winning. I was building the habit of succeeding. Right. Because it was easy. So instead of going out and saying, I'm going to run for two hours today and not being able to do that right and getting a few minutes in and going, shit, there's like an hour and 57 minutes ahead of me.

00;05;39;32 - 00;06;05;33

Unknown

I just don't want to do it. What I would do is go out and say, I'm going to go out for a minute. How do you not do that? This is how winning works. Winning is a habit. Winning is something that compounds on on each other, like your wins, your small wins compounds and they start to become exponential and when you start to train yourself to when I do x, I'm going to achieve the thing, right?

00;06;05;33 - 00;06;20;41

Unknown

Like I'm going to actually I'm going to win versus, hey, I'm going to keep trying new ideas and and they're not going to work. I'm going to keep trying this and it's not going to work, and I'm going to keep trying this and it's not going to work. You actually like subconsciously you start to doubt yourself because you're like, well, you know what?

00;06;20;53 - 00;06;42;01

Unknown

Yeah. The last four times that you said that that you're going to try that new idea, you're going to try that new initiative, you're going to hire that new role, you're going to implement that new system, you're going to adopt that new platform. You're going to whatever it is you you start to doubt yourself. And when you start to doubt yourself, it creates this vicious cycle.

00;06;42;01 - 00;07;11;24

Unknown

Self-doubt and self-confidence are the things that are, like, constantly moving, right? Like there's always like an ebb and flow. You're either constantly increasing it or constantly decrease again. And it's not a perfect line, but generally speaking, you're moving one direction or you're moving another direction. And if you consist urgently set goals that you don't achieve and you accept the fact that you don't achieve them, it makes the next time that you set a goal less likely to achieve it.

00;07;11;24 - 00;07;26;46

Unknown

And then if you do that three times in a row, four times in a row, five times in a row, this is how people end up personal or business, where they end up in spaces where they're like, I'm just going to like blank promises. I'm just, I'm going to I'm going to lose 50 pounds. Like, we're going to hit a million this year.

00;07;26;48 - 00;07;46;26

Unknown

This is our sales goal. We're going to hire a rock star. We're going to have yeah, we're going to run our ops like, you know, a Swiss watch, like we're going to like, and you say these things that are empty promises and deep down you know it because the track record that you have with yourself or with your business has been one where you accept those losses.

00;07;46;35 - 00;08;01;20

Unknown

You know, there's a really cool video that I love with, with Jesse Gensler and, and Chad Wright, and they talk about, you know, I will not quit. I will not quit. I wanted so maybe there's a way that I could have just forced it. Right? If I just, like, push through that barrier. And that's that's definitely one way to do this.

00;08;01;20 - 00;08;20;57

Unknown

But in my case, I don't have Chad. Right? I don't have a Navy Seal by my side, like, cheer me on. And I said, you know what I need to do? I need to redevelop the habit of winning. I need to redevelop the the compounding wins and retrain my brain that when I go out to run today, I'm going to hit the fucking goal.

00;08;21;01 - 00;08;43;12

Unknown

Why? Because it's so easy that there's no reason that I wouldn't now here's how this relates to business. I've already hit on the fact that when you consistently set goals and you don't achieve them, you as a culture, as a team, as a leader, you start to accept the fact that you may not hit those goals, which I think is just like really toxic as a, as a, as a culture within a business.

00;08;43;27 - 00;09;13;02

Unknown

I think when you set goals, you and everyone else has to sit around and believe that you going to hit them. And this principle of small wins, compounding is something that you can implement in your business to start achieving mass of goals. And here's what I mean. If you have the goal of standing up an outbound operation, right, just for example, say, you know what, I want an outbound sales team and we want to we want to be generating, you know, 100 K MRA in 18 months.

00;09;13;02 - 00;09;33;05

Unknown

If you set out to do that and you start executing and you are going into that with a track record of not achieving those goals, you are going out with subconsciously willing to accept the fact that you may not hit them. That goal, that MRO goal feels like the half marathon. It feels like the two hour run that you have ahead of you.

00;09;33;05 - 00;09;50;15

Unknown

And so you get going really on you, and you hit those those initial obstacles. You hit that initial friction and a couple of things happen. One is you're like, all right, maybe this isn't actually going to happen. I mean, this isn't realistic or you you do kind of the same thing that my brain does. It starts drawing on these other distractions.

00;09;50;15 - 00;10;09;39

Unknown

It starts drawing on these this to do list of sitting back there. And it's like, hey, this is conveniently sitting here to allow you to avoid achieving the thing that's in front of you, because the goal is so fucking big, it feels it feels not quite impossible, but it's like, oh man, I don't know how to get from here to here.

00;10;09;39 - 00;10;29;20

Unknown

Instead of taking it from here to here, we take it from here to here. I want to stand up and outbound operation. Okay. What are some baby steps that we can put in place? What are some small, embarrassingly easy, achievable goals that we can put in place that we can hit in the next 30 days and next 90 days?

00;10;29;20 - 00;10;46;16

Unknown

Can we say we're going to get out X number of emails and make X number of phone calls, not even worrying about results, right? Like we're just going to get the flywheel in motion. We're going to get the script written. We're going to get the copy written. We're going to get the systems in place, and we're just going to start executing like we're going to get some activity going.

00;10;46;16 - 00;11;07;19

Unknown

We're not even going to worry about the leads just yet or the appointments or the sales. And you say, well, that'll be come on, Ray. Like clearly we can get some scripts written and some emails written in, make some calls the next night. Okay. Well then do it right. That's your equivalent of the one minute run. Now that we did that, what's the next easily achievable goal.

00;11;07;24 - 00;11;36;21

Unknown

And you end up and you would be surprised at how quickly that curve bends because there's something called gates law. And gates law basically says we overestimate what we can do in one year. And then we dramatically underestimate what we can do in ten years. Okay. And it's because most things in life are exponential, and we overestimate what we can do in this very short period of time.

00;11;36;21 - 00;11;52;42

Unknown

We underestimate what we can do in this extended period of time. And because we overestimate what we can do in the short period of time, we end up giving up. So we never actually experience the big results that happen on the other side of the curve. If you recognize with gates law, you say, hey, is actually over the long haul.

00;11;52;47 - 00;12;15;11

Unknown

Let's underestimate what we can do in the short run and overestimate what we can do in the long run. Let's reverse that, and let's say let's run for one minute. Let's run for 90s. Let's run for 100 and 80s. Let's run for ten minutes. And that is where you see the curve. Like that is where you see the real results, the exponential results that happen over time.

00;12;15;16 - 00;12;37;21

Unknown

And my lesson with the couch to five k, I think, validates that it's the exact same psychology. You go back and you say, let me underestimate what I can do in the short run instead of overestimate. Let me underestimate that. Let me overestimate what I can do in the long run, because it's over the long run after things have really compounded that give you the results that you're actually looking for.

00;12;37;21 - 00;13;10;53

Unknown

So I tell you all this to say, like, you don't have to go run. You don't have to to go get the couch to five K app. You don't like that. That's not the point. The point is, if you want to hit a really big goal, it is oftentimes better to break that down into bite sized pieces. And I mean embarrassingly easy bite sized pieces so that you create the habit of winning, you create the habit of achieving, and that every time that you set the new mark, you now believe in your brain and your team believes in their brains.

00;13;10;59 - 00;13;41;15

Unknown

We're going to hit it. Why? Because we hit the last one. As that happens, the team has momentum, the team has traction. And you something like something kicks in and it becomes just a hell of a lot easier to hit those elusive goals. But it may mean an embarrassingly small, bite sized portion of it to get going. So if you are a smaller MSP and you're gunning for 10 million, or you're a 10 million MSP and you're gunning for 100 million, don't go into that marathon.

00;13;41;15 - 00;14;06;48

Unknown

Don't go into that half marathon and think, Holy shit. Like, I've got to get all of this done. In the short period of time, the road from 1 to 10 and the road from 10 to 100 is a curve that looks like that, right? It is a it is an exponential curve that requires smaller wins on the front end, compounding, gaining traction and giving you the results that you want over time, you'll be glad to know I've knocked out the five cap.

00;14;06;48 - 00;14;27;32

Unknown

I've knocked out the ten cap. I'm now at a point where mentally and physically I'm reaching the limitations, but I'm now going into that with more confidence because I just have a long track record of the winds up to that point. So I hope this has been helpful. If not from a business standpoint, at least from a personal standpoint.

00;14;27;32 - 00;14;50;54

Unknown

And I just personally find this this principle has worked for me many times. And I, you know, taking one step backwards and and doing something embarrassingly easy just accelerates the curve to actually get where I want to go. And, if it has been helpful for you, go ahead and subscribe to the channel. Or if you are an MSP and looking to to grow, feel free to check out MSP Sales Toolbox.

00;14;50;54 - 00;15;08;48

Unknown

That link is below as well. In that toolbox, we've got, you know, sales templates and forecasting models and playbooks and things that we put in there basically every month. And you have access to that for, for life for free. Or my email newsletter link is below to where we drop, you know, sales tips and business tips every single week.

00;15;08;48 - 00;15;11;50

Unknown

So, I'll see you in the next video. Thanks for watching. Audios.

Show artwork for Repeatable Revenue

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.