The English Teacher Who Became a Top 50 Sales Trainer in the World - The Ray J. Green Show

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The English Teacher Who Became a Top 50 Sales Trainer in the World

The first year of owning a business doesn’t look like growth—it looks like uncertainty, pressure, and constant second-guessing. This episode examines what really happens after the deal closes, and why most expectations about ownership don’t survive contact with reality.

What You’ll Learn in This Episode:

  • What the first year of ownership actually demands from you—mentally and operationally
  • Why the transition from operator to owner exposes gaps you didn’t know you had
  • The question that matters more than deal terms before you buy a business

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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.

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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YouTube | LinkedIn | Facebook | Twitter | Instagram

Transcript

You know, we got married in October and found out we were pregnant in January. I mean, it was not part of the plan. Something flipped, like a switch flipped. I'm standing there in this cubicle, and this guy, he'd been referred to me by someone we both know and trusted. And he says, I lost 70% of my business.

And I said, do you want to see if we can help? He said, I don't think so. And I looked at that sonogram and I thought, okay, I know what this guy said is dumb, but I have to push through this because there's somebody who is going to depend on me. And it was sort of this watershed moment of for me. You just have to fight through some things, and it's not even a fight.

It's just you don't pick the first thing they say at face value. That's Adam Boyden.

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Adam is a former high school English teacher, football coach for for kids, and he was going to go into law, bombed the Lsat and ended up kind of stumbling into the cold, calling some CEOs and very quickly became a top 50 performer globally in the Sandler Training Network. And he coauthored a bestselling book.

As a VP of sales. He led a company to get acquired and then a year ago actually bought his own training company. And he's hands down the best simple fire that I know. And don't I don't say that lightly. And that's very difficult to do, is simplifying very complex things. And he does it better than than anyone I know.

And that story that you just heard about the sonogram, you know, that's kind of like the whole episode. Um, you know how a guy who never plans to, to go into sales has built everything that he has by keeping things very simple, pushing through the really hard moments and fighting for the people that depend on.

So this is a really good one. Let's dive in. All right. What's going on, Adam? Welcome to the show, man.

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Hey, great to be with you, Ray. I wish I were in Mexico, but, you know, I'm not so. Well, just do it from this. I love, love, love.

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To have a margarita with you. We'll do it, and we'll do it in person next time. Man, I believe if my research is is correct here, I believe this is March is the year anniversary of acquiring Trinity Training and Development. Is that. Is that right? Is that a year?

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Yeah. It was it was a lot. But yeah, we got it done. I appreciate it man. Thanks for remember that.

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So one year ago the day that it closed. How did you feel.

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You know you have those experiences in life and you're like this is going to be the pinnacle. And you think that's everything. And everyone says it's not, other than maybe winning the Super Bowl. It was one of these things. It was like, okay, great. And now I have all this work to do. But I will tell you, one of the biggest things it did for me, it settled this thing where I was always looking for what's next.

And when I was, when I got into like the training and consulting space, I never thought, this will be what I do. I'll go find the next thing. Well, I got the next thing. It happens to be in this space. And so it's sort of quieted that where it told me, these are not the things to worry. I, I don't even need to consider these opportunities.

I don't need to think about that. I don't need to worry about that, because I'm so busy working on the thing right in front of me. Does that make sense?

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Yeah. It does. How long? How long did you shop for? You were. I mean, you were looking for a company to buy for a while. Right.

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I started meeting with a good friend of mine from business school, probably in 2011, to fix it. We started talking about it, and what happened was we were on these different life tracks where he had kids, and then I was I was ready because I didn't have kids yet. He he had kids. And so that and then it switched and I was ready and he wasn't.

le conversation in itself. So:

en I started looking again in:

It's so easy. Here's how you do it. I'm like, took a long time and I may not be the smartest guy, but it took us a while. We looked a lot of things.

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In what's the last what's the last year been like? So when you when you bought it because you had a company, I mean, you were you you had your own business. Have you, are you merging them. What's the last year been like operationally?

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The last year was I get into things probably like you and I see all this opportunity and I think Corey let's go do it. But then I'm, I have to think through, oh who's actually going to do all that work. So we have the um, we have the training business like the, our what's historically the Northwood. And we're going to merge into Trinity.

That's our sales training business. So I'm always having to rethink how we delivered services to get me out of doing everything every day. Had a couple of failed attempts at figuring that out, and then had to start bringing some people on. On that side to do some delivery and rework it and then I. Inside of Trinity had to rework some things.

There wasn't a CRM, there wasn't some of the tracking we needed. We had to get our hands around what was happening on the digital side. I needed to bring somebody on to offload work. I hired a young guy who's really got a huge upside, and I said, hey, I'm going to hire you for three jobs. You're probably going to suck it one, be okay at another, and we're going to find the thing you're good at.

But we need help in all three areas. Get him on board, putting in financial controls. It's been nonstop, and you've probably been there where your days start at 7 a.m., in the end at 7 p.m., and it's calls and meetings all day. A lot of that nights where I'm laying in bed at 2 a.m. thinking, is this a bad idea?

Should I have done this other days where you're thinking, this is the greatest thing ever, and I'm so glad I did this. Absolutely. Roller coaster. Operationally, we're trying to do 20 things at once and people will say, you got to prioritize it. It's like, well, it feels like these are all really, really important and we really need to do these.

And I'm not a great prioritize. So we just we attack it.

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When you look back at either the transaction or the years since then, if you could do one thing over, you know, magic wand question is, is there anything that you would you would do differently? I.

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Oh, it's a great question. And often I'm going so fast that I don't find that 30 minutes to think about that I probably would have found some way in diligence. It wouldn't have changed the deal. I would have found some way to get under the hood a little bit more on a certain set of items that would enable me to plan the first 3 to 6 months better.

That way it would have said, all right, we're going to work on this and this and this, and we're not going to touch anything else. And you could have told me, do those things and I wouldn't have really paid attention or thought about it on this end. Having gone through it, it would cause me to say, I should do that again.

And if you think about acquisitions, it's probably why you keep doing them, because you get better at doing them.

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That's a good point. That's a good point. Are you still looking to buy or is that the thing right now? Would you? Would you buy another company right now?

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Uh, no, not right now. When we get to a place where I feel like we've got the controls, I think I was telling you, we've got to get a very operational EA in here to kind of free me up. And there are a few things we could do on the sales training side. T so I can step out of that. And I don't know people who've really done that very well.

I'm kind of figuring that out. If you know somebody and you go talk to who's been good at selling the thing, but not being the delivery model in a world or a skill set like sales, I'd love to meet them once we get there and this thing's a little more steady state. I would like to go buy a complementary product that we could build in with the goal that, hey, we're going to cross-sell into their customer base.

You probably see this, you start getting complementary companies and you're like, oh, you start seeing all these ways to cross-sell into them. And if you've got the ability to sell and market becomes thing. I've had probably five conversations with companies from various sizes, anywhere from 30 million to 500 million in the last two weeks.

And everybody's big issue is cross-selling. How do we do that?

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Yeah, you have good insight into that because of the nature of what you're doing and who your customers are, then you're going to see what their challenges are. So if you got to do due diligence and you could go in and find the pieces of information that you know now that would have helped you in the first 3 to 6 months, what would that have been?

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We were really dependent on Google ads, and we've been working away from that to develop other channels so that we're not single threaded. And we've been thinking through that. We were trying to increase similar communication via email. Not crazy. And I'm not talking thousands a week. I'm talking 20 to 50 a week.

And it turns out. Way back in:

Now think about that. If you've got an inbound model and half of them are landing in spam and you know how to write an email, you got a problem? I would have probably dug into that. I would have dug even more into the digital funnel to understand it, to work through. How do we optimize that? And what are some of the things we need to do in the short term?

And that I'm not I'm never really worried about delivery. That's my problem. You're probably great at it, but I'm always thinking, just go sell more. I think I would have thought through what can we do from a capacity standpoint so that we know how? All right. At this point, we need to reinvest in delivery.

Um, you learn that now because you went through and yes, I know and no one knew to say, hey, go look and see if you're on a any of your domains are on a blacklist.

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After this deal is done, there's probably all these lessons that you learn and you go, all right, let me make sure to correct next time I'm going to I'm going to make some other mistakes. I'm gonna screw the next one up, too. But I won't make these mistakes. Have you gone back and, like, created that list for yourself?

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No, I'm going to do it after this call is over. I'll probably say I need to do these three things.

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Well, good then. All right. Podcast over.

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We're done. No, I need a partner who is so great at that stuff. Uh, because my belief is just go sell more. But the problem is she needs somebody to help you learn a little more intentionally as you go through it. So, uh, but yeah, there, there a handful that I would do and, uh, you know, and part of it is, would I, I think the big question is how do I get enough?

I had a really good relationship with the seller, and we still do. I think the other thing I would look at is, how do I get enough trust where they could show me more once more verbally agreed. And I just say, hey, here's the price we're going to pay you. It's not going to change. I need this access to this information.

And sometimes the sellers don't even know. There are certain things you could ask me for in my business. And I'd be like, I gotta go ask somebody. I don't know where that is. I think the big key is, can you get the relationship with the seller to get that kind of information?

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Yeah, I bet a lot of that's built on on the trust. But then there's the the acquisition part of it. But then there's the operator part of you that says, I'm good with the deal. Now I'm thinking about details, not not to try to screw with the valuation, but I'm now thinking about how am I going to integrate this thing?

How am I going to run it? What am I to do? And making that flip, I imagine, is hard for the seller too.

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Well, and I think it is because the seller starts thinking really differently. Like you've signed an Loi. There's psychology fundamentally changes and they're great people. They're now thinking they're starting to think about getting out of it. But it's these transition retirement or whatever they're doing next.

And that becomes a real challenge to manage through it.

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We were talking before this and I said, you know, it's it's a it's a fun timing of a conversation because I've now we've got repeatable revenue ventures and I'm about to actively public. This will be the first time I say like looking for a company to buy. Having just done this a year ago, what would what would be your best piece of advice in terms of finding finding the right business and making the right deal?

Going through what you did and all the due diligence, all the searching, everything else. What would be your best advice to somebody? Me going out to buy a company to find the right one.

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Well, you already know the space you're looking at, and you know a ton about the business because you've been even you're working in these. But the space, you know, I have a ton of respect for you. So anybody listening to this like this is I am a big, big fan of Ray. I think the question you've got to get somebody to ask you is, what do you take for granted?

That's true in these businesses. What do you assume to be true because of how you think that

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potential is not true at all. So for me, for example, I would never have thought to think about the health of an email domain. That seems really simple, but that's the kind of thing. And sometimes somebody is is organized and is disciplined as structured as you. My guess is the blind spot is not realizing other people aren't as organized in a structured and as disciplined as yea, things aren't as tied up as neatly and you have to start asking, you know, what am I taking for granted because of how I am.

That's one thing. And then I would, I would be there was a guy I heard, his name is Mark Ali. I can see his face. He's really smart. And he had this framework for a business to buy. One of the things he said was he had this criteria and it had nothing to do with industry. It had nothing to do with price point. It had to do with a series of things like, can I add a new channel of revenue?

It wasn't just, can I optimize it or make it a little better? But he had these series of things. He said, if I can find some a business with some of these things to be true, where I understand this, this and this, but I can add a new channel or I could make it what's called a star business, he said. Those are the one I want to buy.

And when you think about a star business, you probably know this. This is for the listener. But in Boston, Consulting Group in the 60s came up with their Boston box, and the Boston Box said businesses are one of four things. It's a cow, meaning it throws off cash, but its growth is really limited. It's a star, meaning it's the number one business in a market growing more than 10 to 50% a year.

Uh, it could be a dog, which means you need to sell it off or shoot it because it's not a cash cow and it's not a star. It's a question mark. But, you know. No, but Ark's thought was, I want it. I'm looking for a star business. Now, the problem with star business is they cash, they eat a lot of cash, they grow a lot, and they can be really big.

And they can make you fabulously wealthy. Uh, but how do you find it? And so, as you go to look for it, I think it's being really, really clear on your criteria and

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how you leverage your superpowers to do it and not take things for granted in the process. I don't know if that was specific enough, but that's where I would go.

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Question some of your beliefs. Like there's there's things that we take for granted that we assume to be true based on how we operate or how we do things. And if we assume that that's true somewhere else, and then you find out afterwards not the case, I think that's really good advice. Kudos to you, man. Like you, you put in a lot of work on that.

I mean, I know I knew throughout the stage like we were friends and I was like, all right, yeah, I knew you were going to land one, but that's, uh, that's awesome. Um, it's been.

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Well, I gotta tell you, it was it was it was a walk of faith because you're sitting here going, is this ever going to happen? And I'd actually given up probably at September of 24. I'm just going to make peace that this isn't going to happen. And I'm going to focus on this other business. And a month later, the door opens for this and I'm like, I'm just really blessed.

But one of the things that I think was the key success factor is I felt like I could trust the seller. We might do things differently, but that made it easier, cleaner and faster. And

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the more you can find a seller you want to do the deal with, the better.

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Did you know them before?

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No, but I met in and after the first two conversations I said, this guy's legit because everybody's worried. Why are they selling? There's got to be something they're hiding. And he's like, look, we're getting older. We want to spend time not working. I just could trust this guy and he'd be honest, like, I don't know, or I've never done that or I haven't bothered with that.

And he would tell me what he did know and he just made the deal so much easier. In fact, at one point, you know, the attorneys are working on things, and he and I just kind of pulled off to the side and said, hey, let's work this out, you and me. And that was a massive win that got through an impasse. Here's one thing that helps help me.

I had a guy help me on my deal. Name's Patrick and we still do a lot of work with Patrick, so I really trust him. He for me was a really calm presence that could help step in when I would get emotionally involved in the deal. Because I'm sitting here thinking about making the biggest risk of my life the biggest bet, and you get attorneys in there and accountants and everything starts happening.

And basically you and the seller are writing checks to everybody else, right? And for you guys, everything to align. There's not as much on the line for all these other people. And I had somebody who could kind of step in at times and when I got emotionally involved or frustrated and possibly could have blown the deal up, he was able to kind of navigate us through that.

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So a good advisor, like somebody to to help temper some of the the emotions that you're going through.

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He was part of some of the negotiations just because he could kind of step in with attorneys or CPAs, and he could just very calmly handle something where I'm just getting worked up.

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I was reading your background and like when, when I'm doing this right now and we're like I said, we've already known each other. So this is this is cool. And I'm reading about a friend that I already know and I'm like, hey, this is this is kind of cool. And I forgot that you were you were an English teacher. And you, you've you made the transition from, from from teaching straight into sales.

And if I, if, if I, if I'm correct, you went like straight from high school English teacher to cold calling CEOs. Right.

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There was a little gap and I and I can fill that in. But the gap was not big. I mean, I went from English teacher to doing nonprofit work, which wasn't a lot different in some ways. And then I waited. I bartend it and was a writer. And then I went to business school and then got into cold calling. But the funny thing was, you know, you come out, you were you went to business school at SMU, right?

And you come out and you're like, I got ABA. I've learned a lot. I busted my ass. I sat in a windowless room in cold, cold for $15 an hour. Right. I've got this fancy degree. That's what I did. And I'm thinking, oh my gosh, English teaching was so much more intellectually stimulating. The math.

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Do you remember your first week? So you go from English teacher to MBA and your first week of cold calling. What's that like?

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And this would be fun to compare notes because I know you built a sales word, um, for the chamber, but I remember he kind of spent 30 minutes with me, an hour kind of saying, hey, here's how we do things. This is the call. I remember he had a he had a book. It was a book of lists. And it was like this big. And he kind of threw it down.

And he's like, all right, just only call on presidents and CEOs. I don't want to talk to anybody else. And he said, here's what you need to do. And I literally just stared at that phone, and I looked at that list and I just started calling. I hated it, and so anytime I had anything good happen, I wanted to run down the hall and talk to somebody about it.

Not so much to get him. Attaboy. But just to kind of. Can you correct me? Can you steer me? But I thought, what the hell am I doing? I was too dumb to quit, though, so I just kept doing it. I'm curious. Like you led the team at the chamber. So did you start making calls there, or how did that work for you?

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I started in cold calling, and I got. I got the job I because I moved to Dallas and my goal was to get into politics. So I'm, I can't remember how I was 20, 20, 20, 22, something like that.

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By the way, the photos of you, the photos, the photos of you from back then Completely different.

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Oh, it's funny. And there's like different versions. There's like, there's like fat Ray and then there's skinny Ray and there's like, I went through some phases at the chamber and I started at the chamber. I saw their ad and it was like something like free enterprise, defend American business. This, that.

I'm like, this is my crew, because I've got a political blog at the time. I'm trying to like, make a name for myself. And I said, I'm gonna get into politics, but I don't have a law degree. In fact, I don't even have a real degree. And I don't have, you know, family in politics. So I'll go in through sales. And so I said, I'll plug my nose and do this stupid sales thing.

But my goal was to be a lobbyist, like from day one. I said, I'm just going to do this. I started volunteering, I'm like, by day I'll do the cold calling and by night I'll start volunteering for the lobbyists and stuffing envelopes and doing all this other shit. I was not good at cold calling, but I had some kind of.

I had somebody come to me and say, hey, this is what I do. And and Charles was his name, and he just stayed there my whole career. And I don't know what made this guy so generous, but he came over and said, basically, I'm going to save you and said, this is how we do it. This is my script. You can sit with me. And he and he and I just started copying all the shit that he did, and I, I managed to get by because I didn't have a lot of real sales experience, and and I didn't like it.

The thing that saved me, looking back was I was at least calling on something that I loved, at least at the time, like, I've, I've since lost some of the, the, the passion for politics. But when I got Ahold of somebody, then we were talking about something that I was fired up about, which meant I went off script, but it didn't matter because I was so fired up and pastured about the thing that that's how I sold was, was through that.

And eventually I managed to to work my way into to management and that eventually, like executive management there. Dude, I was I was so shy and introverted. I picked the cubicle furthest in the corner so nobody could hear me. And I would like, lean down and like, talk really low, you know, like, so people like it was.

Yeah. I didn't I didn't want a.

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Late night DJ.

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Yeah yeah yeah. Everybody but I, I made good money doing it. Um, and eventually, like, I figured it out and, you know, it was, it was something that I loved. And eventually, 15 years later, I really couldn't stand politics. And I loved sales. So I started for the politics, and I hated sales. And then I left.

Yeah, it's weird, it's wild. But sales is a life skill, man. Like, it's it's like you. It's it's it's a life skill everywhere, you know?

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So I'm leading. I'm reading the, uh, the Almanac of Naval Ravikant. Did I say his name right? Mhm. Do you know.

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Yeah. Um. Yeah.

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Yeah, yeah. Learn to build things and learn to sell. And, you know, I think about my own kids and I'm thinking just go like, if you can learn to sell and you can create something that you're good at, you're set right. Even in the age of AI. Now, I don't know how well this statement will age, but that's that would be my belief because you still have to be able to sell.

Uh, so I'm curious, how did you go from the chamber to SMU?

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I had been at the chamber for for 15 years. I'd worked my way up as managing director of every like basically all small, mid-sized business nationally. The conversation I had with the COO at the time, who was a mentor of mine, she said, hey, like, your next move is here. Like that's like, there's no there's no you can't go further up in the organization.

You're already in executive management. The next move is here, and here I am. I'm running I'm running the national sales from Dallas. But our office has ping pong tables and free Red bull, and we're in shorts and flip flops, and we're like, we're crushing the numbers. But it's this very informal startup environment.

And I wanted nothing to do with with ties. I wanted nothing to do at this point with real, real politics makes.

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So much sense while you're in Mexico now.

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Dress code man, I was like, fuck that, I don't want to do that. And so I talked to the COO and I said, I don't think I want to do that. And she said, well, we don't think we want you to leave, but why don't we do this like, you know, effectively get your MBA here. We'll help you out with some of this. You run the business, continue to run the business for a couple of years, and then we'll we'll play it by ear.

We'll see. We'll see what happens. So, you know, we it's almost like a mutual arrangement. And at the end of that. SMU has a lot of a good finance network. And I started networking with some private equity people and decided while I was getting my MBA, I wanted to do something in private equity, you know, and that's the that's the direction that I went to.

And somehow that landed me in Mexico.

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You asked about the English teacher thing, and this was really interesting. Somebody said, hey, what are you really good at? And I said, look, I've probably got two things I'm good at. One is in this guy's in private equity. He's he's responsible for sourcing deals for a pretty large fund. And he was talking to me about how they how they source deals.

And he had some questions because he it's ultimately it's a sales funnel. And he said what are you good at? I said, I'm really I think I'm good at simplifying things so that people can actually execute on them. And you probably have seen a lot of companies where they overengineered sales and thus nothing actually happens because it's too overengineered.

No one puts anything anywhere. No one documents because they're asking for too much information. I said, that's why I said number two. I think I'm better than average at trying to get a sense of the story that's in the customer's head or the buyer's head, and teaching you to talk in terms of that, rather than in terms of your your product or your offer.

He said, you got a humanities background. I said, yeah, I mean, I was an English teacher. And he said, a lot of times the people who are very engineering Stem are science process oriented. This is the thing they struggle with. You can kind of help navigate us through some of that. And I think that's where the English teacher piece, for some reason, it's kind of benefited me over here is, I think in terms of the story.

And I couldn't I honestly, I couldn't say, hey, here's the framework for the story, but it just sort of plays itself out. And there's a guy that a friend of mine I want you to meet. His business partner was homeschooled. He was the youngest of seven, and he just read like 3 million bucks. And he said, Adam, he's read so much that he just can see things because he's just read a lot.

He said. So he's real. Like in the world of business, he could help us tell stories better because he's just read everything. And so that's kind of the connection to sales, uh, at least in the the execution side of it.

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I'm a big fan of yours. In, in when I see you are hands down the best amplifier that I've ever met of of really anything but sales in particular. And because I've had you you've been you've been here in Cabo and, you know, you did a workshop, some of the objections that you were talking about, some of the processes you were talking about, it was all based on simplicity.

And to me, you have to you have to understand something more to make it simple than you do to make it complex. Like it's harder to make it simple than it, that it sounds. So you have these one liners and these ways of simplifying things that I was like, damn, that's good, that's good. I'm curious. Like, is that a is that a skill that you developed from teaching, or is that based on a different belief system that you have or something else?

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I probably have this really big fear that I'm not going to understand something, and I will work really hard to understand it. You know, when I

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when I work with a client and you probably have seen this because I was a client of yours and you've worked with a ton of companies. And one of the things that happens is if you listen long enough, you start to realize, oh, you got the same problem as somebody else. You dress it up differently, but at the heart, it's really the same problem.

It takes listening a really long time to go from what people say. The issue is to what the real core issue is, the root cause. And I'm always thinking, am I missing something? Maybe there's something else and there's probably something else I've missed somewhere. But we have to kind of keep drilling down and and there's just been for me.

There's a fear that I don't understand it. So I just keep trying to understand. I'm like, oh, it all kind of comes into these handful of issues. Um, the other thing that when I was in school, I kind of bagged liberal arts degrees sometimes because I felt like I got out and didn't know what to do with it. It kind of it bore for 20 years later, I would see these interconnections between like philosophy and research and sociology and literature and religion, but I didn't know what to do with it.

And now in business, I kind of there's just something you'll see kind of connect because of some of the stuff you and I read or talk about, and I feel like, okay, if I can't make this so simple, they get it, then I'm not doing my job. So I sort of feel compulsive. I've got this compulsive needing to like, help the person I'm working with get this idea so they can go and use it, and they can get to the next level and solve the next problem.

Or mosey talks about get to that level. Feet the boss. And I'm just trying to help people beat that boss. But it's got to be simple enough that they can do it. And it's like, ah, I get it.

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I think you say things like that, but it's like a it's a good distraction. Like because like because you're, you're very sharp and you can't, you can't simplify things unless you truly know your shit. And speaking of the chamber, I had a I was in a one of my first big executive meetings. The COO was like, you can see the white House because, you know, and the VP brings me in and this is like my guest appearance as a low level manager.

And I'm sitting in the room with people whose names are on the list of, like, the most 100 influential lobbyists in some state. And I'm like, you know, I'm young and I'm like, all right, this is exciting. And the environment lobbyist said something to the CEO and she said, do you think you're fucking smarter than me?

Do you think saying a whole bunch of shit that I don't understand makes you smarter than me? Try again. It is my first. And I'm like, wow, this is how we do things. But then I. But it was also a lesson that stuck with me for two reasons one. Like, okay. Like for obvious reasons. The second was it's hard to simplify things.

Like, it's actually easy to use a bunch of jargon. It's it's easy to, to repeat the shit you see in a book. It's hard to take what you see in the book and say, hey, let me break this down. And you used when you were here at Kiawah. I remember one of your one liners, uh, Jeff, you're doing the workshop with any. And he said, well, I always, I always get this thing.

Price pushback, price pushback, like other people are cheaper. And you said, well, why do you think that is? No, just ask that question when they say, hey, there's so much cheaper, you can just ask them, why do you think that is? And I was like, dude, the simplicity is beautiful, right? And do you think is that teachable?

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Yeah, I think that is. Um. So are you familiar? Shane parrish.

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Yeah.

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Yep. I was reading, um, his his point on first principles and questioning these things that we believe are true. And you think about it, it's like, okay, it's really important. Well, let's talk about salespeople. There's a young guy on our team really love this guy. Really excited about his future. Uh, I hope this age as well.

And, uh, we're talking about somebody called in and wanted some pricing so they could present it to their CEO. And I said, what? When? Because I think you've got to get people thinking so that they don't need you. Because if you can teach them to think, they won't need to come to you or me to get all their questions answered.

And so I asked him, I said, what this his first principle is thinking is best. I can do it. I said, what assumptions are you making? He struggled with that for a minute, and I said, all right, if she's going to present pricing to the CEO, what do you believe is true for that to be a legitimate comment? And we it took him a while to get to the point and was like, oh, I'm assuming she's seen this.

She wants this. We're the only one. And we're at that point, I said, okay, great. Now what question do you need to ask when you're on the phone with her. It's like building a muscle. So it took a little while for him to realize, oh, I need to ask. I need to ask, are you sure you're ready for that? Or

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do you really? You know, typically people only ask him for pricing when they've made a decision. Is that where we are? I think sometimes it's just simplifying it. Now, let me ask you this because I want to turn this back on you. What is the thing, the problem you can solve that when you're talking to it could have been me four years ago.

It could be clients that come to you now. What's the thing that seems like this big Gordian knot to other people, but you kind of just get and you just can like, you're like, oh, this is pretty simple. And I always have sometimes insecure about this. I'm like, this is I feel like you're going to get bad at me because I'm what I'm going to present you.

It's not rocket science. That's always my big insecurity.

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What is the belief that they have that's limiting them in particular from getting to a to a certain point?

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Yeah. Because you kind of look at it and I'm like, oh, here's what it is like. It's so clear to you. You just take it for granted because maybe it's a superpower. It's this knowledge you've acquired through 25 years of just grinding.

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It's applying what people already know to a space that they don't know, but it's the exact same underlying principle. So you take like a word with a lot of IT companies. Well, do they know process. They know systems they know like shit man. When I when I'm talking to IT companies, they have delivery dialed in in a way that I go, wow, I wish I could productize the service that well, you know, like it's packaged, it's clean, the text, it's clean, and I'm like, damn.

But then we come to talk about sales and it's just big clusterfuck. And I go, guys, it's the exact same principle. Like let me. Like a perfect example is you want to hire a level one tech. Would you go hire somebody that doesn't speak English? No. Would you hire the cheapest person that you could find? No. Would you hire somebody that's maybe instead coachable and kind of loves tech at least, and maybe has some baseline?

Yeah. Okay. So when you go to hire your SDR, why are you trying to hire a $2 an hour person overseas that has no experience and no this like, dude, just apply the same principles, process people, all the stuff that worked over here, we just apply it over here. And I think that's one of them. I imagine that's probably one of them.

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It's funny because I see people, they know how to have this conversation with this buyer or this customer, but if I make a slight change in the customer, they don't realize the same underlying framework or principle applies. You just have to change some of the inputs and helping them see that. It's kind of like I almost am like, I guess this is why I'm in business, because we just we see these things that we help you make that shift.

So that I think that's somewhat simplicity because like, you just see the simplicity. You're like, oh, the real thing is the process. Let's go apply the process.

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I read, I know this is we feel the same on this. And it's we have this like, you don't don't go hire salespeople to start. And I know you've worked with like a lot of law firms. You work like with technical people. I work with the IT companies and these folks a lot of times don't. Not only do they not feel like they can sell, they don't like sales, right?

Like they want to avoid it at all costs. But you say don't hire a salesperson. So you have to. For people that have a huge reluctance to sale to sales in general. Sell me on why that's true. Why do you why is that true for you?

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I will give you the reason that I think is probably I think I've got two. So the first one is in the early days of the business, when customers in cash are absolutely critical. You can't one. No one is going to care about it the way an owner or a founder cares about it, and even an owner or founder who says, I'm not good at sales.

You sit across the table from them and you see something in their eyes. You're like, I trust you with my money. Okay, so early on, from a survival standpoint, I think it has to happen too. As you're trying to get into a new market or sell a new product, the owner or the founder listens and hears a different conversation than a professional salesperson.

I'm not saying they hear a different thing than the best salespeople. The majority of salespeople hear something different in a note or a founder does. So let's just say that, Ray, you're getting into a new line of work with it or MSPs, and you're sitting down from a potential customer and they ask you something and I'll just make this up.

They're like, do you install AI recording devices or recording technology with SDRs? The traditional salesperson, what they do one of two things. They either say no or they run back to Ray and say, hey, Ray, if we could do we need to do this to get this customer. So now we have a product problem because we don't actually know that that's what they want.

They've asked a question. So what the founder does better than anybody is a founder leans in and says, this is really interesting. Why are you asking about that? And they start to uncover maybe there's this knee or this demand in the market that no one looked at. Maybe they find out, hey, we can go deeper and wider with customers doing this.

That's why if you're pivoting your tickets in the new to market, the founder has to stay really close. The final reason is everybody wants to hire some sales guy or sales VP or sales woman to come in and just do it all for them. And the truth is, a lot of people are not. It's rare to find the person who can build it and then do it.

I can kind of tell you what to do and I can kind of guide it. I'm not going to be the one to do it on a day to day basis. They're really looking for free people in one. But no one can make the strategic call that an owner or founder camp. On what direction are we going to go or how are we going to invest, and what do you expect someone to come in and just figure all this out for you?

It's a fool's errand. They can't because you have to do that as the founder, and you have to know what enough to know when somebody be asking you. So I think a lot of people get sold on, and I can't tell you how many times I've had this conversation with a CEO who says, well, I brought in this person to take care of sales, and they didn't work out or they couldn't figure this out, but somebody really sold them a story of like, I'll do this for you.

I'm a great salesperson for a CEO or a founder or an owner who didn't like sales. They were so glad to give it up somebody they thought had magic fairy dust. But if that CEO was just a little closer to sales and did a little bit more, they'd realize, I think you're for crap. And I do think there's a time to to hand it off.

I also think you hand it off it's stages, uh, and you hand off certain things to certain people so that they don't break it because you you break that revenue engine. Man. That's expensive.

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I know you've done some some work with Dan Sullivan, strategic coach, and he has a book that I love who not Howe. And so some of the pushback I get on that is, well, hey, I get it. Right. But, you know, Dan says, you know, just just hire who like you don't you don't you don't need the house. I should just hire people to do all this stuff.

How do you how do you reconcile that the who not how with with that process?

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I think you have to know enough

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to know how to identify the who. Because again, there's all these things we take for granted. So, um, if you and I were talking and somebody said, let's just pretend they've got a brand new technology that they want to take and they want to sell to them and just pick a customer, right? And they want to sell this brand new technology to this type of customer.

And they say, I'm just going to hire a sales guy. You're like, well, have they ever sold a brand new technology? Have they sold at this price point? Have they sold it? This customer? Uh, have they sold in this sales cycle? And if they can't answer yes to at least some of those, you'd say, well, what makes that the right who?

A lot of times we have these just rules of thumb that create massive opportunities for some people and get other people into trouble. And when it comes to the sales person, there's, you know, there's the builder. There's the architect. There's the manager. There's the chief revenue officer. There's the strategist.

There's the person who goes and wins you. Early accounts. It's very rare to have one person can do all those things, or even remotely all of those things. We're hiring anyway. Right now, I want my I've kind of done some work and put in the other process on that and identifying what you, this person, to do. I'm not the right person to hire the person to work for me, because I've got my own blind spots and I know it.

And so I need other other who's to help identify and hire that here. And if your clients, they're better off with the who, not how having you hire those who's because you know what good looks like. They have no clue. They can't build your it. You can't build their IT process. They could do that better. They're the who to do that.

But the devil's in the details on that. Who know how when especially when it comes to sales marketing, right. How many people do you know who've been ruined by a bad marketing firm? And they said, we can do that. They're actually really bad at it. But it was just like it was a line of service they could offer because it, you know, it subsidized the low margin stuff they're actually good at.

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Yeah, that's a good point. The like having having a baseline knowledge and a to know who the who needs to be is is kind of a prerequisite. And the best way to do that is to do the damn job. Like if I mean, if you if you get in and do the job for a while, do the sales for a little while. You don't have to be the scalable sales person, but you're going to have a hell of a lot better idea of who the person needs to be, what they need to do, what success looks like.

If you've done it for some period of time.

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There's frankly, they're just times that somebody, a customer needs to hear from the CEO or the founder. So I'm curious, what have you seen about the different types of sales leaders MSPs need based on the stage, their end of growth? But you've got a you've got some thoughts on that.

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Yeah. Based on the stage of growth, I. I would say that depends on how you break down the different stages. So let's call it 0 to 1 million. One to 10 or 20 and then 20 plus.

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Oh you think 1 to 20 is like you've kind of got that as one kind of category?

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Yeah I mean you could break it into subcategories. I mean, you could see like I, I can see different points like 1 to 5, 5 to 10, 15. In fact, to be more accurate, I'd probably say two or 3 million to 20, like, you know, like the one there's just some resources to invest and shit like that. But I think the, the leader that you need at 3 million is if you're, if you're hiring a real sales leader, like typically like if you're at 3 million, you want to build a sales word.

What I would recommend is you kind of bootstrap it. Like you've got two approaches. I can go hire a sales leader and trust them to build out the sales. Org. Vast majority of 3 to $5 million companies, even 10 million companies are not going to have the cash flow and the patience to hire a real sales leader and then give them the runway.

That's necessary to build a true sales order. Typically, what you're going to see is I'm going to hire kind of bootstrap. I'm going to I'm going to systematize out the prospecting half of it. Then I'll systematize the the discovery and closing part of it. And then and up until that point, the owner is the, the sales manager.

Right. Or they're hiring us or somebody else like to be that manager at a certain point. Call it 10 million, call it 20 million. There needs to be in this. From my experience, there needs to be almost a CRO level kind of mindset to it because you're starting to build an actual an actual sales org, and the processes and the systems that are driving it are more important than like the just, hey, just give me the results.

In the short run, it probably mirrors the technical side of it to some extent. You know, like a lot of these founders on the on the IT side, they were the IT person originally, and then they hired out some of the lower level tech stuff, and then they hired in probably their first real tech and they got to step out and be manager and then, you know, and then it goes on into sophistication as you grow.

Well, if you're running 20 million, you know how to run a PNL. Do you know how to budget? Do you know how to hire a sales manager? Do you have a manager manager? Um, so the skill set, I think just just changes over time.

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But one of the things I've started having telling clients is they're saying, hey, what do we need to do? And I said, hey, look, take our fees. What you pay for. Pay us out of it. When you think about what you want to do. And I will tell CEOs to go sit with your CFO or your book. Whomever they they turn into probably needs to be a CFO level person.

I said, you want this level of growth. I said, I'm not going to tell you this. I could I could look at your books and I could talk about it based on the economics. But you need to ask yourself, what are we willing to invest to get that growth? What made me think about that is, you know, you're talking about we bring in a really good sales leader.

Well, certain ones are going to have expectations on the level of investment around them. You might say, hey, I'm willing to spring for the sales later. Well. Are you willing to spring for the technology they're going to want? Are you willing to spring for some of the other resources they're going to want on on marketing?

And so I think that you've got to get owners and CEOs to start thinking bigger than just, hey, we want growth. To ask the question, how are you going to invest to get that? And I'm not telling you exactly where to invest yet. What are you willing to invest to go buy that growth that actually helps you line up with?

You know, I bring in a sales leader and I say, look, you've got $1 million budget to get where you want to go. Start showing me how you're going to allocate that. I'm not going to tell you you're wrong. I just need to know how you're gonna think about it, because you're going to want everything. This is your budget to work with to get there.

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What do you think? So we've we're in the sales world. We know each other's kind of sales approaches. What do you think? If anything you and I disagree on sales about.

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Let me say this. This is that this isn't going to be a disagreement. This is a stylistic thing. What I would probably I would like to adhere more toward to your end is more of, uh, getting even more rigorous in process. I don't think this would be a major disagreement. I think this would be a difference in the types of companies we work with.

I'm working with companies at various stages, you know, work with a company who's got 400 million in revenue. We work with a company that's got 30 million in revenue or company 5 million in revenue. And the thing that I have to think about differently, and it causes me a little bit of angst, is how do they get the outcome with the resources they have?

And there's a lot written out there that says, all right, go hire the right people. Well, you're not always in a position to just clean house and start over. Sometimes you just got to make do with the people you got and you can say, you know, remember when, um, predictable revenue, not repeatable revenue by agreeing, but predictable revenue was written and everybody thought, let's go hammer that process.

And that's what we need to put in place because this guy wrote this book and he grew Salesforce. So we're going to do that. Is it going to work with your resources? Is it going to work with your market. And I don't think that's probably a big philosophical disagreement. I think it's more of, uh, it's more dictated by the markets we serve and I work with.

I've worked with companies in very limited markets. Maybe they have 500 a thousand total customers. Well, you can't run a seven touch system with stars because you'll call everybody in a year. And then what do you do next? And you have to think about it differently. I think it's what's probably more our market in just our natural wiring.

But I would love your level of organization. I would probably know where to find things in my drive.

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My systemizing, everything that I can, if that's the right word, is really the. It's the equivalent of me keeping no junk food in the house, because I'm really I have no willpower. It's I'm actually not organized and I'm completely like undisciplined on so many things that I have to I have to systematize virtually everything in order to to get the outcome that I want because I'm I'm undisciplined.

You know what I mean?

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Here's what I really want to know. How do you and your wife, how do you get your wife and kids on board with no junk food in the house? I think that's the bigger thing that we need to answer on this podcast.

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Well, we're not batting a thousand on this like we I what I do is it makes its way into the house. Then I complain about it for the two weeks that it's here, and then that particular product is out of the out of the rotation. Then another 1st May find its way into the rotation. I'm like, how in the hell did this get here?

And I complain about it after I eat some of the junk food and then it's out of the rotation. So I think over the course of years and years, what's happened is I've one by one, like kicked a kicked the most egregious products out.

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What do you think on in sales that you think about differently than other people? You know, I think that's that's maybe the real question.

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There's a big debate, especially in the IT world, about like introverts and extroverts and so many introverts. Who are IT business owners oftentimes believe that sales is just an extroverted activity, that it's just like, hey, if you want to hire a good, a good salesperson, you've got to go hire somebody with a ton of charisma.

They'll kiss all the babies. They're, you know, extroverted. They can, you know, shake everybody's hand and do all that shit. I think both both can be highly successful. So it's not like an either or. But I find introverts tend to be more successful, if at least at least as successful, if not more, because their intentionality in the relationship.

Not that it's cold, but it's much more intentional, right? So you send an extrovert to a big chamber event or a local networking event. They walk out, they've got 20 new friends. They feel like it was a home run, but deals don't go anywhere. And introverts walking through that same event and saying, Adam, are you in my mirror?

And subtly like or, you know, not out loud and then saying no, because they're they're there with them on a mission like they're not there. The the event itself is not the reward. And a lot of super extroverted people who you think are going to kill it in sales, end up just wasting a lot of time and building big Rolodex of things that never move any deals forward.

Whereas like introverts tend to be very intentional about who they're talking to, why they're talking to them, where they're going. And so I'd say that's that's one that, that I would, that I'd say is I get challenged on that.

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Well, and again, it's these rules of thumb, right, that if you can help them dismiss the rules of thumb. Uh, mine is

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and it's in the same vein, people say, well, I want to hire somebody who went to these schools, and then I'll I'll clarify that in a minute. Or they were in a fraternity or sorority or they played college sports. And I have and it's in the same it's in the line of, I want to hire somebody from a big company. And I say, well, you're from a little company that no one's ever heard of.

You're going to hire this person from this company. What do you think they expect you to have? And then I'll say, you know, hey, I love athletes. Um, I think it's great. I coached sports, I coached my kids sports. What do you think is the correlation between being a college baseball player in sports and selling and.

Well, it's it's, um, you know, it's competitive. I'm like, well, do you know if that person is competitive with others or themselves and if they're competitive of others, do you have a competitive culture? Because a lot of people talk about competition, but they don't actually have a competitive culture set up, especially smaller businesses.

Right? And then it's, hey, what exactly you need this person to prospect? What have they done ever in their life that makes you think they can go talk to strangers out of thin air? Those are things that I. I have to challenge because people just have these rules of thumb that aren't based on anything. It's just kind of what people have said and they've kind of fallen into it.

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Well, you make a good point. The rules of thumb, um, they can be they can be a great source of information and good advice, but they can also like, hey, it's not paint by numbers. Like the you don't always paint blue here. Like it's just not the case. There's context everywhere. Um, so I'm doing this. I'm doing the research for this, uh, for this interview.

And I read that you saw the sonogram of your of your first child, and you you it was like a turning point. You went. And if I read correctly, you tore down the tore down a vision board. The only thing on on the board at that point was the sonogram. True. True story.

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Yeah, absolutely. I we I'm trying, you know, when we write something, uh, because now I've got some people helping me put, you know, put it all together, but, like, these are my stories. Um, I think there was one one time that was sort of a composite, but that was mine. I was I was cold calling. We were in the sales training business, and, you know, we got married in October and found out we were pregnant in January.

I mean, it was not part of the plan. And we thought, you know, we'll be married for a couple of years, do all these fun things. We find out we're pregnant. And I'm like, something flipped, like a switch flipped. And I'm on a call with a guy. He's running a company, and he tells me, you know, my revenue dropped 70% last year, and we talked for a little bit, and I said, do you want to see if we can help?

I didn't ask him for a check. I didn't ask him to sign a three year agreement. I said, do you want to see if we could help? And he said, I don't think so. And I knew it was sort of a gut check moment. That's like an MSP who is struggling to get past $2 million. The guy has been stuck there for five years. His marriage is on the rocks because he's stressed and he doesn't get home to see his kids, and he can't figure out how to get out of sales.

And he's wanting to fund his kid's college fund. Talking to you with your background and your success level. Actually, this is that's a more exaggerated version. But then when you ask him if he wants your help, says, I don't think so. I remember where I was in my office. I had a little cubicle at the time, probably different universe, like we had been over.

But I'm standing there in this cubicle, and this guy, he'd been referred to me by someone we both know and trusted, and he says, I lost 70% of my business. And I said, do you want to see if we can help, he said. I don't think so. And I looked at that sonogram and I thought, okay, I know what this guy said is don't.

And I'm not going to tell him it's dumb, but I have to be willing to ask him, saying what he's thinking, because this is just it's not just, yeah, I can help this guy, but I also, if I'm going to sell, I have to push through moments like these. These aren't major objections, but I have to push through this because there's somebody who is going to depend on me.

And I'm walking to the sonogram and the kids, and I'm thinking, I gotta fight for this kid. And I said, hold on. Yeah. And this is literally what I said.

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You're telling me you lost 70% of your revenue? This is what I do for people. And you're telling me you don't want to see if I can help? And I've told this story multiple times, and I always ask people, what do you think? He said? And they said, no. He said no. He said, okay, let's get together. And it was sort of this watershed moment of, for me, you just have to fight through some things and it's not even a fight.

It's just you don't pick the first thing they say at face value. And I had to have somebody depending on me for me to kind of make that that leap. And there were my kids have kind of really been a big gift to me in terms of breakthroughs in my life because I, you know, I was in one relationship with family that wasn't super healthy, healthy.

And they treated my kids bad. And I was like, all right, that's a line you can't cross. I wasn't willing to do it for myself. I was willing to put up with it because I'm like, all right, this is what a good person does. But when they messed with my kids, I was like, that's a line too far. So my kids have kind of been this reminder or this catalyst to make harder positions or to grow a little bit.

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I do definitely relate to having people depend on you being the the motivation. And sometimes that can be a team, right? Like it can be. It can be your kids. And on your personal side, I find the same thing on the business side, it's as a solopreneur you can you'll make different decisions than you will if you've got five people on payroll, you know.

So sometimes we need people to kind of to kind of push us. I, I respect you as a dad, like as a family guy. I know, I know Aaron and you guys have been out here. I'm curious because your brand is simple, like it's I mean, it's for as far as, like, sales strategy. It's like the way you communicate. It's very it's smart and simple.

But if I look at Adam, like, as a whole, you're an active dad, you're coaching football. Your father of four, you're running a consultancy, you bought a company. I think you're you're also part of peer groups. And, you know, who knows, maybe maybe more acquisitions. How do you reconcile simplicity with the complexity of life and practice?

Like how does that how does that relate to you?

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You know, if I think about it, I had this problem for years where I compared myself to other guys, whether they're in a tech startup or they had these big exits or they work for private equity firm or they do these sexy things. And I would say, ah, I felt like, oh, I'm not doing enough. I had somebody probably like you ask me, what's your what would you do differently?

And I hadn't even thought about it. And I was like, well, I don't. I had to think, do I want those that life? Because there, there are a lot of people who

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look at someone else's life and think, oh, that's great. They don't realize, well, they're never home. They're working 18 hours a day. I had a I had a client. He's now a CRL, a massive company that recently in public. This guy's life. I love the guy. Zero interest in what he's doing. He's on calls from 6 a.m. to 2 p.m. and, you know, it's backs of mass because he's he's sitting or he's at his desk all the time and he can't get out.

He's literally on calls with tons of pressure and working for insane people. And I realized, I don't want that. And when it comes to simplicity, I started realizing, okay, I can build a really good business with people I really like. We can make great money and have a lot of fun, and that affords me the margin to go be more involved in my kids lives.

And look, I'm gonna be honest. Right now, we're running the two companies, we're merging them. We're growing, we're adding team. It's a bit nuts. I'm working on proposals at my kitchen counter at 9:00 at night, until I can get some people to help me with it. That's where we are. But I need simplicity in some areas so that life can be more full than others.

And when we talk to companies about sales, it's your sales cannot be so complex. I kind of think we only have so much brain space available if your product is really complex, if the market's really complex, if you need to know these things, something's got to be simple so that people can do it mindlessly.

And I try to keep our business simple because then I can communicate it and I can manage it, and I can get other people into it. And eventually I can, you know, go to the next part of the business. Yeah, I kind of want a simpler life because I want to spend more time with my kids. We're going on spring break next week.

Thing I'm most excited about is I'll have three meals a day with my kids. I'm not on calls, not meetings, not talking to clients, not solving problems, just hanging out. And so I need simplicity to create that margin.

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Yeah, I appreciate the transparency too, because on like deals at the dinner table, because that's the case right now for for me too. You know, like with, with growing a business, there's just there's, there's a, there's a cost to getting what you want. And so, you know, determining what it is that I want and what cost what what I'm willing to, to invest to do it.

Um, when you see, like, on social media, I know you're active and stuff. When you see somebody talking about, hey, business ownership doesn't have to be hard. Like, you can do it in four hours a week. You can do this. You do this. Do you think I'm doing this wrong? Or do you think bullshit like this. This is not the.

That's not. That's not the reality.

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There are people who

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who've kind of gotten things dialed in and said, look, I've had enough experiences meeting the people who did that that I really looked at. and then you find out the other side of it as an absolute disaster, and you kind of start questioning almost everything you hear. I pretty much like to listen to people that I that I know and trust now, like, I've seen your life, I've seen how you do it.

I'm aware of some of the things. And I know that, like, what you talk about is not B.S. you've lived it, you've done it. You've got the school of hard knocks. I think there are people who can get really good at it, but there's a lot of like, you could do it for hours a week. And I think

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how I saw one of these reels on Facebook or something on LinkedIn. And this guy, he's talking and he's one of these guys, and I own 82 companies, and I run 82 companies. And I can if you have a right system, you can do it. And I'm thinking you and I probably know a lot of really brilliant LPs at, you know, private equity firms, sharp people, none of them are trying to run 82 companies.

None of them. Um, because to do it well, I mean, the level of organization, you'd have to have those companies be strong, enduring, profitable companies is just off the charts. And I hear things, too. I, I kind of think, ah, that that's bullshit. There are other times I'm like, ah, there's probably something I can learn there.

So I want to stress test it and find it. Well, how do you do it? What are you doing? And then I've seen enough to know that. I've seen people are bragging about their business and what they do, and they're building their personal brand. Meanwhile, they're engaged in fraud for their business. So I, I try to look at the whole person and say, hey, do I kind of like your life?

What? I want to be like you and learn from you sometimes it doesn't have to be that case that way. But I'm kind of looking at the whole thing to see. All right. Does this does this seem real? I'm a little skeptical, but yeah, business owners is hard, man. And, uh, I think somebody was saying you're not an entrepreneur until you've missed payroll.

We've not miss payroll meant good, thank goodness. But I've laid in bed saying, what's going to happen next month, you know, to a, um. And I don't think it happens as a solopreneur, but when you take on people and you're dealing with customers and you're managing working capital, it starts happening.

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Being a parent and being an entrepreneur is one thing. Being a parent, being an entrepreneur. And then like, if you are the sole income earner too, like it's just it's a whole nother level of, of of stress that, that unless you've done it, it's very difficult to speak about it.

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I remember having this conversation with me said, do you realize the average age of a founder? And at the time, I think he said it was 45 and maybe the number is 42. If you're at 45, you're a little more successful. And you think that's kind of crazy because there's a part of me that would say, go try and start a company in your 20s.

You have all the energy, you don't really have any risk. You know, just go do it because you know, you're you make it really smart, but kind of dumb. You might lack in wisdom and experience, but, you know, if you blow it up by the time you're 30. Big deal. Will just start over. But once you're, you know, you you pick up, move everybody to Mexico.

I had to figure it out. And there's some great stories that you shared. Families depending on you trying to make it work. There's different level of something there, and a big pile of cash makes it easier, but not always necessarily right. Because you're still wondering, can I get it done?

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A couple last questions here, I. Are you still coaching?

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I am coat my my 14 year old talked me into coaching his flag team and, uh, I made him organize it. But I am coaching, and, um, I probably think about it more than I should.

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When I look at coaching as a, as a profession, one of the things that fascinates me is how coaches managed to get their philosophy and their system installed across a team, and how much, how much similarity or not there is to a CEO that's potentially trying to take their vision and get it down to the team and a coach trying to get it out to the team, because you have all of these things in between.

Like maybe you have another manager or another coach involved. You've got different talent, you've got actual execution, you've got opponents. How similar is that? Is it is that a fair comparison or.

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No, no, no, I think I think I do think it's fair and I, I love this question because it's you've had a couple zingers here that have got me like, all right, I need to go think about this. Currently, I'll coach my eight year old in flag football. Got some great stories about that. He got flashed twice in our championship game last year, one for unnecessary roughness.

The other one was for spiking the ball after he scored two flags. One game. My 14 year old, I coached him. I used to coach high school football in high school or just in, let's just say an organized sport. One of the differences is you. You have multiple practices a week where you have the ability to repeat the same mantras.

And if you're the head coach, you're constantly repeating with your. Your your assistants. These are the things we're emphasizing. These are the things we're emphasizing. And a lot of times, you know, even football it's. Offense defense and special teams that's still pretty manageable. You you don't need to be the one calling the plays and doing all the X's and O's.

But you kind of emphasize these things, these things, these things. And I would love to see it more in companies. A couple challenges I don't think it's impossible, but I think all right remote becomes hard because there's all this stuff. I'm not saying we're most wrong. I, I'm bad at it because there's all this stuff where you just don't rub up against each other in the break room at lunch.

I can't just open your door and ask you a question. I got to get on a zoom or I got to give you a call. So I think that's hard. And I don't know how to do it, but someone does too. I think for the CEO, one of the challenges is there's so many groups and constituents, constituencies that you're trying to manage and take care of.

There's there's sales, there's marketing, there's ops, there's finance. There might be delivery or customer service. Depending on how you break that out. There could be investors, there could be M&A. And you're trying to woo all these people. And I think if you're not really focused, disciplined, the message gets diluted.

And one of the things that we really try to help our clients with and you try the same is hey, what don't do a flavor of the day like pick it and and commit. And

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you've got to emphasize things because you're trying to shave thinking you're trying to shape behavior and trying to create a culture. You know, people ask me, hey, will you do a sales kickoff? And I'm like, I mean, I'll do it. I'm gonna charge you a lot and I'll do it. I don't expect anything to change, but they bring somebody like me in or you or Alex, and they're like, all right, get us fired up.

But I'm like, that's not gonna last. And you're, you know, if you bring in Ray and then you bring in me, and then you bring in Alex. What kind of thought or principle or framework do you expect

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to stick?

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It'd be better off and you guys got up and just repeated the same things all the time. Start shaping the culture and creating the mindset. And, uh, that's what I would love to see more of as applying that. I, you know, Notre Dame is famous for having the sign in there. Uh, Lou Holtz put it up. He just died to the day in the tunnel.

It said, play like a champion today. And the players slap it before they go out. And there's one of the things I've tried to work with certain companies on is like, you need to have a mantra that you guys live and rally around. And I used to tell people like, if you're in a market where you might call on somebody for free is where you get them, you need to have a sign in the offices, I'm going to get you eventually, and you guys just need to slap it before you go out of the office.

Okay? I'm getting you guys me a mindset, but you have to have people really committed and clear on what they want, and they've just got to repeat it. It's absolutely doable. If you can stay focused. If you know what you need to do for the various areas of the companies, at least sales and marketing. Just get clear and don't get distracted by shiny objects.

So hopefully there's something in there for someone to kind of tease out and just say, hey, I need a lesson. My life. I don't need more. Quick story, because you got me going. And, uh, there was a there's a guy on my team and he's asking me what sales books to read, and I'm like, stop. You don't need to read any more.

I need you to go deeper on the two that I've given you. Let's let's master that and then come talk to me about what else you want to read. You don't need to be a mile wide, an inch deep. Just go a mile deep on a couple things. Let's get great at that. And then let's see if you need anything else. And that's the same thing with CEOs and running companies that just get really good at a few things, master those, drive those in just in the sales work, and you're going to have a lot of success.

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It's a good reminder for for CEOs and leaders of any type that are prone to more ad mentality because I which which I am like a mile a minute ideas. You have to develop some kind of filter or some type of system to create a barricade between all these ideas and all these things that may be happening, and not letting them get to the team like I used to make the mistake, I'd walk in the door as my first CEO job, and I'd walk in the door and I'd be like, all right, guys, just read a book.

Execution. That's basically it's your flavor of the day. It's like, that's the theme of the week, like execution, execution. And then the next day you come in and it's like, read a strategy book, guys. Like, we got to get better at strategy. And so you would do this. And what I found was it wasn't necessarily wrong.

Like I was feeding my own desire for a bunch of information. The the challenge was I needed to develop the discipline to not feel the need to share that with everybody. When that comes back, either, I either I have one person that I dump all my stuff to and they say, cool idea, Ray. We'll add it to the list. Right?

Like of everything else. Or you just create a system that says, I'm going to put this over here for right now. And if I still think that's important in a month, maybe we can we could chat about it. But it's I think there's a there's a discipline built into that, you know, for, for leaders to.

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Well, I also think it's clarity. And one of the things I've seen in working with you, and I bet you're really good with your clients on this is you're really clear on what matters and whether it's your values or your pillars. You just kind of come back to those and you can determine, does this help this or does it not?

And you're you're an entrepreneur. You're an enterprise. You're always going to see opportunity. But the thing that you're also good at is here's what I'm working on, here's why I'm doing it. It's kind of why you started certain businesses. Initially it didn't seem clear, and some of these people just are not.

They're kind of like, we want more sales. Okay, well, let's just go read a bunch of books. Well, are you executing? Do you have an operating system that you can fall back on, that you can fit all this in. Do you have a way to train people? Do you have a way to coach and develop them? Do you know what you're coaching and developing too?

Because otherwise you're just going to be all over the place. By the way, I'm having to learn the same discipline with my team is like, I can't just throw up a bunch of ideas and it's like, it's gonna stress them out. Especially really execution oriented people. They're like, settle down. So I, you know, maybe I can sort of support group where we just share all our ideas and.

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Well, it's I, I believe there's a selection bias in the type of people like what we do for a living. It's probably not uncommon. Our minds were racing a mile a minute, were creative. We have these ideas. We're not we're not complete idiots like some of them are really good ideas. But putting those into some triage process, where is this ready?

In fact, I, I, I watched a video of Bezos and what Jeff said was his COO or one of his operators, the operators, the person who was in charge of building out the manufacturing, the distribution and a lot of the stuff on that side of Amazon, early days told Jeff said, you have enough ideas to kill this business if you don't stop putting those ideas out to the floor.

You're developing a backlog, right? So think about it in terms of manufacturing. You're just dumping all this like work in progress. That's that's happening, which means none of it's getting done efficiently. None of it's getting done effectively. And you're confusing all the people who are supposed to be doing this shit.

You're going to kill the company. So you need to figure out a way to release your ideas at the rate that the company can absorb them. And that's stuck with me. Like watching that video, it's like, damn, because I learned that lesson the hard way. I did the same thing, you know? And it's still to this day, I have to pull back sometimes, like I'm doing it again.

Fuck. Sorry, guys. I'll slow.

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Down now. That's really good. My work. My words for this year are focus and finish. And you know, I'm meeting with our team Friday to kind of plan next quarter. And I've learned I need to think about what can we do. And I'm limiting what we're trying to do so that we can actually get it done. And I'm actually not I'm going to talk about sales and marketing.

It's just operations and delivery. That's all we're going to talk about is what needs to happen around operations and delivery, because I'm going to go work on sales. But and we're going to continue to grow, but we've got to be great there, and we're going to limit the scope to be great. And that'll allow us to grow layer.

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In our business. Through the MSP business, we have about 30 SDR who are in South Africa right now. And so we're actually potentially planning a training in Cape Town, uh, this this summer. And I think Cabo may be a good mastermind type event come, come winter. So potentially I'm not committing to it. I'm not saying yes, but yeah.

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No. Okay. Eventually I like it. You seem committed. Thank you. I'm glad you committed to that. Appreciate it.

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Yeah. No. Speaking of, like, ideas of mine, like, dude, I'd love to do it. Um, but I. I've got to be better about committing. You know what I mean? Last question here. Your. Your entire careers. I can read this. I can see it from the outside looking in from high school English teacher to football coach to sales trainer to company acquire, it seems to follow this path that I see of teaching people how to get better.

Like that seems to be something you're just good at. And my my question would be, who was most influential in teaching you to get better?

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There are a handful of the most influential people in my life. Every single one of them was in a role of teacher or coach. Every single person who's been incredible, they literally were a teacher or a coach. And I had one really good teacher in high school. I had a great coach. I named my son after this coach, this great story there that we'll talk about over margaritas sometime.

But, um, we actually went to Italy with this guy, and, um, he put together this phenomenal trip for me and my son and him and, uh, and then I had a really I had a couple really, really, really great teachers in college. Um, one was an English teacher, one was a philosophy teacher, and one was a sociology teacher.

And then I had a really good pastor again, a teacher. I had a couple mentors who were truly trying to teach in my early 20s. And then in business school, I had these world class teachers. It was incredible to me that I never put this together, but they'd be most influential. People who've put their fingerprints on my life were all teachers and coaches.

Uh, and there was bad ones. There were some very mediocre ones, but there were a handful of people who were just world class, and they changed the way I think and approached life and helped me kind of see some things and put some skills together. Um.

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So I would say a few people stand out. I one is as a, as a kid. So my, my childhood was kind of like it was. It was very volatile. There was a lot of changes. And I had one person named Troy. Troy Lewis, he's written a book now, and he worked for my mom. He was in the Air Force, worked for my mom, and for no reason, no reason, no obligation, no.

Like, he knew I loved basketball and he just became like a second dad to me, like. And we just he would take off. It was so cool. He would take off. He saved all of his time off in the military for, uh, for March Madness, for for basketball. And he had walls of videotapes, and we would come over and just watch the shit out of North Carolina and watch the shit out of, you know, Michael Jordan and everything, that that was where my my love of basketball came in.

But he stepped in, I think as a mentor, as a as a man, as a just a good person. And we're still we're still in touch and and text every time Carolina plays plays Duke. And I would say the second one, I had a few people. The chamber experience was really, really influential for me because there were several people that believed in me more than I believed in myself at the chamber.

And and so, like the the VP of sales that promoted me into management well before I should have been promoted. But I wasn't the top salesperson. I didn't have a degree I didn't have. But he said, now you're you're the guy and put me into a role that I wasn't even sure I was ready for. The COO at the chamber at the time, um looked at me one time and said, hey, this next promotion, you need to get a bachelor's degree.

We'll buy it, but you're going to have to go full time and do the job. Are you willing to do it? I said, fuck it. Yeah, look, let's do it. She was kind of responsible for ascending me through that whole organization, and every time believed in me more than me. Like, hey, you know what, Ray? You can do this next level thing.

And I was like, well, that's a big title. That's a big thing. And and yeah, so looking back, I'd say a couple people. That's pretty cool.

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Um, that's all.

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So when you're done, what do you want to be known for?

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It's funny, you talk to these people and they think about legacy and, uh, they're like, ah, you know, I want to build this great company. And,

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you know, I want to I want to do great work, but I don't need to write the great American novel. The thing that I really probably want to be known for is, uh, I mean, there's part of me wants to write the greener, great American novel and, like, sit on the beach, but, uh, I'm not there yet. Uh, man, I really want to be known.

It's kind of divided, but it's very similar. Um, there's a song by a guy named Josh garrels called, uh, at the Table, and it's basically a father singing to a prodigal son who's come home and says, hey, you'll always have a place on my table. And the thing that's probably most valuable to me, and the most important thing I do is that time my family, as we're on the table and I, you know, I've got like a six year old, an eight year old, a ten, you know, a 12 year old, a 14 year old.

They're kind of yelling and all talking to each other, and it's great. And my, my dream is in 30 years. Right. Well, I'll be, you know, 75. Um, that they're all at that table together with their spouses and their kids. Right. That's really any legacy is just them staying together and loving each other. And then.

And hopefully the thing that I'm, I'm known for is, you know, I was faithful to what I was called to in terms of my faith, my family. And I loved people really well. So, uh, I'm not like, the warmest guy, but hopefully, you know, if you talk to if you talk about me in 30 years, you're like, man, he's been a great friend to me.

So, you know, all the other stuff. I think we do good work and we focus on that. But that's not what I want to be known for.

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Thanks for sharing, brother. Thanks for coming by. Appreciate your time. Look forward to doing it again.

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Love. Love it. Can't wait to do it in Mexico.

About the Podcast

Show artwork for The Ray J. Green Show
The Ray J. Green Show
Sales, strategy & self-mastery from an operator, not a guru.