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Chris
If you can be a compassionate leader and show empathy and be willing to be tough and candid, but be human, nobody wins from this or berating. Nobody wins in any of that leadership styles anymore.
Ryan Hogan
Welcome to Confessions of an Implementer. I'm your host, Ryan Hogan. We share unique stories of EOS implementers and the companies they've transformed to give you a rare glimpse into the successes and challenges of the system in action. Let's jump in.
Ryan
We've got a ton to talk about today and I don't have like a necessarily an end state or a desired state because your story is so incredible. And I think I told you before we hit the record button that I don't do big intros. However, I just want to, I just want to point out just a few things that's in your background. You've got former expert EOS implementer. You've got the co founder of 90, which by the way, we were an early adopter with Hunt, a killer at 90. You've got co founder of System and Soul. You've got executive coach, founder of Micro Business Academy, co founder of Profit Pro. First question leading up. Do you sleep?
Chris
Yeah, I do, I do, I do because, because I've learned to use this little thing called the egg timer. So I kind of blocked my time and you know, listen, none of, none of those things you mentioned did I do on my own. I had partners, phenomenal partners that continue with those programs today and hats off to them, they're doing a phenomenal job. But I, you know, I really enjoyed my time at EOS. I think I was there 10 or 11 years and you know, while I was there, I came from a SAS background. I had already built two SAS companies and sold them. So when I got into, when I got into EOS with Gino, you know, they had this wonderful book and, but there was no, it was all paper based and so one program had come out. But then I approached Mark Abbott and I said, hey, we can do this. And, and you know, my background in SAS helped and I eventually left. I got some pretty serious health issues and exited. Mark is doing a phenomenal job running 90 and so is Benj Miller at S2. Another. I feel like I've sort of been a part of giving birth to two operating systems at, you know, 90 and S2. And you know, one was built for an existing system and one was built to evolve. And neither, neither one of them are right, wrong or indifferent. It's all based on the end user, right? What they need. But they're great programs. I was proud to be a part of them and definitely proud to be a part of my time at eos. My goodness. I'll tell you kind of the quick story because it is a full circle story and it's really meaningful to me. Even though I'm no longer affiliated with eos, I was working, making very good money, and I was bored stiff. But having grown up in an entrepreneurial family, I'm the eighth of eight boys. My grandparents were entrepreneurs. My parents built two businesses. My perception of entrepreneurship was, no, thanks. I never saw my dad, like, kind of like, did you sleep? My dad worked a lot. Of course, having eight kids will keep you out there, but it does take a lot. And so when I had the opportunity, I got a phone call from a business owner that I knew in New Jersey. And he said, hey, I'm going to implement this system and I'd like you. He asked me. He goes, I'd like you to be on my board and I'd like you to be on my SLT team. And I'm like, okay, let's let me dive into this. He goes, no, no, I'm just going to send you a book. I'm like, okay, you can see behind me, Ryan. I'm a voracious reader. I got a book called Traction on a Saturday Morning. I never heard of it, and I probably read it in about two and a half hours. And I was kind of like, wow, where is this? You know, like, I was thinking I did very well in my two exits. And I was thinking, man, if I would have had a system, more of a disciplined system, right, that maybe I would have get a larger multiplier, maybe I wouldn't have sold at all. I don't know. But it was really intriguing, so I had to know more. So I called the business owner back in New Jersey and I said, hey, I don't know. I don't know the author, I don't know the system. I've called a lot of people in my network. Nobody's heard of it. I'm all in. So for two years, I sat on an executive team and an implementer came from Detroit and we implemented eos into this $10 million company. And it was transformational. Transformational. And the funny thing is the implementer, and I'm going to give a shout out to Dwayne Marshall, because he was the US implementer from Detroit, Protege Genomes. And he just walked up to me on the very last day and he said, hey, Chris, can I ask you a question? I go, yeah, what's up? And he goes, well, the whole time we were doing this, I just got the feeling that you thought you could do what I do. And I said, dwayne, that's a great recruiting line. I said, dwayne, I said, to be honest with you, I do think I can do what you do. Number one, I've already built two companies. So I've got the dirt under the fingernails, I got the scars on the arms, and I got the worn tread on the boots. I've walked those miles, many, many miles. But the other thing is, I went to school to be a teacher. All I ever wanted to be was, like, a high school teacher and a coach. I did not have these big, like, business aspirations, like, like my dad or my grandfather. I love sports. I love playing sports. I love coaching sports. So that was it. But this book changed my life because it allowed me to. To become a teacher and a coach just at the executive level, as opposed right to the academic or school level. And let me tell you, it just, it was the perfect timing for everything. And over the course of the next 11 years, I, like I said, I built a lot of stuff inside of 90. I had a wonderful time. And when they decided to become a franchise is when we parted ways. We kind of shook hands and parted friends. Everybody knew me for that. Saying, as much as I loved him, again, I'm a business builder. And being sort of committed to a contract of that depth, I wouldn't have the freedom that I need as an entrepreneur. I wouldn't be able to exercise the freedom that I have. My ideas, my vision. I'm really good. Identifying gaps and then filling. Finding the resources to fill those gaps. And, you know, like, I brought radical candor in the U.S. they're like, you can't do that. I'm like, well, you should read the book because it's really good and our clients could really, you know, benefit from it. There's a lot of good books out there right beyond the Traction Library that are, you know, super applicable to our target market clients in that 2 to $50 million range. So. But anyway, you know, I'm an Irishman, so I'll hit pause. Otherwise I'll just keep going.
Ryan
This is, this is the whole purpose. It's just a. It's a coffee conversation. We kind of see where it goes. I. I'll tell you with the, the whole, the whole 90 thing, like, I just got it, like, when we explored the software and like, I'm not being sponsored by 90 in any stretch of the, the imagination but the, the power of that software and being able to organize, because we used to organize stuff in spreadsheets, it was just incredible. And one of the things that you talked about in your story with 90 and S2 and your current ventures and all these different things that you've done has been this idea of partnerships or finding someone else, maybe a yin to the yang. And that's also something that I'm a deep believer in, because when I look back at Hunt a Killer, I never have created a murder mystery game in my life. When I look at the recruiting, I have a certain level of expertise in recruiting just because I built Hunt a Killer at its peak was about 150 people. And I was a part of those hiring processes. But by no stretch of the imagination am I a career recruiter. And so what I do is I go out and I find these subject matter experts that I can partner with and bring my skillset alongside of their skillset. When you think about partnerships, like, what do you look for both from a, like, experience, expertise, maybe passion, and then also, like, how do you pick partnerships that are going to endure over time?
Chris
You know, you certainly have to fundamentally share a core passion for the problem that you're fixing. You know, the minute you go beyond one person, well, now you have multiple interpretations of how to solve the issue. Right? I like that. I like conflict, healthy conflict. Right. I like the pushing back. My, my first partner in my first SAS company had about 140 IQ with a photographic memory. He only went to 3 years of college before med school took them. They're like, come on, you're done. We'll give you a degree. Come on up here. Yeah. And while he was there, he taught himself how to code because he was bored. This, that, that's the guy. Now when you get to that level of brain power, that can be intimidating, right. I do not have 100 IQ, nowhere near photographic memory. But here's the thing. We complemented each other. You mentioned that yin and yang, that coupling, that puzzle piece snapping together. Right. That's. I look for, you know, find people. Always look for people smarter than yourself. Right. Surround yourself with smart people. That includes smarter than you. Right. Just. That has been part of my process. Right. But you got to share that passion. And you know, partnerships can be tricky. Obviously, the, the, the deeper you get into it and then there has to be a level, a consistent commitment to having same page meetings, like staying like really going deep, like being. You build your list, I'll build my list. And we have this, we have this Meeting where we try to solve those so we can leave with some sort of parity. Right. You're not going to always be on the same page. I think the other thing too is you have to have absolute clarity on roles and response, responsibilities and, and again, that's where, you know, when you make these commitments, these are smart people. You got to trust them, you know? You know, great leaders get out of the way of people. They let them move. Right. And so, and, and vice versa. Right. Like when I was with my partner who was that intelligent, you know, sometimes I'd have to grab and say, look, pal, you can't talk that way. You're not making the emotional connection you're missing. It doesn't make them a bad person. But that messaging that rolls out to the end user isn't good. And so there's. There having some tension is okay. Of course, the worst thing to do is ignore anything personal or professional between the partners. If you start ignoring stuff, that's the beginning of the end. You have to be willing to have those owner's meetings, as they call them, right? Where it's a, it's, it's a, it's a safe room. It's not a senior leadership team meeting, it's a partner meeting. And those are different conversations that you have, you know, and they can be tough. But I've enjoyed mine. I would say that I would still be involved with 90 had I not had some health issues. But now I get to go do other cool stuff like what I'm doing now.
Ryan
And have you. I love that. Have you ever had a partnership go sideways?
Chris
Well, you know, some. They always bend.
Ryan
I like that. I like that.
Chris
And, you know, some partnerships just don't work out. And, and when people are open and honest about that, it's okay. I mean, it's okay. If it's no longer a fit, then you have to have the solution. And if that means someone bows out, then you try to do it as professionally as possible. I mean, you came together for a common mission and goal and work together, and hopefully you can exit in that way. Have I had heated conversations? You bet you. I'm @enneagram8.
Ryan
That's actually a really interesting point because you talked earlier. It's. It feels like it's the second time we've kind of came to this, like, tough conversation. And earlier you talked about this idea of, like, healthy conflict. What, what's the difference between healthy conflict and unhealthy conflict? And like, from an outside perspective, like, what are those signals or different Things that you're looking for to say that's healthy or that's gone over well.
Chris
The obvious quick short answer is anytime you cross that line in your language and you go personal, you need to maintain that line of integrity. And when you go unhealthy can be like arguments nonstop just in front of employees, just in bang bang. Like I was counseling some executives last week. They let a small problem evolve into a flare up. And it was one of those situations where of course they both thought they were right. Neither one of them was willing to bend. And they did all of this in front of a handful of employees. And it's ego. And you'll see behind me, I've got a book up there by Ryan Holiday called Ego is the Enemy. Recommend that book all the time to anybody and everybody. It doesn't have to be just an executive. You know, healthy conflict is like, hey, Ryan, I've got to talk to you about a particular issue that I believe that you're involved in. And it might sting a little, but I just want to get it out and I want to have a conversation. So I kind of prepared you for a sting. I don't really know how it's going to land. It might be nothing. Could be a mosquito bite or it could be a 10 pound hammer. I really don't know. I don't want it to be a 10 pound hammer. But it's just being, you know, polite and courteous and aware. You know, I, a few years back I had a situation in my own company where I kind of lost it with someone and that person didn't. They committed to something, said they could get it done. I did a rookie move and didn't double check, you know, trust and verify. And I went to give a demo of a SaaS product and what I asked for, wasn't there. Now I done at this for 30 years, right? So I was cool. The client didn't know. But when I got out of the meeting, I was hot, man, I was hot because I really needed that to be in there. Not to necessarily close the deal, but the client would have been blown away if I had had this one thing, which the programmer said, it will be there. And so I have a coach PhD and I called him and I'm like this employee, blah, blah, blah, insubordination I love. He goes, chris, I want you to read a book. And he, and he holds up this book, the Only Leader is Worth following by Tim Spiker. I'm like, okay, I'll read the book. So he might, he he didn't give me any answers other than go read that book. I got to page 66. So the book talks about in the five years of research, the discovery was there are two attributes that make a leader worth following, and that's being inwardly sound and others focused. And those two attributes have definitions. Okay, well, I think it's page 66. It talks about being self aware. And the definition is you understand the impact you're having on others. And bang. That was the nose punch. I'm like, there it is. That's why coach wanted me to read this book. I grabbed my phone, I'm like, I got it. I got it right here. Self aware. I didn't. He goes, yep, Chris. He goes. He goes, Number one, you're 6, 3, 2, 55. You're a big, intimidating guy. You just carry yourself large. You have this deep, you know, Shrek voice and you just have this physicality about you. And when you bring in your passion into that, you really can light up. Now you can light up a stage, which is all positive because you're, you're really good on stage or you can light someone up. And, and, and again, you lit this person up because you just didn't realize the impact you are having on others. So, you know, now that you know that and we role played and kind of. All right, how would I, how would I handle now having read this? And, and that's really how I learned, by the way, is through role play. I get all these books and then I take the tools out and kind of apply them, right? But, but that book, like, boom. And you know what I did, Ryan, After I had this whole realization, I wrote a 12 minute TED talk and a 45 minute workshop and I was traveling internationally, giving it. Just before I got sick, I was in Dallas and Jamaica, over a thousand CEOs. It's just, I wanted to share my story because I want to be a leader worth following. You know, I don't want to always be the nine pound hammer. And even at the age of I'm turning 60, I still have something to learn. But here's the coolest thing out of that. That whole thing, I had to go backwards. And what I realized is I had learned some bad habits from my father in the way that he led his companies.
Ryan
That's like, you know, and talking about your father and that was really like a generational thing. And even when I joined the military in, it was very, very early 2000s, it was still very much a. You do as I say. You don't ask Questions. There's no reasons to understand the why. And I think over time what we've realized is that as human beings we can get out of people if they believe in what we're trying to accomplish as a team. And so like that philosophy shifted. But that, that was very much, you know, that was very much a generational thing. When, when you look back on that circumstance, because I'm dying to know now, because you kind of, you kind of dropped the seed. Like how would you have handled that situation different with that employee? Like, what was your retrospection? And if you could do it over today, how would you approach it?
Chris
Well, so here, what I've done since then is I send myself to training every year, some kind of training, formal training. This year I'm going to Lieutenant Colonel Scott Mann's storytelling training in, yeah, in March. Rooftopleadership.com Scott Manny learn about him. Amazing man. He's sharing his 23 years experience as a Green Beret with entrepreneurs and business owners. And I'm very, very honored and proud to be his, his coach. But you know, and I learned a lot from him as well in his leadership. Like for example, I love commanders in town. Like, so when you ask what would I have done differently? Well, I would have gotten more training for me. Leadership training, right, like leadership training that's more human centric. So more psychology courses maybe, Right. How the human mind works. Like I love the book Pitch Anything by Oren Claf. The way he has, has done his research, talking to all those neuroscientists and then using framing to set up a pitch. Just little, always educating myself, trying to get better. I didn't do a lot of that in the beginning. And it kind of goes back to your earlier point. Did you sleep? No, dude. And it was, it was put on the blinders, head down and plow. And that's what me and my, my partner did. And they were 12, 14 hour days. I mean late nights, weekends in the first, you know, two years, quite frankly. But even when I think about going as far as back then, I had formal training from Motorola when I was with them. But it was sales training, you know, it wasn't leadership training. So I wish I, I, if I went back, I'd be like, dude, pick a training seminar. One, you know, once, one thing a year, like, go invest in yourself. And I've been doing that ever since, you know, gosh, I've been doing it for a while now and on different things, right. Like this one's storytelling. I want to be able to convey Myself in a much clearer way through storytelling because that's the original, you know, way that we transferred information right after writing on walls and getting past grunts, you know, the evolution of communication. And I think now so more than ever in our world, I mean we need to learn how to, to communicate more effectively, we need to be less judgmental and consider the other person. Really consider, you know, Kim Scott, she in her radical candor, her vertical access going up. You fundamentally have to care about your people and if you do, then you're going to be willing to piss them off a little bit because you're going to challenge them to be better, but in such a way that it's appropriate. It can be. There'll be conflict, but it'll be healthy conflict where hey, we're entering the danger zone, or however you want to coin it. There's all kinds of different ways you can tip off that, hey, we're kind of entering into an area where it's going to go a little meaty here. So let's keep our egos in check and our emotions in check. We deal with facts, we don't deal with theory. Right. Gotta be data driven conversations. Hopefully mostly, but yeah. So anyway.
Ryan
All right, quick break friends.
Ryan Hogan
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Ryan
You talked about this idea of caring and I hear This a lot. I agree with this. And I'm curious in your perspective, like, this, this whole idea that, like, care and empathy is really kind of the cornerstone of leadership. Like, a lot of things can be done. You set the vision. And I'm not saying those things are simple, but like setting the vision and making sure that everybody's on the same page, rowing in the same direction, like, great, we're good. But the cornerstone or the foundation for that that we hear about a lot is this notion of care and empathy. And how do you do that? Because you just, on one hand, you just talked about this idea that, that, like, sometimes you have to enter the danger zone. And if people know you're coming from a place of love or a place of caring, then they know that you're just pushing them for the greater good of themselves and the organization. Like, what are some ways that you can show that you care before you're entering the danger zone? And you've built that trust.
Chris
Yeah, it starts in the interviewing process for me, because, you know, I'm going to show them. Look, we have an organizational chart. And these represent all the functions in the company. And each function, each box has a mission. It has KPIs, and it has roles and responsibilities. And the sum of those are what that seat focuses on. And that's their job. Right? So that's clarity. First super clear, and then expectations, being super clear with expectations. And it's not just your expectations of them, it's also their expectations of you. Right? You got to work together. You know, whether it's a managee manager relationship, you know, the vertical or the hierarchical structure, I think it just starts fundamentally with being super clear on what the job is and what the expectations are and how we're going to measure success. And then the other thing is we live open and honest. Now, that doesn't come easy for a lot of people, Right. You know, some people. Some people will feel like a snitch if they're calling out something they see in a broken process or something. So it all starts up front with the leader, like saying, you know, this is our philosophy, right? Like system and soul, Right? System are all the systems and processes and tools in the business. And then the other people, like, you have to have more than one sixth of your focus on people in your business. Right. And so what do those investments look like? Well, one, you got to become a better leader. You need to become a leader worth following. And so you should be investing in yourself, like I do. Send yourself to some kind of training or Read the next book and, or whatever. And for them, it's setting expectations, showing career paths, showing how you support them along their journey. In your company, you know the cadence of meetings, the cadence of the, the employee, how often you're going to sit down with them, right. And coach them. I don't, you know, call them quarterly employee meetings, monthly. They're coaching opportunities. Now, you still got to be the boss, right? I mean, you gotta, you gotta be the boss. And if you see underperformance, you have to call out the underperformance. But if you've already done it on the front end and had these conversations and set them up, they're gonna come in understanding that. And so when you come in and it's pretty obvious, say you, you know, we gotta have a tough conversation. It's been six weeks in a row, you're not hitting your quota. Something's wrong. We gotta have a conversation. I know, Chris, I know. I've been mean in to come to you or whatever. All right, cool. Let's get in there and let me help coach and mentor you. Let's solve it together and you can get back out there and get back on track. Like that's the manager's job, I feel. And if you can do that without a heavy hand and it's more of a, like, show the story. You know, like there's a sales story, there's a marketing search, share the story, see the picture, understand how the, the sales process works in the execution. These are all blocking and tackling, which again is what a good leader should do. Get back to the basics. So, you know, that was a lot for a little bit short question. But it's a, it can be complex, but it doesn't have to be. If you can be to your point, if you can be a compassionate leader and show empathy and, and be willing to be tough and candid, but be human, because we're belly to belly. It's a human connection. You know, nobody wins from this or berating. Nobody wins in any of that leadership styles anymore. And I like to look at more of as a collaboration, a team. We're a team. How can I help you get better? How can you help me be a better leader? Like, give me feedback.
Ryan
When you think about. You talked a little bit about these one on ones. And I used to have one on ones every single week. And right now it's like there's a big debate around one on ones. And you talked about it as a, as a coaching opportunity, as a mentoring opportunity. Right now in the Headlines are don't do one on one. So Nvidia's CEO just came out and said he doesn't do one on ones. He brings all 60 people together and he talks about what's going on and like, that's enough. The CEO recently of Airbnb came out and said, listen, I believe in having private conversations when I have teammates that are in need or they have personal issues that are going on. But I find that when I get involved in one on ones, I start to solve the very problems that they're supposed to be solving. Or there's this idea of there's politicking. So maybe there was a decision or something else that had happened and now they're trying to take a new position or outside of the main room trying to take or steer, steer the company in a different course. What, what type of frequency do you recommend from a one on one? And how do you, how do you navigate this, this whole, like, I don't know, I used to do them weekly and now people are saying don't ever do them. Like, what's your take on that?
Chris
Yeah, yeah. And you know, coming up like you did, man, I've seen the weeklies, quarterlies, I've seen all of it. For me, it's like, look, at the end of the quarter, we're going to review your performance so that you know, there's a quarterly review because we know each month exactly what you got to do and where you got to be. So we'll going to run the scorecard at the end of the quarter and then you're going to ask me questions and I'm going to ask you questions. That's coaching. My hope is if so if one of my direct reports has an issue, they damn well bring it to me. They don't wait, let it fester or get worse. It's like Johnny on the spot. Right? I'm totally open to that. But that's dangerous too, right? So the one minute manager meets the monkey. You know, if you. I had a client, their door CEO, open door policy, huge company out of target market from the smaller operating system. So big company, big, big franchise, actually. And she went to her peer group and she's like, I need help. And they're like, okay, identify your issue. I have eight executive direct reports and six of them just keep coming into my office unannounced asking for my help. And I'm sick of it. Every single person in that round table said to her, you're the problem. Not, not, not to executive. And she's like, her jaw dropped. She goes, what do you mean? I'm the problem, I'm the CEO. They're like, hold on. You're allowing the behavior to happen. Read this book, right? And the One Minute Manager is a small book, but the essence is if, if you open your door like that, there will be people who take advantage because what do they have? They have an issue carrying an issue. What do they want to do with that issue? They just want to dump it off on their boss's desk because I can't do it. And then they or I can't solve it. I need your help. And that either way, they're running out the door. And so that's all they're trying to do is dump their stuff. So the solution she did was she got memo to the executives, the whole team, not just the six. And she said, moving forward, you may only come into my office unannounced with an issue, as long as you have three solutions so that I can help you pick the best one. One, three, one. Brilliant. Brilliant. And guess what started to slow down.
Ryan
People come into the office.
Chris
Damn right. They'd stay to their desk and they'd figure it out. And instead of going upstream, where should you go if you have a departmental.
Ryan
Issue downstream, People closest to the problem.
Chris
Here you go. And so she was able to flip the script when instituted. 13 1. I teach that to all my clients now.
Ryan
Wow. 1 3, 1.
Chris
For every one issue you have, in order to see me, you must bring three solutions so that I can help you pick the best one.
Ryan
And that takes like, what's interesting about that, that type of, of tactic is the notion from, or the headlines right now is not to like completely eliminate one on ones. It's to not create frequency or dependency on one on ones. And it sounds like that's, that's what one three one does, is like. It still invites those conversations and it still helps create and cultivate those relationships. But at the end of the day, like, it's almost boundaries. It sets, it sets boundaries.
Chris
It's boundaries. And you can determine the strictness of those boundaries, right? Because the thing is, she was allowing the behavior to happen, right? But she was like, super frustrated. So, you know, one little different perspective and boom, she's like, ah, I get it now. And, and if we could teach that down the line, imagine how many issues could get solved locally with the people who live, eat and breathe that issue most of the day.
Ryan
I went through Naval War College about a year ago and I went through this program called sldc. Stockdale Leadership Development curriculum. Really, really interesting program. Discovered a lot about myself and everything else. And one of the. One of the instructors, Professors came to me, and he was like, you strike me as someone that people just use up your time. And I was like, oh, interesting, because I was just at drill weekend this past weekend, and I have an open door policy as well, and I got nothing done on that Saturday and Sunday. So I used to have to fly to Houston. I recently just changed commands, but I was in Houston. So I go from Newport, Rhode island, to Houston, do a drill weekend, then go back to Newport, Rhode island, to continue class. I had an open door policy, but I only have two days. So once a month, I've got two days to get done everything that we need to get done administratively, things like that. And I would have people coming in all day, and I would realize that I didn't get anything done that I needed to get done, specifically when I was down there because of the open door policy. And he didn't speak about the strategies as eloquently as you, but the whole idea there is like, you have to find a way to protect your time.
Chris
Yeah, you really do, because, you know, you have your work to work on. You know, we're. All of our collective work is moving the cheese, right? But if we have all of these, you know, departments, and if we consider them cylinders, they all got to be firing in synchronization, right? And we don't want anything to clog the line coming in. We just don't want to foul, you know, a piston or follow the whole engine. And there's got to be synchronicity, right? There's got to be timing, and so there's got to be cadence. I. You know, look, I think the more touches you have with your direct report, the better. Hence, a weekly departmental meeting, right? The one on one touches, you know, that's determined by the leader. Yes. We could. You know that four times a year, we're going to review your performance. Okay. Do I need to have a monthly conversation? Maybe. Unless they need it otherwise. Not. You know, the last thing I want to do is get in people's way. So, you know, I'm of the ilk. Like, you know, train them up so good, right? And then get out of their way. That's what great leaders do. That's everything I've ever read is train them so well and then get out of the way. Give them a chance. There has to be a leap off point, a jump off point that the trust and some leaders hold on tighter than others. But it's individual choice as a leader. But I think you'll find that the more touches you have, the more you keep your finger on the pulse without being this, you know what I mean, Overbearing. Just keep your finger on the pulse, you know, that's it. That's all you need. Light touch, not a heavy hand on the throttle.
Ryan
And that, that gets right back to your, your trust. But verify that you talked about kind of earlier in, in the conversation where it's like, you don't have to micromanage, you don't have to be all over top of it, but, but just verifying that things are happening. How do you like, when you look at it just seems like such the opposite approach. We share that philosophy almost to a degree of where my Vistage chair used to always pull me aside and he's like, hey, there's a difference between stepping back and abdication. You are completely removed. And I'm like, yeah, but I just need to get the hell out of their way so they can get their job done. He's like, yeah, but you still need to be there to support. You still need to be there to verify and make sure that we're upholding the standards that you've set and the expectations and things like that. And so like when you think about the Elon Musk's of the world and the, the Steve Jobs of the world, you hear the complete opposite where like their hands are so tightly wrapped around whatever it is that that organization's doing that like you wonder how anything gets done. And there's actually probably another more recent example of something similar. And like, what's your. You and I share that philosophy, but how are other people so successful by like putting the thumb on and like strangling, making sure that, that everything is being done exactly to their standard.
Chris
Yeah, it's quite a feat. It's pretty impressive. I, you know, look, it's surrounding yourself with brilliant people to run your company and clearly that's what he's done. And you know, he, he acquired some of them, most of them, I think. Right. But he's, he's gone out with a clear idea in mind, from what I can see. And he went out and just got all the right people to the best of his ability and these people and you know, look, he's a charismatic guy. I mean, love him or not, he's a charismatic guy, but you know, he is working on things for humanity. And I think the people, you know that probably there's a lot of People who, who are pulled to that. But you know, these companies are, they're all impressive.
Ryan
It's changing humanity. We have internal debates over intolerance. Intolerance and a lot of, a lot of other things down that, that path. And the reality is, is like you don't, you don't have to love or hate somebody for them to change the world in a positive way. And it's very hard to know like what's true and what's not true nowadays. And that's, that's half the, that's half the issue with all of this.
Chris
So, yeah, you know, I, I've been in this space well below 100 million most of my career. I've worked with a few clients fortunate enough to work for a few billion dollar clients, which is, that's a whole nother level. Same thing, but, but a whole other level. And in the entrepreneurial space, you know, I'm excited like right now I'm launching an initiative that's veteran focused. Veteran and first responder focused. We have about over 2 million registered business owners that are either a veteran or a first responder across the US and I've had so many DoD clients across the years. And this is part of my give back now. I really am focusing a lot of my efforts and this is, you know, this is getting down to the ground, right? Like veteran comes out, wants to start a business or maybe they started it while they were in or put it together and now they need, they're launching, you know, oh my God, they just served the. You served our country, now you're going to serve us again by building a beautiful business for, for our country. Like who can't get behind that? I'm in. So that's who I'm, I want to help. And we've got a lot of cool things happening with pulling the resources. Remember I said about filling the gap with the resources. So my current venture is called Profit first app dot com. So like digitizing the book Traction, the most popular book on cash flow management is called Profit first by Mike Michalowicz. And we've secured the licensing rights to the book and we've launched. And listen, when I first became an entrepreneur, I had this meeting with a huge company. They eventually bought us, but it was the first meeting and I'm green, man. I'm wet behind years, but I'm, I'm good at what I do. And I got this meeting and so there's like 12 executives in this conference room and the, the, the owner CEO, third gen was down at the other end of the table with a person sitting to their right, never introduced himself. And. And we're talking, and I'm doing my thing, and this guy, introduction. He goes, hey, Chris, can you share your last three years ebitda? And I said, well, I didn't come here today to share that sensitive information, but if today goes well, I just might. Like, I've been in a boardroom before. I know what. I don't panic. I don't break. I've already. I've already, like, earned my scar. So I know how to handle. Right. I left that meeting shaking in my boots. Wonder why I could. I couldn't repronounce the word. He said. I go. I'm like, what did you say? I go. So I called my accountant. I go, yeah, this CFO guy wants to know my last year's, like, last three years, EBITDA B or something. And she goes, chris, did he say ebitda? I go, that's it. I go, what the hell's ebitda? I don't. What's even. Well, here's the story. So I'm. I'm. You know what dyslexia is with letters? I have dyslexia with numbers. So if I look at a spreadsheet, forget it. I want to vomit. Don't do spreadsheets. So I steered away from financial classes. So I never learned anything, really. And my dad never taught me anything, you know, so my accountants. I said, listen, I want a crash course on, like, accounting, like, for a small business. And that's how I learned. I went to my CPA's office. She made a glossary of terms for me, EBITDA being one of them, and she just kind of took me through it all, and I had a. A sense of cash flow and all that, but she really brought it together for me. And so you know what I've been doing ever since that day that I didn't know what EBITDA was? I have all my clients, their scorecards. They have to have definitions behind the KPI, and it has to. What's the output? Because people like me who aren't good with math will be very reluctant to raise their hand, admit they don't know what it is. But you can't have that mindset being a leader. The minute you roll up into a manager and you have a budget and all that sort of stuff. So, you know, if you're that person, don't. Don't be afraid to ask one more question, or don't be afraid to put yourself out there. I know it can feel embarrassing and all that, but. But believe me, you'll never want to get caught like that again. And I never was. Right. And so my business, I needed to invest in that so that my financial business acumen went up. Right. And I could be prepared. But there's. There's a lot of stories like that.
Ryan
In the beginning, and is that so talking about the app, like, is that bringing that book to life? By the way, Profit First, Reddit, five, maybe five years ago, maybe six years ago, became one of my favorite books. And I run my entire life on Profit first. We're not doing too good running it with the business because we only have one bank account, and it just creates a headache. But personally, I've got like six bank accounts, and everything just goes to where it needs to go. And. And like, it's all hidden. And what's, you know, it's what you see is what you get, or what you see is what you spend, or whatever. Whatever it is. Love the book. So you're taking that book and creating some sort of app that helps people kind of focus and manage.
Chris
Yeah, this is another great story. It's just, you know, I've been at it for 30 years, and they start adding up. So I had a client way back in the day when I was an EOS implementer, I had a client on the Space coast, and they were custom engineering and they were doing great. They doubled in size while I was their coach, and they pretty much graduated just before COVID And I got a phone call one day from the founder, and he's like, chris, I gotta talk to you. I'm like, what's up? And he goes, listen, he goes, we haven't talked in a while, but after we graduated and Covid hit, we lost several DoD contracts, like government just, you know, that's. That's a whole nother story too. I've got a lot of DOD ones. Right. But so anyway, he. He said, it's. He said, I found myself for the first 13 years in business. First time, he goes, I'm upside down, like 350 grand. And he goes, I'm in my peer group. And he goes, chris, do you remember how we met? I go, of course I do. I go, your peer group gave you the copy attraction. And you open it and had my sticker on the inside. He goes, yeah. He goes, well, I was in my peer group. I was telling my peer group about my cash flow problems, and a guy handed me the book Profit First. And so me and Richard his partner. They felt after having. I'm not tooting my own horn here, but after having been coached by me, they felt they had the discipline and accountability to adhere to this Profit first methodology. So they did. And in 18 months they paid off all the debt. They were positive six months ahead, paid the debt off plus six months reserve in about that short time frame. And they said, it's the book, it's the methodology. It sounds crazy, you got to open up all these bank accounts. But it, it worked. And I'm like, great. And I'm like, you want to build a SaaS product, don't you? And they're like, yeah, we'd like to have you join us. And so we started a company and we started programming and then worked out a deal with the author and to get the exclusive license agreements. And so. And now we're ready to launch 2.0 and there's going to be that little hiccup you talked about in the banking accounts. Hopefully we've solved that. So when we launch we'll have to get you in there. Because everybody said, you know, the Profit first was kind of difficult. Like EOS was. It's just paper based. You, you print out all these papers, how do you keep track of them? It's just a bloody nightmare. I mean we've had software since the. I won't, I won't go down that road. But it was, it was weird not to have software for a whole system. But anyway, the, the, the guys were like, we want to build a SaaS product and we become coaches, profit first professionals. And so I said, I'm all in. And so here we are, we're ready to launch 2.0. We are tracking nicely and we have, I mean we, we are working with the Author weekly. It's wonderful the access he's giving us. And so you're just going to see this product continue. And we've got the base basics in the book, right? Just like EEOS and the five foundational tools. That's how 90 was launched. Just the five tools. But look at it now, right? All these years later, it'll be like that with Profit first, right? Right now we got the blocking and tackling of the book and getting people on board, right? Just the early adopters and we're very excited about the product because it fixes such a huge problem.
Ryan
Is there a consumer play? Because like, like the, I think obviously Profit first and the whole thing is about business, but there's also seems to like, it's changed just like EOS has Kind of changed the framework and like, put things into my adhd, the brain and compartmentalized and helped me out there. Like, Profit first has helped not make financial or like, take finance out of my brain. And it just works. It just automatically works. Is there a consumer play to this? In addition to the business, the B2B plays.
Chris
Yeah, listen, we, we want to take the Profit first app global to any entrepreneur who's struggling with profit. You know, entrepreneurs, they work, they grind, they grind, they get to the end of the year, where's all my profit? Where's my money? Is really what they're saying, right? And, and they're like, man, I work so hard. And they look back and it's just like, for what? For what? And so that's, that's, that's hard to continue under those circumstances. Right. So when we, when we talk to them, this is a methodology that is going to ensure, provided you follow the methodology, right, that at the end of the month, at the end of the quarter, at the end of the year, so much so that you even, you know, you'll be paying not only salaries, but you'll be paying, you know, the owners compensation in addition to their salary. Like it. But it's all right there in front of you. And the thing is, the funny thing is about all that, Ryan, is it's the envelope method. It's. My mom used to use it in our house. Cash would come in and my mom would pull out her folder, which had envelopes, clothes, food, electricity, more. I swear I can see it right now visualizing it as a kid. And so Dave Ramsey, big component of the envelope method. And the cool thing that Mike Michalowicz did is, you know, we were all taught sales minus expenses equals profit. My dad taught me and all my brothers, pay yourself first. You got to keep food on the table and a roof over your head. Right. All Mike did was sales minus profit equals expenses. Brilliant. But it's, it's not, it's not like it hasn't been around. My dad taught that to me and my seven brothers. Pay yourself first. Just establish your profit. Pay yourself first and pay everything else. So that's. It's a great, great book. Highly recommend it. And if you have time, you can check out the app@profit first app.com.
Ryan
Nice. I've got this weird thing where, where if I read something or like, like if something like really resonates, I need to find out who the author, who that person was. And so when I read that book five or six years ago, I hunted down Mike and just had a very brief. It was either email exchange or LinkedIn DM. But from our three sentences back and forth, seems like an amazing human being.
Chris
Yeah, you should see him on stage. He's, he's a very good speaker. Really connects with, with the entrepreneurial audience for sure.
Ryan
That's awesome. All right, last thing. Anything that usually we get to this point and I'm like, oh well if people want to find you, how do they find you or where do they find you? And, and you know, EOS implementers and other people that are seeking business give out their sometimes cell phone numbers. That's not, that's not really. I don't think you're, you're necessarily looking for clients. You're looking to spread the good word of all the things that you're doing and the ways that you're giving back. However, if there is anything that I haven't touched on or information that you want to put out there now is, is your time.
Chris
Yeah, you know I'm, I'm still coaching clients so we're. My primary focus right now is the Micro Business Academy IO and that's helping micro size businesses. That's where I've got a page dedicated to veterans and first responders. We're going to be growing that up more Q1, but I also do a lot of executive one on one coaching. I have a one year curriculum and then I support the guys over at Profit Pro where we're working on. I'm kind of the head of BD over there. So you the head of BD Looking, looking for, looking for that next development opportunity.
Ryan
There you go. Awesome. Well Chris, thank you so much for taking. Now it's been an hour and, and probably like 10 minutes but thank you so much for taking the time to come on and learned a ton. Full page of notes and can't wait to talk to you in the future.
Chris
Yeah, you bet you. Ryan, thanks. Always good to talk to you buddy. Take care.
Host: Ryan Hogan
Guest: Chris White (former EOS implementer, co-founder of 90, System and Soul, Micro Business Academy, Profit Pro)
Date: September 17, 2025
This episode explores the power of compassionate, empathetic leadership through the experiences of Chris White—a serial entrepreneur and executive coach known for co-founding several influential business operating systems, such as 90 and S2 (System and Soul). Chris shares his journey from SaaS entrepreneur to pioneering implementer and thought leader in business operations, emphasizing that true leadership means genuinely caring for people, fostering healthy conflict, and continually learning and growing. Central to the discussion: empathy is not a soft skill but "a leadership superpower" tailored to today's work environments.
[01:15]–[08:23]
"All I ever wanted to be was a teacher and a coach. This book changed my life because it allowed me to become a teacher and a coach...just at the executive level." —Chris [07:11]
[08:23]–[13:29]
“Great leaders get out of the way of people. They let them move.” —Chris [11:36]
[13:29]–[20:21]
“You just didn’t realize the impact you are having on others.” —Chris, recounting his coach’s advice [18:44]
"Even at the age of 60, I still have something to learn." —Chris [19:49]
[20:21]–[27:33]
[27:33]–[31:58]
"If you can be a compassionate leader and show empathy...and be willing to be tough and candid, but be human—nobody wins from this or berating. Nobody wins in any of that leadership styles anymore." —Chris [31:32]
[31:58]–[37:40]
"For every one issue you have, in order to see me, you must bring three solutions so that I can help you pick the best one." —Chris [36:26]
[37:40]–[40:50]
[40:50]–[43:27]
[43:27]–[49:02]
[49:02]–[57:45]
“Entrepreneurs...get to the end of the year, ‘where’s all my profit?’ Where’s my money?...It’s the envelope method...My mom used to use it in our house.” —Chris [55:04]
On leadership transformation:
"This book changed my life because it allowed me to become a teacher and a coach just at the executive level."
[07:11] —Chris White
On partnership selection:
“Surround yourself with smart people. That includes smarter than you.”
[10:51] —Chris White
On radical candor:
“You fundamentally have to care about your people and if you do, then you’re going to be willing to piss them off a little bit because you’re going to challenge them to be better, but in such a way that it’s appropriate.”
[24:45] —Chris White
On being a leader worth following:
"Even at the age of 60, I still have something to learn."
[19:49] —Chris White
Empathy in leadership:
"If you can be a compassionate leader and show empathy and...be human—nobody wins from this or berating. Nobody wins in any of that leadership styles anymore."
[31:32] —Chris White
On conflict and ego:
“Healthy conflict is like, ‘Hey, I’ve got to talk to you about a particular issue...it might sting a little, but I just want to get it out...’ unhealthy is when it gets personal.”
[14:41] —Chris White
Practical wisdom:
"Train them up so good, right? And then get out of their way. That's what great leaders do."
[39:23] —Chris White
Chris White’s career illustrates that enduring business transformation is always rooted in people—through partnerships, empathy, and a relentless commitment to self-improvement. He urges leaders to balance accountability and compassion, set clear boundaries, and never stop learning. His ventures continue to bridge gaps—from digitizing proven methodologies like EOS and Profit First, to empowering small business owners—including veterans and first responders—to succeed on their own terms. Perhaps most powerfully, Chris models the humility to learn from every mistake, making self-awareness and empathy not just leadership assets, but superpowers.