How to Avoid Leadership Failure While Scaling

Ryan Hanley on why ego kills scaling companies. He fired a vanity hire, learned to align values with work, and treats every initiative as an experiment. Hire for real constraints like parenting, build psychological safety so teams own their mistakes.
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You know, we can't solve problems that don't exist. Right. I find a lot of leaders spend a lot of time solving problems that simply are not real. You don't have to be the strongest, the smartest, the fastest, have the best ideas. You don't have to be the best at anything. To be the best leader never puts your ego in being right ahead of finding the solution. It is not about being right. It's about getting it right. That is the song.
Good.
That is so good.
Guys. I'm the one and only Ryan Hanley. Dude, what is going on, man? So good to see you again.
So good to see you, man. Your episode on my show was phenomenal. People still talk about it. People still share it. Dude, you are, you are a boss man. And it was just such a pleasure, Chad.
I appreciate that. Oh, man, I appreciate that. You know, it's, it's funny. When you work as hard as you do to build such an engaging audience that actually cares about leveling up in business life. Gosh. Themselves, you can't, you can't help but just show up, which is why I wanted to have you on this show. Because, you know, it's, it's, it's one thing to understand what it means to be at the top of an organization and go through different transitions. It's another thing to become your own CEO and founder. It's another thing to raise your own money. It's another, like, it's all these different layers. And I'm curious to know. I think where I want to start is because leadership is probably the most difficult thing that so many of us struggle with. Right. You know, as far as how to do it effectively, what has probably been the most transformational thing you've discovered along your journey that has allowed you to become the leader of the organizations that you are today?
For a long time, I believed that everyone operated.
From for the good of the organization first. And that's not to say that people operate against the organization. But I, I, I don't know how, if I was because of my Christian upbringing or I don't know what it was in my past. And frankly, I don't know. I wish I had, like, a good idea, and I've spent a lot of time thinking about it. But when I first got into business, you know, back in, my first, my first corporate job was in 2003, I worked for a company called RSM McGladry down in Washington, D.C. they were a top five accounting firm at the time. And I always just operated under this impression that when you. It was like being part of a team. I was always a sports guy, right. I played football, basketball and baseball. I played baseball in college, baseball a little after college. I always just had this mentality that you're on this team, you're part of this company, everyone's pushing in the same direction, everyone's doing things for the betterment of the company. And, and I found that I was really bad at internal corporate politics. And it wasn't until I started to understand that people operate for their own good first or need. Their, their needs inside the organization need to be taken care of first. Then they can focus on the needs of the organization and when in that reframe of okay, create an environment, create a culture, create boundaries, create expectations, goals, etc. That align first to the needs of the individual that then allow them to excel inside the organization. That's when my leadership career took off. And that's when I was able to build cultures very rapidly and scale the businesses that I've been able to do. But man, I'll tell you, I was coming into the corporate world. I was so far off on that. Um, and I paid the price a couple times, which we can get into. But, but yeah, that was a huge culture. That was a huge shift for me as a leader.
Yeah, you know, it's really interesting is I've discovered that we learn more about leadership from when we don't get it right than when we do more than anything else. And I think that's one of the reasons I actually, because I, as the reason I'm gonna bring this up because I think it's, I think it's profound. I, I thought, and for the audience, if you guys don't know, Ryan Hanley has, as a multiple time TEDx speaker, he's done a lot of really amazing things. Very successful entrepreneur, has one of the pop rated podcast of all pod which I invite you guys to go check out as well. But one of the things that I heard you talk about that I've never heard anybody else talk about is the importance to dying to status. Because I feel like we are all like all young, old entrepreneurial leadership, operational leadership, whatever. I think there's an element of us that is, that feels like we have to pursue the status. So first of all I'd like to learn how you discovered this lesson, this painful lesson and then how it shifted you and changed you and how the audience could now benefit, you know, from understanding how status is not the way.
So my, so my last TEDx that I did, which you can if you search. It's called stop living a life you didn't choose was on this topic. And you know, this has been, this has been. This was a tough lesson for me to learn. So I grew up in a very poor town in the middle of the sticks of upstate New York. There were 900 people in our town. And we used to say you leave the doors open at night because the criminals lived in our town. They didn't rob three from our town. And it just was, you know, and there's good people that live there too. But at 12 years old, I remember looking around my town going, I need to get the out of here. Like, I can't. This can't be my life. Like, I need to get out of this place. There just was no opportunity. It was a very depressed area and a lot of people just scraping by. Every male role model in my life was either a drug addict or a criminal or an alcoholic. It was not a very positive environment. But through blessings of God and the love of my mother and my father, I was able to see the world, that there was a bigger and better world out there that had potential. Okay, so, so for most of my life, I, I couldn't lean on status. I had to just be the best to get out of there. Because when you come from an environment like that, whether it's an urban inner city environment or a depressed rural environment, you don't ever get the benefit of the doubt. And I get it. Like Today I'm a 6 foot 3 white guy, I'm in shape, I'm successful, and you're going, woe is you. Well, back then I was, I was, you know, my, my nickname in middle school was fat Boy. They used to call me my town name because it was such a shitty town that just calling me the name of the town was a derogatory name.
Called Jesus of Nazareth.
Yes, right, exactly. So, like, it was so, like I, I had to fight and scrape so I couldn't rely on status. Okay? So that was how most of my life was built. And then I started to get some success in the business world and it was like, oh, I did this thing and I built this and I sold this and I gave this keynote in front of, you know, 5,000 insurance professionals. And it went over really well. And oh my gosh, and now all of a sudden, I'm starting to feel the. What comes from the status, right? People wanted to interview me for their podcast. They wanted me to come speak at their event, they wanted me to coach it. And I'M Dude, I'm. I'm falling for the trap, right?
Yeah, I did. I did say that's why.
That's why I hadn't talked about this.
So I fell for the same trap. Yeah.
Then. So then I have this job where. And we can tell this story, too. But I had a job that I loved. And unfortunately, it's an interesting story. We can come back to it. But I essentially get fired. Okay. And I took. And now I'm looking for my next opportunity. And there's a whole bunch of opportunities blessed that there was. I took the opportunity that was the worst fit, the worst fit, but came with the most status. So I'm making more money than I've ever made. It's the hottest company in our industry. My industry that I've worked in most of my career is the insurance industry. They've raised a ton of money. They're all over the place. And I'm. Now I'm the chief marketing officer. I'm third in line to the CEO, right? Like, this is a job. Like, this is the job I'm supposed to have. And I'm just, I'm walking around like I'm the big swinging, you know, whatever. And, and, and, you know, I'm just all the ego. I'm just all the ego. Right?
Yeah.
And, and okay, so six months into the job.
Six months into the job, I'm sitting in a meeting with the CEO and the, the, the chief legal counsel, and we're having a performance review. Right. And we're talking about some stuff and whatever. And I had some ideas on things that I, as the chief marketing officer, that I thought we should be doing.
Yeah.
And essentially the CEO turns and looks at me and goes.
Don'T you realize by now that you are a vanity hire? Like, like, he just didn't give a shit.
Vanity hair.
He called me a vanity hire. So basically what he wanted because of all the status that I had built in my previous position and all the, like, attention and all that I, that my name came with again, in our small piece of the world in the insurance industry, that's what he wanted on his team. He didn't give. He didn't care about the strategy. He didn't care that I thought we, you know, this messaging was miss. He didn't want to hear any of it. He literally told me, like, go find something to do. We. We don't care what, what you think. And, dude, it hit me like, a ton. It was like, it was like the ego balloon just got popped. I mean, imagine if you think you know what you're doing, you're on top of your game. You're excited, you're energized, you're engaged. And someone goes, you, Nothing you say matters.
Wow.
We're paying you simply so we look better as a company. You know, we just bought this guy who's got a name in a space, blah, blah, blah. So our valuation looks better and our team looks better in an investment deck, but we don't actually give a shit what you say. Now, some people might go for the money I was making. They might go. That's a first world problem. You're an idiot. For me, and, like, at my core, again, you know, I don't know if it's against being raised Christian or the fact that I grew up with loving parents. Like, I. Dude, all I want to do is help people. Like, at my core, I given up so much money because I just want to help people. I just want people to get better. That's it, right? So, like, all of a sudden, I was like, it, it just completely deflated. I went into, I went into a tail spin. I was depressed.
I ultimately, like, had to leave the job. There was some extenuating circumstances with travel and a sick family member, but it just was like, I just found myself in this place of, like, complete, like, like, what's your worth? Like, literally this guy was willing to hire you for just for your name, not, not for who you are, not for what you could bring, what you thought, what your expertise. None of that. Didn't care about any of that. And, and man, it, like, it was, it was like a, it was like a Mike Tyson right hook. Right? Like, everyone's got a plan. That was my getting punched in the face moment. Even getting fired from the job that I loved before that didn't hit me as hard as that moment. And possibly it's because it was kind of stacked on top of each other, but. And I tell this story in the TEDx talk. Sometimes, like, our biggest breakdowns lead to our biggest breakthroughs, right?
Yeah. Yeah.
So I, I, I leave that meeting and I walk to my office. I'm on the 15th floor, corner office, windows again. Like, they set me up to basically just sit in this room and do nothing, and I'm staring out the window and questioning life choices and what do I want to do? And oh, my gosh, like, you know, I'm an idiot for coming here and, you know, the whole shame spiral and all this kind of stuff.
And it's funny how, how the muse works, right? I believe in the muse. I act as if the muse exists. And for those that don't know, the muse is the opposite of the resistance. Steven Pressfield talks about this in the War of Art and some of his other works. But the muse is inspiration, serendipity, right? It's creativity. And, and I'm sitting there and I'm just kind of marinating in all this and, and this idea pops in my head. When I was 10 years old, my first entrepreneurial endeavor, I guess you could say, you know, again, we're very poor. I have zero money all the time. Yeah, we used to get, I used to get one new shirt, one new pair of jeans, one new pair of sneakers every year. That was it. And I just had to ride those three things out with whatever else I had. That was it. That was all we got. Right? Yeah. So, so, so I wanted more. I didn't want to be the kid who had to wear the same shirt three times a week because the rest of his shirts didn't fit. Because you had grown from year to year.
So what I would do is I would wake up at 4:30 in the morning and I would leave my house. Bless you. And I would walk out into our, our community. And now this is back in the early 90s.
People used to put their recyclables in these little blue bins in front of their house. So I would take two 50 gallon garbage bags and I would go walk the streets on Thursday mornings before school at 4:30 in the morning and collect all the 5 cent deposit bottles and put them in bags and walk around my neighborhood. And by the end of like an hour or so hour.
The winter.
In the middle of winter? Yeah, in the middle of winter, you know, because I'm living upstate New York, so it's freezing cold, I'm in a parka, you know, and I would walk around and collect. I'd be carrying these bags and I'd make 30, 40 bucks a week off of that. And Now I got 30, 40 bucks in cash in my pocket every week as like a 10 year old. I'm riding dirty like I'm the pimp at this point, right? Like now here's the funny part guys. And this is where status, this is where the status part comes in.
My friends used to call me garbage boy. They used to call me garbage picker. They used to just absolutely harass the out of me. And I'm going, guys, I'm making 40. You. But you pick garbage. We'd never pick garbage. You know, you're Dirt, I mean, just tear me apart. Yeah, because I was willing to do this and, and you know, in my neighbors, I had neighbors that would open their door in the morning and yell at me, tell them that I'm not even on their property. I'm walking on the street, they're yelling, get out of my garbage. All this stuff. And I didn't care. Like literally at 10 years old, I didn't care. It was about the goal. I needed money and I was willing to do whatever was necessary, right. Legally, obviously, to get to that goal. And it was this that hit my brain when I was sitting and I'm like, oh my God. The 10 year old version of me had more discipline, more self respect, more humility, more control of his ego than the, you know, 30 something version of me, you know, however old I was at the time, you know, did. And I've never let that mistake happen again, dude. It was like I have never ever from that day forward allowed the, my status impact to be a deciding factor. And what I did, if what I thought I was doing was right. And it's defined my life. And while, you know, I've obviously more ups and downs and entrepreneurial stuff and tons of wins and losses, like anybody today, I can say that I feel like I operate from the healthiest place of ego that I ever have. And it allows me to execute in every capacity of my life, whether it's relationship with my kids. Um, I'm single, but I have had partners in the, you know, and those partners. Yeah, uh, you know, like just every relationship, everything I do because, because I was blessed with that horrible moment.
I. Now, I, now I'm just, I'm just a better leader because now it's, what's the right thing to do, regardless of how I look, how we look, whatever, what these people are going to think, you know, oh, you had to backtrack here, you know, you know, you know, because I'm not standing next to Ferraris in my Instagram post like, I don't own a Ferrari guy.
I, yeah, I, it's, it's, it's funny, I heard someone say recently, what's the point of buying an asset that doesn't appreciate? You know what I'm saying? So it's like, I'm all about it.
Like, here's, here's the thing, man. Like, if you love cars and you're into it, go get a Ferrari.
I'm there with you. Except for the fact. And this is where we, this is, we can have a little playful banter. I Think you buy the assets that can pay for the Ferrari?
Yes.
So basically it's a, it's a, it's like a, it's a, it's a passive income kind of no brainer kind of.
Yeah, yeah. If you're, if you're buying a Ferrari on credit, that's the problem.
Yeah.
Renting the Ferrari to take Instagram bangers, which is, you know, which is unfortunately where our culture is gone. Right. So like I drive a chevy Tahoe from 2019. I can afford a nicer newer car, but I have two kids that play three sports. So I have a Tahoe because my car at any given time has five different bags of sports gear in it and I coach half those teams and that's the life that I want to live. And, and the entrepreneurial journey affords me to live in a, in a, a completely remade, beautiful 1300 square foot ranch that is perfect for a single guy who wants to not be bogged down with home assets or car assets with, wants to be able to take his kids on trips, pay for camps and clubs and you know, when I want to go on a trip, I can go on a trip at any time. Right?
Yeah.
I'm not bogged down by material goods. Right. So if someone were to say, oh, look at his 1300 square foot ranch, he, you know, he must not be a successful entrepreneur. Sure, you could think that. You'd be wrong, but you could think that. But what you don't know is on a drop of a dime, the way I've set my life up on a drop of a dime, I could take a long weekend wherever I wanted to go and not think twice about it.
Yeah.
And I would rather that to me, for me, is what's important in my entrepreneurial journey and what I'm building towards so that I can share experiences with people that I love and care about versus the things. And unfortunately, unfortunately for a lot of, especially the younger generation, we, our status is so determined by the things we can take pictures of. And that's the problem.
No, a thousand percent agree with you. In fact, one of the things that there's so much there to unpack. Well, first of all, I'm start with a former employer as a telltale sign of how not to lead.
And the reason I say that is because you and I have talked about this before. But all team members want to feel seen, valued, heard and appreciated in general. And I would dare say that whatever success that company was already at with the limitations of that particular leader would create the bottleneck within the organization. The organization can only get past this bottleneck, right? So. So the learning curve for everybody watching and listening right now on an example of how not to lead. First of all, it's a really poor example to hire anyone for status. I hire for expertise and talent. So I. Can you, can you help us move this ball forward? Because this ball's heavy, right?
Yeah.
The other thing that I, that I want to acknowledge for the audience and everyone watching, listening is the importance of being authentically congruent. Right? When you're chasing worth and you're chasing status and you're chasing these other things, inevitably what happens is you end up doing the opposite of worth to begin with. You end up self abandoning, right? So you were self abandoning. I self abandoned, you know, trying to buy the thing, trying to do the thing, trying to be the person, trying to be the thing. And which is what people, which, which I, which I heard you articulate so well is like you end up. You're just chasing constantly. And if you're chasing constantly, you're not effectively leading. Well, it's impossible to lead well if you're leading from insecurity, period. Right. Which is the, by definition, the chasing and stuff. Which is one of the reasons I wanted to, I wanted to pick your brain there because I don't know, I can't. I honestly can't think of all the folks that I know in the, in. In the professional, professional development industry, entrepreneurship industry, I don't know that I've heard anyone discuss not chasing status, not like being authentic and congruent with yourself. And I'm curious to know because I feel like being congruent with self is like one of the cornerstones of being successful, you know, so you will say, well, how you know, what's your definition of being successful? To me, it's like being congruent, like being complete alignment with how I was made and the way in which I.
That's the word. You just use the word that. So I've been working on this a little bit and kind of playing with these ideas and you just use the word that I think is. Is. Is not talked about enough. Is alignment, right? Aligning your values, the life that you want with what you do on a day to day basis, right? These things need to be alignment and then there's layers to that, right? If you have a partner, a spouse, right. You need to align with what he or she wants, right? Who are like, where are you trying to go and what are you trying to do? And I'll tell you where this idea came from for me. So my kids go to Catholic school. I'm a bad Catholic. I've never enjoyed the pomp and circumstance.
I'm a bad thing. I'm a good Jesus follower.
But I feel like, I feel like Jesus understand we have a relationship, we talk every day. I feel like I'm good there. I struggle with the Catholic church, but that's where my kids go to school. So there. So one day my nine year old, we're in the car, we're headed to baseball or whatever. I don't even know where we're going. My nine year old asked me, dad, is hell really like a fiery place in the ground and in, you know. And I know what he's asking, right? Like he's trying to, he's trying to get straight in his head the concept of hell with the reality of hell. And I said, I go, honestly, I don't think so. I don't know, I haven't been there yet. Hopefully don't go. Hopefully never find out.
Sure hope.
Hopefully they go, yeah, hopefully not. However, I said, I don't know for sure. However, I don't believe. So I said, bud, how I think about hell.
I the again I, I kind of follow Jordan. Jordan Peterson. I learned this idea from Jordan Peterson. Act as if, right? So Jordan Peterson used to say, now he's a believer, but he used to say when asked this question, I act as if God exists because I have not found a better manual for living a healthy, successful, love filled life. Okay? So I, I act as if on a day to day basis.
When I die, I'm gonna have to stand in front of St. Peter and answer for the life that I lived. That's how I act every day. Whether St. Peter is standing there or not, who the hell knows, right? But for me as a mental model, it works incredibly well to stay aligned to my values. To know I'm gonna have to answer for the things that I do. Right. Fifteen years of marriage, never cheated on my wife. I don't. Shit happens. That's not a judgment to anyone who's listening, who has that infidelity. I get it. But for me it's how. It's not like I haven't been presented with opportunities. It's not like my body didn't want to at certain times, but. Right. I always had this little voice in the back of my head, okay? So what I said to him is, dude, to me how I view hell. Hell is the feeling from the distance between when Saint Peter shows you who you could have been and who you are. So when you stand in front of St. Peter, he's going to say, look at this guy right here. This is who you could have been if you walked the path, if you did the work, if you were fully committed, blah, blah, blah. This is who you could have been right here. This person. And you're you. And I feel like the distance between those two things. The. How proud you are of that distance is. Is the difference between being in heaven and hell. If you stare at that guy and you go, you know what? I'm pretty close. Yeah, I did my thing. I worked. I made my mistakes, but I worked to be that person. And, man, I'm standing here for you today, and I'm. I'm pretty close to who that guy. Who that guy is. Yeah, walk in it. You walk in and you feel great. I'm sorry, I didn't mean.
You feel great.
Our audience, by the way, are real humans.
Okay. All right, good. Yes.
On Sundays. And let F bomb slip every now and again. Like, let's just keep it real on. I'm trying to get out of that whole world of like, we must be perfect on air at all times. I called alignment and congruence. Right. It's like, yeah, I. I love me some Jesus, but I, I every now and again say a boo boo word.
As me a person. I unfortunately curse a lot. I'm fast talking New Yorker. I can't help myself, but. But I try to keep it. Carriage. Keep it.
You know what's really funny is I think. I think curse words are in the New York Bible, actually.
Yeah, yeah. You just. You can't. You can't help yourself. It's just, it's. It's not even like it's funny. And I know we're contextual here for a second, but for those of you who don't live on the east coast or, you know, kind of like that New York, New Jersey, kind of southern Connecticut area, like, like, you.
We don't even see them as curse words.
It's just nuts. You guys created the F bomb.
It's just kind of how you talk to each other. You're just like. It's just like a way of expressing a certain emotion or feeling in the moment, whatever. Okay, so. But this idea of like hell being. You're created with this max capacity, whatever that is. Right? And maybe all of our are different. All of us, whatever. And. And hell is when you stand in front of that person you could have been, and you're disappointed in yourself.
Yeah. Wow.
That's hell. So, so, so the goal is not perfection. It's incremental improvement to the best version of you understanding and giving yourself. And this is why the Bible teaches things like grace and love and acceptance and peace. Because you're going to mess up. Yeah, going to mess up. And. But you keep getting back up, right? We all the lessons are about you're going to fall, get back up, you're going to fall, get back. That's the lessons over and over, the Bible and whether you believe in God or not, Jordan Peterson is right. It is the greatest manual to live a successful life. So, so kind of, you know, I'm a little off course on how we got here, but that, that definition and that kind of mental model keeps me today as aligned as I can possibly be to my value structure.
Well, and I think so to unpack some of that, I think that's the important piece is the focus of congruence, the practicality of alignment and the truth of living. Well. Right. You can't. I've said this before on a different couple places. I think you and I have even talked about it before. But I don't know, it's like 2019, hair, Time magazine and Harris did a Harris poll and they surveyed, I don't know, 400,000Americans across the United States. And essentially the question centered around how, how well do you think you're living right to, you know, do you. And simply, you know, the symptoms around anxiety and depression and overwhelm and all these different things. And they discovered that 70, I want to say it was either 77 or 78% of all of America that they surveyed. Now, granted, 400,000 is a small sample size for billions of people. But at the same time, I think it still proves the point that over 78, 77, 78% of them would say that they were living an inauthentic life. In other words, that they would say that they were living someone else's life. In other words, like you had talked about earlier, hey, look, I think I have to be this person with this mask to be accepted and to be validated by my peers. And it's funny because you both, you and I, with different stories, different experiences, got to the same place. It's like, no, actually you end up chasing and chasing and chasing and chasing and chasing and chasing and chasing and chasing and chasing until you stop this behavior. And then all of a sudden, you actually find your authentic self and your authentic tribe.
Right?
And I think that's so interesting to me because I feel like the world as a whole is sick of guru behavior and more into guided behavior. And the only reason, the only way you become a guide in anything is by living out the experiences and everything that comes with it. Which is one of the reasons why I think you and I hit it off from day one. Like, we both believe in transparency. Like, I'm. I'm told by my team all the time, dude, you're actually overly transparent. I'm like, yeah, but at least you know where I stand.
Yeah.
You know what I'm saying? So. Which I think is a. I think is a grossly underrated and underutilized skill as a leader.
Yeah.
I feel like. I feel like there's a false perception of leadership where you have to wear the mask. And I think part of me wants to keep going down this rabbit hole because I'm like, if I can help one leader, you help one Leader. We help 10 leaders, 100. Like, when we go and help these leaders understand that they're pursuing the wrong thing, they can then go lean their ladder against the right wall and really start building something amazing and actually make the impact and the income and all the things that they want collectively.
Yeah, dude. So, okay. So. So I love. I love this tact here.
One of the things when I'm working with a founder or a leader in whatever capacity and, you know, we're getting to know each other, one of the first things that often comes up, and I'd be interested if you find this similar. I'm sure you do. Most people who are new to leadership or are struggling with leadership, a big part of that is they feel like they need to have all the answers, that their team expects them to be strong and perfect and wealthy and good at everything and fit and all these things. And. And every answer they have, and that is 100% not the truth. True.
You don't have to be the strongest, the smartest, the fastest, have the best ideas. You don't have to be the best at anything to be the best leader you have. In fact, you don't want to be the best at anything in your company except for being a leader. Right. Ultimately, if you're hiring for the right reasons, as you said, expertise, talent, knowledge, energy, passion, commitment. Right. If you're hiring for those things, you don't want to be the best at any of the other stuff. You want to bring people in who are better than you. Those people want to follow somebody that they know is going to lead them into hell and back out with a squirt. What they want to Know with a squirt gun. Yeah.
You've heard that phrase?
Yeah.
Inner go it go after hell. Like you'll have to pin it out with a squirt gun.
Yeah. That's what they want to know, right?
Yeah.
I want to know that if I commit to you, you're going to be here when shit gets hard. You're not going to blame me, you're not going to fall off the table, you're not going to go on a three day bender and we can't get a hold of you, you're not going to check out, you're not going to start Cyprus. I want to know you're going to be here when shit gets hectic. And if I believe that single thing right, I will follow you all the way down.
Yeah.
And, and because the best leaders that mime, the mentors that I learned from, that I've molded myself on, like, I'll flat out tell people I don't have the answer. I'll be in a meeting. I'll be like, guys, we need to solve X problem. And you know, you'll watch all the eyes in the zoom call because most of the companies that I've worked for the last 15 years have been remote. Like they all kind of, they're waiting for you to tell them what to do. You're like, and I'll just look at them. And I, I've literally on calls before, just sat here in silence for minutes and then finally someone will like start talking or ask.
I'm like, guys, well what if we did this?
Yeah, okay, let's go down that rabbit hole. Let's, let's talk about. Yeah, I'm like, I don't know, like I, I don't know the answer. Guys. I know we all, we all agree, we've all kind of pounded the table. We've all harumped that this is a problem we need to solve. I concur. The group concur. Let's go attack this mountain. Yeah, I have some ideas, but I don't know the answer. So, so let's talk about how we get there. And, and what you in this is this, marrying this. So, so there's a, there's a secondary problem that comes out of this. Okay. So let's say people buy into everyone listening buys into, okay, I don't have to have all the answers. Great. My job is to help the team get to the answer or an answer that we can then put into market and try. Okay.
Yeah, yeah. Facilitate the conduit of ideas.
The second part Is.
Think of everything as an experiment. Everything. Because when we. You commit to a solution, if you then put all your. If you, if you go down that solution as if it's the only solution, that solution has to be correct. Now. Now status and ego start to pop up. Because what if it doesn't work, Stephen? What if it, what if I agree and we go down this path and it doesn't work? Oh, now I look like I don't know what I'm doing or the company doesn't look like it knows it, or, or we.
It's really funny about what you just said that you just actually gave a telltale indicator. I want to bring a highlight to this real fast.
Yeah.
What though, how would I feel if the what if happened? Because I feel like. I feel like. How would I feel if the what if happened already tells. You're either operate. You're getting ready to operate from insecurity or ego or arrogance. I think that's. I, I had to spotlight that just for a second because that's like, that's the fact that you even would say that even verbally or even thought to yourself is like, oh, that's a. I'm stepping in the ego.
Yeah, that's that. Because that's what happens, right? We're like, we start, we get, we get paralysis or we get over controlling. Because what if I, what if Sally has a great idea and I agree with Sally and the idea doesn't work right now I look like an idiot for listening to Sally and why do you prioritize her and she doesn't. And it's like, no, no, no, no, that's not it. I tell everybody in my company everything we do is an experiment until it works. Once it works, it's something we do. But it's just an experiment because I don't have clue what works and what doesn't. None of you know. None of us know what works. All these gurus out there talking about this or that and do this and this seven. None of them know if that shit's going to work for your business. You don't know what's going to work for your business. You could have the best. Elon Musk didn't know how to get to Mars. He had to wreck, what is it, 20 rockets, 40 rockets, probably more than.
That, trying to get the Joker to land on a base 100.
Like he didn't know how to do it. He knew, I want to get from this planet to that planet. How do we do it? Okay, we got these boosters okay, those boosters don't work. Okay, we need. We need boosters we can use again. Okay, so now we need to land them. How the hell do we do that? Let's try this. That didn't work. That's okay. Now we should probably land them on water because of this or that. Okay. Right. Like, yeah, everything. Like, you know, take your feelings of him as a person out and look at him and how he runs his businesses. Everything that dude does is an experiment until he figures out what works, and then he runs another experiment, and then he figures out what works, and he runs another experiment. And what that does is it never puts your ego in being right ahead of finding the solution. It is not about being right. It's about getting it right. That is so good.
Oh, that is so good, man. That was so good.
Not about being right. It's about getting it right. I love. Yeah, that's. It's. It's so true. Because again, your. Your entire organization will stall when you can't get past that moment. Whether it's. Whether it's a C suite professional that's on your team, whether it's you, it's on your team, whether it's somebody who's in administration where this is the way it's always been, it's the way it's always going to be. Like, I love the experiment. And it also reminds me of. Was it Thomas? I think it's Thomas Edison created 9,999 ways to make a light bulb until he found the one.
Right.
That's another, I think, another way to articulate very. Something very similar. But you're right. You're right. I think, and I think that's why you excel as a founder and CEO yourself, is because you do see logistically how everybody plays a role, plays a part, unlike where the show started with somebody not seeing how each individual plays a role or an active part, you.
Know, and what you get out of it, dude. So when. If you can cultivate this culture of it's not about being right, it's about getting it right. Right. Infighting go down, you see, territorialism go down, backstabbing sarcasm, it all goes away because the. You start to cultivate a group of people, and because the people, one who operate purely out of ego and status, they immediately stand out. And you can cut them out of the herd, right? You can try to coach them, and if they won't be coached up, you can cut them out of the herd. So what you're cultivating is a group of people who, at Any given time are willing to share an idea, a challenge, a frustration, an obstacle, an issue. Right, right. Like they'll come to you. And I, I, I'll give you guys an example. So.
After the job that I described before, where I was the vanity hire, okay. I ended up leaving that job. I had a family member get terminally ill and I couldn't travel anymore for work. So I had to take something local to my market. My market, Albany. The greater Albany, Saratoga area is not a bastion of insurance, you know, careers. So, so I, I had to kind of pivot for a second. I took a brief one year.
Hiatus from the insurance industry and I became the CEO of a stalled fitness franchise. They had eight locations, they've been in business for seven years and they installed at 2,000 clients. They couldn't grow. And the guy basically came to me. Long story short, he said, I'm a gym guy, I don't know how to take the business to the next level. He hired me. Awesome. 12 month contract, mercenary role. Perfect. Love it. Turnaround job, perfectly fit for what I wanted to do. Nine months in, I'm sitting, I'm sitting in the boardroom because every Monday morning at 8:30 I met with the founder and we just talked about what was going on that week. Right. Make sure we're in alignment and all this stuff. I'm sitting there and the best part about running a fitness business is I'm in Lululemon shorts. Lululemon. I got my sneakers on. Like, this is a CEO. This is what I wear at work every day. It was great. Part of my job was working out at different locations with our clients, like just shaking hands and it was awesome.
Yeah.
And I'm sitting there, you know, whatever standard Monday.
I see him pull in, get out of his car, and someone else gets out of the car, he's in a suit and his lawyer's with him. And I'm like, well, I'm hoping they're coming from another meeting. They walk in, sit down, CEO looks at me and says, you've done a tremendous job. You've done more than we expected. Unfortunately, your time here is done. Pushed the termination paper across, fired me on the spot. Thankfully I had severance, whatever, it doesn't matter. But, but come to find out six months later.
I had made the business so profitable in nine months that he didn't want to finish the contract. He wanted to take back over. Right. So that's great. Not awesome for me.
Another leadership principle here.
Okay. So I'm like, I'm like, you know, These experiences are stacking up and I'm going, something's wrong. I got to start my own business. Okay. So I start my own national digital commercial insurance agency. March 9th of 2027 days before the zombie apocalypse hits New York and the entire state is shut down. And now all businesses are shut down. So any clients I would have the chance of writing are done. I've already sucked, sorry, sunk like close to fifty grand into this business to get it off the ground. Because as much as you would think an insurance agency wouldn't be expensive to start, it is. And, or at least that expensive. And I'm like, I'm dying on the vine, right? I now can't, I have no money coming in, so I can't afford any help. And, and I'm just, I'm, I'm, I'm, I'm like this, I'm screwed. This is just a complete debt on arrival business. And you know, all the things. But having learned the lessons that I learned in the past. Right. And, and, and having developed this idea, everything is an experiment. Everything. Okay, well, so me going out and being this type of business isn't going to work. But I could hard pivot to digital, go downstream to like micro businesses and small commercial, which tend to be willing, more willing to buy online because there were still businesses operating. Yeah, this is, this is a play, right? So I pivot into this space and all of a sudden business starts to take off and we're doing well. Now I need to hire people. Well, here's the issue.
Insurance. It's, it's very expensive to hire good licensed insurance people. It is not a. Like, if any of you are looking for another career, insurance is the best business model that exists. It's not sexy. Don't get me wrong, there's nothing sexy about what I do. But it's a great business model.
But, and I didn't have the money to pay for these people. So what I did was I looked at the market and I said, okay, where can I get top quality talent? Well, there are most single moms and moms with young kids get run out of the insurance business because it's a 9 to 5 business. They want you to log in and log out. And you know, moms are young kids and I know, I'm not trying to be sexist, but you know, we still live in an age where moms tend to take care of the younger kids more than dads. Whatever.
Well, the reality is their moms are more, Moms are more equipped.
Yes, yes.
Scientifically proven More equipped children.
Yeah, from an empathetic standpoint, they probably should be, but you know, whatever, but. So there's all this incredible talent sitting out there that's been kicked out. So what I did, what I did was I started hiring these women. Talented, hardworking, and they would exchange less, less income, which I could afford in exchange for.
Availability or versatility in their schedule. So I made a hard rule. I do not care when you log in. I don't care if your kid gets sick and you got to leave for an hour. I don't care if there's a doctor's appointment in the afternoon. I don't care. You have X amount of work to get done during the day. Right, That I need you to get done. Which means you may have to log in at 6 or 7 at night or log in early just depending on what your day is. But you get it done. I don't care, dude. Loyalty, commitment, passion. I, I had an army of people and I love these women to death. I found them, you know, after I sold the business because it grew so fast. I was able to sell the business two years later and then when I exited two years after that, but found them all new jobs that wanted new jobs. And I still communicate just amazingly, but it was, the idea was ego wise, right? I should have got, gone out and gotten some high powered producer who has a big book of business that could, you know, bang, bang, bang. And I. And instead what I did was I brought in these women. Most of them hadn't even had never sold before. They'd ever, only ever done service work. And they were so excited and, and you know, people looked at my agency and they're like, you know, how do you know they're working? Are you keystroking them? Like, no, I don't do any of that. I don't do any keystroke ing. I don't check in on what they're doing. I'm like, I need to know. You need to be able to respond within an hour. So you all have cell phones. So you just, you know, if you're not in the office, I just need you to be able to respond within an hour. And I need you to get X amount of work done. And we created a simple plan with boundaries. And our agency didn't look like anyone else's. People would mock us for the way that we did business. They would mock us for. Because I. Our value proposition.
All the way back to the recycle bin, baby.
Oh, that recycle bin. But show me another freaking digital Agency which is grown. Which has grown from 50,000 bootstrapped to a seven plus figure exit in less than two years.
Yeah, well, so here's the point, though. This. Here's what I want to. One of the things I want the audience to take away from this is creativity and innovation always precede success and expectation, right? So if we can get to a place where. And you did this with your organization, right? Where people feel seen, value, heard and appreciated, you help them. You help these new team members feel seen, value, heard and appreciated. You understood the circumstances. You work on the schedules. You gave them definitive, definitive boundaries. And you said, this is where we're going. Let's. You want to come with me?
Yep.
Right. And they did. And they. And they signed up for it because you were in alignment. It was in. It was in alignment with who they are, what they wanted, where they were headed. What I think a lot of founders get wrong is. And this is my own personal opinion, is to your point, they go and try to model or mimic what everybody else has done before, thinking that, well, I can go scratch out 12 or 12 or 13% net income myself. I'm like, well, if we do it Ryan's way, we can scratch out 30, 40% of that. Like, you know what I'm saying? Just because. Because we. Because there's innovation. Because it's like, how do you go to the marketplace and solve the problem in the marketplace, but how do you bring the team and help them solve their problems along the way as well? I just thought that was genius, man.
Yeah, dude. So I. I got. I used to get in trouble because I used to talk about. So I love talking about best practices. I love best practices, but not for the reason that most people think. I like best practices. Because if I know what the best practices are, I know how to beat you. Because everybody just mimics the best practices. And here's the deal with best practices, guys. At least this is my belief of best practices. Now, granted, there are some core best practices that are just kind of like the foundation of running a business. I'm not talking about that. I'm talking about, like, how does the best agency in this category prospect? How does the best. You know, or whatever. Best business in your category do? Whatever. If I know how you do it right, this best practice idea shared by whatever industry trade group you have, then I know how to beat most of my competition. Because what they're doing is not thinking about, oh, how do I creatively solve this problem for my people, my market, the way we want to Solve it. I'm thinking, well, this agency that I envy, or I keep talking about agencies because that's my industry, but this business over here, I envy them. So I'm gonna do it the way they do it, right? But that's what works for them and their culture and their mantra and their mission and their core values in the market that they want to serve. That doesn't mean it's going to work for you. But so many businesses get locked into. If I don't do it this way, my board, my investors, my, my peers, my, whoever are going to think, think, think I don't know what I'm doing or they're going to question me. I look at Best practices as literally a blueprint for how to beat my competition. Because I know the vast majority of the companies in my, in my industry are going to do it the way these best practices say. So now I can go, okay, best practices have X number of producers per account. Great.
Yeah.
Okay, how do I do that better? Because I know that's the way they're doing it and I know what they're paying people, so I know what their cost of acquisition is. Okay, so how do I beat that cost of acquisition? Okay, I got to hire these people, I got to align them this way. Okay. I got to adjust the way I do business a little bit. It's a little more difficult to manage people who have a free wielding schedule. A lot of trust involved, a lot of loyalty that has to be there. But, but as you said, I can get there faster, quicker. I can get there in a way that, that I want to serve them. Because I'm not. My ego isn't tied to best practice. I'm.
Yeah.
Rogue Risk, which was the name of my business, would never in a million years make a Best Practice report. Never. It would never make it.
Yeah. You know what's really cool about that is, you know, with, with the model that you put together. And I think this is another piece of insight. It's like if, let's say you're, you're competing with a company down the street, whatever, whatever your niche is, right? And to your point, everybody does it this way, right? And you go and choose of the 10 things. You just go and choose two and say, what if we did these two things this way differently? How would it, how would it kind of land? What I think is interesting is you, is you said you told your team the what and the why. So here's what I, what I want you to do and the why I need you to do it. But you left the how up to them in, in much, in much of the way, right, you know.
Yes, yes. So there, there was a day. This is this. I'll tell you my, my most proud day ever. At Rogue Risk. We're. This is after we got purchased for the first year after we got purchased, we were basically left alone, which was great. Unfortunately, eventually. And just be careful, guys, when you sell the penny, be ready for them to kill your baby. So the last year, the last year was fine. You know, I hit my exit and we, you know, whatever is all good. But like the last year, I basically just watched them slowly knife my baby as they put best practices into our business that killed what made us different. Doesn't matter. Different story. But I'm sitting there one day and I looked at my calendar. It was empty. And I, and I'm like. So then I text my. She actually still works for me today at the company that I run today. Oh, she, I just brought her with me. She's the best. Her name's Clarissa and she won't listen to this, but if she ever does close. I love you. You're the best. I hope you never work for anyone ever again.
Sure.
Yeah. Except for me. I hope you never work for anyone ever again.
But I, so I text her and I'm like, hey.
I got nothing on my calendar. She's like, yeah, we're good. I go, what do you mean? She goes. I go, what about that? She goes, oh, yeah, we solve that yesterday. I go, well, we were talking about. She goes, yeah, yeah, no, Friday afternoon, after we had the call in the morning, we got all together and we solved that problem too. And I'm like, so I'm like sitting.
There going.
To go to vacation. What do I do? What am I supposed to do?
She's like, I don't know, go golfing or something. She's like, I don't, She, I go, she, at one point, she says, she goes, look, at this point on the, on these particular issues, she goes, if you get back involved, it's just gonna things up. And I was like, it was like this moment, dude, where I, like, I, I, I, I don't want to say that I cried, but like, I, I felt like this like, emotion of like, holy, it's working. Like, they are, they, they, like you said, they understand what we're trying to do and they understand why we're trying to do it. And they have taken ownership of the how because they know they can, they can, they can screw up.
Yeah.
And, and and later that day, we had an all. All, all team, all hands meeting because we had an issue that came up that we just wanted to talk about. Not a bad issue. And, and. And what happened was we had made a mistake. There was a mistake happened, and we needed to address it. Not like to blame anybody, but to kind of say, hey, guys, you know, we can't do this. Yeah, we don't want this to happen again. We just want to make everyone aware. And the woman who made the mistake, I did not call her out. No one, except for a couple people on the executive team, knew that she was the one that. That caused the problem. She actually stopped the meeting and said, guys, I want you to know that I'm the one that messed up. And I. And she said, and it won't happen again. You know, whatever. And she started. And I said, hey, hey, stop. You're good. You're good. Everybody screws up on this team. Everybody, Myself included, probably me more than you guys. I said, you're good. I go, we're having this call not about you. We're having this call so that. So that we just let everyone know this is something that could happen. We need to be aware of it and not let it happen again.
Yeah.
Okay. Meeting ends. She calls me after the meeting, and she's in full tears, just bawling on the phone. And I'm like, I don't know. She's like, I didn't know what to expect. I didn't know why she was crying. It took her, like, a minute or two to pull herself together.
Yeah.
And I said, you know, I just said, what? What? Her name was Sam. I said, sam, what? What's, you know, what's up? Like, you know, I. She goes, I've never worked for a place that I can make a mistake like that and not worry about getting fired. She's like. She goes, I went into that meeting and I wasn't worried about getting fired. That's why I spoke up. She's like, I wanted. I wanted to take ownership of it. She's like, but I've never worked anywhere that I didn't. That I could mess up. And not worried about getting fired because. Because the key is, guys, her mistake was not. There was no malicious intention in her mistake. It was an honest mistake. Right? So, like, why would I fire someone? It was a big mistake. Don't get me wrong. Yeah. It was an honest.
Was a malicious.
It wasn't malicious in any way. And I was like, I'm not going to chastise you. I'm not going to blame you. Right? Yeah, sure. If we had let it get too far, my license would have been jeopardy. The agency's license could have been jeopardy. We solved it. No problem. But like, but, but why would I let. I was like, yeah, of course. Like the thought never even crossed my mind. And she was just like, oh my God. And my point is not stroking what I'm saying. My point is when you create a culture where people feel, where people feel like, like they can, they have ownership of these ideas, it is, it is a, it's more difficult to lead because you have to be able to give them leeway. But what you get out of them. She, after that, after that meeting, she had her three consecutive best sales months she ever had in her career for our team after that because she was so like jacked up about like where she worked. Like, like, oh my God. And it's, it, this is, this is what it's like. It is tough to lead this way, guys. This is, this is a harder path, but.
It's a harder path, but it's a truer path. And it goes back to the alignment. It goes all the way back to alignment congruence. You know, we got about 90 seconds left. And one of the other things I want to, I want to bring up is just super fast. Is one of the things you actually mentioned when you said, your team member said, well, actually Ron, if you got back involved, you would screw it up. Right. I want founders and CEOs and visionaries to understand.
That when it is working, your guttural instinct is going to want to re.
Engage.
That's you actually getting ready to throw a grenade in it. Right. I've done that thousands of times by accident. Because that also means your self worth is tied way too much to who. To who made it happen. Right. So I wanted to kind of touch on that because.
No, it's perfect.
And then the culture aspect of having the culture already there where a key team member can say, right, dude, no offense. Love you. You're awesome. You grew this over here really well. But if you get back involved over here, it's going to mess things up.
Yeah.
To have that level of transparency and honestly, I think showcases your level of leadership and how you go about leading and how you build teams. In the 90 seconds we got left, we. I meant to bring this up a whole lot earlier. We got so engrossing conversation. I know where to go, but you have a brand new program where you're now actually coaching.
Yeah.
And helping CEOs and get better at what they do. And as you know, that's close to my heart. That's one of the things I love doing. So tell the audience about it where.
They can get guys. So I have a tremendous amount of free resources. If you go to finding peak, so finding P A k dot com finding peak performance, tons of free resources. It's a substack. So there's like a very inexpensive paid version. Most of that is I just want people to get this knowledge and I share kind of my leadership thoughts program, you know, the different structures that I use, mental models, etc. I do do one on one leadership coaching. It keeps me kind of grounded. I love working with founders and if you have any interest in that, you can email me. And if guys, if you just have questions you don't need, it doesn't even have to be about doing business together or whatever. Ryan, finding peak.com. that's my direct email. Feel free to email me with questions, thoughts, whatever. And if you do want to work together, happy to have that conversation. But dude, I, I appreciate you so much. Like, I like. Dude, since we connected, like I, you know, you probably get sick of all the times I like your.
Oh, not at all. Keep it coming, man.
No, I just, dude, I'm so in line with it. I, I'm so. It's such an honor to be here with your community and I just appreciate the hell out of your work and you know, we're becoming friends. Is Ben, I really love it, man. It's been amazing and I'm looking forward to. To kind of spending more time together and getting to know each other even more. So thank you.
Likewise, brother. Well, I can't wait to do this again. We'll definitely do a part two. We. We basically touched on about two of the 25 questions I had. So the good news is the audience got a masterclass on leadership because I believe your, your way of leading is. Is very similar to how I believe leadership should be done. We lead by example, not by ego. And I think you delivered on that numerous times. I think chasing, not chasing status and chasing congruence is like, like, I literally think this has changed. This, this, this simple reframe is changing people's lives and hearts and businesses. You know, one, one listen or one view at a time. So dude, I can't thank you enough, Ryan for coming on the show, bro. We'll definitely do a part two.
Thank you so much, man.
All right, take it easy, buddy. See you. Hey guys. I hope you enjoyed that amazing conversation and if you want more just like that to help you level up your life and your business, you're not going to miss this next one. Check it out.
Brand building. Now, because of AI indexing is imperative for the future of any professional. Because I talk about branding and I talk, I use that analogy all the time. Like the writing's on the wall for my industry that if people don't establish a personal brand, the next 24 months, they're not going to be in the business.
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