The Radical Power of Self-Belief

Tim Ludwig: Mike, I’m super excited to talk because I think you’ve got a real hero’s journey, a narrative to your life. And so maybe as a jumping in point, 13 moves before the 12th grade was your childhood experience. Can you say more about that?

Mike Botkin: Yeah, first, I appreciate you having me on, and I’m going to tell my wife that you think I’m a hero’s journey so I get some brownie points with her. But 13 moves growing up, I guess there’s two ways you can look at it. You can look at it from a negative point of view in terms of the disruption that that causes in someone’s life, and it definitely caused disruption in my life in a lot of ways, or you can look at it as a positive. The one thing that didn’t happen was I didn’t move city to city to city to city like you would see in the military. So my 13 moves were all local to our kind of community. And the positive side of that is, A, I got really good at packing. So I’m really, really good at moving and packing as an adult. But two, even though it was all within a city, you do get to meet new people and experience different sides of the city. And what it really taught me now as an adult is the value of stability, which I think that is a positive outcome of those things. But sure, yeah, moved quite frequently as a child due to various circumstances, largely financial with growing up. I grew up in a single mom household. It was just my brother, myself and her, and that caused us to move quite frequently.

Tim Ludwig: Besides being able to pack really well, were there other things looking back that you would ascribe to that as being benefits to your life that you picked up from that time?

Mike Botkin: Well, I certainly don’t know if it’s a benefit due to the moving, but I think one of the things that shielded me from what more of the negative thoughts would be or the negative assumptions of that is athletics and sports. My brother and I were very, very involved in athletics. If we were not in school and we were not sleeping, we were playing sports. And that kind of shielded us from a lot of the negative things that you would think about someone that has to move 13 times in their childhood. And what that caused was us to grow really good relationships with coaches and friends and friends of other parents, which there’s a story in there that led me kind of into my entrepreneurial journey. But I got to spend a lot of time at friends’ houses and with their parents. And we never felt like we were poor to a certain- like I wasn’t even aware of it. I knew the difference of wealth and I knew the difference of my friends that had really nice houses and drove really nice cars. But because my mom was at every single game, like she made it an extreme point to be at every single game of mine and my brother’s growing up and she hit that about 98% accurate. Sometimes we played at the same time. So an aunt or cousin or whatever would split. But to me, I felt a ton of love on that side and a ton of just awareness that my mom’s there. And I had friends that had big houses and their parents owned this, their parents did that, and they were never at events. Sometimes we gave them rides, or they’d stay at our house. And so, from a monetary standpoint, sure, there was a lot of disruption in that and the negatives that happened with that, but from a human level, we bonded in that regard. All of my memories are about going to sporting events or in tournaments and going to this and that that revolved around my brother and I’s athletic journey. And so I thought that was great. It really tied us together in that form. And when I did start to understand about the money aspect and why are we moving so much or the topic of conversation just became more vocal at my house with my mom, it really created a sense of I’m not going to be able to do certain things in life due to a parent giving it to me. So I have to kind of create my own path and my own journey. And that really gave me a fighter mentality, I think, and a fight or flight. And I really started forming a mental mind frame around I can either feel sorry about our circumstance, I can feel sorry about us moving, or I can deal with it and find the best in it. And I can find the best way to get out of this scenario. And that is the one big takeaway. And I don’t know if I’m jumping on you or not, Tim, but one of the big takeaways I have from my childhood is it’s up to you to make happiness. And it’s up to you to create your outcomes. And I guess it could be all based on someone’s own perception and their own upbringing and their own life, but I never had sympathy for someone that didn’t try to create their own success in life. I firmly, to this day, believe my life is directly the result of the things that I do to make it that way, positively or negatively.

Tim Ludwig: Yeah, so you’re really high agency. It’s interesting, I saw something posted online recently that was a question asked about how do you train someone to have that dog in them, I think was the expression. And my takeaway from that or sort of distilling it down was high agency and fierce ambition, the people that are going to go out and make things happen. And I think it’s a really interesting question. And some of the responses to this post online, a lot of them actually cited adversity in childhood as one of the key drivers. I’m not sure I believe any of this, but it was a common thread that appeared through the comments. And what do you think of that? Is there a way to teach somebody or is it natural born? Does it require adversity?

Mike Botkin: I think it’s a difficult question because I think we all have survivorship bias or selection bias to our own journey. Like my initial reaction to that is absolutely, adversity creates that dog in you. But throughout my career, one of the schools I became a teacher at was a very, very upper class school. It was an all boys Catholic school. Kids are driving Range Rovers. Like, it’s insane. I barely have money to get gas to put in my car, and these kids are driving $100,000 cars. It’s like insane. And my perception of wealth, of kids and how you should be raised going in was completely altered because I saw kids that had everything given to them or had all the opportunities in the world and they were as competitive as you could ever be. Like they had that dog, and it was about sustaining or achieving and the growth mindset and I’m going to outdo my parents. I’m not going to let this kid get into Notre Dame and I not get into Princeton. Like it was that competitive. So my answer would have changed. My answer would be different prior to that. I don’t have a good answer. I can tell you what happened for me and what I think created a dog in me, which I do believe I have. I think being aware of surroundings and making a conscious decision and effort and actions in my life to say, I do not want to be like that. I do not want that to happen to me. I want to be as far away from that as possible, meaning the lack of financial freedom in your life. So it created in me a competitiveness to, I need to do anything I can to not be in that scenario. I need to be good at this, I need to do well at this, I need to think through life differently, I need to go the extra mile, I need to work the extra hour, I need to stay another day, like all those things, it was a constant driving force in me of I don’t want to live that life. So, I just got to be relentless in doing it because I don’t have some of the natural advantages that other people have.

Tim Ludwig: Yeah, that makes sense. So, there’s sort of this fire in your belly, it sounds like, that came out of this. There’s lots of emotional stability, as I’m paraphrasing you, even though there might have been some physical location based instability. You’re still part of the same community. Your mom was very involved in your life and engaged. You had the sports community that you relied on. And now you’re coming to the end of high school. What’s the future look like to you through your 17, 18-year-old eyes?

Mike Botkin: Yeah, not good. It was not one of like, oh man, this guy’s going to be- I was not voted most likely to succeed, I will tell you that, as the high school senior kind of thing. It was bleak. I have a weird relationship around educational learning. I think school is different than educational learning, but that mindset’s kind of been developed over the years. I was not a good student. I mean, if you could write a bare minimum definition, my picture would be next to it. I actually went out of my way to find a way to not do good in school in the sense of, I remember this, I had it on a spreadsheet and I would look and see what my grades would need to be on the syllabus of certain tests to just pass the class. I didn’t want to do any homework. I didn’t want to do anything else. I just wanted to do exactly what I needed to do to pass. And part of me kind of being, I thought it was funny at the time, but I would tell teachers like, I don’t need to do your homework because I can just score a 75 on your test and I’ll pass the class. I wasn’t the most liked student either, if you could believe that. But it wasn’t great. But for whatever reason, I, at some level, knew that I needed to continue education. And I knew that I needed to improve. And one of the ways to get out of a scenario, which I thought was through education and my goal and my dream in life was to be a teacher, ironically, and a basketball coach. And it’s kind of funny going back to growing up, but one of the reasons why I wanted to be a teacher was stability. They have insurance, they have health insurance, they have a salary. And I graduated high school in 2008, so the Great Financial Crisis and financial instability was all around us. And I thought being a teacher where you had a set job that was never going to go away was very, very impactful.

Tim Ludwig: Were there any teachers that were really impactful or like mentor-like to you? I think when people become teachers, sometimes there’s that character in their lives that emerges at some point in their school, and they’re like, oh, that person had an impact on me. I want to do that for others. Was that your experience, or was it more just around this like, this is a time of uncertainty, I want the stability, I like the government paycheck and like that they’re probably not going to fire me at any point?

Mike Botkin: I wouldn’t say it was teacher specific. I would say it was more around the coaches of my life growing up. My favorite teacher to this day was my middle school basketball coach, who was a teacher, and then my high school basketball coach and the football coaches, and my cousin was a teacher, and her and I became very close. And so the people that I had close relationships to as adults to me as a child were coaches who happened to also be teachers. And I wanted to be a coach, so I had to become a teacher to do that. And that was kind of a theme in life as I kind of work backwards on things. I want to be a coach so what are the steps I have to do to do it? I need to pass a class. Well, what are the steps I have to do to do it? Sometimes I would do the bare minimum. Sometimes I would go the extra mile in life. So yeah, so I ended up kind of hacking my way into college, and I, through basketball, made an introduction to the basketball coach at the University of South Alabama and got in there. And I took education a lot more serious in that regard because I had to now pay for it. It wasn’t something that was free. And it was one of those things like you can make a couple, you can go down a couple of roads here when you’re in college. You can slack off and kind of get the bare minimum out of it or you can get the most out of it. And I didn’t have any scholarship money. I was on government assistance. I was on the FAFSA, the Pell Grants. And then to pay for the extras, which was not a lot, I started playing poker to make ends meet and to pay for meals and to pay for rent. And I formed relationships with people.

Tim Ludwig: This is online poker or in-person poker in poker rooms?

Mike Botkin: Online poker at the time. I was too young to go into poker rooms and there wasn’t any. So I went to the University of South Alabama, which is in Mobile, and there wasn’t any good poker rooms around there. So it was all online. And I credit a ton of my success as a business person to my formative days of playing poker, which I’m more than happy to get into. But it’s kind of the summary of my educational days of I was a complete slacker throughout high school, and in college, it was just a means to an end. And I don’t have a ton of takeaways from the educational standpoint, other than it was something I had to get done to become what I wanted to be.

Tim Ludwig: Yeah. I want to go back to just that senior year in high school again because I think you skipped over some parts that add a little bit of color to the challenges that you were facing. I mean, you were not living with your mom anymore that year. You had gotten into a little bit of trouble, like there was some instability before, but it sounds like this was you really sowing your adolescent oats and potentially going down a path that would have not made college or a lot of what’s happened since then possible.

Mike Botkin: Yeah, for sure. So a couple of weeks prior to my senior year, I ended up moving in with family members and changed family members throughout my senior year of high school, which that is not the most optimal time to have instability in your house is your senior year of high school. And with that, I had kind of a lack of discipline in my life, to put it lightly. And I started hanging around with kids that were going down a bad path. And I got caught up into some of that, of just being around that and not really doing anything bad myself, but just being around that environment created some adversity and potential where if I would have made a decision left or right, and it would have been the wrong one, it could have impacted me for the rest of my life. And going out to parties and going out to clubs that I had no business of being at while I was in high school, a college club or a college party while I’m still in high school on a weekday, on a school night because no one’s there to make sure I’m in bed or no one’s there to tell me what to do. And getting caught up into all those sorts of things that come with that was right there at the edge, on my fingertips. And for whatever reason, luckily, I kind of skated by that and got away from that. And it’s a time that I definitely reflected on in my early, mid-20s. I was like, man, I think life can go multiple ways here. Is it going to go left or right?

Tim Ludwig: And were the kids that you’re hanging out with, were they good kids just doing bad things, or were they bad kids that were just not going to be good, positive members of society? And I say that because I hung out with some of both kinds of kids at around the same age and, thankfully, got involved in some of my own shenanigans but without any lasting impact. But there’s some resonance there in terms of that being a fork in the road. And had I just been in the wrong place at the wrong time, some things could have ended up very differently.

Mike Botkin: I think products of environment. It was a group of about four or five of us. They were all older than me by a year or two. And none of them had great home lives growing up. None of them had stability with parents. None of them had a great direction in life, kind of all basic random jobs, just trying to figure it out and not in school. And I think you become a product of your environment. So I was around kids that did not value school. I was around kids that had meaningless jobs. And so that’s what I was headed down the path of doing. I will say they are good people. I’m obviously biased in that because you have fond memories, just like you have negative memories. Still friends with two of them to this day, and they’re both healthy members of society with kids and working good jobs, and they’ve kind of also pivoted their life and made good for them. So obviously super happy for them. I would say the other half of the crowd was probably not great.

Tim Ludwig: Yeah, it’s interesting. I’ve got a teenage son now, and I was once a teenage boy, as I mentioned, and so I know what kind of trouble they can get into. And it’s amazing. I just think if you can make it past, as a boy, if you can make it past like age 25, your odds of- make it to age 25 without something catastrophic happening, the odds of longer-term success get much, much bigger because I just know that me and my friends did so many stupid things through late adolescence where we had the means and the availability. We were driving, there’s vehicles involved, there’s like all the things you can get into as an adult, but without the good judgment of a more mature adult. And it’s kind of like a miracle that we largely, most of us make it through pretty unscathed.

Mike Botkin: We didn’t discuss this, but as you were talking about the vehicles and adolescence and bad items, it brought me back to a memory, which may not be shielded from my head, but one of those friends, my best friend out of that group, who I am still friends with to this day, who is a very healthy member of society and great kids and great wife, he was actually in a car accident where the passenger died due to some late night shenanigans. At the same time, I remember the same time, I got a call in the morning about 6 a.m. saying, oh my God, from a relative saying, like bursting in tears, crying, oh my God, I’m so glad you answered the phone. And what’s going on? What are you talking about? And it’s this person got in a car accident, and they said a passenger died and they didn’t say who it was yet at 3 am in the morning. And I look back, and they went to a place that I would have definitely went to with them. It was a scenario that I absolutely would have been a part of. And I don’t remember the exact reason why I didn’t go that night, but I chose not to go for whatever random reason. And I definitely would have been in that car. And I always was the front passenger with my buddy. And circumstances change, but could have been you, could have been me.

Tim Ludwig: Yeah. And instead, you ended up as the first person in your family, as far back as people can remember, to get into college.

Mike Botkin: Yeah, absolutely. It’s crazy how life works. I think some of that was luck. I think some of it was, who knows? But yeah, I think choosing which road to go down is vital in someone’s life. And I think as parents, which I’m a young parent now, I think the best you can do is provide them information, data, and scenario outlays of if you make choices like this, these are the likely outcomes. If you make choices like that, this is the likely outcome. I didn’t have that, so I was just kind of winging it on my own, and I think far too many kids do wing it on their own. But I know you as a parent are probably way more active and guiding and giving advice, which I think I commend you for, which is great.

Tim Ludwig: I was sort of chuckling to myself listening to you talk about that because you’re talking about these probable outcomes and before that mentioning poker, which you have to calculate a lot of probabilities in your head all the time. And you and I have talked, and you’re really big on that, right? Like you do these whole sort of decision tree diagrams and weighted probabilities and like you run a not insignificant part of the major decisions of your life through a process like that.

Mike Botkin: I do, and poker built that into me. I was always- oddly enough, I hated math growing up. I couldn’t stand math class. Like it was my worst subject by a mile. I mean, by a mile. But, and think about this for a second, I used to get the newspaper, the physical newspaper, every single morning. Our school had it, for whatever reason. And I would get it and I would read just the stats in the sports section. I would just sit there and read stats and stats and stats. I would get on the computer in the library and look up ESPN stats, and I would memorize all these crazy numbers. And then I would start to think, well, if Trace McGrady with the Orlando Mavericks, he’s averaging 28 points a game, if he scores this, this, this, he will be the scoring leader. I’m doing all these mental math models in my head about probabilities, which I wasn’t aware of at the time. But then I’d go to math class and I’d fail every test and pass on homework. I had probably an authority problem. But as an adult, once I got into poker, it was just second nature to me. Everything started clicking. And a huge part of poker is thinking through and predicting probabilities of outcomes. And I took that with me, and I still practice it and carry it to this day. And I think it’s a huge- I can’t make a decision without it. I’ll say that. I have to go through that process with every decision. My wife screams at me when it’s like, what do you want for dinner? And this is like nuts, but it’s like, where do you want to go for dinner? And I’m like, all right, well, it’s going to take us 20 minutes to get to this place. That means we’ll get back at this time. Well, it’s going to take us 15 minutes to get here. I go through all these dumb little unconscious things in my head to make a decision. And it’s just second nature to me now. But it definitely, 100% comes from, I think, poker really was the muscle on that.

Tim Ludwig: When you make a decision using that process and it doesn’t work out as you expected, meaning it falls into one of the lower probability outcomes that you’ve drawn on your diagram, does that make it easier to absorb the outcome for you? Because you’re like, oh, I already considered that this was a possibility, and so I was playing the odds, and it didn’t shake out my way.

Mike Botkin: When it was something I considered, certainly. When it’s something I wasn’t aware of or I didn’t consider, like the most annoying part of it is when something happens, and in retrospect, it was so obvious, like that was a possibility, and it’s like, oh my gosh, how did I not think about this, how did I not understand this, which I can give examples in a business sense. It’s like oh my gosh, I’m such an idiot. But when it’s a scenario you plan out and it’s definitely probable and it happens, like that’s part of it. You’ve got to take a swing sometimes. You’ve got to be aware of what the second order effect of that for me is and I spend much more of my time thinking this part through. Here’s the negative outcomes or the outcomes that would not be favorable to me, how can I mitigate those as best as I possibly can? And then what would be the scenarios where it would still end in a negative result? And how do I react to those or what are the repercussions of those?

Tim Ludwig: One of the frameworks that has stuck with me mostly because it’s simple and my memory is pretty bad is sort of a two by two matrix of process and outcome. And so you can have good process, good outcome, bad process, good outcome, things like that. And ideally what you want is to start with something that starts in the good process thing. Because there’s luck that exists in most scenarios. And so you could have a good process but a bad outcome. And if you’re doing something on a serial basis, meaning repeatedly, eventually the odds just tip in your favor if you’ve got a good process.

Mike Botkin: 100%, and I’ve taken a lot of bets or swings in my career. And from the outside looking in, it’s like this is the dumbest thing this kid’s ever done in his life. But I’ve already thought through the negatives. Like what that built for me is, whether it’s a mental map or me writing out notes and notes and notes on things, which I became accustomed to do, it’s certain times in my life, I would make a decision, I think through something or I want to do something. People in my life would be like, oh, well, did you think about this? I’m like, yeah, I did actually. And it became a sense of like I always had an answer for something. In a negative way, that was the perception of, oh, he knows everything. He has everything figured out. And I was always like, I kind of do. Like that was my approach like, I better have something figured out. I better have all this planned out or else I’m not qualified to make this decision. And I’ll bring this to today’s kind of segment, but I get searchers that reach out to me and, hey, I’m going to buy this. And I’ll ask two or three very basic questions like, what about this? What about this? What if this happens? It’s like, oh my gosh, I never thought about that. And there’s a level of experience that I have to ask some of those questions. Just like I’m sure if I had something and you looked at it, you’d be like, Mike, this is glaring, like an issue here. But I can’t stand when someone’s like, I didn’t think of that scenario. And it’s like, how do you not? Like, how do you not think about the bad things that could happen? And listen, I deal with that, I have two kids, I deal with that on a daily basis, so people not thinking through decisions, but it’s definitely helped me in my life. By a large order of magnitude, that has been the most consistent thing that I would attribute my success to.

Tim Ludwig: Coming back to your life story here and coming out of college, you’d set at least a tentative ambition to become a teacher and a coach. And coming out of college, it sounds like you achieved the goal right away.

Mike Botkin: Absolutely. I was thrilled. I was a basketball coach and I was a teacher, the two things in my life that I loved by far the most in my life, and it never felt like work to me, so the teacher side didn’t bother me. I enjoyed it. And the basketball side was a passion of mine. So my days were filled with happiness. I had a salary. I had a job that I loved, I didn’t think it was a job, and I was doing my passion. I was coaching basketball. I probably would have stayed in that job forever if some of those formative things didn’t happen earlier in my life around the finances. And maybe this coincided with just where the economy was at the time. But I went from a place where having a $38,000 or $40,000 salary as a 23-year-old is like, holy cow, you can go buy any house you want in the city, you’re great because it’s a financial crisis and the houses are beyond cheap. And I think being a teacher where you don’t really value money, but you value time and lifestyle as a 23- or 24-year-old, which most do, it’s like the best thing in the world. You get summers off, you get Christmas break. You hang around with buddies still because you’re off at three o’clock. As you get older in life, money starts to matter because you want to buy a house and you want to have kids and you want to do all these things. And I remember a moment, I was sitting in the teacher’s lounge, and I was surrounded by- one of the benefits of being a young teacher is you’re surrounded by older people. So you get their perspective. And for whatever reason, I was always aware enough to shut up and just listen when they would sit in the lunchroom and talk. And I remember a constant theme was teachers continuously talking about seven years, ten years, five years. And I was like, what is that? And they would say, until I retire. It’s like, what? Like you’re counting down until you retire? Like that is- you know how fast-  life is a very precious thing, my friend, like be careful of that. Or they would always like, yep, 12 more days. It’s like 12 days for what? It’s like 12 days until our paid holiday break. I couldn’t live like that. That stuck in me to my core that I did not want to live a life of counting down the days until I didn’t have to go to work that day or counting down days until retirement. I absolutely did not want that in my life. You match that with the cost of living and my age going up, you’re not being a roommate with five dudes anymore, you’ve got to take on some responsibilities here. And one of the things for a professional life that I realized was, and this is still true to this day, and I hate this, I really took pride in performance. I took pride in being good at everything. I took pride in studying. I took pride in learning. I took pride in being a good basketball coach. Like I did things that other people weren’t willing to do. I would stay up until three o’clock watching film. I would be a good teacher and make sure I’m finding different techniques of how to teach things in the classroom. Some are visual, some are written, all those things, some are oral. And I just started thinking through, well, at the end of the year, I don’t make any more money than I make. I make an extra $400 than I did last year. No matter how good of a teacher I am, like the same guy that’s complaining about his life and is counting down to retirement, he’s making the same money I am. He’s actually on a better pay scale. And that was a professional thinking that this seems unfair to me. And then on the athletic side, where my passion really derived from of why I was there, I was very fortunate enough to reach the mountaintop as a coach, a high school basketball coach. You dream and you do all this work, all these hours and practices, and you work so hard to reach the mountaintop. And what is the mountaintop? The mountaintop for us was to send kids to college and to win a championship, the state championship. I became a head coach at a very early age. I was the youngest in the state of Florida to become a head coach at the time. And I caught success very early. We were very successful, especially relative to the school history. So I’ll skip up a little bit. Our team ends up winning the state championship.

Tim Ludwig: How many years into your coaching were you?

Mike Botkin: Four. Four seasons. Yeah, four seasons, I think. Four or five seasons. And so I remember we win the state championship. And listen, this was my, Tim, when I say this was my dream, like this was the peak pedestal, like send me off to wherever I’m going to go at the end of life, that’s what I wanted to accomplish. And we did it. And I remember we win the championship, we’re celebrating like crazy, your moment of like, yeah, we did it. And then we all stand in line. And I don’t know if you’ve ever seen this in a high school level, but like the commissioner of the state will go by and it’s like the Olympics, they walk down the line giving people medals. And we’re in the arena, there’s 10,000 people there. And I look up, and everyone is going so crazy. Everyone’s so happy. The team is happy. Everyone’s crying. It’s the best ever. And Tim, I felt nothing inside of me. Absolutely no joy inside of me. I felt a pride. At the time, I didn’t know. At the time, I thought I was just caught up in the strategy and the game and we had to win. And oh my gosh, it’s only been ten minutes since we’ve won. I think looking back, because I’ve had a few other peak moments in my life, especially one recently, I value the climb. I value the journey. I value the- I wanted the championship, but I took joy in the practice. Like there were coaches that are like, I hate practice time. Like, let’s get to the games. I want to be in the game. And for me, I love practice. Like nothing made me happier than planning the practice, scheduling the practice, being at practice, thinking through things, working through issues, like making it work and making it all come together. And I realized in that moment, I realized that much later in life, but I realized my first recognition of that moment came during that day when I finally reached the pinnacle of what people spend their life searching for and trying to reach, relatively speaking, it was our state championship. And I felt zero joy in me, zero. It was scary. It was very scary because I thought it was supposed to bring me something it didn’t. And it was like, man, that next season, Tim, we were still very successful. I was missing something in my life. It didn’t mean the same to me anymore. Because I’ve reached the peak and I knew what it tasted like. And I didn’t- Something was just making it- and I wasn’t aware enough to put it all together yet. As I tell you, I was in my mid twenties still, and I wasn’t able to put it all together, and I felt like when you couple the financial issues, the career trajectory, and that piece, my passion, it’s like the saying, don’t meet your hero because you’ll meet the real person. I met my hero, and I met the real person, and I needed to look for another avenue.

Tim Ludwig: So if achieving big goals like that doesn’t bring you the fulfillment, where do you find it? And did you have to reorient yourself, to retrain yourself somehow to do that?

Mike Botkin: I don’t know if I have the answer yet. I don’t know if there’s- because in life, we’re so predisposed to have, have you being goal-oriented and then you want to achieve a goal and then, that sort of thing. And I don’t want to say a new challenge is what energizes me because I think there’s value in stability and value towards long term things. But I think what energizes me is the input, maybe. I’m just thinking through as you asked that, and I apologize for a little bit of a delay. But I’m thinking through some of my next journeys, the next kind of big professional things that I did, and none of it was with an outcome in mind. None of it was with, oh, I’m going to do this. It wasn’t. It was more about, I believe in the mission, this is a good opportunity, regardless of what the financial constraints are, which I guess we can talk about next in my next part of the career, but it was more about believing in the mission, in the work that it took, and I felt satisfaction in every single step of the way, accomplishing that piece of work, as I’ll call it. Like, what’s the problem today? What’s the problem this month? What’s the problem this year? Let’s go accomplish them, and the strategy around doing that is what really brings me joy.

Tim Ludwig: Yeah, I think what I hear other people say most often is it’s the process or the journey. That’s where I really find the deepest fulfillment is when I’m in the trenches working on the thing that ultimately if I’m successful, leads to that goal. But the goal is almost anticlimactic at that point because if you’re doing all the right things along the way, that’s when you’re working with the team, you’re setting the strategy, you’re grinding it out every day, building that esprit de corps and the shared sense of mission and purpose, and then you get there, and sometimes not only is it anticlimactic, I think it’s almost a letdown. Because now, now what are we going to do. Like, this was so good, it was so much fun before, and now the journey has ended. And I think it also points to the difference between people that look for motivation extrinsically versus those that do it intrinsically. Like if the objective is exterior to you and what you’re about, it’s hard to be satisfied because once you achieve it, there’s nothing left and then you have to set another bigger goal. But if you’re finding the satisfaction internally, it’s always there.

Mike Botkin: This is like a very odd way to look at things, but I look at those external moments that you would normally celebrate, the championship or this or that or when we’re selling a business, I look at that as just validation of my contrarian way of thinking was right. Like that’s honestly how I look at it. Like when I was fortunate enough to be a part of a couple of exits throughout my journey in business or winning a championship, and it was just validation of what I did was right. And not that I needed validation from external people, but to almost myself, like I went a little contrarian here, I went a little off the grid, or I went a little awry, or man, I put all this work in, got it, we did it. Okay, what’s tomorrow?

Tim Ludwig: What does it mean to you to be a contrarian thinker?

Mike Botkin: A contrarian thinker to me is something that or someone or a way of thought that is not commonly done and in the beginning is looked at as not the right way to do it or not the most probable way to do it or not the path that’s already been done. And I guess in my own weird definition, I’d probably say that, like thinking of another way to do things than what has already been done before. I pride myself on that to a fault, I think sometimes of being a contrarian thinker. It gets me in trouble sometimes. But more often than not, it’s been right. And I think the exercise of that, Tim, is going back to kind of the poker stories and the mind mapping and the scenario and the probabilities, it’s contrarian to you and contrarian to the public, but I’ve thought through all the negative scenarios and I’m okay with it. So I’m okay being contrarian, because more often than not, if I’m right, I’m going to be really right.

Tim Ludwig: Does it make you feel like you are sort of in perpetual outsider status?

Mike Botkin: Totally, absolutely. That’s a great- I don’t know if you picked that up intuitively or not, but absolutely. I am a constant, no matter where I am in life, professionally, financially, regardless, there’s always, I’m an outsider and I got to find my way in, I got to find my way to win, I got to find my way to beat it, I got to find a way to do something that like they can’t do or I can’t do what they do, so I got to be creative, I got to be different. That’s a great- I don’t know if you picked that up intuitively or not, but…

Tim Ludwig: I don’t know. Is that a source of edge for you too? I mean, Josh Wolfe of Lux Capital, a big venture capital firm, talks about chips on shoulders put chips in pockets. So I’m sort of riffing off of that. As an outsider, does that like make you want to prove to yourself and society that like you are going to be seen as an outsider for a long time, but you’re probably going to be right, and there’s something that validates your purpose and pursuit by doing that?

Mike Botkin: I think, so go back to when I won the championship. We won the state championship, we were underdogs, should not have won, and in the following year, we were favored to win the championship, and we didn’t. And I hated that year. I absolutely hated that year being the favorite, not because, oh, I don’t like being a favorite, but there was no dog left in me that year. You can coincide that with the championship or not, I don’t know. The next business we went to, we were clearly the underdog to the Goliath in the room, Microsoft. And we were constantly battling, scratching and clawing, doing everything we can to win. The next phase of my career, it’s trading off of a person’s balance sheet; a family capital balance sheet is much different than an institutional balance sheet. And so we were the underdogs. We had to be creative. We had to find ways to get margin. We had to find ways to get deals no one else saw. And then I go do a landscaping business, and it’s a terrible business. I got to find a way to climb out of it. And I don’t have 5,000 trucks. I don’t have this and that. And then what I do get in- Every single step of this, I was always placed, at least internally in my head, real or not, created an underdog mentality. And so, yeah, I think to answer your question, it’s a perpetual living in the underdog world having to prove it, real or not.

Tim Ludwig: That’s really cool. I want to ask one more question about the teaching phase of your career, which at the beginning, you said that you view education and learning as different, and it sounded like you were not such a fan of our model of education as a student. How did you fit into the system then as a teacher in that system?

Mike Botkin: Well, this may take all my teaching credentials out the window, but I was a PE teacher to start with, so luckily a little able to lean on that side. I did really enjoy, and again, this may be shocking to you or not, I really, really enjoyed debating other teachers about everything. I mean, pick a topic and I would debate them. I ended up getting into administration. I was a director of admissions at a private school. And I just really disliked the way we did things from an educational standpoint. It’s one of the few areas we- no one wants the government to run their life, but we’re okay letting them raise your child. And it’s like, how does this work? And I think the education system does not teach to mastery. It teaches to peer age levels with a focus point on not learning the material, but on advancing you through to make it someone else’s problem. And I despise that. I don’t think, I mean, Tim, you and I have four hour long conversations about this because I have a whole idea about reshaping education. I don’t think education should be lumped together with age groups. Nowhere else in life are you siloed with people your age. It’s about your abilities or how good you are, how can you master something. And far often in the education world outside of private schools, that’s how you’re lumped together. If you’re eight years old, you’re going to be next to eight-year-olds. If you’re 12 years old, you’re going to be with 12-year-olds, regardless of how skilled you are or how quick or not you’re learning material. So I really despise that. And I think as an adult, I started learning things much different than I did as a student. Like I could not sit there and listen to someone talk for 45 minutes and then take the material and go do it. I needed to be interactive with it. I needed to read different viewpoints on it. I was constantly asking why, why this, why that? Why are we doing it this way? Like, who says that guy’s right? And now today, as an adult, when I’m reading on a subject, I want different viewpoints because I want to learn both sides. The history books are written by the victors. Well, I want to learn about the guys that lost. One of my favorite books who your buddy Moses Kagan recommended to me, it’s a book called Losers. It’s about guys that ran presidential campaigns and lost. And I want to know their story. I want to know why they lost. Go back to the contrarian comments, like I just want to be different.

Tim Ludwig: Yeah, there’s a bit of a theme here that I’m picking up on. So after you left teaching, you did this little stint at a sort of bootstrappy startup company in the sports analytics world to add some transformational impact there, I think, or as part of the team that led sort of, I don’t know if it was quite a turnaround, but certainly brought it to a level of success that it hadn’t had before. And then I want to sort of jump over that and then talk about you being recruited into this other type of organization, which you sort of touched on a second ago, which is this family office-backed platform.

Mike Botkin: Yeah, so when I left the startup, when we exited it, I was able financially to kind of take a breather and look around and see what I was going to do. And I got introduced to a guy locally in Orlando that is a developer and involved in real estate. And I say real estate private equity because that’s the best way to describe the functions we were doing, but it was all off his balance sheet and off some external outside capital that was raised via family members and high net worth individuals and family office guys. So it wasn’t institutional capital by any means. And there’s two different- there’s very distinctive operational and goals when you have family money or your own money versus institutional money. So, I got hired there to kind of lead their sports division and create a sports division and create sports athletic complexes. And shortly in my tenure there, I got called into a meeting with the CEO who was going to Asia and the Middle East to go raise money. And one of the things our business did was we not only built real estate assets, but we managed them, we operated them. So we built a hotel, we operate the hotel. What I mean by operate is we literally operated that hotel. We decided on what cups we’re going to use, we decided on bed sheets, we put the brand up, we hired the general managers. We were a high end hotel to this hotel. Same thing with our restaurants, our water parks, and all the other assets, our property management business. So I am just over mid-20s, I was 27, I believe, and he brings me into the office. I think he’s going to fire me, quite frankly. I’m walking in this office, I think this guy’s going to fire me. And he says, hey, I’m going to go away for a little bit of time to Asia, and I’m going to go travel and raise money. I want you to look after the place for me. And I was like, what are you talking about, look after the place. So anyway, I’ll skip forward a little bit. I ended up becoming the COO there in my mid to late 20s. And that was very transformative because I got put into a situation of blind trust by this guy of his own money and his backing and the returns are likely predicated on the success that my inputs have at these places. And I had to learn how to manage people. I had to learn how to manage adults of all various skill sets and age demographics and financial statuses. I had to learn different asset classes and different businesses. Like I know far too much now about how hotels work and how restaurants work and water parks work and the property management business and service lines because I had to. And I had to speak knowledgably to these people that were my new direct reports. And I went in with kind of an underdog mentality of I’m just some young kid that no one knows why I’m here. No one knows what- I have no credentials. I was a teacher four years prior to this. And so I kind of had to prove myself with knowledge and willingness and being able to jump in and learn and jump in and do. And that set me up in my life, I think, really well and really kind of honed a lot of skill sets in me.

Tim Ludwig: I think this journey is incredible. Like, you have constantly jumped into the deep end in parts and industries where you had no prior experience, were tasked with succeeding, and at every turn, you’ve done it. I mean, the coaching is probably the closest to what you were trained to do. You growing up in the sports world and then focusing on that in college, being an athlete, being around coaches. So that path and that next step, like I get that. I mean, becoming a successful leader and turning around a program and winning a state championship in four years is maybe an exceptional part of that story. But then, now I’m going to go do software sales and operations. Now I’m going to become the CEO of this real estate private equity holding company before I’m 30 and manage all these different businesses and have to work with people that are much older. I mean, it is remarkable. And not only because of the success you’ve had, but I think even the willingness to do it, and maybe it’s foolhardy, you just have this irrational belief in yourself that like what’s the worst that could happen? And I think we talked about that at one point. But it’s just incredible to me. So I don’t know, just as an editorial there, but it’s remarkable.

Mike Botkin: I appreciate it. It means a lot coming from someone like you of recognition. I think one of your comments is spot on. It is complete irrational confidence. I believe I can do anything. I truly believe that. I think if you put me in a scenario, I will find a way to be successful. And sometimes that means I’m just naturally gifted at it. Sometimes that means because I’m going to not sleep for three days and read about what restaurant margin should be. And why are we putting 12 napkins on the table when that costs us two cents a napkin? What if we put no napkins on the table? What if we- I spent an enormous amount of dedication and time to being successful in every single role I did, and I would find creative ways to make it successful. I would learn from the ones that are doing it kind of the normal path. I went and visited other restaurants. I would talk to restaurant owners. I went to restaurant conferences, and I started seeing which- I’d start walking into restaurants and I would look, how are the tables facing the door? How are the chairs aligned? Not at our restaurant, go to McDonald’s, go to wherever. And I would just study and study and study and dedicate my life to making sure this was successful for my own purpose of I wanted to succeed and not fail. But you know what? Someone’s money is important here and our job is to do this. And I think this is a very overused phrase, but I think failure is not an option. Failure is an option. What are you doing to prevent it? And I wasn’t going to let a restaurant fail because I wasn’t prepared.

Tim Ludwig: I think that also takes a tremendous amount of humility. I mean, I don’t think you’re necessarily a humble person. I think you are in some ways, but like, there’s ego there. I think most successful people carry like this high self-belief. I mean, there’s a lack of humility in even saying that and having that irrational belief in yourself. But to step into the roles that you did, I think you have to humble yourself in order to be successful. You have to be willing to ask the dumb or the obvious question or the beginner’s mindset on things and like challenge convention, like why do we have a napkin here today instead of no napkin? And walking into an environment where you’re the least experienced person in the room, but still in charge from a hierarchical perspective, that’s unusual. Did that come naturally?

Mike Botkin: It did. And I would put some of that to learning people. And I would guess through poker and through coaching in those early years, you understand as a coach, most coaches, when I tell you, Tim, who is your high school basketball coach at your high school? It’s going to be some crusty old guy usually. I was 21 and 22 years old being put in charge of kids who are three years younger than me. Some of them, we could have been in the same high school in an odd way. And then I also had their parents. And so I had to learn how to adapt and read situations and think through people differently. And what gets the most out of Tim may not get the most out of Johnny or get the most out of whoever. And I had to really be aware of everyone’s skill sets and everyone’s surroundings and what motivates them. And how do I need to talk to you? How do I need to present to you? And then in poker, it’s the same way. You have to be hyper aware of everything. Your hand is on your chin. What does that mean? Is that a pattern? Is that a tell? Is that confidence? Is that weakness? And so when I went into a scenario where I knew nothing, I mean, I barely was old enough to check into a hotel by myself and get a rent-a-car. And one of the things I had to do was I had to learn, and I had to sit there and observe and be okay asking questions in a humble way, be okay asking things not in a condescending way, being able to input in that same direction. And I think when you’re vulnerable with people and they see it’s coming from a genuine place of, hey man, I just want to learn, like I do not know anything about this. Can you please help me on this? Or why did we do this way? I think people are much more receptive to that. Teaching people or showing them, I think if you qualified and presented the right way, if I would have went in there and said, I’m 28 years old, I’m the best thing since sliced bread, look at what I am now, COO of this firm, like you guys are going to- we’re going to do this, I would have been laughed out the room and I would have been gone. So for me, it was about gaining respect of others. And I didn’t have the credentials to be respected, but I was going to be respected via work ethic, humbleness, as often as that doesn’t fit me. But just being able to be a team player, be a listener, and take input. And then when you do bring suggestions or you do bring new creative ideas, they have to be impactful. They have to be thought through. They have to be kind of in the right direction of what our goal is in this. It would have been very easy for me to walk into the hotel and say something or make a decision. But if I didn’t have any substance behind it, it would have been sought through immediately by people that are experienced in that industry.

Tim Ludwig: See, this is also fascinating to me because what you’re talking about involves a lot of emotional intelligence, being able to read the people and to shift your style and to be humble when you need to and get out of your comfort zone, all of those things. But at the same time, you’re incredibly contrarian, you are direct to the point of bluntness sometimes. And it’s like people are complex, obviously, but on this one hand, I remember the first time we talked, I came away thinking like, Mike is a super smart guy, but he’s a little bit of an asshole. And that’s not the- and you’re not, obviously, and I think you’ve worn off some of the rougher edges over the past few years since we first connected, but that isn’t the initial impression or the first impression that you would get from somebody that then talks about like being able to work with a wide variety of people in a wide variety of circumstances. It’s just another one of those really interesting things about the complexity of who you are is that they don’t naturally, in my head anyway, go together.

Mike Botkin: I think understating my mindset growing up or not even growing up but as an adult wanting to be a success, I think that was the sign. I never wanted to be lucky. I wanted to be successful, not in spite of me. I didn’t want luck to play into it. But I was going to be successful come hell or high water. And to a fault, I had to box out a lot of other things, relationships with friends, relationships with other people, sometimes how I speak to people. To me, it was, I have to be direct with you because I don’t have time or I don’t care about anything else. I just have to go. Or this is what we have to achieve, and your feelings are not in my list of priorities of outcomes on this. So, there was a lot of rough edges of being singular focused and not really caring about what other people thought. And I think to the negative, I think that hurt me in a lot of relationships. I think your reaction to me was very consistent in my life of asshole and direct. And I think my best friends, the friends that really knew me, it was always when that was said around me, and I was very aware of it. And quite frankly, I started kind of wearing it as like a badge, like I didn’t care, which you always do to some level. But I remember my friends constantly saying, but you don’t know him. You have to get to know him or you have to talk to him versus the exterior was asshole. And I brought that upon myself clearly. But that was also what made me so singular focused on winning was I have to do this.

Tim Ludwig: Yes, it’s super interesting to me. And that actually, the explanation just connected some dots for me. So thank you for that. So we hit, I think, COVID, and the world changed and many things look very different. And the business you were with was going through its own version of the challenges associated with that time period and you now decide that you’re going to step into a new role, and I’m sure you built out the decision map and weighed the probabilities. What was the calculus you were going through at that point?

Mike Botkin: Yeah, it’s kind of a thing in my life of taking risk financially. I was in a very well positioned seat at the firm that I was at and making more money than I ever knew what to do with in my life and had things coming down the road that would have changed my family’s life for the good. But there was a couple of pieces that were missing in that puzzle, and I wasn’t happy. And COVID definitely played a major, major part of that, being stuff that was promised and agreed to kind of fell apart in a lot of ways. And I remember talking to my wife about this. I’m not in control of my journey here. Like someone else controls my journey. And she was pregnant with my daughter. And I said, and this is the dumbest thing that I say that people always look at me like I’m an idiot when I say this, but I felt like I was in the backseat of a Mercedes with a seatbelt on, very safe. Like I have a great driver and we’re moving forward and everything’s going great and I can live my life in the backseat of a Mercedes. But I always had that entrepreneurial itch. I always had that, I want to go prove it, itch. And I didn’t feel like I was proving it anymore. I felt like kind of we made it a success and we’re just rolling now. I wanted to go see if I could prove it on my own. I wanted to get out of the car and go drive a Honda or a Kia or whatever car the visual helps for you. And I’m going to drive it. And I may crash and burn this bitch, but I’m going to be the one driving it to crash and burn, not someone else. And if I do it right, maybe it’ll be a Mercedes one day. And if it’s wrong, I believe in myself enough that I can go find a good job. That was the decision tree. Like if this doesn’t work, what’s the outcome? The worst outcome, I had to go look for a job. Pretty confident that I can go get that. And the lessons learned along the way would be great. I had to take a shot. I had to take a shot mentally for me to know and be safe, to quiet my brain of, can I do this?

Tim Ludwig: How did you sell Chelsea, your wife, on that? You said she’s pregnant at the time, you’ve got this good job, stable paycheck, and you say, I’m going to just blow all that up and this is what I want to do.

Mike Botkin: It wasn’t a singular decision, that’s for sure. I think she recognized unhappiness for me leading up to that. I’m very vocal with her about things that are going on in life, even though I compartmentalize with everyone else. And she knew the person she was with. She knew the fire I had. She knew the desires that I had. And the thing that kind of changed everything for me, as I always thought, I want to be my own boss one day, I want to take my own shots one day. I never did it, probably out of fear. Her commitment to us doing it is what changed everything. Her commitment was, I’m in this with you, let’s ride or die. You have to take a shot. I support you a hundred percent. And you would hope your spouse is that, you would hope your significant other is that. But I can tell you, when I told my family what I was doing, going from the seat that like no one ever- like I hit the lottery being in the seat over here, to I’m going to give it all up and I’m going to go buy some tiny landscaping business. Like landscaping, I kind of like, I didn’t mow a single lawn. You know what I mean? Like it’s insane. My mom cried and said it was a bad decision. And my brother had a few other choice words in there, like I’m throwing everything away and this is stupid and I’m going to regret it. And oddly enough, if you go back to our conversation so far today, I still talk about this to this day with my wife. We were sitting at my kitchen room table and I remember my mom doing that, my brother doing this, and I have to create enemies for whatever reason. I just do. And I use that still to this day of no one believed. No one believed we could do this. No one. And look at what we did. And that subconsciously probably fueled me in a lot of ways.

Tim Ludwig: Yeah, the unspoken support of a partner in I think people’s entrepreneurial journeys is vastly underappreciated.

Mike Botkin: Totally. If she would have said, I don’t- if she would have even wavered of, I don’t know, I wouldn’t have done it. I would have always regretted not doing it. So I’m glad she at least recognized that. Even if she didn’t believe it, she externally energized me to do it. But I never would have done it if it wasn’t her pushing me.

Tim Ludwig: And in my life, the stability and support at home is honestly part of the fuel that allows me to go out and take bigger risks outside my home because I know that I’m coming back to a safe place that’s going to help bandage me up when it’s rough out there and that I’ve got the unwavering support of the people that I love and care about the most.

Mike Botkin: I think I mentioned a story to you before, but there’s a story about one of the emperors Marcus Aurelius and the peasant he had. So he was an emperor, king and all that. And he had a guy sit behind him while he was sitting on the throne, a peasant who would whisper, you’re only a man, you’re only a man. And so now I tell Chelsea, you were my belief that I could sit on the throne. Now you’re this guy behind me telling me I’m only a man. I’m only a man. I’m only a man. So, as she builds me up, she tears me right back. So it’s a great- having a supportive spouse, while Chelsea was a stay at home mom, so it wasn’t like the financial security. Like we were all in, man. We were in. I mean, this lived or breathed by me, lived or died. But her emotional support and intelligence and wherewithal of supporting me and helping me in guidance and advice meant the world to me, meant the absolute world to me, and really was a big pillar of success, which I’ve heard you discuss your wife at numerous times and eerily similar support of a belief.

Tim Ludwig: Yeah, it’s amazing. Tell me about just the factual side of the first business you bought, and then I want to hear about your development as a manager and leader.

Mike Botkin: Sub million dollar revenue, not even sub. I say that and people think I mean $980,000. It was doing like $750,000 of revenue. SDE, as I’m air quoting, of like $150,000, but when we really boil it down, it was like $20,000 of free cash flow. It was terrible, it was an absolutely terrible business. It was a mix of residential and commercial landscaping, more residential than commercial. It was 10 minutes from my office, so I was like, all right, this seems good, let’s do this.

Tim Ludwig: And what did you walk into in terms of the actual business? Was it good team, good contracts, like easy sailing? You just put your foot on the gas and grew and smooth sailing?

Mike Botkin: Phenomenal brand locally. It was a 45-year-old business, and there were two owners only in the 45 years, and their reputation for quality was off the charts, which is really what sold me to look around everything else. I was like, as long as I don’t fuck the brand up, I can figure all this other stuff out. And I didn’t know what I didn’t know in a lot of ways, but I went in with that. I will tell you, you spend your whole kind of journey in this, like, what’s my opening speech going to be? How am I going to rally the troops and we’re going to be marching and they’re going to be my guys. And leading up to this, the owner was telling me his number two guy or number one guy, however you want to frame it, is like the most rock solid guy ever. He’s going to lead the charge. He’s going to be your guy. He’s the best. So I corral everyone together and give my little speech, and he cuts me off and says, I’m never working for anyone other than that man. I’m gone. So, I didn’t even finish my speech, and this guy is like walking off. And you can imagine visually what that disrupts in the team. It was 16 to 18 guys, two of them were his family members, so I say 16, and then now 15 because this guy is no longer here. And I knew nothing. I knew absolutely nothing. I never did one of those prior. It’s much different walking in and buying a business when you’re well capitalized, it’s like a real team and stable. Buying a true small business, that was tough. That was hard.

Tim Ludwig: Did that moment, was that a moment of terror?

Mike Botkin: It was like, oh shit, this is real. Like, this isn’t going to be easy. It was a very bad business. It really was. If someone showed me that business today, I’d say, well, what the hell are you doing? It is by beyond stroke of luck that that thing succeeded in a lot of ways. Bad assets, no cash flow, no, I didn’t even negotiate working capital. Like, I knew nothing. I knew nothing about it. I didn’t negotiate working capital. It was terrible. And it was a really bad business from that sense. Great reputation in the local residence, bad business. It was not a business. Bad labor aspects, all that stuff was really bad. It should, I mean, all intents and purposes, it should have failed.

Tim Ludwig: This whole business ownership chapter was a very short term, right? What was it from buying that business to exiting, how much time?

Mike Botkin: If you include that one, it was a total of 29 months. I was- what people more see now, it was a 23-month journey. And so, yeah, there was a few inflection points in that, and definitely, I learned how to be a business, I would probably say I learned how to be a good manager at my prior firm. I learned how to be a business owner in those few months because everything was on me, the entire world was on me and it was not going well. And in those moments, you can fight or flight, you can figure shit out or you cannot. And I had to figure it out from a very low level of a business owner, but it meant the world to me and my family. I had to make this work. And so we did some things that made it work. And within a couple of months, we doubled EBITDA projections and things were starting to kind of turn and you would see some decisions work out well and ended up going and raising money to go do this on a much larger scale. And that just put fuel on fire and created opportunities of luck to happen and opportunities of scenarios to happen and ended up acquiring six landscaping businesses from that moment over the next 20 months in the next thing.

Tim Ludwig: When you jumped in that first six months, that sounds to me like 100% management. Like you’re in the trenches, you’re turning the cranks, like you’re not even a player coach at that point, you’re just kind of a player and trying to do whatever you can to right the ship and get things moving. What were the key management lessons for you then?

Mike Botkin: It’s a great question because I am always vague when I say that. I was definitely more player, and I happened to be a coach from like 9 p.m. to like 11 at night, but I was a player. I guess the management lessons were, I never had to really flex this muscle before, but I had to learn business, I had to learn unit economics, I had to learn business licenses, I had to learn when people- I couldn’t just tell people, no, they’re not getting a raise and that’s fine, because I have an application from 400 people ready to go who are dying to work at this firm. Like, it was, if I don’t keep this person, like we don’t have a driver anymore. And so I get like all those small business things of repercussions. And thankfully, I’m able to go back to my muscle from earlier, I was able to think through scenarios. All right, 50 cents a year. This means here, if I don’t have that, this is the negative impact on that. So I was able to really flex that and really start to get to know and see the value of relationships in management where they held all the cards. At my previous firm, I really held all the cards because, again, you wanted to work there. At this place, your competition’s 500 feet across the street. Like they can go work anywhere. And I had to really make sure I created an environment where people wanted to work.

Tim Ludwig: What was the transition between that and stepping up into something that, because you did a lot from just like a leadership perspective or an owner perspective, whatever we’re going to call it, from this in the trenches management, maybe actually doing a little bit of leading from, at least coaching from nine to 11 at night. When did it start to shift where you actually were starting to focus more on working on the business, as they say, rather than in the business, starting to think about building a team, the architecture of the organization, creating culture? I mean, in 29 months, like you didn’t probably have a lot of time to even do that, but when did that start to shift where you were starting to get out of the weeds?

Mike Botkin: One of the benefits of me, which helps with time, is I have a huge bias to action. I don’t let things play out for long periods of time if they’re not working, or if I have an idea and it’s well thought out, I will put it into play. And then I have an ability to adapt quickly if it doesn’t work. It is truly a skill set that I don’t see in many people. Bias to action coupled with ability to change if need to. And so I was able to implement things and become a manager and all those things. Our first real acquisition, which was the largest residential provider in central Florida, that came with middle management. That came with scale. So I had to learn how to integrate the two businesses. I had to learn how to, all right, I’m not the guy dealing with the labor now. I have someone else dealing with the labor. So I was able to kind of go back to my previous workplace and start managing managers, a little less sophisticated than those managers. Like there wasn’t financial experience there, but I was okay dealing with that. I would say by our fourth acquisition is when- well, let me back up. On that first real acquisition, one of the things I was aware of from a previous firm and the little bit of time I had being solo is people matter. And I went out and recruited a general manager from Chick-fil-A to come into the industry. I went out and recruited a dean of students at a school. So what’s really good with a general manager of Chick-fil-A? Empathy, sympathy, and customer service, and fast-paced movements and fluctuations of various financials, brought her in to handle that. What is a teacher and administrator in a middle school of a lower income area really good at? Managing the emotions and the psychology of people from less than ideal circumstances and backgrounds. What is our labor pool? Matches that. What is our customers? Matches Chick-fil-A. So I went out and got people that were experts in those fields that I could recruit and obtain. And then I was able to kind of move up in more managerial ladders. By our fourth acquisition, it was full blown culture and needle moving and strategy and integrations and all sorts of that. By our fifth acquisition, our fifth out of the six, we brought in a CEO or acquired a CEO as part of an acquisition. And I went from being very involved, at least knowing what was going on with general managers and acting as a de facto CEO to being completely hands-off. This is now someone else’s baby. Gosh, I hope the steering wheel works. I hope everyone has seatbelts on. And then our sixth acquisition, which was a new platform, I did the same thing. I acquired a CEO and he was off and running to the races.

Tim Ludwig: What was the hardest of those transitions to make as you sort of went up that leadership ladder?

Mike Botkin: I should have known this ahead of time because I did experience a little bit, but when it’s yours, it’s different, I would say. Understanding that people can do things completely opposite of you, and it doesn’t mean they’re wrong. When at previous firms, like you have some people come in with different ideas, like five degrees to the left or five degrees to the right. No one went like totally against the grain on anything, any of our decisions or how I wanted things structured because I was involved. But when I stepped back and like meetings turned into this structure, as simple as that, like a meeting structure, or is there meetings this day or how do we look at this, like completely different. I mean apples and oranges, black and white, everything was different. And I had to learn, I shouldn’t say learn, I had to be okay with there are a lot of other ways to do this and do it right than just mine. And I had to be okay with that. And my job went from, once I got over that hurdle, my job was to just make sure I’m relating. I don’t care how you do it. This is your show, you do it how you want to do it. I need to be supportive to you. I want to be helpful to you. Just make sure there’s always a rhyme or reason on why you’re doing things. It’s okay to fuck up as long as we know how we got there and we can change after that. So it went from much… It went to… I relate it completely to coaching. I can draw up the best play in the world, but once the whistle goes and the ball’s in play, it’s up to them to do it. I felt like that with our CEOs. We can strategize and have a board meeting about how we’re going to do this, but as soon as the whistle goes or as soon as we walk out the door, you got the ball, my man. Like, I hope all the muscles work.

Tim Ludwig: And which of those roles felt the most natural and the most fun for you?

Mike Botkin: I take joy in the journey, so I take joy in bits and pieces of all of those. I would be lying if I said the true operator with a real management team wasn’t fun, because I had a ton of fun of that. I had a ton of joy with that. But nothing was more satisfying, it’s kind of a cop-out answer because nothing was- that was very satisfying. Like I did this, this was my strategy, and this worked. I have an ego like you wouldn’t believe as you pointed out. And I love seeing that. But when you can discuss and decide with something and let someone else handle it and see the fruits of that, like that’s awesome. Because your ideology has to work now, your thought process, there’s no more, you can’t will this to success anymore. You have to be really strategical and tactical. So I really enjoyed that.

Tim Ludwig: Good outcome, you sold to a larger consolidator, and they had a team in place. And so you were able to, I think, hang around for a little bit in some capacity but were largely sort of able to transition out pretty quickly and which sort of brings us to that is a pretty monumental transition. Like you’ve had enough of a financial success in that outcome that you didn’t have to go back and get a job right away or look for the next business right away. And did that cause any disequilibrium, or was it just sort of a natural shift and you were happy to sort of punch out for a minute and just kick back and relax?

Mike Botkin: This is a very interesting topic. It goes back to us winning a state championship. I felt nothing about the exit. The day of the transaction, I felt nothing. I was miserable for a couple of days. And I was miserable not because of what it meant or what it did for everyone else, but just miserable because like, now what? And I gave up what I really enjoyed. Very happy for everyone else. Very happy for us. I mean, my job above anything else was to return capital to our investors. And I did that. I did that plenty, above and beyond the expectation. And then we created wealth for our family that is unprecedented, and it gave me a ton of freedom, and then it created financial freedom and security for a lot of other people in the organization, which I take phenomenal pride in. Like, that’s full stop, an extremely proud moment of mine. Jekyll and Hyde I think in a lot of ways, like I think we sold early. So there’s still some unfinished business left there that I have still in my head, but it’s not my business anymore. So someone else has to run with it. But I did always go back to, I’d rather sell early than not be able to sell later. And so you have to live with those decisions. In terms of moving forward, I was able to transition out. Literally the day of closing, it was, all right, Mike, thanks a bunch. Which that was kind of a kick in the balls, to be honest. I was like, wait, are you sure? I can help you here. I can do this. And they’re like, no, you’re all good, man. I think I negotiated a little too hard on some aspects. I rubbed someone the wrong way. It’s interesting because I felt like I was at the peak of my intellectual learning and emotional learning of how to manage things and do things, and I’m still very young. I’m 30, I just turned 34 in January. And so I’m getting into my peak, and then it all stops and there’s nothing there. And I don’t do well with boredom. I live below our means. It’s actually been pretty tough.

Tim Ludwig: So how have you confronted that?

Mike Botkin: I think taking time to do things that I don’t think I’ll have time to do in the future or it won’t be as readily available in the future or things that I regret in other people’s lives, like I take my kids to school, both of them every single morning. I pick them both up every single afternoon. And my wife and I- like that’s going to stop eventually. I’m going to have to go get a job eventually and like become a big boy again, and I’m not going to be able to do those things, but I hope I have enough time and enough meaningful conversations and moments with them where, in 10 years, they’ll be like, oh yeah, I remember when dad took me to school. Or at least for me, I’ll have memories of talking to my son on the way home, or just him and I in the truck and no one else in the car, talking to him about his day or just stories. So I think creating memories from situations that aren’t readily available when you’re a professional, I’ve really focused on that. I’ve really focused on a relationship with Chelsea. Like I’m here. I don’t have an office to go to. I don’t have calls to be on. Like I am here with my wife. And I think really taking the time to explore our relationship has been great.

Tim Ludwig: If you could take what you know now, post-transaction, about settling into this new interim state that you’re in and rewind the clock and have time to prepare for what was coming afterwards, is there anything that you would have done differently to get ready for stepping outside of running and owning a business?

Mike Botkin: Assuming with your question I can’t say I already have other stuff lined up the day of closing, so I’m going to take that out of the equation. I don’t know because I think you actually told me this before, like there’s not many 34 year olds I could hang out with on a Tuesday at 9 a.m. Like it’s a very unprecedented situation. So, in looking back, I don’t think there’s anything that could prepare me to make this more fulfilling or better post transaction. I do think I needed this family time. I went very hard for a couple of years, probably overly. I overdid it in a lot of ways. So I think I needed this kind of reset time. I needed time to sit down and read a book. I needed time to just go pick up my kids. I needed time to do that, to do that to kind of get out of the fray, so to speak. So I don’t think I could have done anything to prepare for it, but it feels like in retrospect it was needed.

Tim Ludwig: Maybe phrasing the question in a different way, if you were friends with somebody that was about to go through a transaction, say it was six months away, and they were looking down the barrel of the same scenario that you were in, what advice would you give them?

Mike Botkin: You’ve got to find a way to keep purpose. So much of my purpose in life was tied to the business and how we were doing it. I mean, that’s what I thought about 99% of my day. I think the mental transition, anytime something’s not yours anymore, it’s tough. So I think if you told me you’re a business owner, you’re going to sell your business in six months, I would tell them to understand the separation of yours versus what’s not yours anymore. Like it is not yours anymore. So prepare for that. Be okay with that. Because some people sell and they really regret it. And they can’t let go mentally of the business whether it’s successful or not. I was somewhat able to kind of check out of that pretty quickly. And I think my experience of having CEOs helped a ton. So I would say that and then find a purpose that you can attach to quickly and move on to the next thing. And I don’t think that really answers your question, because I’m still learning throughout my journey, Tim. I mean, it’s been only a few months and there’s still days and peaks and valleys with my own exit as well. I will tell you, I wouldn’t trade it in. I think creating financial security for my life and freedom to say no, which is an overused phrase, but the ability to say, I don’t want to do that anymore, I don’t want to do that or I’m not doing it is beyond rewarding personally, but then creating a path where my family never has to live- Go back to the very beginning of our conversations where I said my entire goal was to make sure I never went through that again, where did everything I could to not have that happen. And outside of me colossally fucking this up, my family will never have to go through that again.