From the Mat to the Boardroom: Iron Mike Steadman on Grit, Branding & the Power of Action
What does it take to get back up when life knocks you down? In this episode of Executives Unplugged, Iron Mike Steadman - collegiate boxing champion, veteran, entrepreneur, and business coach - shares his journey from the boxing ring to the boardroom, revealing hard-earned lessons on resilience, branding, and the power of action.
Mike takes us inside one of his toughest leadership moments: running a nonprofit boxing gym in Newark, NJ, when COVID shut everything down overnight. With his back against the ropes, he found a way to pivot, reinvent, and build something even stronger. Now, as a sought-after business coach for veteran entrepreneurs, he helps others define their brand, find their market, and take decisive action in the face of uncertainty.
🔹 Key Takeaways:
•How to turn adversity into momentum—even when you feel stuck
•Why action builds confidence
•The power of niching down and owning your brand identity
•How to battle imposter syndrome and step into leadership with clarity
•What it really takes to sell yourself and your business with conviction
Whether you’re an entrepreneur, leader, or someone looking for the mindset to push through tough times, this episode delivers practical lessons and real-world insights that will get you off the mat and back in the fight.
🎧 Listen now and take your leadership to the next level!
Mike Steadman: ironmikesteadman.com
Black Veteran Entrepreneur: Validate your business model, build your brand, and step into greatness
References:
Episode Transcript
Mike Steadman: 0:00
A guy named Mike Nemeth called me and he was like man, I'm just calling to check on you. He's like how are you doing? I was like man, I'm down on the canvas. He's like I know, that's why I'm calling. He's like you got to get up. We got to get back in the fight.
Keith Cowing: 0:11
Welcome to Executives Unplugged, where we dive into case studies and coaching sessions to elevate your leadership. I'm Keith Cowing, executive coach to CEOs and product leaders, and today my guest is Mike Steadman. Mike was a decorated collegiate athlete, he is a Navy veteran and now he is a business coach to veteran entrepreneurs, as well as a brand builder. And Mike has an incredible story. He is quite a leader, quite a human, and he's going to coach us on resilience and how to bounce back even when pressure seems insurmountable, and how to focus our brand and our offering even in a crowded market. But our story starts today in a boxing gym in Newark, New Jersey. Let's go. Mike! Welcome to Executives Unplugged. Thanks for joining me.
Mike Steadman: 0:57
Keith, man, it's a pleasure. I have not done nearly as many podcasts like I used to before, because I used to host a show, but you're the first. I think you're the first podcast I've been on in 2025, man, so it's a pleasure.
Keith Cowing: 1:09
All right, well, lucky me, good way to kick off the year, and we've talked a lot about business coaching, a lot about the work that you do. One of the things I love about leadership is it's all about different perspectives, different tensions, different stakeholders that you work with and getting exposure to a lot of different things. You had a really unique experience. You were running a nonprofit boxing gym in Newark, New Jersey, through COVID, and you had to deal with some serious leadership moments there. Take us into that moment and one of the decisions that you had to make, some of the leadership things that tested you as as a human, as a leader well,
Mike Steadman: 1:46
You know I go by Iron Mike, right?
Mike Steadman: 1:49
So people call me iron mike, and everybody assumes it's because of my boxing accolades at the Naval Academy and I was a three-time national boxing champ, two-time most valuable boxer, captain of my boxing team, etc. But the reason I call myself Iron Mike is because of covid. I had spent the last five years hooking and jabbing in Newark, New Jersey, teaching boxing, started the Ironbound Boxing Academy and felt like I was finally starting to make some traction. And then, as soon as the NBA got canceled during the pandemic I think it was like March 9th or whatever I just felt like like it was over. You know, businesses fail for primarily two reasons. Number one, no market need and number two, they run out of cash and virtually overnight there was no need for boxing. You know, the city of Newark made us close down our gym.
Mike Steadman: 2:36
At the time I was earning income teaching on-site boxing classes to company like Spotify, WeWork, NextJump, so I was like the head boxing instructor at Spotify, NYC and it just went away. It evaporated and I just at that moment I was just like this is it man, you know, and that was a very surreal feeling when it's like you spent all this time to build something and feeling like the rug was pulled out underneath you and I had a West Point grad, a guy named Mike Nemeth, call me and he was like man, I'm just calling to check on you. He's like how are you doing? I was like man, I'm down on the canvas. He's like I know, that's why I'm calling. He's like you got to get up, you got to get back in the fight. And I just started calling myself Iron Mike. And Then people started calling me that and now that's what everybody knows me, at least in the veteran entrepreneurial community is like Iron Mike. Nothing against Mike Tyson, he was great in the ring. But you know, my story is just a little bit different and then it is a little suggestive, right, the gym is the Ironbound Boxing Academy, you know? So the brand's Ironbound. But yeah, man, I had to give myself a ground punch. And it was funny too, because that experience really helped me gain some confidence, because I was able to bounce back.
Mike Steadman: 3:52
We ended up launching an entrepreneurial program essentially, and then the other aspect of it was all the goodwill I had built up over time. You know, when people start to support nonprofits. I was one of the first ones that they thought of. So we actually came out of the pandemic better than we went in. One of the first ones that they thought of, so we actually came out of the pandemic better than we went in.
Mike Steadman: 4:07
I spun up a new business model around podcasting as well. It was something I had in the back of my mind and we're going to talk about coaching. But I told my business coach that, hey, I wanted to do podcasting and he told me it was a distraction. But I was like, whatever you know, I still was reading the books, I still launched my podcast and then when the pandemic hit I was able to pull on that lever. But that would have never happened had I not nurtured those skills and I had prepped myself for podcasts for probably about a year.
Mike Steadman: 4:32
I met with some different kind of podcasts, early podcast networks, I read a bunch of books, took some courses online et cetera, and I had started my own podcast that I was able to essentially white label and bring to others and then it just kind of took off. So I know that's probably a lot to unpack there, but I think the moral of that really was just about the importance of kind of self-talk. You know, and that was my first time truly experiencing that. I don't want to say anything is possible, but sometimes you really got to dig down and save yourself because there were no guarantees, nobody made me do any of that, no one made me pull those pivots, pull those triggers, and I basically just couldn't sat down and been a victim. You know, I had to, I had to get after it and that's exactly what I did.
Keith Cowing: 5:21
Everybody's been in a moment where it just feels like the pressure is coming from every direction and you feel like you're on the mat, whether it's in reality or not, and you just can't imagine how you're going to get out of this situation. Psychologically, if you can handle it, if you can manage through - constraints and crises breed creativity and you said you came back even better. But that wasn't guaranteed. So in that that moment, how long did that last? Is this three months? Is this six months? Is this two years? What'd that bounce back look like?
Mike Steadman: 5:49
It was honestly about a week and a half because like again, so there's this book called
Keith Cowing: 5:54
That's fast!
Mike Steadman: 5:57
There's this book called the Four Agreements, and one of the things it talks about is never assumed. See, I assumed that there was no market need for boxing anymore, at least on-site boxing. So it was a wrap. I start to get calls. Spotify hit me up. They said basically, hey, can you teach your classes virtually? We got a bunch of people at home and stuff et cetera, and I was like let's go.
Mike Steadman: 6:19
But even before that, when Mike had called me and said we got to get back on, get up off the canvas, I knew we were a nonprofit organization. I also knew that there were a bunch of kids and families at home and so I got to do something. So one of the first things I did and this is important in those moments - just taking action. Sometimes any action is better than nothing. I start to go live on Instagram.
Mike Steadman: 6:41
You remember that when all the fitness instructors were going live? So I would just go on live and organize a daily workout for the kids at home. So I ordered a bunch of stuff off Amazon, I set my little camera up in my apartment in Newark and I started to go live every day at four o'clock and everybody would come on and I would teach my classes and stuff, and so I had got some reps in. So when Spotify, you know, and all these other companies start calling me ask if I could teach boxing online, I had already gotten some reps in, I had already had the equipment. So I was - boom - I was back at it. And it felt very humbling too at that time because it was like, okay, I'm still in the fight, I'm still able to earn income. This isn't bad, you know, but it it did introduce a new constraint that we're going to get into,
Keith Cowing: 7:26
And you're mentioning the kids.
Keith Cowing: 7:27
You're mentioning four o'clock, that every day, at four o'clock, I imagine having some structure, something to count on, something that is in your control, could make a big difference, I imagine, for the kids as well. When you talk about the people that were taking these boxing classes, talk a little bit about who were your stakeholders here? Who was counting on you as a leader in that moment to not give up?
Mike Steadman: 7:47
Yeah, our young athletes. So we target primarily youth and young adults between the ages of 10 and 22. And one of the reasons we say, you know, young adults is because in environments like Newark and other cities across the country, you might have people that graduate high school but they're still living at home, they don't have a full-time income, especially if they don't go to college, et cetera, and so, whereas programs tend to turn them away because they're now kind of young adults and they only want to cater to youth, we just extended that. I mean, some people call them opportunity youth, et cetera.
Mike Steadman: 8:17
But one thing about us was, you know, in the flywheel, the top of our flywheel was always focused on the impact. That's what it was, you know, and that can mean a lot of different things, but essentially it's like where can we make impact? And that's what motivated me to just kind of get up and get start moving. You know, doing some, doing those online workouts, and that was my way of making impact, because when I moved to Newark in 2015, I didn't have a gym. In 2015, I didn't have a gym, you know, I would just pick kids up and drive them to a local boxing gym. Pay the gym owner for me to train them.
Mike Steadman: 8:56
But that wasn't like a sustainable kind of business model as you start to grow.
Keith Cowing: 9:04
What did you learn about yourself as a leader going through that experience, figuring out how to do the self-talk, how to bounce back, how to operate under pressure?
Mike Steadman: 9:08
For a slight moment I thought I cured imposter syndrome, you know, because there was no one. That was literally one of those situations where no one was coming to save us. Yeah, that was. There was nothing, you know, and like I told you before, there were no guarantees, and so for me to kind of lean in, for me to make those decisions on my own. You know, I got an email from a board member that basically was like Mike, this is probably it. You know, now's the time to kind of look out for yourself and your future and yada, yada, yada, you know. And I just decided to kind of persevere and push through.
Mike Steadman: 9:45
Kind of persevere and push through, um, and like my background growing up, you know, I was raised in a single parent home. Um went through some challenging things in the childhood, especially early adulthood. My mom had a stroke while I was at the Naval Academy, so she's been basically basically bedridden in a nursing home ever since. Um, and and it's it's something that I'm working through these days is like you know, there's all these conversations about the meritocracy and stuff et cetera, right, like basically the sky's the limit.
Mike Steadman: 10:12
You know you can do whatever you kind of put your mind to, but until you experience it, until you see it, until you touch it right, it's hard to really grasp that. And that's not to take away from my success. You know, at the Naval Academy, being a Marine Infantry Officer, all those things that I set out to do, that I was able to accomplish. But man, business and entrepreneurship is a whole different ball game. You know, literally the ability to create value out of thin air with a laptop and a Google Doc and a microphone. For me to experience that created a whole new level of confidence in myself.
Keith Cowing: 10:52
Let's fast forward to that. You were in a boxing gym in Newark dealing with COVID. You felt like you're on the mat. You had to bounce back. Not that many years later, you're now a business coach. You're helping veterans that are entrepreneurs run their companies, get their brand straight. What did that transformation look like for you?
Mike Steadman: 11:11
It was gradual. I really looked up to my boxing coach at the Naval Academy, got a guy by the name of Jim McNally and you know, like I mentioned before, because my mom had that stroke at Navy that was my sophomore year, so I really kind of leaned into boxing as my outlet and that's one of the reasons I was so successful in the ring, and so I've always felt this personal responsibility to give back to a sport that I credit with actually helping me graduate the Naval Academy in the first place, and so that's what's one of the things that inspired me to move to Newark, start Ironbound, et cetera, and I saw myself like Coach McNally, like that's who I wanted to be. Like, I want to be a boxing coach, you know, and I want to be the head boxing coach at the Naval Academy, et cetera. But then I end up winning a grant in 2019 for twenty five thousand dollars from the Street Shares Foundation for Ironbound and right around that time, I went full time in Ironbound in 2018. This was back when social enterprise was like the buzzwords, right. So I had the nonprofit which was the Boxing Academy in Newark and I was standing up a for-profit, which were my on-site boxing classes and so I got a grant for $25K.
Mike Steadman: 12:21
But I felt like I was like all over the place. You know I lacked focus. I was like this is hard, I feel like I gotta. And I didn't know that I was looking for a business coach at the time. But I was seeking something and you heard these terms like executive coach or productivity coaches. I had no idea what they meant, but I just was assuming that that's what I kind of needed. So I won $25,000 from the Street Shares Foundation and Mike the same person that called me and told me to get up off the canvas a year prior he had introduced me to who became my business coach, Bill Watkins. So when I won that grant I hired Bill. I paid $6,000 up front because, again, I was seeking, I just knew I needed to help. I needed help, and so that drastically changed my experience of entrepreneurship and what to expect out of it. Because I had a corner man who kind of had that objectivity and was really focused on business, life and self and enjoying the journey along the way and making sure that we're accounting for the people on the exterior, right, your partners, your kids and et cetera, et cetera.
Mike Steadman: 13:26
But, having that experience and I really looked up to Bill and I thought in my mind like, oh, this would be cool to be a coach one day, like him. What I wasn't banking on was in 2022, he approached me about being a coach and talk about self-confidence and imposter syndrome. I'm like who the heck am I to be a coach? Right, I started a boxing gym in Newark, you know, on the nonprofit side, and then I bootstrapped this, you know, podcast branding agency. But like I'm not ready to coach yet. He's like Mike, you'd be a great coach. And that was, yah, talk about leadership decisions, Bill, somebody I looked up to he's a little bit older, wiser, has been doing this for years and I saw this as a window of opportunity.
Mike Steadman: 14:06
You know, you and I talk about value, for value, we can learn from a lot of different people and opportunities, et cetera. And so essentially it was like a Yoda Luke Skywalker situation, you know, and Bill trained me to be a professional business coach. We worked a lot on mindset first, the confident mind, what it takes to win, right, a lot of the athlete thing, because he knew what I didn't know, which was everybody assumes the coach got it all figured out. But then when you sit down on that screen and on the other side of that laptop, you know you got to deliver, you know, and when you're dealing with a CEO that's looking at you for that guidance and wisdom, it can feel a little intimidating. But yeah, I went six months without a coaching client and then at the six-month mark, boom. So it wasn't an overnight thing by any means. And then the first year you get those coaching clients. You're working on delivering value. But then over time you just kind of start to come into your own.
Keith Cowing: 15:05
Let's go back to the self-talk. You talked about imposter syndrome. You talked about self-talk. You went through that when you're on the mat in Newark with the gym. Now you're transforming into being a coach, and you've got these same types of moments. I'm sure there were moments of doubt that everybody goes through, of, yeah, is this really going to work? You go six months without a client. You got to have the grit and the fortitude and the vision and entrepreneurs deal with this. There's moments of is this really going to work? And it feels like the world's caving in on you and you got to have that, the self-talk and the self-care to be able to make it through that, along with the vision. How do you do self-talk? How do you get yourself through that moment, either emotionally or physically too?
Mike Steadman: 15:47
So I'm learning. Okay, I'm going to take off my armor here and get a little bit vulnerable. So I created this. I was reading a lot of books. You know How Champions Think, What it Takes to Win. You know The Confident Mind, right.
Mike Steadman: 16:00
And those were things that Bill had kind of, you know, recommended for us because I wasn't the only coach - there was a group of us that were learning you know how to be coaches and stuff, et cetera. And I would do my little affirmation, right? So I would have that affirmation, look at myself in the mirror and say I'm a freaking, you know, world-class business coach, yada, yada, yada. But you know what really helped more than anything else was getting the reps in just freaking coaching, taking a swing at the plate. You know having those calls and at one point Bill had recommended, he said, to be a coach. You got to coach. And to be a coach, you got to be able to sell coaching.
Mike Steadman: 16:40
And I had just written my book. I wrote a book Black Veteran Entrepreneur Evaluate your Business Model, build your Brand and Step into Greatness. And I said you know what? I'm just going to start coaching Black Veteran Entrepreneurs on the side, right? So I got the book. You know it's an easy sell on the marketing side and so I did get a few I don't want to call it low margin, but low, you know just some clients just to kind of get the reps in and have that. So even though I didn't have like clients at my ideal kind of rate yet, right, I was still coaching, I was volunteering, I was doing that on the side and that slowly over time, you know, was building my confidence up because I was getting more swings at the plate.
Mike Steadman: 17:16
You know you and I were going to talk about sales at some point and how many founders say they suck at sales and that they don't like sales, but yet how many of them have actually done like a thousand sales calls or a hundred sales calls? It's easy to say you don't like something, you're not good at it, when you've never done it, you know. But I equate it to like, you know, swinging at the plate like baseball. You know, if you do like 99 swings, you finally hit that home run. It's like, okay, now you get the experience of it. But to you know, do sales like, do like two sales calls and then be like I don't like it, I'm not good at it, you're not really giving yourself a chance, and so that was one of the things that I have learned. With regards to and it goes back to what we talked about earlier, it's like listen, man, forget what you think. Action, action, action.
Mike Steadman: 18:01
I thought writing a book was gonna make me feel like a writer and an author. It did while I was writing the book, but once the book finished, imposter syndrome again. It's like I'm not really an author. I don't really feel like a writer yet, but when I journal every day really feel like a writer yet, but when I journal every day, I freaking feel like a writer. You know why? Because I'm writing. One of the reasons I feel so confident as a coach these days is because I coach almost every day of the week with the exception of the weekend. So yeah, imposter syndrome it's there, and it was definitely there when I moved to Newark, because my best friends were going to Harvard, business School, Wharton and all these schools and I'm like holding mitts in Newark, you know, trying to stop leaks, making nothing right. But then, over time, you just start to realize everybody's got their own journey, their own path, and those same friends now recommend me to people that are struggling with their small business or just need a coach.
Keith Cowing: 18:53
I think it's a really important lesson there about motion versus action. I talk to entrepreneurs a lot about this, where we're frequently drawn to the things that we're comfortable doing and sometimes it's motion, it's activity. It looks like you're being productive, but planning and scrubbing your pipeline is motion. Talking to a customer is action. If you're a healthcare company and you're getting everything set up and started, okay, that's motion, you have to do it. But action is seeing your first patient. Action is having your first sales call, your first coaching meeting. Even if you don't call it coaching, just doing it and absolutely I can say in my own journey becoming a coach, just doing it was by far above and beyond the most confidence inducing aspect of it. That was, oh, now I really see where I have strengths, where I can work on things and where I was helpful, especially if you get feedback as you go.
Mike Steadman: 19:43
Yeah, man, you got to get the feedback loop going because, like I love that and I was actually taking a note there stay in motion, cause when you're pontificating, when you're self-actualizing, when you're thinking too much right, it can really mess you up, you know, versus just like taking action day by day, small, consistent action. You know, even going to the gym, right, like everybody comes back, they got their old new year resolution, et cetera. You know it's real easy to look at yourself in the mirror and be like man, I just let myself go. Versus just going to the gym, you know, getting those reps in three days a week. You know, getting those reps in three days a week, you know then you'll start to kind of you don't have to even think about it because you're actually doing the work.
Keith Cowing: 20:24
Let's dive into one thing that I'd love to hear from you on the leadership side. One question I've been asking a lot of my clients this year is what are you letting go of? Everybody wants to add something, everybody wants to commit and make new year's resolutions and then nobody finishes them because they have too many other things getting in the way, and a lot of times it's the pruning that's less sexy, but more important getting things out of the way so you can actually commit to the stuff that you want to accomplish on your side as a leader, as a business coach, everything that you're doing what are you letting go of in 2025?
Mike Steadman: 20:57
Old belief systems, belief systems that no longer fit me at this phase of my life. So, again, just to kind of continue taking off the armor, and this is kind of like listen. First of all, I don't have a PhD in like coaching or psychology, but this is just my take and I think there are people out there that support this. I think a lot of times on the psychologist side of the house, sometimes it can be rooted in the past, right, trying to adjust past trauma, et cetera, et cetera, whereas and there are therapists that do make that transition in the coaching Sometimes they're like forget the past. You know, it's like, the past is there, it is what it is. But let's start to build from here, you know, and let's use where we're at now as like a foundation and craft the identity and the behaviors and the things you aspire to be right.
Mike Steadman: 21:45
I grew up on a belief system that's really kind of getting challenged a lot, right, you know what's possible in terms of like and like I said, people tell you this stuff like you can be anything that you want to be, but again, until you experience it, until you touch it, right? Financially, you know you grow up going to the ATM with your mom, you know when she gets paid at midnight, and you're at the ATM, living paycheck to paycheck. That's not how I live now, you know, and being able to travel and all these different things. But at times I still feel like that kid in the south, you know, at the ATM with my mom. But I have to recognize that I'm in a different place. You know, and like uh, skill sets I picked up along the way, like I grew up thinking I wasn't very smart.
Mike Steadman: 22:31
You know again that I didn't go to one of these elite MBA programs. I didn't even take the GMAT because I didn't think I was smart enough, because just to go to the Naval Academy I had to take the SAT like six times. Somebody told me that I wasn't going to get in because I didn't have the grades. You know. So all those things. And yet I look up today, Naval Academy grad, got a master's from Rutgers in American Studies, got fellowships out the wazoo. You know and I'm not saying that to brag, but I'm just trying to say that is not how mentally I came into this world and I wasn't disciplined. And now let's say I am smart, I am disciplined. You know, I do know what's possible. Now let's build from here.
Keith Cowing: 23:19
And a lot of what I hear in there is you identify as being an underdog.
Mike Steadman: 23:22
Correct
Keith Cowing: 23:24
Dealing with that now that maybe you're not anymore on the outside, externally to the world, but inside. That's where you come from and you've used a lot of that in how you brand yourself and how you help your clients. I would love to hear you explain a little bit about your journey to very clearly articulating who you work with, how you help them.
Keith Cowing: 23:45
I think both coaches that are trying to identify who's my target audience and how do I really help them get to the next level in a way that they can understand because it's hard to write that first $6,000 check you don't really know what you're getting into but also people that aren't coaches - all entrepreneurs and product leaders and business leaders. We tend to be fuzzy because it's easy to not filter things out as opposed to being really, really crisp and you are an expert at being really crisp on your target audience and your offering. Walk us through that journey for you of how you identified who your exact best customer is and how you helped them.
Mike Steadman: 24:18
Yeah, it was a journey. It wasn't an overnight thing, right, and this whole thing with, like branding and marketing, I think in category first, brand second, so like, let's say, business coach. That's a category. People are going to have all their assumptions about it, but I say business coach for the underdogs and the misfits which I define as military veterans and anyone that's used to being one of one in the room. And what I start to notice in the entrepreneurial ecosystem it's all over the place. Right, you got the people from the Ivy League institutions getting a bazillion dollars in funding to start their ventures. Right, and they kind of all have a little bit of same flavor. And right, like in the military officer network, a lot of people go to a top 10, top 20 MBA program. Then they'll get out and they'll work in consulting or investment banking, et cetera.
Mike Steadman: 25:06
But if you're an academy grad or just an officer or military veteran in general, you do not go that pathway and you're like in your hometown trying to, you know, launch a cigar business. You know who do you go to? All these other people are talking about product, this product that you know, and you're just like I don't even know what I'm doing. I just need somebody I can trust and I realized that those people self-identify as an underdog and a misfit because they themselves internally don't feel like they fit in over here. You know, and for me it's like and again this may be my belief systems off here, right, like I just the blazers, the pocket squares, and you'll see some photos of me in pocket squares, so I can't talk, right. But again, I was in the gym for like 10 years, right? So most of the time when you see me, you would see me in an Ironbound boxing hoodie. Like 99.9% of my interviews were like in a boxing hoodie, et cetera, et cetera, because that's kind of who I was around, that's the environment I was in, et cetera.
Mike Steadman: 26:07
But if I internalize this idea that like to be a business person or be a business coach, you have to have like a thousand dollar suit on and a watch and all this other stuff, like that's not me. You know I don't try to sell envy. You know, don't be like me, because I'm not saying be like me, drive my car, do all those things. Like that's not what I'm attracted to. I'm attracted to kind of more, like just kind of realness and rawness and like let's just get each other better and again people just kind of start to self-identify. So really I was basically talking about myself and a lot of the kind of content and messaging. From my perspective, what I found out was it was resonating with a lot of military veterans, service academy grads that again self-identify.
Keith Cowing: 26:56
And you mentioned when you first became a coach at six months before you got your first client. Was that correlated with you learning how to articulate that really clearly and then you getting your first customers, or is that just it took a little bit of time for things to get warmed up? What did that look like?
Mike Steadman: 27:11
I think it was a combination of both. I think the more I was coaching, the more I started to recognize patterns across the board. And then you start to also recognize who's interested, you know, in working with you, who's interested in giving you a chance, right. And then I started looking up and more and more were military veterans. And maybe that's just because I was by network, right, that's just kind of where I plant the flag.
Mike Steadman: 27:34
But even within the kind of veteran network I just noticed that, like again, my messaging was really hitting with people and now you help other people that are trying to figure out their target audience, their brand, their approach and their offering. Walk us through that process a little bit. How do you help clients figure out what their strategy is and what their clarity is?
Mike Steadman: 27:58
Right, so I'm what you call a category designer. I got to train in the category design dojo with Eddie Yoon and Christopher Lockhead, one of my friends and mentor. They wrote a book called Play Bigger how pirates, dreamers and innovators create and dominate markets. And I read that book during the pandemic and I was like blown away by it, to the point that I tweeted Chris and told him how inspired I was. I was this entrepreneur in Newark and I think this would really help a lot more veterans and other people like me. He tweeted me back and said check your DM. He sent me his number and we spoke on the phone for like two hours and we've been attached at the hip like this and essentially and he probably gonna get on me for this, right, but there's the whole positioning and category right. And then you got a lot of startups that talk about oh, we're creating this new category over here.
Mike Steadman: 28:46
What I do is I try to help brands and founders because this is really CEO-level, where are you playing? And in the categories you got three options. Option number one you can go head to head with an established player. So this is out Google Google, you know? We saw what's happening with Deep Seek and Open AI. Those are head to head and typically in those situations you have a lot of funding, right? Sometimes you've been around a little bit longer. Think of MySpace, right, but they got knocked off by Facebook and Facebook, now Meta, social media, okay. So option number one is you go head-to-head with an established player. Option number two you niche down an existing category with proven and existing demand.
Mike Steadman: 29:35
So, for example, I use the example of Red Stripe okay, Budweiser was, arguably, back in the day, the king of beer. Okay, category king is 76% of market share. So that means, if you're not a category king, you're competing for that bottom 24% with everyone else. So the founders of Red Stripe are looking at the beer market and they're like yo, what's the kind of category can we really niche down around? Jamaican beer? You draw that line in the sand that distinguishes it from others, right? Because if it's Jamaican beer, from a brand perspective, what does that imply? Beaches, bikinis on the water, maybe a different flavor, maybe different, a little bit lighter, right? So think Red Stripe, okay. So category you have beer. We're going to niche down to Jamaican beer. Okay.
Mike Steadman: 30:21
Then option number three is you create a new category altogether, and so this is essentially non-alcoholic brewing. So that's the category right, and then the brand is Athletic Brewing. Now, remember what I said just because you're the first mover doesn't mean you're going to win the category. Back in the day, you know, one brand that came into play a lot was like O'Doul's or O'Tools for, like, non-alcoholic beer. You don't even hear about them no more. If you walk in any bar and you say, hey, do you have any non-alcoholic beer options, 99.9% of the time they're going to say Athletic Brewing, and to me that signals that athletic brewing is a category king there. The other thing that you got to do from a category perspective is you got to learn to read the room. Okay, so staying on alcohol tip five years ago, if you were to go out in New York city or any city across the country and you ask the bartender if they have any non-alcoholic options, maybe they'll make you something. They're like I could put something together, or whatever. Now, at least in New York City you go into a bar or restaurant, there's mocktails on the menu. So what does that signal? That that's a growing and emerging category.
Mike Steadman: 31:28
Okay, you think about retail right now.
Mike Steadman: 31:31
When I was in high school, most of the people that you saw work in retail at least fast food was like high schoolers, you know, or young people. You look at retail now you see a lot of older people, right, and then also people just don't look motivated in retail. You can tell retail's going through it. One day you go to your coffee shop and there's like three or four baristas back there. Then the next day you go there, there's one barista working behind the counter and there's like a line of 20 people out the door and he's feeling overwhelmed, right.
Mike Steadman: 32:01
So that lets me know, from a category perspective, that retail is a very, very hard industry right now. Same thing for newspapers, right, and the whole idea around this is that, like, Keith and I could be the best entrepreneurs in the world. But if it's 1930 and we open up a vegan barbecue restaurant, you know, in like Alabama or somewhere right, like, and the market's not there, good luck. Like again, you can have all the funding, you can have all the education, but if the market's not there, you're screwed. And so the whole thing about category, especially if you're underfunded and you're a bootstrapper, is you want to identify a wave and position yourself accordingly, and it takes a little bit of wordsmithing, a little strategic narrative, developing a good point of view, right, but it's possible.
Keith Cowing: 32:49
And if somebody wants to work with you, where can they find you? It sounds like you have amazing tactical advice. You've also got the inspiration of what I like to call return on luck, comes from the book Four Disciplines of Execution, where everybody has bad luck, everybody has good luck. The point is, when you're down, can you get back up and just stay standing? Can you manage through the bad luck? And then when you have good luck, are you ready and can you ride it and really just take it home? And you've clearly done both of those in your career and I have a really sharp way of helping entrepreneurs. So if somebody is a veteran entrepreneur, where can they find you? How can they get in touch?
Mike Steadman: 33:23
So I got two options for you. Option number one is just go to ironmikestedman. com. That's right, ironm ikes teadman. com, and just you know, reach out to me through there. Or you can go to wearethemisfitscom, which is the brand inside of the house. So you know, for people that might be a little bit confused, right? I spend 50% of my time doing business coaching and 50% of my time on the branding and the category side of the house and I have a team for the nonprofit, so I've been able to be in a more executive role there and less than like the actual day to day.
Keith Cowing: 33:55
Mike, it's been an absolute pleasure. I learn a ton every single time I talk to you. Thank you for joining me on Executives Unplugged.
Mike Steadman: 34:03
Man, it's a pleasure. And I do want to say this too we didn't even tell the audience how you and I connected.
Keith Cowing: 34:09
You want to give it the story?
Mike Steadman: 34:10
Yeah, so You know, I wrote a post on LinkedIn about how I'm just so confused by these MBA programs because, in my mind, like how can you teach business if you don't teach sales? You know, and who I have clients got MBAs, I mentor people with MBAs, et cetera, et cetera, and I was just thought it was crazy. Well, Keith commented and him and I went back and forth in the messaging like good comments, and then we were able to kind of link up in person and I think that just kind of goes back to what you said, whether it's return on luck, increase in serendipitous opportunities, but I think about my kind of platforms as more about nurturing a community and attracting the type of people that I'm looking to build with and grow with and learn from, et cetera. So it was real cool that you saw that comment and you and I were able to connect and hopefully we'll do some fun things together.
Keith Cowing: 34:58
sure we will, and I appreciate that we got connected that bias towards action of hey, let's just chat. And that comment resonated with me where, as somebody who has an MBA and teaches in an MBA program, I'm also very critical of a lot of the ways that academia has not evolved fast enough tech. I'm much trying to bring the real world of how do you build this stuff, how do you sell it, how do you go out there and make it happen, how do you have the reps, the action like you're talking about Go talk . to customers, not just drop a spreadsheet. And what I saw in you is a lot of that spirit and that's why we're bringing you to Cornell tech to talk Tech to some of the students and mentor and coaches.
Keith Cowing: 35:38
Real world experience applied to how do you build this company and how do you make it grow. Because teaching is still really important, but the flavor of it just really has to change because the world has changed and we've got to evolve how we both teach, but maybe even more than teaching, facilitate an environment in which people can learn. It's more like running a gym where you're just there to help them lift weights and you're providing a little bit of coaching and form corrections that they can't see themselves. But it's about doing the reps. It's not about imagining the reps.
Mike Steadman: 36:07
And getting the feedback loop started sooner rather than later. Like you said, when you talk to customers you just learn so much you know, and I definitely think it's shifting because back in the day, you know, early lean startup, it was all about like interviewing customers. That's great. But that's going to also be a false positive because people will say, oh yeah, this sounds like a great idea. Yeah, on-site boxing executives will print money for that man. I was looking for money under the table because why? That's a weak category. You know, you don't get me wrong, you can earn Okay, but like there was a ceiling, you know, just in terms of what people are willing to spend for group boxing. You know, even at the company level. But if you just listen to what people say, you know you would assume that they're right. But until you're out there taking those swings at the plate, then you really get the insight.
Keith Cowing: 36:58
This is incredibly helpful. I'm super happy to have you on here and we'll promote this episode to anybody that is a veteran or an entrepreneur or just running a business and dealing with pressure and crises how to do the self-talk, how to clarify what you're going after, how to have great return on luck, Mike, thank you so much.
Mike Steadman: 37:17
Thanks for having me, Keith.
Keith Cowing: 37:19
I find Mike to be an inspiration, both in terms of the self-talk and the perseverance and the bouncing back and the resilience. I was taking notes on tactics I can apply in my life and I know that applies with CEOs and leaders of all kinds. And also I really appreciate some of his advice on being very focused and specific and tailoring your offering in your market and dominating a niche. You can find more of Mike at ironmikestedman. com and, as for me, you can sign up for my email newsletter at kc. coach for free insights and leadership tips right in your inbox. If you enjoyed this episode, please give it a five-star review on your favorite platform. It helps the podcast and it helps other people find it and benefit from it as well.
