#89 - Todd Simmons - Courageous Leadership & Authentic Living

Todd Simmons is the Founder and Chief Vision Officer of Courageous Leadership Alliance. 

As a seasoned educator, executive coach, organizational culture influencer, international keynote speaker and business leader, Todd strives to build a coalition of change agents sharing a common aim for building a society of courageous leaders. 

Todd has worked with global institutions and businesses such as NASA, U.S Air Force, U.S Space Force, Professional Golf Association (PGA), Amazon, and many others.

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Martin opens with a shoutout to loyal listeners and a Nick Saban quote ("If you want to make everyone happy, don't be a leader. Sell ice cream.") that resonates deeply with Todd, who is a die-hard Saban fan. That sets the tone for a candid conversation about leadership, resilience, and authenticity.

Todd shares formative childhood experiences, particularly around his fear of snakes, and connects them to broader lessons about how fear and formative moments shape us as adults. He unpacks his perspective on vulnerability, consistency, and the importance of living fully and intentionally, describing how his own life changed as he confronted loss and committed to making the most of every day.

The discussion weaves through Todd’s varied career—from his time in the Air Force to building businesses—highlighting how relationships, mentorship, and personal growth are vital, regardless of age or experience. He talks about building credibility through consistent effort, the nuanced reality of stepping outside comfort zones, and the misconceptions about what it means to be “busy” versus living a life full of purpose.

Todd’s philosophy shines through as he speaks about managing personal energy, saying yes to opportunities that fit his values, and being deliberate about filling his calendar with “life” instead of just “things.” He underscores the importance of knowing and playing to your strengths, and the value of “doing the work” internally to protect your peace while staying ambitious.

There are heartfelt moments where both Todd and Martin reflect on loss, legacy, and the drive to use their time purposefully, plus lighter exchanges about golf, friendships, and even buddy-cop movie pitches.

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Conversation:

Intro 00:00 Todd Simmons Hey, Martin. Thank you. Hey, I know you're on Skillbridge, but you got a job as my national announcer. How about that? I'm saying it on your podcast next time we are in the same place. I'm going to kick the emcee off the mic on the podium and I think I need Martin Foster to come up here and interview. Usually I don't like hearing all that stuff about myself, but I appreciate you being concise and actually, it was pretty cool. I never know what someone's going to say, so I appreciate it. 

Nick Saban Quote

03:15 Todd Simmons You must have did a little research on me. As soon as you were saying that quote, and I was looking up to the right in my office here. I'm in my home office today. And one of the most prized possessions I have is a Nick Saban signed helmet for the University of Alabama with his personal business card on it with his cell phone number. I don't know how they got that, but that was my retirement gift from Air University that they knew how big of an Alabama fan I am. I'm a larger Nick Saban fan than I am an Alabama fan. It's Nick Saban, then Alabama. So, yeah, I think that quote is spot on. 

I say that and we'll get in a lot of those conversations. If you want to be a leader, you want to be an entrepreneur, you want to do anything that's going to take scrutiny or people or there's not a real defined line to get to point A, B, C, D, and F. You might as well go sell ice cream because it's going to be much easier.  I love that quote from Nick Saban, and it was something that probably got me in trouble a lot in uniform because a lot of my time in the last part of my career in the Air Force was in leadership positions. I was like, not everyone's a leader. Not everyone in the leadership position is actually good at being a leader either, so. But it's the truth. 

It's a skill set that needs to be sharpened every day. So thank you, Martin. Thank you for that.

How fear of snakes shaped adulthood

04:19 Todd Simmons That's a great question. So you must reading a lot. I would tell you fear of snakes. I don't know how old I was. I was a young kid. I think I wrote about you probably read my book. But I was a young kid and I was running in the dark between my great grandmother's house and someone else's house. I'm from the south, I'm from South Carolina, rural area. We're running in this huge patch of land and something brushed my leg and it like broke skin.

And it was dark, pitch black, dark at night in the south, running through knee high grass and it looked like, and I just knew it was a snake. 

So I went in the house screaming all of this stuff and was bleeding and it had looked like two little strike marks, kind of thing that looked like a snake bite, but it was a stick. So I will tell you from there on, I just get this fear. I don't know if it was because I was so young, but that was a snake bite story.

But fear in itself, that's an evolving thing and  each person is different. For me, I don't fear much and I don't want to, I don't want that to sound arrogant or cocky. And I'm very comfortable that every day is a new day to be a better version of yourself or to get something done or to be a better friend, father, husband, whatever it is. 

So I don't fear the end of anything. I fear not being intentional to begin something. That's my fear. It's like you mentioned, it's not that I do so many things. I really don't want anything left that I don't want at the end of the day. I know time is not something that we have a lot of, It's just not, it's not infinite. I'm almost 50.

The people like, oh, that's not old. But it's not actually young either. I mean I've lived most of my life, to be honest with you. I mean even if I live another 50 years, I'll be 100 and I'm probably not going to be walking around as limber as I am at 100 years old. So I think my biggest fear is not being who, not being true to myself, not being comfortable doing the things that would scare a lot of people. Not going out there and being able to be comfortable in failure. Not being comfortable and doing something that may not work in public. 

Going out there striving to be better at something that you may discover that, for instance, for me, I love playing golf. I love it. I love being outside. But everyone has a different reason why they play golf. I love being outside. I love the smell of nature. I love the way they manicure golf courses and walk up and down golf courses. I love the camaraderie of the people I'm playing with. 

I love everything about it. But I'm not that good at golf. But it doesn't deter me from coming back over and over and over and going on four or five golf trips a year. And it doesn't make me ever feel self conscious that I might be. I've come in last place, Martin. I have come in last place in a golf tournament out of 70 people. 

I've come in last place in a golf tournament that I had paid thousands of dollars to go to. Not once, not twice, but probably like three times. And you know what?  I learned something about myself at the end is like I never actually cared about being in last. It never even like bothered me. 

So what I fear is, is not continuing to live every day and just be thankful every day to have the opportunity to do things that you do every day. If I fear anything is I fear that I may be taking the ability for me to be taken away at some point. My quality of life or my health. That's the only thing I fear is that I won't be able to get up every day and do the things that I so much enjoy on such a simplistic way. 

What would surprise his younger self about his current self

10:52 Todd Simmons It depends on what you mean by younger self. If you mean younger self pre 18, I would tell you pre 18 me would be totally in utter shocked shock of that I am even remotely anywhere . I would say 25 younger self of me, not necessarily in shock, but a little surprise. I would think 35 year old me, I'm almost 50. 35 year old me would be like, you did it, you did it. Because I think that's at the point in my life, probably around 35 is where I kind of saw that, you know what, you might not have all the abilities that everyone else and that's okay. You've already proven at this point that you're not the fastest runner, but you can get to the finish line. 

I've already proven it myself. So what are the dreams that you really have that you can materialize for yourself? I think around 35 is where I realized, okay, you can, you've already proven that it's going to be harder, it's not going to be easy. You have some limitations, but that doesn't mean that you're out of the game. You just gotta now play the game on your strengths. So I would say that, you know, pre 18 me would be utterly shocked. 25 me would be like, oh man. Like, oh, like who's that guy? And I think 35 year old me would be, feel a sense of accomplishment, would say, man, you, you set out for a plan, you work, you did the work, you took the failures, you took the punches, you took the lumps and you just, you did it your way. I think that's what would be the kind of that, you know, kind of three part answer to that. 

Bush Center Veteran Leadership Program

15:30 Todd Simmons It was 2024. That was great. I have always been a lifelong learner and I'll just be honest, something I consistently is talked about probably a lot less now because honestly I've been out six years of the military. I used to be a  a little bit probably too preachy about it. In those days that I talked about those hard days becoming less sometimes that's your personal journey that you have to go through, even though I, I know you're transitioning, I'll give people all advice that they want. But sometimes I know a lot of the best lessons I've learned is through trusting people and my circle. But I would tell you a part of what I've always been probably because I was an adjunct professor since I was a tech sergeant E6 in the Air Force since 2005 by the way, 20 years now. 

So I've always had these multiple circles of people I hung out with. I can grow from all of them. The Bush Institute was just another example of how you have to have networks beyond your comfort zone. I thought it was a great program. What I took away from that program is genuine relationships. I think probably more than 10 or 12 of the people that I went to that program with I talked to on a very frequent basis. But if you go into those opportunities, to be honest with you, looking for transactional things or any one of these opportunities looking for transactional things, then you're not going to take away what really matters in those situations. So for me, I thought it was awesome to be around small group of people who all for the most part had your go getter spirit, was all working on things that they were very passionate about. 

So it was good to be in that environment for five months and a lot of things have come out of that. I mean you'll, I work like I say, three or four people I actually are in a business relationship with from there and it just, it wasn't nothing that was transactional, which is something that materialized with the like minded people that you, that you get a chance to operate with. But yeah, I thought it was a great opportunity. If I had an hour on your podcast to just talk about so many different opportunities, the Bush, I think anything that IVMF offers over at Syracuse, all those veteran programs, there's so many things that are available today that weren't available 10 years ago. If you're not taking advantage to grow your circle in uniform and out of uniform, or if you're not even military affiliated, whatever, then you're missing out on opportunity to grow yourself. 

Willingness to take risks and step out of comfort zones

18:34 Todd Simmons I changed my tune on that, Martin, to be honest with you, because I can sit here and I see these posts and these graphics on social media that be like, jump out of your comfort zone. Have this mindset. And honestly, that's not for everyone. And I think on the surface, everyone should jump out of a little bit of their comfort zone to grow as a human being. Absolutely. But some people like the structure and systems and that's okay. I'm actually a person who hates structure and systems. I don't know how I survived in the military for 25 years. I'm just going to be honest with you. My brain doesn't really work that way. 

I thrive in opportunities that change every day. I love being involved in organizations and processes that are not going to be the same. How do you figure this puzzle out? How do you be creative? How do you not have, you have left and right boundaries or how can you stretch those left and right boundaries out? I believe in those kind of things. Personally, I think those are very basic characteristics that you have to start off with for successful entrepreneurship because there is no structure...every day you have to figure out, figure out a new problem, a new challenge, a new answer to a challenge, a new answer to a problem. So, yeah, I think a growth mindset is absolutely important for everyone, but I think the speed of growth for each individual is different. 

Controlled Chaos

21:20 Todd Simmons Actually my name in my house is Chaos. That's my nickname. So just to throw that out there, that is literally my nickname is Chaos. And to other people's outside view, it may look chaotic and busy because two terms I get thrown at me inside of my circle of friends, they say I'm chaotic. Outside that, people who don't know me that well, they say I'm busy. 

But I think it's a nice way to go. Man, your life looks like chaos. But I would tell you, Martin, my calendar is full of life. My calendar probably has more leisure things on it than work things.

I know people who are busy who haven't been on a personal vacation in two years. I know people who are just as busy or can probably quantify their business similar to mine. 

Who doesn't go on a walk every morning for three miles or doesn't go on a couple of weekend retreats a year or four vacations. I'm not saying that in any kind of arrogant brag mode, but I, I said something when recently on K Wright's podcast. My calendar is full of life, not things. And you can get in this mode where your calendar is full of things and not life because there is an infinite amount of busy. But in the military I never subscribed to staying after work after 5 o' clock unless there was a mission driven reason to stay at work past 5 o'. clock. I didn't do it as a sport to say I was at work for 14 hours for no reason. 

If I'm there because the mission demands it to be, absolutely I'm there till the end of time. But if the mission didn't demand me to be there after five, I went home to go do things that required my life to function. So that's the way I live my life then and that's the way I live my life probably 5x now that the barriers are kind of off. ou mentioned CLA. 

I own CLA. I'm actually the co owner of Courageous Core Federal, which is a joint venture that I'm 51 percent in. We're actually opening up a new joint venture between three partners that we can't announce yet. I'm also the chairman of the board of the Air Force Enlisted Village in Fort Walton Beach, Florida. I'm also on two other boards. I also do do all of these other things. Right. I'm also a dad. 

I'm also a husband. I'm also a person who believes deep in my own personal health and my own personal resilience journey. Now how do you put all of that into one person's life? You have to be deliberate and the back to the word consistent on my calendar. There's boulders on my calendar and why I call them boulders because you're not going to be able to move that. No money, no opportunity, no amount of oh, I can go do this to be more of this. I'm not going to compromise that. I'm going to go to Iceland. We're going to Iceland in a few weeks. 

I'm going to go golfing. I'm going to go to Africa for 20 days for my 50th birthday. I don't care what happens in those 20 days that I'm not here. There's not a lot of time we have. And from 18 to 43 years old, I was in the military, and I didn't have a lot of resources nor time to do some of the things that I've been afforded to do now in the last six years. So I'm not going to squander that just to say I've achieved something. 

So if I just wanted to be busy and do all the things that look good on the busy side, yeah, I can do that all day. But that's not the life that I want to lead. Everyone has a choice. And you can make the choice to be busy and chase the titles and the. In the pizzazz of what people, what you want people to think from you, from the outside looking in, or you can do the things from the inside of you going out and what people think of it is up. It doesn't matter. You're doing it for you.

Advising high-achievers on protecting personal peace

31:10 Todd Simmons First of all, you gotta do the work within yourself. And this is a hard thing. I took a podcast break. You're the first podcast I've been on in quite some time, except K Wright and doing ours.

You're bringing up a lot of things I probably want to talk about for the last year and a half. How do I advise people now, man?  I don't give a lot of advice. And why I say that is because I don't know what's for you. The advice I can give you is do your own work. Who you want to be, what do you want to be, what kind of life you want to feel every morning when you wake up. 

That's something you have to discover and write down. Do a lot of journaling. You have to get some kind of plan and focus on what do you want this to be for yourself. What it looks like for me may not be what it looks like for you. And that's the first thing is I don't. Probably it looks like I walk around with blinders on every day because I really don't really care what's going on in the outside world more than I care what's going on internally. To me, a couple of hard, fast rules I have. First rule is energy management. 

I manage my energy. For me to be chaotic, like I told you, and to be all over the place. The one thing that's super scheduled is my energy. And when I say scheduled, there's uncompromising things. One, I will never involve myself in negative energy on no surface. So even to the point, Martin, I'm sharing this with you, and it might sound very fanatical. I have a lot of people that I'm probably friends with on social media, but I don't see probably 60 to 70% of the people. And I might offend some people.

Take for instance, Facebook. I don't know how many Facebook friends I got. Say I got 4,000 Facebook friends friends. I probably don't really see 70% of those people's posts. I unfollow. I. |

I don't unfriend, but I unfollow. And let me tell you why. If Martin, if you decide to post what I call and I don't want to offend nobody, woe is me post all the time. Like the world is falling down all the time. And for example, people hating on me and all of those type of posts, I don't have an issue with your post. I have an issue with what that post does to me in my brain. Because what you put inside of your brain, just like what you put inside of your body from food, it has an effect on you.

So if you're looking at things that are not positive, then it can really chip away from the positivity of how you see things externally. So for me, I just choose not to consume that. Just my choice. I choose not to consume it. And I choose not to be someone who put others out. You'll never see one of those posts for me. And that doesn't make me better, doesn't make me better than anybody. 

It doesn't make me better at all. I want to repeat that three times. I am not better because it's just what I choose to put out into the world. I want to be in a place where my energy can come off as positive as possible. So that's one thing. My energy is managed my day, I walk every day. I manage who I want around me. If you're a person who is not in a good place, I'm going to help you as much as I can get into a good place. 

You have to just manage the energy that you put around you. If someone is not really wanting to support you. So what, Why would you post about that or why would you have energy toward it? That's. I'm not saying people who do that are wrong. That's just the way I look at it. There are billions of people in the world. 

I meet people every day. Some of them are great human beings. Some of them are people I can have a drink with and some of them are people I probably never want to talk to again. It's okay. And I'm sure there's people in the world who feel that about me, who meet me and I, I don't feel like it's a knock on me. I feel like if, if the world was meant to be where a  billion people be friends with each other, then that would look strange. It's not the way. 

So how do I do that? I manage my energy, I manage, I manage a lot about what I want to do in my 60 year old self like you brought up earlier. And that drives me toward a lot, that drives me toward a lot of things. Long answer to your question, but I just really try to manage my life at this point. I'm an introvert, to be honest with you. And the one thing that I really enjoy about this side of my life being an introvert is that I can be an introvert. And I will give you a little secret. The best day that I can put on a Monday through Friday is a day where I sit in my home office when I don't go into my actual office and no one's around and I can just like put on Netflix and I can have my laptop and I can be doing work at the same time and. And there's no one around, there's no phone ringing, there's nobody texting me. 

That's the best day. The best day for me is not being around a lot of people. I have days where I need social interaction, but those days probably are less than the days that I just like walking three miles around my neighborhood thinking about being introspective about life and what I want to do, how I want to engage my two daughters better, how I want to take care of things better. So that's, that's kind of a good day. 

Unfair expectations people place on him

38:04 Todd Simmons I'll answer that in two parts as  someone who came from  my beginning of my career at 18 years old, I didn't feel like I had anybody to talk to. And that led towards suicidal ideation and attempt.  I'm not a chat GPT bot, which means that, if you IM me, give me some grace every now and again, 24 hours. But I'm the person who will, I am the person who will IM you back if someone texts me, which has happened years ago when I had an individual who saw me at a conference years later text me in the middle of the night over, over Facebook, who was literally at the stage of committing suicide. So I take the fact that if someone's reaching out to me any medium text DM on Linkedin, I'm going to respond. It's going to be me. 

So I don't want to take this introverted, like energy management conversation into people. I want to be very clear about that. You can reach out to me anytime. I'll pick up a phone from anybody, any time of the night, any day. It's on my business card, it's my personal cell phone number and I keep count of how many boxes I've used. I've given out my personal card with my personal cell phone number out to over 4,000 people since I retired. That's why sometimes if you text me and I text you right back and go, who is this? It's not offensive. 

It's because there is literally thousands of people who have my personal cell phone number. And every week I get at least a couple of texts, random texts, who? I just got to go, hey, hey. Who exactly is this? Before I respond and where did we meet? And that's okay. So I'm just explaining that the second piece of unfair expectations. I would say this clearly to the mic. Unfair expectations. I don't have expectations on anyone to give me anything I don't earn. I don't have that expectation. 

I've never had that expectation since day one of me being an adult. I would say have. What I believe sometimes people's unfair expectations is they see the social media, which is very regulated. Nothing is a 100% true on social media. It's what people want you to see. I am busy. I am doing a lot. I am up 5 o' clock every morning. 

I did spend the first 18 months of my life out of the military up till 2, 3 in the morning trying to build a business, trying to get people to have meetings with me.  I'm not going to shy away and say I didn't work hard to get at least to the point where I'm at now. The unfair expectations back to the time in the calendar is that I should have that time to do that for you without you putting the same level of work effort in. And that's unfair. 

Potential Campaign Slogan

52:54 Todd Simmons Oh, my goodness. If K Wright was running for president and I had to come up with a campaign slogan, what would it be? Oh, man. Man, that's a tough one. Off the top of my head, I don't know why this came out the top of my head, into the future. I don't know why that came off the top of my head, but that's the first thing that came to my mind. Into the future or. Or we're behind, we must catch up. That's another one that came to us. Oh, man. I don't know, man. I would have to think about that, but I just. It's something futuristic. It would have to be something about how we are stepping into the future. If I had to think about. With his campaign, because all of his ideas walking in there would be, what we have already done is good, but it can't continue. 

Investing ONE MILLION Dollars into one person in 2026

57:36 Todd Simmons If I was to invest, oh man, this is just so timely. If I was to invest $1 million into a person, I would invest into Haley Marie McClain Hill. 

If I had in 2026, I would invest a million dollars into her. Because everything I have mentioned, I just talked to her yesterday. She's the most energetic, consistent, coachable, all the things that you would want in someone to mentor and tell them to take this and go, go forth and create and conquer. She fits every one of those consistent, energetic, humble, thoughtful, intelligent business acumen which is super important creative idea. I would give her a million dollars. | 

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Todd's Resources:

Website: https://www.courageouslead.com/about 

LinkedIn: https://www.linkedin.com/in/todd-simmons-mba-fbina-7971a5156/ 

2 Knights and A Mic Podcast: https://www.youtube.com/watch?v=6fzYgHNo65Q&list=PLeVZGYDqk742qmx3wlwXFJROkQb1n3OUE

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Mentioned:

Nick Saban

Kaleth Wright

Edgar Jones

Tony Covington

Haley Marie McClain Hill

Mary Polanco

Dr. Benjamin Hardy

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Key Takeaways:

The essential nature of intentional living and consistency, especially for leaders.

Building relationships and networks not for transactional gain, but for genuine connection.

How early experiences shape adult fears, motivations, and growth.

The importance of energy management over just time management.

Advice for high achievers on maintaining personal peace while pursuing big goals.

The value of knowing your unique strengths and bringing them to everything you do.

Being open to change, stepping outside comfort zones in ways that fit your personality.

Living with gratitude and urgency by recognizing life’s brevity and unpredictability.

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Quote:

- “If you want to make everyone happy, don’t be a leader. Sell ice cream.”
 - Nick Saban