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Life and Leadership Lessons I Learned In The Military: “Embrace the loneliness.” with Mike Steadman and Chaya Weiner

Embrace the loneliness. I didn’t realize when I first went to Afghanistan, just how lonely life would be as a second lieutenant. As an Officer, you have to maintain a professional relationship with your enlisted Marines. At my patrol base, I was the only officer in a platoon of 50. I struggled with it initially […]


Embrace the loneliness. I didn’t realize when I first went to Afghanistan, just how lonely life would be as a second lieutenant. As an Officer, you have to maintain a professional relationship with your enlisted Marines. At my patrol base, I was the only officer in a platoon of 50. I struggled with it initially and it affected a lot of my leadership decisions. Making the tough decisions in the face of constant scrutiny is a hard thing to teach. But because of my experience dealing with it in Afghanistan and the Marine overall, I learned to own it as an entrepreneur. As a leader, you have to learn to find company with yourself. You have to embrace the looks of disdain and understand not everyone’s meant to be a leader. Some people are just comfortable criticizing others without ever putting themselves in the hot seat. Not me. I own it.

As a part of my series about “Life and Leadership Lessons Learned In The Military”, I had the pleasure of interviewing Mike Steadman, Founder of IRONBOUND Boxing and Advisor to the WeWork Veterans in Residence program, powered by Bunker Labs. Mike is a graduate of the United States Naval Academy and Marine Officer with Deployments to Afghanistan in 2012 and Japan/Philippines in 2014. IRONBOUND Boxing is a veteran-owned company founded in 2016 that specializes in teaching boxing. We connect companies, organizations, and communities in the NYC Metro Area with on-site boxing instructors. Committed to social impact, we dedicate a percentage of all our proceeds to support free boxing programs for inner-city youth. IRONBOUND Boxing started as a free boxing gym located in Newark, NJ, has emerged as a full-blown social enterprise, leading the charge in the corporate fitness and social impact arena. We believe profits and purpose are not mutually exclusive. We use sound business practices to generate income through corporate partnerships to and support causes that matter and communities in need. WeWork Veterans in Residence powered by Bunker Labs is a national initiative providing space, services, business mentorship, and community to help veteran and military family member entrepreneurs find their tribe and create their life’s work. You can learn more and apply at we.co/veterans.


Thank you so much for doing this with us! Can you tell us a bit about your childhood “backstory”?

I’m originally from College Station, TX. I grew up with my mom and raised in a single parent home. Until this day, I have yet to meet my father. My mom was a special education administrator. She really inspired me to chase my dreams and go to college. I wouldn’t be where I am today without her.

And what are you doing today? Can you share a story that exemplifies the unique work that you are doing?

Today, I’m the founder and CEO of IRONBOUND Boxing, a social enterprise based in Newark, NJ that funds free boxing programs for youth and young adults. In 2016, I launched The IRONBOUND Boxing Academy along with my partners Gary Bloore and Keith Colon. We train over 20 kids, six days a week and run a competitive amateur boxing team. In order to fund the program, I created a three-headed monster; a nonprofit, a for-profit, and educational platform called “Lift As We Climb.” Essentially, I hustle all day everyday, working on various business strategies to generate income. Each day I wake up focusing on raising funds through our nonprofit, generating revenue by teaching to corporations as a form of employee wellness, and generating educational content through “Lift As We Climb.” It might sound crazy but it all works itself out.

A recent example of a day in my life is last week, I was working with one of my corporate boxing trainers, making sure he was all set for his upcoming event, then I headed into NYC to film a podcast with Mission.org, once that was done, I sprinted across town to host an event for the WeWork Veterans in Residence program and in the evening I attended a beer tasting for one of our veteran entrepreneurs from the program, Talea Beer Co.

Can you tell us a bit about your military background?

I spent my first five years in a collegiate environment, first at the Naval Academy Prep School followed by the United States Naval Academy. I actually picked up boxing for the first time while at the Academy. Despite my lack of experience, I went on to win three National Championships as a light-heavyweight and two “Most Valuable Boxer” awards. Upon graduation, I accepted a commission as a Second Lieutenant in the United States Marine Corps. I became an Infantry Officer then deployed to Afghanistan in 2012 and Japan/Philippines in 2014, both with 1st Battalion 8th Marines based out of Camp Lejeune in North Carolina.

Can you share the most interesting story that you experienced during your military career? What “take away” did you learn from that story?

My time in the military really taught me about leadership. I learned that a leader needs to carry himself two steps ahead of where he currently stands in order to be successful. In the Marine Corps, it doesn’t matter if you’re a lieutenant, you should carry yourself like a Captain. You need to show up prepared for the job you want, not the job you have. I’ve seen the effects of this first hand. When your moment to transition into the role you want comes around, no one will second guess you. The same principle applies to my life as an entrepreneur. When you’re in the early stages of building your company, you need to treat every decision as though it’s one for a thriving enterprise because that’s where you’re headed. Don’t be stuck in small-minded thoughts. You are your own best advocate. No one can see your vision the way you do, you have to make them believe in you. At IRONBOUND Boxing, we produce our own content, we are building out our back-end business processes, and building relationships with established companies like WeWork and others. As we continue to grow into a million-dollar brand, we are paving the way to our success by walking the walk and talking the talk of our more established peers.

I’m interested in fleshing out what a hero is. Did you experience or hear about a story of heroism, during your military experience? Can you share that story with us? Feel free to be as elaborate as you’d like.

Being the military, I was fortunate enough to be surrounded by heroes. You walk in the footsteps of giants. It’s hard for me to pinpoint just one, because I saw heroic actions everyday.

While I served in Afghanistan, Improvised Explosive Devices (IEDs) were a real threat. Every time we left our bases, we went out into an invisible mindfield, both in vehicles and on foot. There was a real chance if you didn’t lose your life, that you could lose a limb. In my eyes, one of the unsung heroes is the Marine on point — they are putting themselves in harms way, every single time. Many Marine’s don’t get the credit for their heroic actions, because it’s just part of the job, but they are the ones leading the way and creating a safe path for the men and women who follow them in the battlefield.

On one mounted operation my platoon hit two IEDs enroute to an objective. Thankfully no one was injured but we were shaken up. We carried on and executed our mission through bad weather conditions. When we were returning to base, visibility was limited, the wind was blowing at 100 mph and the only way out was the way we had come in. A squad leader of ours took point, knowing how dire the situation was, and led us through the night. I spent the entire drive worried for his safety and feeling grateful for his leadership. We arrived safe. People often think of the men on the field, dragging a wounded teammate arway from a firefight, but it’s these small heroic actions that go unnoticed and make a world of difference.

Based on that story, how would you define what a “hero” is? Can you explain?

I think a hero who acts selflessly, thinking about the wellbeing of others before they think about themselves.

Does a person need to be facing a life and death situation to do something heroic or to be called a hero?

Definitely not! My mom is my biggest hero. She sacrificed so much to ensure I could follow my dreams. No matter how dire our financial situations were, she remained strong for my sister and I. The passion and empathy I have for helping others comes from my mom. She instilled it in me at an early age.

Based on your military experience, can you share with our readers 5 Leadership or Life Lessons that you learned from your experience”? (Please share a story or example for each.)

I’d love to.

1) Know Yourself and Seek Self-Improvement. This is one of the Marine Corps Leadership principles. It may sound cliche but the principle holds true both in the military and as an entrepreneur. We have to constantly learn, adapt and grow. You have to want something so badly that you seek out every opportunity to make it happen for yourself, and enlist the help of others along the way. I learned this early on in the military and honed this skill as an entrepreneur. I’m constantly reading, attending workshops, meeting with other business leaders and attending events in the WeWork space, and listening to podcasts to make me better. I always want to improve.

2) Be Authentic. Authenticity is extremely important and it shines through whether you’re talking with a friend, or doing a business deal. It’s something that took me a while to learn. When I started in the military, I thought I had to be someone else’s version of what an officer should be, but once I got my second platoon and a bit more experience, I felt comfortable being myself, and that’s when I really started to thrive. This authenticity has followed me into founding a business, and my work with WeWork’s Veterans in Residence program. IRONBOUND Boxing is as authentic to me as breathing, I love the sport, I love sharing it with the world and I love impacting the lives of young women and men finding their place in the world. WIth WeWork it’s the same, I get to help veterans just starting their business ventures grow and thrive and there’s nothing more authentic to my core than that.

3) Embrace the loneliness. I didn’t realize when I first went to Afghanistan, just how lonely life would be as a second lieutenant. As an Officer, you have to maintain a professional relationship with your enlisted Marines. At my patrol base, I was the only officer in a platoon of 50. I struggled with it initially and it affected a lot of my leadership decisions. Making the tough decisions in the face of constant scrutiny is a hard thing to teach. But because of my experience dealing with it in Afghanistan and the Marine overall, I learned to own it as an entrepreneur. As a leader, you have to learn to find company with yourself. You have to embrace the looks of disdain and understand not everyone’s meant to be a leader. Some people are just comfortable criticizing others without ever putting themselves in the hot seat. Not me. I own it.

4) Take failure on the chin and keep moving. Leadership is not as sexy as people make it out to be. The highs are high and the lows are lows, and as leader, you’re responsible for both. This is one of the core things we teach entrepreneurs coming through the Veterans in Residence program. It’s hard making a leadership decision after you’ve failed and your confidence is shot. But life is a marathon not a sprint, and we’re all playing the long game. So take the loss on the chin and keep pushing.

5) Lift As We Climb. I believe this really embodies my leadership philosophy. I try to lift up those around me as much as possible. When I struggled in my role in the military, it was my friends and tribe that helped me navigate situations and grow as an officer. When you’re hustling, often it’s hard enough just worrying about yourself, let alone the people around you, but I’m here to tell you it’s worth it. Throughout my time in the military, founding IRONBOUND boxing and working with veteran entrepreneurs at WeWork, I can unequivocally say, there’s nothing more rewarding than helping the people around you thrive. It gets your head in the right space, and helps you become a person people want to do business with. I can’t put a dollar amount on how much helping others has come back around and helped me along the way. I want to build a company and a world that lifts up everyone, not just a select few.

Do you think your experience in the military helped prepare you for business? Can you explain?

My military experience taught me grit and leadership. I spent 5 years in the hot seat as an Infantry Officer, under constant pressure from my peers and subordinates. Being an Infantry Officer taught me how to thrive under the most difficult of circumstances. A lot of people have never been in a leadership position, so it’s foreign to them, not to my peers and I.

As you know, some people are scarred for life by their experience in the military. Did you struggle after your deployment was over? What have you done to adjust and thrive in civilian life that others may want to emulate?

I’m not going to lie, I struggled after my first deployment in the military. Not in the way you might think, I didn’t have a traumatic experience that stuck with me, but it was a struggle to fit into a world of leaders and I experienced a deep stress over not performing at the highest level. I think the best resource, no matter what post-military issue you might be struggling with, is surrounding yourself with true friends and mentors. Instead of trying to solve everything alone, I had to be open and honest about my struggles with my friends. Through transparency and trust I let my friends help me back onto my feet. I’ve taken this learning into my civilian life too. I never pretend like I have all the answers, I’m constantly seeking advice from others and being transparent about where I need help. It’s allowed me to make great strides in my life and I recommend others doing something similar.

Are you working on any exciting new projects now? How do you think that will help people?

I am! I’m excited to have recently launched my own educational platform called “Lift As We Climb,” that’s focused on helping people of color start and grow their own businesses.

As a veteran, I have unique access to services and support from places like free workspace and networking opportunities through WeWork’s Veterans in Residence program and resources from VSOs like Bunker Labs. However, non-veteran people of color, particularly in inner-cities like Newark, are working twice as hard with half the support. For example: in communities of color, a “friends and family” round of early-stage capital is virtually nonexistent. This means many entrepreneurs don’t have money when they’re working to find product/market fit, so a lot of these ventures never get traction.

My goal is to ensure founders of color don’t have to face these challenges completely alone. Through Lift As We Climb, I will interview people of all backgrounds, who have launched successful businesses and subject matter experts across the board. This will be a living resource that will grow over time. Outside of the educational component we are also providing monetary support for up and coming businesses. We recently made a microloan into coffee brand, Dope Coffee, in Atlanta, GA. We’re really excited to support and work with them and other founders of color as they start their journey.

What advice would you give to other leaders to help their team to thrive?

Be confident and own your leadership role. Some people choose to be leaders and others choose not to. If you’re in a leadership position, own it.

What advice would you give to other leaders about the best way to manage a large team?

Learn how to delegate. Sometimes as a leader, it’s hard to let go of control and utilize your team in a meaningful way, but it is essential to growing your team and your business. You can’t do it all on your own. By giving responsibility to your team you’re helping them grow and learn, and you’re freeing yourself up to tackle the most important tasks in a day.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Right now I’m feeling very grateful for Brett D’Alessandro, founder of Backpacks For Life, and a fellow veteran who I met through WeWork’s Veterans in Residence program. Recently we each entered our businesses into a competition for funding, alongside several other veterans from the program. The competition put on by Street Shares relied on online votes to determine which veteran-owned businesses would have a chance to pitch their ideas live and win $25,000. As we approached the final 48 hours, IRONBOUND Boxing dropped to 4th place. Brett’s company was leading in first and rather than let me struggle, he lifted me up, giving me his strategy for securing online votes. Ultimately we won the competition and Brett’s business took second place. If it weren’t for Brett, I wouldn’t have even gotten a chance to pitch my business, but he was committed to getting us both to the finals and I will always be grateful to him for that.

How have you used your success to bring goodness to the world?

My team and I have managed to build a boxing gym in Newark, NJ one of America’s toughest and poorest cities. It’s a blessing being able to support the kids in that neighborhood.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I want to challenge every person who reads this to invest a founder of color. It’s so hard for people of color to raise capital, I want to bring awareness to this problem. We live in a beautiful, diverse world, and the more people from different backgrounds bringing their ideas and products to the mainstream, the more our world will become a place for everyone.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“If you’re going to try, go all the way, otherwise don’t even start”- Charles Bukowski, Roll the Dice.

There’s been times I felt like giving up or taking the easy way out, but this quote keeps me motivated. You can’t do anything great if you don’t put great energy into it.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

I’d love an opportunity to meet with Jean Case from the Case Foundation. I recently had an opportunity to read her book “Be Fearless: 5 Principles for a Life of Breakthroughs and Purpose.” As a social entrepreneur, I found her book really inspiring. The Case Foundation invests in people with ideas to change the world. I believe IRONBOUND Boxing has the ability to bring much needed support to our inner-cities, particularly for young men and women of color. I believe IRONBOUND Boxing is a scalable model and would love to work with her to bring it to inner-cities across the country.

Thank you so much for these amazing insights. This was truly uplifting.

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About the author:

Chaya Weiner is the Director of branding and photography at Authority Magazine’s Thought Leader Incubator. TLI is a thought leadership program that helps leaders establish a brand as a trusted authority in their field. Please click HERE to learn more about Thought Leader Incubator.

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