What Entrepreneurs Can Learn from a Combat Veteran

What Entrepreneurs Can Learn from a Combat Veteran—with Waldo Waldman

Waldo, thank you for joining me on the show.

It is great to be here, Meny. I am super thrilled.

I have to start by thanking you for being on the show but more importantly, for serving our country and making the sacrifice that we all sometimes don’t want to do with joining the military.

I’m honored to do it, Meny. I love our country and I love people like you who make it up, especially great Americans who fight every day out of uniform because I don’t believe you need to wear a uniform to serve.

Every person could serve their neighbors, friends, community and make a difference in people’s lives. You have been a motivational speaker speaking on the topic of Never Fly Solo, which is your bestseller book. You joined us on one of the past LTB Summit or Let’s Talk Business Summit. Your content resonated well with the audience because it’s practical and we always say in the show, we love sharing no-nonsense advice on how people could be better every single day. When you are a better person, everything around you becomes better and you create a better society. Before we dive into a lot of the details, give our readers a little bit of the background. When did you join the military and for how long? Which type of missions have you flown into? At which point did you make the transition outside of the military?

I grew up in New York, down the street from where you live, out on Long Island. My dad was a mechanic at Kennedy Airport fixing planes. I’ll never forget seeing him work on the aircraft, smelling the jet fuel, and watching the planes. I said, “Whatever I need to do, I’ve got to fly.” That passion and drive impetus pushed me to say, “I want to be a pilot. I want to fly those planes.” I did well in school. I am fortunate that my parents pushed me and I studied hard. I graduated from the Air Force Academy and became an instructor pilot after a year of pilot training, which was special for me. I love teaching men and women how to fly. I transitioned to the fighter community, I flew F-16s in 65 combat missions in Iraq and Kosovo and some other garden spots that I may not be able to mention. I got shot at, I faced my fears and dealt with some things like claustrophobia and missile launches. A lot of little big things that impacted me. I decided to get out and join the reserve.

I went to business school and said, “I want to be in the business. I want to be creative. I want to create something unique and different.” Not that flying fighters wasn’t fun and exciting, but it did lack a little bit of creativity. I’m a creative person. I love people. I went to a couple of sales jobs. I worked for an Israeli technology firm and then an M&A, Merger, and Acquisition consulting company. I was carving my teeth in sales and applying the principles I learned in the military. I finally got the entrepreneur bug, became a leadership speaker and almost an executive coach and then I wrote my New York Times bestseller, Never Fly Solo. That’s the 30,000-foot view.

You mentioned that you got shot at and that overcame your fear. For business owners, in general, fearfulness is something that’s one of the best skillsets for a leader because we deal with employees, customers, market changes and competition. Fear is something that almost any challenge you have if you are fearless, you could overcome it. What could you share with us the mindset of being in that spot, even your best friend or somebody that you have been close with is being shot at and you have to run for cover? Bring us into that experience.

Fear is truly a motivator or a detractor from growth. It’s common for every one of us. We’re going to experience it in certain ways. Some people are more fearful than others. One of the things that I talk about is this true commitment. How committed are you? What is it that you’re fighting for? What gives meaning to your mission? You talked about the fact that you had your eighth child. I guarantee you would fly combat missions for your children and go through fire to save them. If you were out there on your own, jumping into a fiery building and there was nobody that needed and loved you. If you had to jump off a 33-foot high diving board and you’re afraid of heights like I was, or fly an eight-hour night combat mission in a tiny little jet, a cockpit, even though you were claustrophobic like I was. If there isn’t something on the other side, if there isn’t something that drives you, that forces you to serve, then you will not be able to face your fears because I truly believe that we commit more for others than we do for ourselves.

When you talk about going out there, flying in combat and knowing that we’re going to run away when those missiles are coming, is it part of being wingman and not flying solo? You know deep down through your training, through those core values of trust, integrity, that wingman you’re flying with has your back and you have theirs. Your fear dissipates when you know people are backing you up and you know that you’re fighting for them. You get out of your head, you’re not focused on your fears that are coming at you. You’re focused on service and servant leadership gets us out of our heads and helps us face our fears.

Business owners deal with emotion every single day, almost on a minute-by-minute basis. It’s a conversation that’s not easy on you to have or it’s something that got to do. You’ve got to go back to a client or you showed off work and the client doesn’t like it. Whatever it is, emotions play a role every single day of business. How do you deal with that in the military and what could we learn from that? Out of fearlessness, you mentioned that the mission, the end result and why you were there in the first place. You’re full of emotions. We’re all human and all these soldiers. Everybody in the military is human, people by nature. How do you deal with it? How do you separate it or maybe you don’t? Share with us a little bit that we can learn from.

You mentioned something, Meny, and I want to contradict it. It isn’t about fearlessness. There are a lot of speakers, consultants and motivational coaches who talk about fearlessness. That is something that is not human. The fact that you have your fear and you’re still willing to take action, I want you to think more about courage. I know you get this inherently, but as soon as people, businessmen and women leaders think about fearlessness, they start looking at their fear, their doubts and their insecurities with guilt. It detracts from them staying in the moment and saying, “I’m not thinking of fear,” which is pain-based and drives you down. It’s a drag on your motivation but courage that pushes you forward. It gives more meaning and drives and it’s not as negative of a connotation. I want everyone to change your vernacular from fearlessness, which is inhuman, to courage.

The second is the emotional play you can’t help because that fear is going to take over. It’s going to be apparent especially in the heat of battle when your life is on the line. When you’re watching your buddy get shot at, or watching four missiles, 55-foot telephone poles with warheads on end, streaking towards my aircraft in Iraq and in Kosovo with twice the speed of sound. You will be afraid, but here’s the kicker. You fight like you train. In the military when we practice and train, it is intense. It is severe. Everything is real except the bullets. We have certain limitations but we put the pressure on. We embarrass each other in a simulated battle and on the ground. We have high standards and we push each other to that emotional limit as best as we can before the missiles are real.

By the time you strap in, you take off and go master arm hot and the missiles are coming off your aircraft live and people are trying to kill you, at least you’ve experienced this emotional context. You’ve trained, practiced, and had it pounded into you much before that your training takes over, you become present. You’re in the zone. You’re supporting your wingman. It’s almost like you’re in training except the missiles are real. I want everybody reading when they’re thinking about their sales calls, dealing with objections, working with their contingency, sharing their software platform with safety issues, whatever it is, push your people and have high standards of training. They’ll be more emotionally ready when they’re out there in the field with the business and there’s money on the line.

Speaking about the military, we know that they are best in class about their leadership and their ongoing training and the readiness on a spear moment to be able to do the inevitable. I’ve heard you speak about the vision of a leader and understanding what’s the end goal and the mission in life and your business. In business and in the military, there is always something that is the stumbling block or we didn’t account for and all of a sudden we have to take a detour or change our strategy. How does that work in the military that we, as average business owners, could learn from?

Before we walk out of the door on a training mission and particularly on a combat mission, we have a briefing. We set standards and objectives for that particular mission. We assign roles and responsibilities to everyone in the formation, knowing that if one person fails to do their job, the whole mission could fail. We leverage our technology. We were skilled at our tools and technology, our radar, our weapon systems. We are trained in them. You talk about your technologies, tools, or CRM, that’s an important wingman so leverage it. The final thing that we do is we ask, “What if?” What if the weather changes? What if there’s an unanticipated threat? What if our radar fails? What if, God forbid, one of us gets shot down? We go through these contingencies and we start playing out scenarios, both in the briefing and beforehand in all of our training scenarios so that by the time it happens for real, that potential what if could pop up and you’re also prepared. You’re what we call mission-ready.

It goes back to what I was saying before about the hard training. You’ve got to plan all these contingencies and what-ifs and also understand that there may be something unanticipated that happened. If you’re trained as much as you can, most importantly, you have someone else in your formation which can help you, who may be dealt with that engine failure, that flame out, the safety incident, the supply chain problem, the financial issue, losing an important member, administrative assistant or your manager is working with someone else. These contingencies, you may not have the plan for, but those relationships that you build, perhaps even with the people reading this blog. Who are you going to call and say, “I need help,” that will allow you to breathe a little easier and be more controlled and less emotional? God forbid an engine failure happens in your business because we can’t do it all and we’re not flying solo, but having a wingman, that’s how you can deal with that emotional context and deal with those contingencies.

One of the things and lines that sometimes I go back and listen to the videos at the Let’s Talk Business Summit that you spoke at, you have the crowd shouting, “Push It Up,” which is understanding. Personally, it’s something dear to my heart when people ask me, “What do you feel is wrong with society? What could we do better?” I always say that we’re not giving it our best. Every single person has much more skillset that they could do with their life in business, personal, and their family, whatever it is they’re doing, but we withhold some of it. The military is known to be able to get every ounce of courage out of the people in service. What is the model of Push It Up? How can we apply it in the day-to-day?

I’ll give an overview of what it is. Essentially, when I was stationed in South Korea flying along with the demilitarized zone with the 35th Fighter Squadron, all the fighter pilots had a saying that demonstrated our commitment, our passion, the fact that we had each other’s back and that was Push It Up. We give each other the hang U sign and the pinky thumb would be sucked out. It was symbolic of the eyes of our Squadron mascot, Panther, as we call it in South Korean vernacular, Panton. You thrust your hand forward as if you were going to full power on the throttle and yell out, “Push it up.” That meant that you were there for each other. You were going full power.

When you look at your life, you look at your business, your relationships, the challenges that you have from business, from potential health problems, from the volatility of the economy to your workforce issues, whatever it is, your commitment, that pushes it up mindset is truly only tested when that fun, joy, and bliss stops when you’re going to war when the flameout happens. Your ability to push up that throttle and give it your all and most importantly, for your teammates and leaders, setting the tone for your team, going all out, engaged, exhilarated and encouraging.

That is symbolic to the person staring back at you every day in the mirror when you put on your flight suit and as you set the tone for your team and set the example. When you’re thinking of your fears and you’re worried about pushing it up when those challenges come, the choice is the hard one but you’ve got to make it every single day. That’s what we did when we went to combat with our squadron mates. That’s what leaders need to do. It’s easy to pull it back, but when we pull it back especially when we’re doing well, that’s where complacency lies and complacency as everyone knows can kill you. It can kill your numbers. It can kill your relationships. It can kill your brand.

I want to turn the conversation to the concept of your book, Never Fly Solo, and understanding that in order to be able to achieve what you are set out to do, you’ve got to be able to have a trusted environment. To be able to be there for your teammates and work as one team with one mission. I want to dive into asking you the following question and this is something that I’ve heard from other business owners and leaders within companies struggle with. In any company, there’s going to be the leadership team. There are going to be people doing clerical work and data entry. There’s going to be a serviceman on the job and then the warehousing, whatever types of positions within a company. This is more of what you do in the teaching. How do you bring everybody together to understand how they affect the end result? Even in the military, there are people that go there for those operations and driving those F-16s and then there are people that are fueling the flights. How do you bring everybody together that everybody feels part of that mission?

That one team, one mission philosophy and Never Fly Solo was something that I learned in the military. It is a part of my book and a lot of my seminars and coaching is realizing that not everybody in the 35th Fighter Squadron or 8th Flying Training Wing is a fighter pilot. We have the security policemen guarding the base. We have the maintenance technicians, the intelligence people telling us where the threat was. We have the tanker pilots fueling our jet. All these other people who help us to get in the plane and hit the target. What we did in the military was we always brought everybody together at least once a month. It was called the commander’s call. What we would do is the flight commander, the leader, the CEO would bring all those people together, a couple of hundred people, and we’d share what was going on the squadron.

We’d have hail and farewell. We’d welcome the newbies. We’d have the other people leave and we say farewell to them. We celebrate with their families. We bring up the staff sergeant of the month, the enlisted person who wasn’t flying jets. We’d recognize and reward all these people and we’d make sure that we understood that we were all part of the mission. Here’s the problem, especially when you’re a “cocky fighter pilot” or the business owner or the top sales performer in your team. You may forget about those unsung heroes. One of my lessons learned is when I chewed out a young enlisted crew chief who was fueling my jet. He didn’t fill it up enough. Long story short, I chewed him out. It was disrespectful and I used foul language and my commander found out about it.

He made me get up the next day and spend the entire twelve-hour day on the hot, sticky, sweaty flight line with a bunch of those young crew chiefs. Those 25-year-old kids whose job was to fuel and fix the jet. I learned how hard that job was. It humbled me. It made me more appreciative of those people. I never forgot that lesson. When you walk the flight line with your teammates and find out what finance, HR, IT, all those administrators who may be younger than you or maybe have a different skillset and see the big picture, it builds that trust. Sometimes it’s learning the hard way like it is for me. Other times, you can lead it and take proactive action by getting out there with your team and appreciating them and getting to know them.

I usually use the analogy when people speak to me about this particular challenge that they’re facing is look at a company as a puzzle. A puzzle needs every single piece regardless if it’s the middle of the puzzle or a side of the puzzle. Every person in the company is part of the puzzle. You only have a picture-perfect puzzle when everybody’s doing their job effectively and working together. Let me go back to something in the military and then I want to move on to what we see in the workforce as you’re a mentor, coach and speaking on the topic of leadership and Never Fly Solo. It is something that I feel that a lot of business owners are lacking, which is the concept of quality of discipline.

Nobody could think about the military or think about our troops not thinking the word discipline, the way that they act, they react and they train. A lot of business owners, their biggest challenge is they’re all over the place and they can’t focus. There is a lack of focus. I want to hear from you, how important is discipline and is it trainable? Could a person become more disciplined? Could this be trained as you saw in the military? If somebody is all over the place, especially if they still use the excuse, “I’m an entrepreneur,” which by nature means, “I’m all over the place.”

Discipline is the glue that instigates action. It’s the glue of a team. It’s an important concept. It’s aligned with commitment. When you’re disciplined, you no longer let emotions take charge. You deal with your emotions. You get out of bed and say, “I’ve got to hit the gym as I did.” You may not want to, but because you have the discipline, you’re able to push through that pain. Discipline is also when it comes to integrity many times. Sometimes we’re forced to take the easy way out. Look at what happened with the news with the Boston Red Sox and Houston Astros stealing signs. They lack the discipline, which is inherent in the integrity of doing the right thing. In the military, when there were infractions and discipline, which by the way didn’t cost a sale or lose a customer, it could cost a life. We would hammer each other and come down in the most professional way. They were reprimanded. If you did not lack the discipline and accountability to do your job, back each other up, fly the jet safely and show up to the mission briefing on time and do what was expected.

You quickly learn that in a culture of accountability, a high-performance team where it was a lot at stake and there was a high risk, if you lacked discipline, you were going to not only be the one reprimanded in the squad and you’d lose your reputation. You wouldn’t get the opportunities for promotion. You wouldn’t be trusted to go to battle. Shortly thereafter, you may decide to turn in your wings on your own or they would remove them for you. Discipline is a huge deal in the military. It’s not just closing deals and building a business. As the leader, you have to emulate the discipline, the hours, the work ethic, the accountability, the discipline to fess up when you mess up in front of your team. Because you are trying to instigate that DNA and then procreate and build that culture, the DNA of that group, the blood. Discipline is a key factor in that. When you set the tone, it gives you more credibility when forced that standard of discipline and accountability with your team.

[bctt tweet=”Complacency can kill you, your numbers, your relationships, and your brand.” username=””]

Is it a teachable skill? You have the entrepreneurs that started their one off-type of business and all of a sudden, they’re hiring a team and discipline is important. Is that something that you could learn and be better at?

I do believe so. Think about your kids, when they touch the hot stove or whatever, we use that technique. They touch that hot stove. They don’t have the discipline not to listen to mom and dad. Suddenly, they get that blister and say, “That consequence was big. I’m going to stay within my lane on this one.” There was a little bit of pain and a negative consequence. By the way, you’re not judging someone, you’re disciplining the behavior. You will learn that if you’re not accepted, if you’re reprimanded, if you’re not brought into the folds, if you’re not asked to do the good jobs, I think you’ll say, “I better maintain that discipline and follow the rules. If not, I’m going to be out of a job or I better do something else.” I do think it’s teachable. You have to have somebody that’s coachable and last but not least, approachable to be open to feedback on their lack of discipline, where they’re like, “Thank you for teaching me and coaching me. I’m willing to accept the consequence. I’m willing to learn. I’m willing to get better. I’m going to get up and wake up every day with more discipline and more commitment to doing the right thing and adherent to the standards of my squadron.”

Let’s move into the private sector. As you go around, you speak to thousands of people around the world, small companies, large companies, and general conferences. We see in the marketplace, there are companies that are killing it. They’re focused, strategic and people love their products. People love to work there and so on and so forth. There are companies that are trying to make ends meet. Working along for a few years and all of a sudden, either going out of business or staying flat. In your opinion, based on what you’ve seen in the marketplace, what sets apart those top 10% of those businesses that are killing it with success?

It’s all about relevance. It’s about relevance in the market, to your customers, your clients and demonstrating value, not just slinging materials of service, but truly going above and beyond with your clients and your teammates to differentiate yourself in a commoditized space. Relevance is tied hand-in-hand to innovation, technology-wise, supply chain-wise, marketing-wise, and social media-wise. There are weapon systems that are constantly changing in the fighter pilot world, new technologies and tools. If you don’t leverage them, strap them on the jet, upgrade your systems and then train to them, you will be irrelevant quickly.

The best leaders, the best companies are constantly evolving, innovating, maintaining relevance, and adapting to the changes and putting in the hard work, and being as proactive as possible. The leaders reading this blog, leveraging their marketing tools or technologies, new CRMs, you’ve got Millennial workforces out there, different generations. How are you leading them? Instilling commitment and discipline in them. What did they need? That’s the constant struggle that we all have, this peak performing fighter pilot businessmen and women to stay relevant and keep hitting the targets. It’s not easy. It takes sweat. It takes commitment and discipline, but it’s definitely doable.

One more thing that I wanted to get to where you speak a lot in the content you put out on LinkedIn and on other places, is mentorship. Speaking about in the military, the mentorship training, coaching, what viral part it plays in the rest of the soldiers and the rest of the team and how they get great at what they do. How important is mentorship for everyday business owners? How would somebody go about finding a great mentor?

I have a saying, “Make your friends, your mentors and your mentors, your friends.” My dad always used to say, “Be careful who you hang out with on the weekends.” I take that seriously. For guys like you, Meny, who we have a relationship, I know I could call you and you can give me advice, call out my blind spots, give me feedback that I may not want to hear but need to hear. My friends are brutally honest with me. They’re successful. They have good families. They emulate excellence as best as they possibly can, meaning they’re not perfect. I want to constantly be surrounded by those people. As you’re assessing your wingman, the men and women in your life who you hang out with, are they mentoring you? Are they setting the example on accountability and have high standards? Are they demonstrating mediocrity? Sometimes we have to jettison those people and stay with people who are going to lift us up. That’s an important aspect as well. You can be a mentor to your team and you can also find mentors informally, meaning, watch what your leaders are doing. Ask them for help.

I don’t believe in picking people’s brains. I think you should massage their minds and connect with them. Be willing to ask somebody to be your mentor, but don’t pick their brains. Do it respectfully. Buy them lunch, connect with them, show them respect and pay it forward. Model leadership in your personal life through your workforce and then find some free mentors. They may cost you $10 or $20, buying an audiobook or going on Amazon and buying a book. There are many mentors on YouTube, watch, listen, feed your brain with great audiotapes. Listen to podcasts. Find those inexpensive, easily accessible mentors on a podcast or on the web and take advantage that way. You don’t need formal mentors to win. You need to seek it out and leverage the amazing tools that are available to you. Last but not least, I want to go back to our responsibility as leaders to mentor and give our wings away to other people.

I got a text from a young man who was struggling. He was a successful business person, but dealing with drugs and family issues. I went to breakfast with him. I gave him some books to read and I followed up with him. I pushed him and he sent me a great note. I won’t go into detail, but he’s taken action and thanked me for helping him. He still has a lot of work to do. I didn’t ask for payment because I think it’s our responsibility as a human being, as a giver to help those people who may be in the dungeon who need to be lifted up.

That’s the way that we could give back to society for we’re able to have certain skill sets and we have content to share. I’ll add to what you said. In my professional life, I’ve always made friends with people that I’ve seen smarter than I have more to share and follow them regularly. Even on LinkedIn, I follow their content. As soon as you feel that you almost know that person because you’re following that consistently, send out a message and say, “I love your content. Thank you for what you share. Could we go out for lunch or could we have a ten-minute conversation? I have a practical question that I think you could help me.” I get those requests all day long and I try to fulfill as much as I could, but it will always be obvious from that message what the request is. Is the request, “I want to go for lunch,” and I have no idea what we’re going to be discussing or the person is saying based on what he’s outlining, he has a direct question that I think I have the answer? If I give him ten minutes, this could be the best ten minutes I spent my whole week.

That’s how you do it honorably. You ask and maybe send them a personal handwritten note. I’ve done that plenty of times. Don’t be afraid to do what people aren’t doing. The more digitized we get, the more social media eyes we get. People don’t get handwritten notes or a card. That marinates the steak of the relationship very nicely when you go above and beyond sending that personal note. Don’t try to go too high on the ladder of life above you as well. You’re not going to try to send a Facebook note or a LinkedIn message to somebody, a celebrity brand or a Fortune 100 CEO. You’ve got to incrementally work your way up, leverage those relationships, do it tactfully and you’ll get there and find those mentors who can help shift your trajectory even with that ten-minute conversation.

I’m looking up on my desk because it reminded me that I have a gift that you sent me after you spoke at our LTB Summit. It was unexpected. I got a thank you card and a gift. It was a monument or a statue and it’s sitting on my desk ever since.

I’m glad. It’s a fighter pilot bust. It’s a sculpture and I give that out to my top clients. Everybody gets some gift from me, a handwritten card. I’m glad that you have that, Meny. There was something that you did for me that we try to get in the business. You hired me. You wrote me a check, which is a blessing. We built a relationship afterward, and thus, this conversation is a byproduct of that friendship. We’re all blessed and fortunate to be able to have business relationships to be able to put our kids through school and food on a table and reap the blessings that our Creator has given us.

This was amazing and I know that our readers will take a lot of good stuff out of this. Are you available on audio as well?

It is an audiobook. I was mentioning to you that audiobook, which is $20 on Audible, because of our relationship and friendship, I will offer everybody a free copy of that New York Times bestseller, the audiobook for anyone that wishes to get it. I could share the website. If you want to connect with me on social media, go to Waldo Waldman. I’m all over LinkedIn, Twitter, Instagram, etc. If you go to my website, which is www.YourWingman.com/nfs, put your name and email address, and you’ll get a link to the Never Fly Solo audiobook. Share it with your friends and with your kids. There’s a lot of good content on there about courage, commitment, and business skills. Drop me a note and let me know what you think about it.

Thank you for that. Let’s close with the four rapid-fire questions. A book that changed your life.

How to Win Friends and Influence People by Dale Carnegie.

A piece of advice you got that you’ll never forget.

Hire an assistant at your soonest possible time in the business and it will free up your mind to become more creative.

Anything you wish you could go back and do differently?

I wish I had more than one child and that I got married a little sooner, but I got married late.

What’s still on your bucket list to achieve?

It’s facing my fear by going skydiving.

We’ll call you out on that.

I’m going to do it. It will happen. I’ve just got to push it up.

Thank you for joining us. I know your time is valuable and that is why in the name of our readers, we will forever be grateful for sharing some of your time with us.

It’s an honor to fly with you, Meny. Godspeed.

Thank you.