[smart_track_player url=”http://traffic.libsyn.com/themassimoshow/massimo_show_waldo-part1.mp3″ title=”An Action Plan from the Air Force Pilot Who is Scared of Heights, Lt. Col. Waldo Waldman Part 1″ ]


[smart_track_player url=”http://traffic.libsyn.com/themassimoshow/massimo_show_waldo-part2.mp3″ title=”Quitting with honor – when quitting can get you back into the cockpit of your mission with Lt. Col. Waldo Waldman, Part 2″ ]

My very special guest, Lieutenant Colonel Robert Waldman, better known as Waldo, served as a decorated fighter pilot where he led missions worldwide before earning his MBA and thriving in the private sector. I met Waldo several years ago in a mastermind group and we hit it off immediately. I’m proud now to call him a friend and a confidant. Now, as impressive as Waldo’s background is – Waldo is also a Hall of Fame Speaker and a New York Times bestselling author for his book, Never Fly Solo – In Part I and Part II of our interview, we dive deep into the business and life lessons shared in his amazing book along with several other jewels of leadership as well as some incredible stories from Waldo’s flying days. Please get ready to Never Fly Solo again.



Full Transcript of Part 1 –

Waldo:   Commitment to excellence is only tested when the fun stops. Your passion is only tested when the fun stops. What actions are you going to take when you’re on the edge of the diving board, afraid of heights, looking down and wondering if on the opposite side of that diving board is where my future is?

Hi, this is Rod Santomassimo and welcome to The Massimo Show. The objective of the Massimo Show is to share how you can maximize your personal professional margin. That’s right – let’s make more money in less time. Let’s turn chaos into clarity, confusion into confidence and income into real wealth. Along with sharing my insight and how I grew a multimillion dollar professional business, we’re going to bring you expert advice from a variety of authors, consultants, and thought leaders who provide the tools you need to maximize your own personal and professional margin. Welcome to The Massimo Show!

Rod:    Waldo, I can’t thank you enough for joining us today and I want to dive right into it. Our audience are independent workers, independent contractors, solopreneurs and small business owners, and you have this concept in your New York Times bestselling book, Never Fly Solo, so as we launch this, can you help us understand that concept of Never Fly Solo and what that means to you?

Waldo:   So with regard to the concept, you know, I learned it in the Air force as a fighter pilot, combat the whole nine yards, realizing that essentially, you can survive on your own but you win together. We’ve all heard the concept of teamwork and collaboration and you need other folks on your team, but a lot of times, especially as a small business owner – we both are, I’ve had this business for 15 years and I do speaking and coaching and I’ve got employees and independent contractors – realizing that you have a limited, myopic often, view of business and situations from your own cockpit and that when you nurture relationships with different thinkers – just like we were talking before this podcast – folks who have the same values but different perceptions of life, different perceptions of business, different relationships, different ways of looking at things, now you’re gaining insights from people that you can’t think of on your own. It’s not just about getting help, but insights and advice and often some feedback that you may not want to hear but need to hear. I think when you’re a business person, as an entrepreneur, sometimes a great wing man will be brutally honest with you and bruise your ego even. And those are the types of people you have to nurture in your life. So that’s where I believe the Never Fly Solo concept goes a little bit beyond the scope of just teamwork in business.

Rod:      So you mentioned this concept of wing man and sort of the analogy to your service which we understand, but is a wing man truly just an individual? Is it a combination of individuals? Do I need just one wing man or a series of wing men? How does it work?

Waldo:   Great question. Because I think you need as many as you possibly can. But a lot of people call out and say, “Oh, I’m your wing man. You know, hey blah, blah, blah.” Well, no, that takes a lot of trust. That takes a nurturing of relationships. That really means going out of your way to get to know somebody from the inside out. So it’s not a very casual term. It’s somebody that when the proverbial crap hits the fan, they’re going to be there for you and you’re going to be there for them. So you’re probably not going to have too many great wingmen in your life. I’d rather have a few close ones, than a bunch of just cursory, nonchalant casual wingman. So it’s ultimately somebody that you can go to for help. That’s the quickest, easiest way to look at it. When the crap hits the fan, when the missiles come, when the life challenge happens, when the revenue is down, when the economy craps, right? Who are you going to call when you truly need great advice. And when you think of your personal life, when you think of business, when you think of networking, sales, business development, when you think of technology or perhaps, you know, on this Zencastr software here, you got a podcast, you talk to me about some folks that you coached that gave you some insights – you ideally want wingmen who have expertise in certain areas. The ones that I just mentioned who you can ideally call. So essentially, you may think of yourself as flying solo in your cockpit. You know, I’m sitting in my office by myself, my assistant’s in a room next door. So you never really fly solo in your cockpit of your office or your F16 when you have other folks outside that you can call for help. So nurturing them, building them up and being there for them is also a great way to nurture those relationships when you need them as well.

Rod:   Fantastic. So I know the audience is going to want to hear about your actual service. So let’s get to the beginning of this. I mean, you were a kid growing in the northeast and you decide to go into the air force. Why,? Why the Air Force? What drove you to become a fighter pilot?

Waldo:     I was always passionate about aircraft because when I was a kid, my dad, who is a mechanic at Kennedy Airport in New York City took me and my twin brother Dave to the airport and I jumped on the tarmac, I smelled the jet fuel, he sat us in the cockpit and I was hooked. Right. I just was like, I gotta do this thing. And so my dad who worked on the plane too was totally blue collar. He was a navy mechanic and I just got this bug and he was talking to me about the academies, etc, etc. And I’m like, I’m not going to get up at 6:00 AM for four years. They work too hard. And then the guidance counselor actually told me about it in 10th grade and he saw potential in me and gave me a perspective, gave me an insight, that created this whole new dream of mine. A lot of times when we hear stuff from my parents, and even sometimes from people we call our friends, it doesn’t make sense until somebody that you respect gives you a different perspective on looking at something.

Waldo:    So my dad could talk to me about the Naval Academy, the Air Force Academy a bunch, but it was up until my guidance counselor mentioned it to me. And look, I love challenge. I love sports, I love excitement. I love anything that’s going to get in my way, that’s going to help me grow and what a great place to go, such as the Air Force Academy where I can really be not only in that environment, but surrounded by other men and women who were passionate about growth and kicking butt. And so to me it wasn’t just about flying planes, it was about the challenge. And that is something I think that we all need to think about and the reason why we most likely got into the world of entrepreneurship where it’s risky every single day. Where you are going to get shot at. Where you could possibly lose? And so for me, and I would assume for most of us on this call, on this podcast listening, you’ve got to ask yourself, am I willing to lose today in order to possibly go out there and win?

Waldo:    And the more I grow and the more I’m in business and the more I win and lose engagements and win and lose all sorts of things, I realize that it’s that challenge. It’s the juice that gets me going. And the more I lose the battles, the more likely I’m going to eventually win the war, right? So what battles you willing to lose? What failures are you willing to go through? The tribulations, the crucibles, the garbage that’s just going to totally beat you down and say, yes, I lost that battle, but eventually I’m going to win the war. And that’s the constant journey. And the wars are changing. The theaters of operation are changing. But isn’t that the juice? Right? And once you lose that juice, you got to start thinking yourself, man, it’s time for me to do something different. Get out of this business, take another risk, find somebody that’s going to reinvigorate that passion and juice that’s critical for entrepreneurship, because, man, when you’re getting beaten down, and I’m sure there are folks listening to this that are beaten down, they’re a little worried or they’ve been doing it for 20 years and like, ah, Waldo, I’m just pulling back the throttle a little bit. I don’t have that juice anymore. Listening to podcasts like this, getting together with a kickass top gun, somebody who’s making it happen, who can reinvigorate you and give what I call more meaning to the mission. That’s the Air Force Academy. That’s flying an F 6 and that’s taking a risk. And sometimes it takes somebody else to reinstill that passion and give you the fuel to get back into the crucible and keep enjoying what you’re doing.

Rod:    Okay, so now I’m a little confused. You talk about the juice, right? And I agree with you. Everything you said I agree with. I got this issue, although is that my daughter loves, loves roller-coasters and my wife does not. And so when we go to any amusement park or theme park or whatever, we have to go on the roller coasters. There’s only one problem – I don’t like heights, I just don’t. But I have to go because someone has to go with her so it’s gotta be me. And then I read in your book, here’s this decorated fighter pilot, right? So many missions and yet you’re afraid of heights!? So how do you do this – is that part of the juice is taking on that fear? Tell me about that – how does that work with heights? And then on top of that you share in the book, you’re claustrophobic. Now I’m really confused. How does someone like that become the successful fighter pilot that you were?

Waldo:    Great concept and I know everybody’s kind of biting at the bullet to hear this context because at the end of the day the things are going to get in the way are the challenges. So for me, for folks that are listening, I was always afraid of heights when I was a kid. Right? My twin brother would make fun of me – we’d be at the local community swimming pool, he’d be jumping off the 10 foot board and I would be climbing down the ladder watching them make fun of me. And I was like that all through my years – I was such a wussy I really was. And it’s funny cause my eight and a half year old son is kind of afraid of heights too. And I’m trying to coach him through this stuff. So when I went to the Air Force Academy, in order to graduate, you had a complete something called water survival training, and part of that training was jumping off a 33 feet high diving board. And when I was a freshman and they took us to the class they said you can’t graduate unless you jump off that diving board. You will not graduate. You can have a 4.0 but if you don’t jump off that thing, you don’t graduate. No chance of being a pilot. So now I talk about passion being greater than the fear. My passion, my love for the future, my love for flying jets and the potential for going out there and doing something great was blocked by this 10 foot concrete wall called jumping off this diving board. And I was the last in my class to jump off that thing. But I jumped. I jumped and I knew that in order for me to break my barrier, I had to jump off that diving board.

Waldo:  So here’s one of the points – it’s about commitment and commitment is your attitude in action and commitment really to the concept of excellence. I’m really talking about excellence and building a high performance culture from the inside out with yourself and with your team. Commitment to excellence is only tested when the fun stops. Your passion is only tested when the fun stops. What actions are you going to take when you’re on the edge of the diving board afraid of heights? You know, looking down and wondering on the opposite side of that diving board is where my future is, right? On the opposite side of that fear is where growth is. When you’re in the jet of your life, your cockpit, and you’re dodging missiles, whatever it is, finances, relationship issues, healthcare scares, right? The crap that’s shot at you where you suddenly doubt yourself, the action that you take when the fun stops, when the fear comes is where your future lies. So that crucible that I faced, that challenge of jumping and stepping out of my comfort zone, opened up so many of those doors.

Waldo:   And the only way you could do it is tapping into what you truly love and what is on the opposite side of that, because sometimes people lose sight of it. They don’t realize what’s at the end of the diving board, what’s in the water. And some of us are flying by the seat of our pants. We’re on auto pilot, and if you’re not tapped in and tuned in to what it is that you’re doing and why you’re doing it, where is your future? What is the dream on? What’s the charity? What example do you want to set for your kids? Because you jumped off that diving board and kicked butt and took some risks, right? Once you start tapping into that and it’s not easy to do sometimes – sometimes it does take a wing man or a wing ma’am to give you that insight – now you’re finding the courage to take action and when you take that action, you’ll develop the courage, you’ll develop more skills and ultimately more confidence, more confidence to take on 60 foot diving boards and greater missiles and greater tribulations, and that is called life That is called living in excellence.

Waldo:   That’s called the opposite of mediocrity. It’s somebody who saying, I’m out there dodging these missiles and dealing with my fears and constantly jumping and jumping and jumping and failing and jumping and winning and jumping and the scars of our character. Being more and more present, but that’s what builds growth and character in life. And you just gotta be willing to go through it.

Rod:    I have to tell you, that commitment is only tested when the fun stops. Commitment is your attitude in action. Wow. Great takeaways there. Thank you for that. So we talked about these fears and so for example, yesterday I was actually presenting a workshop to a small group and this one woman told me she couldn’t prospect, she couldn’t make calls and we worked with her and she made her first calls and we tell her what to say and what to do. And guess what? She got two meetings in her first two calls and then she stopped. And I asked her why and she said, I’ll get rejected next time. It’s going to happen. I lucked out, I’m going to get rejected. So a lot of our listeners today are always prospecting for new business and yet many of them fear asking for the business. How can you help those or suggest to those how to face those fears like you have and your fears and potentially overcome some of those fears of asking for the business?

Waldo:    Great question. Because at the end of the day, you know, sometimes we’re our biggest enemy. We’re our biggest missile. That inner wingman, the person putting on the flight suit when we get dressed every morning and looking at ourselves. We have to be able to say to ourselves, do I trust him? Do I trust her? Am I prepared? Am I confident? Where’s my courage? What’s holding me back? These are deep, deep questions that you ask. And then as entrepreneurs, it’s even more important for us to ask those questions and challenge ourselves because we’re ultimately making the decisions. We’re ultimately providing the revenue and the resources and the opportunities for our family and our children and the people that we love. So one of the things I really focus on, I obviously just talk about passion, knowing what it is you’re fighting for, which your 33 feet, I always say, right?

Waldo:    What is your personal 33 – the challenge that you have to overcome? And we’ll talk about my claustrophobia a little bit later, right? Because that’s another thing that got in the way. Preparation, preparation, being mission ready, developing the confidence. Let me tell you why that young lady was a little bit afraid. She was dependent on her luck a little bit. Obviously you gave her some coaching, but she didn’t do it enough to build up the comfidence necessary to stay in the cockpit and dodge some new missiles. So as an entrepreneur, as a leader, as a business owner, you’ve got to constantly figure out what you need to do to prepare and stretch beyond the comfort zone. I mentioned before about losing battles to win the wars. Well, you know, when I got out of the military, I went to business school. I was in technology sales, mergers and acquisition and consulting.

Waldo:  I cold call thousands of times, thousands. My twin brother still does the business. He taught me a lot of what I know. Or so he likes to tell me, right? But he’s great and it’s a constant phone game. Calling up, dealing with rejection, figuring out what you needed to say on the phone. Now the way I became better at it is I asked for help. I got coaching from my twin brother, other people, I listen to podcasts and read books, but the more I practiced it, the more I got mentored and coached and gave some feedback, you know, from some other folks. Look, I said, look, listen to this call. I want you on that call, let’s record it, let’s review it afterwards, embarrass the living heck out of me. Bruise my ego. Tell me what I did wrong. Tell me what to say or what I did say that was right or wrong.

Waldo:  Right? And so it’s not just about getting some coaching and some advice. It’s literally putting yourself in the cockpit and getting shot at and being fed some feedback from your friends and bruising your ego. And so I would challenge her just to get used to failing more, get used to having the feedback more and then role play a lot more so that she’s failing in front of her peers. You see in the fighter pilot world when we practiced, like I mentioned, we do it in the simulator, we do it in front of each other. We put pressure on us – called practicing under pressure. Chair flying. We chair flew the missions. If you picture yourself sitting in a chair, right, if I’m in a chair right now doing this call, I would practice and we would practice together with the throttle and stick and go through the maneuvers.

Waldo:   And one of the flight leads would say, “All right, you got an engine fire in your left engine, red blinking light. What are the procedures? Go!” Uh, uh. “Your other jet’s on fire.” Uh. Maintain aircraft control… Uh, uh, get to the checklist. “No. Maintain aircraft control, analyze the situation. How are you analyzing the situation?” We’re just going back and forth, back and forth, sweating, turning red. “Okay, let’s start over. That sucked. All right, let’s start over.” And so we practice, we go through it. We embarrass each other in front of our peers because we know we gotta fly together. We know we have a responsibility to take care of each other. And protect our lives. So get in the cockpit, practice, get coaching, embarrass yourself in front of your peers, pay for it. I just spent 5,000 bucks last week for a speaker coach for a day, right? You got to invest in people telling you you’re screwing up, right? People will help you. Invest in folks who have your best interests, not just from people that are your wingmen who your friends and partners and coworkers, but folks who you pay for. It’s another way you’ll build more confidence to get on the phone and deal with rejection and build the competencies necessary to win.

Rod:    I appreciate that, Waldo, and you know, a quote that you and I are very familiar with, it was credited, I believe, to a Navy Seal – We never truly rise to the occasion. We only fall to our highest level of preparation – and that’s so true in everything we do. Great quote and it bears repeating. We never truly rise to the occasion. We only fall to our highest level of preparation. If you’ve enjoyed this great interview with Lieutenant Colonel Robert Waldman, you’ll want to join us for next episode where we will continue this conversation with Waldo, including talking about his claustrophobia and why sometimes it’s okay to quit. You don’t want to miss it. You can find out more about Waldo at yourwingman.com. I’m Rod Santomassimo and thanks for joining me here on The Massimo Show. For more information about the Massimo Group, please check out Massimo.coach. Again, that’s massimo.coach. We’ll talk to you soon.

Hi, this is Rod Santomassimo President and founder of the Massimo Group. Did you know that for over the past 11 plus years, we’ve worked with thousands of independent contractors, solopreneurs, and small business owners just like you in repositioning their and/or their team’s efforts so they can build the personal professional practice they’ve always dreamed of. We provide coaching programs for all levels of experience, earnings and, yes, success. So if you’re finally ready to get off that transaction treadmill and chasing deals that are growing nowhere and start building the personal professional business and life consisting of greater wealth and more time, well, check us out at massimo.coach. That’s massimo.coach.

Full Transcript of Part 2 –

Waldo:     Don’t buy into the philosophy of never quit. Sometimes quitting is the best possible thing you can do in order to get back into the cockpit and fly a mission that you believe in, that you’re passionate about and that’s going to help build more character and courage.

Rod:    That was today’s very special guest, Lieutenant Colonel Robert Waldman, better known as Waldo, who served as a decorated fighter pilot where he led missions worldwide before earning his MBA and thriving in the private sector. Now, as impressive as Waldo’s background is, Waldo is also a Hall of Fame Speaker and a New York Times bestselling author for his book, Never Fly Solo. I met Waldo several years ago in a mastermind group and we hit it off immediately. I’m proud now to call him a friend and a confidant. In today’s episode, we’ll pick back up on my conversation with Waldo and we’ll learn about his claustrophobia and also why sometimes it’s okay to quit.

Hi, this is Rod Santomassimo and welcome to The Massimo Show. The objective of the Massimo Show is to share how you can maximize your personal professional margin. That’s right – let’s make more money in less time. Let’s turn chaos into clarity, confusion into confidence and income into real wealth. Along with sharing my insight and how I grew a multimillion dollar professional business, we’re going to bring you expert advice from a variety of authors, consultants, and thought leaders who provide the tools you need to maximize your own personal and professional margin. Welcome to The Massimo Show!

Rod: You mentioned something there that I want to segue to and that is about this claustrophobia and the woman who, after two calls, she quit. She said, I can’t do it anymore. I’m going to quit. And in your book, you also talk about an episode where you quit, which I found extremely refreshing to think, oh my goodness, this fighter pilot, this amazing person that we rely on for our freedom, quit! But since you put it out there, tell us about that episode when you quit and yeah, let’s talk a little bit about that claustrophobia.

Waldo:    Are you saying this young lady who you were coaching, she eventually quit? She didn’t want to do the cold calling?

Rod:    No, no, after two calls, she said she’s going to quit because she was afraid she’d get rejected because she had just two meetings. So she just quit and stopped calling.

Waldo:     Was she quitting her job as well?

Rod:    No, no, she just quit for the day. There’s no doubt that out there in the workforce, whatever you all do, our listeners, there are times you just quit. You just say, you know what, I’m not going to do this anymore? I’m not going to make the calls anymore. I’m not going to do the marketing. I’m going to leave for the day, I’m having a bad day. I’m not going to do it. I’m going to quit. Hoping not in the longterm, but just in the short term.

Waldo:   Right. So here’s the point. I appreciate you sharing that example. I have a saying – Quitters never win, but winners sometimes quit. And there’s a follow on quote to that – You have to quit with honor. So let me share with the folks that I struggled with claustrophobia as a fighter pilot. I almost died in a scuba diving accident three years into my 11 year active duty flying career and, long story short, it brought out this latent claustrophobia that I’d never thought I had. I basically had PTSD, post traumatic stress disorder, not from a combat mission, but from almost dying scuba diving. So instead of being 30 feet under the water having a panic attack, now I was finding myself at 30,000 feet with a mask on in this tiny enclosed space having these panic attacks, which was brought on due to that PTSD I experienced scuba diving. Now, I didn’t quit. You know, I talk about passion being greater than the fear, number one, but it was also my sense of responsibility.

Waldo:   The fact that I had wings on my chest, that when I was flying those eight-hour night combat missions I had other men and women who were depending on me to go out and do my damn job and protect them – that ego, that sense of responsibility, the fact that I didn’t want to be embarrassed and be the quitter, and the fact that, like I said, others needed me kept me in the cockpit and it pushed me to get more and more used to being in those situations and my claustrophobia, my fear, my anxiety, eventually diminished. Didn’t go away. Your fears and anxieties will never go away. They’ll just be covered up by your strength, your resilience, your health and fitness, your competence, your mindset, your preparation – those shield the fear missiles. The missiles don’t go away. You just got an iron shield of confidence that’s a byproduct of your preparation and mindset and all those other things, right? I can go into this for hours, but the sense of responsibility helped me stay in the cockpit and also gave me some great experience and examples in which to share with my eight and a half year old son who’s failing in soccer and getting his butt kicked in karate and being sometimes bullied at school – all the things that our children and the people that we love have to deal with as we grow up. And so my fears, my anxieties, my challenges were gifts for me to deal with my changes, but also that to be the example through my character, through my stories, through my quote unquote wisdom, whatever you call it, for my children, for my coworker, Amy, who is sitting next door, for my buddies who are dealing with some health challenges because I have been in that crucible.

Waldo:     So my point to you, and then we’re going to get back to the quitting thing, is realize that those challenges and issues that you’re going through in your business and all the cursory things that are part of it aren’t necessarily just for YOU to grow. Think about who can learn from your example, your mentorship and coaching, your wingmanship, right, and say, man, this really sucks right now. I am not enjoying this, but this is going to be great, great fodder of information and experience to share with my son or daughter or my new wingman who I’m coaching who hopefully will run my business one day. Or perhaps my buddy who’s going through a drinking problem right now or a divorce or who’s thinking of starting his own company after leaving So-and-So Company, you know, for 10 years. So that example, those challenges and tribulations are for other people, too, if you truly care about others and want to help others, which is a higher level of thinking in life as opposed to surviving just to put food on your table. So think about that, listeners, on who needs you to succeed and what example you can set because those values great content for other people to learn from and for you to coach and mentor.

Waldo:   So I never quit on a combat mission because it was combat. People needed me, man, I sucked it up. And by the way, I became Instructor Pilot of the Year, Flight Leader of the Quarter, I had all these awards despite the fact that I was dealing with all this crap going on in my head, in my life, those missiles. So you, listener, or the people who are part of your team, they may have some quote unquote claustrophobic panic attacks going on in their lives. Are they still able to deal with them and still execute and still fly their jet, their job, right? Cause a lot of people go through it, right? A lot of the issues that go on in our lives may have nothing to do with work and may have to do with some other things going on. So think about that as you’re getting to know your teammates and you’re building relationships with your wingman. Know what’s going on in their life and how you could potentially support them. But it’s ultimately how we act despite the challenges, despite the physical or mental issues that may be going on. Ultimately, it’s about our performance. And there are some great successful people out there – we all know them, and we can name them – who have issues and challenges, but are still able to kick some butt. Right? And maybe that’s you, right?

Waldo:    So my claustrophobia was always there. I was always able to break through it. It got easier and easier and easier. Some missions were tougher than others, but the biggest challenge in my life came when I was flying on a training mission, not a combat mission, where it was war and life and death. This was a mission where we were ferrying – flying back six F-16s from Saudi Arabia after a combat deployment to South Carolina, down the street from where you live, Rod. And so we were flying from Saudi Arabia to Spain and then Spain to the United States, and they asked for volunteers out of the 12 pilots present – Who wants to fly the F-16 back and ferry it home? And I’m like, Hey, you know, I know I’m going to fly to Spain, which is seven or eight hours, and then I’m going to fly from Spain to the US and what’s in between Spain and the United States, Rod?

Rod:     Is it a stream or is it a lake? It’s something very large, I know that!

Waldo:     The Atlantic Ocean, right? There are no runways, no emergency landing strips in the Atlantic Ocean. You’re up there. And so I said, you know what? I know this is going to be a challenge for me, but yes, I am raising my right hand and I’m going to suck it up. I’m going to face my fears and I’m going to do this. Put me in, Coach, I’m ready. And so the first leg of the trip, flying to Spain, seven, eight hours, it was kind of challenging since we had the Mediterranean Sea to fly over. It wasn’t too bad, a little bit of a challenge, a little anxiety, but I land and I’m like, okay, did it. Two days off in Seville, Spain, Saviah right. We’re sipping wine and having tapas and just traveling around. It was great. And so we had that for two days and guess what’s going through my mind those two days, Rod? What’s going through my mind?

Rod:    The transcontinental flight over a little lake, I guess, right?

Waldo:    Here we go. Okay. The crap’s going to hit the fan here. Let’s see how courageous you are, Waldo. You flew these seven or eight hour night combat missions, are you going to be able to fly over the Atlantic Ocean, Mr. Fighter Pilot, Mr. Courage-monger, right? And so that whole night before the mission I barely slept pondering the what-ifs. What if I have a panic attack and need to land? What if I bail out of the aircraft over the Atlantic? You know all those what-ifs, right? We’ve all been there. Didn’t sleep, got up the next morning with a terrible headache. I”m panicked during the mission briefing. I’m barely listening. All I’m thinking about this flight. I go into the jet, we crank up the engines and I say to myself, What the heck am I doing? I’m going to put my life on the line. I’m going to put the safety of my formation on the line because if I bail out, if something happens to me, it’s going to mess everything up. This isn’t war, this isn’t life or death. Must I go on this mission or is it just my ego getting in the way and trying to prove to myself that I could do this? And I said, as bad as it sounds, as embarrassed as I would be, I need to call on the radio and abort this flight and get somebody else in this aircraft and fly. And I call out on the radio and said to the flight lead, “2’s aborting” – I was number two out of the six guys in the flight. And he’s like, Why? State the reason. I said I didn’t sleep the night before. I feel like crap. I’m just not mentally ready. Which was true. I didn’t tell him I was claustrophobic, but everything else was true. And so we shut them down. We met back at the briefing room, we found another pilot to do the jet ,and three and a half hours later they were back in the air. Cost some taxpayer money while the tankers are waiting for us over the Atlantic, right. It messed some things up, but it wasn’t the end of the world. We got somebody else in there.

Waldo: Here’s my point – No one gave me crap about it. Everybody understood. They were disappointed. But hey, you know, Waldo, you did the right thing. And they got over it. But it took me years, years to get over the fact that I gave into my fear. I quit – really for the first time in my life. I’d never quit on anything. But I quit in that mission. And the lesson that I learned was this, and the lesson that I want you to learn is this – is that you can’t fly every mission. You can’t be Hercules, Superman or a superhero on every mission. There are times in your life where you’re going to need to say to yourself, it’s time for me to quit, to hang up the phone, to wait another day for the clouds to dissipate and the turbulence to go away and then I can get back in the cockpit and do it again. But quitting with honor means did you give it your all? Did you seek out the best? Were you prepared? Are you in a situation that if you quit, others are going to be truly negatively impacted by your failure? Are you so selfish in quitting that others will suffer because of it? That is not quitting with honor. But if you’ve thought about all those, if no one desperately needs you, if it’s not life or death, if it’s just your ego, then quit. But do it after you put in the effort and time to do the right thing.

Waldo:   And you know, if you back a dog into a corner and they have no way to escape, what’s going to happen? They’re going to jump and attack. If you back somebody else into a corner, you know there’s people out there who are committing suicide, who are massively depressed because they won’t quit. They don’t have an option to quit. And so I want you to realize that it’s okay to quit, but do it with honor. Ask for help. Prepare, try something new. You had to quit your job. If you’re an entrepreneur, I guarantee there are successful people here who are with a financial company or another group, and individuals and may be doing very well, successful and they can earn the money and you had to quit that job. You had to quit something in order to start something else as wel. So it’s okay to quit. Don’t buy into the philosophy of never quit. Sometimes quitting is the best possible thing you can do in order to get back into the cockpit and fly a mission that you believe in, that you’re passionate about and that’s going to help build more character and courage.

Rod:    I couldn’t agree with you more. And thank you for putting it into that context because to translate, you’re quitting a mission because most of the time for us as entrepreneurs, independent workers, it’s more ego than life and death. It just is. And we may think what we’re doing is quitting something that’s life and death. I remember I actually did not show up to a speech, a major speech in New York City, of all places, because I was on death’s door as far as being sick. At least I felt that way. And it killed me. My ego was killing me to not go. You know, to put it in context for listeners, you know what, life went on. I didn’t show up but I did quit with honor, and they got what they needed. But you know what ,the business went on. Life does go on when you sometimes need to not do certain things.

Rod:   But look, I know your time is valuable, Waldo, and I’ve got two more questions for you. The one thing – another story and I love these stories because they are lessons. This lesson I really enjoyed from the book and I find this ironic, this story, because it had to do with a mechanic and your father was a mechanic. So it’s almost going full circle here. And in our world we work and depend on other people, and I’m sure some of you and I have myself, I’m guilty of it, have not been as respectful for what maybe other teammates or folks I think should be supporting my efforts, you know, as I could be. And I’ve learned from those lessons and, Waldo, you shared a story about someone that you weren’t probably as respectful to, one of the mechanics, and what lessons you learned from that. So can you share that story?

Waldo:     Sure thing. So one of my last missions I flew in the military. Long story short, I cranked up the engine, it was shorted fuel, which would put me at a disadvantage. It wasn’t a big deal, but enough to cut the mission short. And we were doing an air-to-air training mission. I needed as much fuel as possible, especially if I was going after-burner and throwing fuel out the back of that aircraft through the much needed thrust. And I knew there were five hundred reasons why the jet may have been shorted because it was relatively common. But I blamed the crew chief. I chewed out that crew chief for slacking off and not double-checking the gauges, and I cursed at him. I was ticked off, disrespectful. I was just hardcore, right? And a lot of fighter pilots are hardcore, and I’m a New Yorker, in case you can’t tell from my accent, and I could just be brutal, right? And I just know how I am. I’m a lot different now, but when I was 28 years old or 32 years old, I just didn’t have that type of quote unquote relationship and communication training.

Waldo:    So I got back from the mission. Fuel wound up not being a factor, wound up beating the heck out of the enemy. I’m feeling like King Kong and I noticed my commander was waiting for me on the tarmac as I taxied into the hanger. Now in the Air Force, when your boss or commander waited for you at the end of a mission, that normally meant something was wrong at home. And I thought about my twin brother – was he sick, were my parents in the hospital – and I jumped onto the tarmac and he said, Come with me. And I knew it had nothing to do with my family.

Waldo:  And he basically said, look, Waldo, I heard about the conversation that you had with your crew chief. I heard about the choice words that you shared with him. I said, yeah, okay. And he said, you know how long that young kid was working on your plane? You know what he had to go through to make sure that the jet was mission ready and fueled up and the weapons systems was going well? I said, of course I do, sir. And he said, no, you don’t. You don’t know a damn thing. He was ticked off me and rightly so. And so then he said, I want you to go out and walk the flight line at 6:00 AM tomorrow morning and walk it with these young kids to see what they go through, the sweat and hard work that they do so you can do the coolest job in the world and fly the jet, fly the F-16 and be a fighter pilot.

Waldo:    And so that next morning I got up and I walked the flight line with these young kids and did inspections of the fuel tanks and changed tires and sweat with them. I’d never worked so hard on my life, honestly. It was brutal. And I didn’t have a clue what these kids did at the end of the day. And before that I didn’t care because as far as I was concerned, I was the captain. I was a fighter pilot, they were enlisted technicians who worked for me. I was cocky, had a big fighter pilot ego and I was wrong. And so what I learned, ultimately, was that everything I did in the air, up in the sky, had everything to do with what they did down on the ground, the hard work and attention to detail, albeit it might not have been perfect. And I went out and thanked the crew chiefs and I told them I appreciated them and worked on building that relationship with those unsung heroes who are responsible for making sure my jet was safely prepared for take off and to be mission ready.

Waldo:    And what I learned from that is, hey, there are a lot of other people in our lives who may be quote unquote technicians or non fighter pilots or administrators or IT professionals or contracts folks or people answering our phones who may not be on the front line like we are – the flight leads and fighter pilots of our business – but nonetheless, they truly are helping the mission – tightening down the rivets, fueling the jet. And so it’s always about for me, building an appreciation with those unsung heroes in saying thank you and noticing the good that they do and calling them on the phone and walking their flight line and appreciating all the different things that they do and I think in business, our independent contractors, our accountants, our vendors, the people who help us out, our spouse, our partners, the people who are just really out there behind the scenes helping us do our job. That is what really creates what I call a Check Six culture where you have each other’s back, where you’re appreciating each other and where you’re all willing to put in the hard work necessary to fly, fight and win for your company and for your team.

Rod:    Check Six culture, Waldo, I’m sorry, you just give me another question I had to ask. I believe I understand what that means. Check Six, Check Your Six – can you just expand that a little bit?

Waldo:    It’s a really important concept and it kind of goes back to what we talked about in the beginning – Never Flying Solo. So if you can picture yourself strapped into a cockpit, barely able to move, in this tiny cockpit with a helmet-mask on. It’s impossible for you, the flight lead, to see your most vulnerable position – behind you. You can see out front and to your left and right, but guess where the threats are coming? Where the enemies are coming? They are coming at your six o’clock – behind you – and you don’t know if you’re leaking fuel or on fire. But if you have a wingman or a wing ma’am, you know, at your left – at your nine o’clock position – or your right – your three o’clock position – if you can picture the positions on a clock, it’s easier for them to look over their shoulder and see your six o’clock, your blind spot. And it’s a lot easier for you to look over their blind spots, their six o’clock and call out threats and missiles and engine fires to them. So this concept of Checking Six is what creates a culture of mutual support. Calling out the blind spots. Telling them when the missiles are coming, telling each other often what you need to hear and not what you want to hear. Risking sometimes the relationship to do the right thing, to grab the keys from your wingman or friend, who if they’ve been drinking too much and are about to drive, to have the tough conversation with somebody who you care about to say, look, you need to work on your health and fitness. There’s a blind spot here you need to see, your relationships, how you’re communicating, right? And so those wingmen, and I mentioned this in the beginning, are the type of folks you want in your life who are going to tell you when you’re wrong and give you the feedback on growth, on cutting costs, on leveraging new technology and how to be a better communicator and build a better business in your life.

Waldo:   So find those folks who have your back. Don’t hang out with just yea sayers, who are going to accept you for everything that you do. Don’t hang out with naysayers, but don’t hang out with yea sayers, who, yes you to death. Find the folks in your life, your wingmen , via a mastermind or relationships that you’re building, who have the courage to really have your back, who care enough about you. And that takes time. You know, the biggest messages I can share with folks listening to this podcast today, is invest in that. Go out, volunteer at some nonprofits. Go to association events, volunteer to be on the board. Be the type of person that’s giving their wings away. That’s a trusted resource in your community, in your business world, and you’ll nurture those relationships with folks who will call on you for help, perhaps pay you for your services or refer you, and you’ll have other folks in your life who, when, God forbid, those missiles come for you, you’ll be able to say, man, I put in the work to build these relationships and now I need somebody to help me out, to give me an insight.

Waldo:   And you know, also, somebody that I can call who I can celebrate with. And you’re the type of guy, Rod, you know, getting to know you the last couple of years. And we invested in a mastermind group together, you know, you’re the type of guy that not only I would call for help – but somebody, when life’s going great, I want to call you, right? Hey Rod, just kicked some butt today. I got a brand new website, just closed this big deal, right? Think about those folks who can celebrate with you as well. It’s not all about the missiles, it’s all about the joy and blessings we get from being top gun entrepreneurs. You know, getting shot at sometimes and also taking out some targets and kicking some butt when we need to.

Rod: You’re absolutely correct there. One of the blessings I have is certainly your friendship. And Waldo I’ve got to end this by sharing with you that I’m holding something and I want you to tell us the significance of what I’m holding. I’m going to describe it for you and hopefully you’ll know what it is. It’s something you shared with me in Toronto, and there are words on it that say, prepare, engage, commit, trust, teamwork, and finally, of course, what I love, Push It Up. What am I holding and what does the Push It Up mean?

Waldo:   So you’re holding what’s called a Challenge Coin, and they’re called Challenge Coins in the military. Every fighter squadron has its own unique customized coin that has core values and the mascot, they’re always customed and you have to carry these coins on you 24/7 because you never know when your wingman or wing ma’am is going to call you to go to battle. And so they’re called Challenge Coins because if you’re hanging out at the squadron, at lunch, at the gym, at the bar, at dinner, and your buddy slaps down that coin and says Coin Check, that’s a challenge. Meaning you’ve got 10 seconds to pull out your coin, slap it on the table to show them that you’re mission ready and that you’re their wingman, that they can depend on you. Now, what happens if you don’t have the coin? You’re buying – drinks or lunch or giving to a charity, etc. There’s a consequence when you’re not mission ready, when you’re not their wingman in position ready to fly. But if you do have the coin, or the people that you’re hanging out with do have the coin, then whoever challenged them initially, then they owe everyone else a round of drinks or lunch or a charity. So there’s always a consequence and it’s a great way to build esprit de corps, and let everybody know on a moment’s notice many times and missiles and challenges are gonna come and we’re gonna need to strap in and fly and push up the throttle and dodge those missiles. So that coin is just a constant reminder of camaraderie and teamwork and the core values of commitment, trust, preparation, engagement.

Waldo:    And the last thing on there, like you mentioned, was Push It Up. And Push It Up is what we say to each other when we need to add power, need to go faster. And also when we’re committing on the target, committing on the enemy, where it’s go time, where we cross the forward edge of the battle area. We put our switches to master on hot meaning where things are coming off the aircraft and we push up that throttle and we break the speed of sound and we go after it. And that’s an analogy to life. When you hear your wingman call out the words, commit, commit – that’s what we say in combat – it’s time to Push It Up. And Push It Up is what I hope you will all do when you hear your customers, your coworkers, your family members and loved ones, say commit, commit time to Push It Up and to do that with competence means you’re prepared, means you faced your fears, doesn’t mean you’re fearless. It means you’re facing your fears.

Waldo:   Anybody that says fearlessness is full of crap. I don’t want you to listen to them because they’re not human. Your humanity means you must be afraid. But courage says, I’m staying in the cockpit. I’m responsible, I’m prepared. I’ve got teammates that have my back that I can call to for help. I am going at it. And when you do that as a top gun fighter pilot, a peak performing individual, when you understand what you’re fighting for and you love what you do, when there’s meaning behind the mission and you have somebody to come home to, to hug and the relationships in your life that mean something, that is what being a top gun wingman is all about and that’s what I hope for everyone listening to this podcast and what I continue to hope for you, my wingman and friend, Rod Santomassimo.

Rod:     Well, thank you, Waldo. Hey look, I can’t get enough Waldo and I know you’re saying that as well so where can we go or we get more Waldo Wingtips, where can we get more information? Help us out, share with us where we can get more of you.

Waldo:      Couple of things, if you go on my website, yourwingman.com, you’ll see a bunch of resources. My website’s got a ton of videos. You could sign up for the newsletter there. I’m @WaldoWaldman on Linkedin and Twitter and Facebook. I post something almost every day. If you have a question or comment, send me a note there or even email me at [email protected] I’d be happy to help you in any way I can. And then also, you know, I’ve got a free video series if you want to participate, you’ll get five videos from me talking about commitment and excellence and teamwork in your inbox every single day for a week. The best way to get it is if you take out your mobile phone and text the word topgun – one word, by the way, don’t separate them – it’s topgun to the number 44222 and put your email in, you’ll get a video series from me. You’ll also get some links to my social media and some other resources and that’s a great way to get in touch and get more of my juice. Get more of my fire power.

Rod:   Well, you know, I just dawned me after all these years of knowing you something I’ve never put together, I should have asked you and perhaps that’s a different episode, where Waldo came from, but there is a book, of course, What is it – Where’s Waldo? Is that the book? Is that correct?

Waldo:   Where’s Waldo, yep, the little guy in the red stripes ..

Rod:   ..and you speak around the world. So if I’m wondering where’s Waldo, where are you going to be next?

Waldo:      Right, so next week I’m going to be in Fort Lauderdale. I just came back from the Poconos working for a healthcare company and then I was in Baltimore working for another healthcare company. Next week I’m going to be in Florida working with Miracle Ear, you know, Miracle Ear. You see those commercials? A bunch of entrepreneurs who have retail centers and folks who are out there helping folks out who have some hearing issues and challenges, and their vendor suppliers are going to be there, their peers, their folks who are dodging them missiles dealing with Costco and all their big competitors. So that’s where I’ll be. And then after that I’m going to be back at your hometown in Greece on vacation.

Rod:     My hometown is in Italy, my friend. Actually, I’m half Italian, half Puerto Rican. So there you go.

Waldo: Oh, don’t mess with you. Yeah. And I speak all over, like I said, for entrepreneurs and franchises and financial services and Denver Broncos and all over the place. And if anybody needs a wingman to fly, hey, you know how to find me.

Rod:    Waldo, my friend, I can’t thank you enough. I know I will continue to Push It Up myself because of you and your kindness and your motivation. And I know you’ll do the same for our listeners. So thank you again for not only for your time with us today, but certainly we’re blessed for your service with the Air Force and what you’ve done for us and for our country. So thank you so much my friend.

Waldo:    You got it, Rod. God bless you as well. Take care.

Rod:    If you’ve enjoyed this great interview with Lieutenant Colonel Robert Waldman, you can find out more about Waldo at yourwingman.com. I’m Rod Santomassimo and thanks for joining me here on The Massimo Show. For more information about the Masssimo Group, please checkout massimo.coach. I’ll talk to you soon.

Hi, this is Rod Santomassimo President and founder of the Massimo Group. Did you know that for over the past 11 plus years, we’ve worked with thousands of independent contractors, solopreneurs, and small business owners just like you in repositioning their and/or their team’s efforts so they can build the personal professional practice they’ve always dreamed of. We provide coaching programs for all levels of experience, earnings and, yes, success. So if you’re finally ready to get off that transaction treadmill and chasing deals that are growing nowhere and start building the personal professional business and life consisting of greater wealth and more time, well, check us out at massimo.coach. That’s massimo.coach.




Lt. Col. Rob “Waldo” Waldman

Hall of Fame Keynote Speaker, leadership expert, executive coach and Decorated Fighter Pilot, Waldo leverages his real-world business acumen and experience leading diverse teams in the military to help leaders overcome obstacles, break performance barriers, and maximize team performance.

For a free copy of Waldo’s audiobook book Never Fly Solo and the 5-Video Top Gun Mission Ready Leadership Program: If You Want To Find A Wingman, Be A Wingman, text Wingman to 44222.




  • How to deal with rejection (from the Air Force pilot who’s scared of heights)
  • How to put yourself in the cockpit (and get shot at)
  • Identifying who has your best interest at heart
  • When is it ever okay to quit (and how to quit with honor)