HI 152 - From Sea Level to C Level with Whiz Buckley
7 Dec 2025 · 28 min
This is the transcript of Heroic Investing Show episode 152, featuring Whiz (Matt) Buckley in conversation with hosts Gary Pinkerton and Jason Hartman. Whiz recounts his Navy fighter-pilot career, his rapid mobilization and actions on September 11, 2001, the sudden loss of his American Airlines job post-9/11, his move into business consulting and later to options trading and founding Top Gun Options. He discusses translating military practices (briefs, debriefs, accountability) into corporate leadership and training, his book From C Level to C Level (also referenced as From Sea Level to C Level), and points listeners to topgunoptions.com and go.topgunoptions.com/sitrep for resources and a daily market video.
Questions this episode answers
Episode 152.
September 11, 2001 (the morning of 9/11).
topgunoptions.com (and go.TopGunOptions.com/sitrep for the daily market sitrep).
From C Level to C Level (also referred to as From Sea Level to C Level).
Chapters
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Hello and welcome to episode 152 of the Heroic Investing Show. This is a podcast for first responders, members of the military, veterans and anyone looking to improve their financial future, gain some freedom with their time. So what does it look like when we leave the military? And when's the right time to leave the military? Well, we try to solve that and I think today's interview with Matt Wiz Buckley is a good one. I think it gets us far down that path. So Wiz was a Navy fighter pilot Right around 2000 and well, 9 11, immediately before 911 he tells a great story about his history and how he ended up doing what he currently does, which is teach corporate America the lessons of the military on how to improve their organizations, how to get a vision, how to work efficiently, how to have an organization that's all moving in the same direction. And like I said, get efficiency back. He's been wildly successful about it and he's written a book from C level sea level to C level as in corporate level. So from C level to C level. And please go check that out. You can get it at Amazon. He very graciously sent me an autographed copy. It's an awesome book. I really enjoyed it. Hey, my favorite part about it, Wiz, if you're listening in, is that you chose to put an appendix in. And. And the only thing in the appendix is a message to Garcia. And that is an amazing motivational story. Had to memorize it at the Naval Academy and it has done wonders for me. My kids, I will admit, hate it. They hate the idea of a message to Garcia. They come and ask me something and I say, you remember a message to Garcia? And they just look dejected. And walk away. But it's starting to rub off. I think my teenagers are getting it. So this interview with Wiz is awesome. Back to how he ended up doing what he did. Well, I won't ruin the podcast episode for you, but right at the time of 911 he was headed off to do what a lot of military pilots do and that was become an airline pilot. His timing was amazing. They were hiring like crazy. Everything was perfect. But you also remember what happened in 9 11. His story is much better than just those that thought they were going to be a pilot and ended up getting furloughed. His is very exciting when you talk about what he did on 911 and what many other patriots did on that day. Most of us who are in the military, or at least were in the military at 911 remember every bit about what they did to try to help serve and combat that at the time, invisible unknown enemy. It was crazy. And all of us have a story that we'll never forget about it. Wiz's is really good. You know, he's a very typical extrovert Navy pilot and somebody that you're really going to enjoy talking to, hearing from. Please reach out to Wiz and get a copy of his book. I think you'll really appreciate it. And if you're running a company out there or thinking about running a company, or you're just a veteran like myself and a first responder looking for what it would be like to jump and looking for somebody who can help you out with that. No doubt Wiz will talk to you. You'll enjoy the conversation and you'll come away a little bit more energized than you were before. Hey everyone. My distinct pleasure to bring to you, Wiz Buckley, Matt Wiz Buckley and the author of From Sea Level to Sea Level. You're gonna love this one.
Short story long, when I got off active duty in 2000 to go be one rich airline pilots, I literally got the lottery ticket. I got hired by American, moved to Fort Worth and also got hired by the Hunters strike fighter squadron 201, which was a reserve Hornet squadron. So that was the stereotypical hit. The lottery ticket. Well, not really because the morning of September 11, 2001 was supposed to be my first flight from Dallas to Miami, Miami to Cancun as an American Airlines pilot. My wife came in and said, I'm packing and I still it's in my guest bedroom. My American Airlines uniform is still in the plastic. I never. She said, you better come out and see the tv. And I Said, whatever, I'm packing. She said, no, no, no. Somebody hit the World Trade center. And it ain't a small airplane and it ain't bad weather like you said. So I go out there and I see, you know, big smoke and hole, beautiful day. And as I'm going through my mental aviation checklist to how that could have happened, you know, boom. Second plane hits. Yeah, immediately. Immediately knew we were under attack. Ran into the bedroom, pushed the plastic, the uniform out of the way. Threw on my flight suit, didn't even tie my boots. I almost broke my neck running out of the house. I had an old 89 Porsche. I think I was 130, 140 miles an hour out to the air, down. I think I broke the land speed record. Got out to the air station just as they closed it and went to. Was it Threadcon Delta? They closed the air station and I made it out with one other F18 buddy of mine, Gruff and Lieutenant Commander McGrath, also an American guy. Next door was the Tang, the Texas Air National Guard, the spads, they flew S16s. We called up and they said, hey, man, get over here. We got four of our guys out here, and their command post was tied into norad. So they had a Brigadier general there. And as we ran over there, we stopped by maintenance control. We told the chiefs, chief, what do you got? He's like, sir, we got four jets. I said, get them up. The Air Force is going to give us some missiles and some bullets, get them ready for combat. So we went over to the Spads. We briefed to start flying a combat air patrol, four S16s and two Hornets. And as we're sitting there briefing, the Pentagon got hit. It was surreal. So I went from possibly flying in an airliner that day to shooting one down to maybe even shooting down a squadron mate. Because, I mean, even our skipper, he was a Delta guy at the time. Everybody was airborne except for a couple of us. You know, imagine being ordered to not only shoot down an airliner full of your countrymen, but, you know, one of your bros that you flew over Iraq with. So it was surreal. It was crazy. The next couple days were just a blur. I remember coming in the next day, September 12, and reading the ATO, the air tasking order for the United States. The only time I read an ATO was in the Persian Gulf. And it had the rules of engagement and fire. Washington, New York, free fire zones. It was crazy. What I'm getting at is since I was one of the most junior guys at American Airlines, a week Later I got like a. When I got hired by American, I got a colored stationary and signed by the chief pilot in ink. You know, welcome aboard. And you know, a couple days later, I get this photocopied letter, like off centered, from American Human Relations saying, dear crew member, you're furloughed. So in the blink of an eye, I hadn't had a lot of money saved up. We lived in base housing. We used it to buy our first house. That was it, man. Lost my health care, lost my pension, lost my career. In the blink of an eye, we lost everything. So you got to scramble. My wife was. At one point, she was waiting tables at Buca di Peppo in South Lake, Texas. But I started to apply myself to my trading even more. It was kind of a hobby in the background. Now it was go time. Fortunately, I could go into the squadron and reserve bum. And we actually ended up getting mobilized for Operation Iraqi Freedom. So there was 3,000 other Americans who even have a life anymore. So I stopped feeling sorry for myself and scrambled. But what happened, Gary, was I started doing some business consulting. I started going into businesses and just teaching them that the stuff that we all think is like breathing, like debriefing or contingency planning or. So I did some business consulting. And as luck would have it, one of the events I did ended up being for one of the largest options trading firms in the world up in Chicago. So on the briefing call with this company, they're like, well, you know, we're an options firm. And an option is. I'm like, I know what an option is. I'm in an apple long call diagonal, and I'm short Amazon right now or whatever. And they're like, oh, my God. So I ended up going up and doing this like two day event, business consulting event. And I must have snowed them somehow because they were very impressed. And they went mafia on me and made me an offer I couldn't refuse. I swear to God, I felt like Valentine in Trading Places. I mean, I. Here I am, this little retail trader, and they asked me to come up and essentially help run the place. So did that for about three or four years. And no offense to anybody from Chicago, but I ain't a Chicago. The people are great, the food's good, but walking from Union Station to the Board of Trade in February is like a survival situation.
Yeah, that is seriously cold. I grew up near there.
Oh, yeah? Yeah. We lived out in Naperville, Napertucky. So at that point, I'm like, you know what? I Dragged my wife to some pretty crappy Navy bases. She was from Boca Raton, Florida. So I said, you know what? I think I can do this on my own. So I always had the idea kind of running around my head, like, why don't I just teach people how to do this? And we moved down here to South Florida, and eight years ago, I started Top Gun Options. We teach mom pop, stay at home moms, you, anybody, how to trade equity options. So it's been an interesting journey, to say the least.
Wow.
Yeah.
That is incredible. How do you transition that? I mean, you don't want to spend time in Chicago. You love trading options. You love the aspects of that. So how does that land you into starting a business like that?
The consulting business was kind of the end. Like I said, the speaking.
Yeah.
I mean, right now I have tons of buddies who have their own individual companies. You know, from Ex Operator, you know, I got a lot of SEAL buddies, fighter pilot buddies, who are doing just do this business consulting. All the stuff we take for granted, even in the, you know, the submarine for you guys. Hey, we're going to do an exercise. We're going to brief this exercise. We're going to have what are called spas, single points of accountability. We're going to debrief after this is over, and we're going to, you know, we're going to call it a nameless, rankless debrief. We're going to get in a room, we're going to take our name tag off, our rank off, and we're going to rip each other apart to make us better. Door opens up, we're all best friends again. So all this stuff I applied to the business world, and I got to be honest with you, I'm a lot of the consulting. I just did an event recently for a big biopharmaceutical company, and I'm sitting there with the heavies, and at one point, I looked at him, I'm like, you guys make money in spite of yourselves. I'm like, this is a complete clown car. Because in the Navy, Gary, if I told you, hey, man, I need you to do this by next Friday, if you said three words to me, I got it. Guess what, man? In my mind, it's done right.
Right.
In the business world, I found out, hey, Gary, can you do this by next Friday, two Fridays from now? I found out you didn't do it. There was no way in hell you were gonna do it, and I ended up doing it. So the accountability and a lot of that stuff you go into companies and try and even if they take 10% of what I say, it improves their execution like you wouldn't believe. I mean, companies don't debrief. And if they do, here's the funny term, they call it a post mortem. I'm like, who the hell wants to go to a post mortem? I think I'm going to go to one in my life and I'm going to be dead for it. So it already has this negative connotation. So that's how it kind of lended itself, was me going into companies and seeing that. This is. I can't believe you guys make money and helping them get better. And then kind of as I was doing all that traveling, literally around the world, Brazil, Thailand, I've given keynotes or done business consulting around the globe. But in the same time, in the back of my mind, I'm like, my passion really is teaching people how to trade. Because after being on Wall Street, I gotta be honest with you, they almost make it seem like it's so hard or we're the smart money. Those people put their pants or dress on the same way we do, man. And there ain't nothing. If I can do it, anybody can do it. That's the other thing about Wall street that I couldn't stand. When somebody made it on Wall street or made a lot of money or got promoted, they pulled the ladder up. And as you know, in the Navy or the military, man, when you make it. When I went to Top Gun, I didn't come back to my squadron with all this knowledge and then just be Mr. Wonderful. I stood in the ready room and for weeks gave lectures and I accelerated everybody's experience. So when you make it in the military, you put the ladder down, you help your buddy up, you put your arm down. So my time on Wall street wasn't pleasant. I mean, there was nice enough people, but at the end of the day, it just. It wasn't a squadron, man. So Top Gun Options, it is a little bit more of a squadron. We do live events, like twice a year when I meet the members and stuff, and it's as close to the squadron as I can get. And the trading, when you think about it, and our motto is trading is combat. Because when you think about it, in a trade, somebody's going to win and somebody ain't. So why wouldn't you use the same methodologies and techniques that we use to win in the military in trading? So I owe it all to the Navy, and I essentially copied and Pasted Navy flight training, a primary, intermediate, advanced. And then I just kind of put the different options stuff in there, because, as you know, I mean, primary flight training in the Navy, I literally had a guy in my flight school class whose first flight was to flight school in an airliner. I think he went to school in Wyoming or something. I mean, he had literally never. And in six months, this dude's flying off the pointy end of an aircraft carrier. So the military training programs are designed for a reason. So I owe all of this to the Navy and the military, and I just kind of put a little different bow on it, to be honest with you.
Yeah, yeah, I've seen the same thing. I'm helping a friend who's got a great company, but their training for the pointy end of the spear, people who I'm proud to call myself one of, is not great. You know, and it was great while he was doing the training, but then kind of when it handed off to, you know, other individuals would run it as the company got bigger, it's really just falling apart. And they just don't have the focus on training people the way we do in the military. And it's so easy. Right? Like. Like I mentioned, you know, one thing that would be very vital. I'm being very. Just tiptoeing around because it's not my company, and he didn't hire me to come in and drop a hammer yet.
So it's like, one of the things that might be really good, I'm suggesting this to the head of operations, is maybe after the person gives training, or maybe you have somebody check their abilities before they go give the training, and then afterwards, maybe you spend a couple minutes and give them some feedback about how it could get better, and they're like, oh, my God, that sounds awesome. I'm like, I just can't. It's hard to believe, you know, with it being so ingrained in us for two decades that that's just not obvious to other people. But, like, I say the word hilo to a friend, and they're like a.
What?
You know, So I have to remember that a lot of this is just our language and our culture. But. But you're right. It's not hard to adapt. And I think for the audience out there, it's just a really great way. Just another great reminder. A good example for how marketable and valuable they are. You know, I had a great guest on recently who just, you know, said kind of the obvious, but it's nice to hear it, and I Got a lot of feedback from listeners. That, man, I was really glad that he said that, you know, gave us confidence. And really what he said was, listen, just the fact that you're in the military, a lot of people think that, you know, our skills are not translatable well out into the real world. He's like, but just the fact that you get up on time, you showed up to work on time.
Correct.
You know, he's like, and your home life is put together, so you've married a spouse that knows how to do stuff without you around. He's like, actually, your skills are that they're not whether you know how to weld correctly or not.
That's exactly right. Even if you don't know how to weld, you can be taught. That's the good thing about the military background, is you're teachable. Every executive that I've talked to or worked with, they say they love hiring veterans because it's the intangible leadership qualities that we have. I mean, I remember getting to my first fleet squadron. I'm like, hey, man, where's my Hornet? And the skipper's like, yeah, that's your fifth responsibility. You're the avionics division officer. You know, that sailor's under arrest. This one hasn't paid child support. You know, I'm like, holy crap. I'm like, I'm in charge of 22 sailors with 20 and two chiefs who are my dad's age who were, like, sailing off the coast of Libya when I was playing soccer when I was a kid. I mean, so you're thrust into a leadership role, and businesses would rather have somebody who can be a leader than somebody who knows how to weld really well. I can teach you how to weld really well.
Exactly.
So that's the intangible. The one drawback, and it's sad to say, is we have to throttle back a little bit in that transition from the military to the business world, because some men and women I've tried to help, they're frustrated because they do get to a bit. I'm like, hey, man, it's almost like, I don't want to tell you this, but I have to, for your survival, throttle everything back by about 50%. Because if you're in a business meeting going, are you kidding me? We're not going to debrie this. And Steve, Steve, everybody knows you gooned up on this project. Are you not going to admit? I mean, it can get pretty ugly. So you have to tread lightly, because I've seen guys bottle rocket out pretty quick in the business world because they're just stunned that like I said, some of these companies make money in spite of themselves. But if you pace yourself and kind of release your military knowledge and coolness at a good clip, you'll do great.
Yeah, no, that's great advice. And the other thing that I've learned is that it takes a softer skill I think is really what you're see, you know, a softer approach to people. But I find it that it makes me elevate my game. Not really so much, you know, initially like your, your way of interacting with people, just slowing down your response time. That is certainly a throttle back. I think it actually makes me perform at a higher level because these people don't have to do this. Right. It's not, you know, it was very easy for me to tell My crew of 150 people what to do and I didn't care so much whether they liked it in some cases. But. But that's not true when you're in an all volunteer world. Right? And in reality, on my ship, I was in an all volunteer world too. They could, I mean, they may not be able to walk till after the contract, but if I want to retain young officers and like you said, I want to pay it forward and have somebody replace me who's competent and the top of his game, you don't want to be washing those people out with bad leadership. So it's somewhat similar. But you know, again, in this company that I work with, just Paradigm Life, which is an awesome company, but all of us are essentially independent business owners that work together collectively towards the same goal and none of them have to stay right. So to build what we want to build, it's got to be win win. And I think that's actually harder. But you're right, it's a whole lot different.
It's so true, man. And it's sad. But if businesses executed the way we execute the military, I mean our economy would be going through the roof. But you know, no matter how hard we try, businesses are still businesses. And you nailed it. Walk with a little softer touch than would.
So I was just going to do a little bit of transition here, but it's not that much. I was reading a fascinating thing about how many Marine leaders, Marine Corps leaders succeed as CEOs and presidents of companies in America. And it's been that way since the 1920s or 30s. And having had the opportunity to work with a lot of Marines. And the reason I'm circling this in is because you come From a Marine family.
Right.
And you just mentioned to me that your son wants to be a Marine.
Yeah, I dropped him off Sunday up at Norwich University in Vermont where he's in the Corps of Cadets. You know, I jokingly say, I guess I dropped him on his head because I was a Navy fighter pilot. He wants to be a Marine fighter pilot. So he plays hockey. It's a great Division 3 hockey school. But I know he's doing a little to razz his old man, but he growing up, he always kind of looked towards. Because I did a three year tour in Marine in a Marine F18 squadron in a year in El Toro before they closed it and then down to Miramar. So, you know, he was born in Balboa Naval Hospital, so I have a lot of very close friends that are Marines. Actually one of my Top Gun options members, I went through Top Gun with him and he's, he's going to be the skipper of VMX1, which is the Marine Test and Evaluation Squadron. So he's going to get to fly the JSF and Hornets and stuff like that. So he always, you know, looked at the Marine Corps as a little bit more elite and stuff like that. So I couldn't be very proud. Father moment. Yeah, absolutely.
Yeah.
So that, I mean, I think that's why Marines are such great leaders out.
In the, in the real world.
And then I'll stop my love affair with Marines here. But, you know, as I was getting ready to leave the Naval Academy, I was, I was torn between Marine Corps and submarines. You know, both of them have Marine in them, but that's about it because, I mean, they're totally on opposite end of the spectrums. But what I liked about both of them was the small unit cohesive camaraderie that's there.
Right.
Esprit de corps, they call it. And the same things there in submarine force. And everyone walks around with a chip on their shoulder. It's not because of our abs, sadly, in the submarine force, but they're both small unit communities doing stuff that most people wouldn't do.
Tight, very tight knit.
Right. And I think that's when you bring that to a company, you inspire people, you raise a culture of, hey, you know, that might be okay for the competitor, but we're better than that, you know. And so I just think that that stuff comes from anyone who's been in the military who understands camaraderie. And winning doesn't come from burning the people below you, you know, it comes from inspiring them. And so many great leaders have come with that inside them.
It's interesting you bring up the Marines, because here's the deal. Their cohesion, it really comes from the fact that they're a Marine. He could be an aviator. You can be an artillery. You can be a lawyer. You're not. You're a Marine first. You know, whether it's going through Parris Islander, when Matthew gets commissioned, he's going to tbs. Man, you go to TBS for six months before you get near a helicopter or a jet. So it almost starts in that it's a unit cohesion. And, yeah, it takes a different type of person to be kicking down doors in Fallujah, man. That. That's. Yeah, you get pretty tight with those folks, you know.
Absolutely. You know, and, you know, circling back to what you said about, you know, when you go to your squadron and looking for the jet, you know, same thing, right? We're a Naval officer first, we're an Air Force officer first. Or, you know, a member of a squad, enlisted member of a squad. But that's not reinforced as heavily in the other services. And so we could certainly do a better job. But it's all there, and the basics are there. We've kind of gotten away from it, you know, when we consider ourselves a technical expert at some.
Now I got to make fun of the Air Force. I mean, they're barely on our side anyway. But I remember I'd go in to fight, you know, an Air Force squadron, they have a lot of officers, man, running around like the voting officer, the weather officer. I'm like, hey, man, in my fleet squadron, I'm seven officers. Well, that goes back to the Navy and the Marine Corps. On, look at you, man. On a boat, there ain't that many spots. So whether you're on a carrier or a sub or even in a Marine unit, there ain't that much room. So we don't have nine extra officers to take care of all of the ancillary duties. You are the ancillary officer, so to speak.
Right.
I like to razz my Air Force buddies about that. And begrudgingly over maybe their fifth beer. They'll admit that, but they actually kind of rub that in their face. Like, wouldn't you rather have just been a pilot for your entire Navy career? I'm like, yeah, and no, man, I enjoyed. I have sailors that I still keep in touch with. All those life experiences. And another subtle dig at the Air Force when they transitioned, they didn't have that. Everything you just said, they were only a pilot, and they weren't the maintenance, they have their own maintenance squadrons. I'm like, I was the maintenance officer. I had 220 sailors and marines under me at one point. So I love our sister service. I'm just giving them grief. But they're. I will say the Navy and the Marines are a little more elite. I'll leave it at that.
I'll let you drop the mic on that one. So how can they find out more about your company, about trading options if you want, or just about. You've written a couple books, kind of pass that to them.
Yeah, if you head to go.TopGunOptions.com book you'll see the book I wrote and you'll also. There's a bunch of speaking clips on there. An example of me, I think. Yeah, it was McKesson. McKesson's the what Fortune 7 company. And actually I'm on stage with John Hammergrin. He was the highest paid CEO last year. 145 million doll bucks this guy made. I'm standing on stage, I'm like, dude, you got 50 bucks I can borrow? But yeah. Go.TopgonOptions.com book and the book I wrote is called From C level to C Level. I actually came up with that and that's CA level. It's catchy. It kind of hits everything we talked about, man. Each chapter I give business and military examples. It's a pretty cool book. But if you're interested in learning how to trade options, man, just go to the main page, topgunoptions.com and you can scroll around there and find out stuff. I do a daily market video. Most of my members call it a rant because I get going especially with what's going on now in the country and everything like that. You head to go.Top GunOptions.com sitrep and that should sound familiar to us. I call it the Market sitrep. So it's my daily. It's a free video, just name and email and it gets pushed to you daily when I shoot it. So go.TopgonOptions.com book and if you order the book on there, I sign it. I'll put it in the mail today. I'll sign it to whoever and I'll send you one too. Gary throw it in the mail for you. Options trading topkinoptions.com and then if you want that daily sit rep, it's go.TopgonOptions.com sitrep.
That's awesome, Wiz.
Well, thanks so much.
You've been very kind. Sharing a lot of Time with our audience here today. Any parting shots?
Man, I think this is the most I've talked to a submarine guy in my life. You guys aren't that bad. Gary, you'll find this funny, man. We were doing RIMPAC, whatever it was 96. We were the orange for whatever. There was some sub out there that was still not sunk yet. We're coming into the break overhead the Kitty Hawk and I look in the wake and there's three miles behind the ship. I'm like, whoa, hey man, look at that whale. And my lead's like, no, dude, that's it. Was this whatever. The USS whatever was like in the wake of the Kitty Hawk trying to take pictures. And I said, hey, boss, the air boss. I'm like, I think there's a sub behind us. He's like, what? They suspended flight ops and sent the, you know, the helo over and drop zoned it. Yeah. So apparently they were. The subskipper was too busy taking pictures or something like that that they didn't get a torpedo shot off. And allegedly we shot him before. So I got. I got like the Admiral the next day on like the ship's TV was like, they called our squadron VSFA 94. We put the anti submarine in there. So nice. The only. I think that was the only sub I've seen in my life, man. But no, thanks for your service. It. It was a pleasure talking to you and looking forward to hearing from your folks if they have any questions. Gar, that's awesome Wiz.
Well, we will be in contact, man. Thanks so much for joining us and getting your shots into the submarine force.
All right.
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