Matt Baiamonte Interview

Welcome to Business Outlaws. So it’s me, and it’s Big Mike of Advanced Nutrients…and our host, the infamous Jayme Fox. Each week, we invite the audience to listen in on our business strategy conversations with the bigwigs—with self-made leaders who are breaking the norms of average performance in business and in life.

You get to be the fly on the wall, behind closed doors.

We recently sat down with world-class boxing trainer Matt Baiamonte (his last name’s Italian, apparently). His mentor was Angelo Dundee, who trained Muhammad Ali. Angelo always told Matt that you have to treat everybody differently. Every fighter’s different, because every person’s different. So you really have to get inside their heads and see what makes them tick.

Matt and I met because, for at least six months, my pal Big Mike was like, “You gotta go, you gotta go meet this guy.”

Boxing is the best high-interval intensity training in the world. 13 rounds, one minute of rest, and three minutes of go time. And let me tell you, when you’re throwing punches and dancing around the floor, it burns calories. Besides swimming, it has to be the toughest sport to condition for. And, as Matt will tell you, boxing has been the number one sport for the last 50 years. Nothing will beat it.

I’d been boxing. Training. And listen: It was already one of the best things I’d ever taken up. Just doing the pads and the heavy bag…

But Mike kept telling me, “Chris, you gotta go meet this Matt guy—Trainer to the Stars.”

And Mike was right. I texted, and “Matt, Trainer to the Stars” came down to see me one day at last. When we were done, I was completely drained—just a pool of sweat. Because you have to use your mind and your body. Your concentration level is crazy—you’re slipping punches, blocking punches, trying to figure out where you have to hit…Until working with Matt, I had no idea the sheer level of concentration it takes to box well. It’s really…intense.

Matt has trained so many successful people. And that’s why he knows a lot about performance and leadership. He had amazing stories and insights to share with us on the show. There was so much he had seen and trained—both the good and the bad.

He wouldn’t comment on whether Mike and I were good, or bad, but that was polite of him.

Instead, we focused on dedication and determination.

We coined him “Big Daddy Matt” to match up with Big Mike, and we dug into what makes a fighter truly dedicated and determined. Turns out, Big Daddy told us, there are basically three commonalities he sees:
1) Leadership Mindset
2) Questioning Everything
3) WWW – A Willingness to Work on Weaknesses.

Matt has trained LeBron James, Dwyane Wade, Chris Bosh, Brandon Albert…

Antonio Brown, Mike Wallace. Even Dan Auerbacher, from the Black Keys…

He trained Matt Damon for Bourne Identity. He’s apparently not good and not bad—but great.
Matt and Matt have actually trained six movies together.

Big Daddy’s also trained IndyCar driver Carmen Jorda and MMA fighter Erin Toughill, who was on Mike Tyson’s last fight. They were the co-main event in Washington, DC.

So, enough of the bragging—but with this guy’s resume, having worked with world champions in all walks of life, I wanted to know what makes them champions. And first, to Matt’s point about treating everybody a little bit differently in order to get inside their heads: I wanted to know if top performers are supposed to get special privileges. I mean, everybody’s got their things, their little quirks. Should people who do more or sell more get away with more?


There’s a place in Florida Matt used to go to get clients called Bommarito Performance Systems. Three to four hundred future NFL players would pass through there every year. One guy who Matt ended up training was a great running back. But he would literally go in to the club and just stir shit up—he’d show up late, be boisterous. And the owner was like, “You can’t come in here anymore.” No matter how good you are, you’ve got to have a sense of leadership.

Big Mike agreed. He recently got rid of one of his top sales guys, just because he was a shit-stirrer. There was no room for it. And those people, no matter how good they are…They’re not going to be a Jerry Rice. A Michael Jordan. Michael Jordan would try to get his teammates to perform. And even boxers in the gym—even though it’s not a team sport, there’s a way to behave. There’s a mindset and attitude that rubs off on the younger fighters. There’s how you should behave and how you shouldn’t behave.

So I asked Big Daddy Matt more about the Michael Jordans of the world—LeBron James, or even Dan from the Black Keys. What’s their work ethic like? Can you see the killer instinct in them?

There are obvious marks of dedication, Matt told us. LeBron trains seven days a week, and Dan finds a boxing gym in every city he travels to. And Dan even trains on the days of his concert—he leaves the gym, goes straight to the concert after, and performs.

Those are the types of people who are successful. Those who want to put in the seven days, who don’t mind doing a workout before a concert performance in a stadium of 40,000 people. They’re on stage giving everything they’ve got, and they still come in for an exhausting workout. So determination is obviously part tenacity—an unwillingness to give up.

And dedication comes from that determined mindset. Our best fighters lead the way with dedication, which turns into discipline. Muhammad Ali’s discipline was second to none, Matt told us. First guy in the gym, Ali—last guy out of the gym. And he lived in Overtown. So the ride from Overtown to the Fifth Street Gym was three or four miles. Ali would run to the gym, do his workout, and then run home.

Discipline is part of a leadership mindset. Mike Tyson, bless his ear-biting soul, was also a leader in the boxing world. He would learn his combinations from his coach, and then he’d pick one particular combination that he wanted to work on. And he would literally sit there for 30 minutes, maybe longer, after he was done with his overall training and work on that one combination, over and over and over.

A leadership mindset is what separates a champion from a contender. And the same goes for the president or CEO of a company, versus someone who is just an employee their whole life long.


But there are less obvious qualities of being a champion. Things that might not scream “warrior mindset.”

Matt pointed out that most of his most dedicated and determined fighters, from all career paths, ask a lot of questions.

They don’t just sit there and take instructions. They don’t say, “Okay.” They question their coaches, they question their bosses to see how everything works. They even question Big Daddy Matt.

Even if you’re a genius, like Big Mike, you should ask a lot of questions with the intention to understand. In fact, I find that Big Mike swears by this. While most people ask questions with some kind of agenda in mind, Big Mike’s only agenda is to understand the answer before he has an opinion. This aspect of dedication is a gift—for everyone around you, and for your own progress.

Mike is constantly questioning Matt, like “What punch? Why should we do this? Why should we do that?” And according to Matt, that’s the sign of a person who is, or is going to be, a champion. Because if you don’t ask questions and you’re not afraid to get outside of your comfort zone and look foolish, you’re never going to get anywhere.

Matt was kind enough to say I’m like this, too.

It all circles back to the ego. It can help to have a little bit of one. The place where you have to have it is in knowing what you do best—what your thing is. Like when it comes to cannabis, Mike has a pretty healthy ego. All right, he has a really big one, because he’s Big Mike. He knows how good he is in that sector.

But about things other than cannabis—when it comes to learning something new—Mike puts that ego on the shelf. There’s no room for it in Learn Mode. You have to know the difference—when to apply it, and when not to apply it.

So it can also help a lot to put your fucking ego away. Ego really, really just gets in the way of your learning.

Mike said he realized this later in life. After he died on the operating table.

You can realize this and work on asking more questions before you’re on your deathbed.


Matt talked more about how his fighters let go of their egos by using me and Mike as an example: Say Mike and I are fighting, and Matt is in Mike’s corner. Mike goes out there for the three minutes. He does his thing. But for that one minute when he comes back to the corner, he’s got to lose the ego and listen to what Big Daddy Matt has to tell him. And he’s got to have faith in him—because if he doesn’t have faith in his coach, he’s not going to be successful.

Even if it’s with your president or your employees, you’ve got to know when to let go of the reins and when to grab hold. And this has everything to do with being aware of your weaknesses.

If you have a weakness, admit to the weakness, and then, get help to fix it.

When we talk about working on weaknesses, I think about the importance of figuring out ways to hijack the skills and knowledge of other people. You need to surround yourself with people who will compensate for your shortcomings.

I asked Matt if Muhammad Ali had a weakness.

Matt replied: “His ego.”

“So how did he counteract that?” I asked.

And Matt explained that Ali didn’t really want to be taught. Muhammad thought that he knew everything. So Matt’s mentor Angelo had a little mind hack he figured out for Ali’s jab. Angelo kept telling Ali to snap the punch. “You need to roll the thumb over, and turn the hand,” he’d say. But Ali wouldn’t do it. He just wouldn’t listen to Angelo.

But Angelo knew that everyone thinks differently. And so, you have to be able to teach differently.

So one day Angelo comes into the gym, and he comes up with this brilliant idea. He tells Muhammad: “Man, your jab is so great. The way you roll that thumb over and snap that hand. Can you just show me how to do that?”

“Yeah,” Muhammad says, “I’ve been doing this since I was a kid.” And Angelo’s like, “Bullshit. Fucking told you last week to do it. You wouldn’t listen!”

So Angelo started training Ali by maximizing on his biggest weakness: his ego. When he wanted to get him to do something, Angelo would make Ali think that he was teaching it—and that was it.

In this case, we’re not applying the notion of being self-aware, but Ali’s mentor used the same access point we can use on ourselves: weakness. Weaknesses are strengths if you can harness and master them…and if, in one way or another, you can accept the help you need to improve your skill.

In Matt’s experience, female fighters have a little more patience for improving their weak spots. And because of that, they seem to learn a lot more quickly. Us males—you tell us to build something, give us the instructions, and we’ll throw the instructions in the trash.

Meanwhile, women will sit there and read every single thing, and then put it together within five minutes. And the guys will still be sitting there drinking beers like, “We’ll get it in an hour. We’ll get it, we’ll get it.” Then afterwards, there’s 20 forgotten screws left over.

But champions—of either sex—will take their time. And actually, Matt told us, that’s how Angelo first got Ali as a client. Angelo was underpaid and overworked, and when he interviewed for the job, they said to him, “How quickly can you get Muhammad to be a champion?” Angelo paused and said, “I’m not going to guarantee you guys a time. It takes time. It takes effort. It takes patience.” They hired Angelo on the spot.

So what did we learn today? Other than that Big Daddy Matt is the Trainer to the Stars?

We learned that everyone thinks differently, so you need to be able to teach differently.

We learned that dedication means doing sit-ups until it hurts, then going to perform your concert. That a Leadership Mindset makes way for that kind of discipline.

We learned that Asking Questions shows your work ethic, not your inferiority. Not to be afraid.

Ego. We learned that you need it, but sometimes, you need to put it away.

And by getting in touch with your WWW—a Willingness to Work on Weaknesses—you can develop the patience you need to achieve success. That is, if you’re willing to get the help.

For more of this and other insider convos, make sure you subscribe to the Business Outlaws podcast. We’re not going anywhere…so listen in.

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