The squared circle has been a big part of my life since I was 19, which is coincidentally around the first time I started to think about my career. Boxing is my muse; it always pulls me back in. It’s a passion I haven’t always publicized, because, well, black eyes and busted noses are generally frowned upon in board rooms. So at the risk of taking a career limiting detour to discuss the sweet science (dark arts?), here are some parallels I’ve identified between business and boxing. And scattered throughout I’ll share some videos of me getting punched in the face. Enjoy.
You have to put in the roadwork when no one is looking.
Build your base. Poor cardio gets exposed like a Papier-mâché suit in the rain. The same is true about surface level knowledge on technical topics. If you don’t commit to doing the reading when no one is looking, you risk being the fraud in the room. Similarly, I’ve found that the boxing ring is the most honest place in the world.
Sometimes you’re the hammer, sometimes you’re the nail.
Sometimes you get a bad cut in the first round. Sometimes the projector doesn’t work. Sometimes your sparring partner has fifteen pounds on you. Sometimes your prospective customer has a brother-in-law who works at the competitor… Some days you’re just the nail. But you’ll also have those magical days when things really do pan out. Buster Douglas had one of those against Tyson, when he hammered through 42:1 gambling odds.
Be a professional, make weight.
Missing weight shows a lack of dedication to yourself and a lack of respect for the game. See: Julio Cesar Chavez Jr. The prerequisites apply in business too. You say you will show up to a meeting at a certain time, show up on time. If you are trusted to send something out, spell check it first . The little things are the big things, even if they aren’t fun.
Quote from one of my first managers in consulting:
“You know spell check? Newsflash - it’s fucking free”
Less is more when it comes to corner advice.
When immediate results are needed, too much advice is unactionable. Give me one thing to think about and I’ll change it next round. Give me nine things to think about and you gave me nothing. As a boss, giving limited and specific things to improve upon are more digestible.
Just showing up everyday is half the battle.
Sometimes you just don’t want to lace up those boots and go to work. The same is true for days you don’t want to get punched in the face. It can be draining. But if you do it long enough it becomes routine, your skin (literally) gets tougher, and it doesn’t hurt as much. As my coach Roscoe once said to me,
“We spar, because, well, it’s just what we do.”
To teach is to know.
Teaching someone how to throw a left hook opens up a part of your brain that you didn’t know was there. Before you just threw it, but now you understand it differently. The same is true when it comes to teaching someone how to calculate LTV to CAC and what each component means.
Sometimes all you need is a good 1 - 2 combo to get the job done.
Just because a tactic is basic doesn’t mean it won’t be impactful. I saw a coach knock someone down with a perfectly timed jab once. Complexity often hides incompetence. And sometimes a simple strategy, executed quickly and violently, is what you need.
If you see an opening, hit it mercilessly, again and again, and again…
I discovered the right upper cut was open in the third round. I shamelessly went to the bank and made the same deposit again, and again, and again. If you find a customer segment that wants to buy what you’re selling, sell it to them until your hand hurts. Competition waits for no one.
Learn from the veterans.
This is my first ever coach, Rodney the “Punisher” Toney. A former top ten middleweight, he used to toy with us every Saturday morning, sometimes going 20 rounds in a row with any masochist or misfit who wanted to trade leather.
Quick detour - one night I changed his favorite playlist in the gym while he was teaching a class (I believe a DMX song from 1996 was playing). He saved that perceived slight for the weekend. He trapped me in the corner, with probably ten people watching, and whispered calmly through his headgear “Don’t touch my music MF” and dropped me with a liver shot. Lesson learned - not my class, not my music.
But back to what I was saying. Rod is one of the craftiest fighters. He had all these small tricks he’d pull that came from thousands of hours in the ring. For example, he showed me to push my opponents head down in the clinch and lean on them when they tied up, forcing them to back peddle across the ring while carrying my bodyweight until the ref separated us. It was something you couldn’t pick up on camera but a veteran tactic to steal your opponents energy.
Work on your footwork and keep your hands up.
In my second fight ever you’ll notice a few things:
My stance is hunched over, actually moving my face closer to my opponent
My arms are wide and basically useless from a defensive perspective
Chris’ mom is from Southie
She wants me to die
Fast forward to my seventh fight and you’ll notice a few things:
I bring my hands back to protect my face (important)
I still move around a lot but I’m wasting less energy (nice)
Omar hasn’t skipped a meal since second grade
Omar knows a talented tattoo artist
Now don’t get me wrong, I’m no Willy Pep. My defense is far from, in the words of Mike Tyson, “impregnable”. In reflection, the first clip is reminiscent of my presentation style in my first year of consulting: chaotic, full of sound and fury, but signifying nothing. The first few years I presented anything I tried to blind my audience with science, throw numbers at them from left, right, and center. Just trying to get by with a good overhand right. What I failed to do was read the room. My barrage of data points failed to provide time for people to absorb what the hell I said, and didn’t leave space for them to add to the conversation.
When I think about where I’m at now in my presentation style, I think of the second video - more deliberate, concise and thoughtful, but probably still need to keep my chin down.
You know when you are in a real negotiation just like you know when you are in a real fight
A fight is exactly that, a fight. As Triple G, Gennadiy Gennadyevich Golovkin perfectly explained,
“You don’t play boxing.”
If you’ve ever found yourself in a serious negotiation, you know what I’m talking about. It feels like the air stands still and the world outside that moment is cloaked behind an iron curtain. The same is true in a fight, or a sparring match that goes sideways. Both have an unmistakable and visceral shift in tone.
Fall in love with the process.
In the words of Marvelous Marvin,
“You have to enjoy it like a boy, but play it like a man.”
For each fight camp he’d hole up at an old, run down inn in Provincetown, the furthest tip on the state of Massachusetts. In the winter months he’d run the snowy dunes in work boots, visualizing his opponent training in sunny California or Florida. Local residents said he used to mutter “WAR…WAR…WAR”, as he ran, the cold air exposing his breath in the early morning. Pretty much the only other time he’d leave the seclusion of his room would be to spar in a makeshift ring in the hotel’s lobby.
Hagler loved the process of preparing for battle. He relished it. He felt at home when he was lost in it. And then, after 67 bouts…he packed it all up and moved to Italy to become an action movie star. Bet you didn’t see that end coming!
I’m not saying we all have to become actors in our twilight years or quit what we are doing abruptly. But there’s a romantic quality to how he fell in love with his craft, how he let it consume him, and how he was able to hang up his gloves without a regret (even after losing in controversial fashion to Sugar Ray Leonard in his final fight). If I look back like Hagler on my career, I’d be a happy man.
Now back to working on my craft.
CJ very cool you were a young cobra Kai. Very fun to watch!
This is great CJ. Thanks for sharing your story!