How the sport of Boxing prepared me for the sport of Business
Lessons from the squared circle that I take with me to the board room
Author’s Note: This is an updated version of the first post I wrote once I started taking the newsletter seriously. That was way back in January of 2022… before we found, what I call, “audience market fit”.
A lot has changed since then. First off, the name of the newsletter was still “Steal My Idea.” I was making up business ideas and then painstakingly calculating metrics on them… like TAM and CAC Payback period for Dog Park Cameras and Monthly Vintage Concert Tee Shirt Boxes. Yea, I’m a weirdo. But it’s all part of the journey.
Second of all, we had like 200 subscribers back then (including all my first cousins and mother in law). Since then we’ve crossed the 25,000 mark, made some great friends, and bought Wally a lot of ice cream. I want to reshare and refresh this post so readers can learn a little bit more about me and why I think the way I think (disclaimer: I don’t believe it’s due to CTE, but IDK). Enjoy.
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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. I’ve found that the boxing ring is the most honest place in the world.
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. If 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 my first manager in consulting:
“Hey, so you know spell check? Newsflash - it’s fucking free”
She was right. As consultants, the quality of the work was the only thing we had to sell. It’s not like we were making physical widgets. Therefore, the small details were actually the big things that people were paying for.
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 the days you don’t want to get punched in the face. After all - it’s getting punched in the face.
That can be draining. But when 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; now you understand it differently.
The same is true when it comes to teaching someone how to calculate LTV to CAC and needing to dissect what each component means. Until you’ve taught someone the minute details, you haven’t mastered it yourself.
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 down a Golden Gloves champion with a perfectly timed jab.
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…
In this fight I discovered the right upper cut was open in the third round. I hadn’t thrown it much up until that point. So I shamelessly went to the bank and made the same deposit over, and over, and over.
If you find a customer segment that wants to buy what you’re selling, sell it to them until your hand hurts (note: I thought I broke my hand for a week after this fight). Competition waits for no one, so seize the opening while you can.
Learn from the veterans.
This is my first ever coach, Rodney the “Punisher” Toney. A former top ten middleweight contender, he used to toy with us every Saturday morning, sometimes going 20 rounds in a row with any masochist or misfit who dared to trade leather.
Quick detour - one night I changed the song from his favorite playlist while he was teaching a class (I believe it was Ruff Riders Anthem by DMX). He bookmarked that perceived slight for Saturday sparring. A few days later he trapped me in the corner and calmly whispered through his mouthpiece, “Don’t ever touch my music mother fucker,” dropping me with a liver shot.
Lesson learned - not my class, not my music.
The same can probably be said about stealing the stage, or asking a dick question, during someone else’s presentation.
But back to what I was saying. Rod is one of the craftiest fighters. He had all these small tricks 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 whenever they tied up. This forced them them to back peddle across the ring, while carrying my bodyweight, until the ref separated us. If anyone has ever done this to you, it’s TIRING. This 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, which actually moves my face closer to my opponent
My arms are wide, and basically useless from a defensive perspective
Chris’ mom is from Southie (and 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 use my footwork to control the distance from my opponent
Omar should have been in the next weight class
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, throwing numbers at them from left, right, and center.
I was just trying to get by with tenacity and a good overhand right. But what I failed to do was read the room.
My barrage of data points left no 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.
There’s a big difference between playing to Win vs playing to Not Lose
The most stinging thing my trainer ever said to me was after the second round in my first Golden Gloves. I was letting the other guy push the pace and just not throwing enough punches to wrack up any points. When I came back to the corner, he said:
So what’s the deal, man? You here to win? Or you just here to not lose?
He was right. I had spent months training for this three round fight, and I had thrown away one third of it, acting like I was just trying to get through it.
The last round I went out there and threw everything, including the kitchen sink. I didn’t care if they had to scrape me off the mat with a shovel…
You see it all the time from incumbents in the business world. They’re afraid to cannibalize themselves; they’re afraid to go out on their shields.
The whole Metaverse thing Zuckerberg went after was kinda dumb. But what was his other choice? To standby and let someone else eat his business? To just be “happy to be here?”
He knew if he wasn’t pushing the pace, throwing punches, innovating, and playing to win), eventually someone who wanted it more would show up and eat their lunch.
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. You don’t play negotiation.
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 in the twenty degree weather, the cold air exposing his breath in the early morning.
The hotel staff said the only other times he’d leave the seclusion of his room would be to spar in the 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 to the story coming!
Now, I’m not saying we all have to become actors in our twilight years or quit what we love doing abruptly. But there’s a romantic quality to how he fell in love with his craft, let it consume him, and was able to hang up his gloves without a regret once he didn’t get energy from it anymore (even after losing in controversial fashion to Sugar Ray Leonard in his final fight).
Hagler never played to Not Lose. He always played to Win.
If I look back like Hagler on my career, I’d be a happy man.
Thanks for reading. Now, back to working on my craft.
What I’ve Been Reading
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If you too want to learn from a multi-time, multi-national, multi-billion dollar CFO, look no further than SecretCFO.
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How to make great finance career decisions
Lots of GIFs, and Succession references
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