Always Play Offense AND Defense

I love the way people talk about business.

They use the language of war, of sports, of a high-stakes poker game. And they’re not wrong, not entirely. But they’re missing the nuance. They see the game, but they don’t see the whole board. They’re all offense, all the time.

“Go, go, go.”

“Growth at all costs.”

“Move fast and break things.”

I’ve seen it a thousand times, and I’ve seen the wreckage it leaves behind.

Me? I think of it differently. I think of it like a boxer. Not a brawler, swinging for the knockout with every punch, but a technician. A master of the sweet science. Every move you make in that ring has to have a dual purpose. It’s not just about landing a punch; it’s about what happens after you land the punch. It's about where your hands are, where your feet are, where your opponent is. It’s offensive, yes. But it's also defensive.

It has to be both.

Every. Single. Time.

This is the philosophy that’s guided my every move in business. Every hire, every product launch, every contract negotiation. I don't just ask, "How does this get me closer to my goal?" I also ask, "How does this protect me if everything goes to hell in a hand basket?" Because it can. And it will. The basket of chaos is always there, waiting.

Let’s talk about the offensive game first, because that’s the part everyone loves. That’s the sexy part. That’s the part that gets you on the cover of magazines. The offensive game is about taking ground. It’s about creating opportunities. It’s about making things happen. And I’m a believer in the offensive game. I’ve made my share of bold moves. I once bought a company for what everyone thought was a ludicrous amount of money. The analysts were screaming. My own board was sweating bullets. But I saw something they didn’t. I saw a piece of technology, buried deep in their portfolio, that was the key to unlocking a whole new market. It was a pure offensive play. A land grab. And it worked. We integrated the tech, we launched a new product line, and we owned that market for the next five years.

It was a beautiful thing.

But here’s the thing about a pure offensive play: it leaves you exposed.

Exposed like a fighter who throws a haymaker and leaves his chin wide open. If you connect, you’re a hero. If you miss, you’re on the canvas, looking up at the lights. In my case, the acquisition worked. But there were a thousand things that could have gone wrong. The tech could have been a dud. The integration could have failed. The market could have shifted. I got away with it. But I also learned from it. I learned that the thrill of a pure offensive play is also the siren song of self-destruction.

I didn’t move my feet. I just swung. It worked this time. But what about next time?

That brings me to the defensive game. The unsexy part. The part nobody wants to talk about. The part that doesn’t get you on the cover of magazines. The defensive game is about protecting what you have. It’s about mitigating risk. It’s about building a fortress around your assets. And it’s just as important as the offensive game. More so, even. Because you can’t win if you’re not in the game. And the defensive game is what keeps you in the game.

I learned this the hard way, of course. Early in my career, I was involved in a software start-up. We had a brilliant product, a killer team, and a market that was ripe for the picking. We were all offense, all the time. We were so focused on growth that we neglected the boring stuff. The legal stuff. The compliance stuff. The “what-if” stuff. And then the “what-if” happened. A patent troll came out of the woodwork with a bogus claim. It was a shakedown, pure and simple. But we weren’t prepared. We hadn’t done our homework. We hadn’t built our defensive walls. The lawsuit dragged on for months. It drained our resources, it distracted our team, and it scared off our investors. We eventually won, but it was a pyrrhic victory. The company never recovered. We had the better product, the better team, the better vision. But we lost because we didn't play defense.

That’s when it clicked for me. That’s when I realized that the real magic, the real genius, is not in playing offense or defense. It’s in playing both at the same time. It’s in making every move an offensive and a defensive move.

Let me give you an example. A few years ago, we were looking to expand into a new market. A lucrative and notoriously difficult market. The conventional wisdom was to go in big. Make a splash. Spend a ton of money on marketing and sales. A classic offensive play. But I knew that was a recipe for disaster. This was a market with entrenched incumbents, complex regulations, and a customer base that was skeptical of outsiders.

A frontal assault would have been suicide.

So we did something different. We found a small, struggling company in that market. A company with a good-but-not-great product, a decent customer base, and a team that knew the local landscape inside and out. But they were on the verge of bankruptcy.

We didn’t acquire them. Get more creative than that, if you want to win in business.

That would have been too risky. Too much of a commitment. Instead, we structured a deal that was a masterpiece of offensive-defensive thinking.

Offensively, the deal gave us a foothold in the market. We got access to their customer list, their distribution channels, and their local expertise. We also had the option to acquire them outright if things went well. It was our beachhead. Our Trojan horse.

Defensively, the deal was a thing of beauty. We weren't on the hook for their liabilities. We didn’t have to take on their debt. We had a clear exit strategy if the market turned against us. We had, in essence, all of the upside with a fraction of the risk.

And what happened?

The market did what markets do. It went sideways. A new wave of regulations came in and wiped out a bunch of the smaller players. The incumbents got into a price war that decimated their margins. It was a bloodbath. And we were on the sidelines, watching it all unfold, with our little partnership intact. We weren't losing money. We were learning. We were waiting.

And then, when the dust settled, we made our move. The incumbents were weakened. The market was consolidated. And we were the new kids on the block with a clean balance sheet and a deep understanding of the new landscape. We exercised our option to acquire our partner company for a song. We launched a new product, tailored to the new normal, and we took the market by storm.

That’s what I’m talking about. That’s the sweet science of business. It’s not about throwing wild punches. It’s about the subtle shift of weight, the slight turn of the shoulder, the move that both advances your position and protects you from a counter-attack.

This philosophy, this offensive-defensive mindset, it permeates everything I do now. When I hire someone, I’m not just looking for skills and experience. I’m looking for character. I’m looking for someone who will be a great asset to the team (offense), but also someone who won’t be a liability if things go wrong (defense). When I launch a new product, I’m not just thinking about the features and the marketing. I’m thinking about the potential for lawsuits, the regulatory hurdles, the customer support burden. I’m building in the defensive measures from day one.

It's a mindset that's hard to teach.

It goes against the grain of our "growth at all costs" culture. It requires a certain kind of paranoia, a healthy dose of skepticism, and a willingness to look at the world not as it is, but as it could be, in all its messy, unpredictable glory.

But if you can cultivate it, if you can make it a part of your DNA, you’ll be unstoppable. You’ll be the boxer that no one can touch. The one who's always one step ahead, always in control, always ready for whatever comes next. Because you’re not just playing the game.

You’re playing the whole board. And that, my friends, is how you win.

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I started Wealth Systems in 2023 to share the systems, technology, and mindsets that I encountered on Wall Street. I am a Wall St banker became ₿itcoin nerd, ML engineer & family office investor.

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