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Always Play Offense AND Defense, Part IV

The 12-Round Fight

Matt McDonagh's avatar
Matt McDonagh
Nov 15, 2025
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We’ve covered a lot of ground in this series.

Part I

Part II

Part III

Across three articles, we gone from core philosophy to practical application.

You may not realize it, but I’ve been making you lethal as a business person.

a man wearing a mask is hugging another man with the words now is not the time for fear written below him

We started with the central principle of the sweet science: every move must be both offensive and defensive.

We translated that philosophy into a practical playbook, a mental model centered on the Dual-Purpose Question.

From there, we moved from the individual to the collective, exploring how to build a winning team in your corner (the unstoppable Promoter and the immovable Cutman) and how to harness their productive conflict to forge resilient strategy.

If you’ve absorbed these lessons, if you’ve begun to run these drills in your own mind and with your own team, you have fundamentally changed the way you operate.

You are no longer a business brawler, leading with your chin and swinging for the fences. You are a technician. You now possess the mindset, the process, and the team structure of a champion. You are the most dangerous person in the board room.

But there is one final, unforgiving dimension that separates the great fighters from the true legends of the sport. It’s the invisible opponent present in every match, every career, and every business venture. It’s the one variable that relentlessly exposes weakness, rewards discipline, and grinds even the strongest down to dust.

I’m talking about Time.

The core philosophy of playing offense and defense is a constant, a North Star for your decision-making. But the balance between them cannot be static. It must be fluid, dynamic, and intelligently adapted to the context of the fight. The single greatest strategic error a leader can make is to fight every round the same way. The rhythm of your business, its strategic cadence, must evolve.

So welcome to the championship bout.

This is a 12-round fight for the title.

The lights are bright, the crowd is roaring, and your legacy is on the line. Your strategy must evolve from the opening bell to the final, echoing moment.

The Early Rounds (1-3)

The Start-up Slugfest

This is the birth of your company. The raw, chaotic, beautiful beginning.

I’m here right now with an AI start-up. It’s a magic time.

You are in the garage, at the co-working space, fueled by cheap coffee and pure conviction. You have almost nothing to lose because you have almost nothing to your business’ name: no significant market share, no recognizable brand, a handful of beta users who are mostly friends and family. But this freedom comes at a cost. Your resources are brutally finite. Your runway is a short, unforgiving strip of asphalt.

You are fighting for the two most fundamental things in the universe of business: survival and recognition.

Your Stance: 80% Offense / 20% Defense

This is the only time in your company’s life when your stance will be, and must be, so aggressively weighted. You are the unranked, unknown challenger. No one gets a title shot by being cautious.

This is your moment for controlled recklessness.

Your Offense (80%): The offense in these rounds is about pure, unadulterated, maniacal velocity. You are a whirlwind of activity, throwing a constant flurry of punches, testing your opponent’s defenses, and hoping to land a few clean shots that get you noticed. This is the frantic, desperate search for product-market fit. It’s the guerilla marketing tactic that feels half-brilliant and half-insane.

You are shipping code at 2 a.m., taking every sales call yourself, and iterating on your product based on raw, unfiltered customer feedback. You have to make noise. You have to take risks. You must be willing to get hit, to look foolish, to try ten things knowing nine will fail, because the one that works could change the entire fight.

Your Defense (20%): A 20% defense posture can feel like a rounding error, but in the early rounds, it is the difference between life and death.

DO NOT ABANDON DEFENSE COMPLETELY.

Your defense here isn't about building a fortress; you have no jewels to protect yet. It is about simple survival. Don’t die as you fight to live. It’s about not getting knocked out by a foolish, self-inflicted blow.

The first rule: do not lose. What does this look like?

  • The Founder "Pre-nup": It’s having the brutally awkward but necessary conversations with your co-founders about equity, roles, and what happens if one of you wants out. A co-founder dispute is the number one killer of early-stage companies. Your founding documents are your first and most critical defensive wall.

  • Intelligent Capital: It’s understanding that not all money is created equal. Your defense is choosing investors who bring expertise and patience, not just a check with predatory terms that will cripple you later. I am very good about saying no to money in order to unlock more strategic partnerships.

  • Basic Legal Armor: It’s spending the few thousand dollars you can’t afford on basic IP protection and well-structured employment agreements. It’s a shield, however small, against the patent trolls and legal vultures that prey on the young and vulnerable.

  • Cash Management: Above all, your defense is a paranoid obsession with your bank balance. Cash is oxygen. Your primary defensive job is not to run out of it. Every dollar you spend must be scrutinized. Is this an offensive investment in growth, or just a vanity expense? Neglecting this 20% isn’t a risk; it’s a suicide pact.

Control the burn as you look for asymmetric ways to scale your growth.

The Middle Rounds (4-8)

The Technical Separation

The bell rings for round four.

You’re still standing. You’re a little bruised, but you’ve landed some clean shots.

You’ve survived the opening brawl. You have found product-market fit. You have a growing, loyal customer base and a brand that is starting to mean something in your industry. You are no longer the unknown underdog; you are a legitimate contender. The fight is no longer just about survival; it’s about strategic domination.

Now it’s about pulling away from the pack on the judges’ scorecards.

This is also when the tactics get the most important.

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