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✔️ Cool Grandpa Mode: Activated

✔️ The Zell Matrix

✔️ 3 Lessons From A True Contrarian

Cool Grandpa Mode: Activated

Here’s what we’re not about to do: pull “a Wikipedia” on you and turn this into a full-on biography. Instead, we’ll just start by giving you a sense of Zell’s sheer presence…

If we were to guess, Zell must’ve been one helluva cool grandpa. The man was just built different.

• As a 12-year-old Chicago kid, Zell would buy copies of Playboy magazine for 50 cents and sell them to other kids for $3 a pop.
  
  
• His high school yearbook picture was captioned, “I’m not asking you, I’m telling you.”
  
  
• As a University of Michigan student, he’d buy, flip, rent, and manage off-campus housing for other students.

Zell only had 1 real “job” during college, as he put it — as a traveling salesman.

“My real compensation for that job wasn’t monetary. It was getting comfortable with rejection. Indifference to rejection is a fundamental part of being an entrepreneur.”

Those building blocks would all lead Zell on a wild ride of incredible wealth-building. Plus, here he is smoking a heater and riding a motorcycle… with his group “Zell’s Angels.”

You just KNOW this man had some stories to tell.

But more than his business success, Zell would tell you it’s in the way he did things that he built his name — “A contrarian in business and private life,” as the New York Times put it when he died last year.

So let’s talk about being a contrarian, because Zell basically invented the term.

CONTRARIAN FRAMEWORK

The Zell Matrix

Before you learn more about Zell’s billion-dollar poems (not a joke), or watch his great “What a crock of $hit” hot mic on CNBC… there’s some context you should know.

If we were to visualize Zell’s understanding of ownership (and how to play the game) in just 1 graphic, it’d be this — the Zell Matrix.

The matrix is an interesting way to think about any deal, any business, and frankly, any moment.

It’s about knowing who holds the risk and who controls it, and it breaks down into 4 quadrants:

1. The Cog Club

(Low Control, Low Risk)

Congratulations, you’re a cog in the machine. Zell might’ve called this one “a zone for sheep.” Low risk. Low control. Beige. If you aren’t interested in ownership, you’d probably fit in here, and that’s fine. Risk and control are not for everyone.

2. The Gambler’s Basement

(High Risk, Low Control)

This is probably the worst place to be. At best, it’s memorable. At worst, enjoy bankruptcy. You belong here if you like taking on all the risk but holding none of the cards. With no control over terms, good luck to you — because that’s the only thing that can save you.

3. The Safe Bet

(Low Risk, High Control)

Sure, you’re in charge — of nothing. But honestly, this is where most people should probably sit. You control the office thermostat, but someone else controls the building. These are the people who want to play it safe and can be successful doing so, it’s just that their definitions for “safety” and “success” are often different than those of owners.

4. The Zell Zone

(High Risk, High Control)

Ownership is inherently risky. So the game isn’t about avoiding risk — it’s about controlling the risks you take. The Zell Zone is for those who want to swing big but maintain control over the bat. Many owners live in this zone. If you’re not in this zone, you’re probably playing the game under someone else’s rules. Zell’s magic was never in “playing it safe,” it was in paying it smart and playing it hard — that much you should remember.

3 Lessons From A True Contrarian

Most people zig. Zell? He zagged, hard. Like, how many billionaires do you know of who use the free version of Zoom?

In all seriousness, Zell understood it’s not just about knowing the rules of the game, but knowing how to protect yourself when those rules start to change.

Whether it’s rising federal debt, interest rates, or a shaky real estate market. He knew the power of being prepared for turbulence — and how to grow despite it.

Our recent podcast on financial freedom in uncertain times might even help you do the same.

Zell famously said, “When everyone is going left, look right.” And that’s how he built his empire.

Where real estate markets tanked, Zell saw opportunity. And he didn’t just dabble — he went in hard. He built Equity Office Properties Trust into a behemoth and sold it for $39 billion in 2007, right before the real estate market collapsed.

In case it wasn’t f*cking obvious at this point, there’s a lot we can all learn from him…

Lesson 1: Go For Freedom

Zell’s approach to life and business was simple: go for freedom. Not the kumbaya, “find yourself in Bali” kind, but the kind that lets you control what really matters.

“Go for freedom,” as he put it. “Freedom allows you to control what you work on. If you control what you work on then you can work on what you love. If you love it you will do it for a long time. If you do it for a long time you will get really good at it. Money will come as a result.”

Lesson 2: Be a Doer, Not a Dumbass

Being contrarian for the sake of it? That’s just being a damn hipster. Zell was a student, a strategist, and a professional opportunist.

Zell knew being a Contrarian didn’t mean being a dumbass. It meant seeing things differently. He still did the work, evaluated risks, and pulled the trigger when the math mathed.

“Grave dancing involves confidence, optimism, conviction, and no small amount of courage,” he said. “All the opportunity in the world means nothing if you don’t actually pull the trigger.”

Lesson 3: Be Ready to Walk

Most of us are emotional morons — we cling to failures, convinced we can turn them around with “just a little more time.”

Zell? He’s the guy who flips the house, takes the cash, and never looks back. He knew when to sell, and more importantly, he knew when not to fall in love.

Zell liked to reference the old Peter Drucker quote, “We suffer from knowing the numbers.” He meant that no matter how attached you are to the idea of a deal, you must look back to the numbers.

It’s ALLLLL About Relationships

At the end of the day, if you want to build a life worth living or a business worth owning, you have to think like an architect.

You have to control the terms, take the risks, and most importantly, own the failures along with the successes.

The absolute best way to architect success across the board: build strong relationships.

“For those who think you can’t get to the top unless you beat the crap out of everybody — you’re wrong,” Zell’s said.

“When your world is your business and your business is your world, it’s all about long-term relationships. In any negotiation, I believe in leaving a little bit on the table. And in any relationship, I believe in sharing the stakes. I’ve been doing deals with many of the same people for decades because the goal is for us to all come out ahead.”

Ultimately, real ownership isn’t just about assets or power — it’s about building something that lasts and knowing who’s still with you when the dust settles. And that’s what separates the fine owners from the great ones.

If ownership interests you…

There are a few ways we can help.

You can enroll in our Main Street Accelerator course. Learn how to source, evaluate, and negotiate, with around 20 hours of lessons on small business acquisitions.

If you’re ready to get serious, the Contrarian Community is our premier program for ambitious dealmakers, owners, and achievers working to build ownership. Grow into a pro through high-caliber education, expert-led guidance, and incredible peer support.

We’ll also be hosting a free, live, virtual business-buying training in October. Keep an eye out for more details.

LEVEL UP

Cool things to check out:

Watch: Our visit to an AWESOME street sweeping business (and everything we learned about how to start and build one).

Read: The 9 biggest myths people believe about their websites – and exactly how to fix them.

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