What ‘Getting Strategic’ Actually Looks Like in Property Management

Marc Cunningham’s Playbook For Getting Strategic

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Every business owner dreams of the same thing: full agency over their time.
To spend their days doing the work they actually enjoy.

That’s the promise behind every hire, new system, or piece of technology we chase.
And it’s exactly what people are hoping AI will finally deliver: more freedom, less firefighting, and the ability to focus on what really matters.

But that desire isn’t new. Long before AI, a handful of leaders were already doing it… building businesses that ran without consuming them.

Marc Cunningham is one of them.

As the President of Grace Management, Marc helped scale to more than 1,200 doors not by grinding harder, but by getting strategic about how he spent his time.

His approach is built on counterintuitive truths. Like how reading The Wall Street Journal can be a better use of time than answering emails, and how difficult legislation can become a competitive advantage instead of a setback.

In Marc’s story, there are universal breadcrumbs for how to get there by:

• Reclaiming your time
• designing your role around leverage
• truly thinking like a CEO

And it all starts with one deceptively simple shift in thinking: a single question that redefines what it means to invest strategically.

The Wrong Question To Ask If You Want To Get Strategic

When most business owners consider making a strategic investment, they ask two questions:

“What will it cost?” and “How long until it pays for itself?”

It’s a reasonable instinct.

But it’s also the exact thinking that keeps you stuck because it treats strategy like an expense instead of a catalyst.

Marc Cunningham takes a different approach.
Before making any major investment, he asks one deceptively simple question:
“How will my newly freed time pay for this?”

That question changes everything.
It shifts your focus from cost to creation. From scarcity to leverage.

Marc learned this early.
Years ago, he was stuck handling tedious move-out inspections at a mini-storage facility, and he realized he was trapped in the low-leverage role of a site inspector while high-value opportunities passed him by.

So he hired someone to take those tasks off his plate.
His first thought wasn’t “Can I afford this?” It was, “What can I do with the time this buys me?”

That simple reframe became the turning point.
The result? That single hire paid for itself many times over.
Not because it reduced costs, but because it created space for strategic work—the kind that multiplies everything that follows.

That’s the secret accelerator to getting strategic:

If you can find the time to think, you can multiply everything that follows.

And once you’ve done that (once you’ve bought back your time), the next challenge becomes even more important:
What do you fill that time with?  Where do the truly strategic ideas come from?

Where the Best Strategic Ideas Actually Come From (Hint: Not Property Management)

Buying back your time is only the first move. The next step is learning how to use it strategically.

Most property management leaders use their newly freed time to double down on the same industry sources: reading the same blogs, attending the same conferences, and copying the tactics of their competitors.

This approach guarantees they stay on the hamster wheel, getting the same results as everyone else. It’s a path to imitation, not innovation.

Marc does the opposite.

He feeds his brain new inputs.
He reads The Wall Street Journal every morning, not for property management news, but for ideas from other industries.

“My best ideas,” he said, “never came from our industry. They came from seeing how someone in a completely different world solved a problem.”

That habit (looking outside the hamster wheel) was the spark behind one of his most notable strategic leaps: content.

He didn’t learn it from another property manager. The idea came from an unexpected place- a book written by a guy who sold swimming pools.

Marc read that story on a flight and immediately connected the dots. If education could sell swimming pools, why couldn’t it work for property management?

So he applied that idea to property management…teaching, educating… instead of selling, sharing instead of pitching.

That single shift launched an entirely new flywheel of inbound business, and illustrates the lesson here-

When you stop chasing tactics and start collecting patterns from outside your industry, you’ll see opportunities no one else even recognizes.

That one strategic bet (content) didn’t just work.

It snowballed. It set off a chain reaction that probably defines the way you look at his business today..

Each move Marc made from there: speaking, investing, even turning “a visit to his office” into a product was born from that same strategic muscle.

How Getting Strategic Turns Problems Into Revenue Streams

Every strategic move creates leverage. And the best part? Leverage compounds.

For Marc, it started with content.
Those first scrappy, unpolished videos (filmed with his 13-year-old son holding the camera) weren’t marketing.

They were education. He wasn’t trying to go viral; he was trying to help.

That single decision to teach, not sell, shifted the entire trajectory of his business.

Content established his expertise. It gave Grace Management credibility before the first conversation. And soon, it opened new doors (bigger ones).

Step 1: Content → Speaking
That growing visibility led to speaking invitations. One day, a conference speaker canceled at the last minute, and Marc said yes. He didn’t have slides. He didn’t have a plan. But that moment started a new pathway in his career.
Now, speaking isn’t just something he does, it’s a core growth channel.

Step 2: Speaking → Demand & Influence
Speaking established him as a national authority in the industry. It put him in front of hundreds of other operators and dramatically increased the demand for his time and expertise. This is what led directly to his next strategic move.

Step 3: Demand & Influence → Productizing the System
As Marc’s profile has grown, he’s received more and more requests to pick his brain. Rather than saying yes one by one, he productized the demand.
He created the Visit Grace program. A paid, immersive experience where leaders tour his operation, meet his team, and learn his systems.

The bug became the feature.
What used to interrupt his workday became a significant revenue stream.

That’s what strategic work looks like in motion.

Each idea funds the next. Each opportunity creates another layer of leverage.

And the deeper Marc leaned into this kind of thinking, the bigger his canvas got.
He stopped thinking in terms of content or hiring and started thinking in terms of influence.

And as Marc’s leverage compounded, his focus naturally expanded from building systems inside his business to shaping the system around it

The Ultimate Goal Of A Strategist: Shaping Your Market

When you build enough leverage, your attention shifts.
You stop thinking about how to grow your business and start thinking about how to shape the environment your business grows in.

That’s exactly where Marc finds himself today.

As Denver’s rental market grows more hostile toward landlords, most property managers are frustrated. They complain about new regulations. They brace for impact. Marc took a different approach.

Instead of fighting legislation, he’s leaning in. He began engaging with policymakers, offering feedback, and helping design fairer, more balanced regulations that protect both landlords and tenants.

“Strategic leaders don’t just react to change.

They help write the rules.”

And it’s not just about politics or policy.  It’s about thinking like a market architect.

Someone who can see where the industry is heading and position themselves ahead of it.

This is the natural endpoint of getting strategic: When you stop firefighting and start designing, your business becomes bigger than your to-do list. It becomes part of shaping the ecosystem it lives in.

But here’s the paradox of getting strategic: the higher you climb, the quieter it gets. That’s why the battle isn’t always external, it’s internal.

The Unspoken Enemy of Getting Strategic? Guilt & Fear

After laying out this entire playbook, my biggest takeaway from the conversation with Marc wasn't a specific tactic or strategy. It was the honest truth about the internal battle a leader has to win.

The real work isn't just executing the plan; it's overcoming the mental obstacles that keep you trapped. Listening to Marc, I realized it all comes down to two core challenges:

1. The Guilt of “Doing Nothing”: He was brutally honest about the guilt that comes with an empty calendar and the discipline it takes to protect that strategic space.
2. The Fear of Imperfection: His bias for "imperfect action" - from filming a scrappy video to saying yes to a last-minute talk is a powerful reminder that we need to "do it to figure it out, not figure it out to do it."

There was a moment near the end of our conversation that crystallized this entire idea for me. I've included the clip below because it’s something every business owner needs to hear.

What Marc did manually: delegating, documenting, and creating leverage through people and systems…

today’s leaders can now do with AI.

Investing in AI to automate your mundane tasks is no different from Marc hiring that first person to handle site visits. Both are strategic investments in the same thing: leverage.

Now, automating the repetitive, low-value tasks with AI is just the next evolution of the same pattern.

The tools change, but the leader’s real job never does, to buy back time, think clearly, and build what’s next.

AI isn't a new, complicated mandate you have to follow. It is simply the most powerful tool we've ever been given to do the leader's real job: creating the leverage necessary to get out of the weeds, think clearly, and build the future.

So the question isn’t whether you’re ready for AI.

It’s whether you’re ready to think (and lead) strategically.

—

Pablo Gonzalez,

Chief Evangelist at Vendoroo

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