17 Years Later: 3 Actionable Lessons for CRE Brokers
By Rod Santomassimo, Founder, The Massimo Group
A Milestone Moment
Last week, I shared a personal milestone on LinkedIn:
The Massimo Group just turned 17.
I was honestly blown away by the kind messages and DMs—thank you. It means the world.
It feels like just yesterday I left Sperry Van Ness during the heart of the Great Recession and launched The Massimo Group with a laptop, a vision, and a ton of belief.
On LinkedIn, I posted 17 hard-won lessons. But here on the CRE Broker Blueprint, I want to do what we always do—turn those insights into practical takeaways you can implement today.
So here are 3 of the biggest lessons from 17 years of coaching commercial real estate brokers—plus a simple action step for each.
1. Ruthless Focus
Steve Jobs once said,
“Focus is about saying no.”
And he was right.
Top brokers aren’t the ones doing everything. They’re the ones doing the right things, over and over again, until the market sees them as the authority in their space.
Most brokers don’t fail from lack of effort—CRE pros are among the hardest-working professionals I’ve ever met.
They fail from lack of focus.
They say yes to every opportunity, every property type, every submarket. Their calendars fill up, their energy drains, and their pipeline stays scattered.
The top 1%? They choose one thing—one asset class, one market, one message—and show up relentlessly.
✅ Action Step: Define Your “One Thing”
Ask yourself: What do I want to be known for in my market?
Is it tenant rep for law firms? Industrial investment sales under 50K SF? Medical office landlord rep?
Write it down. Turn it into your brand positioning. Then align your prospecting, content, and conversations around that focus.
Because if you try to be everything to everyone, you’ll end up being nothing to anyone.
2. Scalable Systems
The true test of your brokerage isn’t how busy you are.
It’s how repeatable your results are.
Can you tell someone why you’re winning? Can you pinpoint where a deal went sideways?
Or are you just winging it?
Without systems, you’re flying blind. And flying blind doesn’t scale.
Systems give you leverage. They help you:
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Prospect without overthinking
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Follow up without forgetting
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Track deals without scrambling
Whether it’s a basic rhythm (calls on Monday, emails Tuesday, follow-ups Wednesday) or how you maintain your CRM—consistency creates predictability.
✅ Action Step: Build a “Process Before People” Mindset
Before you hire anyone or expand your team, document the key workflows in your business.
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How do you qualify a lead?
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How do you prepare for a pitch?
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What’s your handoff after a deal?
These are your playbooks. The earlier you create them, the sooner you can replicate and scale what works.
3. Weekly Teamwork (Even If You’re a Team of One)
Earlier this month, our senior leadership team flew in from across the country for a strategy session.
We celebrated wins. Realigned our goals. Mapped out the next 17 years.
But we didn’t get a team and then find success.
We found success by building a structure before we had the team.
Even if you’re solo—you still need structure, reflection, and rhythm.
You can’t run a business on adrenaline and memory. You need space to think, refocus, and reset.
✅ Action Step: Solo Brokers—Hold a Weekly Meeting With Yourself
Block 10–30 minutes every Friday. Sit down. No distractions.
Ask yourself:
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What moved the needle this week?
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What didn’t get done, and why?
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What’s the one thing I must drive forward next week?
Write it down. Track your progress like a coach would.
Because if you don’t lead yourself with clarity, don’t expect to lead a team down the line.
Looking Ahead
I’m proud of what we’ve built these past 17 years.
But I’m even more excited about what’s coming next—for us, and for you.
In this business, the brokers who win long-term know that:
✅ Consistency beats intensity
✅ Systems beat talent
✅ Focus beats noise
Here’s to your next 17.
Want Help Building Your Next 17 Faster?
👉 Book a free 30-minute Broker Break-Through Strategy Session
We’ll walk through your current focus, systems, and rhythms—and help you sharpen them to drive results.
Let’s build your future—on purpose.
