5 Lessons I Learned the Hard Way in Commercial Real Estate

Chuck Cuda & JoMarie Guastello at Country Club Shops redevelopment in 2017.

When I first entered the commercial real estate world, I thought hustle alone would lead to success. But over time, I learned that the path to meaningful impact is paved with hard lessons - and it’s not just about individual wines. One of the biggest shifts in my mindset came when I realized this career wasn’t only about closing deals, It was about helping others rise, too.

I believe a rising tide raises all ships, and the more I invest in mentoring others, sharing mistakes , and building up those around me, the more my own businesses grow! These five lessons were learned the hard way, but they’ve shaped not only my success in real estate, but my approach to leadership, collaboration, and growth.

When you’re a new broker, an entrepreneur, or just navigating the next phase of your professional life - I hope these insights help you skip a few of the bumps and build a stronger foundation.

Lesson 1: Time is Money - Qualify your Clients

As a young commercial real estate broker, I made the mistake of chasing every lead that came from a sign call. I was eager, and any prospect felt like a win. But the truth is, unqualified leads cost you more than time. If you’re not asking the hard questions upfront, you pay for it in lost time and missed opportunities. Time is money. If they bristle at qualifying questions, they’re likely not ready to move forward. In real estate - and in any sales profession - your time is your most valuable asset.

Note: Whether you're in sales, nonprofit work, or building personal relationships, qualifying who gets your time isn’t just good business—it’s smart leadership.

Lesson 2: Build a Schedule - And Stick to It

If I could talk to my 20-year-old self, I’d tell him to structure the day with intention. Back then, I built my schedule around whatever my clients wanted. It felt like the right thing to do when you’re new - but it created major inefficiencies. Now, I time-block for revenue-generating activities and protect that time. You have to be confident enough to say “Here’s when I’m available - does that work for you?” If you don’t design your day, someone else will.

Lesson 3: Commercial Real Estate Is Not “Easy”

There’s a major misconception that commercial real estate is a fast and easy career. You take a two-week class in the state of Missouri, get a license, and suddenly you’re ready to close million-dollar deals. Not true. That license doesn’t prepare you for the real world - contracts, zoning laws, liabilities, negotiation strategy or client protection. You’re just not ready. I believe every new broker should shadow a mentor for at least six months before ever brokering their own deal. It’s a profession, not a hustle and it deserves that level of training. This industry truly requires on-the-ground experience and continuous learning to succeed.

Lesson 4: This Isn’t Just Sales - It’s Representation

Commercial real estate isn’t just about putting together deals—it’s about representing your clients with professionalism, integrity, and real knowledge of the field. Sure, you can get licensed after a two-week course, but that doesn’t mean you’re equipped to protect your clients' best interests. They’re trusting you as the expert with major financial decisions, and you owe it to them to understand zoning, liability, lease terms, negotiation strategy—all of it. When you approach this industry like the profession it is, you build trust. And trust is the foundation of referrals, repeat business, and long-term relationships that outlast any single transaction.

Lesson 5: Leadership Is Multiplying Yourself

Real leadership isn’t about being the smartest person in the room—it’s about multiplying yourself through others. That’s the mindset I brought into building Opes. I didn’t name the company after myself for a reason: I wanted the people around me to feel ownership in what we were building. A rising tide lifts all ships—and that’s always been my goal.

One of my proudest examples is Nate Prather. He started out rocky—some days were solid, and other days, he wouldn’t show up at all. I had to give him the kind of tough love my uncle once gave me. But I saw potential. I invested in him the same way someone once invested in me—teaching him how to prospect with intention, negotiate with integrity, transact with discipline, and build long-term relationships.

I told him to celebrate the closing, not the contract. I reminded him that if he didn’t make the call, someone else would. I challenged him to stop waiting on opportunity and start creating it. It took time, but Nate rose to the occasion. In 2024, he closed over $39.5 million in transactional volume. That didn’t just change his business—it changed his life.

This is what leadership looks like to me: not just building success, but multiplying it in others.

Want to read the full story? Nate’s journey and the lessons that shaped our growth at Opes Commercial Real Estate are featured in my book Ego Strength: Betting on Myself, available now on Amazon.

Up next: How I Build Teams That Win: Culture, Loyalty & Accountability.
If you haven’t grabbed your copy of Ego Strength, you can find it now on Amazon HERE.