What It Takes to Succeed in Commercial Real Estate: Insights from Omega CRE's Joe O’Donnell & Mike Sweeney
In this episode of Bricks and Risk, Joe O’Donnell and Mike Sweeney of Omega Commercial Real Estate break down the realities of succeeding in commercial real estate—from avoiding costly lease pitfalls to surviving the brutal 3-5-7 year career trajectory. They emphasize the importance of long-term relationships, client education, and resisting the urge to chase quick commissions. With hard-won insights and honest advice, they offer a roadmap for both new investors and aspiring agents to build sustainable success in the CRE world.
📚 Table of Contents
1. Introduction: Why This Episode Matters
Commercial real estate (CRE) is a field filled with opportunity—but also landmines. In this Bricks and Risk episode, we sat down with Joe O’Donnell and Mike Sweeney, co-founders of Omega Commercial Real Estate, to explore the unfiltered realities of the business.
From lease horror stories to advice for first-time investors, and even the emotional rollercoaster of surviving your first five years in CRE, Joe and Mike offered brutally honest, practical advice.
Whether you're looking to invest in your first commercial property, considering a career in commercial real estate, or trying to grow a brokerage, this interview offers real-world insights you won't find in a textbook.
2. The Hidden Pitfalls in Commercial Leasing
“You’d be shocked how many tenants sign leases without reading the fine print—or hiring an attorney.” — Joe O’Donnell
Joe shared a story about a retired pro athlete who leased a commercial space and skipped the legal review. The result? Major financial implications, including missed lease clauses and unclear responsibilities.
This is more common than people think.
Key lease pitfalls discussed:
Business terms not making it to the final lease
Verbal agreements can disappear in the final draft.Delayed rent escalations
A rent bump kicking in month 14 vs. month 13 can be a huge win or loss over a long-term lease.Misunderstood obligations
Who’s responsible for repairs, taxes, CAM fees? Many tenants have no idea.
🛠️ Takeaway: Hiring a commercial broker and a qualified real estate attorney is essential, especially for first-time tenants or buyers. These advisors ensure you're not unknowingly signing a financial time bomb.
3. Educating First-Time Investors: A CRE Guide for Beginners
One of Omega CRE's strengths is working with inexperienced clients—often small business owners or first-time real estate investors. Joe likens it to being a good dentist:
“Talk them through it. Show them the X-rays. Explain what you’re doing and why. Make it painless.”
For many, commercial property ownership is a giant leap from leasing retail or office space. Omega's approach is built on education, transparency, and guiding clients step by step.
Common knowledge gaps they help fill:
Difference between NNN, modified gross, and full-service leases
Pros and cons of leasing vs. buying
Understanding cap rates, debt service coverage ratios (DSCR), and zoning limitations
Setting realistic timelines for occupancy and buildout
🔑 commercial real estate for beginners, first-time commercial property investment
4. The Harsh Truth: The 3-5-7 Year Career Path
“Three years to make money. Five years to get good. Seven years, you’re in it forever.” — Mike Sweeney
The Omega guys didn’t sugarcoat what it takes to succeed in commercial real estate.
Year 1-2: The Hustle Phase
Cold calls, rejection, and low commissions
Most people quit before year 3
Year 3-5: The Pivot
Your network starts to pay off
You build a book of business
You might make some money
Year 7+: Career Mode
You’re known, referred, and respected
Business becomes more inbound than outbound
This long-term arc is a massive mindset shift from other sales jobs. It requires grit, patience, and a focus on relationships over commissions.
5. Mindset Over Money: How Client-First Sales Wins
Joe and Mike repeatedly emphasized a consultative, long-term sales strategy. That means not chasing the deal. Instead, focus on helping people—even if there’s no immediate payout.
“If you're chasing every dollar, it shows. People feel that. You lose deals. But if you educate, ask smart questions, and qualify or disqualify the prospect, you gain trust—and referrals.”
Strategies That Work:
Ask the tough questions: Can they really afford this? What’s their fallback plan?
Walk away if it’s not right: Respect builds when you show you’re not desperate.
Follow up, even if the deal died: You’re playing a long game.
In a world where short-term wins dominate social media, this old-school, high-integrity approach is rare—and highly effective.
6. The Challenge of Building a Team in Real Estate
Despite Omega’s success, Joe and Mike admit they still struggle with recruiting and developing strong team members. Why? Most new agents:
Don’t fully understand the industry before jumping in
Expect quick wins and high income early
Lack a long-term commitment mindset
They’re looking for coachable, entrepreneurial people who are okay eating dirt in the early years, who crave mentorship, and who understand the delayed-reward nature of commercial real estate.
This honesty stands out in an industry that often oversells the “easy money” narrative.
7. Conclusion: Long-Term Relationships, Not Quick Commissions
If there’s one theme that emerged from our conversation with Joe O’Donnell and Mike Sweeney, it’s this:
👉 Relationships beat revenue—every time.
Commercial real estate isn’t just about cap rates and lease terms. It’s about trust, experience, patience, and staying power. Whether you’re:
A first-time buyer
A small business looking to lease space
An aspiring agent trying to break in
…the slow, steady, educational approach will serve you better than any high-pressure tactics.
Omega CRE lives that philosophy—and it’s why they’re still winning.
🙋♂️ Frequently Asked Questions (FAQ)
1. What is the difference between commercial and residential real estate?
Commercial real estate involves properties used for business (office buildings, retail, industrial, etc.), while residential involves housing. CRE often requires longer timelines, larger investments, and more complex contracts.
2. What should I look out for in a commercial lease?
Always check:
Rent escalation terms
Maintenance responsibilities
Duration and renewal terms
Options to buy
Legal review—never skip it
3. How long does it take to succeed in commercial real estate?
The typical timeline:
3 years to become profitable
5 years to gain mastery
7 years to become established
4. Should I lease or buy commercial property as a small business owner?
Depends on your capital, timeline, and goals. Leasing offers flexibility, while buying can build equity and provide tax benefits. Always analyze both before deciding.
5. How do I choose the right commercial real estate broker?
Look for someone with:
Market expertise in your property type
A proven track record
Client-first approach
Ability to educate and guide you, not just close deals