From Grit to Greatness: Building a $500M Real Estate Portfolio

One thing becomes clear when I talk to successful investors: financial freedom is never accidental. It’s the result of decades of focus, grit, and persistence. An example of this is Ben Reinberg, CEO of Alliance Consolidated Group of Companies and a man who has built a $500 million+ real estate empire.

Anyone can reach generational wealth if they play the long game, surround themselves with the right people, and stick to their niche. Ben’s story is a powerful reminder of this.

From Chicago Grit to First Deal Success

Ben grew up in Chicago, where real estate icons like Sam Zell and the Pritzker family made their fortunes. Inspired by their success, Ben embarked on building wealth through property.

After graduating with an accounting degree and becoming a CPA, he had a choice: take the “safe” route and find a traditional job or take a chance on himself. He chose the latter.

His very first deal? An industrial building in Northbrook, Illinois, with 95,000 square feet. It was a syndicated deal in which he practically tripled investor returns. After that early success, he was confident to continue his career.

However, Ben is quick to point out that it wasn’t a matter of luck. The key was preparation, grit, and the belief that every dollar mattered.

The White-Glove Investor Experience

A unique characteristic of Ben is the way he treats investors.

According to him, investing dollars is a privilege. In addition, Ben never forgets how hard they worked for it.

As a result, Ben built Alliance around offering investors a white-glove experience. He and his team don’t just buy properties; they also manage relationships. Investors aren’t numbers on a spreadsheet. Instead, they’re partners who deserve transparency, respect, and high performance standards.

As a result of that philosophy, Alliance has grown into a half-billion-dollar company that keeps investors returning.

Commercial Real Estate Grit: A Marathon, Not a Sprint

When you’ve been in commercial real estate long enough, you know it’s not always sunshine and smooth cash flow—the market’s cycle. Tenants leave. Resilience can be tested by unexpected events — like a hurricane ripping off the roof of a building Ben owned in Savannah.

His takeaway was an amazing one: “Tough times don’t last. Tough people do.”

Cash flows fluctuate in real estate. Holding on through storms, managing reserves wisely, and staying persistent are what make investors and operators successful.

Most importantly, this is not a get-rich-quick scheme. It’s a decades-long compounding machine — if you stay disciplined.

Grit Lessons from Sam Zell

Ben and I both looked up to Sam Zell, a legendary real estate investor. Sam wasn’t just an example of business success; he was also a model of grit, perseverance, and dedication.

According to Ben, Sam once told him:

• Always focus on yourself and your mind.
• Never give up — be persistent.
• If anyone tells you “you can’t,” you can.

In a business where many people burn out after just a few years, that advice stuck with him, and it’s helped him make it through 30 years.

Why Medical Office Became His Niche

Early in his career, Ben invested in large office complexes. Next came the recession, vacancies, and painful lessons about tenant improvements and rent compression. Instead of walking away, he pivoted.

His insight? The human body will never go out of style.

As a result of that realization, Alliance has become a leading company in medical office buildings. As a result of predictable demand, sticky tenants, and recession resistance, medical offices have proven to be one of his most successful investments.

Alliance now invests in industrial, multifamily, and medical office properties.

What’s Hot Right Now (and Ahead)

According to Ben, three asset classes are worth watching right now:

• Medical office. With demographic trends and steady demand, it’s still his favorite.
• Multifamily. He sees buying opportunities in the next cycle as distressed sellers and motivated sellers emerge.
• Industrial. As Alliance returns to the space in 2025, it is optimistic about the long-term growth potential.

Like me, Ben believes in sticking to niches where you have expertise. When you focus on compounding wealth, you are more likely to avoid chasing the “shiny object” of the moment.

The Case for Passive Investing

One theme Ben also hammers home is the value of passive investing.

In the world of commercial real estate, it’s a full-time job. Trying to do it on your own often leads to disaster because you don’t know how to negotiate leases, underwrite deals, or handle capital improvements.

Ben argues that instead of trying to master a second career, you should:

• Focus on what you do best. Don’t stop building wealth in your area of expertise.
• Invest passively with experts. Let operators like Alliance handle the day-to-day operations.
• Leverage relationships. Invest with someone you trust, and know who you’re dealing with.

When you do this, your capital compounds while you stay in your lane, which I often refer to as buying back your time.

Health, Mindset, and Longevity

In addition to building wealth, Ben also constructed a sustainable lifestyle.

When his children were young, he noticed that his health was slipping. After that wake-up call, fitness and mental well-being became non-negotiables for him. Today, he trains with a coach five days a week, eats clean, and practices meditation.

Why does this matter? As he put it: “If I don’t take care of myself, what good am I to my investors, my employees, or my family?”

After all, there’s more to longevity in business than balance sheets. The key is to show up year after year with energy, clarity, and resilience.

Giving Back and Mentorship

Ben is now in his mid-50s and is equally passionate about giving back as he is about doing business.

In addition to building a personal brand, launching a podcast and TV show, and writing a book, he helps others climb the learning curve faster. As an investor himself, he wishes he had a roadmap when he was just starting out.

Final Word

You can achieve financial freedom by adopting the same mindset Ben had as a young man in Chicago: every dollar matters, persistence pays off, and wealth is built deal by deal.

Key Takeaways

• Focus matters. Focus on a niche that you’re passionate about or that you’re an expert in. It will be worth it in the end.
• Relationships are everything. Don’t invest with anyone you don’t know. Wealth is built on the foundation of trust.
• Think long-term. You shouldn’t look at commercial real estate as a sprint, but as a marathon.
• Invest passively. You need experts to ensure you can focus on your niche.
• Take care of your health. The most valuable asset you have is your mind and body.

Featured Image Credit: olia danilevich; Pexels: Thank you!