At our December DIG Philadelphia meeting, Fred Hubler shared the rest of the story behind that $9 million tax savings deal with real estate owners involved in property management in Philadelphia. What started as one family's retirement solution created a chain reaction that transformed the financial lives of everyone involved—from the local real estate agent to the mortgage broker, and even a working mom who simply paid attention.
We already know about the family: $14 million mobile home park, fully depreciated, parents ready to retire. Through a strategic 1031 exchange into Delaware Statutory Trusts, Hubler saved them $9 million in taxes while increasing their passive income.
Their thank you gift? A box of cigars.
But that was just the beginning of the story.
The local real estate agent who handled the transaction made so much in commission that he bought himself a used Bentley. Not a new one—a used Bentley. He was so proud of it that he drove over to show Hubler.
Hubler's response? "Where's my Fred parking spot?"
His reward for orchestrating a nine-million-dollar tax save and changing a family's retirement trajectory? Another box of cigars.
Then there was the mortgage broker involved in the deal. He also made substantial money on the transaction. His thank you gift to Hubler?
You guessed it—another box of cigars.
As Hubler joked, "I had more cigars, so I think they're trying to kill me."
But here's where the story gets really interesting—and reveals the true power of financial education.
There was a working mom at the real estate agency. You know the type—juggling kids and career, working as an agent on the side, probably not the highest-earning person in the office. The kind of person who might assume that sophisticated tax strategies and investment vehicles like DSTs are only for the ultra-wealthy.
She watched this deal unfold. She paid attention. She asked questions. She learned.
And because she understood how DSTs work, she was able to do one herself.
This is the part that matters most. Not the Bentley, not even the $9 million in tax savings. It's that a working mom—someone who might never have considered herself in the same league as million-dollar property owners—gained access to wealth-building strategies simply by being exposed to them.
DSTs aren't just for the ultra-wealthy. They're for accredited investors, which includes many real estate agents, small business owners, and dual-income professionals. The barrier isn't usually the money—it's the knowledge that these tools exist.
That working mom didn't need to own a $14 million mobile home park. She just needed:
Let's be honest about what happened here:
The Family: Saved $9 million, increased passive income, retired to play golf → Gave cigars
The Real Estate Agent: Earned enough commission to buy a used Bentley → Gave cigars
The Mortgage Broker: Made substantial commission → Gave cigars
Fred Hubler: Orchestrated the entire strategy, saved $9 million, changed multiple lives → Got really good at storing cigars
There's something beautifully ironic about this distribution. But Hubler tells the story with genuine humor and without bitterness because he understands something important: The best deals create value for everyone involved.
This isn't really about cigars or Bentleys or even about $9 million in tax savings. It's about three powerful principles:
1. Good Deals Create Rising TidesWhen structured properly, real estate transactions can generate wins for everyone—the sellers, the buyers, the agents, the brokers, and the advisors. Nobody has to lose for others to win.
2. Knowledge is the Real WealthThe working mom didn't inherit a mobile home park or get lucky. She gained access to wealth-building tools by simply understanding how they work. That's replicable.
3. Proximity MattersBeing around people who understand sophisticated financial strategies—even if you're just watching from the sidelines—can change your entire financial trajectory. The working mom wasn't even directly involved in the deal, but she was close enough to learn from it.
Here's the practical truth: DSTs require accredited investor status, which generally means either:
That working mom in the real estate agency? She likely qualified—not because she was wealthy, but because her professional success and real estate holdings put her over the threshold. She just didn't know tools like DSTs existed until she saw one in action.
Hubler tells this story with a sense of humor, but there's wisdom in it. The disproportion between the value created and the gratitude expressed isn't the point. The point is that when you help people solve real problems—when you save them millions in taxes, help them retire comfortably, enable them to sleep better at night—the relationships and reputation you build are worth more than any commission.
And sometimes, those relationships lead to a working mom learning something that changes her financial future. That might be worth more than all the cigars in the world.
Even if you're trying to figure out where to store them all.
Delaware Statutory Trusts require accredited investor status and have minimum investment thresholds typically starting at $100,000. This article is for educational purposes only. Always consult with qualified tax, legal, and financial professionals before making investment decisions.