By Jeffrey Hayzlett
On a recent episode of All Business with Jeffrey Hayzlett, I sat down with Ray DeWitt, President and Co-Founder of 1031 DST Group and we talked about something every entrepreneur, investor, and business owner cares about:
How do you keep more of what you earn and make it work harder for you?
Let’s be honest. Most people spend decades building wealth and then hand a big chunk of it over to the IRS because they didn’t plan ahead.
Ray’s business is about changing that.
The “Terrible T’s” of Real Estate
Ray has a phrase I love: retiring from the “toilets, tenants, and trash.”
If you’ve ever owned rental property, you know exactly what he’s talking about.
A 1031 Delaware Statutory Trust (DST) allows investors to sell investment real estate and move into a truly passive structure that still qualifies under Section 1031. Instead of managing a property yourself, you own fractional interests in institutional-grade real estate through a trust.
You still:
- Stay invested in real estate
- Receive cash flow
- Participate in appreciation
But you don’t get the 2AM phone calls about broken air conditioners.
That’s what Ray means when he says, “Retire from management, not from income.”
And that’s powerful.
The Clock Is Ticking: 45 Days
Here’s where things get serious.
When you sell a property and want to execute a 1031 exchange, you don’t get forever to decide what’s next. You have 45 days to identify your replacement property. And you cannot touch the money; it must go to a qualified intermediary.
Ray told me he gets those frantic calls on Day 44. “Ray, I just sold a building. I’ve got $2 million in gains. What do I do?”
Panic is not a strategy.
The lesson? Planning beats scrambling every time.
This Isn’t Just for the Ultra-Wealthy
Here’s something that stood out to me.
These strategies aren’t just for Fortune 500 CEOs or Wall Street insiders. The definition of an accredited investor today is far more accessible than it was 20 years ago.
Ray has seen the shift firsthand. More professionals, doctors, engineers, and business owners are realizing that the tax code isn’t just a bill. It’s a roadmap. And if you understand it, you can use it.
As Ray put it, “Pay yourself, not the IRS.”
That doesn’t mean doing anything illegal. It means understanding the tools available to you and using them strategically.
Beyond Real Estate: The Rise of Alternatives
What surprised me most was how far this world has expanded.
Yes, Ray works in real estate DSTs. But he also helps investors look at:
- Oil and gas investments that can offset W-2 or 1099 income
- Opportunity Zones
- Wildlife conservation funds
- Precious metals vaulting
One of the more fascinating examples? Wildlife Partners, a Texas-based group focused on breeding and conserving exotic and endangered wildlife as part of an investment structure.
It’s not something most people think of when they hear “portfolio diversification.” But that’s the point.
The investment landscape is evolving. The menu is bigger.
And as Ray explained, more people want hands-off, professionally managed alternatives that offer tax efficiency and diversification.
Opportunity Zones: The Long Game
We also talked about Opportunity Zones.
These were originally introduced during the Trump administration’s first term and recently renewed. The premise is simple: invest capital gains into designated economic development areas and receive tax deferral benefits.
But here’s the kicker: hold the investment for 10 years, and the new gains can be 100% tax-free.
That’s not a loophole. That’s legislation designed to encourage development and investment. And again, most people don’t even know it exists.
Keep You Rich vs. Get You Rich
One thing Ray said that really resonated with me:
“These are keep-you-rich investments, not get-you-rich investments.”
That’s a mature mindset.
Too many investors chase the next big thing. The home run. The unicorn.
Ray’s focus? Preservation. Cash flow. Tax efficiency. Transparency.
Clarity Wins
Ray grew up in St. George, Utah. Not exactly Wall Street.
But he operates in high-level financial circles because he does something most advisors don’t: he simplifies.
He lays out options like a restaurant menu. Here are the pros. Here are the cons. Here are the risks.
If you don’t understand what you’re investing in, you shouldn’t be investing in it.
That’s a philosophy I respect.
What I Learned
Here’s my takeaway.
There are buried treasures in the tax system. Most people just don’t know where to dig.
Ray DeWitt does.
And whether you’re selling a business, exiting real estate, or just tired of managing the “terrible T’s,” the real question isn’t whether you’ll pay taxes. It’s whether you have a strategy. Because in business and in wealth, clarity isn’t optional. It’s everything.
Watch the full episode of All Business with Jeffrey Hayzlett, live from the New York Stock Exchange.
