My name is Ray DeWitt, and after more than two decades in financial services, I became known for helping real estate owners and high-income professionals understand 1031 exchanges and Delaware Statutory Trusts as part of broader, tax-aware planning conversations.
That wasn’t the plan when I started.
For most of my career, I did what many financial advisors are trained to do. I worked inside traditional financial planning. On paper, everything worked the way it was supposed to. The models made sense. The strategies checked the right boxes. But over time, something didn’t sit right with me.
The clients I was working with had other problems besides their 401(k)s or mutual funds. They owned real estate. They ran businesses. And I started to feel like I was solving the wrong problems.
The advice they were getting rarely touched the issues that kept them up at night. At the time, I didn’t yet know how to deliver that.
What I did know was that I was increasingly frustrated, I felt like I was solving the wrong problems.
So I started learning. I dug into private equity, real estate structures, and alternative strategies that solved more than just an investment need. These approaches addressed taxes, lifestyle concerns, and long-term planning in ways traditional models often didn’t.
A Chance Encounter That Changed Everything
After leaving a large financial institution, a sales representative walked into my office one morning with a box of donuts. He started talking about something most people don’t hear often: 1031 exchanges and a structure called a Delaware Statutory Trust.
I thanked him for the donuts and moved on.
The very next night, I attended a cocktail party and met a man who told me, almost casually, that he had sold sixty-five rental properties over the prior year. He was exhausted. Completely done with being a landlord.
He ended up paying all the taxes. He didn’t care anymore. But he said something that stuck with me.
He sure wished there had been other options.
My head almost exploded.
I had just heard about a strategy the day before that addressed exactly the problem this man, and so many others, were facing. And almost no one knew it existed.
That was the moment it clicked.
Seeing the Bigger Picture
As I started digging deeper, the macro picture became impossible to ignore.
Baby boomers own nearly half of all real estate in the United States. Many are reaching a point where they want less responsibility, more flexibility, and clarity around taxes, income, and legacy.
The questions kept coming up:
- How do I exit without giving a third of this to taxes?
- How do I stop managing properties without abandoning real estate altogether?
- How do I turn what I’ve built into something simpler and more predictable?
That’s when I realized this wasn’t a niche. It was a massive, underserved decision point.
From Headaches to Structure
A traditional 1031 exchange allows you to sell one investment property and buy another while deferring capital gains taxes. But in practice, that often just means trading one set of problems for another.
More tenants.
More toilets.
More management.
What the Delaware Statutory Trust introduced was something different.
It allowed investors to remain in institutional-quality real estate, preserve the tax treatment they cared about, and shift into a fully passive structure, without having to become something they weren’t.
I often describe it as moving from headache management to structure.
You’re still in real estate.
You still receive income.
The tax characteristics carry forward.
But the day-to-day responsibility doesn’t follow you.
For many people, that change alone alters how they think about the next phase of ownership.
A Reality Check: Understanding the Trade-Offs
One thing I’m careful about sharing is that no strategy is perfect, and none should be viewed in isolation.
Structures like DSTs and other alternative investments come with real considerations. They are typically illiquid, often designed to be held for a defined period, and investors generally give up operational control in exchange for professional management. Outcomes depend on the underlying real estate, the financing environment, and the capabilities of the sponsor managing the asset.
Tax strategies also depend on current laws and regulations, which can change over time. What works well in one situation or one year may not be appropriate in another.
That’s why these conversations should never happen in a vacuum. The most effective planning I’ve seen happens when investors, CPAs, attorneys, and advisors work together, evaluating not just potential benefits, but also risks, timing, liquidity needs, and long-term goals.
Understanding both sides of the equation is what allows people to move forward thoughtfully rather than reactively.
Why This Work Matters to Me
That label: “The 1031 DST Guy“, came naturally and what excites me now isn’t just talking about a strategy.
It’s helping someone see what’s possible.
Sometimes that includes a 1031 exchange.
Sometimes it doesn’t.
Often, it means coordinating with CPAs, attorneys, and other advisors so decisions are made deliberately instead of reactively. And occasionally, it opens doors beyond finance, into legacy planning, charitable giving, or simply peace of mind.
A Different Way to Think About Wealth
I still wake up energized by this work because it feels aligned.
Aligned with how people can potentially build wealth with the right advisory guidance.
Aligned with how they want to live later in life.
Aligned with the belief that good planning should create freedom, not complexity.
Real estate doesn’t have to be all-or-nothing.
Taxes don’t have to be an afterthought.
And planning doesn’t have to feel like giving something up.
That belief is what led me here, and why I continue doing this work today.
Plan for income and legacy with confidence.
If you or someone you know needs guidance on tax-efficient investing strategies, 1031 DST Group is here to help. Learn more or schedule a free consultation at: https://www.1031dstgroup.com/free-consultation Or Download our free eBook: The 1031 DST Advantage: A Strategic Tax Deferral Guide for Financial Professionals. → Get the eBook.
Disclosure:
Portions of the written content in this article were assisted by artificial intelligence (AI) technology tools and reviewed by 1031 DST Group for quality and compliance. This material is provided for educational and informational purposes only and is not intended as investment advice or a recommendation to buy or sell any security. A 1031 exchange may not be suitable for all investors and may involve risks, including the potential for loss of principal. Always consult with a qualified tax advisor or financial professional. Some investments such as Alternative investments and DSTs involve significant risks and may be illiquid, speculative, and suitable only for accredited investors. Accredited investors are defined under SEC Rule 506 of Regulation D. Generally, an investor is deemed accredited if their net worth is greater than $1,000,000 exclusive of their primary residence and/or their annual income exceeds $200,000 for the current and past two years. Click here to learn more.
Ray DeWitt is a Registered Representative of Realta Equities, Inc. and an Investment Advisory Representative of Realta Investment Advisors, Inc. Investment Advisory Services are offered through Realta Investment Advisors Inc., an SEC registered investment advisor. Securities are offered through Realta Equities, Inc., Member FINRA/SIPC. Neither Realta Equities, Inc. nor Realta Investment Advisors Inc. is affiliated with C-Suite Network Or 1031 DST Group. Realta Wealth is the trade name for the Realta Wealth Companies. The Realta Wealth Companies are Realta Equities, Inc., Realta Investment Advisors, Inc., and Realta Insurance Services, which consist of several affiliated insurance agencies.
