Real Estate Investing for Cash Flow with Kevin Bupp

Real estate investors spend years mastering skills like analyzing deals, raising capital, and improving operations, but far less time thinking about one of the most important decisions they’ll ever make: the exit.
Mike Hart, chief financial officer here at Sunrise Capital Investors, believes you should start planning your exit roughly a year prior to the actual sale, as this affects when you’ll pay taxes, what you’ll pay, and depending on the strategy, if you’ll pay at all.
With over 30 years of commercial real estate experience, Mike has helped countless investors make smarter capital allocation and tax-efficient investing decisions. In this conversation, he unpacks some of the best real estate tax strategies used to defer capital gains tax and depreciation recapture, starting with the well-known 1031 exchange.
He also breaks down some lesser-known alternatives, including Delaware Statutory Trusts (DSTs), and explains how they can help investors transition from active property management to passive ownership while continuing to defer taxes.
Whether you’re looking to peel back from being a hands-on operator or preserve your wealth, this discussion will help you think more strategically about your next sale.
Insights from today’s episode:
The best strategies for deferring capital gains taxes and depreciation recapture
The number one mistake real estate investors make when planning their exit strategy
How to pivot from active owner to passive investor with a Delaware Statutory Trust (DST)
Key rules and deadlines to be aware of before doing a 1031 exchange
How to perform due diligence on a DST trustee before committing capital
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Connect with Mike on LinkedIn
Recommended Resources:
If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team. 
Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!
Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com. 
Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.
Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.

Many get into real estate with the goal of scaling a massive portfolio. Not enough stop to ask whether they should. The truth is that success doesn’t come from chasing every last opportunity. It’s about identifying where you have an edge, choosing your partners carefully, and having the discipline to walk away when a deal doesn’t quite fit.

John McNellis is the founder of McNellis Partners and author of the commercial real estate classic, Making It in Real Estate. Over the course of a 50-year career, he’s completed roughly 100 real estate deals—most of which have been ground-up commercial development projects. Through thick and thin, John has stuck with retail real estate—even while others were predicting its downfall—and the asset class has made him very wealthy.

But stay in real estate for long enough, and you’re bound to lose money. John opens up about the disastrous deal that nearly wiped him out, the three critical mistakes that caused it, and why he no longer works with big financial partners on his development deals. He also discusses the biggest mistakes new real estate developers make early in their careers and the million-dollar question every investor is trying to answer: what is “enough”?

Insights from today’s episode:

How John scaled a large commercial real estate portfolio through strategic partnerships

Crucial lessons learned across a 50-year real estate development career

When to stop accumulating assets and start pruning your portfolio

How retail real estate has evolved over the last few decades

What to know before structuring an investing partnership

The three most common mistakes made on commercial development deals

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Making It in Real Estate

Connect with John on LinkedIn

McNellis Partners

Recommended Resources:

If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team. 

Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!

Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com. 

Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.

Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.

One of the biggest mistakes investors make is confusing uncertainty with risk. When a deal looks “messy,” most operators walk away. They treat temporary problems as if they’re permanent and, in the process, overlook some of the greatest investing opportunities.
Today, I’m bringing you another Sunrise Capital Investors case study: the Meadows of North Lewisburg and South Towne Meadows, a pair of manufactured housing communities roughly 30 minutes outside downtown Columbus, Ohio.
On the surface, this 323-unit portfolio looked like a complicated deal with questionable management and an inflated asking price. Not to mention, most of these sites were park-owned homes, something that would usually fall outside our buy box. But rather than writing the property off, we identified its biggest “weakness” as a potential value-add opportunity.
When other investors passed on this $20,000,000 deal due to its perceived risk, we trusted our numbers, backed in our leadership, and got to work.
Nearly three years later, these two communities have already become some of our portfolio’s strongest performers, with NOI, occupancy, collections, and rents all outperforming our initial projections. But we didn’t get lucky. I’m sharing exactly how our team pulled this off, the biggest hurdles we had to overcome along the way, and what far too many operators get wrong: that strategy without execution is just theory.
Insights from today’s episode:
Case study: our $20 million manufactured housing deal in Columbus, Ohio
Why these communities are performing 15% above projections
The one thing you can’t fix about a property after purchasing it
How to mitigate perceived risk with “conservative” deal analysis
Turning an asset’s “weakness” into its biggest value-add opportunity
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Ridgebrook Hills MHP Case Study
Real Deals: The Biggest Mobile Home Community We’ve Ever Bought | Ep. 990

Imagine owning a property with enormous upside, but one that’s operationally complex and requires hundreds of thousands or even millions in capital improvements. What do you do? Selling leaves value on the table. A joint venture dilutes control and introduces unnecessary risk. So what’s the alternative?
One of commercial real estate’s most underutilized capital structures: the ground lease.
Danielle Ash, partner and co-chair of the ground lease practice at Adler & Stachenfeld, has helped countless investors generate predictable cash flow, preserve long-term ownership, and even unlock trapped equity with this often-overlooked strategy.
She unpacks the three main “buckets” of ground leases, along with the sale-leaseback option that allows owner-operators to create liquidity for other projects. Danielle also shares a real-world case study involving a New York City property with massive potential and a $200 million renovation, managed and paid for by the lessee. 
Whether the goal is to free up capital for future acquisitions or create a long-term passive income stream while benefitting from capital improvements, the ground lease is a powerful tool worth exploring.
Insights from today’s episode:
How to create long-term cash flow with commercial ground leases
A real case study of a New York City ground lease deal involving a $200 million renovation (paid by the lessee!)
The biggest risks to consider before entering into a ground lease agreement
Why a ground lease is often a win-win for both owner and operator
What lenders look for when underwriting ground lease tenants
How owner-operators can create liquidity through sale-leasebacks

When investors hear the term USDA loan, they tend to picture small towns, farmland, and niche financing. In reality, they may be overlooking one of the best—and least understood—government-backed loan programs available for commercial real estate.

In many cases, the USDA loan is an even better option than both the SBA loan and conventional financing. To explain why, we’re joined by Jordan Blanchard, commercial lending expert and co-founder of X-Caliber Rural Capital. With more than 30 years of banking and lending experience, Jordan has built a career out of helping investors unlock borrowing opportunities—like USDA financing—many don’t realize exist.

Jordan unpacks the loan’s biggest advantages and trade-offs while dispelling the biggest misconceptions surrounding it. He also shares exactly what investors need to know before applying, as well as how to layer other financing options and tax credits into an efficient capital stack.

There’s no sugarcoating it: USDA loans can be difficult to qualify for. But for investors needing large amounts of capital, flexible terms, and a lower-money-down alternative to conventional financing, the payoff is well worth it.

Insights from today’s episode:

USDA loans—how they work, who they’re for, and common misconceptions

How to quickly determine if you’re eligible for a USDA loan

USDA versus SBA versus conventional financing (pros and cons)

The ideal capital “stack” for funding commercial real estate deals

Inside the $185 million deal Jordan and his team recently closed

The five most common reasons why operators default on commercial loans

00:00 Intro

03:05 USDA Lending 101

08:12 2 Common Misconceptions

11:52 Longer, More Flexible Terms

14:36 Creating Your Capital "Stack"

21:20 Who Is USDA-Eligible?

22:55 Biggest Investor Mistakes

32:08 5 Rapid-Fire Questions!

35:42 Connect with Jordan!

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Connect with Jordan on LinkedIn

 

X-Caliber Rural Capital

Email Jordan at jordanb@xrcusda.com

Recommended Resources:

If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, click here for opportunities to invest in real estate projects alongside Kevin and his team. 

Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club!

Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com. 

Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.

Disclaimer: This podcast is for educational purposes only and does not constitute financial, tax, or legal advice. Consult with a qualified professional before making any investment decisions.