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 [email protected]

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.

The real estate investors who are thriving in today’s market are the ones who ignored the pressure to buy questionable deals during the boom years. While many operators fell for floating-rate debt, banked on unrealistic rent growth, and underwrote for best-case scenarios, a more “patient” group focused on the fundamentals.

Hannah Hammond, founder and CEO of the capital advisory firm and commercial mortgage brokerage HB Capital, has a unique vantage point on this dynamic. Through thousands of relationships with operators and lenders nationwide, she sits at the intersection of capital markets and commercial real estate investing. Not to mention, Hannah has scaled her own multimillion-dollar residential real estate portfolio.

But the principles that guide her investment decisions today were shaped by more than market cycles. Raised in a family that struggled financially, Hannah believed money was the key to peace, happiness, and opportunity. This was only partially true. What she discovered after quitting corporate America for entrepreneurship, starting multiple businesses, and achieving financial freedom was that real “wealth” had much more to do with a life rooted in flow, not force.

In today’s conversation, she shares about the painful experiences that shaped her, lessons from failed partnerships, and why the “disciplined” investors from a few years ago are the ones capitalizing on opportunities emerging from market distress.

Insights from today’s episode:

• Hannah’s personal journey from financial hardship to financial freedom
• Why Hannah quit her comfortable engineering career to go all-in on real estate
• Lessons learned from failed partnerships and risky private lending experiences
• How Hannah’s engineering background has influenced her underwriting and risk tolerance
• The three fatal mistakes that cause operators to go underwater on assets
• Why true wealth stems from being fully aligned with your values and purpose—not money
• How to craft a daily routine that allows you to live through flow, not force

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Connect with Hannah on Instagram

HB Capital

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.

00:00 From Scarcity to Abundance

04:09 Quitting Corporate at 21

06:15 Where Operators Are Winning

12:17 Inside the Phoenix Market

18:56 Taking "Calculated" Risks

21:59 Learning from Loss & Failure

25:44 Launching HB Capital

30:08 Attracting Top Talent

34:58 What Is Real "Wealth"?

41:18 Hannah's Daily Routine

45:43 The Next 5 Years

49:36 Connect with Hannah!

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.

Real estate has arguably been the largest wealth generator in history, but for many years, most opportunities have been out of reach for those without large bank accounts.

Alex Blackwood is on a mission to change that with fractional real estate. While working at Goldman Sachs’ private equity group and delivering 15%-20% annual returns to investors, he started dreaming of a company that would lower the barrier to entry and bring these opportunities down to the average person.

In 2022, that dream became a reality when he launched Mogul, a real estate investing platform that allows users to buy fractional shares of residential properties in a matter of clicks. Think Airbnbs in vacation markets, quadplexes with long-term tenants, and even single-family homes that are rented by the room.

With new offerings weekly, investment minimums of just $250, and all the benefits of direct ownership—but without any of the normal landlord responsibilities—everyday people can now buy affordable shares of rental properties in top markets across the U.S.

Whether you’re a seasoned investor or just beginning your journey, this conversation will challenge what you thought was possible with real estate investing and the resources required to build real, long-term wealth.

Insights from today’s episode:

• Why Alex left Goldman Sachs to start a fractional real estate investing platform
• How to reap all the benefits of rental property ownership without being a landlord
• The Mogul “model” that delivers higher annual returns than many REITs
• Residential real estate opportunities with $250 investment minimums
• The high-ROI real estate markets Alex and his team are targeting across the Sun Belt

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Connect with Alex on LinkedIn

Mogul

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.

00:00 Intro

01:21 What Is the Mogul "Model"?

06:22 Managing the Properties

09:06 High-ROI Sun Belt Markets

16:03 Mogul Property Performance

21:50 Advantages Over REITs

26:28 Weathering the Airbnb "Storm"

34:03 Investing with $250!

35:26 Connect with Alex!

Industrial real estate might look simple from the outside. You buy a large box, lease it out, and collect rent. But like with any asset, you can lose your shirt just as easily as you can make a fortune.

Joel Friedland, founder of Brit Properties, understands this better than most. Two years ago, he and his team were bracing for another industry lull, largely driven by high interest rates and sluggish rent growth.

In the industrial space, the opposite happened.

As new construction came to a screeching halt in many of Joel’s markets, supply constraints drove rents higher, particularly for many of his class-B investments.

But that’s just the most recent cycle. Joel’s thesis has been tested repeatedly throughout his 40-plus-year career, and he’s survived it all—not because he’s immune to failure, but because he stuck to fundamentals while the syndicators around him played with fire and got burned.

His no-debt model has made raising capital significantly more challenging, but it’s also helped him weather storms that have wiped out riskier investments. Joel doesn’t use unrealistic pro forma to gain an edge. Instead, he focuses on mitigating risk, playing the long game, and hunting down off-market opportunities most operators don’t have the patience to pursue. It’s helped him win strong deals—and it could help you do the same.

Insights from today’s episode:

• Why industrial real estate has outperformed other asset classes in many markets
• The three biggest red flags Joel avoids on industrial real estate deals
• The economic factors that caused industrial rents to double in the last four years
• Creating an edge in your market with off-market investing opportunities
• Why location and size matter more than the purchase price of industrial buildings
• The conservative approach to leverage that gives you more staying power

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Hear Our Last Interview with Joel

Connect with Joel on LinkedIn

Brit Properties

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, go to InvestWithKB.com 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.
  
  
  
  00:00 Intro
  
  02:00 What Happened to Industrial?
  
  10:20 Creating an Edge
  
  14:37 Joel's "Problem" Property
  
  15:29 The 4 D's
  
  27:46 Managing LP Expectations
  
  35:39 The No-Debt Investing Model
  
  50:48 Biggest Deal "Killers"
  
  54:58 Connect with Joel!
  
  
  

Before you check out episode 993, get up to speed with Building a Resilient Industrial Portfolio: Lessons from Joel Friedland.

In this episode, Joel Friedland, founder of Brit Properties and seasoned industrial real estate operator, shares his journey of transforming his investment philosophy after the lessons learned from the 2008 financial crisis. Discover how a focus on risk control, no debt strategy, and deep tenant relationships have shaped his resilient approach to real estate investing.

• Joel's early entrepreneurial start and entry into industrial real estate
• The lessons learned from the 2008 recession and their impact on his investment philosophy
• The shift from leveraging assets to pursuing low or no debt deals for stability
• How to identify and source industrial properties with strong tenant stickiness
• Strategies for deal structuring, including sale-leasebacks and niche tenant focus
• The importance of location, layout, and deal assumptions in industrial real estate
• Current market conditions and outlook for distressed assets and overbuilding risks
• Joel’s vision for the next three to five years, emphasizing stability and long-term value

Hear Our Last Interview with Joel

Connect with Joel on LinkedIn (https://www.linkedin.com/in/joel-friedland)

Brit Properties (https://www.britproperties.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, go to InvestWithKB.com (http://investwithkb.com/?utm_source=podcast&utm_medium=shownotes&utm_campaign=rei4cf&utm_content=ep993) 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 (https://kevinbupp.com/join/) 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 (https://kevinbupp.com/join/)!
• 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.

00:00 - Introduction to Joel Friedland and his investment philosophy
00:58 - Joel’s entrepreneurial beginnings and early real estate experience
01:44 - Lessons from the 1981 leasing market and mentorship influence
04:16 - Transition from brokering to property ownership and syndication
05:55 - Unpacking Joel's first industrial deal and key learnings
08:07 - The importance of property geometry and tenant needs in industrial
09:34 - Structuring early deals: legal and investor considerations
11:05 - Managing vacancy and lease strategy to attract user buyers
12:48 - Why the property was vacant and how tenants are typically found
14:19 - Impact of the 2008 recession and Joel’s personal and business recovery
16:38 - The shift to no-debt or low-leverage investing post-2008
17:35 - How Joel evaluates risk and manages investor expectations
20:06 - Market evolution and current overbuilding concerns
22:24 - Stress cracks in the real estate market and risk mitigation
24:39 - Market segments Joel is focusing on for stability
26:21 - Tenant-centric strategy and exit paths for industrial buildings
27:46 - Sale-leaseback opportunities and niche tenant strategies
30:22 - The ideal size and price points for industrial properties today
32:23 - Market catalysts that could challenge the industrial sector
34:58 - Overbuilt assets and overbuilding risks in large distribution centers
37:08 - Joel’s business outlook for the next three to five years
39:16 - Approach to deal sourcing and maintaining a conservative portfolio
41:53 - The importance of location, fundamental quality, and timing in industrial investing
42:22 - How to connect with Joel and stay updated on his ventures

Many real estate operators assume institutional capital is simply retail capital at a larger scale: fewer investors, bigger checks.

It’s not.

What they’re missing is that institutional capital often requires you to build more infrastructure, create tighter procedures, and relinquish some control of the asset itself.

The question is: Is the consolidation you get from institutional capital worth all the extra effort?

If you ask John Azar, founder and CEO at Peak 15 Capital, it depends. For the operator who’s growing steadily, tackling smaller multifamily deals, and having no trouble sourcing capital from dozens and sometimes hundreds of limited partners (LPs), perhaps not.

But for the investor who has the means, it can immediately level up their business.

As a liquidity provider for real estate sponsors, John is helping unlock some of these institutional-level opportunities. He shares how to make the jump from retail capital, how to underwrite passive and active investing opportunities properly, and what LPs must do to avoid getting burned by bad operators in 2026 and beyond.

Insights from today’s episode:

• The infrastructure operators must build out before delving into institutional capital
• Why institutional capital isn’t automatically a better option than retail capital
• John’s two biggest lessons learned across a multi-decade career in real estate
• Why the quality of the sponsor matters more than the quality of the deal itself
• What passive investors must do to avoid getting burned by bad sponsors

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Connect with John on LinkedIn

Peak 15 Capital

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.
  
  
  
  00:00 Intro
  
  01:47 Is Institutional Capital Better?
  
  09:57 “Upgrading” Your Business
  
  16:44 Preparing for Institutional Capital
  
  24:09 Recent Syndication Challenges
  
  35:26 What Is Peak 15 Capital?
  
  45:27 How to (Properly) Vet Sponsors