Real Estate Investing for Cash Flow with Kevin Bupp

This could be one of the highest ROI strategies in real estate, yet most investors ignore it.

Imagine getting hundreds of thousands of dollars in write-offs, saving tens of thousands in taxes, all while you own income-producing, equity-building real estate. Most investors think they know what we’re talking about in today’s show, but if they did, they’d be jumping at the chance to use it.

It’s no secret—cost segregation studies can become one of the most profitable weapons in your real estate investing arsenal. If you think your property is too small, too old, or too cheap to use one, Kim Lochridge, Executive Vice President for Engineered Tax Services, plans to prove you wrong.

Kim and her team conduct over 800 cost segregation studies a month on properties ranging from five-figure rentals to multimillion-dollar assets. She’s answering every question: What is a cost segregation study? How much does a cost segregation study cost? How much can you write off? Plus, why passive investors can unlock a treasure trove of paper losses, even if they’re still working a W-2 job.

That’s not all. Kim shares the most tax-advantaged assets investors can’t ignore, and the audit red flags she learned from a nightmare encounter with the IRS. 

This isn’t just about saving on taxes; this is about unlocking tens of thousands in tax savings that materially improve cash flow.

Insights from today’s episode:

Cost segregation studies explained: what they are, how much they cost, and who can use them

The five most tax-advantaged assets with massive bonus depreciation potential 

Audit red flags and an easy way to protect yourself from the IRS

The “lazy 1031 exchange” that eliminates the tight timeline to find and buy a property 

How passive investors can mitigate tens of thousands in taxes with cost segregation studies (you don’t need to be a real estate professional) 

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Connect with Kim on LinkedIn

Engineered Tax Services

Real Estate Investing for Cash Flow 230 - Cost Segregation Explained – with Kimberly Lochridge

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow 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!

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

Everyone plans to “buy the dip” until it’s time to write the check.

Multifamily opportunities are rising, and with properties 20%+ off the peak of pricing, investors are getting flooded with “deals.” But, like we learned over the past five years, the wrong sponsor (even with the right deal) can kill your returns and blow up the wealth you spent so long to build. 

So, how do you spot the opportunities vs. the landmines in multifamily? We brought on fund of funds manager, Lon Welsh, to share his sponsor-vetting checklist. 

With decades of experience in real estate investing, launching his capital fund in 2022 could have been disastrous (rising interest rates, rent growth freezes, expanding cap rates), but to this day, Lon has over a 90% success rate across funds within his own fund. This wasn’t done by guessing or gut-checks, but carefully choosing the right sponsor for the right deal.

Today, Lon shares his own sponsor-vetting checklist, how he personally confirms a deal is worth getting into, the best multifamily markets in the country with easing supply, low regulation, and strong demand, and how to ensure a sponsor was intentional, not lucky, in achieving their past successes. 

Plus, we even get Lon’s multifamily prediction for 2026-2027.

Insights from today’s episode:

How to vet a multifamily sponsor before putting a dollar into their deal

Why a “fund of funds” could be the more diversified, safer bet than real estate syndications 

What to look at to ensure a sponsor wasn’t just “lucky” during past deal cycles 

The best places to invest in multifamily right now (2026) where supply is about to drop off

How to feel confident buying during a dip when everyone else is too scared to act 

Lon’s medical receivables play making passive income without a single property 

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Connect with Lon on LinkedIn

Ironton Capital

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow 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!

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. 

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.

This could be commercial real estate’s “buy of the decade,” according to a 35-year investing veteran. This asset class is seeing rock-bottom prices, shrinking supply, and acquisitions at a quarter of replacement cost.

Everyone says this asset is dead, so why are expert investors, lenders, and brokers betting on it?

Michael Bull, founder & CEO of Bull Realty, Inc., has personally overseen over $8 billion in commercial real estate transactions in his 35 years in the industry. He’s seeing sentiment shift toward one forgotten asset class office space investing. Office investments are seeing supply get actively demolished, but lending and buying are returning, and some cities are even seeing more office demand. 

The media is saying it’s all doom and gloom, but on the ground, Michael is seeing something very different.

Want to buy when the fear is still high, but prices are touching bedrock? Michael shares his underwriting playbook for finding valuable office investments, what savvy operators are doing with outdated office vintages (demolish, rebuild, or retrofit?), and the markets with the most opportunity for demand. Plus, the exact type of tenant that is giving those who invest in office space consistent revenue and unmatched peace of mind.

Insights from today’s episode:

Commercial real estate’s “buy of the decade” and why investors are jumping back in

No new supply coming online? Why office building supply is shrinking, just as demand bounces back 

Underwriting “guardrails” experts use to validate a valuable vs. dead office investment 

First office investment? Where Michael says beginners should start looking for opportunities  

Falling values = falling property taxes? An even bigger lever for cash flow 

Retrofit, rehab, or convert? How to add value to old, outdated office vintages 

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Connect with Michael on LinkedIn

Buy or Sell with Bull Realty

America’s Commercial Real Estate Show Podcast

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow 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!

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. 

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.

Just over five years ago, express car washes were peaking. Private equity was getting in, ready to buy up these cash-flowing projects at high prices. At this moment, Ben Salzberg and Bill Kanatas knew it was time to get out and pivot toward an even more durable asset.

What did they turn to? Self-storage, and not your average mom-and-pop shop. Class-A, climate-controlled, multi-story facilities that self-storage REITs could easily come in and run. It’s a blueprint that has worked for them for five years plan, consult, construct, and let the 3rd-party self-storage management team take care of the rest. But there’s much more to this strategy than building a pretty box.

On today’s show, Ben and Bill outline the exact blueprint they use to build REIT-ready self-storage facilities, how to work with big names (Public Storage, Extra Space, CubeSmart) before you lay a single brick, what to look for in a market before you decide to build, and why entitling land, turning dirt into dollars is more worth it than you think. Plus, Ben and Bill share the optimal storage facility size (and demand ratios) so you know what REITs and customers want.

Insights from today’s episode:

A REIT-ready self-storage development blueprint from 30-year development veterans

The 3rd-party self-storage management that instantly plugs into your facility 

Why Ben and Bill left cash-flowing car washes for class-A self-storage facilities 

Signs a market is too saturated with self-storage (and what to look for instead)

Getting the city on your side—how to create a win-win for local government, residents, and your investment 

Entitling land—is it worth the effort to turn raw dirt into a buildable lot?

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Connect with Ben on LinkedIn

Connect with Bill on LinkedIn

Work with Self Storage Developers 

Email Self Storage Developers: [email protected] 

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow 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!

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. 

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/Podcas

Every multifamily operator wants to know how to increase NOI, but they’re not doing it the right way. Traditional renovations leading to rent increases have been harder to get right in the past few years. But what if there was a “hidden” source of not only higher revenue but also lower expenses—something 99% of operators are unaware of, that could increase NOI by tens of thousands per month.

Today, Bill Douglas of OpticWise (https://www.opticwise.com/) and Marcy Sagel of MSA Interiors (https://msainteriors.com/), CRE technology and design experts, join us to talk about the NOI levers nobody is thinking of pulling. We’ll share the actual amenities and tactics you can use today in your building to attract higher-paying tenants and turn utility expenses into revenue, with game changing effects on your bottom line. Plus, what buy-and-hold vs. short term flip investors must include in their budget to get the maximum NOI possible. 

One amenity our experts say is an actual waste of money…unless you hear how to monetize it properly. 

Retrofitting an older vintage multifamily? Bill and Marcy share exactly how to track which design changes are working for your bottom line, how to go from antiquated to next-level tech, and the hidden value-add opportunities you can implement starting today. Plus, why your property management company could be stopping you from making tens of thousands more every month! 

Insights from today’s episode:

The “hidden” NOI opportunities that most multifamily operators completely miss 

One amenity you can provide that could increase your revenue $80-$90 PER unit

The design tweaks younger renters require that move the needle on NOI 

An expert checklist on renovating and retrofitting 1980s vintage to today’s standards 

Data you can start collecting now that shows precisely what tenants want/don’t 

The best piece of advice for anyone building a new multifamily (could boost your NOI) 

Connect with Bill on LinkedIn (https://www.linkedin.com/in/billdouglas/)

OpticWise (https://www.opticwise.com/)

Grab Bill’s Book, Peak Property Performance (https://www.peakpropertyperformance.com/)

Listen to Bill’s Peak Property Performance Podcast (https://podcasts.apple.com/us/podcast/peak-property-performance/id1817250978)

Connect with Marcy on LinkedIn (https://www.linkedin.com/in/marcysagel/)

MSA Interiors (https://msainteriors.com/)

Recommended Resources:

Accredited Investors, you’re invited to Join the Cashflow 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/)!

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. 

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.