Real Estate Investing for Cash Flow with Kevin Bupp

Some commercial real estate investments don’t look like obvious winners on the surface. Complexity, uncertainty, and unanswered questions scare many investors away, but they can also lead to some of the best opportunities. That was certainly the case with the deal I’m about to show you: a great asset, in a great location, with more than a few hurdles along the way.

 

Today’s Sunrise Capital Investors case study involves a $33.2 million parking garage in Clearwater Beach, Florida. This was one of the most complex projects we’ve ever taken on, but through conservative underwriting and a figure-it-out mentality, we turned a complicated acquisition into one of the best-performing assets in our entire portfolio.

 

The deal required us to purchase the property in phases, coordinate with two different sellers, and navigate a nerve-wracking bidding process. Yet on the other side of these challenges was a unique asset that now generates millions in annual revenue. I’m breaking down all of the numbers, how we negotiated a triple-net lease with a corporate-level guarantee, and the value-add initiatives that increased the property’s value by over $15 million in year one.

Insights from today’s episode:

Case study: the $33 million Clearwater Beach parking garage deal

Three takeaways from this complicated commercial real estate deal

How to find off-market opportunities without cold calling or sending direct mail

The immeasurable value of networking and nurturing industry relationships

How to get a head start on value-add opportunities before you close

The complexities of purchasing one asset from two owners

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Read the North Beach Parking Plaza Case Study

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.

Chapters: 

00:00 Intro

02:47 Finding the Property

05:52 Why We Liked It

11:32 The Bidding Process

15:27 Triple Net Lease Negotiations

19:44 Value-Add Opportunities

22:04 Numbers on the Deal

25:48 Property Performance

28:43 3 Biggest Takeaways

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.

Commercial real estate acquisitions doesn't simply mean finding a deal, underwriting it, and hoping for the best. Often, having the discipline to act on what you find will make you wealthier than even the greatest properties you could buy. Every investment has skeletons in the closet, and even if the problems you inevitably uncover are fixable, some just aren’t worth fixing. So when do you draw the line even after you’ve fallen in love with the deal?

Today, I’m speaking to my partner and CEO of Sunrise Capital Investors, Brian Spear. We started as a two-person team, running everything from acquisitions and due diligence to operations and value-add. Now, our team has grown substantially, and we’ve acquired nearly $500M in properties that fit our buy box and provide peace of mind to our investors.

Even after decades in the investment property and commercial real estate space, we still get stuck. A recent deal looked profitable on paper and had a clear, solvable solution for problems, but it was too much for us to stomach, so we walked away, even with $60,000 spent in pursuit costs. Exiting was a painful but wise move, so how do you know when to do the same?

Today, Brian and I talk about how to run acquisitions the right way, control your investment’s outcome, and explain what happens when a deal's mechanics change while you're under contract. If you can build your system and team to protect against the downside, prepare for upside, and weather the in-between, you can scale smarter than the competition. 

Insights from today’s episode:

When to walk away from a deal even after tens of thousands in pursuit costs 

Why a “solvable” problem is not always worth fixing in a property 

How much can you truly count on infill value-add when acquiring a mobile home park?

How the quality of your mobile home community can dictate how fast you recoup your investment 

Selling properties that were once cash cows due to a changing landscape 

The people are the power: how your team dictates your result on any real estate deal 

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Hear More from Brian on The Sage Investor

Subscribe to Brian’s Channel on YouTube

Connect with Brian 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.

Chapters: 

00:00 Intro

02:33 The "Infill" Upside

05:53 Control Your Investment's Outcome

09:53 Challenging Value-Add (Worth It?)

12:56 When to Walk Away (Real Example)

20:00 Sunk Costs (Gained Knowledge)

22:00 Never Think Short-Term

24:40 When the Budget Gets Blown Up

30:30 Is the Value-Add Worth It?

37:16 Controllable Often Beats "Fixable"

38:56 Selling What Used to Work

42:47 Your Team Controls Your Destiny

49:04 My Sage Acquisition Principle

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.

What separates a piece of commercial real estate that doesn’t survive from one that endures for decades—and through multiple market cycles? It’s a question Ed Pitoniak, founder and CEO of VICI Properties, has spent the last several years working to answer.
Today, Ed leads one of the nation’s largest owners of experiential commercial real estate. But he took an unconventional path to get there, starting at a ski publication before moving into hospitality and, eventually, real estate.
Along the way, he forged the skills and perspective needed to navigate some of the industry’s toughest challenges, from the rising costs of capital to tenant concentration risk. Ed shares how he underwrites real estate deals to account for today’s high-interest-rate environment and the two-part strategy he’s using to slowly but surely diversify VICI’s tenant base.
He also breaks down how his team evaluates not only the properties they acquire but also the triple-net lease tenants occupying them after closing. Plus, Ed shares the thesis behind a real estate category he believes will be one of the more durable asset classes over the next several decades.
Insights from today’s episode:
The real “durability test” for any piece of commercial real estate
How Ed weighs risk and reward when underwriting new opportunities
The biggest challenges when working with triple-net lease tenants
The two-part strategy for mitigating tenant concentration risk
How to vet operator and asset quality before buying a property
Criteria for determining if a real estate category has real staying power
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VICI Properties
Connect with Ed 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.

Chapters: 
00:00 Intro
01:05 Transitioning to Real Estate
06:08 The Birth of VICI Properties
15:04 Property and Operator Quality
20:43 Triple Net Lease Tenants
25:45 Weighing Risk & Reward
30:46 Mitigating Concentration Risk
33:09 The Future of Experiential Real Estate
36:33 The Ultimate Durability Test
41:29 Connect with Ed!
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 investing demands conviction, but when market conditions shift—sometimes even mid-deal—do you stick to your guns or walk away?

 

August Biniaz, CIO and co-founder of CPI Capital, found himself toeing this exact line shortly after underwriting and raising capital for a large, build-to-rent community in Tucson, Arizona.

 

When interest rates spiked, the deal no longer penciled, but exiting meant sacrificing significant time and over $100,000 in sweat equity. On the other hand, moving forward meant potentially putting investor capital, and their reputation, at risk.

 

Rather than rationalizing what had become a “bad” deal, August and his team made the difficult decision to change course and abandon the deal. Had they not, the fund would likely have been wiped out. Instead, CPI Capital has grown to well over $225 million in value-add multifamily and built-to-rent, single-family assets under management in the last several years.

 

In today’s conversation, August shares how these early lessons shaped the way they approach risk and opened the door for even greater investing opportunities.

Insights from today’s episode:

When to walk away from a deal when the numbers no longer work

Why August and his team opted for a co-GP approach on their first few deals

How to stay competitive in large markets as a middle-market operator

How to properly structure a cross-border investment

The main differences between built-to-rent tenants and other renters

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CPI Capital

 

Connect with August 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.

Chapters: 

00:00 Intro

00:47 Pivoting to US Real Estate

10:20 Cross-Border Complexity

15:05 The Co-GP Approach

19:37 Finding Opportunity in Big Markets

25:25 How to Stay Competitive

28:37 The Build-to-Rent Model

34:17 Walking Away (And Losing $100K)

41:41 Advice for New Investors

46:57 What Has Changed?

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.

After more than 50 years in commercial real estate, Bill Cummings has built an 11-million-square-foot portfolio spanning 12 communities around Greater Boston. But he did so by ignoring many of the conventional rules of real estate investing.
When his peers suggested he explore new markets, he stayed local. When others urged him to sell, he continued to hold for decades. And when other developers steered clear of neglected buildings, Bill saw opportunity, transforming overlooked properties for enormous profits.
This contrarian approach hasn’t just helped shape the culture at Cummings Properties; it’s also caused Bill to rethink his entire philosophy about business and wealth. Having arrived at his own definition of “enough” long ago, Bill has since turned his attention to a much bigger purpose: the Cummings Foundation, which has awarded over $650 million in grants to nonprofits throughout the suburbs of Boston and beyond.
But to understand how Bill built an empire, we have to go back to the beginning. In this episode, he shares the early successes, failures, and the simple conversations with his father that influenced his views on price, value, opportunity, and what actually makes a great investment.
Insights from today’s episode:
Why Bill repeatedly buys properties most developers pass up
The $500,000 commercial property no one wanted (that made a fortune)
The key to maintaining high occupancy in commercial real estate
The one type of commercial building Bill refuses to buy
How to define “enough,” and what to do once you reach it
—
Cummings Properties
Cummings Foundation
Starting Small and Making It Big
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.

00:00 Lessons from 50+ Years in Real Estate
05:43 Local, Buy-and-Hold Investing
12:01 Building Strong Culture
16:18 The Property "No One Wanted"
25:59 Bill's Recent Deal
31:14 How to Improve Occupancy
33:13 Property Red Flags
36:20 What Is "Enough"?
40:11 The Cummings Foundation
43:24 Connect with Bill!