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Real Estate Investing for Cash Flow with Kevin Bupp

#905 From Piggy Banks to Passive Profits: The Road to STR Resilience

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp

Reit, Consultant, Syndication, Seniorliving, Retail, Kevinbupprealestate, Acquisitions, Realestate, Selfstorage, Donaldtrump, Assistedliving, Apartmentinvesting, Flow, Shoppingcenter, Kevinbupp, Coach, Investing, Kevinbuppflorida, Foreclosure, Realestateinvesting, Cashflowinvesting, Office, Business, Entrepreneur, Cashflow, Commercial, Real, Industrial, Education, Mergers, Trainer, Shortsale, Millionaire, Investments, Privatelending, Legacywealth, Funding, Podcast, Multifamily, Broker, Estate, Apartments, Commercialrealestate, Experts, Mobilehomeparks, Cash, Privatemoney, Valueadd, Hedgefund, Robertkiyosaki, Defaultedpaper

4.9675 Ratings

🗓️ 2 June 2025

⏱️ 42 minutes

🧾️ Download transcript

Summary

We’re diving deep into the world of short-term rentals—Airbnbs, vacation properties, and everything in between. Everything from market saturation, competition from hotels, bad reviews, regulatory threats, operational pit falls, and what Quentin West believes about the long-term viability of this model. Quentin has built a sizable portfolio of short-term rentals across multiple markets. He’s seen the good, the bad, and the ugly of this business model—and today, he’s pulling back the curtain to share the lessons he’s learned the hard way.

Connect with Quentin: IG @qdealshomes

Free Course: Text SUPERHOST to 26786

Highlights:

3:00 - Quentin'  Creative Hustle

5:45 - Real Numbers Behind STR Arbitrate

11:00 - Scalable  Low-Capital Model

18:00 - Golden Triangle Method

32:00 - Mitigating Platform Risk

37:00 - Avoiding Failure

 

Quote: “I went from borrowing quarters from my kids’ piggy bank to rebuilding a six-figure business by optimizing my listings—one change at a time.”

 

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.

Transcript

Click on a timestamp to play from that location

0:00.0

You've been searching for the best way to generate passive income in your life and heard that real estate is a great way to do it.

0:09.4

But you're tired of all the so-called gurus who are all talk and no substance.

0:15.3

Get ready to celebrate because Kevin Buck has spent 14 years successfully making it happen.

0:21.7

This is the Real Estate Investing for Cash Flow podcast.

0:25.2

Now, here's Kevin Bup.

0:30.6

Hey guys, Kevin Bup here, and I want to welcome me to another episode of the Real Estate

0:34.1

Investing for Cashflow podcast.

0:35.6

We're missions to help you build and maintain massive amounts of cash flow through income producing real estate investments.

0:42.1

Now, our guest for this week show is real estate vacation rental expert Quentin West.

0:46.3

Now, today we're going to be diving deep into the world of short-term rentals. You guys,

0:50.4

Airbnb's vacation properties, VRBO, and really everything in between, right?

0:55.4

Like you guys know the space, understand it.

0:57.4

But we're not just here to talk about, you know, how great the returns can be.

1:01.6

We're going to dive a little deeper, in fact, quite a bit deeper.

1:04.8

And we're going to shy away from, you know, returns and things and all that.

1:07.8

We're going to talk about everything, you some of the bad stuff right some of the challenges that that we all face as business owners you know things like

1:14.1

market saturation competition from hotels bad reviews you know what does that mean for

1:19.6

for someone that owns Airbnbs all the way down to like regulatory threats like with the ever

1:24.7

changing environment lots of markets have put restrictions in place on short-term rentals.

1:29.8

There's various operational pitfalls and, you know, really I just hopefully will get a broad perspective from

1:35.5

Quentin as to, you know, how he feels about the long-term viability of the, you know, STR, short-term rental model.

1:41.9

Now Quentin has, he's built a sizable portfolio of short-term rentals across multiple

...

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