EP223 Is It Time To Sell Your Rental Properties? Roundtable Discussion with Ben Blake, Jeremy Schumann and Justin Workman

EP223 Is It Time To Sell Your Rental Properties? Roundtable Discussion with Ben Blake, Jeremy Schumann and Justin Workman

Back in the pre-covid-19 days when people could actually sit together in the same room, a group of rental property owners met to answer one simple question: "When is it time to sell your rental property?" Even though the world has changed considerably since then, the answers they came up with still hold true today.

Let's say you've acquired a decent sized portfolio of rental properties, they're cash flowing, well-managed, and achieve your goals of long-term wealth. But maybe the cash flow you're receiving isn't enough to allow you to quit your job, or retire early, or pay for that cruise ship vacation. However, there is enough equity in your portfolio to sell for a substantial profit.

Is it time to sell and take your chips off the table? Or are you better served to stay on the 'buy & hold' path that you set out on so long ago?

Many investors are faced with this very question, and I have two of them in the studio with me today. Plus, I have a very special guest who's going to help us talk through this very important decision-making process.

My first guest is Ben Blake, and when he was last on the show, episode #149, he discussed his 12-unit Grand Rapids portfolio, and why he decided to take over the management himself. Ben recently sold his entire portfolio, and today we're going to learn why.

Also in the studio is Jeremy Schumann, who owns a 13-unit portfolio here in Grand Rapids, Michigan. Jeremy is currently trying to decide whether he should hold or sell, and we'll be talking through that decision with him.

And friend of the show, Justin Workman, is joining us as well. Justin always lends a mathematical and informed perspective on these types of decisions, and I'm sure he'll balance out any opinions I might have as the four of us go through the different thought processes and cashflow and appreciation calculations a rental owner must consider before selling their investment property.

And visit our show on Facebook to leave comments and ask questions by going to "RPOA Rental Property Owner & Real Estate Investor Podcast"

Avsnitt(589)

Boring but Profitable: How Midwest Workforce Housing Beats Hype Markets with Jeremy Yost

Boring but Profitable: How Midwest Workforce Housing Beats Hype Markets with Jeremy Yost

Many Sunbelt markets that once dominated headlines are now facing oversupply, rising expenses, and compressed returns. Meanwhile, much of the Midwest is quietly doing the opposite — holding occupancy,...

6 Apr 33min

Creative Financing in 2026: Zachary Beach's MREIC Speaker Spotlight

Creative Financing in 2026: Zachary Beach's MREIC Speaker Spotlight

Zachary Beach is next up in our 2026 MREIC Speaker Spotlight series. Zachary breaks down why creative financing is becoming more important in today's market. As CEO and Partner of SmartRealEstateCoach...

2 Apr 6min

Why Most Airbnbs Fail: Using Data to Pressure-Test Short-Term Rental Deals with John Bianchi

Why Most Airbnbs Fail: Using Data to Pressure-Test Short-Term Rental Deals with John Bianchi

Most Airbnb failures don't come from bad luck. They come from bad assumptions made before the deal ever closes. In this episode, John Bianchi, founder of STR Search, breaks down how he evaluates short...

30 Mars 29min

Speaker Spotlight: Anthony Chara on Apartment Investing Opportunities in 2026 | MREIC 2026

Speaker Spotlight: Anthony Chara on Apartment Investing Opportunities in 2026 | MREIC 2026

Anthony Chara joins the Midwest Real Estate Investor Conference Speaker Spotlight to talk about why multifamily investing deserves serious attention in 2026. In this conversation, he breaks down what ...

26 Mars 6min

When Real Estate Becomes Dead Capital: 1031 Exchanges, DSTs, and Smarter Exit Planning with Dan Ihara

When Real Estate Becomes Dead Capital: 1031 Exchanges, DSTs, and Smarter Exit Planning with Dan Ihara

At some point, every real estate investor has to ask a hard question: Is this property still working for me, or am I just holding it out of habit? In this episode, Dan Ihara, a national real estate pl...

23 Mars 28min

Steve Brown Keynote Preview: The State Of AI And What It Means For Your Business—MREIC 2026

Steve Brown Keynote Preview: The State Of AI And What It Means For Your Business—MREIC 2026

AI is no longer theoretical. It is already changing how real estate decisions get made in underwriting, leasing, operations, marketing, asset management, and communication. In this special episode, I ...

16 Mars 30min

MREIC 2026 Speaker Spotlight: Paul Moore—The Boring Investor: Build Real Estate Wealth Without Drama

MREIC 2026 Speaker Spotlight: Paul Moore—The Boring Investor: Build Real Estate Wealth Without Drama

Paul Moore is coming to MREIC 2026 with a message a lot of investors need right now: the path to long-term wealth isn't exciting—it's durable, disciplined, and often "boring." In this Speaker Spotligh...

12 Mars 8min

Finding Hidden Value Through Hyper-Local Investing and Relentless Curiosity with Dr. Jordan Romano

Finding Hidden Value Through Hyper-Local Investing and Relentless Curiosity with Dr. Jordan Romano

Dr. Jordan Romano is an Ivy League–trained physician who has built a strong real estate portfolio not by chasing headlines or spreadsheets—but by going extremely hyper-local, staying curious, and lear...

9 Mars 31min

Populärt inom Business & ekonomi

framgangspodden
varvet
badfluence
svd-tech-brief
rss-jossan-nina
rss-borsens-finest
uppgang-och-fall
avanzapodden
bathina-en-podcast
rss-svart-marknad
fill-or-kill
lastbilspodden
borsmorgon
rss-inga-dumma-fragor-om-pengar
tabberaset
rss-dagen-med-di
rikatillsammans-om-privatekonomi-rikedom-i-livet
24fragor
affarsvarlden
rss-den-nya-ekonomin