In this episode of Cleveland Real Estate Investor, Mike, Brook, and A'marri discuss Match Day, when medical school graduates are placed in residency programs and begin searching for rental housing. This presents a great opportunity for landlords to secure responsible, long-term tenants—young doctors who are focused on their work and need stable housing.
They also explore the changing nature of the rental market, as Airbnb has become oversaturated, with nearly every Tom, Dick, and Harry trying to become a host. With short-term rentals losing profitability, the team discusses shifting to a rental model that falls between Airbnb and traditional long-term leasing. Tune in for insights on how to adapt to these shifts and maximize rental income.
1:30 Brook explains how they analyze their real estate portfolio, deciding which properties are profitable and which ones should be sold.
3:00 Mike shares the backstory of how they got into real estate, starting with their first rental property and transitioning from house flipping to short-term rentals.
5:00 The team discusses the shift away from short-term rentals due to market saturation and why midterm rentals for medical residents on Match Day present a great opportunity.
10:30 Mike emphasizes the importance of tenant screening, explaining why credit scores matter and how bad tenants can lead to financial and property damage.
19:00 A'marri and Brook highlight key rental strategies, including lease structuring and pricing for different rental durations to maximize returns.


Magic Matching Day

Mike and Brook discuss what it really takes to sell a house.
What buyers look for. Some things Reilly Painting and Contracting has done recently to help get their houses sold. How to tell if a buyer is serious.
2:00 Mike introduces the topic of the episode: understanding the real estate market and how it mirrors the stock market in its unpredictability.
4:10 Brook explains how pricing a house correctly is key, emphasizing that condition and location should dictate the price, not just market trends.
6:50 Mike and Brook break down the improvements made to a rental property before selling, including refinishing floors, updating the bathroom, and enhancing curb appeal.
20:30 The team discusses how to spot serious buyers, why fast closings matter, and the importance of reviewing financing terms before accepting an offer.
36:48 Mike and Brook explain the importance of pricing strategy—how to tell if a house is priced too high, when to adjust the price, and how buyers react to price drops.

The Market Is Market

More of a general meeting between A'marri and Brook as they discuss the week, work they have, working with software developers, how to solve problems creatively, qualities needed to manage and lead and much more.
2:00 Mike and Brook discuss their love for the movie Heat and its deeper life lessons beyond crime.
4:20 Mike compares being an entrepreneur to a lifestyle rather than just a career choice.
5:00 Brook explains how "the action is the juice" applies to business—it's the process, not just the payoff.
6:45 Mike discusses the struggles of running a business, making payroll, and financial pressures.
6:30 Mike highlights the importance of financial planning and using spreadsheets to stay afloat.


The Action Is The Juice

Joined by guest John Schloss, Mike and Brook talk the draft and the future of the browns.
3:10 Mike introduces the episode, discussing the Browns' offseason moves and setting the stage for the conversation with John.
7:30 Brook and John analyze the team's draft strategy, debating whether the Browns should focus on strengthening the offensive line or adding depth to the secondary.
15:00 The group dives into quarterback performance, comparing stats and speculating on potential roster changes before the season starts.
27:38 Mike asks John about his favorite Browns memory, leading to a discussion on iconic games and what makes the fanbase so passionate.
40:20 Brook wraps up the episode by sharing listener questions, including predictions for the upcoming season and concerns about coaching decisions.


Draft And The Future Of The Browns

Brook and Mike discuss the power of scripting and planning for quick Airbnb turnarounds and for selling properties.
2:00 Mike introduces the idea of scripting your day and how vital it is for managing real estate and small business operations effectively.
3:00 Brook breaks down how she handles violation lists—deciding what can be done in-house, what needs to be outsourced, and the importance of being proactive before a house closes.
6:15 Mike reflects on the harsh realities of running a small business—juggling subs, maintenance issues, and why passion alone isn’t enough for success.
10:30 Brook explains how organizing work around the weather and staying in close communication with subs can save time, money, and stress.
21:15 Mike shares the three business fundamentals every small business owner should master: sales, creative marketing, and financial literacy.


The Power Of Scripting And Planning

Brook and Mike share their thoughts and opinions on the Cleveland Browns Draft, discussing potential picks, team needs, and what they hope to see from the front office.
1:15 Brook starts draft day talk, asking Mike what he wants to see happen with the Browns, not just what he expects.
3:15 Mike shares why this needs to be a "legacy draft" for the Browns, pointing to historic drafts by teams like the Steelers and Cowboys.
4:30 Brook outlines her dream scenario: drafting Travis Hunter at #2, grabbing a running back or tackle at #33, and landing a promising QB in the later rounds.
6:45 Brook and Mike discuss potential quarterback picks like Jalen Milroe and the value of letting a young QB develop behind a veteran like Joe Flacco.
13:15 Mike reflects on the Deshaun Watson trade and emphasizes that the Browns must return to a ball-control offense built around Nick Chubb and strong character players.

Pre Draft Talk

Brook and Mike break down what they liked—and didn’t like—about the Cleveland Browns’ draft picks, including standout players, surprise decisions, and how the team’s future is shaping up
5:30 Brook recaps the Browns trading down from pick #2 to #5 and still landing impact player Mason Graham.
7:15 Mike and Brook discuss the Browns’ new running back duo as “thunder and lightning”—Judkins and the speedy back from Tennessee.
8:45 Brook explains the surprise around drafting two quarterbacks—Shedeur Sanders and Dillon Gabriel—and why it still made sense.
13:45 Brook compares Gabriel to Baker Mayfield, calling him a strong, accurate QB with real starting potential.
20:15 Mike and Brook agree Flacco should start, but the young QBs must get playing time this season to prove their value.

The Cleveland Browns Draft Recap

Brook and Mike discuss the power of scripting and planning for quick Airbnb turnarounds and for selling properties.
2:00 Mike introduces the idea of scripting your day and how vital it is for managing real estate and small business operations effectively.
3:00 Brook breaks down how she handles violation lists—deciding what can be done in-house, what needs to be outsourced, and the importance of being proactive before a house closes.
6:15 Mike reflects on the harsh realities of running a small business—juggling subs, maintenance issues, and why passion alone isn’t enough for success.
10:30 Brook explains how organizing work around the weather and staying in close communication with subs can save time, money, and stress.
21:15 Mike shares the three business fundamentals every small business owner should master: sales, creative marketing, and financial literacy.

This is the Cleveland Real Estate Investor with Mike Reilly, owner of Reilly Properties and Reilly Painting and Contracting. 

Mike has been in the home renovation business for 50+ years in the Cleveland area and the rental/real estate investing business for 20+ years.

In this podcast, we seek to take our experience and provide insight and inspiration for outside investors looking to buy property in Cleveland.

If you are a new investor, you will also find a lot of gems for how to get started in the investor/rental business.

Learn how to invest in real estate in Cleveland right here at the Cleveland Real Estate Investor Podcast.

Magic Matching Day

The Cleveland Real Estate Investor Podcast