Mike, Brook and A'marri discuss goal setting and strategic planning for your 
business. Your data should tell a story. Within that story are learning lessons that 
need to be applied to your new strategies. This goes for your business as well as your personal life. Some things are black and white and others are gray and nuanced. Be disciplined in your routine, but allow new ideas and creativity to process in the background of your mind after a power nap, run, workout or Mike's favorite, a "shower moment". We reflect in January as we prepare for the stress testing moments that show up later in the year in the middle of the action.

2:50 Mike and Brook discuss the importance of reviewing last year's performance, analyzing revenue, expenses, and whether certain investments were truly profitable.
4:35 Mike uses the analogy of weight loss to explain how business owners should track their progress, emphasizing the importance of writing everything down, measuring results, and making adjustments just like a fitness journey.
9:00 Mike, Brook and A'marri discusses the significance of tracking every expense, no matter how small, and how financial awareness can lead to better decision-making.
16:30 Mike emphasizes the importance of reflection and strategic thinking, encouraging business owners to take time to analyze what is working and what needs to change.
32:00 Amarri highlights the idea that data should tell a story, and decisions should be driven by the patterns and insights found in the numbers.

Past Events Dictate Future Behaviors

Mike and Brook get into the details of why young people, or people who are fixated with their passion, they've got a vision, they're going to be an artist, but they don't have anything back office. They don't have any concept of money or paying their bills, or just overly focused on that vision in front of them.
01:10 Mike introduces the topic of why artists struggle financially, questioning the "starving artist" cliché and why passion alone isn’t enough to succeed.
03:15 Mike references an article about how many New York residents rely on financial support from their parents or trust funds, highlighting the hidden advantages that allow some people to pursue artistic careers without financial worries.
07:45 Mike emphasizes that being an artist requires the same dedication as running any business, comparing it to the relentless work ethic of professional athletes.
11:05 Mike emphasizes the importance of teaching kids the value of hard work over passion, arguing that discipline and responsibility should come before chasing interests or hobbies
22:30 Brook and Mike conclude that artists starve because they aren't taught how to manage money or sustain themselves financially, emphasizing the need for business knowledge.


Why Do Artists Starve

In this episode of Small Business Confidential, A'marri and Brook have a laid-back chat about their week at work, covering time management, goal setting, and getting things done. Brook talks about balancing work with having a newborn and how routines help him stay productive. They also discuss the ups and downs of work life and share insights from Scott Galloway about focusing on mastering your skills instead of just following your passion.
2:10 Brook shares his experience balancing work and family life with a newborn at home, emphasizing the importance of maximizing time and being strict with schedules, even amidst daily chaos and unexpected events.
4:55 A'marri and Brook discuss goal-setting, highlighting how daunting tasks feel more achievable once you start taking actionable steps, similar to breaking down complex projects into manageable pieces.
6:55 Brook talks about his cold plunge routine, explaining how small morning habits like cold plunges or making the bed can set a productive tone for the day, helping overcome sluggish starts and boosting motivation.
18:00 Brook references insights from Scott Galloway, challenging the "follow your passion" advice, and instead promoting the idea of mastering a skill you're good at to build a successful and sustainable career.


Water cooler talk; management, goal setting, hills and valleys of work, and Scott Galloway.

Join us as Mike and Brook Reilly dive into why so many artists struggle financially. We'll explore how passion alone isn’t enough, the advantage of financial support and why understanding money is key to making a creative career sustainable. Plus, we'll break down why treating art like a business is the key to long-term success. All this and more on the Cleveland Real Estate Investor Podcast!
01:10 Mike introduces the topic of why artists struggle financially, questioning the "starving artist" cliché and why passion alone isn’t enough to succeed.
03:15 Mike references an article about how many New York residents rely on financial support from their parents or trust funds, highlighting the hidden advantages that allow some people to pursue artistic careers without financial worries.
07:45 Mike emphasizes that being an artist requires the same dedication as running any business, comparing it to the relentless work ethic of professional athletes
11:05 Mike emphasizes the importance of teaching kids the value of hard work over passion, arguing that discipline and responsibility should come before chasing interests or hobbies.
22:30 Brook and Mike conclude that artists starve because they aren't taught how to manage money or sustain themselves financially, emphasizing the need for business knowledge.


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

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

40+ year business owner, Mike Reilly, shares the dirty secrets of owning your own small business.

Past Events Dictate Future Behaviors

Small Business Confidential

Related tracks