Mike Cherwenka has been through the real estate cycle more than once.
In this episode, Art talks with Mike about what it actually takes to survive and succeed in real estate investing. Mike has spent decades in the business as a builder, fix-and-flip investor, mentor, and licensed agent. He has seen the big wins, the ugly deals, the contractor issues, the market shifts, and the kind of setbacks that can humble just about anybody.
The conversation starts with what Mike does today… helping investors find, renovate, and sell properties the right way. From there, he walks through how he got into real estate in the 90s, how his first wholesale deal came together, how he built serious volume, and what happened when the market changed.
This is not a sugarcoated conversation about flipping houses. It is a real one.
Topics Covered
- What Mike does today as a builder, investor, and mentor
- Why new investors need guidance before jumping into fix-and-flips
- The danger of overpaying for a property
- Why repair estimates matter so much
- How over-improving a house can hurt the deal
- Mike’s first real estate deal
- Building a buyer list before email marketing tools existed
- Wholesaling 77 properties in one year
- The transition into rentals and larger deals
- What happened when the market turned
- How pride and pressure can get expensive
- Why money management is everything in investing
- Why mentorship matters
- The importance of problem-solving and humility
- Why Mike enjoys helping other investors succeed
Favorite Takeaway
Real estate investing is not just about finding a deal. It is about knowing your numbers, managing your money, solving problems, staying humble, and surrounding yourself with people who have already been through the hard parts.
00:00 Welcome to Putting the Real in Real Estate
00:33 Meet Mike Cherwenka
01:01 What Mike does today
01:24 Working with fix-and-flip investors
01:48 Why new investors can get slaughtered
02:24 When sellers overestimate property value
02:57 How Mike makes money in the process
04:19 Avoiding over-improving a property
05:11 Renovation costs, walls, headers, and hidden expenses
07:53 How Mike got into real estate
08:32 Walking out in faith and finding real estate
08:46 Learning through seminars, books, and investor groups
09:30 Mike’s first deal
09:55 Everything that went wrong
10:02 Why money management matters
11:00 How early deals were structured
11:55 The first wholesale deal
12:29 Building a buyer list before modern tech
12:42 Doing 77 wholesale deals in one year
13:01 How Mike found properties
14:35 Growing into rentals and larger opportunities
15:12 Wholesaling, flipping, and rental portfolios
15:20 When the market turned
16:03 Debt, deficiencies, and dark seasons
17:41 What hard times teach you
18:10 Rebuilding after the setback
20:15 Advice for new fix-and-flip investors
21:00 Why problem-solving matters
21:24 Humility, mentorship, and learning the business
21:40 Why owning assets matters
22:28 Why this needs a part two
23:22 Mentoring the next group of investors
24:28 Leaving people better off
24:42 Closing thoughts