When Good Deals Go Bad: Real Stories From Experienced Investors
Rental Property Owner & Real Estate Investor Podcast
Release Date: 03/02/2026
From $200 a Month to $5,000: How the Co-Living Model Transforms Rental Cash Flow with Katrina Robinson
Rental Property Owner & Real Estate Investor Podcast
Co-living is one of the most overlooked strategies in real estate investing. While most investors chase single-family rentals generating $200 a month per door, a small group of operators is filling houses with multiple residents, charging per bed, and clearing $5,000 or more on a single property. In this episode, co-living investor and coach breaks down exactly how this model works, who it serves, and how she runs three properties in San Antonio, Texas from Los Angeles. About Katrina Robinson Katrina Robinson is the founder of the Group Home on Autopilot coaching program and operator of...
info_outline
The $100M Mistake: Why Investors Confuse Market Price with Investment Value with Ryan Cadwell
Rental Property Owner & Real Estate Investor Podcast
Most investors think price equals value. They look at comps. They trust broker packages. They assume appreciation will fix everything. That’s where they get into trouble. In this episode, I sit down with , Principal of Resolute RDM, an Indianapolis-based firm involved in over $100M in transactions, development, and asset management. Ryan has flipped nearly 150 homes and is currently developing more than 240 duplex units. He breaks down what he calls the “$100M mistake” — confusing market price with investment value — and why overly optimistic underwriting is putting investors in...
info_outline
AI, Maintenance, and Metrics: Modern Property Management with Donny Nguyen
Rental Property Owner & Real Estate Investor Podcast
Most investors blame the market. Very few examine their management. Vacancy, delinquency, and maintenance creep rarely start with the economy. They start with weak systems, poor tracking, and inconsistent execution. In this episode, Brian talks with Donny Nguyen, real estate investor, business strategist, and founder of VanderWinn Property Management. Donny brings a background in corporate strategy, supply chain, finance, and systems design into the world of rental property management. If you want your rentals to function like real assets instead of side hustles, this episode is for you. In...
info_outline
Creative Financing Explained: DSCR, Hard Money, and Why Rate Isn’t Everything with Fred SaintAmour
Rental Property Owner & Real Estate Investor Podcast
Too many investors chase interest rates and ignore structure. They worry about an eighth of a point while overpaying on taxes, misunderstanding underwriting, or choosing the wrong loan product entirely. In this episode, Fred SaintAmour of Boathouse Commercial Funding Group breaks down how lenders actually assess risk and why most investors misunderstand leverage. We cover: How debt service coverage ratio (DSCR) loans really work When hard money makes sense — and when it doesn’t Why collateral and marketing time matter more than you think What immediately disqualifies a deal How...
info_outline
Economic Trends Real Estate Investors Need to Watch | MREIC 2026 Spotlight: Dr. Paul Isely
Rental Property Owner & Real Estate Investor Podcast
In this episode, Dr. Paul Isely joins the podcast for another MREIC 2026 Speaker Spotlight where he unpacks the market signals, economic trends, and bigger-picture forces that could shape investment decisions in the months ahead. Dr. Isely is Associate Dean and Professor of Economics at Grand Valley State University’s Seidman College of Business and is widely respected for making economic insight practical, relevant, and actionable. His closing keynote session at MREIC 2026 will help attendees better understand where the market may be headed and what that could mean for real estate...
info_outline
Manufactured Housing as a Recession-Resistant Strategy | $45M Across 25 Communities with Matthias Gruenwald
Rental Property Owner & Real Estate Investor Podcast
Manufactured housing rarely gets attention until markets tighten. That’s exactly why Matthias Gruenwald built a business around it. In this episode, Matthias, co-founder of WCG Investments, shares how he grew from a duplex in 2022 to overseeing roughly $45 million across 25 manufactured housing communities in less than three years. Before real estate, Matthias was a global manufacturing COO. He brought that same operational discipline into an asset class that rewards execution over hype. We break down why manufactured housing can be one of the most stable and misunderstood sectors in real...
info_outline
How to Beat Airbnb Fees: Book-Direct Strategy, Distribution Costs, and Scaling Vacation Rentals with Eric Goldreyer
Rental Property Owner & Real Estate Investor Podcast
Short-term rentals have matured fast. But many operators are still stuck paying rising distribution costs while losing control of the guest relationship. In this episode, Eric Goldreyer, hospitality entrepreneur and founder of BedandBreakfast.com, former co-founder of TurnKey Vacation Rentals, and creator of Savvy, joins Brian to unpack what’s happening behind the scenes in vacation rental distribution. Eric has built, scaled, and sold companies in the space. He also owns and operates a 20-key boutique hotel outside Austin, giving him both strategic and ground-level insight into hospitality...
info_outline
Nathan Biller on How to Evaluate ADU Opportunities: MREIC 2026 Speaker Spotlight
Rental Property Owner & Real Estate Investor Podcast
is joining us at the 2026 to break down what real estate investors need to know about ADU development in today’s market. Nathan is a real estate investor, infill developer, ADU specialist, and Co-Founder of My Backyard Build. Based in Grand Rapids, he helps homeowners and real estate investors add housing through small-scale, zoning-aligned development. His work combines practical operator experience, a finance background, and active involvement in local housing policy and planning. In this conversation, Nathan explains what an accessory dwelling unit actually is, why ADUs are becoming...
info_outline
Boring but Profitable: How Midwest Workforce Housing Beats Hype Markets with Jeremy Yost
Rental Property Owner & Real Estate Investor Podcast
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, stabilizing rents, and delivering durable cash flow. In this episode, Jeremy Yost, Navy veteran and CEO with over $244M developed across 56 properties and 2,000+ units, shares why his disciplined Midwest strategy continues to perform through volatile market cycles Jeremy focuses on workforce housing, market-rate multifamily, Litech developments, assisted living, and hospitality — all...
info_outline
Creative Financing in 2026: Zachary Beach’s MREIC Speaker Spotlight
Rental Property Owner & Real Estate Investor Podcast
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 , Zach shares how real estate investors can structure deals without relying solely on traditional bank loans, large down payments, or personally guaranteeing debt, and why those strategies are gaining momentum as interest rates remain elevated and more sellers need flexible solutions. Zachary previews what attendees will learn in his MREIC session, including how to buy and sell creatively, how to create multiple...
info_outlineEvery real estate investor has at least one deal they would redo if given the chance. Some teach expensive lessons. Others leave scars.
In this episode, Brian Hamrick shares a live panel recording from the 2025 Midwest Real Estate Investor Conference, where three experienced investors pull back the curtain on their toughest deals and what they learned the hard way.
This is not theory. These are real properties, real numbers, real mistakes, and real consequences.
Panelists Featured
-
Ramond Harris – Detroit investor and founder of Harris Family Contracting, sharing the realities of rehabbing in high-risk neighborhoods and managing theft, vandalism, and city challenges.
-
Brooke Veltkamp – Newaygo County investor walking through extreme fixer projects, budget blowouts, and why buying right still matters more than anything else.
-
David Hall – Lansing-based investor, broker, and coach breaking down due diligence failures, permit issues, and why “new” does not always mean “good.”
Topics Covered
-
Buying properties with hidden deferred maintenance
-
When zero-down and creative financing deals go sideways
-
Fires, theft, vandalism, and city enforcement surprises
-
Roofs, plumbing, HVAC, and inspections that were missed
-
How long projects really take versus the original plan
-
When luck saves a deal and when it does not
-
Risk versus reward in changing market conditions
-
How experienced investors recover, pivot, and move forward
Why This Episode Matters
This panel is a clear example of what you get at the Midwest Real Estate Investor Conference.
Experienced operators sharing real decisions, real consequences, and what they would change if they had the chance.
No theory. No highlight reels.
Just lessons earned the hard way and explained so you do not have to repeat them.
If you want to make better decisions, manage risk more clearly, and avoid common traps, this episode delivers.
Join Us in 2026
The Midwest Real Estate Investor Conference is a two-day, content-dense event built for investors who want to think clearly, act decisively, and grow with intention.
You will hear from active investors, operators, lenders, and builders covering acquisitions, financing, market cycles, operations, and risk. Conversations are practical, candid, and grounded in real experience.
If this panel resonated, you will want to be in the room.
For more information and to get your ticket, go to midwestreiconference.com
Today’s episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area.
https://www.livegreenlocal.com
And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits.