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In this episode of The Wisconsin Investor, Corey Reyment sits down with Collin Gudgeon, a senior in the University of Wisconsin–Madison real estate program, to break down what it really takes to succeed in Wisconsin real estate investing.

Collin grew up around flips and rental properties in Milwaukee and now studies commercial real estate finance, underwriting, and development in one of the country's top real estate programs. Together, Corey and Collin dive into:

• Why networking is the real “hack” in real estate
 • How to win deals without offering the highest price
 • The difference between flipping houses and building rental wealth
 • Why cash flow can be misleading in today’s market
 • House hacking strategies for young investors
 • How long-term equity growth and refinancing create real wealth

If you’re investing in Madison, Milwaukee, Green Bay, Appleton, or anywhere in Wisconsin, this episode is packed with practical insight on seller negotiations, financing strategy, and building a durable portfolio.

Connect with Collin Gudgeon:
Email: [email protected]

Phone: 414-429-9130

Looking for off-market deals across Wisconsin?
Visit WisconsinDiscountProperties.com to join the exclusive buyer list.

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In this episode of The Wisconsin Investor Podcast, Corey Reyment sits down with Madison real estate investor Joe Miller, founder of Rezen, to break down how he scaled from wholesaling to running a vertically integrated fix and flip business in Wisconsin.

We cover:

• Seller financing and mortgage wraps
 • Private money and bank funding strategies
 • Large rehab projects and six-figure renovations
 • Creative deal structuring when cash offers don’t work
 • The shift from wholesaling to flipping
 • Protecting investor capital the right way

If you’re investing in Wisconsin real estate, especially in Madison, and want to learn about creative financing, private lenders, and scaling a sustainable investment business, this episode delivers real-world insight.

Whether you’re a new investor looking to land your first deal or an experienced operator trying to build a more durable business model, this conversation delivers real-world strategy from someone actively doing deals.

Connect with Joe:
 rezenhub.com
 rentrezen.com

For off-market deals across Wisconsin, visit WisconsinDiscountProperties.com.

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In this episode of The Wisconsin Investor Podcast, Corey Reyment breaks down a real conversation with a Wisconsin landlord whose duplex doubled in value from $165,000 to $340,000. On paper, it looked like a win.

But when they calculated the actual return on equity, the property was only producing 2.8%.

That is what we call dead equity.

This episode explores how appreciation can quietly turn into underperforming capital, and why many small investors focus on value growth, door count, or cash flow while ignoring how hard their equity is actually working.

Corey walks through:

• How to calculate return on equity step by step
 • Why a rental property can become an anchor instead of an asset
 • The opportunity cost of leaving large amounts of equity untouched
 • 1031 exchanges and portfolio repositioning strategies
 • Cash out refinancing and HELOC options in Wisconsin
 • When it makes sense to recycle capital and when it does not
 • How tax strategy and bonus depreciation factor into real returns

If you own rental property in Wisconsin, especially single-family homes, duplexes, or small multifamily, this episode will challenge how you think about portfolio growth.

Serious investors do not just accumulate properties. They reposition equity strategically.

If you want to build long-term wealth in Wisconsin real estate, you cannot afford to ignore dead equity.

For off-market opportunities and investor resources, visit WisconsinDiscountProperties.com.

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Corey Reyment sits down with Mason Clark, Chief Investment Officer of Park Place Holdings, to break down what commercial real estate investing actually looks like in Wisconsin.

From negotiating a $17 million listing down to a $2.5 million purchase… to turning a vacant 150,000 square foot office building into a multi-tenant value-add opportunity… this episode is a real-world look at how commercial deals get done in markets like Green Bay, Appleton, and Northeast Wisconsin.

You’ll learn:
• How to structure commercial real estate deals creatively• Why you don’t always need 20–25% down to get started• How value-add commercial investing works in Midwest markets• The difference between residential and commercial underwriting• How cap rates, lease structures, and long-term holds actually play out• Why relationships with local banks matter more than national lenders• What it takes to scale from small deals to nine-figure portfolios

This is not theory. This is how real Wisconsin investors are building wealth through office, retail, redevelopment, and strategic acquisitions.

If you’ve ever wondered whether commercial real estate is “too big” or “too risky,” this episode will give you practical insight into how experienced investors evaluate risk, negotiate deals, and create long-term cash flow in steady Midwest markets.

Whether you’re investing in single-family homes, duplexes, multifamily, or looking to move into commercial real estate, this conversation will expand the way you think about opportunity.

Connect with Mason:[email protected]

Looking to invest in Wisconsin real estate?Visit wisconsindiscountproperties.com for off-market opportunities and investor-friendly deals.

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Bitcoin is down. Gold and silver are slipping. Investors everywhere are asking the same question. Where should I put my money now?

In this solo episode of The Wisconsin Investor, Corey Reyment breaks down what today’s market volatility really means and why periods like this often quietly benefit real estate investors, especially in Midwest markets like Wisconsin.

This is not a crypto debate or a gold-bashing episode. It is a grounded conversation about risk, liquidity, control, and long-term fundamentals. When speculative assets fall fast, fear gets loud, but opportunity tends to show up in places that do not make headlines.

In this episode, Corey explains:

• Why Bitcoin, stocks, and gold are often the first assets sold during market fear
• How liquidity cuts both ways in investing
• Why real estate does not react to headlines the same way
• Why Wisconsin’s demand-driven housing markets continue to perform over time
• Why waiting for the perfect market crash often backfires
• Why boring, cash-flowing properties consistently win long-term

If you are a real estate investor wondering whether now is the right time to buy or if you have been sitting on the sidelines waiting for clarity, this episode is a reminder that fundamentals beat speculation and consistency beats timing.

This episode is especially relevant for investors focused on single-family homes, duplexes, and small multifamily properties who want to build long-term wealth through steady cash flow and disciplined investing in the Midwest.

Visit wisconsindiscountproperties.com to get access to the exclusive deal list with off-market and investor-friendly opportunities across Wisconsin.

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This episode isn’t about a massive win. It’s about surviving a deal that went sideways and not quitting.

Matt Richardson and Ashley joined Corey to share the reality of their first flip, a deal that looked solid on paper but quickly turned into a crash course in rehab overruns, contractor missteps, shifting lender rules, and refinance delays that pushed them months past their hard money maturity.

Their $47,000 rehab turned into $100,000+, driven by:

• Poorly defined scopes of work
• Surprise subfloor, plumbing, and electrical issues
• A contractor who quoted labor loosely and billed tightly

Once the rehab was done, the market didn’t cooperate. Offers came in $40–60K below asking, and selling would have locked in a loss. Instead of panicking, they pivoted.

Through networking and honest lender communication, they landed on a creative rent-to-own exit:

• $400,000 sale price
• No realtor commissions
• 5-year term at roughly 2 percent interest
• Buyers refinance them out later

What could have been a deal-ending loss turned into a long-term win and a masterclass in resilience.

The biggest takeaway?
 👉 One bad deal doesn’t define you. Quitting does.

If you want to connect with Matt or Ashley directly, you can reach them here:
Ashley: [email protected]
Matt: [email protected]

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In this episode of The Wisconsin Investor Podcast, Reese Brown and Connor Derenne tackle the real conversations they have every single week with Wisconsin investors. Not theory. Not guru advice. The objections and roadblocks that actually stop people from doing deals.

The episode focuses on why so many investors feel stuck, what “analysis paralysis” really looks like in practice, and how clarity around goals, buy boxes, and networking is what actually moves deals forward.

Rather than talking about market timing or perfect deals, Reese and Connor break down:

🔍 Why most investors don’t know what they’re actually looking for
 ⏳ How waiting for the “perfect” deal often costs more than a bad first deal
 🎓 Why your first deal can be tuition, not failure
 🤝 How networking quietly solves confidence, funding, and execution issues
 🏦 Why Wisconsin’s local lending and investor ecosystem is a massive advantage

The core theme is simple. Progress comes from clarity and action, not more consumption.

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In this solo episode of The Wisconsin Investor Podcast, Reese Brown steps in behind the mic and brings the conversation back to the basics, & why real estate still works in 2026.

Rather than chasing trends or debating headlines, this episode focuses on fundamentals: leverage, equity growth, long-term appreciation, and tax advantages. Reese challenges the idea that cash flow is the only thing that matters and reframes real estate as a system, not a single bet.

Using simple analogies (including gold, leverage, and tenants as “partners”), the episode walks listeners through:

• Why real estate has remained resilient for decades
• How leverage multiplies returns responsibly
• Why equity beats short-term cash flow
• How BRRRR still works, even in today’s market
• Why investors waiting on the sidelines may miss an opportunity

This episode is especially relevant for:

• New investors feeling overwhelmed
• Experienced investors stuck over-analyzing deals
• Anyone questioning whether “now” is still a good time

The core message is clear: real estate hasn’t changed... expectations have.

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Corey sits down with Mike Morawski, a longtime real estate investor who’s seen every side of the business — massive growth, catastrophic failure, federal prison, and redemption back into multifamily investing and coaching.

Mike shares how he went from:

• Building a $100M+ real estate company in 30 months
• Owning 4,000+ units across five markets
• Managing 7,500 units and 100 employees

…to losing everything after the 2008 crash due to:

• Growing too fast
• Overleveraging
• Being undercapitalized
• Ignoring red flags
• Failing to communicate transparently with investors

The conversation goes way deeper than real estate. Mike opens up about prison, humility, faith, mental health, leadership mistakes, marriage, listening to your spouse, and why real success is built through lessons learned the hard way.

This isn’t a guru episode.
 It’s a “learn from my scars” episode.

📘 Want to go deeper? Mike is the author of Multifamily Investment Secrets, where he breaks down creative multifamily strategies and hard-earned lessons from decades in the business — you can check out the book here: Multifamily Investment Secrets

🔗 Connect with Mike Morawski

Website:
http://mikemorawski.com/

Free eBook – Multifamily Investment Secrets:
https://multifamilyinvestmentsecrets.com/

Social Media:
Facebook: https://www.facebook.com/mike.morawski.54

Instagram: https://www.instagram.com/mike.morawski.54/

LinkedIn: https://www.linkedin.com/in/michael-morawski/

TikTok: https://www.tiktok.com/@mikemorawski

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In this episode of The Wisconsin Investor Podcast, Corey sits down with Chris Hake, a 30+ year Wisconsin real estate investor and founder of Wisco REIA, to break down what actually leads to long-term success in real estate.

They dive into real-world lessons from multiple market cycles and unpack why most investors get stuck — even when they’re working hard.

In this episode, you’ll learn:
• What 30+ years of investing in Wisconsin teaches you about risk and growth
• Key lessons from the 2008 crash that still apply today
• Why focus beats chasing multiple strategies
• How mentorship and paid coaching shortcut years of mistakes
• The danger of shiny object syndrome in real estate
• Why networking and local investor groups accelerate success
• How to decide which real estate strategy fits you
• The mindset shift required to go from learning to actually doing deals

If you’re trying to get started, get unstuck, or build a sustainable real estate business in Wisconsin, this episode delivers practical insight without the hype.

Connect with Chris Hake:
📧 [email protected]
🌐 www.wiscoria.com