The Wisconsin Investor

Corey Reyment
  • 5.0 (16)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Each week, we bring you interviews with some of Wisconsin's top real estate investors who share their tips, tricks, and strategies that you can implement right away. This show is dedicated to helping Wisconsin real estate investors elevate their game. Along with interviews, I'll also dive into hot topics in solo episodes and feature experts from various real estate sectors across Wisconsin. 

  1. 5D AGO

    Stop Waiting for Money in Real Estate (Do This Instead)

    Send a text In this episode of The Wisconsin Investor Podcast, Corey Reyment sits down with South Central Wisconsin investor Tim Dougherty, a full-time real estate entrepreneur who has been in the game since 2008. From surviving the 2008 crash to completing 50+ deals in the last five years alone, Tim breaks down what it really takes to build a sustainable real estate investing business in Wisconsin. Tim currently owns 17 rental units and operates Doc The House Buyer, helping distressed homeowners in Rock, Jefferson, and Dane Counties. He shares how he left his W-2 job, raised millions in private money, structured deals creatively, and built long-term wealth through flips, rentals, and wholesales. In this episode, you’ll learn: How to raise private money even if you have zero capitalWhy “the deal attracts the money” is more than just a sayingThe mindset shift that helped Tim leave his W-2 jobHow mentorship accelerated his investing careerWhy networking is the real shortcut in real estateHow to structure your schedule while building your investing businessLessons from investing through multiple market cyclesIf you’re investing in Madison, Janesville, Rock County, Dane County, or anywhere in Wisconsin, this episode is packed with practical strategies for scaling your portfolio and building financial freedom through real estate. Connect with Tim Dougherty:  📧 yresllc@gmail.com For off-market investment opportunities across Wisconsin, visit:  👉 WisconsinDiscountProperties.com

    44 min

  2. MAR 10

    Flipping vs Rentals: What Most Investors Get Wrong

    Send a text 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: collin@blackridge-co.com Phone: 414-429-9130 Looking for off-market deals across Wisconsin? Visit WisconsinDiscountProperties.com to join the exclusive buyer list. Need help leasing your units? Check the link below! https://nl5a6.share.hsforms.com/2fKXr-r9eSCuMkCRT8KFEnQ

    55 min

  3. MAR 3

    Creative Financing Strategies That Actually Work in Wisconsin Real Estate

    Send a text 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.

    47 min

  4. FEB 24

    Dead Equity: The Silent Portfolio Killer Most Wisconsin Investors Ignore

    Send a text 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.

    33 min

  5. FEB 17

    Breaking Into Commercial Real Estate in WI (Without 25% Down)

    Send a text 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:mason@parkplace-holdings.com Looking to invest in Wisconsin real estate?Visit wisconsindiscountproperties.com for off-market opportunities and investor-friendly deals. Subscribe for weekly conversations with real investors doing real deals in Wisconsin.

    48 min

  6. FEB 10

    Bitcoin & Gold Are Crashing: What Smart Real Estate Investors Do Next

    Send a text 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 fearHow liquidity cuts both ways in investingWhy real estate does not react to headlines the same wayWhy Wisconsin’s demand-driven housing markets continue to perform over timeWhy waiting for the perfect market crash often backfiresWhy boring, cash-flowing properties consistently win long-termIf 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.

    25 min

  7. FEB 3

    First Real Estate Flip Gone Wrong: Lessons From a $100,000 Rehab Overrun

    Send a text 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 workSurprise subfloor, plumbing, and electrical issuesA contractor who quoted labor loosely and billed tightlyOnce 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 priceNo realtor commissions5-year term at roughly 2 percent interestBuyers refinance them out laterWhat 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: ashley@ibuywi.com Matt: mtrichardson45@gmail.com

    50 min

  8. JAN 27

    What Actually Moves Real Estate Deals Forward

    Send a text 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.

    35 min
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5
out of 5
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About

Each week, we bring you interviews with some of Wisconsin's top real estate investors who share their tips, tricks, and strategies that you can implement right away. This show is dedicated to helping Wisconsin real estate investors elevate their game. Along with interviews, I'll also dive into hot topics in solo episodes and feature experts from various real estate sectors across Wisconsin. 

Information

  • Creator
    Corey Reyment
  • Years Active
    2024 - 2026
  • Episodes
    81
  • Rating
    Clean
  • Copyright
    © 2026 The Wisconsin Investor
  • Show Website
    The Wisconsin Investor

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