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. 4D AGO

    How 10 Deals Can Make You a Millionaire

    Send us Fan Mail What if becoming a millionaire in real estate was simpler than you think? In this solo episode of The Wisconsin Investor, Corey Reyment breaks down a step-by-step plan to building over $1 million in equity, without needing hundreds of deals or massive amounts of capital. The strategy? Consistency. By walking through a real-world example, Corey shows how completing just a couple of deals per year can compound into serious wealth over time. From equity creation to appreciation and debt paydown, this episode lays out exactly how small, repeatable actions turn into big results.  Inside this episode:  • How 2 deals per year can lead to $1M+ in equity  • The power of compounding appreciation and debt paydown  • Why deal flow is the foundation of building wealth  • How refinancing can unlock large amounts of capital  • A realistic 5-year roadmap to scaling your portfolio Corey also breaks down how investors can recycle the same capital again and again, turning one opportunity into many and accelerating their path to financial freedom.  If you’ve been overcomplicating real estate or waiting for the “perfect” time to start, this episode shows what’s actually possible with a simple, focused plan. 🎧 Tune in now and start building toward your first $1 million in real estate.

    41 min

  2. MAR 31

    How to Scale Your Real Estate Business Without Doing Everything Yourself

    Send us Fan Mail Are you busy in real estate… but still feel stuck? In this solo episode of The Wisconsin Investor, Corey Reyment breaks down one of the biggest mistakes holding investors back, trying to do everything themselves. Drawing insights from the book Essentialism, Corey shares how focusing on fewer, higher-impact activities can help you scale faster, reduce stress, and actually build a business that works for you, not the other way around. If you’ve ever felt overwhelmed juggling deals, managing properties, handling bookkeeping, or constantly putting out fires, this episode will challenge the way you think about growth. Inside this episode:  • Why “more deals” doesn’t always mean more success  • The hidden cost of doing everything yourself  • How top investors actually scale their businesses  • The concept of “profit per hour” and why it matters  • When to outsource, and what to let go of first  • How to build systems that create real freedom Corey also shares real-world examples from his own business, including lessons learned from deals that pulled him away from his core focus, and how that impacted long-term growth.  Whether you're just getting started or already doing deals, this episode will help you rethink how you spend your time and where your real value is created. If your goal is more income, more freedom, and less chaos, this is a must-listen. 📘 Book mentioned in this episode:  Essentialism by Greg McKeown  https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382

    34 min

  3. MAR 24

    How to Navigate Tax-Efficient Real Estate Exits: Insights from Brandon Bruckman

    Send us Fan Mail In this episode of The Wisconsin Investor Podcast, Corey Reyment sits down with Brandon Bruckman to break down how real estate investors can think more strategically about exiting properties without losing momentum. For many investors, selling a rental property can feel like a setback, especially when taxes take a significant portion of the profit. Brandon shares how the right planning and structure can turn an exit into an opportunity to keep your capital working while reducing unnecessary tax burdens. Together, they walk through: • How to think about exits before you ever sell  • Why tax strategy plays a major role in long-term wealth building  • How investors transition from active management to more passive income  • Common mistakes that can cost investors time and money  • The importance of having a clear plan before making a move If you’re holding rental properties, considering selling, or just want to build a more durable long-term strategy, this episode offers a different way to think about keeping your money working for you. For off-market investment opportunities across Wisconsin, visit:  👉 WisconsinDiscountProperties.com

    55 min

  4. MAR 17

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

    Send us Fan Mail 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

  5. MAR 10

    Flipping vs Rentals: What Most Investors Get Wrong

    Send us Fan Mail 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

  6. MAR 3

    Creative Financing Strategies That Actually Work in Wisconsin Real Estate

    Send us Fan Mail 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

  7. FEB 24

    Dead Equity: The Silent Portfolio Killer Most Wisconsin Investors Ignore

    Send us Fan Mail 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

  8. FEB 17

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

    Send us Fan Mail 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
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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
    84
  • Rating
    Clean
  • Copyright
    © 2026 The Wisconsin Investor
  • Show Website
    The Wisconsin Investor

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