Send us Fan Mail

In this episode of The Wisconsin Investor Podcast, Reese Brown steps in for a solo Part 2, building off Corey’s original “10 Deals to Become a Millionaire” concept, and takes things a step further with a real, live deal analysis.

Instead of theory, Reese walks through an actual property currently available through Wisconsin Discount Properties and breaks it down from start to finish. From purchase price and rehab costs to financing options and projected returns, this episode shows what a deal really looks like when you run the numbers.

The biggest takeaway? Cash flow might not be as important as you think.

Reese dives into:
 • A full breakdown of a real Green Bay investment property
 • How to analyze ARV, rehab costs, and financing options
 • The difference between flipping vs. holding (BRRRR strategy)
 • Why cash flow can be overrated in today’s market
 • How equity, appreciation, and principal paydown build real wealth
 • What happens when you scale this strategy to 10 deals

Using projections over a 5-year period, this episode highlights how the majority of wealth in real estate doesn’t come from monthly cash flow, but from long-term equity growth and leverage.

If you’ve been sitting on the sidelines waiting for the “perfect” deal, this breakdown might change how you think about investing in today’s market.

Whether you're investing in Green Bay, Milwaukee, Madison, or anywhere in Wisconsin, this is a practical, numbers-driven look at how deals actually work in real life.

Full episode available now on YouTube, Apple, and Spotify.

#WisconsinRealEstate #RealEstateInvesting #BRRRR

Send us Fan Mail

In this episode of The Wisconsin Investor Podcast, Reese Brown sits down with Will Traber, a former middle school principal who made the leap into full-time real estate investing, and scaled fast.

Will shares how he went from a stable W-2 career to building a growing portfolio of rental properties and flips in just over a year. But it wasn’t smooth sailing. His first rehab turned into a full gut job, partnerships fell apart mid-project, and he had to navigate multiple high-pressure deals at once.

Through it all, one thing set him apart: massive, imperfect action.

In this episode, you’ll hear:
 • How Will transitioned from education into real estate investing
 • Lessons from a first flip that went completely sideways
 • Why networking was the biggest “needle mover” in his success
 • How he funded deals without a large cash reserve
 • The reality of scaling, hiring, and managing multiple projects
 • Why simplifying your life can accelerate your investing journey

If you’ve been stuck in analysis paralysis or waiting for the “perfect time” to start investing, this episode is your wake-up call.

Will’s story is proof that you don’t need perfect conditions, you just need to start.

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.

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

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

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 capital
• Why “the deal attracts the money” is more than just a saying
• The mindset shift that helped Tim leave his W-2 job
• How mentorship accelerated his investing career
• Why networking is the real shortcut in real estate
• How to structure your schedule while building your investing business
• Lessons from investing through multiple market cycles

If 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:
 📧 [email protected]

For off-market investment opportunities across Wisconsin, visit:
 👉 WisconsinDiscountProperties.com

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: [email protected]

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

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.

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.

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:[email protected]

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.