The Wisconsin Investor

The Wisconsin Investor

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.

Episodes

October 14, 2025 39 mins

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This week, we sit down with our teammate and acquisition specialist Page Nelson, who went from overthinking to owning it—literally. He breaks down how he pushed past fear, landed his first profitable flip, stumbled on the second, and came out sharper, faster, and more confident as an investor.

If you’ve ever hesitated to pull the trigger on a deal, this episode will help you see how clear math and smart systems beat fe...

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Tired of messy flips, blown timelines, and deals that drain more than they deliver? Kent shows us how he flipped the script—moving from contractor to investor—by building calm, repeatable systems, using BRRRR strategies, and turning stale MLS listings into instant equity. If you want smoother projects and smarter profits, this one’s for you.

🔥 Inside This Episode:
📊 Case studies + ARVs: how to price right and av...

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From a quick “clean and list” starter flip to full financial freedom by mastering systems, roles, and mindset.

🔥 Inside This Episode:
🏡 How one investor turned a light rehab + relist into momentum for multi-unit deals
💰 The seller-financed 55-unit acquisition—structured at 0% down and 2.38% interest
⚙️ Using AppFolio + a VA to automate portfolio management and save hours per week
🔁 Why focusing ...

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Sean Gibbons shares the rollercoaster of his real estate career—from acquisitions to complex, sideways deals—highlighting how creativity, resilience, and relationships carry you when plans implode.

• House-hacked a duplex after reading Rich Dad, Poor Dad
• Cut his teeth in acquisitions at Wisconsin Discount Properties before going solo
• Survived a $3.5M greenhouse foreclosure that ultimately settled for $20,...

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September 16, 2025 50 mins

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What if you could buy your very first duplex with zero dollars out of pocket—while making just $10 an hour as an apprentice? That’s exactly how Corey Paszkiewicz launched his real estate journey over 20 years ago. Today, he owns 64 rental units with roughly 50% equity across the board—and in this episode, he breaks down how you can follow a similar path.

🔥 Inside This Episode:

  • 🏡 How Corey bought his first duplex u...
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What if you could create $48,000 in equity with just a few hours of effort? The BRRRR strategy (Buy, Rehab, Rent, Refinance, Repeat) offers exactly this opportunity when executed properly, as demonstrated in this detailed deal breakdown of a Wisconsin duplex purchase.

Corey walks us through the entire process of a recent BRRRR project from start to finish – from finding the deal through texting campaigns to f...

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What if everything you’ve been told about “financial freedom” through rental properties is wrong?

In this episode of The Wisconsin Investor, we sit down with Jimmy Vreeland, a former Army Ranger turned successful real estate investor, to challenge the traditional cash-flow-only mindset.

💡 Jimmy introduces his concept of the “cash machine”
🏡 We share how chasing 100 rental doors taught us hard lessons about the $2...

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From college dropout to running 50 flips a year—Carter Crowley’s real estate journey proves what’s possible when you master your numbers, build strong relationships, and take consistent action.

In this episode of The Wisconsin Investor Podcast, Carter reveals how he went from traditional agent to full-time investor and the exact strategies that fueled his rapid growth.

What you’ll learn in this episode:

  • How Carter fu...
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📉 Tired of the 9-to-5 grind? This episode of The Wisconsin Investor Podcast features Eric Nelson, a former 20-year corporate employee who walked away from his job at US Cellular — and flipped his first house for a $35,000 profit in just 70 days.

🎙️ In this inspiring interview, Eric breaks down:

  • How he turned a severance package into a real estate business
  • The foundation problem flip that scared away other investors...
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What if you could buy real estate, pull all your money back out, and still build long-term wealth? That’s the power of the BRRRR method — and in this episode, Corey breaks it all down.

From one college rental to 700+ units, Corey shows how Buy, Rehab, Rent, Refinance, Repeat can be your path to financial freedom, even with today’s interest rates.

Inside this solo episode:

  • How a $300K property can build $200K–$450K in...
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🎙️ How Scott Carson Bought $1 Billion in Distressed Debt — And Helped Homeowners Along the Way

Ever wondered how to become the bank and earn double-digit returns—without swinging a hammer or flipping houses?

In this episode of The Wisconsin Investor, we sit down with Scott Carson, founder of WeCloseNotes.com, who shares how he's purchased over $1 billion in distressed debt and created win-win outcomes for struggli...

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From College Rental to 700+ Units: How Ryan Gray Built a Real Estate Empire in Just 7 Years

What happens when you take massive action, skip the fluff, and build powerful local relationships? You get Ryan Gray — a Wisconsin-based investor who scaled from a single college house to over 700 multifamily units and 15 group homes in just seven years.

In this episode, Ryan shares how he launched Stable Living, an assisted livi...

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What does it look like when a full-time cop and a transaction coordinator on the iBuyWI team decide they’re done waiting for retirement?

Andy Lade and Vanessa Ring are a Wisconsin couple flipping their way to financial freedom, while working full-time, and figuring it out as they go.

In this episode, you’ll hear how they went from zero experience to confidently managing multiple flips and rental prop...

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New Tax Law Just Changed Everything for Real Estate Investors
The “Big Beautiful Bill” just rewrote the tax code—and if you're a real estate investor, you need to know what changed. In this episode, tax strategist Kaden Hackney breaks down the biggest updates, including 100% permanent bonus depreciation, massive cost segregation advantages, and Opportunity Zone extensions that can help you build wealth tax-f...

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How Wyatt Powell Bought 4 Properties in 2 Months—From 2,000 Miles Away | The Wisconsin Investor Podcast

Can you build a real estate portfolio without even living in the same state? Wyatt Powell did exactly that—locking in four properties in just two months while living in Scottsdale, Arizona and investing in Wisconsin.

In this episode, Corey and Wyatt break down:

  • 🔁 How the BRRRR strategy creates infinite returns (wi...
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What if you could scale your real estate business using AI — without writing a single line of code?

This week, we sit down with John “Big Money” Maxi, a full-time data scientist managing 21 rental doors, who’s using custom GPTs and AI tools to streamline his real estate systems, boost decision-making, and replace the need for a team.

From building a virtual board of advisors powered by legends like Kiyosaki and Cardone,...

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What if you could invest in real estate without dealing with tenants, toilets, or day-to-day headaches?
In this episode, Dr. Kate Gress shares how she’s transitioning out of her 26-year chiropractic career by building a scalable real estate syndication business.

Kate breaks down how syndications work, the role of general and limited partners, and how you can generate cash flow and tax advantages without being a la...

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From House Hacks to Land Flips: Dylan Rusch’s Strategy for Scalable Real Estate Wealth

Dylan Rusch went from rookie house hacker to full-time land investor in just a few years — and in this episode, he breaks down the exact blueprint he followed to do it.

He started by buying duplexes with just 5% down and converting them into short-term rentals. One unit that used to bring in $500/month? After Dylan’s strategy, it earn...

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The First Deal: How Connor Derenne Got $30K in Equity Right After College

 🎙 The Wisconsin Investor Podcast — What It’s Really Like Doing Your First Real Estate Deal w/ Connor Derenne

In this episode of The Wisconsin Investor, we sit down with Connor Derenne, a young investor who landed his first real estate deal less than a year after graduating college—and walked away with $30,000 in instant equity.

Connor proves that...

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Is fear keeping you from building wealth through real estate?

In this episode of The Wisconsin Investor Podcast, we sit down with Chris Charles—a real estate investor and title company professional with over 40 years of experience—for a raw, honest conversation about what it really takes to build a portfolio and create lasting financial freedom.

Chris shares his full journey:
 ➡️ From renovating "handyman speci...

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