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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.
53 Episodes
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Send us a text 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 $200–$300 per door cash flow myth. 📈 We break down how real wealth...
Send us a text 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 funded his first flip in 2018 using a $65,000 family loan and $3...
Send us a text 📉 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 businessThe foundation problem flip that scared away other investors (but made him $35K)Leveraging Home Depot’s kitchen design servic...
Send us a text 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 wealth over 15 yearsWhy cash flow is nice, but equity and ref...
Send us a text 🎙️ 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 struggling homeowners. 🔑 What You’ll Learn: • What note investing is and...
Send us a text 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 living company, while still attending UW-Eau Claire, and how at...
Send us a text 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 properties. From using home equity to fund their first deal to learning how to in...
Send us a text 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-free over the next decade. Here’s what’s inside: • How to immedia...
Send us a text 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 (with zero dollars left in the deal)💰 Wyatt’s exact private money ...
Send us a text 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, to creating AI assistants that hold him accountable, John ...
Send us a text 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 landlord. She shares how coaching, networking, and a clearly defin...
Send us a text 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 earned over $5,100 in its first month as an Airbnb. Using HELOC...
Send us a text 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 you don’t need to be rich, experienced, or “ready” to...
Send us a text 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 specials" with his dad as a kid ➡️ To acquiring multiple renta...
Send us a text From first-time buyer at 18 to running a multi-million dollar real estate operation—Mike Boyea’s journey is packed with hard-earned lessons, practical insights, and real talk on what it takes to make it in this business. In this episode, Mike breaks down exactly how he went from buying a distressed duplex in 2003 to managing over 50 rental doors, flipping 60–70 properties a year, and building ground-up construction—all without a college degree. Mike opens up about the reality o...
Send us a text Real estate success takes more than great deals—it takes strategy, partnerships, and a mindset built for the long game. In this episode of The Wisconsin Investor, Corey Reyment sits down with Leon Barnes, longtime investor and Membership Director at Collective Genius, to talk about what it really takes to grow a rental portfolio that lasts. Leon shares how he’s used the BRRRR strategy (Buy, Rehab, Rent, Refinance, Repeat) to build a portfolio with “infinite returns,” pulling h...
Send us a text Can you legally pay zero taxes as a real estate investor? Should that even be your goal? CPA Marcus Crigler challenges conventional wisdom in this eye-opening conversation about navigating the post-bonus depreciation landscape in real estate investing. As the 100% bonus depreciation benefit phases out (down to 60% in 2024), investors need to rethink their tax strategy. Marcus offers a refreshing perspective: sometimes paying some taxes is smarter than spending your last dollar...
Send us a text Laura Ritchie's journey from corporate media executive to real estate mogul exemplifies the power of creativity and determination in building wealth. Starting in 2017 with a simple side hustle, Laura leveraged family connections, thrift store furniture, and a willingness to take calculated risks to rapidly build an 85-unit portfolio now worth approximately $14 million. What makes Laura's approach remarkable is her innovative financing strategies. She shares how she transformed...
Send us a text Brad Chandler opens up about his remarkable dual journey as both a wildly successful real estate investor with 4,500 deals under his belt and as someone who overcame deep-seated personal struggles that once threatened everything he built. The conversation takes a profound turn when Brad reveals how a seemingly routine therapy session for his son's anxiety unexpectedly uncovered his own unresolved childhood trauma. This discovery launched him into a transformative healing journ...
Send us a text What does a dead cat in the ductwork have to do with real estate investing success? As it turns out, quite a lot about perseverance and education in the school of hard knocks. Corey sits down with commercial underwriter Kolten Van Elzen for a fascinating exploration of economic trends and their impact on real estate investment strategy. Their conversation ranges from practical horror stories (like Colton's first flip of a 30-cat hoarder house) to sophisticated economic forecas...
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