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
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,...
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...
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...
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...
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...
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—al...
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, Refin...
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: ...
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 re...
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 childho...
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&apos...
Imagine never having to beg a bank for funding again. What if you could consistently secure real estate deals with private lenders without ever asking for money? That's exactly what Jay Conner has mastered, and he shares his revolutionary approach in this eye-opening episode.
Jay reveals how he's built a portfolio of 47 private lenders providing $8.5 million in capital for his real estate business, ...
Mike Higgins opens up about his transformative journey from personal trainer to thriving real estate investor in Wisconsin, revealing the strategic shifts that made all the difference in his business. Far from just another "how I got started" story, this conversation delivers practical wisdom on maximizing profitability in today's market.
Want to know why some investors consistently snap up dea...
Securing financing remains the biggest hurdle for most aspiring real estate investors. When traditional banks say "no," where do you turn? In this eye-opening conversation, mortgage expert Aaron Kramer reveals the financing secrets that have helped hundreds of investors build substantial portfolios, even without perfect credit or W2 income.
Aaron breaks down how house hacking creates a perfect entry...
Matt and Catie Fihn transformed their family's future through real estate investing in just three short years. Starting with a simple conversation between moms at a playdate, they discovered a path that would ultimately free both of them from their corporate careers and allow them to be present for their young children's formative years.
Their approach wasn't about getting rich quick or buildin...
Andy Boehm pulls back the curtain on his 15-year real estate investing journey across Northeast Wisconsin, revealing the counterintuitive strategies that have built his success. What began as a career in real estate sales during the foreclosure boom evolved into a profitable investing operation when Andy noticed a simple truth: the investors buying properties were making substantially more money than he was earning in...
In this enlightening episode, we dive deep into the remarkable journey of Mark Pomeranke, a pioneering force in the hotel industry. Starting from a meager $23 credit balance, Mark embarked on an ambitious path in hotel development amidst the tumultuous period of the financial crisis. His innovative approach led to the establishment of a hospitality brand that flourished by focusing on small towns overlooked by larger ...
Dave Zouski shares his real estate journey, emphasizing strategic investing and the importance of relationships in navigating the market. His insights on the buy-and-hold strategy, effective contractor management, and the significance of networking provide valuable guidance for both new and seasoned investors.
• Highlighting the transition from agent to investor
• Emphasizing the need for strong banking...
Zach "Big Money" Morgan reveals the art of transforming a modest start into a thriving real estate empire. Inspired by industry stalwarts like Grant Cardone and Bigger Pockets, Zach shares his impressive journey from a traditional job to owning 52 long-term rental properties. We dive into the nuances of sustaining active income through strategic property flips and wholesales, all while navigating the challen...
Ever wondered how an everyday couple from Shawano, Wisconsin, turned their first duplex into a thriving real estate investing business? Meet Cayla and Brandon Farley, whose journey began in 2016 with a house hacking strategy, leading to a thriving investment portfolio. Listen as they recount their early days, navigating unexpected challenges like mountains of dog hair, and how these experiences laid a solid foundation...
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