Podcast
The Wisconsin Investor
Hosted by Corey Reyment · EN
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.
29episodes
Episodes
Newest firstAll episodes
Your Edge Isn't Experience: How to Find Your Niche in Wisconsin Real Estate
1w ago00:18:17Tap to summarizeSend us Fan MailMost new investors follow the same playbook and wonder why they can't compete. The ones who break through faster are the ones who figure out where they already have an advantage before they ever buy their first deal.Reese breaks down how to identify your niche in real estate, why it has nothing to do with knowing everything, and why your first deal is supposed to be messy.What's covered:Why copying someone else's blueprint is the fastest way to stay stuck, and what to do insteadHow a trades background, a corporate career, or even a sales job gives you a built-in edge in real estateWhy your first deal's profit per hour is going to look rough, and why that's actually fineThe three types of leverage that matter more than hustle: money, people, and systemsHow experienced investors run seven or eight projects at once without losing their minds (and how you get there too)Reese also shares how he got his foot in the door early by flying drone footage for realtors for free. No construction experience, no capital network. Just a skill plugged into the right relationship.If you're getting started and feeling behind, this one's for you.Check out Wisconsin Discount Properties for off-market deals every Monday morning: WisconsinDiscountProperties.com
Transcribe →Hard Money vs Commercial Lending… Which One Actually Makes You More Money?
2w ago00:36:37Tap to summarizeSend us Fan MailMost investors default to hard money because it’s simple.But what if that’s actually costing you more than you think?In this episode of The Wisconsin Investor, Reese Brown sits down with commercial lender Chad Miller of Bristol Morgan Bank to break down the real differences between hard money lending and commercial lending, and when each one actually makes sense for your deal.They walk through real examples, numbers, and scenarios that show how commercial lending can sometimes require more upfront capital, but actually leave you with less money in the deal over time.Here’s what you’ll learn: • The key differences between hard money and commercial lending • Why commercial loans are more relationship-based, and why that matters • What “85% of project cost” really means and how it works • How draw schedules and rehab funding actually play out • Why some investors end up with less cash in a deal using commercial loans • When it still makes more sense to use hard money • How to build a banking relationship that unlocks better terms over timeThey also dive into how community banks evaluate deals, what new investors should do before reaching out, and how experienced investors can get more flexible financing as they grow.One of the biggest takeaways? The best loan option isn’t always the simplest one, and understanding both can completely change how you structure your deals. If you’re flipping houses, building a rental portfolio, or just trying to figure out how to fund your next deal more efficiently, this episode is packed with practical insight you can actually use.
Transcribe →Is the Housing Market Slowing Down… or Is This Your Opportunity? (Green Bay Data Breakdown)
3w ago00:26:04Tap to summarizeSend us Fan MailIs the real estate market finally cooling off… or are investors just getting nervous?In this episode of The Wisconsin Investor, guest host Reese Brown sits down with commercial lender Kolten VanElzen to break down exactly what’s happening in the Green Bay housing market right now, using real data, real trends, and real investor insight.They dig into what most people are feeling in today’s market versus what the numbers actually show. From rising days on market to tight inventory and steady price growth, this episode separates perception from reality.Here’s what you’ll learn: • Why listings are slightly down, but not in the way people think • What rising days on market really says about today’s buyers • Why affordability is becoming the biggest factor in deal flow • How new construction pricing is shaping the entire market • What interest rates are likely to do over the next 12 months • Why Northeast Wisconsin continues to outperform most U.S. marketsOne of the biggest takeaways? Even with global uncertainty, higher rates, and affordability challenges, deals are still happening and prices are still trending upward in Green Bay. If you’re an investor waiting on the sidelines or trying to figure out your next move, this episode gives you a clear, data-backed look at where things stand and where they could be heading.The market hasn’t stopped, it’s just shifting.
Transcribe →PART 2 - 10 Deals to Make You a Millionaire | Live Deal Analysis Breakdown
4w ago00:29:04Tap to summarizeSend us Fan MailIn 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 dealsUsing 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
Transcribe →From Principal to 6 Doors in 12 Months, The Power of Massive Action in Real Estate
Apr 1400:41:03Tap to summarizeSend us Fan MailIn 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 journeyIf 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.
Transcribe →How 10 Deals Can Make You a Millionaire
Apr 700:41:00Tap to summarizeSend us Fan MailWhat 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 portfolioCorey 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.
Transcribe →How to Scale Your Real Estate Business Without Doing Everything Yourself
Mar 3100:34:25Tap to summarizeSend us Fan MailAre 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 freedomCorey 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
Transcribe →How to Navigate Tax-Efficient Real Estate Exits: Insights from Brandon Bruckman
Mar 2400:54:42Tap to summarizeSend us Fan MailIn 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 moveIf 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
Transcribe →Stop Waiting for Money in Real Estate (Do This Instead)
Mar 1700:44:17Tap to summarizeSend us Fan MailIn 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.comFor off-market investment opportunities across Wisconsin, visit: 👉 WisconsinDiscountProperties.com
Transcribe →Flipping vs Rentals: What Most Investors Get Wrong
Mar 1000:54:30Tap to summarizeSend us Fan MailIn 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 wealthIf 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: 414-429-9130Looking 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
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