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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.
71 Episodes
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Send us a text In this episode of The Wisconsin Investor Podcast, Corey sits down with Chris Hake, a 30+ year Wisconsin real estate investor and founder of Wisco REIA, to break down what actually leads to long-term success in real estate. They dive into real-world lessons from multiple market cycles and unpack why most investors get stuck — even when they’re working hard. In this episode, you’ll learn: • What 30+ years of investing in Wisconsin teaches you about risk and growth • Key lesson...
Send us a text In this episode, Corey opens up about the deals that didn’t go well — the ones that cost real money, real time, and taught real lessons. Because the truth is simple: experience comes from getting punched in the face financially… not from the wins. This week, Corey breaks down several costly mistakes from 2024–2025, including a Jacksonport project that spiraled far beyond the original budget and a series of flips that exposed gaps in process, oversight, due diligence, and team b...
Send us a text The Simple Offer Mistake Costing WI Investors $25K–$30K Per Deal Many Wisconsin investors say, “There are no deals out there.” But in this episode, Corey breaks down why that belief isn’t true—and how one small tweak in your offer formula can instantly make you more competitive. This lesson came from a real coaching conversation with a team member, and the numbers were eye-opening. By using the wrong calculation method, many investors are losing deals and leaving tens of thous...
Send us a text What if saving $5,000 on your next flip is secretly costing you $50,000… or more? This week, Corey breaks down one of the biggest traps Wisconsin investors fall into — doing the work themselves. Swinging hammers. Painting at midnight. Laying floors on the weekends. All in the name of “saving money.” But here’s the truth: speed builds wealth in Wisconsin real estate, not sweat equity. If you’re the bottleneck, you’re slowing deals, missing opportunities, stressing your family, ...
Send us a text Goal Setting for 2026: From Zero to 100 Units in 3 Years | Wisconsin Real Estate Insights 🎯 Ready to crush your 2026 real estate goals? In this episode of The Wisconsin Investor Podcast, Corey Reyment shares his proven strategy for setting and achieving big goals — specifically how he went from zero to 100 units in just three years! Whether you're a beginner or seasoned investor, Corey's actionable framework will help you set clear, achievable goals, navigate the challenges of ...
Send us a text On this episode we dig into how Eddie went from diesel bays to building long-term wealth through Wisconsin rentals — using a simple buy box, steady mentorship from his dad, and a numbers-first approach that keeps emotion out of offers. We also break down today’s rental slowdown, real rent-setting strategy, and why in-house rehab gives local investors a massive edge. 🛠️ Growing up on job sites and learning management from the ground up 💼 Leaving a capped wage job for flexible, ...
Send us a text In this episode of The Wisconsin Investor Podcast, Corey sits down with seasoned investor Ben Keleny, who built a multi-million-dollar portfolio with long-term rentals, short-term rentals, boutique hotels, and even a church renovation. Ben shares how he capitalized on the 2008 market crash and expanded his investments across Wisconsin and South Carolina. Learn about Ben’s strategies for navigating market changes, using the BRRRR method, and leveraging creative financing. He als...
Send us a text Taxes don’t have to be the cost of doing business. Specialized custodian Mikey Liello breaks down how self-directed retirement accounts let you buy rentals, fund flips, and lend privately — compounding gains with powerful tax advantages. We simplify IRC 4975 so you understand what’s allowed, who’s disqualified, and how to structure deals legally. Learn the three clean funding paths — cash, non-recourse leverage, and partnerships — and why the solo 401k is the real estate invest...
Send us a text What if your worst flip could become your best teacher? In this episode, Corey pulls back the curtain on his real estate journey, from corporate sales burnout to building a Wisconsin-based real estate business powered by BRRRR, direct-to-seller, and rent-to-own strategies. No fluff—just the hard lessons, pivots, and small wins that added up to real momentum. 💡 We cover it all: hiring on gut feel, skipping background checks, and learning the hard way why contractors and processe...
Send us a text What if the fastest way to level up your real estate game is to write more offers — sooner — using just a few laser-focused questions? That’s the spark behind this week’s conversation with Joe “Duplex Joe” Gracyalny, a Wisconsin investor who went from teaching and bartending to building wealth through duplexes, and now, self storage. We break down Joe’s real-world path from small multifamily to storage and unpack the mindset, math, and methods that helped him scale without over...
Send us a text We trace Jennie Buah’s path from an underwater condo to a six-figure flip in Green Bay’s Indian Trails, spotlighting the mindset, systems, and financing stack that turned overwhelm into action. This episode breaks down how she built confidence, raised private money, and learned to move fast — even when the numbers weren’t perfect yet. Inside this episode: 💥 Massive imperfect action as a repeatable habit 🏠 Learning at RIAs without drowning in acronyms 🚪 Walking open hous...
Send us a text What separates a stuck investor from a scalable one? 💡 It’s not more hustle—it’s smarter capital. This week, we unpack the four funding buckets that fuel every real estate business: HELOCs, private money, community banks, and hard money. Corey walks through how to stack them for maximum flexibility, minimize risk, and stay competitive in any market. Plus, a real duplex case study that proves—buying right and borrowing smart beats perfect execution every time. 🔥 In This Ep...
Send us a text 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 fear every time. 🔥 Inside This Episode: 📘 Free BRRRR course v...
Send us a text 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 avoid rookie mistakes 🪞 Mr. Sandless: the one-day refinish trick ev...
Send us a text 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 on multiple exits (flip, BRRRR, midterm rental) boosts NOI and long-term wealth ...
Send us a text 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 $20,000 • Partnered in an indoor shooting range that shifted from acqui...
Send us a text 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 using creative financing + other people’s money💪 The mindset ...
Send us a text 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 finalizing the refinance just eight months later. The numbers tell a c...
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...
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