My Most Expensive Real Estate Mistakes (So You Don’t Repeat Them)

Send us Fan MailIn 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 bandwidth.If you're scaling, flipping, or thinking about jumping into a new asset type, these lessons will save you money, frustration, and months of wasted time.In this episode, we cover:The Jacksonport deal: why new asset classes require deeper due diligenceHow skipping well/septic inspections cost $45K–$60KWhy “moving fast” without structure is actually chaosHow tight numbers push investors into bad decisionsThe hidden bottlenecks inside growing teamsWhy contractors must be checked in person — or by someone who can beHow to hire, delegate, and avoid burning your people outThe real cost of doing too much yourselfThese weren’t rookie mistakes — they were scaling mistakes. And if you're growing your Wisconsin real estate business, you’re going to face the same traps. This episode is here to help you avoid them.If you want 2026 to be your least stressful and most profitable years yet, start with the lessons that cost Corey tens of thousands — so they don’t cost you anything.Quick reminder — our New Year Giveaway winners will be announced on January 1st, and there’s still time to enter if you haven’t jumped in yet! More details on our pinned post on our Facebook/Instagram.👉 If this helped you, subscribe on YouTube, drop a review on Apple or Spotify, and share the episode with another WI investor.Your support helps us grow the community and bring you more real, honest, and actionable content.