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In 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 move

If 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

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In 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 capital
• Why “the deal attracts the money” is more than just a saying
• The mindset shift that helped Tim leave his W-2 job
• How mentorship accelerated his investing career
• Why networking is the real shortcut in real estate
• How to structure your schedule while building your investing business
• Lessons from investing through multiple market cycles

If 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.com

For off-market investment opportunities across Wisconsin, visit:
👉 WisconsinDiscountProperties.com

Send a text

In 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 wealth

If 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: 414-429-9130

Looking for off-market deals across Wisconsin?
Visit WisconsinDiscountProperties.com to join the exclusive buyer list.

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