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

Stop Waiting for Money in Real Estate (Do This Instead)