Educating Wisconsin Investors

WiscoREIA Hudson: Navigating the Changes in the Insurance Industry

  • 23 Sep 2025
  • 6:30 PM
  • Hop and Barrel Brewing

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  • You have not attended any WiscoREIA meetings. The first meeting is free!
  • You have attended 1 WiscoREIA meeting for free.

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Navigating the Changes in the Insurance Industry

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The insurance landscape is shifting—and it's impacting real estate investors in a big way.


Join us to uncover why these changes are happening, what they mean for your property coverage, and most importantly, how to adjust your strategy so you can continue growing your portfolio with confidence.

Here’s what we’ll cover:

Why the Industry is Shifting – Get a clear picture of the economic and environmental factors behind the changing insurance landscape.

Rising Costs and Reduced Coverage – Learn how these changes are directly impacting property investors—and what you can do about it.

Adapting Your Investment Strategy – Discover ways to reposition your approach while still growing and protecting your portfolio.

Policy Review Essentials – Know what to look for in your policies to avoid costly gaps in coverage.

Working with the Right Carriers – Understand how to vet and select insurers that align with your investment goals.

Risk Management in a New Era – Proactively safeguard your assets against increasing insurance-related challenges.


In today’s evolving market, informed investors are the ones who stay ahead. Don’t let these changes catch you off guard—learn how to adapt, plan, and continue building with confidence.


Speaker: Zach Culbertson

Owner and Insurance Agent for The DC Team at COUNTRY Financial for the last 8 years. Zach works in all areas of insurance but specializes in working with real estate investors and business owners. His agency helps clients insure their home, vehicles, rental properties, and helps them protect their families with life insurance and retirement planning. Zach is a native to Eau Claire, WI but now resides in Waukesha, WI with his wife and 2 kids.



WiscoREIA’s Hudson Meeting Always Meets on the 4th Tuesday of the month from

6:30 pm - 8:30 pm!


Hosts: Alyssa Burton & Rebekah Chamberlain

Alyssa is the founder of Inspired Investments LLC and a dual licensed agent with Green Forest Realty and Chippewa Valley Real Estate, operating in Indiana and Wisconsin. She has cultivated knowledge across various fields within the real estate realm. With experience as an investor in single-family homes, multifamily properties, small apartments, self-storage facilities, and vacant land, Alyssa leverages her insights to empower her clients. Through Inspired Investments, she provides property management and project management for flips, and has been excelling in the field since 2020. Alyssa's favorite thing about real estate is that there are so many strategies and types of investments to get into. She is dedicated to the belief that Real Estate can be used as a powerful tool to create positive change, and her greatest satisfaction is using what she has built to help do the most amount of good. Alyssa is always looking to grow and learn more and enjoys bringing like-minded individuals together.


Always an entrepreneur, Rebekah spent the first decade of her career starting and building an organic dairy farm from the ground up.  The business went from $0 to just shy of $1M in gross revenue over that decade.


7 years ago, Rebekah pivoted her efforts into Real Estate.  Passionate about building a life and business that fit around her children instead of her business running her- she is grateful to only have created that balance for herself, but to also get to help others do the same.  Rebekah has specialized in working with investors and commercial transactions and is using that experience helping others to begin building her portfolio.


On a personal note, Rebekah is a busy mom to four beautiful children. Leading by example and leaving a legacy for her children is the “why” that inspires her to be better every day. You can find Rebekah enjoying time with her family, running, hiking, biking, soaking in the outdoors, reading, cooking or baking when she’s not busy with work.



Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!



Meeting Location:

Hop and Barrel Brewing

310 2nd St

 Hudson, WI 54016


Please enjoy drinks, and TIP YOUR SERVERS!

6:30 pm - 7:00 pm - Doors open early for Networking

7:00 pm - 8:30 pm - Speaker Presentation


The meeting ends at 8:30 PM, but we’ll continue with an informal after-meeting for anyone who’d like to stay.


You can stay after the meeting as well to network! Remember to bring your deals!



Members are always FREE! Your first meeting with WiscoREIA is FREE!

 After your first meeting, Non-Members are $30.00.



***Make sure to pre-register - We are now Cashless***

Click here to pre-register!

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