WiscoREIA Sheboygan: Deal and Dilemma Workshop – Brainstorm with a Room of Mentors!
Schedule
Wed, 24 Sep, 2025 at 05:30 pm
UTC-05:00Location
1142 Plankview Green Blvd, Sheboygan Falls, WI 53085-3393, United States | Sheboygan Falls, WI
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Deal and Dilemma Workshop – Brainstorm with a Room of Mentors!Have a real estate challenge, deal, or question that you’d love to run by experienced investors? Join us for our Deal and Dilemma Workshop, where you’ll have the opportunity to tap into the collective wisdom of a room full of mentors!
This interactive session is designed to help investors at all levels—whether you’re analyzing a potential deal, facing a roadblock in your business, or just looking for fresh perspectives on marketing, lead generation, or strategy. You’ll have the chance to present your situation, get constructive feedback, and gain valuable insights from both seasoned investors and industry professionals.
How it works:
Sign up at the door if you’d like to present a deal or dilemma.
You’ll be given time to explain your situation.
The room will brainstorm ideas, offer solutions, and share expertise to help you move forward.
Come ready to learn, collaborate, and take your investing to the next level! Whether you participate or just listen in, you’ll walk away with actionable advice and new connections to help you grow your real estate business.
Don’t miss this unique opportunity to get real feedback from real investors—see you there!
Speaker: Chris Hake and Kyle Kauffman
Chris is the founder and visionary of the Madison Real Estate Investors Association (REIA), Master Investor Academy and JSS Mastery Partnership Program. Chris has decades of real estate investing experience and has seen (and smelled) more distressed properties than he cares to admit.
Chris has been a Madisonian for over 49 years and investing in the Madison real estate market for 30 years. Since doing his first house hack in 1994, he has been involved with 100's of house flips, 100’s of rentals, raised over 15 million dollars to fund those deals and had 1000's of students come through his local training and coaching programs. Chris has a master's degree in the school of hard knocks.
Between 2006-2010 Chris taught the Real Estate Investing course at Madison Area Technical College, which saw 100's of students come through his classes. In July 2012, Chris founded The Madison REIA and in July 2021 merged with Wisco REIA which now has 10 REIA locations across Wisconsin, bringing the combined membership to well over 500!
Chris's company Just Simple Storage, LLC owns ten facilities and manages 1000+ self-storage units in WI, IL and MI. Chris also started a commercial storage development company in 2024.
On a personal note, Chris and his wife, Suzanna, have three children, Tyler, Tanner and Trelan. He also has two dogs, Kona and Hemi. Chris loves classic muscle cars (Corvettes), all outdoor sports, especially golf, and fishing. As a husband, father, businessman, and real estate investor, Chris holds true to his core values and lives his Life and Business Vision plan.
Kyle Kaufman is a business owner, attorney, real estate investor, and host of the Meaningful Ideas Trading Club. Kyle was born and raised in Wisconsin. He grew up wanting to help people. He has discovered his life’s purpose to help families in Wisconsin and to provide individuals with commercial space for their business, and residences for people to live.
In 2005 Kyle started practicing law. He handled almost all aspects of the law. Early in his career he took on landlord and tenant matters, and civil disputes involving real estate. He started to advise people starting their real estate portfolios, and drafted documents for investors to use in their businesses and with tenants and property managers.
In 2010 Kyle became a one-third owner of the law firm, now known as HKK Law Offices Family Law (www.hkklawoffices.com). Kyle’s practice shifted to family law sometime around 2018, as more and more people called seeking his assistance. Kyle became fascinated with all the financial information he discovered while representing individuals in divorce matters and financial disputes between former significant others. He started to study more thoroughly on the issues of real estate, business, taxes, and more.
WiscoREIA’s Sheboygan Meeting Always Meets on the 4th Wednesday of the Month from 5:30 pm to 8:15 pm!
Agenda
5:30 PM – Registration Check-In & Networking
• Informal networking with fellow investors
6:00 PM – Meeting Kickoff
• Welcome by Host and/or Co-Host
• WiscoREIA PowerPoint / announcements and updates
• Sponsor Introductions
• Haves & Wants – Share deals, services, and resources
6:30 PM – Deal Case Study
• Breakdown of a real deal with teachable moments (good, bad, ugly)
7:00 PM – Networking Breakouts
• Guest Orientation with Host
• Member & Sponsor general breakout for continued connection
7:15 PM – Main Presentation
• Host introduces Guest Speaker
8:15 PM – Closing Remarks
• Final thoughts and upcoming events
• Invitation to the "Meeting After the Meeting" for more networking
Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!
Meeting Location:
Legend Larry's
1142 Plankview Green Blvd
Sheboygan Falls, WI 53085
Please enjoy food, drinks, and TIP YOUR SERVERS!
6:00 pm - 7:00 pm - Doors open early for Networking
7:00 pm - 9:00 pm - Speaker Presentation
The meeting ends at 9:00 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***
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Where is it happening?
1142 Plankview Green Blvd, Sheboygan Falls, WI 53085-3393, United StatesEvent Location & Nearby Stays:
