WiscoREIA Madison: Deal and Dilemma Workshop – Brainstorm with a Room of Mentors!

Deal and Dilemma Workshop – Brainstorm with a Room of Mentors!

Click here to pre-register!

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

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.

WiscoREIA's Madison Meeting Always Meets on the 2nd Monday of the month from

5:30 pm - 8:30 pm!

Hosts: Chris Hake & Ken Collins

Ken's journey began in the field of social work and psychotherapy, where he dedicated a decade to helping others navigate their personal challenges. Seeking new horizons, he transitioned into the tech industry, joining Hewlett-Packard. Over the next 24 years, he evolved from a Computer Engineer to a Global Project Manager, culminating in his leadership of the Global Sales Lead program, which under his stewardship generated nearly $1 billion in sales each year.

In 2016, Ken pivoted to real estate investing, initially employing the BRRRR (Buy, Rehab, Rent, Refinance, Repeat) method. Upon retiring from corporate life, he focused on creative deal structuring, mastering techniques like Subject-To (Sub2), Lease/Options, and Land Trusts. His portfolio includes over 50 Real Estate  transactions in the last 8 years, ranging from mobile homes, single family and  multifamily properties, showcasing his versatility and expertise in the real estate market.

Ken credits much of his real estate knowledge and sharpened skills to his active participation in the many WiscoREIA Madison education programs. Through joining their Coaching Program, completing the Blueprint course, and engaging in numerous educational opportunities including hands-on property tours and weekend training events from a variety of speakers sponsored by the REIA, Ken has continuously expanded his expertise in real estate.

Ken is renowned for his proficiency in lead generation and deal negotiation, leveraging a multitude of creative strategies to craft win-win scenarios in real estate. He now steps into his role as a coach for aspiring real estate investors, eager to share his knowledge and experience. He is always on the lookout for personal growth opportunities, being an active member of groups like Lifeonaire and the Generations of Wealth Mastermind group, which further fuel his passion for continuous learning and development.

With a life that beautifully blends family, community, technology, and real estate, Ken Collins is not just a coach but a mentor who understands the art of building wealth through real estate while maintaining a life of balance and fulfillment.