30 Years of Lessons Learned: The Highs, the Lows, and the Landmines with Chris Hake
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You’re Invited to a Raw and Powerful Presentation from Chris Hake!!
After 30 years of entrepreneurial grit, real estate wins and losses, and life-altering challenges, Chris Hake is opening up and sharing the journey that shaped him as a man, investor, and leader.

Click here to watch Chris' message for you!
In this powerful 1-hour session, Chris will reflect on:
· Becoming a millionaire… and losing it all in bankruptcy
· Battling chronic health issues and suicidal thoughts
· Finding identity and hope through faith in Jesus
· The most impactful books that shaped his path (The Bible, The Slight Edge, The One Thing)
· The importance of a written vision plan for your life and business
· Why coaches, mentors, and mastermind groups are non-negotiables
· His Top 10 Game Changers over 3 decades
· The 3 most essential ingredients for lasting success
· What he would say to his 30-years-younger self if given one chance
Whether you’re just getting started or scaling your next mountain, this talk will challenge, inspire, and equip you with real stories and real strategies to navigate your own journey—personally, professionally, and spiritually.
“If my story helps one person avoid a landmine or rediscover hope, then it’s worth every scar.” – Chris Hake
Come hear the hard truths, the big wins, the brutal setbacks—and the redemption woven throughout it all.
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: Ken Collins & Chris Hake

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.
Our Agenda:
5:30 pm - Check in at the reception desk, visit with your friends and colleagues, get settled in to start
6:00 pm - Welcome from Chris Hake
6:05 pm - Ken Collins - Creative Mastermind topic (group participation)
6:50 pm - Chris Hake - Intro WiscoREIA, Sponsors, Haves & Wants
7:15 pm - Networking breakout - (get to know other members & guest)
7:25 pm - Announcements
7:30 pm - Let's Network!
8:30 pm - Meeting adjourned, closing comments by Chris Hake
Make sure to bring tons of business cards as you will be meeting with people that you want to get to know!
Meeting Location:
HQ (Headquarters Bar & Restaurant)
101 Concord Dr
Oregon, WI 53575
Please enjoy food, drinks, and TIP YOUR SERVERS!
You can stay after the meeting as well to network! Remember to bring your deals!
The meeting ends at 8:30 PM, but we’ll continue with an informal after-meeting for anyone who’d like to stay.
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!