WiscoREIA upcoming events

WiscoREIA Madison: Boutique Assisted Living: The Quiet Cash Flow Business Hiding in Plain Sight (8 Jun 2026)

Mon, 08 Jun 2026 23:30:00 GMT

Boutique Assisted Living: The Quiet Cash Flow Business Hiding in Plain Sight

Join us as Brandon pulls the curtain back on one of the most overlooked and fast growing niches in real estate, boutique assisted living.

He is going to show what this business really looks like, how these homes work, how he finds and buys them, how he finances them, how he sets them up, and how they cash flow like a rental, but with a much bigger long term need behind them.

He is also going to talk about the "silver tsunami" that is happening right now as millions of seniors age into needing care and why small boutique assisted living homes are filling a massive gap that big box facilities are failing at. He will share why this is a real business, how normal people can get involved, and why this asset class is growing into a multi billion dollar space with huge demand over the next several years.

Register now and make sure not to miss this one!

Speaker: Brandon Schwab

Brandon Schwab is a lifelong entrepreneur with 28 years of self-employment experience and a passion for solving broken systems. Since age 15, he’s focused on identifying problems and creating action-driven solutions. His current mission is transforming the senior living industry through Shepherd Premier Senior Living, offering small, home-style communities with significantly higher caregiver-to-resident ratios than traditional facilities.

As Founder and CEO, Brandon is driven to replace family guilt with peace of mind by delivering exceptional care. His goal is to build 300 homes by 2035 to help meet the growing demand for quality senior housing. Known for his energy, clarity, and no-nonsense approach, Brandon continues to raise capital, engage investors, and advocate for better senior care—because doing what’s right can’t wait.

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

5:30 pm - 8:15 pm!

Hosts: Chris Hake & Ken Collins

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.

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.

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

Our 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

Location:

Vintage Brewing Co. Madison

674 S Whitney Way

Madison, WI 53711

Please enjoy food, drinks, and TIP YOUR SERVERS!

The meeting ends at 8:15 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!

Our doors are open to EVERYONE!

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

Click here to pre-register!

WiscoREIA Madison: How to Make SIX Figures in the Next SIX Months (13 Jul 2026)

Mon, 13 Jul 2026 23:30:00 GMT

How to Make SIX Figures in the Next SIX Months

Click here to pre-register!

What would it take for you to generate six figures in the next six months?

In today’s market, success isn’t about working harder—it’s about having the right strategy, focusing on high-impact activities, and executing with clarity and consistency. This powerful session is designed to show you exactly how to build momentum, create predictable income, and scale your real estate business faster than you thought possible.

You’ll learn how to identify the fastest paths to income, eliminate the distractions that hold most investors back, and focus on the actions that truly move the needle. From finding opportunities to structuring deals and closing with confidence, this session will give you a clear, actionable roadmap to hitting your next financial milestone.

In this session, you’ll discover:

✅ How to build a predictable and duplicatable business working directly with sellers
✅ The Homeowner 10 Options and how to position yourself as a problem-solver
✅ Proven scripts to get homeowners to open up—and want to work with you
✅ The mindset shift from “buying houses” to creating opportunities homeowners say YES to
✅ How to handle objections and turn resistance into deals
✅ Strategies for high-equity partnering that can generate significant profits per deal
✅ How to find the right deals fast—and avoid losing money
✅ Seven underutilized strategies that can transform your business
✅ What’s coming in the market (including foreclosures) and how to prepare
✅ How AI is impacting real estate investing and how to stay ahead

Whether you’re just getting started or ready to break through to the next level, this session will challenge you to think bigger, move faster, and take action.

If you’re serious about creating consistent income and building a real estate business that works, this is one you don’t want to miss.

Speaker: Bill Twyford

Bill Twyford and Dwan Bent-Twyford are renowned real estate experts who have gained popularity through their informative and educational seminars. They have been instrumental in teaching people the art of real estate investing, helping individuals achieve financial freedom through their proven strategies.

Bill Twyford, along with his wife Dwan Bent-Twyford, has been conducting real estate seminars for 25 years. Since they are active investors for over 30 years, their seminars provide a comprehensive guide to real estate investing, covering everything from finding the right deals, in the right areas whether it is creative financing or just straight wholesaling a contract. They are experts at teaching beginners the fundamentals of real estate investing, as well as helping experienced investors hone their skills and take their game to the next level. Bill and Dwan specialize in creating six-figure and seven-figure incomes for their students.

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

5:30 pm - 8:15 pm!

Hosts: Chris Hake & Ken Collins

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.

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

Our 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

Location:

Vintage Brewing Co. Madison

674 S Whitney Way

Madison, WI 53711

Please enjoy food, drinks, and TIP YOUR SERVERS!

The meeting ends at 8:15 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!

Our doors are open to EVERYONE!

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

Click here to pre-register!

WiscoREIA Madison: Negotiation Workshop with Derek Dombeck (10 Aug 2026)

Mon, 10 Aug 2026 23:30:00 GMT

Negotiation Workshop with Derek Dombeck

Click here to pre-register!

The difference between an average deal and a great deal?

The conversation.

Step into a high-energy, hands-on Negotiation Workshop with seasoned investor Derek Dombeck and learn exactly how top dealmakers structure winning agreements directly with sellers.

Derek will break down the psychology, strategy, and tactical moves behind profitable negotiations — then show you how it’s done live. Yes, real negotiation calls during the meeting. No scripts. No theory. Just real-time decision making, objection handling, and deal structuring in action.

You’ll walk away knowing how to:

✅ Control the conversation without being pushy

✅ Uncover seller motivation fast

✅ Structure creative terms that increase your margins

✅ Handle objections with confidence

✅ Close more deals without racing to the lowest price

If you want sharper skills, stronger margins, and the confidence to lead every seller conversation, this is the room you need to be in.

Speaker: Derek Dombeck

Derek has been a successful Investor since 2002. He’s been through the ups and downs of the markets and has the scars to prove it.

Derek has been involved in hundreds of transactions in his career. He’s done wholesaling, flipping, landlording, lending and countless other investment strategies throughout the years.

Derek loves negotiating with sellers. He loves to put together creative solutions for sellers that few other investors can put together.

Derek loves giving back to the real estate community. Derek is also a coach and mentor who has a passion for helping others be successful too.

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

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

5:30 pm - 8:15 pm!

Hosts: Chris Hake & Ken Collins

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.

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

Our 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

Location:

Vintage Brewing Co. Madison

674 S Whitney Way

Madison, WI 53711

Please enjoy food, drinks, and TIP YOUR SERVERS!

The meeting ends at 8:15 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!

Our doors are open to EVERYONE!

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

Click here to pre-register!