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 Hake – WiscoREIA Owner

Real Estate Investor | Educator | Coach | Entrepreneur

Chris Hake was the founder and driving force behind the rise of Madison REIA, which he launched in August 2012. In 2021, he merged Madison REIA with WiscoREIA, expanding its reach to ELEVEN monthly REIA meeting locations across Wisconsin and growing its community base of guests and members to over 1000 active investors and entrepreneurs.

With more than 30 years of hands-on experience in real estate, Chris is passionate about giving back. He continues to lead monthly meetings in Madison and frequently shares the lessons he's learned from decades "in the trenches." Chris is most energized by helping new investors discover if real estate is the right path for them, and if so, guiding them to the best possible start for long-term success. He speaks regularly at events throughout Wisconsin and across the U.S., covering topics on real estate investing, business, and personal growth.

A lifelong Madisonian, Chris began his investing journey with a house hack in 1994 and since been involved in hundreds of flips and rental properties. Over the years, he has raised more than $20 million to fund deals and has trained thousands of students through his local coaching programs. From 2006 to 2010, he also taught the Real Estate Investing course at Madison Area Technical College, where hundreds more learned the fundamentals from his real-world approach.

Today, Chris focuses much of his energy on growing Just Simple Storage LLC, a storage investment company he founded that now owns 900 units across 9 facilities in Wisconsin, Illinois, and Michigan.

Outside of real estate, Chris is a devoted husband to his wife, Suzanna, and a proud father to their three boys: Tyler, Tanner, and Trelan. He’s also a fan of classic muscle cars (especially Corvettes and Mustangs), and enjoys outdoor adventures like golf, fishing, and pickleball. At his core, Chris is committed to living out his Life and Business Vision each day, guided by strong values and a passion for helping others succeed.

Feel free to reach out to Chris at chrishake@gmail.com

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 Hake – WiscoREIA Owner

Real Estate Investor | Educator | Coach | Entrepreneur

Today, Chris focuses much of his energy on growing Just Simple Storage LLC, a storage investment company he founded that now owns 900 units across 9 facilities in Wisconsin, Illinois, and Michigan.

Feel free to reach out to Chris at chrishake@gmail.com

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 Hake – WiscoREIA Owner

Real Estate Investor | Educator | Coach | Entrepreneur

Today, Chris focuses much of his energy on growing Just Simple Storage LLC, a storage investment company he founded that now owns 900 units across 9 facilities in Wisconsin, Illinois, and Michigan.

Feel free to reach out to Chris at chrishake@gmail.com

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: Rehabbing for Profit: Flip or Hold? (14 Sep 2026)

Mon, 14 Sep 2026 23:30:00 GMT

Rehabbing for Profit: Flip or Hold?

Click here to pre-register!

Every rehab project starts with a big question: Should you flip it for aquick profit, or hold it for long-term cash flow and wealth building?

Join us for a dynamic panel discussion featuring experienced real estate investors who have successfully used both strategies in today's market. Our panelists will share real-world experiences, lessons learned, successes, mistakes, and the factors they consider when deciding whether a property is best suited for a flip or a buy-and-hold investment.

During this interactive discussion, you'll learn:

✅ How to evaluate a rehab project and determine the best exit strategy
✅ The numbers and metrics investors use to make profitable decisions
✅ Current market conditions that influence flipping versus holding
✅ Common mistakes that can eat away at your profits
✅ Financing considerations for both strategies
✅ Real examples of deals that were flipped—and others that became long-term rentals
✅ How experienced investors balance cash flow, equity growth, and risk

Whether you're brand new to rehabbing or already working on deals, this session will provide practical insights you can immediately apply to your own investing business.

Bring your questions, connect with local investors, and gain valuable perspective from those actively doing deals in today's market.

Don't miss this opportunity to learn how successful investors decide when to flip, when to hold, and how to maximize profits either way!

Panelists: TBD

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 Hake – WiscoREIA Owner

Real Estate Investor | Educator | Coach | Entrepreneur

Today, Chris focuses much of his energy on growing Just Simple Storage LLC, a storage investment company he founded that now owns 900 units across 9 facilities in Wisconsin, Illinois, and Michigan.

Feel free to reach out to Chris at chrishake@gmail.com

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 That Gets You More Deals & More Profits (9 Nov 2026)

Mon, 09 Nov 2026 23:30:00 GMT

Negotiation That Gets You More Deals & More Profits

Click here to pre-register!

Most investors lose deals long before the seller ever says “no.”

Why? Because they negotiate too timidly, too emotionally, or too quickly overpay just to get the deal done. In this powerful session, you’ll learn how successful investors negotiate with confidence, uncover real seller motivation, and structure conversations that lead to more signed contracts and bigger profits.

This isn’t about “lowballing” sellers. It’s about understanding people, solving problems, and creating win-win opportunities that actually close.

In this training, you’ll discover:

✅ Why most investors accidentally negotiate against themselves

✅ How to talk to motivated sellers without sounding desperate or pushy

✅ How to uncover the seller’s REAL problem — not just their asking price

✅ Why the way you present an offer can make or break the deal

✅ Simple negotiation techniques that create movement and momentum

✅ How to stay calm, professional, and in control when sellers push back

✅ Why negotiation is often the difference between a dead lead and a profitable deal

Whether you’re brand new or already doing deals, this session will help you become more confident in seller conversations and better equipped to close profitable opportunities.

If you want more deals without simply offering more money, you do not want to miss this one.

Speaker: Tom Zeeb

Tom Zeeb is a national real estate investing speaker and mentor who helps investors create more deals by mastering the two areas most people never systemize: consistent deal flow and seller conversations.

Back in 2001, Tom was broke and stuck in a 9-to-5. A near-death experience while whitewater rafting forced a hard reset, and he committed to building a life with more control. Real estate investing became the vehicle, but it was not a smooth start. His first deal almost took him under too.

Hundreds of deals later, Tom now teaches the same negotiation, marketing, and execution frameworks that set him free, in a way that is simple, structured, and immediately usable.

Tom works with investors at every level:

• Beginners who are stuck in confusion and never get their first deal.

• Intermediate investors who have done a deal or two but cannot get consistent.

• Advanced investors who built something that makes money but not freedom, and need to re-engineer the business.

Tom's approach is direct and practical. He focuses on the core elements that drive results:

• Finding motivated sellers with repeatable marketing.

• Turning leads into deals through negotiation structure and clean seller conversations.

• Installing weekly execution rhythms so the business stops being random.

It is amazing what a few targeted tweaks to the core elements of a business can do.

Tom teaches investors how to identify those elements and implement them, so their deals, profits, and time freedom finally match the reason they got into real estate in the first place.

Speaker resources: tomzeeb.com/speaker-resources

Contact: tom@tomzeeb.com

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 Hake – WiscoREIA Owner

Real Estate Investor | Educator | Coach | Entrepreneur

Today, Chris focuses much of his energy on growing Just Simple Storage LLC, a storage investment company he founded that now owns 900 units across 9 facilities in Wisconsin, Illinois, and Michigan.

Feel free to reach out to Chris at chrishake@gmail.com

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!