WiscoREIA upcoming events

WiscoREIA Milwaukee: Exploring AI Tools for Real Estate Investors (27 Apr 2026)

Mon, 27 Apr 2026 22:30:00 GMT

Exploring AI Tools for Real Estate Investors

Artificial Intelligence is transforming the way we work—and real estate investors are already putting it to use. From deal analysis and research to marketing and property management, AI tools are quickly becoming must-have resources for anyone serious about scaling their business.

This month, we’re hosting an interactive discussion on the AI tools investors are using right now. This won’t be a sit-back-and-listen session—we’ll have someone live on the computer pulling up sites and tools as they’re mentioned, so you can see them in action.

✅ Discover tools that can save you time and boost efficiency
✅ Learn how fellow investors are applying AI in real-world scenarios
✅ Share your own go-to resources and success stories

Whether you’re already experimenting with AI or just starting to explore what’s out there, you’ll leave with actionable insights and practical tools to take your investing to the next level.

Speaker: 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.

WiscoREIA’s Milwaukee Meeting Always Meets on the 4th Monday of the Month from

5:30 pm - 8:15 pm!

Host: 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.

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

Meeting Location:

Homewood Suites by Hilton

11320 W Burleigh St

Wauwatosa, WI 53222

Please enjoy food, drinks, and Tip Your Servers!

5:30 pm - 6:00 pm - Doors open early for Networking

6:00 pm - 8:15 pm - Speaker Presentation

The meeting ends at 8:!5 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***

Click here to pre-register!

WiscoREIA Milwaukee: Real Estate Business Mastery: Strategies, Legal Tips & Tax Secrets (25 May 2026)

Mon, 25 May 2026 22:30:00 GMT

Real Estate Business Mastery:

Strategies, Legal Tips & Tax Secrets

Click here to pre-register!

Ready to turn your real estate investing into a thriving business? Join us for an insider session packed with practical strategies, expert tips, and lessons learned from experienced investors.

In this session, you’ll discover:

✅ Smart strategies to build and scale your real estate business efficiently

✅ Legal essentials every investor must know to protect their investments

✅ Tax tips to maximize profits and minimize risks

✅ Real-world advice to avoid common mistakes that can cost time and money

Whether you’re just starting out or looking to take your portfolio to the next level, this session will equip you with the tools and confidence to grow your business the right way.

Speaker: Amy Farrow

Amy Farrow is an attorney and real estate investor with 25+ years of experience, representing business owners, banks, and real estate professionals in litigation and transactions. She has closed hundreds of residential and commercial real estate deals and has been flipping properties since 1999.

A graduate of the University of Wisconsin (undergrad and law school), Amy began her legal career in Columbia, Sauk, and Dane County before joining the Department of Justice as an FBI Special Agent in Oklahoma City. After five years, she returned to

Wisconsin to continue practicing law in southeastern Wisconsin.

Amy enjoys time with her four children and two dogs, traveling to National Parks with her husband, and participating in Tough Mudder and Spartan races. A commercial pilot, she is currently looking to buy a plane for new adventures. She also serves on the board of a nonprofit supporting breast cancer survivors and their families.

WiscoREIA’s Milwaukee Meeting Always Meets on the 4th Monday of the Month from

5:30 pm - 8:15 pm!

Host: Chris Hake

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!

Meeting Location:

Homewood Suites by Hilton

11320 W Burleigh St

Wauwatosa, WI 53222

Please enjoy food, drinks, and Tip Your Servers!

5:30 pm - 6:00 pm - Doors open early for Networking

6:00 pm - 8:15 pm - Speaker Presentation

The meeting ends at 8:!5 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***

Click here to pre-register!

WiscoREIA Milwaukee: How to Make SIX Figures in the Next SIX Months (22 Jun 2026)

Mon, 22 Jun 2026 22:30:00 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!

Host: Chris Hake

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!

Meeting Location:

Homewood Suites by Hilton

11320 W Burleigh St

Wauwatosa, WI 53222

Please enjoy food, drinks, and Tip Your Servers!

5:30 pm - 6:00 pm - Doors open early for Networking

6:00 pm - 8:15 pm - Speaker Presentation

The meeting ends at 8:!5 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***

Click here to pre-register!

WiscoREIA Milwaukee: Investor Panel Q&A – Ask the Experts! (27 Jul 2026)

Mon, 27 Jul 2026 22:30:00 GMT

Investor Panel Q&A – Ask the Experts!

Click here to pre-register!

Have questions about real estate investing? Want practical advice from seasoned investors on finding deals, financing, and growing your portfolio?

Join us at WiscoREIA Milwaukee for an Investor Panel Q&A, where experienced local investors will answer your questions live. This is your chance to get insider tips, real-world strategies, and actionable guidance straight from the pros.

Topics may include:

✅ Sourcing off-market deals

✅ Creative financing options

✅ Scaling rental portfolios

✅ Marketing, rehabbing, and flipping strategies

✅ Navigating challenges in today’s market

Bring your questions, your scenarios, and your curiosity—this interactive session is all about giving you clarity, confidence, and tools you can use in your investing journey.

Whether you’re just starting out or looking to scale, this is the place to get answers that matter.

Panelists: TBA

WiscoREIA’s Milwaukee Meeting Always Meets on the 4th Monday of the Month from

5:30 pm - 8:15 pm!

Host: Chris Hake

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!

Meeting Location:

Homewood Suites by Hilton

11320 W Burleigh St

Wauwatosa, WI 53222

Please enjoy food, drinks, and Tip Your Servers!

5:30 pm - 6:00 pm - Doors open early for Networking

6:00 pm - 8:15 pm - Speaker Presentation

The meeting ends at 8:!5 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***

Click here to pre-register!