WiscoREIA Wausau: Real Estate Against the Grain: Saying "Yes" to Opportunity & Figuring It Out in the Trenches (17 Aug 2026)

Mon, 17 Aug 2026 23:00:00 GMT

Real Estate Against the Grain: Saying "Yes" to Opportunity & Figuring It Out in the Trenches

What if the biggest difference between successful investors and everyone else isn't experience—it's simply the willingness to take action?

Join Chris and Brooke for an honest, no-fluff session about what it really takes to build a successful real estate investing business. Instead of waiting for the "perfect" deal, the "perfect" market, or the "perfect" plan, they chose to say YES to opportunities and figured things out along the way.

That mindset helped them build a massive real estate portfolio in just three short years—not because they followed a flawless blueprint, but because they were willing to learn, adapt, and keep moving forward.

In this refreshing presentation, Chris and Brooke will challenge many of the common myths surrounding real estate investing and share the lessons they've learned from building their business in the trenches. You'll discover why there is no one-size-fits-all formula for success and why taking consistent action often beats waiting for perfect conditions.

Whether you're just getting started or you're looking to break through to the next level, you'll leave with a new perspective on overcoming fear, embracing uncertainty, and creating opportunities instead of waiting for them.

If you've ever felt stuck waiting for the "right time" to invest, this is a session you won't want to miss.

Speakers: Chris Draper and Brooke Baenen

Chris Draper is the owner of CW Custom Exteriors, a premier residential and commercial exterior remodeling firm specializing in roofing, siding, and full-scale renovations. Known for his unwavering integrity and meticulous attention to detail, Chris has built a reputation for consistently exceeding client expectations. Over the last several years, he has channeled that same work ethic into building an impressive rental portfolio and executing successful flips across Northeast and Central Wisconsin.

Brooke Baenen brings 18 years of housing industry expertise to the table. After a decade managing a prestigious homebuilding firm, she transitioned into a full-time Realtor in 2018, dedicating her practice to helping investors build and scale their portfolios. When Brooke and Chris crossed paths, their professional strengths aligned perfectly, sparking Brooke's own real estate investing journey.

Together, they founded Daylight Ventures, LLC, blending Chris’s construction expertise with Brooke’s deep market knowledge. The powerhouse duo is currently managing their portfolio of 40 plus units, a new remodel in Weston and recently expanded their footprint into the Sunshine State with two new acquisitions in Clearwater, Florida. By scaling the proven strategies they mastered in the Midwest, they are rapidly building a diverse, multi-state portfolio.

And they are making the partnership official in more ways than one—Chris and Brooke are thrilled to be tying the knot this coming November!

WiscoREIA’s Wausau Meeting Always Meets on the 3rd Monday of the Month from

6:00 pm - 8:30pm!

Hosts: Derek Dombeck & Cayla Farley

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.

Cayla and Brandon are a dynamic husband-and-wife real estate investing team based in Wisconsin. As parents of two and long-term investors, they’ve built their business around transforming outdated single-family and multifamily properties into strong, sustainable assets designed for long-term growth.

Beyond real estate, they also own and operate a successful fence installation company, giving them a hands-on, operations-driven perspective that sets them apart. When they’re not managing projects or growing their portfolio, Cayla and Brandon love spending time outdoors, staying active, and making memories with their kids—proof that it’s possible to build a thriving business while prioritizing family and lifestyle.

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

Meeting Location:

The Bar

10302 Market Street

Rothschild, WI 54474

Please enjoy food, drinks, and TIP YOUR SERVERS!

**Time**

6:00 pm - Doors Open & Check-in

6:30 pm - Meeting Starts

7:00 pm - 8:30 pm - Speaker Presentation

The meeting ends at 8:30 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 upcoming events

WiscoREIA Wausau: Real Estate Against the Grain: Saying "Yes" to Opportunity & Figuring It Out in the Trenches (17 Aug 2026)