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

  • When
    17 Aug 2026
  •  
    6:00 PM - 8:30 PM
  • Location
    The Bar | 10302 Market Street Rothschild, WI 54474

  Register

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

  Click here to pre-register!

  
  

  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!

  Show details
• WiscoREIA Wausau: Back-to-Back Real Estate Case Studies

  • When
    21 Sep 2026
  •  
    6:00 PM - 8:30 PM
  • Location
    The Bar | 10302 Market Street Rothschild, WI 54474

  Register

  Back-to-Back Real Estate Case Studies

  Click here to pre-register!

  
  

  Two investors. Two real deals. One night packed with real-world lessons.

  
  

  Join us in Wausau for a special back-to-back Case Study night featuring Jake Strassburger and Jeremy Dobson, as they take you behind the scenes of deals they’ve actually worked through—including the challenges, financing strategies, unexpected obstacles, and lessons learned along the way.

  
  

  ️Powering Up with a Portfolio Deal

  Presented by Jake Strassburger

  
  

  Jake will break down a multi-property deal and share how he combined creative and traditional bank financing to make the deal work. We’ll cover deal structure, analyzing multiple properties, due diligence, and the importance of not giving up when challenges arise.

  
  

  Old House, New Lessons
  Presented by Jeremy Dobson

  
  

  Jeremy will walk through the transformation of a heavily distressed property, sharing lessons on risk, renovation, financing, contractors, cost control, and maximizing value—while also building a real estate business that supports family life rather than consuming it.

  
  

  Come hear the real stories behind the deals, learn from the challenges, and take away practical strategies you can apply to your own investing journey.

  
  

  Don’t miss this unique night of real deals, real challenges, and real lessons!

  
  

  Case Study Presenters

  Jake Strassburger and Jeremy Dobson

  
  

  

  Jake Strassburger

  
  

  About 2.5 years ago, I made the decision to leave my W-2 career and pursue real estate full-time, fully committing myself to building something of my own. Since making that transition, my experience and portfolio have grown rapidly, expanding from 12 doors to 60. Rather than learning from the sidelines, I’ve focused on learning by doing—acquiring, improving, renovating, and managing properties firsthand.

  
  

  A major part of that journey has been staying closely involved in the physical side of real estate, particularly construction and property improvements. I’ve developed a strong understanding of renovations, repairs, construction processes, and the factors that truly drive value in a property. Instead of outsourcing every aspect of the work, I intentionally stayed close to the process so I could understand the real costs, timelines, quality, and challenges involved in executing a project successfully.

  
  

  That hands-on experience has shaped the way I approach real estate today. It has allowed me to become more confident in identifying opportunities, evaluating properties, managing improvements, and making informed investment decisions based on real-world experience rather than theory.

  
  

  Real estate remains the core focus of what I do, with my general contracting business serving as a complementary part of that larger vision. As my portfolio continues to grow, I’m transitioning away from being as involved in the day-to-day hands-on construction work and focusing more heavily on management, strategy, and long-term portfolio growth.

  
  

  My goal is to continue building a strong, sustainable real estate portfolio grounded in practical experience, disciplined decision-making, and long-term ownership.

  
  

  

  Jeremy Dobson

  
  

  Jeremy Dobson is a real estate investor and co-owner of Visionary Home Ventures, LLC, a family-owned real estate business serving Central Wisconsin. Together with his wife, Lea, he invests in distressed properties, residential renovations, rental housing, and other real estate opportunities.

  
  

  Jeremy and Lea are raising a blended family with three children and two dogs. Faith and family are central to how they structure their lives and business. Jeremy believes real estate does not have to become an all-consuming grind—it can be intentionally designed around the life, priorities, and future a person envisions.

  
  

  Jeremy entered real estate while continuing his longtime career as a CNC machinist. His approach centers on buying carefully, solving difficult problems, building strong relationships, and using systems, delegation, and accountability to protect what matters most. He is especially interested in the mindset and personal growth that come from taking calculated risks and working through challenging projects.

  
  

  Outside of real estate, Jeremy enjoys spending time outdoors, riding ATVs, fishing, upland bird hunting, and traveling with his family. He is involved with Wausau Evening Toastmasters and also values volunteer work, charitable giving, and supporting organizations and causes within his community.

  
  

  In this presentation, Jeremy shares an honest look at one of his most challenging renovation projects, including the mistakes, unexpected expenses, mindset shifts, and practical lessons that helped him grow as both an investor and a business owner.

  Let me know if you need anything else,

  
  

  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!

  Show details
• WiscoREIA Wausau: Real Estate Nightmares & Horror Stories

  • When
    19 Oct 2026
  •  
    6:00 PM - 8:30 PM
  • Location
    The Bar | 10302 Market Street Rothschild, WI 54474

  Register

  Real Estate Nightmares & Horror Stories
  

  Click here to pre-register!

  
  

  Every Investor Has a Deal That Still Haunts Them…

  
  

  Maybe it was the contractor who vanished without a trace.
  

  Maybe the “perfect” property that uncovered one expensive surprise after another.

  Maybe the tenant situation that turned into a full-blown nightmare.

  
  

  Or maybe it was the deal that looked like a home run… until it wasn’t.

  This October, WiscoREIA Wausau is bringing those stories to life with a Halloween-themed night of Real Estate Horror Stories!

  
  

  We’re opening the floor and inviting investors to share their real-life experiences — the bad deals, costly mistakes, unexpected disasters, difficult tenants, contractor nightmares, and lessons learned the hard way.

  
  

  And you’re not just coming to listen. Audience participation is encouraged! Share your own story, learn from someone else’s mistake, and hear the lessons behind the deals that didn’t go according to plan.

  
  

  Whether you’re a seasoned investor or just starting out, you’ll leave with:
  

  Real-world lessons
  Mistakes to avoid
  Stories you won’t forget
  A few laughs and great networking
  And maybe some reassurance that even experienced investors have a deal that haunts them!

  
  

  Come dressed for Halloween, bring your worst real estate horror story, and get ready for a meeting that’s equal parts education, networking, and entertainment.

  Because in real estate, sometimes the scariest deals make the best stories — and the best lessons.

  
  

  Join us this October at WiscoREIA Wausau for a night of Real Estate Horror Stories!

  
  

  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!

  Show details