WiscoREIA upcoming events

WiscoREIA Wausau: Back-to-Back Real Estate Case Studies (21 Sep 2026)

Mon, 21 Sep 2026 23:00:00 GMT

Back-to-Back Real Estate Case Studies

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.

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 Wausau: Real Estate Nightmares & Horror Stories (19 Oct 2026)

Mon, 19 Oct 2026 23:00:00 GMT

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.

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 Wausau: STR Guest Experience Masterclass: Turn Every Stay into a 5-Star Story (16 Nov 2026)

Tue, 17 Nov 2026 00:00:00 GMT

STR Guest Experience Masterclass:

Turn Every Stay into a 5-Star Story

Click here to pre-register!

Want to stand out in a saturated short-term rental market?

It’s not just about the property, it’s about the experience.

Join seasoned STR investor Ashley Lang (29 units and counting) for a no-fluff, real-talk presentation on delivering 5-star guest experiences that actually grow your business.

We’re talking:

✔️ How to create wow-factor moments without blowing your budget

✔️ Messaging strategies that prevent problems before they start

✔️ Handling guest drama like a pro (yes, even those guests)

✔️ Systems that make 5-star reviews the norm

✔️ The secret to turning one-time guests into loyal repeat bookers

✔️ How scale your STR portfolio

Whether you’re managing your first unit or scaling a portfolio, this session will give you tangible tools to elevate your guest experience, and your bottom line.

Speaker: Ashley Lang

Ashley Lang is a powerhouse real estate investor, short-term rental expert, and the founder of Clear Trail Properties. Since entering the short-term rental space in 2018, Ashley has built and scaled a high-performing STR portfolio rooted in one core belief: great design and great systems create great returns.

She currently owns and operates 25+ short-term rental units across Arizona, Central Wisconsin, Northern Wisconsin, and Michigan’s Upper Peninsula, while also scaling a rapidly growing co-hosting company managing an additional 20+ units across the same markets. In addition, Ashley oversees 25+ long-term rentals and flips single-family homes alongside her partner, Buck.

Ashley is known for her obsession with intentional STR design—from floor plans and furniture layouts to guest flow, durability, and the smallest finishing details. She believes design is not decoration; it’s a strategic tool that directly impacts occupancy, ADR, guest experience, and long-term asset performance. Her approach blends creativity with operational efficiency, ensuring properties are not only beautiful, but profitable and scalable.

Beyond building her own real estate empire, Ashley is passionate about teaching and coaching other investors to shorten their learning curve, avoid costly mistakes, and create freedom through real estate-backed businesses. Her work empowers others to confidently turn a vision into a high-performing short-term rental operation.

When she’s not running her companies, Ashley enjoys mountain biking, hiking, camping, and traveling with her boyfriend Buck, their son Korbin, and their four beloved bulldogs.

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.

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!