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  • WiscoREIA Sheboygan: My Short-Term Rental Story

WiscoREIA Sheboygan: My Short-Term Rental Story

  • 26 Jun 2024
  • 6:30 PM - 9:00 PM
  • Legand Larry's

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My Short-Term Rental Story


Join us for an engaging session devoid of fancy slides and fluff, where we'll share our story of transforming from zero rentals to collecting well over $1 million in rents in just over two years. This isn't a lecture; it's a conversation. Bring your questions, and let's dive into the practical strategies and real-life experiences that propelled our success. Whether you're a seasoned investor or just starting, this session will inspire and inform, leaving you ready to take your real estate journey to new heights.  


Speaker: Jeremy Udovich


Born and raised in Sheboygan, Jeremy is a dedicated family man and professional with a rich background. As a married father of three pre-teen boys, he cherishes family time and values the importance of a strong, supportive home environment. Jeremy brings a wealth of experience to his role in the technology industry, where he works full-time in sales. His commitment to excellence extends beyond his career, as he actively serves on multiple boards, leveraging his expertise to make a positive impact in various spheres. Prior to his current endeavors, Jeremy spent a decade in the golf and hospitality industry, honing his skills and cultivating a deep appreciation for customer service and business development. With a passion for personal and professional growth, Jeremy embraces new challenges and opportunities, always striving to make a difference in the lives of others.


WiscoREIA’s Sheboygan Meeting Always Meets on the 4th Wednesday of the Month from 6:30 pm to 9:00 pm!


Hosts: Geoff Possley and Chris Wolfert

Geoff is a part time buy and hold investor with investments in the Fox Valley and Sheboygan area. He is a full-time aircraft certification engineer for Gulfstream Aerospace in Appleton where he lives with his wife Laura and four children Carter, Madeline, Rowen and Brielle.

Geoff got started in real estate in 2005, with very little REI knowledge, when he purchased a single-family home with the plan to do a live-in flip over the next few years. After the bubble burst in 2008 his focus shifted from turning a profit to simply breaking even. This led Geoff to step away from real estate for a number of years until he discovered WiscoREIA in 2018 where he finally was able to acquire the knowledge and network that was necessary to be successful in real estate investing.  His goal is to use REI as a means to retire early from engineering.

Geoff currently invests in single-family and small multi-family properties that he operates as traditional rentals as well as short term furnished rentals. In his free time Geoff enjoys camping with his family, playing golf, snowboarding, hunting, and good beer.

Chris is a buy-and-hold real estate investor who got started in real estate investing out of necessity. In 2008, he bought a small condo in Chicago and shortly after, his family quickly began to outgrow the space with the arrival of their first child. When he went to sell the property in 2011, he realized he would take a sizable loss. Therefore, he decided to turn the condo into a rental property instead. Despite his initial apprehension, he quickly saw the advantage of real estate investing.

In 2018, Chris began actively investing in real estate after moving to Sheboygan, WI. He invests in single-family homes and duplexes, which he operates as both traditional rentals and short-term furnished rentals. His long-term goal is to expand into larger multi-family complexes. Chris’s investing greatly increased after partnering with a good friend who introduced him to WiscoREIA.

In his free time, Chris enjoys spending time with his wife Marla and their three children, Finn, Lexi, and Fiona. He is an active coach for youth soccer and basketball, spending much of his time during the fall and spring coaching soccer and during the winter coaching basketball. In addition to coaching, he enjoys snowboarding, cycling, golfing, and craft beer.


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


Meeting Location:

Legend Larry's

1142 Plankview Green Blvd

Sheboygan Falls, WI 53085

Please enjoy food, drinks, and TIP YOUR SERVERS!


6:00 pm - 7:00 pm - Doors open early for Networking

7:00 pm - 9:00 pm - Speaker Presentation


You can stay after the meeting as well to network! Remember to bring your deals!

Members are always FREE! Your first meeting with WiscoREIA is FREE!

 After your first meeting, Non-Members are $20.00.

***Make sure to pre-register - We are now Cashless***

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