Rookie Investor Panel – Real Stories, Real Lessons
Every expert started as a rookie—and this panel proves it! Join us as local investors share their real-life journeys, from their very first deals to the lessons they’ll never forget.
Whether you’re brand new or looking for fresh inspiration, you’ll walk away with:
✨ Honest insights on wins AND mistakes
✨ Strategies that worked (and a few that didn’t)
✨ Motivation to keep pushing through the challenges
This is your chance to learn from people who were in your shoes not long ago. No fluff, no theory—just real stories from real investors.
Don’t miss this one—come ready with your questions and leave with practical takeaways you can use right away!
Panelists
Matt Richardson and Ashley Phillips - At the age of 25 Matt and Ashley decided to skip the “normal” path of homeownership and jump straight into house hacking as a way to financial freedom. Their journey started when they bought their first multifamily property in the Milwaukee area and moved into one of the units and had tenants help pay the mortgage. That first leap showed them the power of living strategically and they have been hooked ever since. Now, they are on their second house hack and first flip in the Green Bay area after Ashley decided to start working for Wisconsin Discount Properties. They are cashing flow on their Milwaukee property and have built equity. Their goal is to continue growing a portfolio that not only supports their lifestyle, but also gives them more time together, more freedom to travel, and more opportunities to invest in their community.
Sean Gibbons - Sean jumped headfirst into full time real estate investing toward the end of 2024. His W2 days consisted of working as a product safety inspector and corporate security analyst. Since going full time he's completed 6 flip projects and has navigated some pretty treacherous waters as he gets his business off the ground. He's also a partner owner of Genesis Impact Sports in Appleton. He's a fulltime Jesus person and serves on the guardian team at his church. He lives in Appleton with his wife, Lindsey, great dane, Thor and two cats, Ace and Bandit.
Connor Derenne - My name is Connor Derenne, I have been working at Wisconsin Discount Properties for a year and a half, working in the dispositions department. We specialize in sourcing off-market investment properties for real estate investors across Wisconsin. I purchased my first duplex in April 2025 and am currently house hacking as I work toward building a rental portfolio and eventually taking on some flip projects as well.
Jared Boerst - I grew up helping my dad build custom homes in NE Wisconsin and on Shawano Lake. Learning these skills has come in handy as I have been able to do all of the work necessary on my flips and rentals. I started my real estate portfolio in 2022 and have completed 4 full flips, and cure 3 doors rented. My current project is doing a full remodel on my primary house. I work full time job as an engineer, and am married to the best woman in the world! My wife and I plan to continue to grow our real estate portfolio to include more doors and bigger properties in the near future and appreciate the connections made in the REIA community!
WiscoREIA’s Green Bay Meeting Always Meets on the 1st Tuesday of the Month from 7:00 pm - 9:00 pm!
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 Lyric Room at Stage 1
231 N Broadway
Green Bay, WI 54303
Please enjoy food, drinks, and TIP YOUR SERVERS!
6:30 pm - 7:00 pm - Doors open early for Networking
7:00 pm - 9:00 pm - Speaker Presentation
The meeting ends at 9:00 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!
Members are always FREE! Your first meeting with WiscoREIA is FREE!
After your first meeting, Non-Members are $30.00.
***Make sure to pre-register - We are now Cashless***
Hosts: Joe Gracyalny & Jennifer "Jennie" Buah
You may also like the following events from WiscoREIA:
Also check out other
Meetups in Green Bay,
Sports events in Green Bay.
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