WiscoREIA Hudson: How I'd Make $1 Million in 2 Years if I Had to Start Over

How I'd Make $1 Million in 2 Years

if I Had to Start Over

What if you woke up tomorrow and everything was gone, your money, your deals, your entire financial foundation?

No cash. No properties. No deals in progress.

Just your knowledge, a phone, a car, and six months of runway to cover basic expenses.

Could you rebuild to $1 million in two years?

We challenged five experienced, battle-tested investors in our community with this exact scenario, and every one of them said, “Absolutely.”

For one powerful night, these proven investors will pull back the curtain and share the real-world strategies they’d use to rebuild from zero in today’s unpredictable market, including:

• The first strategic moves they’d make

• The surprisingly simple actions that create the fastest momentum

• How they’d generate income with or without capital

• The traps, dead ends, and timewasters they’d avoid at all costs

This is not theory. It’s a behind-the-scenes look at how real investors think, act, and execute when everything is on the line.

If you want to know how a true investor would rebuild from nothing, this is the meeting you don’t want to miss.

Panelists:

Ryan Gray

Ryan began in real estate and business in 2017. He owns Stable Living LLP, which has 19 licensed Adult Family Homes and does in-home care for over 80 clients. This business employs over 100 staff.

Ryan has grown a portfolio of rentals that has 750 doors currently. The majority of the acquisitions have been done using creative financing with little money down. His focus is on structuring deals with creative finance and finding deals offmarket. He also owns storage units, 2 laundromats, a farm, and a trailer park.

His wife Eva Gray is a CPA who focuses on tax planning, mastering business plans, and self-managing the properties. He also started a flipping and wholesaling business called 715 Home Buyers with Brandon Anderson, which does over 30 transactions a year.

Ryan also has two children, Josephine and Drew. They love to go camping together in the summer and vacationing in the winter. In his free time, he also likes to play baseball, deer hunt, and ride motorcycles.

Randy Zimmerman

For more than thirty years, Randall Zimmermann has built and led technology companies focused on solving meaningful problems. Most of his career has been in healthcare and behavioral health technology, where he founded, grew, and led software companies that helped providers improve the way they serve patients. Along the way, he has led organizations through startup growth, product innovation, and a successful acquisition.

Today Randall is an entrepreneur, investor, and advisor who enjoys helping founders and leadership teams turn good ideas into successful businesses. He is particularly interested in how artificial intelligence can become a practical tool for organizations and individuals. While he does not consider himself an AI expert, he is actively building products, learning alongside experienced practitioners, and exploring thoughtful ways AI can create real value.

Randall is known for connecting vision with execution, building strong teams, and creating products that make a positive difference. Whether working with entrepreneurs, executives, or nonprofit leaders, he enjoys conversations about innovation, leadership, technology, and the opportunities that emerge when experienced business leaders embrace new ideas with humility and curiosity.

Corey Wright

Corey Wright is not your typical real estate investor.

He started with nothing — bankruptcy, arrests, and seven foreclosures. Today he has completed 250 plus residential flips, built and sold the largest minority owned RE/MAX franchise in the Twin Cities, and was named 2025 Investor of the Year. He is the founder of Legacy Wealth Group, a 500 member real estate investment community built on one belief — that real wealth is built in the real world, not in a classroom.

Corey does not just teach real estate. He puts people in it. His coaching clients are closing deals, stacking profits, and scaling in their first year. His Legacy Builders internship program is developing the next generation of investors from the ground up. And his hard money lending arm Legacy Capital is funding the deals his community is doing right now.

He is building the Legacy Center — a 70,000 square foot headquarters for investors, entrepreneurs, and the next generation of wealth builders in the Twin Cities.

Corey Wright is proof that the right room, the right mentor, and the right system can change everything.

WiscoREIA’s Hudson Meeting Always Meets on the 4th Tuesday of the month from 5:30 pm - 8:30 pm!

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

Location

Max's Social House (Formally Ziggy's)

310 2nd St,

Hudson, WI 54016

Please enjoy drinks, and TIP YOUR SERVERS!

5:30 pm - 6:00 pm - Doors open early for Networking

6:00 pm - 8:30 pm - Speaker Presentation

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***

Hosts: Alyssa Burton & Lisa Mielke