Thinking about leaving your 9-to-5 job? You’re not alone.
A lot of people dream about being their own boss, earning more money, and having more control over their time. That’s exactly what Matthew Simmons did. He walked away from his CEO job and jumped into wholesale real estate—a smart way to earn big profits without needing to buy or fix houses.
In his very first deal, Matthew made $18,000—without even owning the property. This blog shares how he did it, why probate real estate is such a great opportunity, and how you can follow in his footsteps with simple steps and a strong mindset.
From CEO to Real Estate Wholesaler
Before getting into real estate, Matthew was the CEO of several companies. He owned a gym, a vending machine business, and a bathroom remodeling service. All were profitable, but he was ready for something new—something with more freedom and higher returns. That’s when he discovered real estate investing.
Wholesaling is when you find a property, get it under contract at a low price, and sell that contract to another buyer—usually an investor. You don’t need to fix the property or even buy it yourself. You just need to connect sellers and buyers. And that’s exactly what Matthew did.
How Matthew Made $18K from His First Wholesale Deal
Matthew's first deal was a probate property. Probate real estate investing involves buying homes from families who inherited them after a loved one passed away. These homes are often sold quickly, which creates great opportunities for real estate investors.
Door Knocking vs. Direct Mail
Matthew started by getting a list of probate leads. He tried direct mail marketing first—sending postcards to property owners—but didn’t get much response. Instead of giving up, he went out and started door knocking. This personal touch made a big difference.
One family was willing to sell their inherited home. It was in a rough area, but the house was in good shape. Matthew ran the numbers using a simple wholesaling formula:
After-Repair Value (ARV) - Repair Costs - Investor Profit = Max Offer.
In this case, the ARV was around $40,000. He offered $11,000. It felt risky—he didn’t want to offend the sellers—but he was honest and explained his process. The family agreed.
Matthew didn’t even have a buyer’s list yet. So he went to a local real estate investment group and pitched the deal. He found a landlord who bought the property for $29,000. That’s an $18,000 profit—on his very first deal.
Why Probate Real Estate Deals Work
Matthew focused on probate real estate because it has a high return on investment and less competition. Many families don’t want to hold onto inherited homes, especially if they live far away or the home needs repairs. That makes them motivated sellers—exactly what wholesalers look for.
In places like Allegheny County, where the population is older, there are more probate cases. This creates a steady stream of off-market deals that other investors might not even know about.
Wholesaling Formula: Step-by-Step Guide
Wholesaling step by step means learning how to make smart offers. Matthew uses a simple system:
- Find the ARV (what the home will sell for after repairs)
- Estimate repair costs
- Subtract the profit your buyer will want
- Make an offer that still leaves room for your own fee
Example Deal Breakdown
If a home’s ARV is $100,000 and it needs $20,000 in repairs, a flipper might want to buy it for $60,000. That gives them room to make a profit after fixing and selling.
If you lock the home up at $50,000, you can wholesale the deal for $60,000—and keep the $10,000 difference.
In Matthew’s case, his buyer was a landlord. They weren’t looking to flip but to rent. That’s why understanding what different buyers want—cash flow or resale profit—is so important in wholesaling.
Mindset and Discipline: Keys to Success in Wholesaling
So, how did Matthew make the leap from business owner to wholesaling success? It wasn’t just luck. His background helped. Running a gym taught him about recurring revenue.
The vending business taught him how to build systems. These experiences gave him the mindset and discipline to succeed in wholesaling.
Helping Others Get Started in Real Estate
Matthew’s journey doesn’t stop with making money. He’s now working with a group of over 40 new investors, teaching them how to wholesale, build a buyers list, and find motivated seller leads. He’s focused on helping others create real freedom through real estate.
Final Thoughts
Matthew’s story shows that you don’t need to be a real estate expert or have a ton of money to get started. You just need to learn the basics of wholesaling, stay consistent, and take action—even if it means knocking on doors.
By focusing on motivated sellers, building a buyers list, and using a smart offer strategy, Matthew went from working long hours as a CEO to running his own business with more freedom and higher profits.
If you’re ready to take control of your future, wholesaling might be the first step. Your path to financial freedom might start with just one deal.
About Benjy Nichols
Benjy has been a media specialist at DealMachine for the last 2.5 years. He produces, writes, shoots, and edits our media content for our member's DealMachine and Real Estate education.