Today we’d like to introduce you to Jonathan Messri.
Jonathan, we appreciate you taking the time to share your story with us today. Where does your story begin?
We grew up watching our dad try his hand at buying and fixing up houses in different states than the one we grew up in. Most of the time, things didn’t always go smoothly for our parents and their real estate endeavors. Projects cost more than expected, partners backed out, tenants stopped paying rent, and my mom and dad carried the burden of some painfully bad real estate decisions. Those years of living in “work-in-progress” rental homes really left a mark on us, especially that unforgettable summer in Peoria, Arizona, when we were sweating it out in a half-finished duplex in 100-plus degree heat. Those experiences taught us early how tough real estate can be, but also how much potential there is when you stick with it and put the hard work in.
My sister and other half in business, Mallie, got her real estate license at 19 because she knew from a young age she wanted to be involved with real estate. Making our parents proud was a huge motivator for me as well. I originally set out to become a nurse, but about halfway through nursing school I had a change of heart when I realized my own path to helping people would look different. Around the end of 2017, during one fateful family dinner, we were talking about wanting different paths for ourselves, and that’s where the idea for Cash Out On My Home first began.
We never planned to have such a meaningful business that would allow us to help real people in tough situations every day, but we’re grateful for our position in the community. What started as a way to make a living turned into a mission for us, helping real people in really tough situations, and we’re thankful for the role we get to play in our community.
We attribute a lot of our success to building long-term relationships with locals who share the same heart for helping. This side of real estate, the side where we’re serving homeowners in distress rather than just listing homes traditionally, was new to us at first. But over time, and with the help of attorneys, title companies, and even folks at the tax and county offices, we learned quickly.
We’ve walked families through probate cases with heir lists longer than a Publix grocery line, and we’ve stood beside homeowners just days away from losing their house on the courthouse steps. The situations we’ve stepped into have rarely been simple, but being able to help people walk away with dignity and relief has been a true blessing. It’s in those tough moments that we’re reminded why we do what we do.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
It definitely hasn’t been a smooth road. Business is never a straight line to success. Starting anything from the ground up comes with challenges, but real estate specifically adds a whole other layer of complexity, a ride we’ve learned to enjoy.
When we started Cash Out On My Home, we had no idea that just a year later the pandemic would completely disrupt the way we worked. Our business has always been relationship-driven and built on meeting people where they’re at, physically and literally. For us, it’s about being in the room with someone, sitting at the kitchen table, walking through their home, and really listening to their story. Almost overnight, that became nearly impossible.
The market was uncertain, sellers were hesitant to do anything even for almost two years after, and there were moments we wondered if we’d even make it through. Those rough beginnings reminded us of our parents’ own rocky start, and we felt a responsibility to persevere, not just for ourselves but for them and for the community we wanted to serve.
Those early struggles taught us a lot. We learned patience, persistence, and the value of having strong local relationships to lean on. What really kept us going was the community itself. Even in the years when we had serious doubts, referrals kept coming in and people continued to trust us. Our commitment to each other and to the families we serve is what carried us through. That’s why we’re still here today, and why we’ll keep showing up for the people who need us most.
As you know, we’re big fans of Cash Out On My Home. For our readers who might not be as familiar what can you tell them about the brand?
We’re a family-owned business, and when we say family, we really mean it. On the surface, it might just look like Mallie and me, but often our mom, dad, and even our 14-year-old Chihuahua are along for the ride. At our core, we’re just a family helping other families. Having our parents back in the real estate picture makes it feel like we’re building more than just a business. We’re building a legacy, not just for ourselves but for others too.
In a way, every time we help someone through probate, foreclosure, or a home that feels too overwhelming to handle, we’re helping them protect their legacy too.
We’ve become known for taking on the messy situations most people run from. Most of the people we work with aren’t in a place where selling with a realtor makes sense. Life has thrown them an unexpected curveball, situations like foreclosure, probate, or tax issues, the kind of heavy circumstances no one ever plans for or wants to face. By stepping in and helping, we’re not only solving the immediate problem, we’re giving families a chance to close that chapter with dignity and protect what matters most.
Over the years, we’ve taken on people’s largest burdens, stepping in when they’ve completely given up and often becoming their last hope. Title nightmares? We’ve untangled them. Probate cases with multiple heirs who couldn’t agree? We’ve stepped in as the intermediary and made what felt impossible, possible. We’ve negotiated payoffs, sorted out interest rights, and even gone as far as visiting someone in jail just to get a document signed so a seller could finally move forward.
These aren’t the kinds of sales your average realtor is equipped to handle, and that’s exactly why people call us. To us, they’re never just houses. They’re burdens weighing someone down, and solving that is what we do best.
The moments that stick with us the most have nothing to do with contracts or closing dates, it’s the people. We’ve sat at kitchen tables and cried with families who felt like they had no way out. We’ve prayed together when the weight of the situation felt too heavy to carry alone. We’ve laughed and shared stories with folks who started out as clients but left as friends.
Every time someone walks away from the closing table with relief written all over their face, we’re reminded why we do this work. Our brand has always been about going the extra mile when others won’t. We’re not just another “we buy houses” company. For us, it’s never only about buying fast or for cash, it’s about walking with people through overwhelming chapters and helping them move forward with dignity and peace of mind.
If your selling situation feels unconventional, we want you to know you can call us without pressure or obligation. Even if we’re not the right fit, we’ll give honest advice and point you toward the best option for your family. At the end of the day, our heart is in serving this community, and that’s something we’ll never waver on. If you give us a call, we just may be the right fit to help you find peace of mind.
Is there something surprising that you feel even people who know you might not know about?
People are usually surprised by how far we’ll go to help someone get through a tough home situation. Most folks don’t expect a home-buying company to roll up their sleeves like that, but that’s what we’re known for. At the end of the day, we’re not afraid of the messy or complicated situations. In fact, that’s where we do our best work.
What also surprises people most is that the relationship doesn’t stop at the closing table. We don’t just show up, write a check, and leave. The truth is, many of those people don’t stay “clients” for long, they become friends. We’ve kept in touch with families years after a sale, swapped holiday cards, grabbed dinner together, and even invited them to family BBQs.
For us, it’s never just about buying a house. It’s about being there for people when life is overwhelming and building relationships that last long after the papers are signed.
Contact Info:
- Website: https://cashoutonmyhome.com/
- Instagram: https://www.instagram.com/cashoutonmyhome/
- Facebook: https://www.facebook.com/CashOutOnMyHome
- LinkedIn: https://www.linkedin.com/company/cash-out-on-my-home-chattanooga
- Twitter: https://x.com/cashoutonmyhome
- Youtube: https://www.youtube.com/@sellmyhousefastchattanooga
- Yelp: https://www.yelp.com/biz/cash-out-on-my-home-chattanooga
Image Credits
Cash Out On My Home
