Through the hardest seasons of life, I’ve learned to lean into faith, trust that steady effort leads somewhere meaningful, and keep showing up to serve others well.
It was the most challenging real estate market in thirty years, and I was just starting to build my business. I got my first deal early on when a friend gave me a shot at listing his house, and it sold in two days with multiple offers. It felt like confirmation that I had made the right choice. But then everything went quiet. By the spring of my first year, I had gone months without another deal. During that time, my wife was laid off. With a young daughter to provide for, the pressure was intense. I started to seriously question whether I needed to return to corporate life just to stay afloat.
For as long as I can remember, my goal was to help people. Most of my family works in medicine, so it was always a goal of mine to ensure whatever I did for a living, I was making a tangible difference. For over a decade, I worked in consulting and tech. My role was often as a middle person between teams. At one point I was titled “Solution Engineer” because I was the person who connected the dots, translating client needs, and pushing projects forward. I liked the challenge and the pace, but even with success in that role, I knew I wanted something more.
Over the years, friends who knew me well started recommending real estate. I brushed it off at first. I liked the security of a stable paycheck, and real estate seemed uncertain. But as my wife and I started buying and building properties, I got more involved. I enjoyed understanding the market and thinking creatively about how to add value to a home. I originally got my license just to manage our own deals, thinking we would expand our portfolio. But after being laid off in 2023, I took the leap and went all in.
The months that followed my first deal were some of the hardest I have experienced. Deals fell through. Leads dried up. I felt like I was doing everything I could and getting nothing in return. It tested me in ways I did not expect.
That stretch forced me to rely on something deeper. For the first time, I had to trust that if I showed up each day with the right intent, provision would follow. I joined a faith and work program and was paired with a mentor, Michael, who reminded me to lead with purpose. He helped me refocus, not just on what I was doing, but why. I also joined a new team to build structure and leaned into really connecting with my network. Slowly, things started to shift.

After months of doubt, I reached a turning point. By the end of the year, I had closed just over $7 million in sales—my goal was $5 million, so it was a huge achievement! Most of it came from relationships and referrals. It was not easy, but it was proof that I could do this. That I could build a successful business that had a real impact. When you lead with a mission to serve, the rest follows. Real estate has given me a platform to serve people well, provide for my family, and build something lasting.
None of this would have been possible without my wife, Kristin. She walked with me through every uncertainty and even connected me with people in real estate that moved things forward. Our daughter, Harper Mave, is a daily reminder of what we are working toward. Real estate has given me the flexibility to be present for my family, to grow a business rooted in service, and to create something I can one day pass on.
Today, I’m still a “Solution Engineer” for my clients in real estate. Whether buying, selling, or investing, there are bound to be challenges, and my job is to help my clients navigate the processes seamlessly. Real estate has a lot of moving pieces, but with my professional background, I excel at keeping things organized, making sure clients always know what’s happening, and ensuring everything moves forward.
I’ve built homes, flipped properties, and managed short-term rentals, so I understand real estate from the inside out. That hands-on experience means I know what adds value, how to prevent unnecessary pitfalls, and how to educate clients so they can make confident decisions. I also have a strong network of trusted contractors, vendors, and service professionals, and I make it a priority to connect my clients with the right people. My goal is to be the person you can call for anything real estate-related during the transaction and long after!
Sincerely,
John Underwood
REALTOR® | LIC#811076
Primary 512.270.7323
Office 512.575.3644
john.underwood@compass.com
johnunderwoodaustin.com