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Navigating Real Estate: Jon Singleton’s Approach to Success

Kyle Madorin August 4, 2025

The road to real estate success isn’t always a smooth one. There are twists, turns, and moments where the path ahead looks unclear. But with the right strategies and approach, you can overcome the challenges and thrive. This is exactly what Jon Singleton has done in his career, and I had the privilege of sitting down with him on my podcast to discuss how.

Jon is the founding partner of Singleton & Hopkins at Watson Realty, a highly successful real estate team in Northeast Florida. Jon shared his journey and the power of leadership, community involvement, and smart strategies.

In this post, I’ll walk you through some of the most valuable insights Jon shared with me.

Jon’s Insights Into Achieving Real Estate Success

Through his unique background and unwavering focus on community, Jon was able to rise to the top of his field. Here’s how he did it.

Getting Into Real Estate

Before entering the world of homes and sales, Jon spent 10 years in the Navy. As a helicopter pilot, he learned leadership skills that would serve him well in real estate. The military taught him discipline, focus, and a strong work ethic.

However, it wasn’t just the technical skills that set him up for success. Jon’s background in psychology and emotional intelligence gave him an edge when connecting with clients. He understands that real estate is, at its core, a people business. Being able to read emotions and understand people’s motivations has helped him build trust and form lasting relationships with his clients.

Whether negotiating a deal or simply listening to concerns, Jon’s ability to connect on a human level has played a huge role in his success.

Adapting to Real Estate’s Changing Landscape

Jon has seen firsthand how the real estate industry can change from one crisis to the next.

He began his career in the mid-2000s, during a period of rapid growth. But the 2008 housing crash made Jon and many others in the industry pivot. In the years that followed, he found himself navigating the complexities of short sales and foreclosures.

Fast forward to the pandemic, and once again, the market shifted. Agents, including Jon, had to adapt quickly to virtual tours, 3D walkthroughs, and new ways of conducting business.

Jon highlighted a significant shift that’s occurred in recent years: changes in how buyers and their agents are compensated. Where buyers used to expect agents to simply open doors, now the entire role of the buyer’s agent is much more transparent.

The lines between buyer and listing agent roles have blurred, and communication about fees and services is more important than ever. For Jon, this change has been a chance to demonstrate his value and help clients understand exactly what they’re getting for their investments.

The Power of Community Involvement in Real Estate

Whether it’s serving on the historic preservation board or coaching in the Boy Scouts, Jon has made it a point to build relationships outside of real estate. These personal connections have turned into a strong network, providing him with steady business and referrals over the years.

Jon emphasizes that the trust you build with people in your community can be far more valuable than any lead generation tool. He’s earned the trust of countless families, and that trust has led to business time and time again.

He believes that when you show up for people in meaningful ways, they’re more likely to trust you when it comes time to make a big decision, like buying or selling a home.

Open Houses and Social Media: Key Tools for Client Engagement

Jon has taken a more strategic approach to open houses, adjusting his timing to meet the needs of today’s buyers. No longer waiting until the property has been on the market for weeks, he holds these events as early as week one. This gives potential buyers a chance to see properties in person before making decisions and allows Jon to engage directly with them in a more informal, yet professional, setting.

Social media is another tool Jon uses effectively. He believes in posting frequently, but without overcomplicating it. By sharing a mix of professional and personal content, Jon has been able to stay visible without getting consumed by it.

For me, realtors and agents should also leverage a real estate podcast network. By doing so, you can reach new clients and elevate your brand presence.

Owning Your Business Funnel: A Sustainable Path to Success

Jon’s philosophy on lead generation is simple: own your business funnel.

While platforms, like Zillow, can provide leads, Jon knows that relying on them means you’re renting your business funnel.

He believes that by building trust and relationships within the community, you can create a more sustainable, self-sufficient pipeline of leads. This takes time, but Jon has proven that it’s well worth the effort.

Unlike rented funnels, this one won’t change based on an algorithm. The more you nurture your reputation and network, the more stable your business becomes.

Want to hear my entire conversation with Jon? Listen to the podcast episode! 

Follow Real Estate on the Up for More Insightful Conversations with Industry Icons!

Jon’s approach to real estate, combining leadership, community involvement, and adaptability, plays a huge role in his ongoing success. His insights serve as a great reminder that this line of business is more than just transactions. It’s about people, relationships, and making smart, strategic choices.

If you want to hear more from experts like Jon, tune in to Real Estate on the Up. We’re bringing you conversations with industry icons who share their knowledge and experiences to help you succeed in the real estate world.

And, if you’re looking to buy a home in Florida, reach out to Upwell Realty. Our team is here to help you every step of the way, offering expert guidance and top-notch service. Contact us, and let’s make your real estate goals a reality!

 

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