Leadership

Jason H. Cryer: From Hard Lessons to High Impact—How One Leader is Changing the Way Real Estate Agents Are Trained and Treated

He never forgot how it felt to be overlooked.

When Jason Cryer first stepped into the world of real estate nearly 20 years ago, he did so with nothing but a dream and a relentless work ethic. By day, he worked his regular 9-to-5. By night, he drove across Houston, grabbing two hot dogs and a Coke from the 7-Eleven before heading to class from 7pm to 11pm—because back then, online real estate courses didn’t exist.

He had no roadmap, no mentor, and no one in his corner.

“I tell my agents all the time: what I do now is based on the PTSD I suffered when I started in real estate,” he says with a quiet honesty.

Jason’s early experience was a crash course in how not to teach agents to succeed. The brokerage that promised him training, support, and leads delivered none of it. The moment they had his signature and direct debit, the energy shifted. Suddenly, every resource came with a price tag—$450 a month for a contract coach, another $450 for a productivity coach. He hadn’t even sold a home yet.

“I was helping friends and family when I could, but honestly, I was drowning. There was no foundation, no mentorship. I had to figure it all out on my own.”

A Training Program Built From Pain, Fueled by Purpose

Today, Jason leads nearly 200 agents across two Monument Realty offices in Texas. And what he’s built isn’t just a training program—it’s a lifeline.

“I knew that if I ever got into a leadership role, I would make sure no agent ever felt the way I did,” he says.

Jason has followed through on that commitment, participating in the development of what’s now known as Training Camp—a hands-on, evolving initiative that goes far beyond surface-level tips. It’s real training for real-life agents. This team walks new agents through contracts, amendments, client strategy, and even how to communicate with warmth and credibility. They teach scripting, relationship-building, and how to show up for clients with substance—not just sales talk.

And unlike his own experience, every agent in this program is handed real leads—right away.

“Most agents take classes, learn the theory, and then sit on their hands because they don’t have anyone to practice on. Here, we immediately connect them with buyers and sellers so they can learn by doing—and yes, by failing forward.”

The Confidence to Lead. The Competence to Serve.

At the heart of this program are two goals: building confidence and competence.

“You have to be confident that you either know the answer or know how to get it. And you have to be competent enough to advise clients well. That’s what earns trust.”

Jason is deeply involved with agents—reviewing contracts, answering questions at all hours, and making sure no agent feels like they’re doing this alone. His role isn’t performative—it’s personal.

And it shows. From the moment agents walk in, they’re surrounded by accountability, encouragement, and real-world experience. “We don’t just talk about relationships over transactions—we show them how to actually build those relationships.”

A Story That Says It All

One of Jason’s favorite stories is about a former retail executive who dreamed of breaking into real estate. He had the ambition, but not the confidence. Jason didn’t sugarcoat it—he told him to save six months’ worth of expenses, learn the systems, and go all in when he was truly ready.

That agent listened. Today, he’s a top producer, a new homeowner, and a proud dad.

“He came to me and said, ‘You and Monument Realty changed my life.’ And that’s the part that means the most.”

More Than a Team—A Movement

Jason knows this next chapter in his career is about more than production—it’s about building a legacy and giving others the help and support which he never received in his formative years of real estate. While he remains a proud leader at Monument, his vision is to develop a brand that can keep making an impact beyond any one brokerage.

“There are agents out there—new, seasoned, and everything in between—who feel stuck, who feel unsupported. I want them to know there’s a better way. You don’t have to do this alone.”

Jason’s not just training agents. He’s breaking cycles. And he’s proving, with every story, every contract, and every success—that the right mentorship can change everything.