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Dylan Fry’s Real Estate Journey: Turning Setbacks into Success

Dylan Fry’s journey is one of resilience and transformation. Faced with unexpected setbacks, he let go of old burdens, embraced coaching, and focused on sustainable growth.

Through strategic delegation, building lasting relationships, and mastering daily success habits, Dylan turned financial challenges into a thriving real estate business—creating not only professional success but also more time for what matters most: his family.

Case Study

Dylan went from a six-figure income to struggling with financial hardships, all while supporting a family of six. But by embracing Workman systems, Dylan managed to .

Here’s how Dylan did it:

After a promising start in the insurance industry, Dylan faced sudden and unexpected setbacks that took him from a six-figure income to struggling with financial hardships, all while supporting a family of six. Forced to pivot, he juggled real estate and insurance, only to find himself overwhelmed by the demands of both.

I knew I needed to make some severe changes… I had a house I couldn’t pay the mortgage on and really didn’t have money for anything. But I was determined to rebuild, and that meant focusing entirely on real estate.”

Dylan’s goal was twofold:

  1. Transition fully into real estate, leaving insurance behind.
  2. Build a sustainable real estate business that would allow him to create more time for his family while offering financial stability.

Dylan wanted to ensure that his business not only thrived but also provided him the freedom to coach his sons’ sports teams and be present for their childhood milestones.

Dylan partnered with Workman Success Systems, where he found a dedicated coach in Rob Leggat. Together, they developed a structured plan focusing on two core areas:

  • Delegation and Time Management: Dylan hired virtual assistants to manage transaction coordination, freeing him to focus on client relationships and business growth.
  • Daily Success Habits (DSH): Rob guided Dylan in setting and maintaining consistent habits that enhanced his productivity and clarity.

Together, they emphasized taking a step-by-step approach—mastering one system at a time—rather than becoming overwhelmed by everything at once.

Rob’s patience and guidance were game-changers. He didn’t just give me systems—he helped me focus on the right steps, one at a time, so I could grow my business without getting overwhelmed.”

Benefits

Dylan achieved nearly . from 2022 to 2023

Losing everything forced me to confront what truly mattered—providing for my family and building a business I believed in. It wasn’t easy, but sometimes setbacks are the push we need to pivot toward our real purpose.”

Through Workman Success Systems’ guidance, Dylan…

  • Gained More Time with Family: By hiring virtual assistants and delegating tasks, Dylan gained the freedom to coach his kids’ sports teams and spend quality time at home
  • Achieved Client Retention and Growth: Dylan built lasting relationships with clients, leading to multiple transactions and referrals, ensuring sustainable business growth
  • Built Confidence in Leadership: With Rob’s coaching, Dylan developed systems for onboarding future team members, setting a solid foundation for expansion
From the Client
"I had to let go of pride, break everything down, and start over—focusing on the right habits and building real relationships. With the right coaching and support, I turned setbacks into success, creating a business and life I’m proud of."
Workman Success Triangles
Dylan Fry
RE/MAX Advantage: Fry Home Team
Inspiration

Dylan was given a powerful reminder that .

“I had to break everything down to rebuild it, and I don’t think I would have done it without the support from Workman Success Systems.”

By embracing coaching, delegation, and continuous improvement, Dylan transformed his business—and life—despite financial challenges.

“When everything fell apart, it was the coaching, delegation, and systems that gave me the clarity to rebuild my life and business.”

Dylan’s focus on building lasting relationships with clients reflected his core philosophy: “Every client is a client for life.”

 

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Come see for yourself — Dylan’s results are typical of clients who apply the systems, processes, and behaviors their coaches identify as missing from their business.

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