The Beginning of an Entrepreneurial Mindset
From an early age, Jayson Meyer was a tinkerer, always driven by curiosity and a passion for learning. Fascinated by how things worked, he spent his childhood experimenting, building, and solving problems. He dreamed of becoming an inventor, constantly seeking ways to improve the world around him. Advanced for his age, Jayson’s talents and intellect were recognized early, and at just 17 years old, he appeared on The Oprah Winfrey Show in an episode themed “Smart Kids.” This moment was a testament to his entrepreneurial spirit and problem-solving mindset—qualities that would define his career and shape his success in the business world.
Entrepreneurship isn’t just a career choice; for some, it’s a calling. For Jayson Meyer, the journey began in middle school when he started building computers and developing software. By high school, he had launched his own technology company, driven by a passion for problem-solving and innovation. “The ability to take an idea, refine it, and bring it to life fascinated me,” Meyer recalls.
In the late ’90s, while working with doctors, he noticed inefficiencies in medical billing and attempted to develop an online billing software called WorkSmart MD. In the early days of the internet, this technology was ahead of its time, but Meyer never lost sight of his vision. Before the COVID-19 pandemic, he revisited the concept, this time integrating a unique algorithm he created to predict whether medical claims would be paid. “One in three medical claims is denied due to data problems,” Meyer explains. “Our software, WorkSmart MD, and its proprietary algorithm help predict whether a claim will be paid the first time to avoid a denial for payment.”
Today, his company, Synergy Billing, is the primary customer of WorkSmart MD, and the software has significantly improved the cash flow and operational efficiency for healthcare providers. Some health centers using WorkSmart MD have seen as much as 98% of their claims being paid on the first attempt. In an industry mired with delays and inefficiencies the implications are profound.
Overcoming Challenges: Scaling While Maintaining Quality
One of the most significant challenges Meyer faced was scaling Synergy Billing while maintaining quality and culture. “Early on, I had to wear multiple hats—sales, operations, HR, client success—until I could build the right team,” he explains.
As Synergy Billing grew, he realized that sustainable expansion required clear systems, strong processes, and leadership development. “It took me three iterations of ‘failing forward’ before I was able to scale the company effectively,” Meyer says. The key to success was creating a solid operational framework, assembling a leadership team aligned with the company’s mission, and fostering a culture of continuous improvement.
Leadership Philosophy: Purpose, Clarity, and Execution
For Meyer, great leadership is about clarity, accountability, and inspiring people to achieve more than they thought possible. “My philosophy is rooted in helping people, places, and things become the best they are capable of being,” he says. His leadership principles include:
- 1. Lead from the front. “Show, don’t just tell.”
- 2. Problems are opportunities. “Every challenge is a game that can be solved.”
- 3. Credibility capital matters. “Do what you say you’ll do—trust compounds over time.”
- 4. Think big, but act decisively. “Vision without execution is just a dream.”
- 5. Maximize time and energy. “Focus on high-impact activities and eliminate distractions.”
Meyer believes leadership isn’t just about driving results—it’s about creating an environment where people can thrive, innovate, and exceed expectations.
Handling Failure: The Data of Success
Meyer embraces failure as an integral part of success. “Every setback I’ve faced—whether it was the failure of my first software, hiring the wrong people, or industry disruptions—has been a stepping stone,” he explains. He views failure as data, providing valuable insights into what didn’t work so improvements can be made.
“One of the best lessons I’ve learned is to fail fast, adapt, and keep moving forward,” he says. “If you’re pushing boundaries, you will fail at some point. The key is to extract the lesson, refine your approach, and execute better next time.”
Advice for Aspiring Entrepreneurs
Meyer offers the following advice to those looking to embark on an entrepreneurial journey:
- 1. Get clear on your purpose. “The ‘why’ matters more than the ‘what.’”
- 2. Take action. “Don’t overthink—start, iterate, and refine.”
- 3. Surround yourself with the right people. “Your network will shape your success.”
- 4. Be relentless. “Success comes to those who refuse to quit.”
- 5. Enjoy the process. “If you don’t love the journey, you won’t sustain the grind.”
The Reward of Building Teams and Leaders
Meyer considers his most rewarding achievements to be those involving the development of his team. “Success isn’t about personal wins—it’s about building an environment where others can thrive, grow, and reach their full potential,” he says.
One of his greatest accomplishments has been assembling high-performing teams and empowering them with the tools, support, and resources they need to succeed. “By focusing on the right people, creating strong systems, and fostering a culture of accountability and innovation, I’ve watched individuals evolve into exceptional leaders.”
Education and Continuous Learning
Meyer attributes much of his success to his ability to learn, question, and understand new information. “One of the most important things in life is understanding how you learn and process information,” he states. “I consider myself a student of life and business, and my greatest education has come from over 25 years as an entrepreneur—building businesses, solving complex problems, and leading teams.”
While experience has been his greatest teacher, Meyer has supplemented his learning with executive education from Wharton Business School and MIT, sharpening his skills in leadership, strategy, and innovation. “Continuous learning and adaptability are the foundations of long-term success,” he adds.
The Biggest Challenge in Entrepreneurship Today
Meyer believes one of the biggest challenges in entrepreneurship today is recognizing the difference between launching a business and scaling it. “The skills required to start a business—creativity, persistence, and adaptability—aren’t necessarily the same ones needed to build a company that scales sustainably,” he notes.
“The transition from founder to CEO is one of the hardest because it requires a shift in mindset,” Meyer explains. “You have to go from doing everything yourself to building systems, empowering people, and trusting a team to execute your vision.”
Visionary Leadership and the Future
For Meyer, being a visionary leader means seeing what’s possible before others do, thinking beyond the immediate, and aligning actions with a long-term mission. “I don’t just focus on what exists today—I think about what should exist and then work to make it real,” he says.
Entrepreneurship is a journey of resilience, adaptability, and continuous learning,” Meyer states. “The most successful entrepreneurs aren’t just those who innovate-they are the ones who lead with purpose, embrace failure, and empower those around them. Whether you’re just starting out or scaling your business, remember: success isn’t about avoiding challenges-it’s about turning them into opportunities.”