By: Jordan Miller

For entrepreneurs chasing quick wins, Tyler Rees has a different philosophy: sustainable success is built through consistency, not speed.

“If I had to give one piece of advice to founders,” says Rees, “it’s that business is earned in the trenches, not on the timeline.”

As the founder of EnrollHere and a key architect behind billion-dollar partnerships in the Medicare space, Rees has built his reputation on long-term thinking and relentless execution. His approach centers on three core principles.

1. Outserve

Serve people before you sell them. Whether it’s clients, carriers, or agents, make them feel like you would still show up even if the deal didn’t close.

That philosophy of genuine service has helped Rees earn the kind of trust that scales. He believes relationships built on value rather than urgency are the ones that endure.

Building trust through service is not a one-time effort but a constant commitment. For Rees, every interaction with a client, partner, or agent is an opportunity to reinforce his philosophy of outserving. “People remember how you made them feel, not just what you did for them,” he shares. This mindset requires a deep sense of empathy and a willingness to invest in relationships for the long haul. By focusing on the well-being of others before considering the transaction, Rees creates an environment where collaboration thrives. When others see that you prioritize their needs over your own immediate gain, loyalty naturally follows. That’s why Rees’s approach to business isn’t transactional; it’s transformative.

2. Outthink

Rees emphasizes the importance of deep research and market awareness.

Study the cracks. Spot the trends. A great pitch means nothing without a clear and informed understanding of the market.

That obsession with context and clarity has shaped how Rees identifies opportunity, anticipates challenges, and stays ahead of the curve.

Rees’s strategy of outthinking the competition goes beyond just understanding trends—it’s about cultivating a mindset of continuous improvement and agility. “Markets are dynamic, and your strategy must evolve as quickly as the forces around it,” says Rees. His ability to read the room and predict market shifts has allowed him to pivot when others are stuck. By taking a data-driven, almost scientific approach to understanding consumer behavior and industry movements, Rees makes informed decisions that keep him ahead. This relentless drive for knowledge doesn’t stop with a single success; it’s a perpetual quest for better solutions, smarter approaches, and sharper insights that provide a competitive edge in any environment.

3. Outlast

In Rees’s view, many entrepreneurs give up just before they reach the finish line.

Most people quit on the 98-yard line. Entrepreneurship rewards those who endure. If you are willing to keep going when others stop, you win.

It is a mindset that has defined Rees’s career. He does not chase shortcuts. He builds around standards.

Endurance isn’t just about staying in the game longer—it’s about maintaining focus and consistency even when faced with challenges. According to Rees, the true test of an entrepreneur’s resolve comes during the hardest moments, when quitting seems easier than pushing forward. “It’s not about being the smartest or the fastest; it’s about who can keep their head in the game when everyone else is distracted or burned out,” he says. In his career, Rees has encountered many obstacles, but it’s his ability to stay steady and committed that has propelled him toward success. For him, outlasting is more than just a strategy; it’s a way of life, an ethos that has sustained him through every high and low.

Playing for Legacy:

Photo Courtesy: Tyler Rees / Innovative Financial Group

“I have built billion-dollar partnerships off two things,” Rees says. “How I treat people and how well I understand the game.”

His playbook is simple: do the hard work, take the long view, and build only with people who are in it for legacy, not just a quick return.

In an environment where speed often gets more attention than substance, Tyler Rees continues to build slowly, deliberately, and with purpose. His results speak for themselves.

Disclaimer: This content is provided for informational purposes only and should not be interpreted as professional, legal, medical, or financial advice. Readers are encouraged to consult with a qualified professional for specific advice tailored to their individual circumstances.