Leadership in STR: Building A-Player Teams That Scale

Kaye Putnam: I watched a video recently where Simon Sinek said, "Pressure is a privilege." It really resonated because our Freewyld team is feeling that right now. We are growing fast, scaling quickly, and navigating all the challenges that come with it. Today we want to take listeners behind the scenes of what leadership actually looks like during this kind of growth.

Eric Moeller: Things are moving fast. Our businesses are expanding, team members are having babies, we are onboarding new clients. It is exciting but also intense. This stage is forcing me to think differently about where my time and energy go. I cannot be in the weeds anymore. My job now is to lead and make decisions that move the company forward.

Kaye: Leadership feels different when you are in this growth phase. Who or what has shaped your approach to leadership the most?

**Eric:**I have been influenced by many people. CEOs, entrepreneurs, and military leaders who lead with heart and humility. A big one for me was Jocko Willink’s Extreme Ownership. That mindset helped me build discipline and accountability. Early on I was in attack mode, constantly pushing. Now I am learning to lead more strategically.

**Kaye:**My husband was an officer in the military for over a decade, and I learn so much from watching how he leads, with structure but also care. He would call himself a servant leader, and I try to bring that into our smaller team. It is about helping people grow, knowing that when they get better, the company does too.

**Eric:**Exactly. Whether you are leading two people or two hundred, it is about alignment, shared vision, and shared values. We have been watching Ted Lasso lately, and it reminded me how one person can either elevate or disrupt an entire team culture. That is why hiring for cultural fit is so crucial. A single misaligned person can create chaos, while A-players make everything flow.

**Kaye:**So true. Culture happens whether you design it or not. When we started Freewyld, we aligned naturally as founders, but as we grew past a dozen team members, we realized culture needed to be intentional, even documented. How do you describe our culture now?

**Eric:**It is definitely evolving. We brought a lot of what we built at RPM into Freewyld, but now it is becoming its own thing. What is clear is that we are a hospitality company at heart. Unreasonable hospitality is in our DNA. And we are surrounding ourselves with A-players who do not need to be micromanaged. We lead them, not manage them.

**Kaye:**Yes. I think of an A-player as someone who is both humble and hungry. They are great at what they do but always eager to grow. Those two traits, humility and hunger, are what I look for most when hiring.

**Eric:**I love that. Humble and hungry could be one of our core values. It captures who we are. We get results without ego. Our team genuinely loves what they do, and you can feel it. It is passion-driven, not control-driven.

**Kaye:**That is why we work well together. We can have open feedback conversations without ego. I have learned a lot from watching how you handle that balance, being a visionary but also staying receptive to feedback.

**Eric:**That has been a huge evolution for me. I used to chase every idea that came into my head. Now I ask, does this align with our main goal? Will it distract the team? I write everything down and only act when it truly drives the business forward. That is leadership, choosing what not to do.

**Kaye:**Exactly. We both have that "good idea fairy" syndrome, and learning to filter is key. When you realized it was time to shift from your old business to Freewyld, what was that turning point for you?

**Eric:**I just was not fulfilled. Our previous business was successful, but the model required constant selling and it started to drain me. I was not excited anymore. Then I went on a road trip, stayed in different Airbnbs, and it hit me. I could do this forever. I love hospitality. That clarity made me go all in on Freewyld.

**Kaye:**It is a reminder that passion and purpose can coexist with performance. You mentioned shifting from attack to strategy mode. What triggered that?

**Eric:**In the beginning, it was survival, just pushing through. But once marketing and sales started clicking, I realized it was time to focus on leadership, structure, and long-term growth. We have leaders now within the team. I do not need to make every decision. My role is to help others lead.

**Kaye:**I have seen how you approach it, identifying bottlenecks, fixing one area at a time, and then moving on. It is like agile leadership, short sprints that create momentum. How do you balance holding high standards without micromanaging?

**Eric:**Overcommunication helps more than overcontrol. I record processes, train others, and then step back. When I do jump into a task, I use it as a teachable moment so I never become the bottleneck. Leadership is about building systems and trust.

**Kaye:**And hard conversations are a huge part of it. How do you approach them?

**Eric:**I used to avoid them. Growing up, confrontation meant yelling, not resolution. That changed when I learned to approach conflict with curiosity. Ask questions. Listen. Figure out if it is a training issue or a culture issue. When you remove ego and focus on clarity, hard conversations actually build trust.

**Kaye:**That is so true. I come from a culture that avoids conflict, so I have had to learn to face it head-on. It is a muscle you build, like leadership itself. What is the biggest challenge for us right now as a company?

**Eric:**Connection. We are a fully remote team spread across the world. The hardest part is maintaining alignment and connection without being in the same room. In-person offsites have been game-changers for us. I want more of those next year to keep building that sense of unity.

**Kaye:**Every offsite I come back more energized and connected. It is essential, especially now that we are out of survival mode and moving into scaling. Our challenge is to keep growing while staying grounded in our vision and values.

**Eric:**Exactly. We are building something special, a hospitality company with a soul. That requires leading through culture, not control.

**Kaye:**Beautifully said. And to everyone listening, we would love to hear what you are learning as a leader. Send us a message on LinkedIn and let us keep the conversation going.

**Eric:**Appreciate you all for tuning in. See you next time.