Leadership Shaped by Curiosity, Risk, and Trusted Relationships

Dave McCaslin reflects on early lessons from baseball, where rotating through the weakest team positions taught him teamwork, fluidity, and how to build teams. He describes a traditional start in hotel operations followed by a pivotal choice in his late twenties to help start a company - an experience that led him to a career as a serial entrepreneur. Dave shares how curiosity guided his decisions and how moving into larger leadership roles required learning to let go, delegate, and rely on others. He explains that risk is inherently “scary,” yet planning, looking far down the road, and surrounding himself with trusted people helped him take bold leaps, including leading major hotel projects with very small teams.

Dave emphasizes learning from setbacks, including hotel deals that failed and a startup where cultural misalignment proved more challenging than financial performance. He highlights the importance of trust, shared values, and how people behave under pressure. He also describes building authentic, long-term relationships, approaching networking without transactional intent, and finding mentors and champions who genuinely want to help.

Quotes/Highlights

• “Risk is called risk because it’s scary.”
• “You learn more from what you don’t do well than what you do well.”
• “Most people are basically good… if you allow them to be good.”
• “It’s not a sign of weakness to ask for help.”
• “You want to know that you can get through [difficult] periods with the people that you’re with.”

Closing Reflection

Dave encourages recognizing what you value, understanding your long-term goals, and being ready when rare career-defining opportunities appear. He reminds us that careers unfold over time, shaped by preparation, awareness, and trusted relationships.

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