A new playbook for today's best leaders: A Conversation with Wine to Water CEO David Cuthbert

Welcome to the Good Life Property Management podcast! I’m your host, Steve Welty. This is a show for property management entrepreneurs who want to build not only a great business but also great lives. I’m here to help you gain the freedom to live life on your own terms while creating a positive impact in the world. Also, please check out Steve Welty’s Music!

On this episode, I chat with David Cuthbert, who was introduced to me through a childhood friend. We talk about how a person’s energy can shift your perspective. Leading teams is our big concept I talk about with David today. What are the elements which keep a person from becoming a leader? David chats about his formal education with leadership classes and his personal experience with leadership throughout years of his career.

We talk about the differences in leadership over time, cultural sensitivity, and globalism in relationship to changing the leadership role. What are the types of conversations you need to have to become a good leader? David discusses how success, technology, and culture hold equal weight in a company when it comes to leadership prosperity. Fostering the health of your team environment and culture is essential to build your company upon.

David and I dig into the ingredients which create a recipe for successful leadership. Which fundamental components can you not shortcut in leadership? David speaks about the five ways you can build trust as a leader. Dale Carnegie’s How To Win Friends and Influence People dives deep into leadership and how to influence people to work, including appreciating others for their work. Team of Teams by Stanley McChrystal is another team book which David highly recommends, along with Extreme Ownership by Jocko Willink. The Boys in the Boat is another favorite read of David’s, and this book is written around the concept of “swing” in the rowing community.

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In This Episode:

[00:58] - Background on our mutual friend Eric, including the time when I had a homeless man take my keys!

[04:48] - What are the elements which prevent us from being able to lead a team?

[07:25] - David talks about his experience with learning about leadership and how leadership is a very dynamic field.

[10:40] - Providing an environment for a successful leadership.

[12:02] - David speaks about the execution of the mission and why we shouldn’t be solely focused on the mission.

[15:08] - How David replicated team comradery from his military experience in his technology career.

[18:33] - What David does to bring team members who need leadership coaching up-to-speed.

[23:52] - Formulas for success are great, however, trust cannot be hacked! Five ways a leader can build trust with their team.

[29:26] - Situational awareness and leadershi