Most people talk about betting on themselves. Very few talk about what it actually looks like when it goes wrong.

In this episode of the We Attitude Podcast, David sits down with one of his closest friends to unpack a journey that didn’t follow a straight line—from the mailroom, to sales, to failed partnerships, to entrepreneurship, and eventually the boardroom.

This isn’t a highlight reel.

It’s a real conversation about:
- Trying before you feel ready
- Why failure isn’t the problem—fear of failure is
- The difference between being good at sales and actually running a business
- How networking becomes powerful when it’s intentional
- Why partners matter more than ideas
- And how confidence is built after action, not before

From junior hockey lessons and locker-room brotherhood to business setbacks, leadership growth, and learning to walk into rooms with purpose—this episode breaks down what betting on yourself really means.

If you’ve ever felt stuck, hesitant, or unsure of your next move—this conversation is for you.

Watch until the end for the mindset shift that separates people who talk about growth from those who actually experience it.

In this first podcast episode, David sits down with Chad Wilson from Keller Williams in the St. Louis / St. Charles area to unpack Chad’s journey from military service to real estate leadership. Chad shares how joining the Air National Guard at a young age and spending decades as an air traffic controller—both overseas and at Lambert—shaped his mindset around preparation, adaptability, and performing under pressure.

The conversation connects those lessons to real estate, covering Chad’s early experiences with rental properties, the transition into retail real estate, and how focusing on results, relationships, and “running the math” helped him build credibility with clients and builders alike. They also discuss hiring and leverage, learning through adversity, and how those principles continue to guide team growth as the industry evolves and AI begins to play a larger role.