How to Bet on Yourself: From the Mailroom to the Boardroom
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How to Bet on Yourself: From the Mailroom to the Boardroom
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About this listen
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.