The Drive
Ep 33: Think Bigger: With Connor Hassoun
Craig once asked his business partner Chad for a million dollars to get their company off the ground, and Chad said yes without hesitation. That moment kicks off a wide ranging conversation with Connor Hasson about why so many people, even successful ones, end up thinking smaller than they should. They talk about the three tells that someone has stopped growing: the way they talk about the past instead of the future, where their money actually goes, and whether their circle still challenges them or just agrees with everything they say. There's a real critique of the recruit-everyone playbook that dominates their industry, and why hiring fewer people and training them harder built something more durable. From there the talk turns toward ego and identity, especially the moment a founder has to stop being the best performer in the room and start building people who outperform them. Craig tells a story about a $100 lunch with author John Maxwell that ended with one sentence that stuck with him for years, and there's a genuinely interesting bit about a goldfish that grows two inches in a bowl but over a foot in a lake, used to make a point about how much environment shapes potential. Somewhere in the mix of business talk and a Ted Lasso tangent, they arrive at the idea that letting go, of failures and of past wins alike, is what actually makes room for the next level. Part two picks up where this one leaves off.
