I'm sitting on a private jet with Tom Patterson and Chandler Bolt, and the obvious question comes up: when does this kind of spending actually make sense?
Once your business starts producing real money, the decisions don't necessarily get easier. Do you keep pouring everything back into the company? Spend more to save time? Pay for experiences and access to better rooms? Or are you just copying the lifestyle of someone who's ten years ahead of you?
We get into the tension between frugality and leverage, why entrepreneurs can spend years being able to afford something before feeling comfortable buying it, and how trying to look successful can actually hurt your credibility with the people you're trying to impress.
We also talk about the role relationships and proximity play as you scale—and why being around people operating at a completely different level can change what you believe is possible.
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