“you got to trust them to a certain point and a lot of times I don't think of it as my money I think of it as just the business's money and so that helps a little bit in terms of the mentality”

Decouple your personal money from the business's money to actually delegate

Bootstrapped founders freeze when an operator wants to spend $10K because it feels like personal money. Reframing the bank account as the business's capital — not yours — is what makes delegation psychologically possible. Big checks still get reviewed, but via questions, not dictates.