Can You Get Rich with A Blue Collar Hustle? | My First Million Q&A (#457)

Sam says any route to making money is fine, but he personally prefers “digital” businesses because they can require little capital, are location-flexible, and can scale in ways that feel harder in brick-and-mortar.

Shaan argues you should pick the way of “winning” that matches the lifestyle problems you’re willing to have, and says the idea of “not competing with Stanford grads” is a catchy line but not the real reason internet startups fail (they fail because you can’t get attention or the market doesn’t want it).

Sam says he’s repeatedly hit financial targets he thought would remove anxiety, but the worry returns; Shaan reframes “enough” as arranging days where the activity itself is the reward, citing the idea that retirement is stopping the sacrifice of today for an imagined tomorrow.

Both describe expecting deals to fall through and trying to stay emotionally detached; Shaan adds a rule-of-thumb that even successful deals often “break up” (walkaway moments) twice before closing, and he shares advice to discount offers based on how far along they are and perceived ability to close.

Sam recommends proactively revealing “skeletons” early in a deal process to avoid wasted time and build trust; Shaan confirms he used this approach during the Milk Road sale and says the buyer later told him it materially increased trust.