The Questions We Wish We'd Asked Sooner

Carl was employee #80 at Mailchimp and never asked the founders to coffee. Brian shared a breakfast table with his CEO and CFO every morning and never asked how the company got built. This episode is about the access most people waste early in their careers — and the harder questions both wish they'd asked before starting their businesses.In this episode:Why "be curious about the roles around you" beats collecting buzzwords you only understand well enough to sellThe right way to ask for someone's time (and the entitled way that gets you ghosted right back)Ask executives "what's hard?" — not fan questions; nobody has it figured out, and they know itStudy the failures, not just the unicorns: the road to Y Combinator is littered with great ideasCarl's hardest lesson: the market told him small businesses don't buy "AI" — they buy solved problemsBrian's missing plan: "if nothing works, what do we do?" — and knowing when to take your money off the tablePlus: Carl's first kidney stone, AI fatigue, and Brian finally visits Alcatraz.New episodes every Tuesday.