My 24/7

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.

Society has one scoreboard for entrepreneurs: revenue. Brian and Carl argue for a different one. From a fisherman parable to what an NFL therapist told Brian about success, this episode is about defining what winning actually means before the world defines it for you.In this episode:Carl's real goal in Albuquerque: being the name small businesses think of — and why his first $500 deal meant more than a million would haveHow Brian's success metrics changed when his matcha cafe landed downtown instead of the suburbs, and what it takes for a franchise to feel local in a city allergic to chains"I'm not competing with other matcha cafes — I'm competing with everybody" (the Netflix theory of competition)The fisherman and the rich guy: the parable every founder should sit withWhy "getting on the field" is the win, and how chasing the outcome ruins the everydayThe advice both wish they'd gotten: set small, checkable goals — momentum beats magnitudePlus: scam attempts on small businesses (five in one week, one that landed) and the eternal "source of truth" problem.New episodes every Tuesday.

Most people leave a job in a reactive moment — bad boss, bad quarter, bad Tuesday. Brian pulls out his old tech-sales discovery playbook and runs it on Carl's decision to go independent: what was the real pain, what did ownership actually promise, and what had to be true before the leap made sense?In this episode:Why one bad day isn't a signal — and Carl's six-month "annoyance inventory" that isThe two sides of ownership: equity (and what watching a $12B acquisition without any taught Carl) and controlling the whole solution end to end"Artificial friction" — the approval layers that exist for no technical reason, and what disappears when you leaveThe runway math: nest egg, a spouse's stable income, and how the calculus changes if you're the sole breadwinnerGetting over the resume-gap fear and what people will thinkWhy frustration only fuels the fire for a little while — you need a specific picture of success to keep goingPlus: a cross-country drive, a weighted-vest bait and switch from Costco, and marketing automation that skips the small talk.New episodes every Tuesday.

Two tech careers, two very different leaps. Carl spent years at Mailchimp, Zapier, and Webflow before betting on himself; Brian went from tech sales to opening a matcha tea franchise on Market Street in San Francisco. In the debut episode of My 24/7, they compare notes on what the jump actually looks like.In this episode:Why "autonomy and ownership" finally outweighed a comfortable tech paycheckThe invisible two-to-three-year runway behind that shop that "just appeared" on your cornerWhy commercial real estate moves at a pace that breaks a tech brain — and the Queens lawyer out-hustling DocuSignCarl's renovation rule for budgeting: whatever you think it costs and however long you think it takes, pad itThe one thing each of them would tell you before you take the leap: don't marry the plan, and find your community earlyNew episodes every Tuesday.