Remember to Smile vs the Grindset CEO
- https://www.youtube.com/watch?v=L_JgETH8zKM
- Original title: Worst Advice Ever
Prime reacts to a viral Twitter story about a CEO who presented a four-word slide — "remember to not smile" — to ~50 employees, riffing on Travis Kalanick's marathon-runner-at-mile-21 grindset metaphor. Prime dismantles the hustle-porn framing: the company in question is just a docs site, the "play not to lose" mindset is corrosive, and joy is the actual secret weapon for sustaining hard work. His counter-thesis — remember TO smile.
The story and the premise
A CEO stands in front of ~50 employees with a slide deck containing four words: "remember to not smile." Confused looks, nervous laughs, awkward silence, and someone asks what it means. The premise traces to Travis Kalanick on a podcast: picture a marathon runner at mile 21 — are they smiling? No. If they are, they're about to get passed by someone who signed up for the pain. The CEO extends it to himself — staying at the office until 4am shipping features to win customers, making painful-but-right decisions, never smiling through any of them. Prime concedes the line "kind of goes hard," since he's also pulled 4am feature nights.
The gap between the rhetoric and the product
The puncture: the company is a documentation site — "docs for your startup, docs for your agents, enterprises." Prime's mockery is that the CEO writes "like he's working at Anduril writing Haskell doing defense weapons," at war, when it's a self-hosted doc site. He grants that products are always more complicated on the inside than they look, so the disconnect isn't proof of laziness — but the war-footing tone over docs doesn't add up. He cites a favorite parody: a single-slide CEO who instead just walks up and punches you in the stomach.
Why the mindset backfires
Prime's core argument: telling people not to smile makes the company a place nobody wants to work. He wants to work somewhere filled with joy, camaraderie, and purpose — that's what actually encourages people to work harder. Late nights and hard work without joy, connection, or camaraderie are not a long-term or sustainable solution. Crucial distinction: an owner working brutally hard makes sense because they own it; expecting a mere employee to give 100% at all times, never smiling, is absurd on its face.
The deeper diagnosis: the CEO reads as someone trying not to lose rather than playing to win. Playing to win is fun, forward-facing, going for gold; playing not to lose fixates sideways on the competition. He invokes Boss Baby — focus on hitting the tree and that's what happens; focus on winning, not on not losing.
Smiling as a real performance tool
Prime's personal proof: waking at 4:50am, streaming 5–9am, then working at Netflix 9–5 for years before retiring to do content full-time — 12-hour days plus being present for family. He could not have done it without smiling through it; he looks back on those exhausting years fondly because he ran the race well. He points to Eliud Kipchoge (the sub-two-hour marathoner), who runs with a smile because the pain is so great that smiling lets him go harder, longer, faster — training programs now model this, finding that smiling lets you work harder. Joy is a secret weapon; "remember to not smile" will destroy you. Closing note of optimism: we live in one of the greatest time periods ever — you don't even need to program well to build something complex, since you can ask the "magic rocks" how to do it. So, remember to smile.