Stephen's hard-won rule is to scope yourself down and only start new things that fit inside your existing umbrella. After Lumiere hit ~50 people he got arrogant, started a separate "assistant company," split his attention, and ended up selling it "for not much." His line now: "once I go outside education I'm an idiot."
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Stephen says that as a younger founder he'd see someone running five companies and think "you are a fucking god" — and now he thinks "you are a fucking idiot." His own mistake: after running Lumiere for three years to about 50 people, he decided he was "so good at hiring," started an assistant company, and it just did okay while Lumiere lost his attention. "It took me about a year to realize how stupid I was." He sold the assistant company for not much. The fix he settled on, for someone who is "kind of ADHD" and loves to start new things: channel that energy inside the existing product. "I'll let myself start education companies because they fit inside the Lumiere umbrella… but once I go outside education I'm an idiot."