Three reasons: the CEO seat at InDebted is dominated by non-technical work; ten years in, he wants a business that compounds "with or without Josh" — for decades or centuries; and the AI rebuild is hard enough that he refuses to do it part-time. "I don't want to get to a position in three years time — it didn't work, but I only gave it like 50% of my time."
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The trigger was the tooling. From the end of last year into the start of this year, Josh noticed the quality of AI tooling got so much better that he started clearing his calendar to spend more time back on the tools — and saw how much you could build with less resources. The question that stuck: what if this was the first year he founded the company, not ten years ago? "I know personally I would have been able to go a lot further with a lot less."
He's explicit that stepping down doesn't have to be the approach for everybody. Being CEO of InDebted specifically requires a lot of the non-technical components of the job — the nature of the business, the reporting structure. And the ten-year mark forced a longer view: "Now I'm so confident on the ability for the business to compound over the long term that I have to think about a world where the business exists without even me in it" — whether because he wants to go do something else, or because "literally I'm not here anymore."
The third reason is the one that made it all-or-nothing. Rebuilding things that have been around for 10 years — tech debt and organizational debt — is going to be a really hard challenge, and Josh needs to give "absolutely everything I have in order to know if I can do this."