Josh's definition: "systems and processes that exist outside and around the product... that you haven't looked at from a technology lens." Tech debt is real but can be overcome; org debt is the one he "freaks out about" — because "we haven't yet seen real cases of people getting through sort of the old debt."
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Take any part of the organization — accounts payable, recruitment — and chances are it's "definitely probably not AI native. It's potentially tech enabled at its best," running on some SaaS platform, but you've never had the opportunity to throw engineers at it and rethink how it should work.
Josh's hypothesis is that AI-native businesses that went from one person to 50 "haven't probably gone and reached for the same HR system that InDebted and most of the other companies use." That's part of how they attract incredible talent quickly while remaining incredibly lean and fast. The troubling part for a 10-year-old company: there are no proven playbooks yet for incumbents working their way out of the old debt.