If life came with a plotline, Jeremiah Ajayi clearly missed the memo. He started out studying Law but somehow ended up building content strategies for global tech brands. In between, he wrote romance novels, got rejected by Piggyvest (only to be hired later), quit jobs, and lost everything. Twice.
He’s led content at startups like Stears and RemotePass, and built a personal brand that opens doors. In this conversation, he talks about lying his way into his first SEO job, learning to negotiate, losing it all, and how embracing chaos helped him build a career that makes sense only in hindsight.
If your career journey were a movie, what would the title be and why?
I’d call it Zigzag. That’s the best way to describe my career. Nothing about it has been linear. Sometimes I even ask myself, ‘Jeremiah, when do you stop living such a chaotic life?’ I was in school, doing well, but dropped out when my tech career started to take off. I’ve fallen and risen more times than I can count. It’s been messy, unpredictable, and full of detours, but that’s also what makes it mine.
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Last updated: October 23, 2025
