AI Startup Founder: Hiring 100 to Find the Right 40

Jaspar Carmichael-Jack built a company that sells AI employees, but his biggest lessons came from hiring real humans wrong.

The Artisan CEO went through 100 hires to build his current team of 40. Each mistake cost time, money, and team morale, but taught him exactly what early startups get wrong when building their teams.

His first major error? Overhiring too quickly. Carmichael-Jack thought a bigger team would help the AI startup scale faster, but managing 50 people proved much harder than leading 10. In early startups, no one should have downtime.

He also fell into the "logo shopping" trap. Impressive resumes featuring tech giants like Google or Meta looked good on paper, but didn't always mean someone could thrive in startup chaos. The skills that work on well-resourced teams don't always translate to scrappy early-stage environments.

Finding the right seniority level proved tricky too. Senior hires often expected structure that didn't exist yet, while junior hires lacked the experience to build their functions from scratch. Both extremes created problems.

His biggest regret? Moving too fast to hire and too slow to fire. When someone wasn't working out, the team would spend weeks or months trying to help, but avoiding the hard decision. "You can tell when someone's not working out in a role, and usually they know as well," Carmichael-Jack said.

The irony isn't lost on anyone. A company building AI workers to replace humans learned that you absolutely cannot scale without the right people.

Why This Inspires

This story matters because it flips the AI replacement narrative on its head. Even founders betting their companies on artificial intelligence know that human talent, judgment, and grit remain irreplaceable. The key isn't choosing between humans and AI. It's about being strategic, patient, and honest about who belongs on your team and who doesn't.

Every wrong hire taught Carmichael-Jack something that made the next one better. His honesty about failure gives other founders permission to admit their mistakes and course-correct faster.

The lesson that took 100 hires to learn: the right humans don't just avoid slowing you down; they compound your success just as quickly as the wrong ones drain it.