Early in her career, Emma Grede hired an experienced managing director from a competitor, paying him three times her own salary. He failed because he lacked the 'entrepreneurial grit' she possessed. This highlights a common founder mistake: assuming an impressive resume can replace the unique vision and drive of a founder.

Prioritize hiring generalist "athletes"—people who are intelligent, driven, and coachable—over candidates with deep domain expertise. Core traits like Persistence, Heart, and Desire (a "PhD") cannot be taught, but a smart athlete can always learn the product.

A frequent hiring error is choosing candidates because you believe they possess "magical knowledge" from their specific background that will solve all problems. These hires often fail by rigidly applying an old playbook. Prioritize adaptable, curious problem-solvers over those with seemingly perfect but ultimately static domain expertise.

When hiring, a candidate with high passion for the subject matter but low experience is more valuable than an experienced candidate with low passion. Skills are teachable, but genuine enthusiasm for the mission is not. This framework helps resolve the common hiring dilemma between potential and polish.

Bhaskar Sunkara's top advice for founders is to 'fail fast on hiring.' He stresses not hesitating to part ways with someone who isn't scaling, even if you fear losing their institutional knowledge. The long-term damage of a poor fit is greater than the short-term pain of replacement.

Founders often chase executives from successful scaled companies. However, these execs can fail because their experience makes them overly critical and resistant to the painful, hands-on work required at an early stage. The right hire is often someone a few layers down from the star executive.

Hiring someone with a prestigious background for a role your startup isn't ready for is a common mistake. These hires often need structure that doesn't exist, leading to their underutilization and boredom. It's like using a "jackhammer when all we needed was a sturdy hammer."

Don't default to hiring people who have "done the job before," even at another startup. Unconventional hires from different backgrounds (e.g., archaeologists in customer success) can create unique creativity. The priority should be finding the right fit for your company's specific stage and needs, not just checking an experience box.

Chang reflects that his past hiring errors came from over-weighting raw intelligence and under-weighting whether a candidate 'deeply cares' about the mission. He now prioritizes finding people who will stay up late to fix a bug because they are personally invested, not because they are told to.