Companies often hire executives from target customers to influence product and sales. These hires dictate features based on anecdote, consuming development resources for little return. When their promised sales fail to materialize, they are quietly dismissed.

Working at Google conditions you to take user acquisition, talent recruitment, and marketing for granted. When ex-Googlers start companies, they are often unprepared for the fundamental challenge of getting anyone to care about their product, a skill they never had to develop.

Early-stage founders often mistakenly hire senior talent from large corporations. These executives are accustomed to resources that don't exist in a startup. Instead, hire people who have successfully navigated the stage you are about to enter—those who are just "a few clicks ahead."

The ideal early startup employee has an extreme bias for action and high agency. They identify problems and execute solutions without needing approvals, and they aren't afraid to fail. This contrasts sharply with candidates from structured environments like consulting, who are often more calculated and risk-averse.

Avoid hiring a growth leader with a big-name pedigree for your early team, as they are often unsuited for the necessary hands-on experimentation. Instead, seek young, hungry builders who are motivated by chaos and comfortable rebuilding their own work as the company's needs evolve.

Neil Blumenthal warns that hiring talent from large, established companies can be a mistake. These hires often thrive in environments with fully built-out systems, whereas a startup needs entrepreneurial problem-solvers who can create those processes and manuals from scratch.

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."

C-level hiring is exceptionally difficult, with a high failure rate. Data from MongoDB's CEO shows an average of two C-level turnovers per year. HubSpot's co-founder Brian Halligan estimates that at least 50% of newly hired C-level executives are gone within 18 months.