Don't hire preemptively. Katelin Holloway's "hire when it hurts" principle advises founders to perform a job themselves until they are overwhelmed. This ensures they develop a deep understanding of the role's requirements and sincere empathy for the person they eventually hire, leading to better hiring decisions.

Before hiring for a critical function, founders should do the job themselves, even if they aren't experts. The goal isn't mastery, but to deeply understand the role's challenges. This experience is crucial for setting a high hiring bar and being able to accurately assess if a candidate will truly up-level the team.

A critical positive signal for investors is a founder who can honestly self-assess their skill gaps. This humility and willingness to hire people who are better than them in specific areas, even with differing personalities, demonstrates the maturity needed to scale a business.

Many leaders hire defensively, trying to avoid a costly mistake. This fear-based mindset leads to negative assumptions and misinterpretations of candidate signals. Shifting to an abundance mindset—believing the right person is out there—fosters curiosity and leads to better evaluation and hiring outcomes.

Founders fail at hiring because they try to replace themselves with a single person who can do everything—a unicorn that doesn't exist. Instead, break down the role into its core functions (e.g., the horn, the horse, the sparkle) and hire multiple, more easily-found specialists to fulfill those distinct needs.

Interviews are often misleading. A trusted recommendation from a high-performing employee or contact is a more reliable signal of a candidate's quality than your own interview assessment. This "reference hiring" is a secret weapon for building a strong team.

Unlike multi-founder teams, solo founders lack built-in executive coverage. To compensate, they should hire senior leaders sooner than typical, even with a small team, to own critical functions and enable the founder to focus on other fires.

For high-stakes decisions like hiring, Livestorm's CEO uses a simple heuristic from his mentor: "When there is a doubt, there is no doubt." This means that if you have any significant hesitation about a candidate, the answer should be no. This framework forces a default to certainty, preventing costly mistakes that arise from ambiguous feelings.

Experienced founders have a critical advantage: they can personally vet key hires based on years of observation. First-time founders often rely on their board's recommendations, which can lead to mismatched hires ("organ rejection") because they lack the firsthand context to judge fit.