A founder's real boss is their customer base. While keeping a board happy is important, some CEOs become so consumed with managing up that they lose sight of the product and customer needs, ultimately driving the company off a cliff despite running perfect board meetings.

A founder reflects on leaving a fulfilling lifestyle business to chase a VC-backed venture. He attributes this to the "Silicon Valley Kool-Aid"—an industry narrative suggesting that if you aren't building a potential billion-dollar company, you lack ambition or are a "loser."

The desire to be a founder is a poor motivator. True drive comes from solving a real problem you care about, which is what led to Pulse's success. Getting the ego-driven desire out of the system first allows for a focus on product-centric building and user value, rather than personal identity.

The most significant founder mistakes often arise from abandoning one's own judgment to do what is conventionally expected. Jason Fried notes that these errors feel worse because you aren't just failing, you're failing while trying to be someone else, which undermines the core identity of your company.

Many founders start companies simply because they want the title, not because they are obsessed with a mission. This is a critical mistake, as only a deep, personal passion for a problem can sustain a founder through the inevitable hardships of building a startup.

When founders define success by external metrics like net worth or exit size, the target constantly shifts upward upon achievement. A $1 million goal becomes $10 million, and a single exit becomes a need for multiple. This creates a perpetual cycle of striving without ever feeling successful.

Technically-minded founders often believe superior technology is the ultimate measure of success. The critical metamorphosis is realizing the market only rewards a great business model, measured by revenue and margins, not technical elegance. Appreciating go-to-market is essential.