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.

Brian Halligan reflects that as HubSpot grew, he was coached out of his natural 'founder mode' instincts (e.g., many direct reports, public feedback) and into conventional 'manager mode' (weekly one-on-ones, private criticism). He now regrets this shift, believing his initial, more unconventional approach was more effective.

Brian Halligan graded his performance and happiness as CEO based on company size. He felt most effective and enjoyed his work most in the 10-1,000 employee range, focusing on customers and employees. Beyond that, the work became less interesting and more administrative, suggesting a founder's ideal stage may be finite.

Brian Halligan notes that the founder's experience is a constant state of '996' work hours and dealing with problems. He claims 90% of the inputs (emails, Slacks) are bad news, a ratio that surprisingly doesn't improve even when the company grows from a startup to having 10,000 employees.

A founder admits his agency fell into an "ego trip," chasing vanity metrics like employee headcount and opening international offices. While impressive at cocktail parties, this focus on scale over substance destroyed profitability, making the business feel more like "a charity."

Early in its journey, HubSpot secured a deal with Meta that would have doubled its quarterly revenue. However, founder Brian Halligan tore up the contract because Meta was far outside their ICP. Servicing them would have derailed the product roadmap and company focus, ultimately destroying the business.

To truly build a people-first culture, give the head of HR (rebranded as 'Chief Heart Officer' to change perception) more political clout and decision-making power than the Chief Financial Officer. This organizational structure ensures that employee retention and happiness are prioritized over pure financial metrics, leading to long-term stability and success.

Home Depot's culture inverts the traditional corporate pyramid. The most important person is the frontline employee interacting with the customer, not the CEO. This philosophy ensures that the entire organization is structured to support the people who directly create the customer experience and drive sales.

HubSpot's co-founders were driven by the goal of becoming the biggest tech company in Boston, not the world. While VC Marc Andreessen views this "local maximum" thinking as a flaw, for HubSpot it provided a powerful, tangible anchor that fueled their long-term focus and prevented them from selling early.