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.
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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.
Blippar's co-founder realized her skills were perfect for the startup-to-scale-up phase but that she became a bottleneck at scale. Her inability to delegate meant others were better suited to lead the scaled team. This self-awareness is crucial for founders to prevent stalling growth and empower their organization.
Citing Unity's CEO, Adrian Solgaard highlights the "messy middle" of scaling (from 12 to 100 employees). This awkward phase lacks the intimacy of a small startup and the structure of a large corporation, requiring a difficult leadership transition that founders often struggle with.
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.
Contradicting the common startup goal of scaling headcount, the founders now actively question how small they can keep their team. They see a direct link between adding people, increasing process, and slowing down, leveraging a small, elite team as a core part of their high-velocity strategy.
Gamma's CEO resists the pressure to scale headcount aggressively, arguing that doubling the team size does not guarantee double the speed. He believes a smaller, more agile team can change direction faster, which is more valuable than raw speed in a rapidly evolving market.
Despite success, founder Kevin Wagstaff felt like an "imposter" as the company scaled beyond $10M ARR. He recognized his strengths were in the early, scrappy "bias to action" phase, not managing a larger organization. He proactively brought in a seasoned CEO better suited for the next stage of growth.
Many entrepreneurs love their core business but lose motivation as their role expands to include responsibilities they dislike (e.g., finance, operations). The solution is to reinvest early profits into hiring employees to handle these tasks, freeing the founder to focus on their strengths and passions.
As companies grow from 30 to 200 people, they naturally become slower. A CEO's critical role is to rebuild the company's operating model, deliberately balancing bottom-up culture with top-down strategic planning to regain speed and ensure everyone is aligned.
Social media's "highlight reels" create pressure to build massive companies. Instead of chasing vanity metrics, owners should define what success looks like for them personally. A profitable company that affords a great life is often a better goal than a stressful, high-growth venture that doesn't align with your values.
