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.
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The founder received harsh 360 feedback, with colleagues labeling him 'Hurricane Ben' for his disruptive behavior. Instead of being defensive, he recognized the feedback as a critical inflection point, forcing him to fundamentally change his leadership style to effectively scale with the company.
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.
Contrary to conventional wisdom about delegation, the best management style for a small business founder is to be "all over fucking everything all the time." This means maintaining granular involvement in every aspect of the company—from client happiness to legal spending—to relentlessly drive daily improvements and maintain operational control.
David Vélez found that adopting big-company management practices made Nubank feel like a big company, killing its startup urgency. The goal is not to become a traditional CEO, but to pair a founder's vision with light processes and a strong, agile team.
Amplitude's CEO describes the painful transition from founder (running to the hardest problem) to large-company executive. The latter role requires embracing hierarchy, saying "no" to most things, and managing through leverage rather than direct contribution—a skill set many founders resist and fail to learn.
While founder-led accountability is crucial, it's often misinterpreted. Leaders adopt a caricature of decisiveness, like mimicking Steve Jobs' harshness, which leads to micromanagement and alienates talented individual contributors who are key to scaling.
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.
Flexport's founder details his journey from a hands-off "manager mode" to a directive "founder mode." The rise of bottom-up AI innovation in hackathons is causing him to cycle back, recognizing the need to balance top-down strategy with empowering creative, decentralized ideas that leadership couldn't have conceived.
A founder's role is constantly changing—from individual contributor to manager to culture builder. Success requires being self-aware enough to recognize you're always in a new, unfamiliar role you're not yet good at. Sticking to the old job you mastered is a primary cause of failure to scale.
Bumble's founder believes the initial, all-consuming obsession is critical for getting a startup off the ground. However, this same intensity becomes a liability as the company matures. Leaders must evolve and create distance to gain the perspective needed for long-term growth and to avoid stifling opportunity.
