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.
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Contrary to the popular belief that successful, high-growth startups are constantly fielding acquisition offers, HubSpot's Brian Halligan reveals they received fewer than five serious inquiries over 18 years. This reality check suggests that a quiet phone is normal, even for category-defining companies.
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.
A founder's unhappiness often arises from a disconnect between their core values and the values the company is forced to project, leading to inauthenticity. The founder's ultimate power is the ability to reset the company's culture and policies to realign with their own principles, restoring personal drive.
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 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.
Conventional advice about work-life balance to avoid burnout is counterproductive for founders with extreme ambitions. Building a massive, venture-scale company requires a level of obsessive focus and sacrifice that is inherently unbalanced. For this specific phase of life, prioritizing the company above all else is necessary for success.
Contrary to the belief that success is measured by rapid email responses, the most important people for a founder to be responsive to are their own team. Prioritizing internal communication channels like Slack over an external email inbox ensures the team has the support it needs to execute effectively.
Founders often see franchising as a way to scale without managing more employees. However, it shifts the people problem to managing franchisees. This requires enforcing brand standards and managing underperformers who are also business owners, a group that can consume 80% of your time.
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.
Contrary to the "grow at all costs" mindset, early inefficiencies become permanently embedded in a company's culture. To build a truly scalable business, founders must bake in efficiency from day one, for example by perfecting the sales playbook themselves before hiring a single salesperson to avoid institutionalizing bad habits.
