My First Million 7 Brutal Questions for a $20B Founder
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Dec 26, 2025 
Brian Halligan, Co-founder and former CEO of HubSpot, shares his entrepreneurial journey and insights on scaling companies. He discusses the emotional rollercoaster of building a startup, including the reality of imposter syndrome. Halligan explains HubSpot's unique 'pothole report' process to learn from mistakes and emphasizes the importance of maintaining a risk-seeking culture as companies grow. He predicts that while AI might seem like a bubble now, strong players will emerge, making it an exciting time for new entrepreneurs.
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CEO Market Fit Varies With Scale
- Brian Halligan felt highest CEO 'fit' between 10 and 1,000 employees where work matched his strengths and energized him.
- Beyond ~1,000 employees he found the job less enjoyable because he worked on things he cared less about.
Founders Live In A Problem-Heavy Loop
- Founders live in a feedback loop of mostly problems with rare big wins, which keeps them constantly anxious.
- That pessimistic stance may correlate with entrepreneurial persistence and drive.
Support Promos Created A Predictable Pothole
- HubSpot promoted many top-tier support hires into other roles and then understaffed support, raising wait times to 20 minutes.
- That predictable 'pothole' led them to create a formal postmortem process to prevent repeats.