7 Brutal Questions for a $20B Founder

Brian Halligan, HubSpot's co-founder, discusses his entrepreneurial journey, happiness levels at different company sizes, and the emotional challenges of being a founder, including dealing with constant problems and existential threats. He shares insights on HubSpot's early days, the importance of sticking with it through setbacks, and the company's unique culture. Halligan also touches on current trends he observes at Sequoia, including the rise of AI-powered application companies and the qualities he looks for in founders, summarized by his "FLOC" rubric (First principled, Lovable, Obsessed, Knowledgeable). He reflects on his management style, the value of homegrown talent, and the need to maintain a risk-seeking appetite as companies grow, drawing parallels between Silicon Valley entrepreneurship and the marketing strategies of the Grateful Dead.