Matt recounts how Blue Tokai started with no formal plan, a tiny tabletop roaster and a belief that Indian consumers would eventually crave specialty coffee. The founders convinced local growers to sell export‑grade beans, proved the market was ready, and grew from a bedroom operation to a multi‑city chain.
Brian shares his framework for evaluating successful CEOs, emphasizing lovability, obsession, chip-on-shoulder mentality, deep knowledge, and being a perpetual student. This reflects the evolving nature of leadership in fast-moving industries.
Brian identifies giving direct feedback as the most critical yet underdeveloped skill in young founders, sharing frameworks to make difficult conversations more natural and effective.
Brian reflects on the psychological toll of building HubSpot over two decades, offering unvarnished perspective on the sacrifices required to build a lasting company.