Surviving Twitter's Growing Pains: Ex-CEO Dick Costolo
In a Nutshell
Dick Costolo, Twitter's ex-CEO, shares a masterclass on scaling hypergrowth companies by accelerating decision velocity (e.g., "If it takes six weeks, how to make it two?"), replacing vague principles with DRIs (Directly Responsible Individuals) and bias-to-yes, and using management by walking around late nights to align teams and communicate context. He stresses pushing decisions down without "Dick said" excuses, giving blunt feedback (write it out, deliver unfluffed, sit in silence), strategic forestry management over firefighting, hiring/firing deliberately (slow hire, fast fire), and regrets like missing Instagram acquisition. Core lesson: Focus ruthlessly on few priorities, ensure everyone grasps the "why" and personal stakes, and lead authentically without copying archetypes like Jobs.
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Twitter was the drama queen of hyper growth companies. When Dick Costolo took over as CEO, the Twitter bird had hanged itself and exploded on two different magazine covers. He told head of communications Gabriel Stricker, "Great news. Next year's goal, no dead birds on magazine covers."
Dick Costolo was Twitter's third CEO: first Jack Dorsey, then Ev Williams. Costolo joined as COO then became CEO, running it for 5 years. Twitter created a category, grew extremely fast, but had no revenue model and was famously dysfunctional. Costolo acted as the adult in the room, running a scale-up CEO master class. Key topics: increasing velocity of decisions and execution as companies scale; management by walking around; giving tough feedback to tough people; dealing with press; focus in the AI era; managing the forest instead of fighting fires. Regrets include not acquiring Instagram.
Costolo joined in summer 2009 after selling FeedBurner to Google, where he reconnected with Twitter founders from Blogger preparing to start Odeo (which became Twitter). Ev Williams pitched him initially for interim COO during paternity leave, then permanent COO. Twitter had zero revenue model despite hype (Ashton Kutcher and Oprah Winfrey fighting for 1 million followers). Costolo saw it as a rocket ship opportunity.
Twitter was chaotic: decisions made collectively as a group (e.g., debating native retweet vs. manual RT). Things moved methodically and slowly. The process of pushing Ev out and installing Costolo as CEO was awful—happened super quickly yet slowly and painfully. Costolo was informed in driving rain on the road home by Evan and Jason that the board decided he should be CEO. Bill Campbell called advising him to quit. Board reversed, then invested in his options and suggested he leave. Over days and weeks, Bjan Sabay from Spark texted him not to quit. Finally, board insisted he take CEO role.
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