Surviving Twitter's Growing Pains: Ex-CEO Dick Costolo

Dick Costolo took over as CEO of Twitter in 2010, inheriting what he calls "the drama queen of hypergrowth companies." Hired as the adult in the room behind founders Jack Dorsey and Ev Williams, Dick spent five years dragging Twitter from a chaotic collective into a public company, and learned a scale-up CEO playbook in the process. We get into how he killed group decision-making and replaced it with what he calls "bias to yes"—only your direct manager can tell you no. Why he stopped solving problems with processes ("the launch checklist was 17 pages long") and started solving them with DRIs and operating control. How he managed by walking around the engineering floor at 9:30 PM to figure out what was actually getting built. And the Steve Jobs trick he stole from Pixar for finding out what's really going on inside a team. Dick is candid about the misses, too, including trying to buy Instagram for around $700 million before Facebook did, and his own struggles to fire fast. When I was running HubSpot, I fired slow almost every time and regretted it. Dick did better, but he'll tell you it never gets easier. If you're scaling past 150 people and feeling the organizational barnacles build up, this one's for you. 00:00 Introduction 02:54 Joining as COO 05:43 Boardroom Chaos 07:58 Speed and Bias to Yes 19:34 Scaling Communication 33:07 Tough Feedback No Fluff 35:41 Recruiting And Promotions 41:07 Hypergrowth Hiring And Firing 44:55 Competing And Big Regrets 49:12 Moderation Press And CEO Playbook

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