[{"@context":"https:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/blog.terabox.com\/insights\/dick-costolo-twitter-ceo-scaling-lessons#BlogPosting","mainEntityOfPage":"https:\/\/blog.terabox.com\/insights\/dick-costolo-twitter-ceo-scaling-lessons","headline":"Scaling Twitter: Dick Costolo\u2019s Management Masterclass","name":"Scaling Twitter: Dick Costolo\u2019s Management Masterclass","description":"\ud83d\udcfa Today’s recommended deep-dive video: https:\/\/www.youtube.com\/watch?v=Kw5hhIsw-wQ The Adult in the Room: Dick Costolo on Scaling Twitter\u2019s “Drama Queen” EraFrom Consensus Chaos to Execution VelocityThe Art of Scaling CommunicationHard Decisions: People, Competition, and RegretsKey TakeawaysQ&A The Adult in the Room: Dick... ","datePublished":"2026-06-30","dateModified":"2026-06-30","author":{"@type":"Person","@id":"https:\/\/blog.terabox.com\/author\/flextech-admin\/#Person","name":"flextech-admin","url":"https:\/\/blog.terabox.com\/author\/flextech-admin\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/ad516503a11cd5ca435acc9bb6523536?s=150&d=mm&r=gforcedefault=1","url":"https:\/\/secure.gravatar.com\/avatar\/ad516503a11cd5ca435acc9bb6523536?s=150&d=mm&r=gforcedefault=1","height":96,"width":96}},"publisher":{"@type":"Organization","name":"terabox","logo":{"@type":"ImageObject","@id":"http:\/\/blog.terabox.com\/wp-content\/uploads\/2021\/11\/logo\u4ea7\u54c1\u540d-\u7ad6\u7248.png","url":"http:\/\/blog.terabox.com\/wp-content\/uploads\/2021\/11\/logo\u4ea7\u54c1\u540d-\u7ad6\u7248.png","width":900,"height":900}},"image":{"@type":"ImageObject","@id":"https:\/\/img.youtube.com\/vi\/Kw5hhIsw-wQ\/maxresdefault.jpg","url":"https:\/\/img.youtube.com\/vi\/Kw5hhIsw-wQ\/maxresdefault.jpg","height":"","width":""},"url":"https:\/\/blog.terabox.com\/insights\/dick-costolo-twitter-ceo-scaling-lessons","video":{"@context":"http:\/\/schema.org\/","@type":"VideoObject","@id":"https:\/\/www.youtube.com\/watch?v=Kw5hhIsw-wQ#VideoObject","contentUrl":"https:\/\/www.youtube.com\/watch?v=Kw5hhIsw-wQ","name":"Twitter Ex-CEO Dick Costolo: The Operator's Case Against Founder Mode","description":"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.\n\n\nWe get into how he killed group decision-making and replaced it with what he calls \"bias to yes\"\u2014only 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.\n\nDick 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.\nIf you're scaling past 150 people and feeling the organizational barnacles build up, this one's for you.\n\n00:00 Introduction \n02:54 Joining as COO\n05:43 Boardroom Chaos\n07:58 Speed and Bias to Yes\n19:34 Scaling Communication\n33:07 Tough Feedback No Fluff\n35:41 Recruiting And Promotions\n41:07 Hypergrowth Hiring And Firing\n44:55 Competing And Big Regrets\n49:12 Moderation Press And CEO Playbook","thumbnailUrl":["https:\/\/i.ytimg.com\/vi\/Kw5hhIsw-wQ\/default.jpg","https:\/\/i.ytimg.com\/vi\/Kw5hhIsw-wQ\/mqdefault.jpg","https:\/\/i.ytimg.com\/vi\/Kw5hhIsw-wQ\/hqdefault.jpg","https:\/\/i.ytimg.com\/vi\/Kw5hhIsw-wQ\/sddefault.jpg","https:\/\/i.ytimg.com\/vi\/Kw5hhIsw-wQ\/maxresdefault.jpg"],"uploadDate":"2026-05-07T12:00:39+00:00","duration":"PT1H6M45S","embedUrl":"https:\/\/www.youtube.com\/embed\/Kw5hhIsw-wQ","publisher":{"@type":"Organization","@id":"https:\/\/www.youtube.com\/channel\/UCWrF0oN6unbXrWsTN7RctTw#Organization","url":"https:\/\/www.youtube.com\/channel\/UCWrF0oN6unbXrWsTN7RctTw","name":"Sequoia Capital","description":"Sequoia helps daring founders build legendary companies from idea to IPO and beyond. We aim to be the first true believers in tomorrow\u2019s most consequential companies. We partner with a few outliers each year and go all-in, providing them with the hands-on help required at every stage of the company building journey. Our expertise comes from nearly 50 years of working with legendary founders like Steve Jobs, Elon Musk, Larry Page, Jan Koum, Brian Chesky, Tony Xu, Lin Qiao, Eric Yuan, Christina Cacioppo, and Patrick Collison. In aggregate, Sequoia-backed companies account for more than 30% of NASDAQ's total value. The vast majority of the money we invest has been on behalf of nonprofits and schools like the Ford Foundation, Mayo Clinic and MIT, which means most of the returns we generate benefit these great causes.\n\n","logo":{"url":"https:\/\/yt3.ggpht.com\/uCN-D7KzMQY-Ti-xTsNAwilXVFFMYjEBRju_mXrR22HUYxJZjVZgP_SnamO9KbPo2XN-nE3O-A=s800-c-k-c0x00ffffff-no-rj","width":800,"height":800,"@type":"ImageObject","@id":"https:\/\/www.youtube.com\/watch?v=Kw5hhIsw-wQ#VideoObject_publisher_logo_ImageObject"}},"potentialAction":{"@type":"SeekToAction","@id":"https:\/\/www.youtube.com\/watch?v=Kw5hhIsw-wQ#VideoObject_potentialAction","target":"https:\/\/www.youtube.com\/watch?v=Kw5hhIsw-wQ&t={seek_to_second_number}","startOffset-input":"required name=seek_to_second_number"},"interactionStatistic":[[{"@type":"InteractionCounter","@id":"https:\/\/www.youtube.com\/watch?v=Kw5hhIsw-wQ#VideoObject_interactionStatistic_WatchAction","interactionType":{"@type":"WatchAction"},"userInteractionCount":66414}],{"@type":"InteractionCounter","@id":"https:\/\/www.youtube.com\/watch?v=Kw5hhIsw-wQ#VideoObject_interactionStatistic_LikeAction","interactionType":{"@type":"LikeAction"},"userInteractionCount":101}]},"about":["\u300eEnglish\u300f","Insights"],"wordCount":1477},{"@context":"https:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"name":"Insights","item":"https:\/\/blog.terabox.com\/insights\/#breadcrumbitem"},{"@type":"ListItem","position":2,"name":"Scaling Twitter: Dick Costolo\u2019s Management Masterclass","item":"https:\/\/blog.terabox.com\/insights\/dick-costolo-twitter-ceo-scaling-lessons#breadcrumbitem"}]}]