Summary of EP 32: Former Twitter CEO Dick Costolo On Time at Second City, Running Twitter & Missing Out on IG

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00:00:00 - 01:00:00

In this interview, former Twitter CEO Dick Costolo discusses his time at Second City, his thoughts on improv, and his experiences with running Twitter. He shares his regrets about not buying Instagram and Vine when they were available, and talks about the challenges of running a social media company.

00:00:00 The host of the Cartoon Avatars show talks about their experience interviewing former Twitter CEO Dick Costolo. Costolo is a humorous and witty individual who shares interesting anecdotes from his time at Second City, working at Twitter, and missing out on Instagram. Bartlett says that Costolo is a great interviewee and that his ability to recall distinct memories from his past makes his interviews interesting to listen to. Bartlett says that he has never been beholden to anyone who has demanded he edit their interviews, and that he has never had to cut a snippet from an interview because someone requested it.
00:05:00 In this video, former Twitter CEO Dick Costolo discusses his time at Second City, running Twitter, and missing out on Instagram. He jokes about how he once pretended to commit to a college football recruit on social media, and discusses his recent wedding. He says that he will take off next week to attend the wedding.
00:10:00 Dick Costolo served as the CEO of Twitter from 2010 until 2014. He discusses his background, his time as CEO, and his thoughts on the company. Costolo also discusses his experiences with Second City and how he and Steve Carell became friends while at the training center.
00:15:00 Corel shares his story of how he became friends with Dick Costolo, how he found success in his career, and how Second City shaped his mindset and approach to startups. He also talks about how SNL helped him break into the acting world and the importance of networking.
00:20:00 This YouTube video features former Twitter CEO Dick Costolo discussing his time at Second City and his experiences with improv. Costolo says that the people who are good improvisers are not planning ahead and are simply in the moment. He also talks about the close call he had with SNL and Mad TV, and how he eventually got cast on SNL.
00:25:00 The video features former Twitter CEO and Second City alum, Dick Costolo, discussing his career path and how it crossed paths with EV Williams. Costolo emphasizes that it was luck that he was reacquainted with Williams when he left Google, as Audio was not quite ready for prime time.
00:30:00 Twitter CEO Dick Costolo discusses the unique challenges of the social media platform, including trolling and anonymity. He believes that addressing these challenges would go a long way toward solving the platform's problems.
00:35:00 Dick Costolo discusses how social media platforms should be weighted differently, how suspensions and deletions can be problematic, and how notifications can be a hindrance to engagement on social media platforms.
00:40:00 Dick Costolo talks about his time as CEO of Twitter, his thoughts on Facebook, and his current role as advisor to a company that is doing well. He also shares his thoughts on monetization and says that while ad revenue is important, there are other ways to make money on a platform.
00:45:00 Dick Costolo, CEO of Twitter from 2011-2014, shares his regrets about not buying Instagram and Vine when they were available for sale, and his thoughts on Facebook's success. He also shares his experiences founding and running Saturn, a social media platform for high school students.
00:50:00 Dick Costolo, former Twitter CEO, discusses his time at Second City, running Twitter, and the missed opportunities he sees in the current social media landscape. He stresses the importance of communication and warns against over-reliance on technology.
00:55:00 Dick Costolo discusses his time as CEO of Twitter, the company's early days, and the challenges of running a company with no founder. He says that it was important for him to maintain the company'sbrand identity and to communicate with employees regularly.

01:00:00 - 01:35:00

Dick Costolo, the former CEO of Twitter, discusses his time at Second City and how it prepared him for his role as CEO. He also discusses how he missed out on the opportunity to join Instagram, and how running Twitter has been different than running other companies. Costolo shares how he has learned to balance work and personal life, and gives advice on giving tough feedback and managing by trying to be liked.

01:00:00 Dick Costolo shares how he avoided becoming overwhelmed by the role of CEO of Twitter, and how he advises other leaders. He also discusses Bill Campbell, a mentor and coach who advised Steve Jobs and others in Silicon Valley.
01:05:00 Dick Costolo, the former CEO of Twitter, gives advice on giving bad feedback, managing by trying to be liked, and being forthright with communication. He also credits his time at Second City with helping him develop his skills as a leader.
01:10:00 This YouTube video features former Twitter CEO Dick Costolo discussing how he prepares for firing employees. He discusses the importance of communication, noting that "if you can't tell the person you're firing this is hard for me too you know you can't do that totally horrible but it's just horrible it's like the worst day." Costolo also discusses how he manages to stay positive when giving tough feedback, and gives credit to former Twitter COO Ryan Sarber for upleveling the management style within the company.
01:15:00 Twitter CEO Dick Costolo discusses the importance of success and how it applies to both himself and the company. He also discusses the Marxist versus Darwinian management mindset.
01:20:00 Dick Costolo discusses running Twitter, missing out on Instagram, and the challenges of maintaining culture while running a company. He emphasizes the importance of communication and the need to be willing to listen to others, even if they disagree with you.
01:25:00 Dick Costolo discusses his time at Twitter, his resignation from the board, and his thoughts on Jack Dorsey's tenure as CEO. Costolo believes that Dorsey is testing Twitter's boundaries, and that the company will likely fracture due to the tension between its former CEO and new CEO.
01:30:00 Dick Costolo, former CEO of Twitter, discusses his time at Second City and his thoughts on running Twitter. He also discusses the importance of having a Mission and a vision for a company, and warns listeners about the dangers of falling into a "Echo Chamber" of sameness.
01:35:00 Dick Costolo, the former CEO of Twitter, discusses his time at Second City and how he missed out on the opportunity to join Instagram. He also discusses how running Twitter has been different than running other companies and how he's learned to balance work and personal life.