EP 32: Former Twitter CEO Dick Costolo Talks About His Time at Second City, Running Twitter, and Missing Out on Instagram

In the 32nd episode of Cartoon Avatars former Twitter CEO Dick Costolo discusses his time at Second City with greats like Tina Fey, Amy Poehler, and Steve Carrell, successfully managing and running Twitter as a non-founder, and trying to buy Instagram. (0:00) Intro (0:58) Mark Cuban canceled (4:08) The editing room (6:07) Logan’s engagement (9:22) Welcome Dick Costolo (13:54) Dick’s time at Second City (28:16) After Second City (32:44) Why Twitter is a unique challenge (35:06) Treating all Twitter accounts equally (40:09) Social Media Regulation (42:06) Twitter monetization (44:06) Trying to buy Instagram (48:37) Social media platform Saturn (52:01) Expectation setting (57:10) Leading a company you didn’t found (59:53) Role vs identity (1:02:15) Bill Campbell’s mentorship (1:07:57) Letting people go (1:12:47) Successful managing (1:15:42) Marxist vs Darwinian management (1:19:13) Assume best intentions (1:24:40) Getting unfollowed by Elon Musk (1:30:31) Rapid fire (1:35:14) Outro   Mixed and edited: Justin Hrabovsky Produced: Andrew Nadeau and Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson   🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast... Spotify: https://open.spotify.com/show/5WqBqDb... Google Podcasts: https://podcasts.google.com/feed/aHR0...   Follow on Socials 📸 Instagram - https://instagram.com/cartoonavatars 🐦 Twitter - https://twitter.com/cartoonavatars 🎬 Clips on TikTok - https://www.tiktok.com/@cartoonavatars   About the Show A Saturday morning podcast hosted by Logan Bartlett (Partner and Managing Director at Redpoint Ventures) covering the tech news with his friends and other people with industry expertise. Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky   Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA   🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1   Follow on Socials   📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow   About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.