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
 

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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

 

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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.

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