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

The Logan Bartlett Show

Is He Really Trying to Get Away From Twitter?

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i don't really have any idea whether that's true or not. But it feels like, that feels like where we are. It's just a strange juxteposition of the person you see in private verses the person you seeing on twitter. Ye. Here's somthing imean wil talk about right into the right into the fire. Ernestl wite, gladly for his prak who woke up as c eo of the company in his first c o rol,. and is dealing with one of the weirdest situations in corporate america in the last hundred years.

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

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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, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.