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

I'm Not on the Witness Stand, or Putting a Colleague on the Witness Stand

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i'm glad there's different people running these experiments at scale, like brian armstrong or toby lukey. But from a cultural standpoint, i do think that they're a this whole,. Like, i'm just seeing it manifest itself in all my companies in some way, shape or form. And so i understand where people are coming from in their frustrations with this as knlo. The problem is, and as every so knows, the problem is, there's always a next thing you're not doing.

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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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.