Published Sep 9, 2022

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

Explore the evolution of leadership and innovation as former Twitter CEO Dick Costolo delves into his transition from Second City's comedy stages to the helm of a social media giant, sharing candid perspectives on scaling challenges, missed opportunities with Instagram, and the vital role of empathy and communication in effective management.

Episode Highlights

Topics covered

Episode Highlights

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

Topics covered

Popular Clips

Scaling Challenges

Silicon Valley Humor

Assume Positive Intent

Corporate Mission Importance

Twitter Dynamics

Star Quality in Comedy

High EQ Insights

Delivering Tough Feedback

Career Crossroads

Key Insights

Comedy Origins

Effective Feedback Strategies

Behind the Interview

Edit Button Dilemma

Improv and Authenticity

Episode Highlights

Challenges of Scaling

Comedy Origins

Leadership Philosophy

Related Episodes

EP 12: Dan Primack Talks Musk/Twitter, Zach Weinberg Explains Founding a $2.1B Co & Owning Nightclub

EP 17: Benedict Evans on State of Tech, Alexis Gay on the Risk in Leaving it All Behind for Comedy

EP 14: Lux Capital’s Josh Wolfe Talks Musk, Adobe’s Scott Belsky Talks Twitter, Bolt & Breslow Again

EP 11: Elon Musk Buys 9.2% of Twitter, A Deep Dive Into Twitter History, The End of Fast, and More

EP 5: Coinbase Tweet Storm, Truth Social, Death of the Five Day Work Week and the ClearCo Breakup

Bonus Episode: The Elon Musk Twitter Saga

Best of: Our Favorite Interviews Featuring Mark Cuban, Parker Conrad, Dick Costolo and More

EP 13: Interview w/ Keith Rabois on Why He Tweets & Miami, Netflix Loses Subscribers, & More Elon

EP 39: All-In’s Jason Calacanis Joins, Breaking Into Media, Tech in Journalism and Kanye

Secrets of Silicon Valley from Solo Capitalist and the Worst Advice That Founders Get

EP 10: Interview with Ryan Breslow, The Silicon Valley Mob, Twilio Insider Trading and OnlyFans

Ep 42: Zach Weinberg Returns, His Take on FTX, Venture’s Culpability and Possible Death of Twitter

EP 35: NYT CEO Meredith Kopit Levien+ Bankless’ David Hoffman Crypto Debate Live@ Primary NYC Summit

EP 29: Multicoin Capital’s Kyle Samani Joins Crypto Debate & Chat Helium + Productivity at Big Tech

Silicon Valley Legend Unveils Her Best Operating Advice

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

Topics covered

Popular Clips

Episode Highlights

Challenges of ScalingDick Costolo shares insights into Twitter's unique business challenges and his attempt to acquire Instagram. He discusses the intricacies of scaling, monetization, and user management in the competitive social media landscape.

Challenges of Scaling

Comedy OriginsDick Costolo, former CEO of Twitter, reflects on his transformative experiences at Second City, where he honed his comedic skills alongside future stars. He discusses the unpredictable nature of success in comedy and how improv has shaped his approach to leadership and life.

Comedy Origins

Leadership PhilosophyDick Costolo, former Twitter CEO, shares his insights on effective management and leadership. He discusses the importance of communication, empathy, and the challenges of navigating social media regulation.

Leadership Philosophy

Related Episodes