Published Feb 12, 2018

20VC: Dick Costolo on The Balance of Vision and Realism in Startups, The Biggest Challenge in Scaling Twitter & How To Optimise Decision Making Internally

Dick Costolo, former CEO of Twitter, delves into the blend of improvisation and entrepreneurship, shares how to balance vision with realism, and discusses the leadership hurdles in scaling Twitter, including managing global expansion and decision-making.

Episode Highlights

Topics covered

Episode Highlights

Related Episodes

20VC: Twitter Co-Founder Biz Stone on The 3 Stages of Wealth, The Return To Twitter in 2017 and the Associated Missions and Challenges & Why Silicon Valley is not an "Insiders Only" Universe?
Answers 383 questions
20VC: Biggest Lessons and Challenges Building One of the Most Successful Seed Funds, How To Manage Investor Psychology, Self-Doubt and Insecurity & The Secret to Truly Successful Venture Partnerships with David Frankel, Co-Founder @ Founder Collective
Answers 383 questions
20VC: Whoop Founder, Will Ahmed on How CEOs Can Perform at their Highest Level, Why There is Value in Struggle Early On, Why Realism is Overrated in Startups and How To Create a Culture of Delegated Decision-Making
Answers 383 questions
20VC: Why Financial Planning and Goals Do Not Work, The Decision to Ban Politics in the Workplace and Losing 1/3 of the Team Overnight & The One Question That Will Drive All Decision-Making for Leaders with Jason Fried, CEO @ 37Signals
Answers 383 questions
20VC: The Biggest Indicators Of Success In Founding Teams, How To Balance Both Vision and Operations & Taking Money From "The Man At The Rug Store" with Mar Hershenson, Founding Managing Partner @ Pear.vc
Answers 383 questions
20VC: Do VC's Really Hustle Enough? The Takeaways From Watching Twitter Scale From 30 to 2,500 & Why Chris Sacca Is Like Yoda with Ryan Sarver, Partner @ Redpoint
Answers 383 questions
20VC: Kevin Weil on The Biggest Lessons from Leading Product at Instagram and Twitter | How Working With Kevin Systrom Impacted His Approach To Product | 3 Things Instagram Did To Make Stories So Successful and Why Investing Makes Operators Better at Thei
Answers 383 questions
20VC: Basecamp Founder David Heinemeier Hansson on Why It Is The Biggest BS To Chase Being A Unicorn, His Relationship to Wealth and Status and Why Now More Than Ever It Is A Myth Entrepreneurs Have To Raise VC
Answers 383 questions
20VC: Biggest Lessons from Working with John Doerr, How Founders Can Have Discussions of Vulnerability with Their Board and Investors & Marrying Another Founder; The Pros, Cons and Ways To Make it Succeed with Alyson Friedensohn, Co-Founder & CEO @ Modern
Answers 383 questions
20VC: Atlassian Co-Founder Scott Farquhar on The Biggest Lessons Scaling Atlassian to $50BN Market Cap; The Four Roles of the CEO, The Funding Round That Net Accel $6BN, The Regrets of Omission and Commission & The Honeymoon Cut Short
Answers 383 questions
20VC: 3 Biggest Mistakes Founders Make When Scaling, Management 101 on Trust Building, Morale Maintenance and Hiring & What We Can Learn About Parenting From Nature Programs with Scott Dietzen
Answers 383 questions
20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff
Answers 383 questions
20VC: Crowdstrike Founder, George Kurtz on Scaling to a $60Bn Market Cap, How to Acquire and Retain the World's Best Talent & The Right Way to View Competition in Today's Market?
Answers 383 questions
20VC: Leadership Lessons from Bill Gates and Steve Ballmer, The Early Days of TheFacebook Advising Mark Zuckerberg and Why Now is Not the Right Time For Startups to Stockpile Cash with Hadi Partovi, CEO @ Code.org
Answers 383 questions
20VC: Techstars Founder David Cohen on Why Seed Investing Is A Different Asset Class To Venture, What Makes The Best And The Worst Board Members & Why Every Company Has To Have A Pessimist In The Room
Answers 383 questions

Dexa/Harry Stebbings

20VC: Dick Costolo on The Balance of Vision and Realism in Startups, The Biggest Challenge in Scaling Twitter & How To Optimise Decision Making Internally

Topics covered

Popular Clips

Building Groundswell Culture

From Programming to Comedy

Myth of Silicon Valley

Business Books

Coping with Pressure

Scaling Global Offices

Embracing Improvisation

Global Law Firm

Scaling Struggles

Mental Toughness and Resilience

Embracing Uncertainty

Board Management Insights

Balancing Vision and Realism

Building a Culture

Episode Highlights

Improv and Entrepreneurship

Founder's Mindset

Leadership Challenges

Related Episodes

20VC: Twitter Co-Founder Biz Stone on The 3 Stages of Wealth, The Return To Twitter in 2017 and the Associated Missions and Challenges & Why Silicon Valley is not an "Insiders Only" Universe?

20VC: Biggest Lessons and Challenges Building One of the Most Successful Seed Funds, How To Manage Investor Psychology, Self-Doubt and Insecurity & The Secret to Truly Successful Venture Partnerships with David Frankel, Co-Founder @ Founder Collective

20VC: Whoop Founder, Will Ahmed on How CEOs Can Perform at their Highest Level, Why There is Value in Struggle Early On, Why Realism is Overrated in Startups and How To Create a Culture of Delegated Decision-Making

20VC: Why Financial Planning and Goals Do Not Work, The Decision to Ban Politics in the Workplace and Losing 1/3 of the Team Overnight & The One Question That Will Drive All Decision-Making for Leaders with Jason Fried, CEO @ 37Signals

20VC: The Biggest Indicators Of Success In Founding Teams, How To Balance Both Vision and Operations & Taking Money From "The Man At The Rug Store" with Mar Hershenson, Founding Managing Partner @ Pear.vc

20VC: Do VC's Really Hustle Enough? The Takeaways From Watching Twitter Scale From 30 to 2,500 & Why Chris Sacca Is Like Yoda with Ryan Sarver, Partner @ Redpoint

20VC: Kevin Weil on The Biggest Lessons from Leading Product at Instagram and Twitter | How Working With Kevin Systrom Impacted His Approach To Product | 3 Things Instagram Did To Make Stories So Successful and Why Investing Makes Operators Better at Thei

20VC: Basecamp Founder David Heinemeier Hansson on Why It Is The Biggest BS To Chase Being A Unicorn, His Relationship to Wealth and Status and Why Now More Than Ever It Is A Myth Entrepreneurs Have To Raise VC

20VC: Biggest Lessons from Working with John Doerr, How Founders Can Have Discussions of Vulnerability with Their Board and Investors & Marrying Another Founder; The Pros, Cons and Ways To Make it Succeed with Alyson Friedensohn, Co-Founder & CEO @ Modern

20VC: Atlassian Co-Founder Scott Farquhar on The Biggest Lessons Scaling Atlassian to $50BN Market Cap; The Four Roles of the CEO, The Funding Round That Net Accel $6BN, The Regrets of Omission and Commission & The Honeymoon Cut Short

20VC: 3 Biggest Mistakes Founders Make When Scaling, Management 101 on Trust Building, Morale Maintenance and Hiring & What We Can Learn About Parenting From Nature Programs with Scott Dietzen

20VC: Lessons Scaling Insight Partners to a $20BN Latest Fund, The Two Biggest Learnings on Price, How to Manage and Train Young People in Venture, Why Business Classrooms Do Not Work and How to Assess the Two Commodities in Life; Money and Time with Jeff

20VC: Crowdstrike Founder, George Kurtz on Scaling to a $60Bn Market Cap, How to Acquire and Retain the World's Best Talent & The Right Way to View Competition in Today's Market?

20VC: Leadership Lessons from Bill Gates and Steve Ballmer, The Early Days of TheFacebook Advising Mark Zuckerberg and Why Now is Not the Right Time For Startups to Stockpile Cash with Hadi Partovi, CEO @ Code.org

20VC: Techstars Founder David Cohen on Why Seed Investing Is A Different Asset Class To Venture, What Makes The Best And The Worst Board Members & Why Every Company Has To Have A Pessimist In The Room

20VC: Dick Costolo on The Balance of Vision and Realism in Startups, The Biggest Challenge in Scaling Twitter & How To Optimise Decision Making Internally

Topics covered

Popular Clips

Episode Highlights

Improv and EntrepreneurshipDick Costolo, former CEO of Twitter and co-founder of Chorus, discusses the intersection of his comedy passion with his tech career. He highlights the role of improvisation in entrepreneurship and the importance of pursuing one's passions.

Improv and Entrepreneurship

Founder's Mindset

Leadership Challenges

Related Episodes