Dick Costolo

Dick Costolo – Life, Career, and Notable Reflections

Learn about Dick Costolo (born September 10, 1963), the American technology executive who led Twitter as CEO from 2010 to 2015. Explore his background, entrepreneurial path, leadership highlights, challenges, and memorable quotes.

Introduction

Dick Costolo (full name Richard William Costolo) is a prominent American tech executive and entrepreneur best known for serving as CEO of Twitter, Inc. from 2010 until mid-2015. Under his leadership, Twitter navigated scaling challenges, monetization efforts, and public controversies over platform content. But Costolo’s life and path to tech leadership include surprising detours—from improv comedy to founding startups to confronting the complexities of online speech.

Early Life and Education

Costolo was born on September 10, 1963, in Royal Oak, Michigan (a suburb of Detroit). University of Michigan, where he earned a Bachelor of Science in computer and communication sciences in 1985.

While at the University of Michigan, Costolo took theater classes (to satisfy curriculum requirements), which awakened an interest in performance and improvisation. Chicago to pursue improv comedy.

The improv experience, though not sustained as a career, contributed to his ability to think on his feet, communicate, and navigate ambiguity—qualities which later would prove useful in leadership of fast-moving tech firms.

Entrepreneurial Path & Career Progression

Consulting & Early Tech Ventures

After his Chicago improv period, Costolo joined Andersen Consulting (now part of Accenture), where over about eight years he held senior roles in product and technology groups.

He then co-founded several ventures:

• Burning Door Networked Media, a web design and development consulting firm, which was acquired by Digital Knowledge Assets in October 1996.

• SpyOnIt, a web page monitoring service, which was sold to 724 Solutions in September 2000.

• FeedBurner, launched around 2004 (along with partners Eric Lunt, Steve Olechowski, Matt Shobe).

When Google acquired FeedBurner in 2007, Costolo joined Google, working in various capacities within the company.

Rise at Twitter

In September 2009, Costolo left Google to join Twitter as its Chief Operating Officer (COO).

In October 2010, during a paternity leave by then-CEO Evan Williams, Costolo stepped into the CEO role temporarily—but that arrangement became permanent.

Under his leadership, Twitter’s revenue and scale grew substantially.

On June 11, 2015, Twitter announced that Costolo would step down as CEO effective July 1, 2015, to be succeeded by Jack Dorsey (interim).

After leaving Twitter, Costolo remained active in the tech and startup ecosystems:

• He became a consultant for the HBO series Silicon Valley.

• He joined Index Ventures as a partner.

• He announced a fitness technology startup (called Chorus) in collaboration with Bryan Oki; the idea was to build a platform combining social, motivation, and fitness tracking to help users achieve goals.

• He also joined the board of Patreon (a platform supporting creators) in December 2015.

Leadership Challenges & Controversies

Costolo’s time as CEO was marked not only by growth but also by difficult trade-offs and public criticisms:

• In an internal memo that leaked in early 2015, Costolo admitted that Twitter had underperformed in dealing with harassment and trolling: “We suck at dealing with abuse and trolls on the platform and we’ve sucked at it for years.”

• He faced questions about the balance between free speech and content moderation, especially as Twitter’s role in global discourse expanded.

• In 2012, during the SOPA (Stop Online Piracy Act) controversy, Costolo publicly downplayed Wikipedia’s blackout protest: “That’s just silly. Closing a global business in reaction to single-issue national politics is foolish.”

• In 2014, Costolo revealed that he and Twitter staff had to contend with death threats from ISIS when Twitter shut down certain terror-group accounts.

• Later, in 2017, Costolo publicly expressed regret about not addressing bullying more effectively during his time at Twitter, acknowledging the complexity of the problem and saying he let it be sidelined relative to other priorities.

Notable Quotes

Here are a few statements attributed to Dick Costolo that reflect his thinking or public posture:

• “We’re the free speech wing of the free speech party.” — A well-known quote during his Twitter leadership.

• “We suck at dealing with abuse and trolls on the platform and we’ve sucked at it for years.” — candid internal acknowledgment.

• In the SOPA debate: “Closing a global business in reaction to single-issue national politics is foolish.”

• He has also emphasized the challenges of managing a platform at global scale, especially when actors use it maliciously (as seen in his remarks about ISIS threats)

Legacy, Influence & Reflections

Dick Costolo’s leadership period at Twitter sits at a pivotal moment in the evolution of social media: the phase when platforms moved from novelty to indispensable infrastructures of communication, politics, and culture. Under his tenure, Twitter attempted to build sustainable revenue models, expand its user base, and grapple publicly with content moderation and speech governance.

His path—from improv comedian to tech entrepreneur to high-profile CEO—underscores the unpredictable blends of creativity, risk, communication, and discipline required in tech leadership. His candid admissions about the platform’s limitations also contribute to ongoing debates about the responsibilities of social media platforms.

Costolo’s post-Twitter ventures (in fitness tech, venture capital, and supporting creator economies) show a willingness to pivot, experiment, and engage new challenges rather than rest on past success.