Dick Costolo

Dick Costolo
Costolo in 2010
Dick Costolo
Born	Richard William Costolo 10 9, 1963
Birthplace	Royal Oak, Michigan, U.S.
Nationality	American
Occupation	Business executive, investor
Title	Partner, Index Ventures
Known for	CEO of Twitter (2010–2015)

Richard William Costolo (born September 10, 1963) is an American business executive, entrepreneur, and investor who served as the chief executive officer (CEO) of Twitter, Inc. from 2010 to 2015. Before ascending to the top role, Costolo served as Twitter's chief operating officer (COO), having joined the company in 2009. During his tenure as CEO, Costolo oversaw Twitter's transformation from a fast-growing startup into a publicly traded company, guiding it through its initial public offering (IPO) in November 2013. Born and raised in Michigan, Costolo built a career in technology entrepreneurship before joining Twitter, having previously co-founded multiple companies, including FeedBurner, which was acquired by Google in 2007. After stepping down from Twitter in 2015, Costolo pursued new ventures in fitness technology and venture capital, becoming a partner at Index Ventures.

Early Life

Richard William Costolo was born on September 10, 1963, in Royal Oak, Michigan, a suburb of Detroit. He grew up in the Metro Detroit area during a period when the region's economy was closely tied to the American automotive industry. Before entering the technology sector, Costolo pursued an interest in improvisational comedy, performing with established comedy groups in Chicago. His background in improv would later become a noted aspect of his leadership style, with Costolo frequently citing the skills he developed in comedy — including quick thinking, adaptability, and audience awareness — as instrumental in his approach to business management and corporate leadership.

Costolo's transition from comedic performance to technology entrepreneurship represented an unconventional career path that distinguished him from many of his peers in Silicon Valley. The communication and presentation skills he honed on stage in Chicago's improv scene would later serve him in numerous contexts, from pitching to investors to addressing Twitter's global user base and navigating the company's complex relationships with advertisers, regulators, and the press.

Education

Costolo attended the University of Michigan, where he earned a Bachelor of Science degree in computer science. His technical education provided the foundation for his subsequent career in software development and technology entrepreneurship. The University of Michigan's computer science program exposed Costolo to the fundamentals of programming and systems design during the 1980s, a formative period in the growth of the personal computing industry. Costolo has been identified as an alumnus of the university in multiple professional and media profiles throughout his career.

Career

Early Ventures and FeedBurner

Before joining Twitter, Costolo established himself as a serial entrepreneur in the technology sector. He co-founded and led several companies, building a track record in the Chicago technology community. His most notable pre-Twitter venture was FeedBurner, a web feed management company that provided services for RSS and Atom feeds. FeedBurner became one of the leading platforms for managing and analyzing web content distribution. In 2007, Google acquired FeedBurner, a transaction that gave Costolo significant experience with a major technology company and established his reputation as a successful entrepreneur and operator.

Costolo's role as CEO of FeedBurner was frequently referenced in subsequent coverage of his career, particularly when he was appointed to senior positions at Twitter. His experience in building and scaling a technology startup, navigating an acquisition by one of the world's largest technology companies, and understanding the mechanics of web content distribution were seen as directly relevant to the challenges Twitter faced as a rapidly growing social media platform.

Twitter: Chief Operating Officer

In September 2009, Costolo joined Twitter as its chief operating officer (COO). At the time, Twitter was experiencing rapid growth in its user base but had not yet developed a sustainable revenue model. The appointment of Costolo, an experienced operator with a background in scaling technology companies, signaled the company's intent to professionalize its operations and begin the process of monetization. As COO, Costolo was responsible for overseeing the business side of Twitter's operations, including the development of advertising products and revenue-generating strategies.

Costolo's arrival at Twitter came during a period of significant internal change at the company. Twitter had already undergone multiple leadership transitions, and the addition of an experienced executive like Costolo was intended to bring stability and operational focus to the organization. His tenure as COO lasted approximately one year before he was elevated to the CEO role.

Twitter: Chief Executive Officer

In October 2010, Costolo was named CEO of Twitter, replacing co-founder Evan Williams in the role. The transition was framed as a natural progression, with Williams moving to a product-focused role and Costolo assuming full operational control of the company. Costolo's appointment was the latest in a series of leadership changes at Twitter, which had seen multiple individuals hold the CEO title in its relatively short history.

Building the Business

Under Costolo's leadership, Twitter undertook significant efforts to build its advertising business and develop revenue streams. The company introduced and expanded its promoted tweets, promoted trends, and promoted accounts products, creating a self-serve advertising platform that allowed businesses of all sizes to reach Twitter's growing user base. Costolo presided over a period of substantial revenue growth as the company moved from a pre-revenue startup to a business generating hundreds of millions of dollars annually.

Costolo also oversaw key product developments and strategic acquisitions during his time as CEO. In January 2013, Twitter launched Vine, a short-form video application that allowed users to create and share six-second looping video clips. Costolo himself posted one of the early video tweets using the Vine platform, demonstrating the product by sharing a video of making steak tartare. The acquisition and launch of Vine represented Twitter's efforts to expand beyond text-based content and compete in the growing mobile video space.

Initial Public Offering

Perhaps the most significant milestone of Costolo's tenure was guiding Twitter through its initial public offering on the New York Stock Exchange in November 2013. The IPO was one of the most anticipated technology offerings in years and attracted considerable attention from investors and the media. Twitter's successful debut on the public markets was seen as a validation of the company's business model and Costolo's leadership in building a viable commercial enterprise from what had begun as a simple microblogging service.

The IPO process required Costolo to engage extensively with Wall Street analysts, institutional investors, and financial regulators, drawing on his skills as a communicator and his credibility as a technology executive. The company's stock price rose significantly on its first day of trading, marking a successful launch for Twitter as a publicly traded company.

Public Policy and Government Engagement

During his tenure as CEO, Costolo engaged with various aspects of public policy and government affairs. In 2011, President Barack Obama appointed Costolo to the National Security Telecommunications Advisory Committee (NSTAC), an advisory group that provides recommendations to the president on telecommunications issues related to national security.

Costolo also navigated the complex intersection of technology, free speech, and government regulation. In October 2011, he addressed topics including privacy, free speech, and the company's relationship with major technology competitors in an interview with The Wall Street Journal.

In January 2012, during the protests against the Stop Online Piracy Act (SOPA) and the PROTECT IP Act (PIPA), when English Wikipedia and other major websites participated in a blackout to oppose the proposed legislation, Costolo and Twitter took a different approach. While Twitter expressed opposition to the bills, Costolo was critical of the blackout strategy employed by other sites, characterizing it as an approach he disagreed with while still opposing the underlying legislation.

Challenges and Criticism

Despite the successes during his tenure, Costolo faced mounting challenges in the latter years of his time as CEO. Twitter's user growth began to slow, raising concerns among investors and analysts about the platform's ability to expand its audience and compete with other social media services. The company's stock price, which had risen sharply after the IPO, declined as growth metrics disappointed Wall Street expectations.

One of the most persistent criticisms Costolo faced was Twitter's handling of harassment and abuse on the platform. In February 2015, an internal memo written by Costolo was leaked to the press. In the memo, Costolo took personal responsibility for the company's failures in addressing abuse, writing that "we suck at dealing with abuse and trolls on the platform and we've sucked at it for years." The memo acknowledged that the problem had resulted in the loss of users who had been driven away by abusive behavior and that the company had failed to act effectively despite being aware of the issue. Costolo stated that he was "ashamed" of the company's record on the matter and committed to making changes.

The candid acknowledgment of the abuse problem was notable for its directness, but it also underscored the scale of the challenge facing the platform. The issue of online harassment on Twitter would continue to be a major point of discussion long after Costolo's departure, becoming one of the defining policy challenges for the company and the broader social media industry.

Departure from Twitter

On June 11, 2015, Twitter announced that Costolo would step down as CEO, effective July 1, 2015. Co-founder Jack Dorsey was named interim CEO, marking his return to the leadership of the company he had helped create. Costolo's departure came after a prolonged period of pressure from investors and analysts concerned about the company's slowing growth and declining stock price. The transition was described by the company as a mutual decision between Costolo and the board of directors.

In the wake of his departure, Costolo was characterized by various media outlets as having overseen both significant achievements and unresolved challenges during his nearly five years as CEO. He had guided the company through its IPO and built a substantial advertising business, but had struggled to address the platform's user growth issues and its problems with harassment and abuse.

Following his departure as CEO, Costolo reportedly planned to step down from Twitter's board of directors as well, further distancing himself from the company he had led.

Post-Twitter Career

Fitness Technology Venture

After leaving Twitter, Costolo turned his attention to new entrepreneurial ventures. In January 2016, it was reported that Costolo was launching a fitness software startup, applying his technology expertise to the health and wellness sector. The move reflected Costolo's personal interest in fitness and his belief that technology could transform how people approach physical health and exercise. The venture represented a significant departure from social media, though it drew on Costolo's experience in building technology platforms and engaging users through digital products.

Venture Capital and Advisory Roles

Costolo also became active in the venture capital and startup advisory space following his departure from Twitter. He joined Patreon, a platform that allows creators to receive funding from their supporters, as a member of its board of directors in December 2015.

Costolo became a partner at Index Ventures, a venture capital firm with offices in San Francisco, London, and Geneva. In this role, Costolo leveraged his experience as a technology executive and entrepreneur to advise and invest in emerging technology companies. His transition to venture capital followed a path taken by many former technology CEOs who sought to apply their operational experience to identifying and supporting the next generation of startups.

Additionally, Costolo explored creative and media opportunities. In October 2015, it was reported that he was involved in developing content about the technology industry, drawing on his insider perspective on Silicon Valley culture.

Personal Life

Costolo has maintained a relatively private personal life despite his prominence in the technology industry. He is known for his interest in fitness and physical training, an interest that informed his decision to launch a fitness technology startup after leaving Twitter. His background in improvisational comedy, developed during his time in Chicago, has remained an important part of his public identity. Costolo has spoken publicly about how the principles of improv — including listening, adapting, and building on the contributions of others — have influenced his approach to business leadership and team management.

Costolo's ability to blend humor with executive leadership has been the subject of academic study. The Stanford Graduate School of Business developed a case study examining Costolo's use of humor to navigate hierarchical barriers, analyzing how his comedic background informed his leadership style and his ability to connect with employees, partners, and the public.

Recognition

During and after his tenure at Twitter, Costolo received recognition for his role in shaping one of the most influential social media platforms in the world. His appointment by President Obama to the NSTAC advisory committee in 2011 reflected his standing as a leader in the technology industry whose expertise was sought on matters of national security and telecommunications policy.

Costolo's career has been featured in interviews, profiles, and case studies by leading media and academic institutions. The Bessemer Venture Partners organization profiled Costolo in its "Wish I Knew" series, documenting his journey and the lessons he drew from his experience at Twitter. He has appeared at major industry events, including the Cannes Lions International Festival of Creativity, where he spoke about the role of social media in the marketing and advertising landscape.

His career trajectory — from improv comedian to serial entrepreneur to CEO of a major public technology company — has been cited as an example of the diverse paths that can lead to success in the technology industry. Costolo's willingness to publicly acknowledge failures, as demonstrated in his February 2015 memo about Twitter's abuse problems, was noted by commentators as an unusual display of transparency from a sitting CEO of a publicly traded company.

Legacy

Costolo's tenure as CEO of Twitter spanned a period of significant growth and transformation for both the company and the social media industry as a whole. He assumed leadership of Twitter when it was a private company with substantial cultural influence but limited revenue, and he departed having built it into a publicly traded corporation with a multi-billion-dollar market capitalization and a mature advertising business.

The challenges Costolo confronted — including slowing user growth, platform abuse, and the pressures of operating a public company — foreshadowed issues that would continue to define the social media industry for years after his departure. His public acknowledgment that Twitter had failed to adequately address harassment on its platform was an early moment of reckoning for the industry, predating broader conversations about the responsibilities of technology companies to moderate content and protect their users.

Costolo's post-Twitter career in venture capital and entrepreneurship reflected a broader trend of former technology executives transitioning to investor and advisor roles, using their operational experience to guide the next generation of technology companies. His involvement with Index Ventures and his board service at companies like Patreon positioned him as an active participant in the ongoing evolution of the technology ecosystem.

His career also served as a case study in the intersection of creative backgrounds and technology leadership. The connection between his improvisational comedy training and his executive style has been examined by business schools and media outlets, contributing to a broader conversation about the value of non-traditional skill sets in corporate leadership.