Dick Costolo
Richard William "Dick" Costolo (born September 10, 1963) is an American businessman and former CEO of Twitter from 2010 to 2015, leading the social media platform through its IPO and critical growth period. Before becoming Twitter CEO, Costolo had an unconventional path—he studied computer science at University of Michigan, performed stand-up comedy and improvisational comedy professionally in Chicago for several years, founded startups including FeedBurner (acquired by Google for $100 million), and served as Twitter's COO before becoming CEO. Under Costolo's leadership, Twitter went public in November 2013 at a $24 billion valuation, but his tenure was marked by struggles with user growth stagnation, persistent harassment problems on the platform, and inability to monetize Twitter's influence. He resigned in 2015 amid investor pressure, succeeded by co-founder Jack Dorsey. Costolo is married to Mia Costolo, whom he met in Chicago's improv comedy scene in the 1980s, and the couple has three children. After Twitter, he co-founded Chorus, a fitness technology company. His career from comedian to Twitter CEO exemplifies Silicon Valley's embrace of unconventional backgrounds, though his tenure also demonstrates that charisma and improvisational skills don't necessarily translate to solving complex platform governance and growth challenges.
Early Life and Education
Richard William Costolo was born on September 10, 1963, and grew up in the Detroit area of Michigan. He demonstrated aptitude for both technology and performance from an early age.
Costolo attended the University of Michigan, where he studied computer science. At Michigan in the early 1980s, computer science was still an emerging field, and Costolo gained programming skills that would later prove valuable in his technology career.
However, Costolo's interests extended beyond computers. He was involved in improv comedy at Michigan and became fascinated by performance. After graduating with a degree in computer science in 1985, Costolo made an unconventional choice—rather than immediately joining the technology industry, he moved to Chicago to pursue comedy.
Personal Life and Meeting Mia
Dick Costolo met Mia in Chicago's improv comedy scene in the mid-to-late 1980s. Mia was also involved in comedy and theater, and the couple connected over their shared love of performance and humor. Chicago's improv scene in the 1980s was vibrant, with theaters like Second City and ImprovOlympic (now iO Theater) producing future comedy stars.
Dick and Mia married, and the couple has three children together. Throughout Dick's career transitions—from comedy to technology consulting to startups to Twitter CEO—Mia provided stability and support. Friends describe their marriage as grounded in humor and mutual understanding developed during their comedy days.
The Costolo family has maintained relative privacy despite Dick's high-profile Twitter role. After leaving Twitter, Dick spoke more openly about balancing career demands with family, particularly during the stressful years leading Twitter through public markets while facing relentless criticism about the platform's problems.
The family resides in the San Francisco Bay Area, having moved there during Dick's technology career evolution.
Comedy Career (1985-1990)
After graduating from Michigan, Costolo spent several years in Chicago's comedy scene. He performed stand-up comedy and improvisational comedy at various venues, working to establish himself as a professional comedian.
Costolo studied improv at ImprovOlympic under legendary instructor Del Close, who taught improvisational techniques to numerous future comedy stars. The experience taught Costolo skills in thinking quickly, adapting to unexpected situations, reading audiences, and performing under pressure—skills that would later prove valuable in business.
However, by the late 1980s, Costolo recognized that making a sustainable living in comedy was extremely difficult. Only a tiny percentage of comedians achieve financial success. He decided to leverage his computer science degree and transition to technology, though his comedy experience influenced his communication style throughout his business career.
Early Technology Career (1990s)
Costolo began working in technology consulting, using his programming skills to build systems for clients. He worked at companies including Andersen Consulting (now Accenture), gaining experience in corporate technology.
In the late 1990s, as the internet was emerging, Costolo co-founded several startups:
SpyOnIt (1996): Costolo co-founded SpyOnIt, an early web monitoring service that tracked changes to websites and sent alerts. The company was later renamed Burning Door Networx and struggled to gain traction before shutting down.
FeedBurner (2004): Costolo co-founded FeedBurner with Eric Lunt, Steve Olechowski, and Matt Shobe. FeedBurner provided RSS feed management and analytics for bloggers and publishers. The service became popular among early bloggers and podcasters.
In 2007, Google acquired FeedBurner for approximately $100 million. Costolo joined Google as part of the acquisition, working on various projects including Google's PowerMeter energy monitoring initiative.
Twitter COO and CEO (2009-2015)
In September 2009, Dick Costolo left Google to join Twitter as COO. Twitter, founded in 2006, had grown rapidly but struggled with revenue generation, operational challenges, and management instability.
COO Role
As COO under then-CEO Ev Williams, Costolo focused on:
- Building Twitter's advertising platform
- Creating scalable business operations
- Improving monetization from essentially zero revenue
Costolo's efforts helped Twitter develop "Promoted Tweets" and other advertising products that would become the company's primary revenue source.
Becoming CEO
In October 2010, Twitter's board replaced Ev Williams with Dick Costolo as CEO. Williams remained chairman. The change reflected the board's belief that Twitter needed operational leadership to scale the business and prepare for an eventual IPO.
IPO Success
In November 2013, Costolo led Twitter through its IPO. Shares priced at $26 and surged to $44.90 on the first day, valuing Twitter at over $30 billion. The successful IPO validated Twitter's cultural importance and business potential.
Challenges and Struggles
However, Costolo's tenure faced significant problems:
User Growth Stagnation: After rapid growth, Twitter's user growth slowed dramatically. Monthly active users plateaued around 300 million, far below Facebook's billions. New users found Twitter confusing and struggled to build followings.
Harassment and Abuse: Twitter became notorious for harassment, death threats, and abuse directed at women, minorities, and public figures. Costolo struggled to address this without seeming to limit free speech, a core Twitter value.
Product Confusion: Twitter experimented with numerous features (Moments, Periscope acquisition, algorithmic timelines) but struggled to meaningfully improve the core product.
Monetization Challenges: While Twitter had cultural influence, translating that into advertising revenue proved difficult. Growth in revenue lagged user growth, and profitability remained elusive.
Competition: Newer platforms like Instagram and Snapchat attracted young users, while Facebook remained dominant.
Executive Turnover: Twitter went through numerous senior executives, suggesting management instability.
Stock Decline: After initial IPO enthusiasm, Twitter's stock declined as investors lost confidence in growth prospects.
Resignation
By early 2015, investor patience exhausted. Costolo faced pressure from the board and activist investors. In June 2015, he announced his resignation as CEO, with co-founder Jack Dorsey returning as CEO.
Costolo's departure ended a tumultuous five-year tenure. He had taken Twitter public and built its advertising business, but failed to solve fundamental product and growth challenges that would continue plaguing Twitter for years.
Post-Twitter Career
After leaving Twitter, Costolo took time off before co-founding Chorus, a fitness technology startup, in 2016. Chorus focused on connected fitness coaching, attempting to apply technology to personal training. However, Chorus remained relatively small-scale compared to Twitter.
Costolo also became involved in investing and advising startups, serving on various boards and making angel investments. His post-Twitter career has been quieter, suggesting he may prefer working on smaller ventures without the intense public scrutiny he faced at Twitter.
Net Worth
Dick Costolo's net worth is estimated at approximately $300-400 million, derived primarily from:
- FeedBurner acquisition proceeds
- Twitter stock compensation during his COO and CEO tenure
- Investments and advisory roles
Legacy
Dick Costolo's legacy at Twitter is mixed. He successfully led the company through its IPO and built its advertising business from essentially nothing to billions in revenue. However, he failed to solve Twitter's fundamental challenges around user growth, harassment, and product evolution. Whether these problems were solvable by any CEO or represented Costolo's specific failures remains debated—Jack Dorsey and subsequent CEOs faced similar struggles.
Costolo's path from comedian to Twitter CEO demonstrates Silicon Valley's openness to unconventional backgrounds. His improvisational skills helped him navigate unpredictable situations, though they couldn't solve structural platform challenges.