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Sky Dylan Dayton (born August 8, 1971) is an American entrepreneur and investor. He is the founder of Internet service provider EarthLink, co-founder of eCompanies, the founder of Boingo Wireless, and co-founder of City Storage Systems and CloudKitchens.
At the age of 9, he got his first computer, a ZX81, which he used to learn programming in BASIC. At 16, Dayton graduated from The Delphian School, a private boarding school in Oregon, which uses study methods developed by Scientology founder L. Ron Hubbard. He wanted to be an animator but was rejected when he applied to CalArts (the California Institute of the Arts), saying he was too young at the time. Instead, Dayton got an entry-level job at a Burbank, California, advertising firm and three months later headed the graphics department. He moved to a larger advertising agency, Mednick & Associates, where he held a similar role until he was 18.Bloom, David (June 9, 1998), "Electronic Midas Touch", Los Angeles Daily News"Interview: Boingo Wireless Chairman Sky Dayton". (June 1, 2010). Los Angeles Daily News.
In 1993, after initially having great difficulties getting his Macintosh computer to access the Internet, Dayton said that he realized the Internet was likely to become the next mass communications medium. In an article in Vanity Fair, Dayton described his earliest interest in the Internet and its business potential:Keenan Mayo and Peter Newcomb (July 2008) An Oral History of the Internet Vanity Fair
EarthLink started in a small office of in Los Angeles, California. By the summer of 1995, EarthLink reached an agreement with UUNET allowing it to provide service nationwide. In 1995, Dayton introduced the first flat-rate service, at a time when AOL was still charging by the hour. By 1996, the company was growing at a rate of 5–10% a week. Dayton transitioned his title from founding CEO to executive chairman, handing over day-to-day operations of the company to Garry Betty. A long-time Mac user, Dayton led the creation of a strategic partnership with Steve Jobs at Apple in 1998 that made EarthLink the default ISP pre-loaded on the iMac.Apple, Inc. press release (August 1998), " Apple Selects EarthLink as ISP". This arrangement led to a $200 million investment by Apple in EarthLink.Menn, Joseph (January 2000). " Apple Buys $200 Million Stake in EarthLink". Los Angeles Times. EarthLink became the second largest U.S. Internet service provider, after AOL, with more than four million customers and over $1 billion in annual revenue.
He formed eCompanies, an incubator and venture capital fund for developing Internet companies, with former Disney Internet chief Jake Winebaum. A privately held company, eCompanies successfully launched LowerMyBills.com, which was purchased by Experian in 2005 for $380 million and EA Mobile, which went public and was then purchased by Electronic Arts in 2005 for $680 million. Dayton and eCompanies made headlines by buying the Business.com domain name for $7.5 million in 1999, believed to be the highest price ever paid for a domain at the time, during the height of the dot com bubble; they later sold the Business.com search portal to RH Donnelly in 2007 for $345 million.
In 2001, Dayton started Boingo Wireless to address what he saw as a fragmentation problem inherent in Wi-Fi networks. Boingo aggregates Wi-Fi hotspots around the globe into a single network, and has grown into one of the largest Wi-Fi operators. Boingo filed for its IPO in January 2011,Kim, Ryan (January 14, 2011), " While Everyone Watches Groupon, Boingo Files for IPO" GigaOm listing Dayton as owning 15% of the company. Boingo S-1 filing (Jan 14, 2011), SEC On May 4, 2011, Boingo Wireless went public selling 5,770,000 shares at $13.50, raising $77.9 million. Dayton served as Boingo's chairman until August, 2014.
In 2005, Dayton became CEO of Helio, a mobile phone joint venture of EarthLink and SK Telecom, formed with $220 million in funding from each company. At that time, Dayton resigned as chairman of EarthLink but remained a director. In January 2008, he was appointed Chairman of Helio's board of directors for the months leading up to Helio's acquisition by Virgin Mobile USA in June, 2008.
He is an investor in and board member of Diffbot, a Semantic Web and structured data startup, and Artsy, an online art marketplace, which raised a reported $50 million in July 2017.
Dayton was an early investor in video doorbell company Ring, which was acquired by Amazon in February, 2017 for $1 billion.
He is an investor in Joby Aviation, a NASA LeapTech participant building an electric VTOL, which raised $100 million from Intel, JetBlue and Toyota in February, 2018 and went public in August 2021, at a value of $6.6 billion.
Dayton is a co-founder of City Storage Systems and CloudKitchens, a ghost kitchen and technology company, which in March 2018, secured a $150 million investment from Uber founder Travis Kalanick, who also joined the company as its CEO. CloudKitchens' valuation in January 2019 was $5 billion; in November 2021, it reached $15 billion. In February 2019, Kalanick announced plans to expand into China. Kalanick remains actively involved in CloudKitchens, shaping the company's long-term strategy. CloudKitchens has grown from a handful of sites to an international operation spanning the United States, Latin America, and Europe. Other early investors in CloudKitchens include Jason Calacanis and Chamath Palihapitiya.
City Storage Systems, the parent company of CloudKitchens, buys "distressed" properties and converts them into spaces equipped for online retail, specifically food delivery.
In January 2019, Dayton led the Series A investment in micro satellite startup Swarm Technologies, along with PayPal co-founder David Sacks. About the investment, Dayton said, “Swarm’s approach reminds me of the early years at EarthLink—stay super scrappy, serve customers and generate revenue quickly.” Swarm was acquired by SpaceX in August 2021, in a transaction described as "a rare deal by Elon Musk’s space company that expands the team — and possibly the technological capabilities — of its growing Starlink internet service."
Dayton is a jet-rated pilot and has taken a personal and a business interest in improving pilot training and aviation safety. In December 2022, Dayton invested in Loft Dynamics. The Swiss startup creates virtual reality simulation technology for pilots, and raised $20 million in funding from venture capital firms including Sky Dayton, Craft Ventures, which Dayton runs with co-investors David Sacks, Bill Lee, and Jeff Fluhr, and Up Ventures.
In July 2025, satellite firm Xona Space Systems received $92 million in new funding for its fleet of positioning satellites, including its Series B round led by Craft Ventures. Dayton will join Xona's board as part of the new funding.
In 2011, he co-hosted an event to support then Deputy Mayor and Independent candidate Austin Beutner in the 2013 Los Angeles mayoral election.
In 2007, Dayton served on the advisory board of the Center for Public Leadership at the John F. Kennedy School of Government at Harvard University.
Dayton is married to novelist Arwen Elys Dayton. They have three children and live in the Pacific Northwest.Dayton, Sky. Bio on personal website."Interview: Boingo Wireless Chairman Sky Dayton". (June 1, 2010). Los Angeles Daily News.
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