Sky Dayton

Dayton's father, Wendell Dayton, is a sculptor,[7] and his mother was a dancer and poet. Shortly after his birth in New York City, the family moved to Los Angeles. He lived for a time with his maternal grandfather, David DeWitt, an IBM Fellow, who played a large part in introducing Dayton to technology.[4][8]

At the age of 9, he got his first computer, a Sinclair 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 L. Ron Hubbard.[9][10] He wanted to be an animator but was rejected when he applied to CalArts (the California Institute for the Arts), saying he was too young at the time.[11] Instead, Dayton got an entry-level job at a Burbank, California, advertising firm and three months later headed the graphics department.[12] He moved to a larger advertising agency, Mednick & Associates, where he held a similar role until he was 18.[13][14]

Dayton started his first business in 1990 at age 19. He and a friend raised money from family and friends to open Mocha Gallery (later Cafe Mocha), an art gallery and coffee house in Los Angeles.[4][15][16] While managing Cafe Mocha, Dayton and friend Adam Wicks Walker opened Dayton/Walker Design in 1992, a Studio City advertising and design firm, serving entertainment clients including Fox Television, Disney, Columbia Pictures, Sony Pictures, and Warner Brothers.[14][17]

In 1993, after initially having great difficulties getting his Macintosh computer to access the Internet, Dayton said that he realized that the Internet was likely to become the next mass communications medium.[18] In an article in Vanity Fair, Dayton described his earliest interest in the Internet and its business potential:[19]

I heard about this thing called the Internet. I thought, That sounds kind of interesting. The first thing I did is I actually picked up the phone and dialed 411, and I said, I’d like the number for the Internet, please. And the operator is like, What? I said, Just search any company with the word Internet in the name. Blank. Nothing. I thought, Wow, this is interesting. What is this thing anyway?

— Sky Dayton

In 1994, Dayton founded EarthLink, an Internet service provider (ISP) that would offer Internet access to the public.[20] Kevin O'Donnell, father of a childhood friend, and Reed Slatkin became EarthLink's first financial backers.[15][16] Other investors followed, including Greg B. Abbott, former AT&T CFO Robert Kavner,[21] Chip Lacy, and eventually larger investors such as George Soros.[22]

EarthLink started in a small office of 600 square feet (56 m²) in Los Angeles, California. By the summer of 1995, EarthLink reached an agreement with UUNET allowing it to provide service nationwide. 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 Charles "Garry" Betty.[22] 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.[23] This arrangement led to a $200 million investment by Apple in EarthLink.[24] EarthLink grew to become the second largest U.S. Internet service providers, after AOL, with more than four million customers and over $1 billion in annual revenue.[25][26]

In June 1999, Dayton's title changed again, this time to non-executive chairman of EarthLink. He formed eCompanies, an incubator and venture capital fund for developing Internet companies, with former Disney Internet chief Jake Winebaum.[4] A privately held company, eCompanies successfully launched LowerMyBills.com, which was purchased by Experian in 2005 for $380 million and JAMDAT Mobile, which went public and was then purchased by Electronic Arts in 2005 for $680 million.[27] Dayton and eCompanies made headlines by buying the Business.com domain name for $7.5 million, believed to be the highest price ever paid for a domain at the time,[28] during the height of the dot com bubble; they later sold the Business.com search portal to RH Donnelly in 2007 for $345 million.[29][30][31]

In 2001, Dayton started Boingo Wireless to address what he saw as a fragmentation problem inherent in Wi-Fi networks.[32] Boingo aggregates Wi-Fi hotspots around the globe into a single network, and has grown into one of the largest Wi-Fi operators.[33] Boingo filed for its IPO in January 2011,[34] listing Dayton as owning 15% of the company.[35] 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.[6]

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.[36] 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.[37]

Dayton is an investor in and Chairman of digital education company Age of Learning,[38][39] which raised $150 million in May, 2016, giving the company a $1 billion valuation.[40] He is also an investor in and board member of Diffbot,[41][42] a semantic web and structured data startup,[43] and Artsy,[44][45] an online art marketplace, which raised a reported $50 million in July, 2017.[46] Dayton said of the art market and company, “only very few people who could afford to buy [art] are doing so. Many are held back by high barriers to entry, which Artsy is solving.”[47] He is an investor in Joby Aviation, a NASA LeapTech participant building an electric vertical take-off and landing aircraft, which raised $100 million from Intel, JetBlue and Toyota in February, 2018.[48][49] Dayton was an early investor in video doorbell company Ring,[50] which was acquired by Amazon in February, 2017 for $1 billion.[51] Dayton is a co-founder of City Storage Systems & CloudKitchens, which in March, 2018 secured a $150 million investment from Uber founder Travis Kalanick, who also joined the company as its CEO,[52][53] with plans as of February, 2019, to expand into China.[54][55] 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.”[56]

Dayton has identified himself as a libertarian and has listed authors Henry Hazlitt, Frederic Bastiat, and Ayn Rand as significant influences, stating, “It never occurred to me to go to the government for a solution. It seems barbaric. A medieval solution to a Net-age problem.”[57]

In 2011, he co-hosted an event to support then Deputy Mayor and Independent candidate Austin Beutner in the Los Angeles mayoral election, 2013.[58]

He was chosen as Entrepreneur of the Year in 1999 by the Lloyd Greif Center at the University of Southern California's Marshall School of Business.[59] In 1999, Dayton was named to the MIT Technology Review TR100, a list of the top 100 innovators in the world under the age of 35,[60] and in 2010 was a recipient of the Dream Keeper award from the I Have a Dream Foundation.[61]

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.[62][63]

Dayton is a surfer,[64] amateur poker player,[65] and airplane pilot.[66] In 2013, the FAA (Federal Aviation Administration) recognized Dayton by his inclusion in the FAA Airmen Certification Database.[67]

Dayton is married to novelist Arwen Elys Dayton and they have three children and live in the Pacific Northwest.[68][69]

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