Sky Dayton

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, and co-founder of City Storage Systems and CloudKitchens.

Dayton's father was the sculptor Wendell Dayton, and his mother is Alice Pero, a poet and flutist.

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.

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.

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.

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.

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.

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.

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: "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?"

In 1994, Dayton founded EarthLink, an Internet service provider (ISP) that would offer Internet access to the public.

Kevin O'Donnell, father of a childhood friend, and Reed Slatkin became EarthLink's first financial backers.

Other investors followed, including Greg B. Abbott, former AT&T CFO Robert Kavner, Chip Lacy, and eventually larger investors such as George Soros.

EarthLink started in a small office of 600 sqft 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 Charles "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.

This arrangement led to a $200 million investment by Apple in EarthLink.

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.

In June 1999, Dayton left day-to-day operations at EarthLink and went on to launch four other companies including Helio and Business.com.

He formed eCompanies, an incubator and venture capital fund for developing Internet companies, with former Disney Internet chief Jake Winebaum.

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.

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.

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.

Boingo filed for its IPO in January 2011, listing Dayton as owning 15% of the company.

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.

Dayton is a board member of the digital education company Age of Learning, which raised $150 million in 2016 at a $1 billion valuation, and $300 million in July 2021, giving the company a $3 billion valuation.

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.