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, and the founder of Boingo.
Dayton's father, Wendell Dayton, is a sculptor, 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.
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 got 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.[relevant? ]
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 that 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?— Sky Dayton
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 square feet (56 m2) in Los Angeles, CA. 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. 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 $200M investment by Apple in EarthLink. 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.
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. A privately held company, eCompanies successfully launched LowerMyBills.com, which was purchased by Experian in 2005 for $380M and JAMDAT 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 $7.5M, 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, 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.
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.
Dayton is an investor in and Chairman of digital education company Age of Learning, which raised $150 million in May, 2016, giving the company a $1 billion valuation. He is also 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 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.” 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. Dayton was an early investor in video doorbell company Ring, which was acquired by Amazon in February, 2017 for $1 billion. 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.
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.”
Other activities and awards
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. 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, and in 2010 was a recipient of the Dream Keeper award from the I Have a Dream Foundation.
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- Moschovitis, Christos J. P.; Laura Lambert; Chris Woodford. Hilary W. Poole, ed. The Internet: Biographies. ABC-CLIO. pp. 65–70. ISBN 1851096590.
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- "Age of Learning". Leadership. Retrieved November 4, 2014.
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- Lunden, Ingrid. "Age of Learning, a quiet giant in education apps, raised $150M at a $1B valuation from Iconiq". TechCrunch. Retrieved 2016-05-29.
- Perez, Sarah (May 31, 2012). "Diffbot Raises $2 Million Angel Round For Web Content Extraction Technology". TechCrunch.
- Chapman, Lizette (May 31, 2012). "Investors Back Diffbot's 'Visual Learning Robot' for Web Content". Wall Street Journal.
- Shieber, Jonathan. "Diffbot Aims To Build The Intel Of Data For Artificial Intelligence". TechCrunch. Retrieved 2016-05-30.
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- "Online art marketplace Artsy raises $50M at $275M valuation to double down on auctions – TechCrunch". techcrunch.com. Retrieved 2018-03-25.
- Kolodny, Lora (April 3, 2014). "New York Startup Artsy Raises $18.5M to Become Pandora for Fine Art". The Wall Street Journal.
- "Joby Aviation wins a $100M investment boost to get its flying cars off the ground". GeekWire. 2018-02-01. Retrieved 2018-03-25.
- "Air-Taxi Startup Has a Working Prototype and a Fresh $100 Million". Bloomberg.com. 2018-02-01. Retrieved 2018-03-25.
- "This guy turned his failure on 'Shark Tank' into a $28 million investment from Richard Branson". Business Insider. Retrieved 2018-03-25.
- Editorial, Reuters. "Amazon buys startup Ring in $1 billion deal to run your home security". U.S. Retrieved 2018-03-25.
- "Travis Kalanick is buying a new company that rehabs real estate and will run it as CEO". Recode. Retrieved 2018-03-25.
- "Briefing: Travis Kalanick Buys a Friend's Startup, Is CEO Again". The Information. Retrieved 2018-03-25.
- Seth Lubove (14 June 1999). "Libertarian.net". Forbes.com. Retrieved 26 December 2013.
- Tina Daunt (21 November 2011). "L.A. Mayor Race: Who in Hollywood Is Supporting Whom". The Hollywood Reporter. Retrieved 7 January 2013.
- "Holdings: A very special day with Sky Dayton". www.library.yorku.ca. Retrieved 2016-05-29.
- "1999 Young Innovators Under 35: Sky Dayton, 32". Technology Review. 1999. Retrieved October 19, 2012.
- Life Magazine: Sky Dayton, Jennifer Garner, Dave Winfield -- I Have a Dream Foundation Gospel Brunch, House of Blues [dead link]
- "Warren Bennis Leadership Circle". Center for Public Leadership. Harvard Kennedy School. Archived from the original on January 8, 2014. Retrieved October 19, 2012.
- "Emerging Technologies Conference at MIT: Speakers". www2.technologyreview.com. Retrieved 2016-05-29.
- "Sky Dayton Blog". Surfing In Indonesia. Retrieved January 6, 2013.
- "The 10 Biggest Poker Players in Silicon Valley". Business Insider. Retrieved December 1, 2014.
- "Sky Dayton Blog". Emergency Maneuver Training. Retrieved January 6, 2013.
- "FAA recognizes Sky Dylan Dayton". aviation-business-gazette.com. Retrieved 2016-05-29.
- Dayton, Sky. Bio on personal website.
- "Interview: Boingo Wireless Chairman Sky Dayton". (June 1, 2010). Los Angeles Daily News.
- Rose, Frank (March 2006), "Sky Dayton Gets Mobile". Wired Magazine, pp. 154–162.
- Young, Shawn (October 26, 2005), "EarthLink, SK Telecom Dial In to Data Venture". The Wall Street Journal, p. B4.
- "EarthLink Inc.: Wireless Joint Venture Is Signed With South Korea's SK Telecom". (January 27, 2005). The Wall Street Journal, p. D6.
- Ankeny, Jason (March 2005), "Sky Dayton's Newest Next Big Thing (Again)". Wireless Review, pp. 45–50.
- "Surfing Book of Records: Most Enterprising Surfer". (October 2004). Surfing Magazine, p. 66.
- Dayton, Sky (May 2003). "Education in the Internet Age". Imprimis, pp. 1–5.
- Dayton, Sky (March 25, 2002). "When Capital Corrupts". Forbes ASAP.
- Helio: About Helio: Meet our leaders: Sky Dayton's Bio. Retrieved May 9, 2006
- McGarvey, Robert J. (January 1998), "Sky's The Limit". Entrepreneur.com.
- I Have a Dream Foundation Dream Keeper Award Recipient (February 2010). 
- EarthLink, Inc. company profile, fundinguniverse.com 
- Warren Bennis Leadership Circle, Center for Public Leadership, John F. Kennedy School of Government, Harvard University
- Sky Dayton, Jennifer Garner, Dave Winfield—I Have a Dream Foundation Gospel Brunch, House of Blues