Sky Dayton

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Sky Dayton at the Web 2.0 Conference, 2005

Sky Dylan Dayton (born August 8, 1971) is an American entrepreneur.

Dayton is the founder of EarthLink,[1][2][3] co-founder of eCompanies,[4] and the founder of Boingo.[5][6]

Early life[edit]

Dayton's father was a sculptor and his mother 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 young Sky to technology.[4][7]

At the age of 9, Dayton got his first computer, a Sinclair ZX81. He learned to program in BASIC on this early machine. At age 16, Dayton graduated from The Delphian School, a private boarding school in Oregon, which uses study methods developed by L. Ron Hubbard. He got a job at an entertainment advertising firm, where he became exposed to Apple Macintosh hardware and soon managed the digital imaging department. He then moved on to a larger advertising agency, Mednick & Associates, where he held a similar role until he was 18.[8][9]

Entrepreneurial career[edit]

In late 1990, at the age of 19, Dayton and a friend raised money from family and friends and opened Mocha Gallery, an art gallery and coffee house in L.A. He and his partner eventually changed the name to Cafe Mocha and took over another coffeehouse called Joe Cafe in Studio City, California.[4][10][11]

In 1992, while still managing Cafe Mocha, Dayton and friend Adam Wicks Walker opened Dayton/Walker Design, a Studio City advertising and design firm, in 1992. Dayton/Walker served entertainment clients including Fox Television, Disney, Columbia Pictures, Sony Pictures, and Warner Brothers.[9][12]

In 1993, Dayton heard about the Internet. After spending 80 hours trying to get his Macintosh computer to log in, he finally got connected. Realizing that the Internet was likely to become the next mass medium, in 1994 he decided to start EarthLink.[13] In search of startup capital, he approached Kevin O'Donnell, father of a childhood friend. O'Donnell brought in Reed Slatkin and the two became EarthLink's first financial backers.[10][11] (Though they have sometimes been referred to as EarthLink co-founders, EarthLink and numerous media sources reserve the "Founder" title for Dayton).[1][3][14][15] Other investors followed, including Greg B. Abbott, former AT&T CFO Robert Kavner[16] and Chip Lacy, and eventually larger investors such as George Soros.[17]

Dayton described what it was like in the early days in an article in Vanity Fair:[18]

I owned a couple of coffeehouses in L.A., and I had a computer-graphics company that I co-owned. And 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

Dayton began EarthLink in 600 square feet (56 m2) of space in an office in Los Angeles. He expanded the company and by the summer of 1995 EarthLink was able to provide national service enabled by its agreement with UUNET. In 1996 Dayton moved from founding CEO to executive chairman, handing over day-to-day operations of the company to Charles "Garry" Betty. At the time, the company was growing at a rate of 5 percent to 10 percent a week.[17] A long-time Mac user, in 1998, Dayton led the creation of a strategic partnership with Steve Jobs at Apple that saw EarthLink become the default ISP preloaded on the iMac,[19] and later led to a $200M investment by Apple in the company.[20]

EarthLink grew to become a leading Internet service provider, with millions of customers and over $1 billion in annual revenue.

In June 1999, Dayton became non-executive chairman of EarthLink and formed eCompanies with former Disney Internet chief Jake Winebaum. eCompanies began as an incubator and venture capital fund for developing Internet companies.[4] It is a privately held company, and while it struggled for a time,[21] it ultimately launched several successful companies, including, which was purchased by Experian in 2005 for $380M, JAMDAT Mobile, which went public and was then purchased by Electronic Arts in 2005 for $680 million, and (the domain for which Dayton and Winebaum bought for $7.5M during the height of the dot com bubble), which was purchased by RH Donnelly in 2007 for $345 million.

Dayton started Boingo Wireless in 2001 to solve the fragmentation problem inherent in Wi-Fi networks.[22] Boingo aggregates Wi-Fi “hot spots” around the globe into a single system for consumers and it has grown into one of the largest Wi-Fi operators in the world.[23] Boingo filed to go public in January 2011,[24] listing Dayton as owning 15%.[25] Dayton served as Boingo's chairman until August, 2014.[6]

On May 4, 2011, Boingo Wireless went public selling 5,770,000 shares at $13.50, raising $77.9 million. Of the shares sold in the offering, the company sold 3,846,800 shares and selling stockholders 1,923,200 shares. After the offering, the company has 32.5 million shares out, giving the company a market capitalization of around $439 million on the offering…and less now.[26]

Dayton became CEO of Helio upon the company’s launch in 2005. At that time, he 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 sale. Helio was acquired by Virgin Mobile USA in 2008.

Dayton is an investor and board member of semantic web startup Diffbot,[27] online education company Age of Learning,[28] and online art marketplace Artsy,[29] which raised a reported $18.5 million in April, 2014, and at the time Dayton said of the art market and company, “only very few people who could afford to buy are doing so. Many are held back by high barriers to entry, which Artsy is solving.”[30]

Politics and social advocacy[edit]

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.”[31] In 2011, he co-hosted an event to support the then Deputy Mayor and Independent candidate Austin Beutner in the Los Angeles mayoral election, 2013.[32]

Other activities and awards[edit]

Dayton served on the advisory board of the Center for Public Leadership at the John F. Kennedy School of Government at Harvard University.[33]

He was chosen as Entrepreneur of the Year by the Lloyd Greif Center at the University of Southern California's Marshall School of Business. He is a recipient of the Dream Keeper award from the I Have a Dream Foundation[34] and in 1999 he was named to the MIT Technology Review TR100 as one of the top 100 innovators in the world under the age of 35.[35]

Family and leisure[edit]

Dayton is a surfer,[36] amateur poker player [37] and airplane pilot.[38]

Dayton is married to novelist Arwen Elys Dayton. They are Scientologists and they have three children.[39][40]


  1. ^ Maney, Kevin (January 22, 2002). "Dayton an unlikely tech marvel". USA Today. 
  2. ^ a b Rose, Frank (March 2006). "Sky Dayton Gets Mobile". Wired. 
  3. ^ a b c d Dean, Jason (2012). "Sky Dayton: This SKY Has No Limits". CSQ. 
  4. ^ Moschovitis, Christos J. P.; Laura Lambert; Chris Woodford. Hilary W. Poole, ed. The Internet: Biographies. ABC-CLIO. pp. 65–70. ISBN 1851096590. 
  5. ^ a b "Sky Dayton Steps Away from Boingo to Focus on Startups". SoCalTech. August 8, 2014. 
  6. ^ Bloom, David (June 9, 1998), "Electronic Midas Touch", Los Angeles Daily News
  7. ^ Bloom, David (June 9, 1998), "Electronic Midas Touch", Los Angeles Daily News
  8. ^ a b "Interview: Boingo Wireless Chairman Sky Dayton". (June 1, 2010). Los Angeles Daily News.[1]
  9. ^ a b Armstrong, Larry (December 4, 1997). "The Mac of Internet Providers". BusinessWeek. 
  10. ^ a b "Q&A with Sky Dayton". Businessweek. September 10, 2006. 
  11. ^ Nee, Eric (July 27, 1997), "Surf's Up". Forbes, p. 106
  12. ^ McGarvey, Robert (December 31, 1997). "Sky's The Limit: EarthLink's founder tells how he found his fortune on the Net - and how you can, too". Entrepreneur Magazine. 
  13. ^ Levy, Steven (June 25, 2006). "Going Faster". Newsweek. 
  14. ^ Frommer, Dan (January 3, 2007). "EarthLink CEO Garry Betty Dies". Forbes. 
  15. ^ "EarthLink Holdings Corp". Businessweek. Retrieved January 7, 2013. 
  16. ^ a b Margonelli, Lisa (October 1998), "The Sky's the Limit". POV.
  17. ^ Keenan Mayo and Peter Newcomb (July 2008)An Oral History of the Internet Vanity Fair
  18. ^ Apple, Inc. press release (August 1998), "Apple Selects EarthLink as ISP"[2]
  19. ^ Menn, Joseph (January 2000)"Apple Buys $200 Million Stake in EarthLink". Los Angeles Times [3]
  20. ^ O’Shea, Dan (April 1, 2002). "Sky Dayton is smarter than you, richer than you and younger than you. (But he's very sorry about that.)". Connected Planet. 
  21. ^ Fleishman, Glenn (December 4, 2002). "Day 2 at 802.11 Planet Conference". Wi-Fi Networking News. Retrieved November 28, 2012. 
  22. ^ Foresman, Chris (July 3, 2008). "Boingo Offers New Mac-Compatible Client for WiFi Network". Ars Technica. Retrieved November 28, 2012. 
  23. ^ Kim, Ryan (January 14, 2011), "While Everyone Watches Groupon, Boingo Files for IPO" GigaOm [4]
  24. ^ Boingo S-1 filing (Jan 14, 2011), SEC
  25. ^ Eric Savitz, (May 4, 20100) "Boingo Wireless IPO Finds Lukewarm Reception On Day One" [5]/
  26. ^ Perez, Sarah (May 31, 2012). "Diffbot Raises $2 Million Angel Round For Web Content Extraction Technology". TechCrunch. 
  27. ^ "Age of Learning". Leadership. Retrieved November 4, 2014. 
  28. ^ Kazakina, Katya (February 25, 2013). "Earthlink's Dayton Joins Artsy, Firm Raises $5 Million". BusinessWeek. 
  29. ^ Kolodny, Lora (April 3, 2014). "New York Startup Artsy Raises $18.5M to Become Pandora for Fine Art". The Wall Street Journal. 
  30. ^ Seth Lubove (14 June 1999). "". Retrieved 26 December 2013. 
  31. ^ Tina Daunt (21 November 2011). "L.A. Mayor Race: Who in Hollywood Is Supporting Whom". The Hollywood Reporter. Retrieved 7 January 2013. 
  32. ^ "Warren Bennis Leadership Circle". Center for Public Leadership. Harvard Kennedy School. Retrieved October 19, 2012. 
  33. ^ Life Magazine: Sky Dayton, Jennifer Garner, Dave Winfield -- I Have a Dream Foundation Gospel Brunch, House of Blues [6][dead link]
  34. ^ "1999 Young Innovators Under 35: Sky Dayton, 32". Technology Review. 1999. Retrieved October 19, 2012. 
  35. ^ "Sky Dayton Blog". Surfing In Indonesia. Retrieved January 6, 2013. 
  36. ^ "The 10 Biggest Poker Players in Silicon Valley". Business Insider. Retrieved December 1, 2014. 
  37. ^ "Sky Dayton Blog". Emergency Maneuver Training. Retrieved January 6, 2013. 
  38. ^ Dayton, Sky. Bio on personal website.
  39. ^ "Interview: Boingo Wireless Chairman Sky Dayton". (June 1, 2010). Los Angeles Daily News.

Further reading[edit]

External links[edit]

Selected speeches, writings and interviews[edit]