Sky Dayton

Sky Dylan Dayton (born August 8, 1971) is an American entrepreneur and investor. He is the founder of Internet service provider EarthLink,[1][2][3] co-founder of eCompanies,[4] and the founder of Boingo.[5][6]

Sky Dayton
Sky Dayton, Web 2.0 Conference.jpg
Sky Dayton at the Web 2.0 Conference, 2005
Born8 August 1971
New York City, New York
Spouse(s)Arwen Elys Dayton

Early lifeEdit

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][relevant? ]

Entrepreneurial careerEdit

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, 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 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 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]

Politics and social advocacyEdit

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]

Other activities and awardsEdit

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]

Personal lifeEdit

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][relevant? ]

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


  1. ^ Maney, Kevin (January 22, 2002). "Dayton an unlikely tech marvel". USA Today.
  2. ^ 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. Archived from the original on January 8, 2014.
  4. ^ Moschovitis, Christos J. P.; Laura Lambert; Chris Woodford (2005). 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. ^ "A California Sculptor Gets His Moment in the Sun, at Age 80". Retrieved July 29, 2018.
  7. ^ Bloom, David (June 9, 1998), "Electronic Midas Touch", Los Angeles Daily News
  8. ^ "Delphian School, The". Northwest Association of Independent Schools. Retrieved August 5, 2019.
  9. ^ Lee, Alfred (May 31, 2010). "INTERVIEW: Boingo Wireless Chairman Sky Dayton cites communication as a guiding factor in his artistic pursuits and his Internet business career". Los Angeles Business Journal. Retrieved August 5, 2019.
  10. ^ "Online Extra: Q&A with Sky Dayton". Retrieved May 30, 2016.
  11. ^ "Sky Dayton's Long Road to Internet Nirvana". WIRED. Retrieved May 30, 2016.
  12. ^ Bloom, David (June 9, 1998), "Electronic Midas Touch", Los Angeles Daily News
  13. ^ a b "Interview: Boingo Wireless Chairman Sky Dayton". (June 1, 2010). Los Angeles Daily News."Archived copy". Archived from the original on July 10, 2010. Retrieved August 2, 2010.CS1 maint: archived copy as title (link)
  14. ^ a b Armstrong, Larry (December 4, 1997). "The Mac of Internet Providers". BusinessWeek.
  15. ^ a b "Q&A with Sky Dayton". Businessweek. September 10, 2006.
  16. ^ Nee, Eric (July 27, 1997), "Surf's Up". Forbes, p. 106
  17. ^ McGarvey, Robert J. "Sky's The Limit". Entrepreneur. Retrieved May 30, 2016.
  18. ^ Keenan Mayo and Peter Newcomb (July 2008)An Oral History of the Internet Vanity Fair
  19. ^ 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.
  20. ^ "EarthLink Holdings Corp". Businessweek. Retrieved January 7, 2013.
  21. ^ a b Margonelli, Lisa (October 1998), "The Sky's the Limit". POV.
  22. ^ Apple, Inc. press release (August 1998), "Apple Selects EarthLink as ISP"[1]
  23. ^ Menn, Joseph (January 2000)"Apple Buys $200 Million Stake in EarthLink". Los Angeles Times [2]
  24. ^ "Time Warner teams with EarthLink, delays AOL merger review". CNET. Retrieved May 30, 2016.
  25. ^ "Possible Marriage Proposals Are Lifting Earthlink". Retrieved May 30, 2016.
  26. ^ "Electronic Arts Jams With Jamdat". December 12, 2005. Retrieved February 17, 2017.
  27. ^ Newswires, Peter Loftus Dow Jones (November 30, 1999). "ECompanies Pays $7.5 Million For Domain Name ''". Wall Street Journal. ISSN 0099-9660. Retrieved May 30, 2016.
  28. ^ 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. Archived from the original on January 8, 2014.
  29. ^ Contributor. " Sells for $350 Million". TechCrunch. Retrieved May 29, 2016.
  30. ^ "Jackpot! Sells for $350 Million". WIRED. Retrieved May 30, 2016.
  31. ^ Fleishman, Glenn (December 4, 2002). "Day 2 at 802.11 Planet Conference". Wi-Fi Networking News. Retrieved November 28, 2012.
  32. ^ Foresman, Chris (July 3, 2008). "Boingo Offers New Mac-Compatible Client for WiFi Network". Ars Technica. Retrieved November 28, 2012.
  33. ^ Kim, Ryan (January 14, 2011), "While Everyone Watches Groupon, Boingo Files for IPO" GigaOm [3]
  34. ^ Boingo S-1 filing (Jan 14, 2011), SEC
  35. ^ "EarthLink mobile venture renamed 'Helio'". CNET. Retrieved May 29, 2016.
  36. ^ "Virgin Mobile USA buys Helio for $39 million". CNET. Retrieved May 29, 2016.
  37. ^ "Age of Learning". Leadership. Retrieved November 4, 2014.
  38. ^ "Curriculum Board, Academic Leadership, Management at Age of Learning". Retrieved May 29, 2016.
  39. ^ Lunden, Ingrid. "Age of Learning, a quiet giant in education apps, raised $150M at a $1B valuation from Iconiq". TechCrunch. Retrieved May 29, 2016.
  40. ^ Perez, Sarah (May 31, 2012). "Diffbot Raises $2 Million Angel Round For Web Content Extraction Technology". TechCrunch.
  41. ^ Chapman, Lizette (May 31, 2012). "Investors Back Diffbot's 'Visual Learning Robot' for Web Content". Wall Street Journal.
  42. ^ Shieber, Jonathan. "Diffbot Aims To Build The Intel Of Data For Artificial Intelligence". TechCrunch. Retrieved May 30, 2016.
  43. ^ Kazakina, Katya (February 25, 2013). "Earthlink's Dayton Joins Artsy, Firm Raises $5 Million". BusinessWeek.
  44. ^ Goel, Vindu (October 28, 2015). "Purchasing Fine Art Is Increasingly Just a Click Away". The New York Times. ISSN 0362-4331. Retrieved May 29, 2016.
  45. ^ "Online art marketplace Artsy raises $50M at $275M valuation to double down on auctions – TechCrunch". Retrieved March 25, 2018.
  46. ^ Kolodny, Lora (April 3, 2014). "New York Startup Artsy Raises $18.5M to Become Pandora for Fine Art". The Wall Street Journal.
  47. ^ "Joby Aviation wins a $100M investment boost to get its flying cars off the ground". GeekWire. February 1, 2018. Retrieved March 25, 2018.
  48. ^ "Air-Taxi Startup Has a Working Prototype and a Fresh $100 Million". February 1, 2018. Retrieved March 25, 2018.
  49. ^ "This guy turned his failure on 'Shark Tank' into a $28 million investment from Richard Branson". Business Insider. Retrieved March 25, 2018.
  50. ^ Editorial, Reuters. "Amazon buys startup Ring in $1 billion deal to run your home security". U.S. Retrieved March 25, 2018.
  51. ^ "Travis Kalanick is buying a new company that rehabs real estate and will run it as CEO". Recode. Retrieved March 25, 2018.
  52. ^ "Briefing: Travis Kalanick Buys a Friend's Startup, Is CEO Again". The Information. Retrieved March 25, 2018.
  53. ^ Yang, Yingzhi (February 1, 2019). "Former Uber CEO Travis Kalanick said to plot China comeback with 'shared kitchen' business". South China Morning Post. Retrieved August 5, 2019.
  54. ^ Loizos, Connie. "The next big bet for former Uber CEO Travis Kalanick may be cloud kitchens — in China". TechCrunch. Retrieved August 5, 2019.
  55. ^ "Exclusive: Satellite Startup Swarm Raises $25 Million For Space-Based Internet Plan". Fortune. Retrieved April 21, 2019.
  56. ^ Seth Lubove (June 14, 1999). "". Retrieved December 26, 2013.
  57. ^ Tina Daunt (November 21, 2011). "L.A. Mayor Race: Who in Hollywood Is Supporting Whom". The Hollywood Reporter. Retrieved January 7, 2013.
  58. ^ "Holdings: A very special day with Sky Dayton". Retrieved May 29, 2016.
  59. ^ "1999 Young Innovators Under 35: Sky Dayton, 32". Technology Review. 1999. Retrieved October 19, 2012.
  60. ^ Life Magazine: Sky Dayton, Jennifer Garner, Dave Winfield -- I Have a Dream Foundation Gospel Brunch, House of Blues [4][dead link]
  61. ^ "Warren Bennis Leadership Circle". Center for Public Leadership. Harvard Kennedy School. Archived from the original on January 8, 2014. Retrieved October 19, 2012.
  62. ^ "Emerging Technologies Conference at MIT: Speakers". Retrieved May 29, 2016.
  63. ^ "Sky Dayton Blog". Surfing In Indonesia. Retrieved January 6, 2013.
  64. ^ "The 10 Biggest Poker Players in Silicon Valley". Business Insider. Retrieved December 1, 2014.
  65. ^ "Sky Dayton Blog". Emergency Maneuver Training. Retrieved January 6, 2013.
  66. ^ "FAA recognizes Sky Dylan Dayton". Archived from the original on June 25, 2016. Retrieved May 29, 2016.
  67. ^ Dayton, Sky. Bio on personal website.
  68. ^ "Interview: Boingo Wireless Chairman Sky Dayton". (June 1, 2010). Los Angeles Daily News.

Further readingEdit

External linksEdit

Selected speeches, writings and interviewsEdit