Sky Dayton

Sky Dayton, an American entrepreneur and investor, is best known for helping to bring internet access to the masses. Currently, he invests in and sits on the boards of several companies. Back in the days of dial-up, getting online was challenging. Dayton resorted to what many startup founders do when they can't find the product or service they need: create it. Dayton couldn’t access the internet easily the first time he tried, so in 1994 he founded EarthLink, an internet service provider (ISP) with a strong customer service focus and user-friendly software. His timing was auspicious: Shortly after EarthLink became a publicly traded company and Apple founder Steve Jobs resumed the helm of his company, Dayton and Jobs formed a strategic partnership to make EarthLink the default ISP preloaded on the iMac. This led to Apple investing $200M in EarthLink. Flush with this success, Dayton teamed up with Disney executive Jake Winebaum to create a dotcom incubator, eCompanies, where they created Business.com, Jamdat Mobile and invested in LowerMyBills.com, all of which had nine figure exits. Continuing his pioneering technology startups trajectory, in 2001 Dayton founded Boingo Wireless to address the then-fragmented state of WiFi networks. Boingo unified WiFi hotspots into a single network, becoming a global WiFi leader. Dayton chaired Boingo until 2014. In 2021, Digital Colony Management bought Boingo for approximately $850M. Dayton continues to build, advise, and invest in digital companies such as Age of Learning, a leading education technology provider; Joby Aviation, which builds all-electric vertical take-off and landing (eVTOL) passenger aircraft; Transaction Tax Resources (acquired by Avalara), NeoPets (acquired by Viacom), Diffbot, and Artsy. He also co-founded virtual restaurant CloudKitchens and its parent Citiy Storage Systems, which is run by Uber founder Travis Kalanick. CloudKitchens attracted many high-profile backers, including investor Chamath Palihapitiya. Dayton led the Series A financing for Swarm Technologies, which built a pioneering low Earth orbit satellite constellation for communication with Internet of Things (IoT) devices using a store and forward design. SpaceX acquired Swarm in 2021. Most recently, Dayton joined the board of Loft Dynamics, a Swiss startup creating virtual reality (VR) simulation technology for pilots, leading their first institutional round. Dayton is also a venture partner at Craft Ventures, founded by PayPal founding COO David Sacks, StubHub co-founder Jeff Fluhr, and Remarq co-founder Bill Lee. Together, they’ve backed a number of future-focused companies, including Swarm, Loft Dynamics, and Neuralink. Entrepreneurship has been in Dayton's blood since his youth. He co-founded Café Mocha, an art gallery/coffeehouse, with a friend at the tender age of 19. In 1992, before digital was even on most people's radar, Dayton and another friend launched Dayton/Walker Design, a digital advertising and design firm for the entertainment industry, acquiring a client roster that included Disney, Sony Pictures, and Warner Brothers. When he's not founding, capitalizing, or advising companies, Dayton enjoys surfing, which helps him clear his mind and brainstorm his next venture. He's also an accomplished jet pilot. He and his wife — bestselling novelist Arwen Elys Dayton — live in the Pacific Northwest with their three children.