Sky Dayton
About Sky Dayton
Sky Dayton is an American entrepreneur and investor. He founded the internet service provider EarthLink in 1994. He later co-founded the internet incubator eCompanies with Disney executive Jake Winebaum. He also founded Boingo Wireless and co-founded City Storage Systems and CloudKitchens.
Wellfound lists him as a co-founder of Jamdat and Business.com, and as a board member or investor at Age of Learning, Artsy, Diffbot, Joby and Ring. Tracxn lists him as a board member of Xona Space Systems. NFX Signal and Wikidata list him as a venture partner at Craft Ventures. He is based in Los Angeles.
Crunchbase counts 21 personal investments, and PitchBook counts 36. Crunchbase shows him as lead investor on an angel round in Diffbot. PitchBook dates several of his deals: Swarm (January 2019), Trellis Research seed (March 2019), Antara Health (September 2019), Tertulia (March 2022), Loft Dynamics (September 2022 and August 2025), Fuse (March 2023) and Enhanced Radar (May 2026). Crunchbase also shows him as a lead investor, alongside Craft Ventures, in Swarm Technologies' Series A.
His AI-related deal on the Lounge deals desk is HYFIX Spatial Intelligence, a $15M seed round announced in April 2026. HYFIX is a Santa Clara semiconductor company building U.S.-made chips that combine flight control, positioning, secure communications and onboard compute for drones and autonomous robots. Craft Ventures led the round. Catapult Ventures, Multicoin Capital, Finality Capital and Sky Dayton also took part.
He was an early investor and board member at Diffbot, a company that extracts structured data from the web. We did not find other AI-labelled investments with confirmed dates.
His public record covers hardware, connectivity, aerospace, consumer and enterprise companies, and he often invests alongside Craft Ventures. Third-party databases describe a seed-stage focus, but we found no statement from Dayton on stage, sectors or what he looks for. He has published no check size, and databases that list ranges do not source them, so we omit them.
- HYFIX Spatial Intelligence: U.S.-made chips for drones and robots; $15M seed round, April 2026.
- Diffbot: web data extraction company; angel round and board seat.
- Swarm Technologies: satellite connectivity company; Series A with Craft Ventures; PitchBook dates his deal to January 2019.
- Loft Dynamics: flight simulator hardware; invested September 2022 and August 2025 per PitchBook.
- Trellis Research: B2B information services; seed round in March 2019 per PitchBook.
- Tertulia: book discovery service; seed round, March 2022 per PitchBook.
- Artsy, Age of Learning, Joby, Ring: board or investor roles listed on Wellfound; years not confirmed.
- crunchbase.com/person/sky-dayton
- en.wikipedia.org/wiki/Sky_Dayton
- wellfound.com/p/sky-dayton
- pitchbook.com/profiles/investor/106425-64
- signal.nfx.com/investors/sky-dayton
- wikidata.org/wiki/Q7537295
- tracxn.com/d/people/sky-dayton/___VAb6GmS_hPQQwEBJNHn0f7AdXs61KrqZOMgr
- dronelife.com/2026/04/15/hyfix-raises-15m-to-build-u-s-made-drone-chip
Investing activity
Sky Dayton appears in 1 AI deal tracked by the Lounge deals desk, rounds totalling $15M. The rounds are mostly Seed, with a median round size of $15M. The most recent is HYFIX Spatial Intelligence (Seed, $15M, Apr 2026).
Sky Dayton most often invests alongside Craft Ventures, Multicoin Capital, Finality Capital Partners and Catapult Ventures, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about Sky Dayton
Does Sky Dayton invest in AI startups?
Yes. He took part in HYFIX Spatial Intelligence's $15M seed round in April 2026, and he was an early investor and board member at Diffbot. HYFIX builds AI-era chips for drones and robots.
What is Sky Dayton's check size?
He has not made a check size public. Some databases list ranges, but they do not cite a source, so we do not repeat them.
What stage does Sky Dayton invest in?
His documented deals include seed rounds (HYFIX, Trellis Research, Tertulia) and a Series A (Swarm). He has made no public statement on a preferred stage.
Is Sky Dayton affiliated with Craft Ventures?
NFX Signal and Wikidata list him as a venture partner at Craft Ventures. Craft led HYFIX's seed round, and he also invested in Swarm's Series A alongside Craft.
What companies has Sky Dayton founded?
He founded EarthLink and Boingo Wireless. He co-founded eCompanies, City Storage Systems and CloudKitchens.
How should founders reach Sky Dayton?
Use his public LinkedIn or X profiles, or his personal site. He has published no pitch process or email.
Is Sky Dayton an angel investor?
Yes. Sky Dayton invests personally as an angel.
What AI companies has Sky Dayton invested in?
Sky Dayton's AI investments include HYFIX Spatial Intelligence. The 1 round on Lounge are listed on this page with amounts, dates and co-investors.
What stage does Sky Dayton invest at?
In the rounds tracked on Lounge, Sky Dayton has invested at Seed, with a median round of $15M.
Who does Sky Dayton co-invest with?
Sky Dayton's most frequent co-investors on Lounge are Craft Ventures (1 deal), Multicoin Capital (1 deal), Finality Capital Partners (1 deal) and Catapult Ventures (1 deal).