Sky Dayton
Angel Investor @ Craft Ventures
Los Angeles, United States
Sky Dayton is a seed investor at Craft Ventures in Los Angeles focused on Software and Aerospace. 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.
- Total investments:
- 28
- Last investment:
- Lead investor:
- 25%
Last updated:
For AI agents: llms.txt
Industries Sky Dayton invests in
Stages Sky Dayton invests in
Countries Sky Dayton invests in
Round sizes
Contacts
| Type | Contact | Validation |
|---|---|---|
| Work email | ||
| Personal email | ||
| Work phone | ||
| Personal phone | ||
| Socials |
Round size
- Seed
- $2M–$15M
- Series A
- $1.5M–$25M
- Series B
- $15M–$100M
Investment Focus
Industry
- Software 4 (14%)
- Aerospace 4 (14%)
- Internet 3 (11%)
- Information Technology 3 (11%)
- Artificial Intelligence 3 (11%)
Stage
- Seed 11 (39%)
- Series B 5 (18%)
- Series A 4 (14%)
- Angel 3 (11%)
- Pre-Seed 1 (4%)
Country
- United States 20 (71%)
- Switzerland 1 (4%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
| HYFIX Spatial Intelligence is a Machinery Manufacturing firm developing IoT-friendl software and hardware. | $15M / Seed / Apr 15, 2026 | ||
| Xona Space Systems is building a next-generation satellite navigation system using small but powerful satellites in low-Earth orbit. The constellation they are developing is designed to provide secure navigation and timing services with the resilience and accuracy that modern intelligent systems, such as autonomous vehicles and drones, need tooperate safely at scale. | $170M / Series C / Mar 26, 2026 | ||
| Loft Dynamics is a training solutions provider that creates a virtual reality (VR) flight simulator. It was the first VR full motion simulator to receive Flight Simulation Training Device (FSTD) EASA FTD Level 3 authorization from the European Union Aviation Safety Agency (EASA). Loft Dynamics, with a talented team of passionate engineers, highlyspecialized developers, and dedicated aviation experts, assists leading global aircraft manufacturers, airlines, aviation operators, flight schools, and training organizations around the world in providing safer and more effective pilot training.It was formerly known as VRMotion AG, which was founded in Zurich in 2018 and has quickly established itself as the market leader in the development and manufacture of virtual reality training devices for helicopter pilots. | $24M / Series B / Aug 21, 2025 | ||
| Xona Space Systems is building a next-generation satellite navigation system using small but powerful satellites in low-Earth orbit. The constellation they are developing is designed to provide secure navigation and timing services with the resilience and accuracy that modern intelligent systems, such as autonomous vehicles and drones, need tooperate safely at scale. | $92M / Series B / Jun 26, 2025 | ||
| Garden assists lawyers and businesses in automating the creation of new patents and analyzing potential infringements. The company develops AI agents that manage routine tasks, enabling users to concentrate on patent strategy. | $6.8M / Seed / Aug 15, 2024 | ||
| AI fighting AI.CISOs face an impossible risk landscape today. 80% of cybersecurity breaches start because of employee error. The problem is exacerbating with generative AI, as a single hacker can specifically target thousands of employees in the same amount of time that they used to specifically target tens of employees with social engineering.CISOs lack tools to deal with employee risk and are held accountable when a breach inevitably happens.By leveraging AI at each step, Dune Security empowers organizations to quantify individual risk through analyzing user behavior, context, learning patterns, and third party data. This allows the automation of tailored cybersecurity measures to each individual, transforming vulnerabilities into strengths. Dune is the central engine of all employee risk data, which is a solution that is not just timely for organizations but necessary in navigating the present cybersecurity landscape. This gives the CISO the capability to understand who are the high risk employees, to what extent, and why - as well as automatically remediate and restrict access to keep their organization safe.Today, Dune Security uniquely replaces legacy and ineffective security awareness training by pinpointing the crucial 8% of employees responsible for 80% of the risk, ensuring all employees receive personalized, machine learning-driven training tailored to their risk profile. CISOs also have easy access to quantifiable data via robust reporting and API-out capability, enabling them to both report to compliance auditors, regulators, and insurance underwriters, as well as restrict access to high-risk employees through other security systems. | $2M / Seed / May 23, 2024 | ||
| AI fighting AI.CISOs face an impossible risk landscape today. 80% of cybersecurity breaches start because of employee error. The problem is exacerbating with generative AI, as a single hacker can specifically target thousands of employees in the same amount of time that they used to specifically target tens of employees with social engineering.CISOs lack tools to deal with employee risk and are held accountable when a breach inevitably happens.By leveraging AI at each step, Dune Security empowers organizations to quantify individual risk through analyzing user behavior, context, learning patterns, and third party data. This allows the automation of tailored cybersecurity measures to each individual, transforming vulnerabilities into strengths. Dune is the central engine of all employee risk data, which is a solution that is not just timely for organizations but necessary in navigating the present cybersecurity landscape. This gives the CISO the capability to understand who are the high risk employees, to what extent, and why - as well as automatically remediate and restrict access to keep their organization safe.Today, Dune Security uniquely replaces legacy and ineffective security awareness training by pinpointing the crucial 8% of employees responsible for 80% of the risk, ensuring all employees receive personalized, machine learning-driven training tailored to their risk profile. CISOs also have easy access to quantifiable data via robust reporting and API-out capability, enabling them to both report to compliance auditors, regulators, and insurance underwriters, as well as restrict access to high-risk employees through other security systems. | $2M / Pre-Seed / Apr 22, 2024 | ||
| EchoMark is an information security startup focused on enabling a flow of private information and keeping private information private. | $10M / Seed / Sep 27, 2023 | ||
| Trellis Research is a research tool for litigators. | $15M / Series B / Aug 22, 2023 | ||
| Fuse is accelerating the world's transition to Fusion Energy. | $17M / Seed / Mar 08, 2023 | ||
| See all 28 investments → | |||
Co-Investors
About Craft Ventures
Craft Ventures is an early-stage and growth venture fund specializing in the craft of building great companies. Craft Ventures aims to support and scale innovative companies in various sectors including consumer, enterprise, and financial services. They often invest in companies with a strong founding team, a clear vision, and a scalable business model.
Craft Ventures Contacts
| Name | Phone | Socials | |
|---|---|---|---|
Jennifer Sui
Associate & Investor
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Mike Marg
Partner & Investor
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Ryan Hrabak
Principal
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Arra Malekzadeh
Principal
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Bill Lee
Co-Founder and Venture Partner
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FAQ
What does Sky Dayton invest in?
Sky Dayton invests primarily in Software, Aerospace and Internet startups, most often at Seed and Series B stage. Most of the 28 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
What round sizes does Sky Dayton invest in?
Sky Dayton typically joins rounds of $2M–$15M at Seed, $1.5M–$25M at Series A and $15M–$100M at Series B. These are whole funding-round sizes, not Sky Dayton's own check, which is rarely disclosed: the 10th–90th percentile of the confirmed public funding rounds Sky Dayton took part in.
How do I contact Sky Dayton?
Public channels for Sky Dayton include LinkedIn, X (Twitter) and the website linked on this profile. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.
When did Sky Dayton last invest?
The most recent investment recorded for Sky Dayton closed in Apr 2026. Shizune tracks 28 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Oct 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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