Sky Dayton and the trouble with getting connected

On Valentine’s Day in 1995, Sky Dayton’s customers could no longer get into the internet. EarthLink’s subscriber database had become corrupted. The company had a backup tape, which was encouraging, right up until the engineers discovered they could not read it. A business devoted to connecting people was suddenly very good at keeping them apart.

The office had recently expanded from 800 square feet to 3,000. Even that was too small; people were working in the hallway. Growth had supplied all the usual evidence of success, and then a single file made the evidence look beside the point. Usernames and passwords had to work.

A customer referred Dayton to a data recovery company in San Diego. Someone drove the damaged tape south. Specialists recovered most of its contents, and a hard drive made the return journey to Los Angeles. EarthLink’s engineers worked through the night to restore access. Dayton later remembered the episode as the company’s Valentine’s Day Massacre. The name was extravagant. The margin for error had been small.

A very bad Valentine’s Day

Start here, rather than at a stock exchange, and Dayton’s career becomes easier to understand. He has founded businesses around the promise that something useful should be easier to use. EarthLink addressed getting online. Boingo addressed finding and joining wireless networks away from home. Both promises depended on unglamorous things happening correctly, repeatedly, for people who had other plans for their afternoon.

His work now stretches across internet access, education software, art, satellites and aviation. The list can obscure the work. A person trying to connect a computer has a specific problem. Solving it requires an operator as well as an optimist. That early outage supplied a rather concentrated education in the difference.

Coffee, pixels and a name on a grid

Dayton was born in New York in 1971 and grew up in Los Angeles. His father, Wendell Dayton, was a sculptor; his mother, Alice Pero, is a poet and flutist. His grandfather David DeWitt, an IBM Fellow, helped introduce him to computers. Art and technology arrived as things people close to him actually did.

He graduated from Oregon’s Delphian School in 1988 and passed on college. In 1990, he co-founded Café Mocha in West Hollywood, combining a coffeehouse with an art gallery. Two years later came Dayton/Walker Design, an agency serving entertainment clients. There were pictures to make, customers to please and, at the coffeehouse, people who expected their order.

Difficulty connecting his own computer to the internet suggested the next business. Before launching EarthLink in 1994, he needed a name. He drew up a grid of possibilities and called six friends, including his future wife, novelist Arwen Elys Dayton. EarthLink won narrowly. Corporate identity had been settled with the resources available in an apartment.

Then came a letter: a cable company already held the trademark. Dayton called its general counsel, explained the predicament and received permission to use the name, without a fee. A conversation rescued the branding exercise. Looking back, he retained a proper respect for the alternative he had escaped: “I’m glad I didn’t choose ‘WanSoft’!”

“I’m glad I didn’t choose ‘WanSoft’!”

Sky Dayton, remembering the naming of EarthLink

An invitation to Cupertino

EarthLink grew to serve millions of people. Among the customers Dayton cared about were Macintosh owners; he was one himself. In 1998, Steve Jobs invited the EarthLink team to Cupertino. Jobs had returned to Apple the previous year and was simplifying its product line.

At the whiteboard, Jobs explained a plan for four computers: a desktop and a laptop for home, and a desktop and a laptop for business. The proposal for EarthLink was equally concrete. Its service would appear as the default internet provider on Apple’s new consumer desktop, the iMac, with a wider relationship to follow.

For Dayton, the result was distribution at precisely the point a customer needed help. A person turning on a new computer could encounter EarthLink during setup. Apple subsequently invested $200 million in the company, and Phil Schiller joined its board. The relationship put a service next to the task it existed to accomplish.

Dayton also remembered a phone call from Jobs after an EarthLink public relations employee briefed a reporter ahead of an announcement. Jobs asked him to rein things in. For all the scale of the partnership, somebody was still minding the details of how it reached the public.

The internet leaves the desk

In 2000, Dayton installed a wireless network at home. His recollection of the bill is a useful antidote to nostalgia: $700 for a laptop card and $2,000 for an access point. Even the name, 802.11b, sounded like something a customer should be spared having to remember.

He expected the equipment to become cheaper and wireless networks to spread. That created a separate difficulty. A traveler might find networks in different places, yet still have to discover each one and work out how to join it. Dayton founded Boingo in 2001 to make those connections easier.

Early Boingo worked with other service providers rather than assuming one company would own every useful hotspot. Airports and hotels offered an obvious test: travelers carrying laptops wanted to collect their messages without negotiating a fresh relationship with each network. Coordination was part of the product. A wireless signal alone could not finish the job.

Dayton served as the original CEO and later chairman. Boingo went public in 2011. In August 2014, he stepped down from its board, with CEO David Hagan taking the chairmanship. It is an important distinction in a long career: the founder attached to a company’s origin need not be the executive running it today.

A founder becomes a beginner

Around the time his Boingo chapter was drawing to a close, Dayton was acquiring a different sort of competence. A friend had taken him flying in a small jet after dinner. Leaving the Gulf of Mexico behind them, he found himself wanting to learn how to do it.

First came private pilot and instrument qualifications, followed by a single-engine airplane. Then he decided to train for a jet rating. He described reading at least a thousand pages of manuals and textbooks and flying more than 150 hours with an instructor. In May 2014, a week of intensive jet training ended with an oral examination and a two-hour check ride.

His account dwells on simulated failures, instrument flying and the effort needed to perform procedures correctly. Familiar business accomplishments offered little assistance with the next maneuver. An examiner could watch what he actually did.

That experience gives texture to a later investment in Loft Dynamics, the Swiss company developing virtual reality flight simulators. Dayton became involved as an investor and board member. Here was training equipment he had personal reasons to understand, down to the uncomfortable distance between reading a procedure and performing it.

The work after Boingo

Investing had already become part of his working life. In 1999, he co-founded eCompanies with former Disney executive Jake Winebaum. Later ventures and investments included City Storage Systems and CloudKitchens, Ring, Swarm and Joby Aviation. Those roles varied; a founder’s name on one company and an investor’s name on another describe different responsibilities.

Craft Ventures now lists Dayton as a venture partner. Recent announcements give a more useful picture of his activity than the old titles alone. In June 2025, satellite navigation company Xona announced that he would join its board as part of financing that included a Craft-led Series B.

Xona’s announcement covered $92 million in previously unannounced funding, including $20 million in non-dilutive support. Its business concerns the positioning infrastructure behind the familiar dot on a map. That puts Dayton back among systems people rely on while thinking about something else.

In August 2025, Loft Dynamics announced a $24 million Series B, with participation from Dayton and Craft Ventures, among others. The company described plans to expand its airplane training offerings alongside its helicopter business, including Boeing 737 and Airbus A320 simulators. Those were development plans, with substantial work still ahead.

In April 2026, HYFIX announced a $15 million seed round led by Craft, naming Dayton among the participating investors. The company is developing American-made chips for drones and autonomous robots, bringing positioning, communications and computing functions together. The hardware has changed considerably since the dial-up era. Making the components useful together remains familiar territory.

Leave a little room for the unreasonable

Dayton’s account of his working day is less crowded than his company list. He tries to keep early mornings clear of calls, writes down what is on his mind before opening inboxes, and limits meetings. He begins an idea by writing a short story about its usefulness, then examines how it might be financed, marketed and sold. For his younger self, the advice is brief: “Read more books.”

He also surfs, plays poker and has a long attachment to Porsche cars. A 959 poster hung on his boarding school wall. At nineteen, he found a yellow 1967 911S advertised for $5,500 and paid for it by trading in his motorcycle and using his savings.

For his twenty-first birthday, he bought a 1971 911E in San Francisco for $8,500. He flew north with cash in a backpack, collected the car and drove through the night to Los Angeles, arriving with time for a nap before his birthday party. The story has the specificity that a list of investments lacks: a place, a price and a decision somebody wanted badly enough to carry out.

EarthLink’s name had once required six calls. Its damaged tape required a drive to San Diego. The Porsche required an overnight drive home. Dayton’s career contains plenty of large numbers, but some of its more revealing journeys fit on a road map.