Sky Dayton

American entrepreneur and investor Sky Dayton is best known as the founder of EarthLink, an early internet service provider that helped revolutionize internet access for millions of customers. Currently, Dayton is an active investor and board member at several companies.

Dayton was drawn to entrepreneurship early in life. He credits his parents for encouraging him to follow his dreams, even if that meant going against conventional wisdom.

For example, In 1990, when he was just 19, Dayton co-founded a fusion art gallery/coffee house in West Hollywood. And just two years later, he founded Dayton/Walker Design, a forerunner in digital graphic design. Dayton/Walker Design worked with some of the biggest companies in the local entertainment industry, including Sony Pictures, Warner Brothers, and Disney.

After his first frustrating attempt to access the internet, Dayton founded EarthLink in 1994 at the age of 23. He envisioned a low-cost internet service provider (ISP) that would broaden access to digital spaces and help democratize flows of information.

Focusing on reliable customer service, simple pricing, and user-friendly software, EarthLink grew rapidly through the mid-1990s. Within a few years, it was the largest independently owned ISP in the United States, with more than 5 million customers and $1 billion in annual revenue. EarthLink made its NASDAQ debut in 1997 as one of the year’s highest-profile tech IPOs.

In 1998, Dayton and Apple founder Steve Jobs inked a strategic partnership to make EarthLink the default ISP for iMac users ahead of the groundbreaking personal computer’s debut. EarthLink proved integral to iMac’s runaway success, and Apple ultimately invested $200 million in the company.

In 2001, Dayton founded Boingo Wireless, the first solution to effectively amalgamate global WiFi hotspots into a unified network. Dayton took the company public in May 2011, raising nearly $80 million, and served as chairman until August 2014.

Dayton’s investing career began in 1999, when he partnered with Disney’s internet division to establish eCompanies. Dayton and cofounder Jake Weinbaum envisioned eCompanies as a hands-on business incubator and venture capital fund for early-stage internet companies. Notable eCompanies successes included Business.com (sold for $345 million), LowerMyBills.com (sold for $380 million), and JAMDAT Mobile (ultimately purchased by Electronic Arts for $680 million after a successful IPO).

Dayton remained an active advisor, investor, and board member after leaving eCompanies. He has played a key role in notable firms including Ring (which ultimately sold to Amazon), NeoPets, and Joby Aviation. In 2016, he co-founded City Storage Systems and CloudKitchens.

More recently, Dayton led the Series A round in Swarm Technologies, which leveraged tiny satellites to develop the first global IoT network and was acquired by SpaceX in 2021. Also in 2021, Dayton led the first institutional funding round for Loft Dynamics, which developed the world’s first VR plus full-motion flight simulator for aviation training.

Sky Dayton lives in the Pacific Northwest with his wife (the best-selling novelist Arwen Elys Dayton) and their three children. When he’s not working with his portfolio companies or surfacing the next big idea, he enjoys surfing, playing poker, and aviation as a jet-rated pilot.

What is your typical day, and how do you make it productive?

First, I try to keep my early mornings free of calls or meetings at least until 10 or 11 a.m. I start the day writing down everything on my mind, ideally before I look at my various inboxes. This helps me organize my thoughts and goals for the day. Following that, I get through my email and messages.

Second, I minimize meetings however possible. Meetings are less necessary when you work with competent people. I have lots of short bursts of communications with individuals and with groups. And occasionally, of course, I have larger meetings for brainstorming or coordination, but these are the exception, not the rule. The rest of my time is spent on research. I read a ton.

How do you bring ideas to life?

I start with a short story about an idea and think about how it will benefit customers and the world. I explore the economics of the idea, considering how we will market, fund, and sell it. This process forces me to confront all the reasons it won’t work. There’s no hiding. Then I work it over and over until it seems like something inevitable. That’s the test. At that point, I know if I don’t do it, someone else will.

What’s one trend that excites you?

I’m fascinated by the coming advances in day-to-day transportation. For example, look at what Elon is doing with tunnels (and rockets, but that’s another discussion) and what companies like Joby are inventing in electric vertical takeoff and land (eVTOL) aircraft. Our lives are organized around transportation. Our cities are built based on assumptions inherent to cars, buses, and rail. What if we could unlock the space below and above us?

What is one habit that helps you be productive?

I try to finish work once I start it. If I open an email, I try to read and respond right away before starting another task.

What advice would you give your younger self?

Read more books.

Tell us something you believe almost nobody agrees with you.

Poker is actually a sport. Competing at the highest levels of poker requires incredible mental and physical stamina. And it’s on ESPN!

What is the one thing you repeatedly do and recommend everyone else do?

Cold plunges.

When you feel overwhelmed or unfocused, what do you do?

If I’m overwhelmed at work, at a poker game, or anywhere else, I go for a walk.

What is one strategy that has helped you grow your business or advance in your career?

I spend most of my time making sure I’m working on things that align with my purposes. With that in place, the hard work is easy. The rest sort of takes care of itself. It’s much more about the “what” than the “how.”

What is one failure in your career, how did you overcome it, and what lessons did you take away from it?

I was convinced by others to start a company, and before I knew it I was its CEO. Seemed like a good idea at the time, but it wasn’t really my own purpose, and it was hell. We made it work for a while, but in the end, we sold it for a fraction of the money we’d invested. I learned how important it is to be playing the right games of my own choosing, not those presented by others.

What is one business idea you’re willing to give away to our readers?

Always be learning, and pay attention to disruptive technologies and their implications. The commercial internet rewired daily life and created opportunities for billions of people. What’s next? AI will change everything in education and every aspect of life. Fusion, eVTOL air taxis, space travel — these advances are in front of us, and they will unlock trillions of dollars in new businesses.

What is one piece of software that helps you be productive? How do you use it?

The Eight Sleep mattress is a game-changer. I sleep better, and that levels-up everything else.

What is the best $100 you recently spent?

Twitter Blue subscription. Incredible how good the content is on Twitter these days.

Do you have a favorite book or podcast from which you’ve received much value?

“Atlas Shrugged,” by Ayn Rand. I first read this book when I was 16 years old, and it affected me deeply. I’m reading it again now. It’s truer today than ever.

What’s a movie or series you recently enjoyed and why?

“Arnold” on Netflix. Schwarzenegger is an inspiration to anyone with ambition.

Key learnings:

• The games you choose to play in life are the most important decisions you’ll ever make
• Everything else is easier once you’re working on something that aligns with your own purposes
• Never stop learning
• The future is bright! We live in a special time, take full advantage of it