Modems, Music, and Moonshots

Mike Cassidy has a résumé unlike that of any other Berklee alumnus. He is known by his business-world peers as a “serial entrepreneur” after establishing four highly successful Internet-based start-ups—each sold for a king’s ransom. Over the past five years, his deep science background led him to serve as the director of the team developing Google’s Project Loon. The ground-breaking initiative is part of an audacious plan to bring balloon-powered web service to nearly 4 billion people in the world’s developing countries that currently have little or no Internet access.

Growing up in Maryland, not far from Washington, D.C., Cassidy had high ambitions as he pondered his future and which college to attend. Like many of his generation, he was fascinated by space exploration, but having studied classical piano since the age of six and jazz during his high-school years, he also felt a tug to pursue musical studies. Ultimately, he undertook a multifaceted education that has enabled his passions for science, music, and entrepreneurial business pursuits to cross and recross at multiple points throughout a much-heralded career.

It Is Rocket Science

Cassidy earned both his bachelor’s and master’s degrees in aerospace engineering at MIT and became an Air Force reserve officer there, all while keeping music as a constant in his life. “I was in the MIT Festival Jazz band, which was a quality group that Herb Pomeroy used to direct,” he recalled during our November conversation in a Google conference room. “I was also in few rock bands and took some composition and jazz arranging classes at MIT.” Later while pursuing his MBA at Harvard he continued his musical journey. “At Harvard, I had a rock band that we called Free Beer. When we’d put up posters for our gigs, we always got a crowd.” Perhaps even then some of Cassidy’s nascent marketing prowess was shining through.

Before completing his MBA studies in 1991, he began working on what would become his first startup. Cassidy and his team built Stylus Innovation, taking five years to develop computer telephony software called Visual Voice that was acquired by Artistsoft for $13 million in 1996. With some money in his pocket, he took another look at music and enrolled at Berklee.

“I wanted to become a better jazz pianist,” he says. “I thought I was pretty good going into my ensemble placement tests, but I got pretty low scores. But that was fine. I learned a ton and found out why I was at a low level.” He also took MP&E classes and got to know the ropes for record production. “In those classes you got to play all of the roles,” he recalls. “One day you were the producer saying, ‘That guitar player is terrible!’ or ‘Let’s try a different song.’ Then the next day you were the assistant recording engineer bringing people coffee and wrapping mic cords. Then the next day you could be mixing.”

By 1998 in the midst of the dot-com bubble, Cassidy got the itch to get into business again. “I loved being in music, but that was a boom time for the Internet,” he says. “I felt I was standing on the sidelines while everyone was doing startups. I jumped in again and my second company grew to be worth $500 million in 500 days.”

That venture, Direct Hit, was an innovative Internet search engine that, among other things, brought Cassidy early contact with Google founders Larry Page and Sergey Brin during their salad days. “They were just beginning Google and we debated search engine architecture,” Cassidy says. “They based Google on page rank, boosting sites because they had other websites pointing to them. Our engine was founded on click popularity. If a lot of people had visited a site, we’d boost it. We kept track and if someone spent only five seconds on a site, we’d penalize it. If they spent five minutes on it, we’d boost it.” With help from venture capital funding, Direct Hit grew rapidly with MSN, Lycos, AOL, and other companies among its customers. Less than two years after the launch, Cassidy and company sold their venture to Ask Jeeves in 2000.

A New Game

Cassidy took another short sabbatical before diving into his third startup around 2002. That company morphed to become Xfire, a chat client that brought together like-minded online gamers from around the world. It facilitated making appointments to play others and saved screenshots of players’ game progress among other functions. By 2006, after registering millions of users, Xfire sold for $110 million.

“MTV bought Xfire, and I spent a year at MTV,” Cassidy remembers. “On my first day I met the guys in the Red Hot Chili Peppers. I also went to the video music awards a couple of times, it was a fun time.” Having success in business has enabled Cassidy to offer financial and other support to jazz and classical music entities. He met Gerald Slavet just as he and Jennifer Hurley-Wales were starting up the successful NPR old-time radio show From the Top that spotlights gifted young classical musicians.

“When Gerry was kicking it off, I gave some modest financial support and made some introductions for him,” Cassidy reveals. “The VP of marketing from one of my startup companies, Meredith McFerrin, was looking for something in the non-profit area. I introduced them and she became very valuable to Gerry. I was involved with the show from the beginning and still go to the tapings when it comes to San Francisco.” Cassidy has also served as a member of the board of advisors for Jazz at Lincoln Center in New York.

Cassidy launched his fourth startup in 2008, the travel website Ruba. With strong search and browsing capabilities, the site was designed to enable travelers to research destinations by perusing photos, travel guides, and recommendations posted by the site’s many users. Ruba was a natural for acquisition by Google, which purchased it in 2010.

“Larry and Sergey remembered our conversation from 1998 about click popularity,” Cassidy says. “After they bought [Ruba], I became the co-head of product management for the main Google search engine. I did that for a year and a half, but then got a little restless. I went to Google X, which is for moonshots. [In that division] they are looking for things that are at least 10 times better than anything else. The self-driving car and Project Loon were started at Google X.”

Connections in the Stratosphere

While Cassidy’s previous business ventures have provided desired services for millions of people, his work on Project Loon may benefit the largest number of people yet. Given his aerospace and entrepreneurial background, he was a perfect fit to lead the project. In essence, Project Loon is a network of high-altitude balloons, each equipped with a Wi-Fi modem, radio equipment, an antenna, and a small computer to provide Internet connectivity for some two thirds of the world’s population that is currently without it.

Here’s the essence of how Project Loon works. Helium-filled outer balloons raise each unit to between 60,000 to 100,000 feet into the stratosphere far above mountain tops and air traffic, and even natural disasters on earth below. There, the solar-powered balloons can sail on natural wind currents. A second internal balloon is filled with air that is heavier than helium and can be regulated to raise or lower the balloon to catch other wind currents to change its direction. The balloons traveling in clusters communicate with land-based Internet antennas at ground stations and with each other to create networks in the sky that are constantly moving on wind currents flowing west and east. By targeting specific latitudes—let’s say on the southern portion of the globe—balloons passing over portions of southern Africa will eventually move over South America. Large numbers of strategically guided balloons around the world offer the potential to provide consistent, low-cost Internet access to the people below.

While few people in developing nations own a computer, many have cell phones with Internet capability. This is where Google sees an opportunity to connect more people. “It’s a make-the-world-a-better-place kind of thing,” Cassidy tells me. “Internet access brings education, jobs, medical information, and weather reports so crops can grow better. Every 10 percent increase in Internet penetration in a country will increase the GDP by 1.4 percent per year. If you have a 20 percent increase in Internet penetration, you’re going to increase a nation’s GDP by almost 3 percent a year. So this offers a chance to raise the standard of living of half the countries of the world.”

Project Loon is a way to improve lives, but it also promises great business potential. “I don’t know what fraction of people will come on board and how many dollars they will be able to spend each month,” Cassidy states. “But when you multiply it out, you are talking about millions of dollars in revenue. So this makes the world a better place and is a good business for Google.”

Despite his day-to-day involvement refining Project Loon and traveling the world to negotiate with heads of state for permission for Loon’s balloons to pass over their air space, Cassidy keeps a hand in music. His morning ritual is to play piano works by Debussy, Schumann, or Chopin. He is also a member of a rock cover band. He views music as a gateway to nonmusical inspiration.

“Lots of people are firm believers in the overlap between intellectual talent and musical talent,” he says. At MIT, the musicians were fantastic and smart. From the standpoint of creativity, I think that what my startups were about was having both a creative idea and creative ways of executing. I oftentimes find some music-related experience helps with that. I’ll be listening to music while going for a run or when I’m sitting in my house, and that will trigger something. I keep a pad of paper by my piano so I can stop and write down the ideas that come to me. Improvisation is creating music in real time, but I think through improvisation, you create other ideas and solutions. There is some link there.”

He recommends Reid Hoffman’s book The Start-up of You for young musicians. “It’s about taking responsibility for your career and thinking of it as a startup. Artists need to be entrepreneurs, market themselves, have a roadmap, and a product.” Cassidy sees tremendous opportunities for today’s musicians. “Because of the [Internet] distribution channels, you can reach 10 million people in a month. Look at the number of YouTube videos that go viral. Before, you needed a record company to reach that many people. But even they couldn’t do it in a month.”

Anxious to get back to his entrepreneurial roots, Cassidy recently passed some of his leadership duties for Project Loon to a new director. Dedicated to Loon’s success, Cassidy will remain engaged, but is currently planning to launch his fifth startup. “I haven’t announced what it will be yet. I hope to make an announcement before the middle of 2017.” For Cassidy, the sky is no longer the limit.