Video of Kaplan's address to the graduates of the Class of 2014.

By: Diane Stirling
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In a speech sprinkled with humor and humility, Philip Kaplan, ’97, once a student at the School of Information Studies who has become a highly successful serial entrepreneur, came back to deliver the 2014 Convocation address and to provide some interesting life lessons.

The gig as a graduation speaker was ironic, said Kaplan, an avid musician as well as a highly skilled information technologist. As a high school student whose academic performance was sporadic, he said his parents worried that he might not even graduate high school, much less college. Still, he’s been able to find a place for himself in the world of information technology by creating it on his own terms, founding several highly successful companies, creating a number of apps, and writing a book about the boom and busts, all while continuing to innovate. The key to that success, he told the graduates, is that he has followed his own instincts rather than taken the advice of others.

Kaplan recounted how he came to be an entrepreneur. He began working in IT as a project manager at a web design firm, but before long, decided that he really wanted to go into business for himself. For many people, he recognized, that desire comes from “a passion that they just can’t shake,” the concept and “independence of being their own boss,” or an interest to “make money and change the world.” Kaplan’s goal was simpler: “I just hated waking up early.”

So he quit his job without clients of his own, but proceeded to hustle up some business. He posted his resume on job boards for web design work, and when recruiters called, he told them he wanted to freelance the work instead. He also “told everyone I knew about the work I could do. I told my friends and my relatives and their friends and their relatives.” Within six months, at age 22, those efforts resulted in his having a firm with five full-time employees and “more business than I could handle,” he said. Since that point, Kaplan has had astounding success, starting “many different kinds of companies and employing a lot more people.” He said he still wakes up every day, “thankful that I get to do what I do.  But it all started because I wanted to sleep in,” he joked.

In addition to suggesting that students listen to their instincts, Kaplan advised them to think about their work like art and to strive to be prolific. He has created about 100 different products, apps, websites, online services and companies, some that became big, some that were acquired, “and many that went nowhere,” he said. Most of them started out as hobbies, activities he began “to avoid real work, so none of it feels like work, it feels like art.” He suggested that graduates regard their work much like a musician who is putting out an album. “You’re going to have some hits and you’re going to have some duds, and the duds aren’t that big of a deal. If you’re working on something and you decide midway through that it sucks, paint over it and start again.”

The entrepreneur described how he had once spent nearly a year building a product, then scrapped it because he felt it wasn’t good enough. “That’s called quitting, and that’s OK,” he said. “You can start as many jobs or companies or products as you want.  If anyone ever tells you that it's bad to jump around or that you need to focus on one thing, that's not true.  Don't listen to their advice.”

His next piece of advice, he laughed, was not to take other peoples’ advice.  While mentors and experts are important to a budding career, he suggested that graduates listen to the stories those people have to tell about their work and their successes, but to act on their own instincts. “I always try to surround myself with people who inspire me,” he noted, “But it took me a long time to realize that I should stop listening to their advice and only listen to their stories.” He illustrated that comment. “Every regret I have in business is because I took somebody else's advice rather than going with my gut.” The problem was not that their ideas didn’t work out, he said, it was because he didn’t pursue his own ideas instead. “And for a creative person, happiness isn’t whether you made the right or wrong decision, it’s that you made your decision, and that you realized your vision.”

Thinking back to the moment he decided to quit his job, Kaplan told the graduates, “I thought it would be fun to see how far I could get. You guys are just starting; and whether you want to go into business for yourself or not, think of all the people you want to be like. And think of their stories. And see how far you can get.”

Kaplan has cofounded and sold several Internet companies, including the largest privately-held ad network (AdBrite), TinyLetter, an email newsletter service (acquired by Mail Chimp), and PK Interactive, a web consultancy. He also founded Blippy, a venture-backed social shopping company, and created several popular iPhone apps. He is now working on two music-related ventures, Fandalism, a social network for musicians to share their work and interact with other artists, and DistroKid, a service that allows musicians to easily publish their tracks to online marketplaces. He also is a bestselling author of a 2002 book that chronicles some of the major disasters of the late 1990s and early 200s tech boom. 

Kaplan was a member of the iSchool’s Board of Advisors from 2006-2012, and has hosted several groups of students who visit with him during the School’s Spring Break in Silicon Valley trips.