“I hate raising money and I am not good at it…” – says Clark Benson, with a laugh. The company is growing nicely and profitably. Read on!
Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?
Clark Benson: I was born in the suburbs of Chicago, Illinois. I spent most of my life in Illinois. I went to college at the University of Illinois. I graduated college in 1990 with a degree in Finance. I was very business-focused. One interesting tidbit is that the undergraduate program at the University of Illinois is a pretty highly-rated business program.
The undergraduate program was very similar to the MBA program. There was a lot of course overlap between a Finance undergraduate and an MBA. It’s a big school with about 30,000 people in the school. I took an entrepreneurship class and it is what I remember the most from my college experience. It was about a 40-person class with a mixture of students from both the undergraduate and graduate program.
It was the only class at a very large business school that had anything to do with entrepreneurship. In 1990 when I was coming out into the working world, the resources available for entrepreneurs were so vastly less than they are nowadays. It’s fascinating to see the change over time.
Sramana Mitra: No question. It’s not only that the resources for learning about entrepreneurship were vastly fewer, there’s also a tremendous awareness and glamorization of entrepreneurship today. It’s much more natural for people to tell their community that they’re going to start their companies. People don’t flinch. I started my first company in 1994 while I was still a graduate student. It was a very different dynamic in the world.
Clark Benson: I completely agree with you. We were doing this in the pre-Internet era as well. My biggest entrepreneurial inspiration was Richard Branson who got a lot of press. I didn’t have close friends, relatives, or mentors at all for the first 10 years of my entrepreneurial journey.
Sramana Mitra: Tell me about the journey. What happened when you came out of college? What did you do immediately?
Clark Benson: I’ve always been a music fan and I wanted to get into the music industry, so I moved to Los Angeles about a year and half after college. I wanted to somehow work my way into the music industry, not as a musician but as an executive. I had my finance degree and I started working in a record store because that was the way to get to know people in the music industry.
My parents were like, “That’s not a very good use of that finance degree.” Then I got an internship for $6 an hour at a record label. It wasn’t even an internship. It was a paid temp job – 30 hours a week for $6 an hour. I took that and eventually leveraged that to a salaried job at another record label. After a total of about two years of working at record labels, I didn’t feel like I was going to be able to move ahead as fast as I could. A lot of businesses were started by simply being in an industry and seeing a hole that needs to be filled. I saw that.
I saw that record labels were spending a lot of money promoting their artists at retail stores via listening stations, which were very new at that time. You put on the headphones and listen to the CD. I built the program that tied together independent record stores with listening stations and made advertising money from the record labels. I started that in 1995. I was around 26 years old. I just went for it. I quit my job and I took the $5,000 I had in savings.
I made a very bad partnership with a manufacturer of listening stations and gave up way more of my company than I should have. I worked about 110 hours a week getting just 5 or 6 hours of sleep a night. It became a success from the beginning. I did that for a few years. I hired a person to help me with it. I eventually hired a person to run it. I just kept starting other businesses in parallel.