So there’s been business and entrepreneurship in your family?
Going back a lot of generations. My great-grandfather started a company called the Shuttle Paper Box Co., which was one of these paper-box manufacturers way back in the day back when it was a big deal.
That was probably tech back then.
There’s a lot of true innovators in the family.
What was your first Internet-related business?
I built a Web development agency in college. I moved down to L.A. (in 1998) because my wife got into grad school down here. There were a series of early adopters in business who realized the Web was a great platform and they got excited about it. Whether they knew what it was going to do to their business I can’t say, but they wanted to be involved.
What was L.A.’s tech scene like at the time?
It was a tiny field and there wasn’t a formal venture capital community. Venture was very Silicon Valley based at that point. But we bumped into bankers coming out of Goldman Sachs and they invested early stage with us. The original investors were very seasoned older bankers in real estate and that was L.A. There wasn’t a big community for us to tie into.
When the Internet bubble burst, did that hit you guys?
I had ended up in a difficult partnership. I chose to sell my equity in the business and within 90 days the market fell out. The company imploded really quickly.
Was there one day when you realized it wasn’t working anymore?
I watched from afar as things started imploding. Then I set up a new company, it was a little agency that later became Userplane, a company that I built and later sold to AOL. Userplane is still at AOL and some of my core team still is there running the business. I would be first to admit it never became an explosive business, but it’s still around. I’m baffled on how it’s survived.
You were at AOL after the merger with Time Warner in 2000. What were things like during that period?
You have to remember when that deal happened the thought was AOL is buying Time Warner. It was called AOL Time Warner. But I would say Time Warner was not happy with the way AOL impacted their top line.
Did that deal sour the relationship between media and tech?
There’s been a culture clash between media and tech. I think we all know how to dance with each other now, but that’s taken a long time. At the end of the day, the digital industry is a media business and it’s very disruptive. Whenever you have these transitions happening they’re rarely smooth because you’re taking something that’s really big and built on a lot of structure that’s very mature and you’re having a disruptive force come in and break up a lot of the structural elements of those historic businesses. I’m not sure the record business will ever be the same.