Jason Kilar, the founding CEO of Hulu and CEO and co-founder of his newest venture Vessel, likes to point out that serendipity and luck have played a big role in his success. Take his introduction to the world of entrepreneurship. He arrived at HBS in the fall of 1995 when the school was just beginning to embrace the nascent Internet. Kilar’s class was the first to be given an email address—in this case, an AOL address because HBS addresses did not yet exist—and access to the Web. In a second-year class taught by Jeffrey Rayport, Kilar learned about the early rumblings of a still untested Internet commercial marketplace. Rayport called the class “Managing in the Marketspace” and through one of his cases, he introduced a relatively unknown Seattle-based online bookseller named Amazon.

Kilar recalled spending countless hours discussing startups and new ventures with Rayport, expressing a desire to start his own media and technology company someday. Rayport told him about the Amazon case and mentioned its founder, Jeff Bezos. “He seems very sharp,” Rayport said. “Why don’t you think about working at an existing startup for a year or two and learning a bit before you do your own thing?”

When Rayport’s class convened in Aldrich Hall to discuss the Amazon case, Bezos sat in the first row and listened as most of Kilar’s classmates predicted the likelihood that Amazon would fail. Given that Amazon was then a two-year old startup with less than 100 employees, Bezos was unknown and unheralded. When he got up to close the case and give his point of view, he laughed out loud and told the class that he completely understood their belief that he would fail. But he was clearly undaunted by their dire prognostications.

Later that same day, Kilar interviewed with Bezos in a professor’s office, flew to Seattle a week later, and accepted a job offer on the spot. He thought he would stay for two years but he spent the next nine years working alongside Bezos whom he called “the single greatest business leader of the last hundred years.”

Such praise emanates from Kilar’s experience ingesting the countless business lessons he said he learned from Bezos. “I was so lucky to have him as my manager and I did my best to observe and listen and soak up the many lessons he taught each day,” Kilar said.

What were the most important lessons you learned from Jeff Bezos?

He takes a long-term approach which is something very rare in the public markets. He is thinking decades out as opposed to quarter to quarter. He also has a simple and consistent model: which is you start from the customer and then you work backwards. Most companies do it the other way around.

What was the catalyst for Hulu?

When a little company named YouTube, which was created in 2005, got acquired by Google for $1.6 billion 18 months later, that was a cataclysmic event. It was particularly resonant in Hollywood where a lot of executives realized that there was something going on on the Internet specifically related to video. Peter Chernin at Fox and Jeff Zucker at NBC started talking with me about working together to do something on the Internet and be proactive about video. We spent a lot of time talking in the spring of 2007 about creating a fully separate company with its own culture and structure. We decided that ultimately Hulu was going to be a place for very premium content. I had written the business plan for Amazon to get into video back in 1997 and ultimately, I was responsible for the books, music and video businesses at Amazon. So I was on their radar.

Hulu has grown into a $1 billion business with more than six million subscribers. Getting that first success is tough enough. What makes you want to be a serial entrepreneur?

You need to constantly remind yourself that most of the time, these things don’t work. For the right kind of person, it is very motivating because you don’t take anything for granted. You are constantly neurotic about the need to serve customers better than anyone else. I know the pressure is on and I like that kind of environment. I take pride in that I always like to take the path less traveled. For some reason, that is very motivating to me. When I came out of undergrad at University of North Carolina, everybody else was going into investment banking and consulting, and I was writing comic strips to try to get the attention of Michael Eisner and the leadership at Disney.

What is Vessel?

My co-founder Rich Tom and I observed that the audiences so coveted by traditional TV were gravitating toward a new generation of digital storytellers. Many of these voices have become brands in their own right and have built passionate audiences that rival the size of the most popular shows on network and cable TV. But to date, there hasn’t been a clear path for most of these talented creators to build sustainable, enduring businesses on the basis of their video storytelling alone. Vessel provides early access to the web’s best short-form videos for $2.99 a month. And we are offering unusually attractive economics for the creators, up to 20 times the levels earned from free, ad-supported distribution.

Are the management issues the same for every startup or is it different with Vessel than it was with Hulu?

There are some things that are consistent, even back to my days at Amazon. And there are other things that are completely new and different. The things that are consistent, or should be, are your values and principles. They are hard to change, like the stripes on a tiger. I thank my mom and dad for the values and principles I have. What is fundamentally new and different are the challenges you encounter because of the timing and the landscape in which you are starting the business. There is also the business model and the opportunity. What we’re doing with Vessel is actually very different than what we did with Hulu.

Explain.

With Hulu, we were trying to take traditional format television and film, and distribute it through a second window on the Internet. That was a very big deal in 2007 and continues to be a big deal. What we’re trying to do at Vessel is, in many ways, to look at the entirety of the Internet and create something that we think the Internet is missing, which is a first window.

What is the goal with Vessel?

By creating a first window, we can elevate the quality of video overall on the Internet. A good analogy is what I think is one of the single biggest events in the history of media over the past hundred years, which was the introduction of pay television. That was in 1979 and the laying of cable across America enabled the creation of ESPN, MTV, the Discovery Channel, HBO, AMC, FX and all the rest. All these things would not exist if not for the emergence of cable and satellite and ultimately fiber-based television. We believe we have the opportunity to reimagine that moment in media history and do it for the Internet. That’s what Vessel is about. It’s daunting and very ambitious but we’re just foolish enough to try it.

You credit your family background for a lot of your success. Explain.

I grew up in Pittsburgh and my father was an electrical engineer who worked for Westinghouse. His entire side of the family was about technology and science. On the other side, I had this crazy mom who was trying to kill ‘em in the aisles with jokes about our lives. She wrote a humor column for the local newspaper called Eight is Enough, which was all about our family of eight. I was the fourth of six kids and wherever I went in town, everybody would know my life. And this combination of storytelling and the sciences clearly influenced the choices I’ve made.

Did you have a cathartic moment when you knew you wanted to be an entrepreneur?

I actually think I can pinpoint that moment. When I was ten, we piled into the family cargo van, a Chevy Beauville, and drove from Pittsburgh to Orlando, Florida. It was our first real family vacation and we were going to Disneyworld. I remember getting to the parking lot and walking the tunnel that gets you into the Magic Kingdom and seeing Cinderella’s castle in the distance and it had a profound effect on me. I had never seen storytelling done at that level of execution. I had never seen design done with such obsessive attention to detail and at that moment I wanted to find out as much as I could about who created all this. I’d watched Disney movies and all that but I now had a passion and desire to find out about Walt Disney, the entrepreneur. So much of my middle school and high school years were about understanding who Walt Disney was and what motivated him. In many ways, it led me to a very entrepreneurial venture, which was Amazon, and then to help build and grow Hulu, and ultimately to Vessel. Walt Disney’s entrepreneurial thread is common throughout all this.