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Vault Q&A: Interview with Jonathan Roosevelt, CEO of Kapoof!

By Corey Hajim

Sure I am taking Entrepreneurial Management, and yeah, it's great. My professor introduces us to new entrepreneurs every class - risk takers, out-of-the-box thinkers, visionaries and some guys that just got lucky. But entrepreneurs aren't a bunch of untouchable characters off in case land, we have many future entrepreneurs in our midst. People are itching to graduate and start their own pie factory, deciding what flavors are the best, how many to bake, how thick or thin the crust should be, how much butter to use and how big their piece will be at the end of the day. Some students just can't seem to wait any longer; they want their piece now. We often hear of students leaving after a semester or the summer because of an ephemeral opportunity that is too good to pass up. It is understandable. We are here to gather the tools to realize our dreams, so if the dream swings by and offers us a spin around the block, it can be tempting.

But would you quit school just a few months from graduation? What kind of nut would pass up a diploma from HBS that is practically on the warming rack?

I wanted to find out so I sat down with Jonathan Roosevelt, former 2nd year, recent HBS dropout and CEO of Kapoof!.

Corey Hajim: What made you do it?

Jonathan Roosevelt: Do what?

CH: Drop out.

JR: Well, let me ask you a question first.

CH: Hey, who's doing this interview? Well, ok.

JR:Why did you dye your hair red?

CH: That's a question I've been getting all day. To be honest, I was bored. I'd been thinking about doing it for a long time. I think the conservative and somewhat serious nature of the HBS environment makes me do things to rebel, take chances, test the definition of who I am.

~ JR: I may have dropped out of school for a similar reason. There's an analogy here. I have always wanted to be an entrepreneur. Nothing ever excites me the way the idea of running a business does and I felt like I had waited long enough. I worked in VC to prepare myself to be an entrepreneur, I joined Netscape to get operations experience and then I came to HBS, to even further my preparation for what I actually wanted to do. I think HBS helped me discover who I am and what I really want out of my life, it pushed me to seek my real goal.

Of course, I would not have dropped out of HBS if not for a tremendous opportunity. I spent 4 years investing in Internet companies in order to learn how to identify great potential and I am confident that I have found a situation that fits the right criteria and has a an incredible team and group of investors. Of course, if we could have compelled some HBS professors to invest...

CH:What can you tell me about your company? What's this Kapoof! thing all about?

JR:We're pretty much still in stealth mode, what I can tell you is we're a new type of intelligent web agent company. Our technology will amount to a revolution in e-commerce.

CH: Um, excuse me?

JR:Yeah, I know, that's a little vague, but like I said we're in stealth mode.

CH: What excites you about Kapoof!? Is it the product or the entrepreneurial role that you play?

JR: Motivating and inspiring people is what I like to do. I get really excited about building and managing a team. I think the Kapoof! opportunity is exceptional from a strategy perspective, but underneath it all, the best part for me is that I am intimately involved in helping people reach their potential.

~ CH: Why Kapoof!? What kind of name is that?

JR:It means magic... and the domain was available.

CH: When did this all begin?

JR: About 2 years ago in the brain of our CTO. When I met the CTO, I thought to myself, this is the guy I always looked for when I was on the other side at Battery Ventures. He is a brilliant engineer, but also understands markets and applications. I met him through the HBS entrepreneur web site and, after flying to Silicon Valley to do some due diligence, I jumped on board. The coding began in August and we just completed our first round of funding, from venture capitalists and well-connected individuals.

CH: Do you think that your education at HBS has prepared you to take this leadership role? Any particular classes that readied you for entrepreneurial greatness?

JR: Running and Growing Small Businesses is a great class. I remember this guy Jim Sharp who came to speak to us about his experience as an entrepreneur. He inspired me and taught me a very important lesson that I use in my organization. He said that he could never have grown a company if he had micro-managed people. I believe that's true and I try to let people do what they are paid to do.

And LEAD of course, it's all about LEAD.

CH: Do you think being an entrepreneur is all that it's cracked up to be, or is the rumor true, you actually have to empty your own garbage can?

JR: It is already more than I ever imagined. It is the best thing I have ever done, but yeah, I do takeout the trash and I post flyers, write job descriptions, update our lousy web site and answer phones. But the menial work is far outweighed by the tremendous satisfaction I get from being a part of Kapoof's team and playing an integral role in helping an organization and its people grow.

~ CH: This is your chance to make a serious plug... I see you're recruiting interns and full-time staff. Why should I work for you this summer?

JR: Because we have a cutting-edge technology backed by top-tier blue-chip investors, an autonomous work environment, office space in an old firehouse, a rec room with foosball, cool people and a CEO that is seriously considering dying his hair purple. E-mail me at jr@kapoof.com.


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