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James Sherman is a serial internet entrepreneur, and an active angel investor in New York startups. He sits on the board of HBS Alumni Angels of New York, and is[…]

Jim Sherman weighs in on his experiences as an entrepreneur, and who his role models are.

Question: What are the challenges of being a gay entrepreneur?

James Sherman:  In terms of being a gay entrepreneur, I can't say that it's been a hindrance in any way.  You know, especially in my case, I've worked in the media business for 20 years or so, and I think that in many respects certainly that industry is very open and a lot of openly gay people in it, both on the business side and the creative side.  So I don't believe that it's been a hindrance at all.  Prior to the company that I started recently, Sherman's Travel, I had started an Internet strategy consulting firm, West End New Media, doing Internet strategy consulting during the boom years of the '90s.  And being gay actually was an asset, because I was able to contact a lot of other gay people that were in senior positions, and we were able to do some terrific projects with them.  So I don't think that it's been a hindrance at all as being an entrepreneur in my case.

Question: In your industry, are there advantages to being gay?

James Sherman:  In terms of advantages, I think aside from the fact that gay people in general tend to be more creative, and I think therefore by surrounding oneself with other gay people you're more likely to be surrounded by other creative people -- is a positive, especially when launching a new business.  I think that talking with your friends, getting their input, helping you with some of your own little research with friends and family -- that's very important early on when trying to start a company.  And I think gay people do have a lot to say, and I think we tend to think very creatively.  And so I think that is an asset in general.  And then, of course, organizations like this -- StartOut, of course.  It's great for networking.  There's the gay MBA organization as well, and so I think these are excellent networking organizations to tap into.  Certainly I would say that being gay does have perhaps one downside, which is that one is less likely to be playing golf, you know, with the buddies, or joining a country club or really being in the circles where a lot of other straight senior executive types -- where you might find them.  So I think in that sense there could be a little bit of a negative aspect there.  But I think the other gay organizations can counterbalance that.

Question: Who is your favorite gay business icon?

James Sherman:  In terms of a gay icon in business, that's a tough question.  I would say probably an executive, a senior executive who I admire very much, David Stewart -- he was the COO at Martha Stewart Living.  He actually brought me over to launch the Internet business for Martha Stewart, which is where I really got my big start in online.  I think David's amazing, and both as a leader of mature businesses, but also having been involved with a number of startups.  So I think that he is someone I do admire greatly, and he clearly has amazing talents both in launching new ventures as well as managing large existing ones.  Those that are not gay, I would say that I admire -- Steve Jobs, for example, I think with Apple has done an amazing job on multiple occasions in terms of reinventing that company and competing very well in the marketplace, in particular because he in the early years was up against IBM.  And Apple has had a much lower R&D budget, but they've been able to spend it much more wisely, clearly have better product directors, and are able to innovate in the most amazing ways.

Recorded on October 30, 2009