An Interview with Ann Winblad

Wolfson :   Who is the living person you most admire?
Winblad :   My parents.
Wolfson :   What historical period would you like to live in?
Winblad :   2050 to 3000.
Wolfson :   What talent would you like to have that you don't have?
Winblad :   A better singing voice. I could demonstrate, but take my word for it.
Wolfson :   Do you know a good venture capitalist joke?
Winblad :   I don't have a great comic delivery, but I saw this Dilbert cartoon that I thought was funny. Dilbert said, I'm starting my own venture capital firm. I'm attracted to the concept of watching people with moronic ideas beg for money. And someone says, Will you actually finance anyone? Dilbert says, That could sort of crimp the mirth. Then we flash ahead to Dilbert, the venture capitalist, and he's sitting in a restaurant with a potential entrepreneur. The entrepreneur says, "My idea is to develop a word processing program for Windows." Dilbert says, "That's an interesting concept. I wonder if $20 would be enough?" The entrepreneur asks, "To start a software company?" And Dilbert says, "No, to pay our waitress to beat you with a loaf of French bread."
Wolfson :   Do you get a lot of moronic ideas coming your way?
Winblad :   I think it's actually important not to consider any idea moronic. It takes a lot of courage to write your ideas down or to prepare a presentation and to march in here. In many ways, if you consider the idea brain-damaged, you're considering the person brain-damaged. And that person is maybe very, very smart and has a poor idea or an idea we do not consider fundable.

I look at it like blind dating. You probably have fond memories of blind dates. The concept of blind dates is very dysfunctional. But if you ever get one, you realize, I have to get through this. And so you just think, Hey, I'm not going to marry this guy or go on another date with this guy, but maybe he has an interesting brother, cousin, nephew, friend.

I think it's actually important not to consider any idea moronic.

My job is to apply my coaching skills here even if I turn this deal down and to really give the entrepreneur honest feedback about why the deal is not fundable. Hopefully, that person will reappear somewhere, either as an entrepreneur of a more fundable idea, a great employee in one of our companies, or with their smart brother, cousin, uncle, nephew, sister, whatever.

Sequeiros :   How do you feel you've distinguished yourself from other pioneers in this field?
Winblad :   I've never strayed from my commitment to the software industry. There have been a lot of pioneers who have done much more remarkable things than I have. But then they've just exited and disappeared forever. It's very challenging to stay in this industry for a long period of time. The requirement for intellectual stamina, all the time, is really high. You have to squeeze your brain every day to completely understand the pieces, which are multiplying and getting more sophisticated all the time.
It takes a lot of courage to write your ideas down or to prepare a presentation and to march in here.