In 1976, Ann Winblad started Open Systems, an accounting software company,
with the help of $500 she borrowed from her brother. The advent of the
microprocessor and the first affordable PCs created a new opportunity for
programmers. Winblad was one of the first generation of entrepreneurs who
figured out by trial and error what a software startup was. Six years later, she
and her cofounders sold the company for over $15 million.
In 1989, she cofounded Hummer Winblad Venture Partners, the first
venture firm to focus exclusively on software. In the years since,...

other near Summit Avenue in St. Paul. You could take classes at all these colleges.
So because I wasn’t just cemented to my own college and I was sort of
given a hall pass to anything, I said, “Well, I was planning on being a math
major, but maybe I’ll do this business major thing too. And by the way, maybe
I’ll take computer science classes.” The combination of being a math and
science person and then—instead of waiting linearly and taking the business
classes, like an MBA, later—seeing how business is applied, that...

oxymoron saying it now. The truth was that all these jobs they were recruiting
for affirmative action, if you weren’t really a competent young woman, you
would fail. There was a gap between skills and jobs because they had to hire you
and they had to hire you in stretch positions to get women populated. In fact, I
got my masters degree at night and Saturdays while at the Federal Reserve
Bank, and I was only the second woman in the whole Federal Reserve banking
system that had a masters degree. In the whole...

the next hill. But non–risk-takers and non-entrepreneurs would really have big
headaches about this. They would need some level of comfort and safety.
That’s something that we look for in entrepreneurs—that they have the
courage to do the job. That they’ll have the ability to judge the business situation.
They’ll have the ability to lead people. They’ll have the ability to interact
with the marketplace and to really build confidence into strategy.
Livingston: I read that you initially started out as a consulting company and you
would do the “real” startup project at...

fact opened up my college accounting book and said, “Let’s start programming
this from scratch and build accounting systems for smaller computers.”
Livingston: Was this before personal computers were even out there?
Winblad: They were coming really fast. Hobbyist computers already started
appearing. Now the year is 1975—remember that’s the year that Microsoft
started and Microsoft was writing Basic for kit computers. We didn’t have as
good soldering skills as probably Bill and Paul did. And we, of course, weren’t
working at the systems level writing the operating systems and languages, so we...