Ann is the co-founder of Hummer Winblad Venture Partners which opened its doors in 1989. It was the first VC firm to focus exclusively on software. Since that time, 45 of its portfolio companies have been acquired or gone public. She began her career as a systems programmer at the Federal Reserve Bank. In 1976 Ann co-founded Open Systems, Inc., a top selling accounting software company, with a $500 investment. She operated Open Systems profitably for six years and then sold it for over $15 million.

$15 million in 1982 dollars is worth approximately $50 million today using GPD per capita measure, which is the appropriate metric for this kind of thing.

From page 299 of Founders at Work: Stories of Startups’ Early Days:

When I went there, it was the first real business experience I had — although I had had part time jobs. I’d never been in a corporation, and it felt so glamorous to have a cubicle. Minneapolis is a bright city. There’s the Nicollet Mall and you were right downtown in the city. It’s like getting a job in San Francisco.

But it just wasn’t inspiring. No one was chomping at the bit. I actually can’t remember — I knew I was going to quit, but I can’t remember the moment where I thought, “I’ll quit and start a company.” I still felt very empowered, like, “This isn’t this hard a job. This is a big job and I’ve already gotten promoted once in the first 3 months and I know I can earn money. I can always come back to this, so why don’t I break out?” So the three guys from the Federal Reserve that started the company with me — one guy did quit his job and the other two took a year sabbatical, just in case this didn’t work. They held on to the safety ring.

There were not a bunch of people saying, “Start a company, start a company. Let’s do this. Let’s build something from scratch.” It’s so long ago now that I just remember the general feeling that there was very little to risk. I was somehow already fully trained for anything that might confront me. Of course, all that is false; there’s a lot of risk and you are never fully equipped to… you just have to be very adaptable. It turned out that I was adaptable. I didn’t know that until I did that, but it was just a feeling of fearlessness. “What’s the risk? What will I have to lose? I’m sure I can do this.” It was not cockiness, just that moment you feel in your youthfulness that you are sort of empowered to achieve.

I think what does separate some entrepreneurs from other entrepreneurs is we’re not handwringers. We don’t worry about the unknown. We don’t really worry about the risk points ahead. As you get older and you get more experience, you train yourself to think ahead about the risk points versus just to take the next hill. But non-risk-takers and non-entrepreneurs would have really 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.