An Interview with Ann Winblad
Photo of Ann Winblad

Interview by Jill Wolfson, San Jose Mercury News; and Carla Sequeiros, Mt. Pleasant High School

Interview photos by Len Lahman, San Jose Mercury News

Transcribed by Jean Ricket, Tech Museum volunteer


Carla Sequeiros

In 1976, Ann Winblad started a software company, Open Systems, which she sold "for a pile of money." She then went ot work as a consultant for Microsoft, Apple and I.B.M..; wrote a book on object-oriented programming and co-founded Hummer Winblad Venture Partners, a $95 million software-only fund, headquarted in Emeryville.

While she will probably be forever known as the one who once dated Bill Gates, Winblad is also known as one of the toughtest and most savvy investors in Silicon Valley. She serves as director of, among many companies, Arbor Software, Berkeley Systems and Net Perceptions. She is also an advisor to The Software Forum, the San Jose Center for Software Development and the Stanford/MIT Venture Forum.

Sequeiros :   What kind of student were you? What motivated you towards computers and software?
Winblad :   I was a really good student. My dad was the high school football and basketball coach. Either you're a terrible student when one of your parents is at school all the time, or you're a great student. My parents set a high value on education. From the beginning, achieving good grades and doing well in school was something that my parents really liked. So as a youngster in primary school, it was really exciting to come home with a great report card and be really motivated to learn more.

I grew up in a really small town, called Farmington, Minnesota, where there were less than 3,000 people. There were only 110 people in my graduating class. I was the class valedictorian.


Either you're a terrible student when one of your parents is at school all the time, or you're a great student.

I also was cheerleader, which is an unusual combination. I was very active in all sorts of school activities. I wasn't very nerd-ulent, and did not even use a computer until I went to college. I was very good at math and physics and all the sciences. But I also enjoyed the liberal arts type courses as well.


We didn't even have a computer science major. At that time, Stanford's computer science major was a liberal arts major. Amazing!

I went to a small college called the College of St. Catherine and the College of St. Thomas, part of the 5-college group in St. Paul, Minnesota, which includes Hamline and Macalester and Oxberg College as well. Combined, there were maybe 7,000 students.

Control Data had heavily endowed St. Thomas College with lots of computers. So we had more computer time than anyone, even at the larger colleges. That was the first time I took a programming class. We didn't even have a computer science major. At that time, even Stanford's computer science major was a liberal arts major. Amazing! Once I figured out that there was such a thing as a computer and that programming was so much fun, I was cornered.

Sequeiros :   I find it really interesting that you got into the business of computers and software very early when computers were just breaking through. What piqued your interest?
Winblad :   In college, I was on a special 4-year program, and I was called an experimental student. They let 25 students take any courses they wanted without any prerequisites, which meant that we could get through the majors pretty quickly. So I also got enough room to take all the computer sciences courses that were offered.

It was very unusual for women to be taking any of these courses and it was a big year of affirmative action. So all sorts of job offers were given to me as soon as I graduated. I was given a job offer to run a small plant for 3M Corporation, a job offer to work for the government -- I think it was either the FBI or the CIA where you went after people who were guilty of tax evasion. Most of the jobs offered to me were way above my capability and not in my interest.


I didn't want just a job. I wanted to do something where you actually could create something, where it was really exciting. So after 13 months, I resigned.

One of the jobs I was offered was as a systems programmer at the Federal Reserve Bank in Minneapolis. Now that doesn't sound very glamorous, but the Federal Reserve Bank did not normally hire inexperienced people. And it was a government-graded job where you started at perhaps a Grade 7, and I would be brought in as a Grade 10, so it was pretty high up. It was a brand new building in big downtown Minneapolis. So I took that job.

It was extremely boring.

One of my cubicle mates would disappear from 2 to 3pm everyday. And, finally, after I worked there a few weeks, I asked, where are you going? And he told me: `I go home and watch `I Dream of Jeannie' on TV. Nobody ever missed him. Nobody got there any earlier than 9 a.m. And at 5 o'clock, everyone was gone home, no matter how exciting the project was or how much work was ahead.

They were just checking in and checking out. There was no commitment to build anything, no commitment to the products we were looking at. It was a job. And being sort of an overachiever myself, I didn't want just a job. I wanted to do something where you actually could create something, where it was really exciting.

So after 13 months, I resigned.

I had this idea that basically most entrepreneurs really overestimate what is required to start a company. Hey, I knew how to program. I took all those business courses. The business majors seemed not as smart as the math majors. They all came from families that had run businesses before. How hard would this be?

So I actually convinced three of the top programmers from the Federal Reserve Bank to start a company with me. Those three guys would not quit their jobs. They took a 1-year sabbatical just in case it didn't work. One was actually my boss, who supervised the projects that I was involved in.


I actually applied for food stamps that first year because I could qualify.

So we started a company in 1975 and formally incorporated. It was called Open Systems, a name used quite frequently today to describe standards and systems architecture.

I actually trademarked that name in 1975.

I said, "Why don't we build a high-end accounting system for these new, smaller computers, called microcomputers." (They weren't called personal computers then.)


It wasn't like "Nerds Rule," like it is today. It was very fringey.

We did that at night. During the day, we got a large consulting contract to get paid by the hour to build some software for a large school district nearby. That gave us the money to pay our rent and pay our bills while we were building this software.

I actually applied for food stamps that first year because I could qualify. So I would go to the grocery store and buy all the food and bring it to the office, and then the guys would take it home and eat it.


My parents thought I was off on some `finding myself' expedition, and I would come back soon and do something real in the real world.

At that time, there was a very small software industry, not like today. It was really considered very unusual to be a professional nerd at that time-and not a positive thing. It wasn't like "Nerds Rule," like it is today. It was very fringey. My parents thought I was off on some `finding myself' expedition, and I would come back soon and do something real in the real world.

Wolfson :   This was risky?
Winblad :   Well actually, I was very young and I had nothing to risk. I had no money. I didn't own anything, not even a car. So why not give this a try? Could I work for myself? Could I convince other people to work for me? Could I help define a product? Could we build a product and then could we convince customers to buy it? We lost $85 the first year which caused my partners to be slightly panicked.

As I know now, it's very difficult to make money your first year in business. You're mostly building product versus selling product. So to end that year with just a $85 loss wasn't so bad.

The thing then was that we had to learn every aspect of the business ourselves. We didn't have any business advisors who'd done this before. There was no thriving software community in Minneapolis. It was the same year that Microsoft got started and Digital Research was happening in Monterey. There was not a Mesopotamia of software companies.

Sequeiros :   How do you feel that being a woman has helped or hindered you in business?
Winblad :   I've been very lucky that I picked the software industry to pursue as my career. It is really an industry that's based on meritocracy. Of all industries that I've had a chance to intersect with, it seems less hostile towards women.
Sequeiros :   What do you look for when you invest in a company?
Winblad :   First, we invest in markets. If the opportunity is not large, then the business, independent of the people or the technology, will fail. Because of this issue of intense competition and capital efficiency, opportunities always get smaller as soon as you fund the company. There's competitors you don't know about. The entrepreneurs are mostly first-time CEOs, so they will make mistakes and clip the wings on the edges of their market themselves. So it better be large to start with.

I was very young and I had nothing to risk. I had no money. I didn't own anything, not even a car. So why not give this a try?

Number two is: I look at the founders. Who is the CEO? Can they attract excellence? Here in Mesopotamia, Silicon Valley, we have negative unemployment right now. And that doesn't show much opportunity for change in the near future. Which means, if you start a company, in order to get your engineering team staffed, to hire your other executives, you've got to get people to leave other jobs. So we look at your ability to attract excellence. Will people want to come and work for you? And can you convince them that your opportunity is better than others?

Then we look closely at the products and technology to see if what you're going to deliver to market can at least for the foreseeable future deliver a sustainable competitive advantage.


We lost $85 the first year which caused my partners to be slightly panicked.

Then we try to work as a trained coaching staff and trained networker to help you avoid the mistakes that I made as an entrepreneur or other of our companies have made, and to provide you with the connections.


Our job is to audition the future...we get to pick which parts of the future we think are going to happen and to give them money after they convince us they can own that.
Wolfson :   Think of yourself as a futurist for a minute. You see so many ideas coming in. Where is the energy now in the field? Where are we headed?
Winblad :   It used to be that you could talk about the software industry as `this happens, then this happens.' We're going to have desktop productivity applications and then everybody will be happy campers. But it is a very complex and sophisticated and large industry that covers many layers and many domains. All the cylinders are firing simultaneously. So let's just talk about some of the central themes that really, if you squint, you can start to see companies coming in with. Our job is to audition the future. It's a really fun job, because we get to pick which parts of the future we think are going to happen and to give them money after they convince us they can own that.

If you start a company...you've got to get people to leave other jobs.

We've gone through eras and eras of data creation. Transaction processing was one of the first software areas. That's why we built accounting software. That is transaction processing. As we moved from stand-alone mainframes to local area networks to client-server, most of what has been installed in the customer base is still for transaction processing.

We're just starting the era of what we'll call analytical processing. As the enterprise is extending beyond even the barriers of the buildings themselves for major corporations, for individuals, information plays a much greater role.

What is that data? How does that data provide us with some kind of analytical view of our companies? That will be a big change. Most people haven't noticed it yet, and they're still thinking about database-intensive applications or creating the data versus using the data.

And because the Internet extends the consumer level, information becomes really important as well. Users aren't processing transactions at home; they're going there for information or for content, ranging from education to entertainment. That's a big theme.

Some other big themes include just getting an enterprise that works. Connecting all the dots from all the different constituencies that sit in front of a computer and touch the keyboard. The number of digital eyeballs is extraordinary.


So for my mom, that concept of the return key was scary. What does return mean? Return to what?

Routes of commerce are changing. Those old routes will look sort of like Marco Polo's routes.

It's happening very fast. The routes of commerce and the toll gates of commerce are ending up in the hands of the software industry, not in the old analog bricks and mortar businesses. Many businesses that have been very stable and around for years and years are going to change dramatically.


Marco Polo

Five years from now when we look up, we most likely will not be buying airline tickets through a travel agent. You will probably belong to all sorts of buying clubs that are digital. You'll have your own cybercash account somewhere; you won't drive to the bank anymore; digital signatures will be real. Right now, it's amazing how quickly some digital commerce companies have grown to 20-30-40 million dollars in revenues when they didn't exist a year ago.