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Ann Winblad: Software Entrepreneur, Venture Capitalist, Ex-Cheerleader

Ann Winblad (b. 1950) sold her first company, Open Systems, a pioneering accounting software manufacturer,for $15 million, and co-founded Hummer Winblad Venture Partners. She's a Silicon Valley power broker and a digital culture celebrity who has started and directed dozens of software and Internet companies. In this interview, she tells a lot about how she got her start...and a little about her former boyfriend, Bill Gates.

By Michael Gross
Interviewed in San Francisco and New York in fall, 1998

MG: Where do you come from?
AW: My mother comes from a family of ten. My dad comes from a family of six. My mom’s parents were from Prussia–Germany. My mother used to have to pay me a quarter to sit on my grandfather’s lap because he was so scary. My dad’s parents were born in the original Swedish settlement in Minnesota. I was born in Red Wing, about sixty miles from Minneapolis. It is the home of Red Wing pottery and Red Wing word shoes. My parents grew up in Red Wing and my grandparents and my older aunts and uncles worked in the potteries and the leather factories.
My father’s family was extremely poor. He really never got anything at Christmas, sometimes an orange. My mother went to nursing school. My father went to college one year, joined the marines and went to World War II, on the Pacific front, returned, finished college in three years and had nine athletic letters. My mother wanted to have ten children. She had six and I’m the oldest but my youngest sister is only 8 years younger than me. My nickname when I was born was Tecky, a Swedish nickname–not Techie but Tecky. Until I was in first grade, my name was Tecky Winblad. In fact I cried when my parents told me my name was Ann because it had only two unique letters in it. When I was growing up the largest amount of money my father ever made in one year was $18,000. I make more than $18,000 a day some years. Its really nice to know that I can provide for my family.
MG: Bob Dylan sang a song about Red Wing reformatory, didn’t he?
AW: Whenever we were misbehaving my father would drive us past the Red Wing reformatory and say that’s where would go.
MG: here did you grow up?
AW: A small town in Minnesota, Farmington. I might as well have been Rebecca of Sunnybrook Farm. Except we did not live on a farm. My father said, join 4-H. That lasted about a year. I can still say the 4-H pledge under pressure.
I don’t remember knowing any rich people. I don’t remember any real poor people. Farmers to teachers. Maybe a doctor or a dentist thrown in there. Everyone was making ends meet. The jewelry store owner actually did have more money. But other than that everybody was pretty much the same.
MG: What was your family like?
AW: We’re a very competitive bunch. My parents are extraordinary dancers. My dad’s real name is Wilbur Winblad but his nickname is Soup, because he had blond hair, cut like a soup bowl. So he’s known in Minnesota as Coach Soup. We used to have little tee-shirts that said little coach. Minnesota in the summer is sultry and warm. We’d have little seersucker pajamas on and we’d be out in the yard. My father was supposed to entertain us, the three oldest girls and my brother who is in the middle. We had little stop watches, my father had a little start gun, and we’d run not against each other because we were different ages and different sizes, but we’d try to beat our own time. So I was really good in elementary track.
It was really quite amazing how my parents made ends meet with six children, they had to scrimp and save. My mom would buy cheap dolls for Christmas and she’d sew the clothes so we’d have a box full of dolls clothes. Today, my mom is 72. My dad is 75. And they deserve to live to be 120. They loved the idea that they had all these little girls. We didn’t have a sense we were trying to survive. But we never had Coca-Colas in the refrigerator. We always had Kool-aid. We never went out to dinner. We never went out on vacation. I sewed my own clothes. I’ve had a job since I was six. We couldn’t go to movies unless we could get the money ourselves because we didn’t have extra money for that. So I had an art show. I made all of my sisters and brothers draw pictures and I put them all up in our big basement and then charged all the rest of the kids money to see them. I charged people two cents. It was fifty cents to see a movie and the art show bought me a movie ticket.
MG: Have a TV?
AW: We had a TV by 1955, but there was nothing on. We would watch Bess Meyerson and The Big Payoff where she’d run around in a mink coat. That’s all I can remember. That mink coat and Our Miss Brooks. We had a lot of stuff going on in our house, we liked each other a lot. We made paper dolls and we had contests and we had theater. We lived in a town for a while and then moved out in the country. So we could ride our bikes for miles. We could hike into farm lands. We had our own adventures. I would say what time do I have to be home by and my father and my mother would say, “Ann use your own judgment.” No one ever bounded us. They came from loving families. They wanted to have one of their own. They wanted to live their life for their children. There were parents who felt like their job was to have a family and take good care of them.
MG: Were your parents political?
AW: My mom was just like every woman of voting age in that country, a total supporter of Jack Kennedy. But my parents really were not that political. We didn’t have dinner and talk about campaign issues. You have to remember my dad is a school teacher, my mom has got six children. When I’m in college I still have a 12 year old, a 13 year old, a 14 year old, a 15 year old, sibling. So there were a lot of and life was focused on us. It wasn’t focused on who was going to win the election.
MG: How did you do in school?
AW: I was a smart girl and a popular enough girl. So high school was a blast. plus I never had to study. that drove my sister nuts.
MG: Were you one of the smart kids?
AW: People ask me that all the time. They say were you a nerd in high school. And I go no, I went to the prom. I got to be a big fish in a small pond. I’m a cheerleader, I’m a valedictorian, I’m dating the captain of the football team.
MG: When did outside culture enter your life.
AW: Minnesota is a great state. There is a lot of wealth there and a lot of sophistication. We had great art museums, a symphony, dance, and we weren’t far from the nig city of Minneapolis. Bob Dylan hung around the University of Minnesota. I loved music like everybody else. We had a speedway they would bring in all the top bands. Fellow girlfriends, cheerleaders and I used to go up there, put Grenadine in our sleeping bags because we thought that was alcohol. We didn’t know grenadine and scotch were two different things.

MG: You graduated in ’69. Did drugs, sex and protest come into your world?
AW: Drugs, a little bit. Sex in high school was really a bad news thing, because it was such a small town and also so Catholic. By the time I was a junior, kids had figured there was marijuana. We had parties where people would smoke dope. Not a lot. I don’t remember where it came from. One time, I came home without my shoes and only my sister noticed I didn’t have my shoes, and I had to have someone bring them over the next day. That was pretty late in the game. But it was enough so that by the time you got to college and drugs were everywhere, you didn’t think, “Oh my god, drugs!”
It really was sort of like being in Shangri-La in some respects because people were very happy. For some reason it was invisible to us that people’s siblings were being drafted. In my senior year people started talking about graduating and being drafted. Only then. You didn’t have things like teen suicide. Very few teen pregnancies. The town was totally unaware of that there was even marijuana being smoked in houses or what it smelled like or whatever. People trusted everyone. You didn’t lock your doors.
Then I got to college. You are not in your own parish, so sex is fine. But I think the thing about college that was interesting was thinking that you were going to join this challenging world but it wasn’t that challenging. There were girls from richer families which was a difference.
I got a scholarship and went to the College of St. Catherine and the University St. Thomas in St. Paul, Minnesota. It was endowed by Control Data and got millions of dollars for computers so we were forced to take computer classes everywhere we turned. It was cool. It was like sewing; you can put something together. And I was an experimental student. Twenty-five students could do anything they wanted. They didn’t have to take any prerequisites. So I finished my math major and took a business major as well. I was terrified of taking a business major because I thought businesses were only inherited. This is another myth in small towns, that you can’t get into business unless you are already in it. Well imagine my surprise. I don’t have to be a math professor, I can do a business thing!
I got a job as a cocktail waitress since I could earn the most money there. I convinced some night club to hire a college student. And they didn’t hire college students. I’m showing up at work at 10 and working till three serving drinks. The girl who sold the most drinks got an extra hundred dollars. We were only paid minimum wage. I learned how to fall on top of drunk guys who would not only leave the bar but pay me big tips because they tripped me. I was very good at this cocktail waitress thing.
MG: Were you all business?
AW: College is wild. We wore hot pants. I’d slit the sides of cutoff jeans and I had like rhinestones on them. Leather boots. Halter tops. We virtually wore nothing. We had bell bottoms that hung below this. We didn’t wear underwear. I saved some of the clothing I wore. It looks like doll clothes. We’d take our clothes off in an instant and we all smoked dope. Everybody was very happy, hanging out with everybody else. I dated a guy I met who was a bartender who was also a school teacher. He was 35 and I’m 19. It was loose. You didn’t worry about dating a different guy the next week. I knew how to get birth control from Planned Parenthood. But I had friends that refused to use birth control. There were a lot of college abortions.
I went out with a guy in college early on in college that went on a really bad trip and scared the hell out of me. It was like what do I do now. The trip lasted a long time so it really scared me. I didn’t use LSD and I didn’t use coke. Although all I would have to do is hold out my hand. I went to parties where there’s marijuana, LSD, coke just in the kitchen. It was just like potato chips. And I was really shocked when I moved, when I started coming to California in the late 70s after I started my company. People were doing lines of coke and I thought, didn’t they already do that? It was really amazing how it seemed to me that they were behind. It was like we all outgrew that in Minnesota: We did that in college.
I had summer jobs, plus my cocktail waitress job. I actually earned quite a bit of money in college. Enough to go wherever I wanted in college and have a car, pay for my insurance, I still didn’t fly anywhere. Friends of mine once went on a trip to Padre Island off the coast of Texas. We drove. My father wouldn’t let me drive my Ford Mustang so he made me take the family station wagon and trade with him.
I went off campus to expand my experience. That was really interesting.. And I also joined an antiwar theater group. My dad the marine says, ‘Look, we’re only subsidizing you a little bit ’cause you’re on scholarship and you’re earning the rest yourself, but, if I ever see you at one of those antiwar things, you’ll never get a dollar from us.’ Of course I knew he never meant it. Two of the guys in the troop were part of the group that bombed Honeywell. We were practicing one night and they were saying ‘We did it, we did it!’ Honeywell had a factory there that made bombs or something and they blew it up. So it was like, ‘Oh, great, now I’m going to be on an FBI list.’
We had all read Zen and the Art of Motorcycle Maintenance. After college my then boyfriend bought a motorcycle and we took a motorcycle through Europe.
MG: Were you aware of feminism?
AW: Ms. magazine we considered a joke I think. It was more a sixties thing. I felt like it already happened. I was probably more like Ally McBeal. I went to work. The year I graduated was the big year of affirmative action. That I remember big time. At our campus people came and said, Hi Ann you’d be a perfect plant manager for 3M. And I’d go hello. Who works in those plants? Big guys. The FBI or the Social Security administration calls and they say we’d like you to be an agent for us. And I say, do I have to carry a gun? How much is this going to weigh? And they said 45 pounds. I’ll tip over! I can’t take that job.
MG: Meanwhile, you were learning to program, to write code. What language? Fortran?
AW: Fortran. Exactly, Assembler. But I would also take a month with the Minnesota dance theater. I took acting. I think I was unusual in that respect. I think one of the things about a lot of the women in [the computer] industry is that they’re not happy with the girl side. They found a safe undercover role. The didn’t find a, I’m going to have fun side. I’m a real girl. Lets just go out here and party. Plus I didn’t need to study and that also helped a lot. The fact that I trusted that I would just figure stuff out.
We had mainframes and some DEC minicomputers. The first computer class I took was an interim class where you took something for a month. And that was a Fortran thing taught by a sister. The next time they had that interim she was sick and nobody else could teach it, so they offered me extra credit to teach it. I pity the poor students. But the program seemed like a tool. I had a tool. But yet I didn’t want to be just a programmer. So I took this job at the Federal Reserve Bank. ‘Oh gee, I can work in the research department of a big bank.’
MG: Did you program at that bank job?
AW: I did. I spent the first couple months learning how the programming worked by fixing people’s code. My cubicle mate became one of the cofounders of my software company. He would leave every day between three and four o’clock. It took me a while to ask him why. He said ‘I ride my bike home. I watch I Dream of Genie.’
I was hired for that job because of affirmative action. They were supposed to hire college degreed women. I got my masters degree at night. The Fed had an educational policy there that it would pay for your degree. I was called in and they said they decided not to pay for my masters degree because I would be the highest educated woman in the bank. If I’d been more confident I would have said fuck you. And I did write a fuck you letter to my boss when I left. He died of a heart attack a week later. I felt bad about it. Nothing to do with me but he must have gotten more of those.
The first plane ride I took out of Minnesota, I went to Puerto Rico. Then my next flight was probably out California to do a business deal with a computer company.
MG: You and your future partners quit?
AW: We quit in 1975. I quit for two reasons. One is because of this student thing. And I quit because I thought, I could be like the people in this bank, they sit in these cubicles, they don’t have any passion for what they’re doing. They leave at 5pm.
I went out and got us a consulting agreement. We were going to divide our time, write a student accounting system for vocational schools during the day while we decided what are we going to build the company around. I just thought, we’ll figure out in the first year what we’re going to do.
MG: You, Bill Gates, Paul Allen, you were all starting out then. Did you think about getting rich?
AW: I knew them soon after. I met Paul Allen before I met Bill. No one was in it to get rich. Everyone had wandered off the path. Bill wandered off the school path. They just said something is wrong with this path. I’d gone through school not on a normal path. I’m on some yellow brick road. I don’t know I’m on it. People are writing Surrender Dorothy in the sky. I’m ignoring that. I don’t realize I’m doing something so different. I’ve had no money.
Paul Allen had a real vision. “We’ve got to do this. This is happening, Bill. Let me show you the cover of these magazines.” And he dragged Bill out of college to do this. Not kicking and screaming but he went and pounded on the door. But there weren’t many Paul Allens around. Gordan Eubanks started an early software company. He was in a submarine programming for the Navy. What was he going to do? Come above ground and program again. These nerd stories are repeated over and over again. They were honed programming machines. That was all they could do. And they got lucky because they–
MG: –were there with the right skills at the right moment.
AW: –and they decided they were independent thinkers, so that they would try their own thing and their own thing led to these small computers.
MG: You didn’t see the future?
AW: No. There was no future to see. It was very blurry then. We decided we were only going to program on computers that were bigger than the ones that required soldering irons, and smaller than the ones that required an air conditioned room. So that included what were then called personal computers and up to small or mini computers. And we ended up doing personal computers.
Bill started with kits. We wouldn’t do kits. There were computers out there that were creeping in from the mini computer lines. We wrote our accounting system for all of them. You hung floppy drives off the thing and our whole system took 9 floppy drives. It would say ‘Insert disk twelve into slot five.’ You had to be like DJ to run this stuff.

MG: What star were you chasing?
AW: I have never put myself in the visionary category, out to change the world. But I’m willing to go to the edge of risk. You are always seeking the edge. If you searched for the edge, then you ended up in computers because it was the edge.
MG: Did you see a business opportunity.
AW: No. I really think that I just said, I want to get out if here. They really don’t want me. They want someone else. They don’t even want me to be educated here. I don’t really want to be running out of some place at 5 o’clock. I didn’t have any big responsibilities. I didn’t have any money. I had debts–loans from college. I had a car. The Mustang died, so I had to buy a real car that cost real money. So I had a car loan.
I couldn’t buy a mainframe or lease these things. That was way out of my economic league. So timing led us to smaller computers. We needed more money than we could create in profits to get these computers for our programmers to use. We worked at the local [computer] dealership, but they turned off the air conditioning at night when our programmers were there so they started just programming naked. The secretary came in one night and didn’t. Didn’t understand naked programming. I was not one of the naked programmers. But we couldn’t program there anymore. So I went to every bank in Minneapolis and there were a lot of banks. I had a great business plan; we were starting to have revenue and I could explain what we were doing. I could explain all the passion. Now by this time we understood the small computer thing was happening in spades and we were in it although spades still seemed pretty small to people. I got the decision maker in front of me. Made sure I got in a closed door room with him and explained the thing to him. As soon as could see the word no forming on his lips. I just made myself cry. I practiced crying at home. He totally disintegrated just like they said in my industrial psych class. Acting class helped me! He started getting the paper work and signing it. I walked out of the bank going “Yess!” I got the 25 or 50 thousand dollars we needed for the computers.
MG: You were designing software-but for who?
AW: The hardware companies. They had to work with people like us because they were bundling software in the machines. And that’s where Bill was selling his. We were all selling OEM deals. Original equipment manufacturers. Buy a computer with something inside.
MG: Did the company have a name yet?
AW: Yes. We named it Open Systems. Which was really interesting, because we trademarked that name, and it’s sort of now part of the nomenclature. We didn’t make it that. We just sort of commercialized it. When we first rented an office, Prince had his recording studio below me and I used to go down there and scream at him. It was the artist not yet known as Prince.
We had read this book on systems. It was called “Rhythms of Vision.” There was a weird sort of nerdy guy that wrote it (I can’t remember the author), and he was talking about open architecture for systems, and then Eastern stuff, the perfection of things. So he was one of the co-founding guys who was way deep into this stuff. The Open Systems thing and our logo all come out of that one book.
MG: You take your leap of faith right in the face of what’s about to become one of the worst economies in the last 100 years.
AW: Well, it was a good time to be an entrepreneur then, because no one else had money either. We did a lot of things. We started the company from my apartment. I figured out how to qualify for Food Stamps. Just all part of the great adventure.
MG: This is also the moment of the so-called “human potential movement”…
AW: The one guy that I started the company with was my boyfriend also. So we were living together off-and-on, mostly living together during that time, and he was deep-space into this stuff. So I go to these Yoga classes. Then I discover over time that this Yoga teacher is hand-picking the cutest girls from the Yoga class, and he’s sort of like “Now we’ll all relax,” and sleeping with them. But this just doesn’t seem to occur to anybody there.
We all got mantras, had our mantra initiation, and all that stuff. We had swamis. Swami so-and-so stayed at my house. I got really tired of the smell of incense.
MG: So what did Open Systems do?
AW: Well, we decide that computers are really getting smaller, and that we should try moving down to these smaller computers. Basically, that’s what we did. And we thought, “What can we write?” We talked to a few dealers of these computer systems, and they said, “Well, we’re mostly going to sell these to businesses, so we’re going to need accounting systems.” So we took out my college textbook, and designed an accounting system. Fortunately for us, Tim had actually designed systems before, so he could serve as a real architect here. Me, I wasn’t really afraid asking people dumb questions, like, “Well, what would you want in your accounting system?” so we could narrow it down to a smaller amount of work. So we did that, and we moved from computer to computer, and we got really good at porting to all these twist-and-shout versions of different operating systems. It worked on everything.
We lost $85 our first year. Everybody got panicked because we lost money. We believed we had to be profitable.
MG: Give me a sense of the broader world. The first accounting package was Visi-Calc, right?
AW: We’re before spreadsheets. Way before spreadsheets.
MG: So you’re not doing a commercial packaged product.
AW: Yes, we are. There were no retail stores to sell to. But we had the same product, we wrote a set of manuals. We then sold this to dealers who resold them. We didn’t do systems modifications. We sold a standard cookie-cutter product. In hindsight, I wonder how we figured this all out. I just don’t know. We had no business-experienced parents to ask questions of. We had no peers who knew anything. We had a Minneapolis lawyer who was great, but he didn’t know anything about technology.
MG: Is it just this one product for a period of time?
AW: Basically, the product evolves. MS-DOS came out.
MG: Enter Bill Gates.
AW: Microsoft isn’t very visible. We skipped CPM, which was a cul-de-sac for a lot of people. We were doing lots of bundling agreements where we’d sell the rights to include our code with machines. And we were getting better at that, so we were selling those for bigger dollars.
MG: Your customers were what? Small to middle sized businesses? AW: Right.
MG: But also with the bundling agreements, your customers are the hardware manufacturers.
AW: You got it.
MG: But these are not the people who are inventing the future. And somewhere right around here, you’re going to encounter those people, aren’t you?
AW: Well, interestingly enough, I know a lot of them all the way along. I’m on the West Coast a lot of times. I’m at these industry confabs. We’re the only people in the business. We all met each other at conferences. We were just all there together, saying, “What can we make of this? What does this all work on?”
MG: Was it competitive, or was it cooperative, or some combination of the two?
AW: We didn’t have much to offer each other. The hardware manufacturers were the center of the universe. Until well into the ’80s, retail distribution was… I’d gone into Computerland Corporate and that whole est crew… I remember when I went out there to negotiate a deal…
MG: Computerland was an est·?
AW: Totally. I went out to negotiate a distribution deal with Computerland, to get our products in all their stores. There was a guy (and I can’t remember his name), he had a naked picture of his wife facing outward on his desk. It was just an est thing. You just got used to personal uniqueness.
I went to negotiate with TRW on the Fujitsu deal, and I’m sitting there, you know, and the big-time TRW lawyer dramatically gets up from his desk, stands in front of the door and goes, “I’ve locked you in here.” Oh, great. And I have no response to this whatsoever. You know that he wants me to have some sort of, like, “Oh, what are we going to do.” I say, “Okay, well, let’s hurry up and finish the contract until we unlock the door.” He goes, “Well, you’re not getting out of here until we finish this contract.” I go, “Okay, good. Fine.” He was so disappointed.
I would go visit all of these dealers to make sure they were still selling our software — around the country. I remember visiting one of the dealers in New Jersey, an older guy. All these guys were “los conquistadores.” They sold Singer hardware before. Have you ever heard of the Singer computer? Like the sewing machine guys. They had this thing called a Flexo-Writer, you dropped this big magnetic card in there, and it goes Ka-CHONK Ka-CHONK — a laser thing which prints invoices. So they were all sort of bonded. And at the annual meetings they used to bring in strippers to entertain these guys. I would be telling them about our software, and I’d be followed by Suzie the Stripper. It was really a generation thing.
I remember visiting this big dealer in New Jersey and we had to drive from Newark to Cape May. And this guy, who was married and had two children, had a Miss America along as his date. So I was in a car with the former Miss America for however many hours it takes to go through all those tollbooths. I was all part of the big adventure, and everybody was doing the same thing.
MG: You cash out big-time at some point. Right?
AW: Yes, we sold the comnpany for cash. I get all this money at either the end of ’83 or the beginning of ’84. Because I remember by the time I got to Esther Dyson’s conference in February, I already had all the cash. Then I moved to California at the end of that year.
MG: But two to three years before that the personal computers start to happen.
AW: Oh, yeah. And real money starts happening.
MG: Does the arrival of the personal computer change your business at all?
AW: Oh yeah. There are places like Computerland, and they are signing separate orders for software independent of the hardware-maker. So now we have a common operating system for the first time, which is DOS. We sort of had caught wind that IBM was going to release [a personal computer], that they were going to bundle some software on it. It turned out that they actually bundled a lower-end accounting product.

MG: What about Apple?
AW: The Mac was too small to support an accounting system. So we didn’t ever have our stuff on the Apple. And Apple was only Apple. They didn’t clone like IBM did. That changed everything. This was really just breakthrough. IBM gave out all the tools you needed really early to all the developers to get over to this operating system. They really made things happen quickly. Remember, at the time there’s not a million users of anything. There’s 50,000 here and 200,000 here. That’s when retail distribution happened, and we all had to buy shrink-wrap machines and design boxes. Now we’re going to talk to the masses, and how do we do that? We have to go and negotiate with retail folks who are going to send the stuff back if it doesn’t sell through. Basically, they’re taking it all on consignment. So we’re trying to negotiate deals where they pre-pay for this stuff, and they absorb some of the risk, and they’re saying we’re small and whatever. It’s a whole new learning curve. We all are clawing away at est guys in Computerland, and then comes Businessland and then comes, Tandy. We buy shrink-wrap machines. We have a warehouse. We buy forklifts. Because we are sending out thousands of boxes to hundreds of retail locations. We have assembly lines, we have somebody that’s head of manufacturing.
MG: So you go from an $85 loss in ’76–
AW: –to about a $15 million run-rate. Which is huge for a little nothing software company at that time. Then things accelerate. Our OEM’s now are not hardware companies alone.
MG: OEMs are bundles.
AW: Bundles. Somebody else resells it. They put their name on it, or they re-brand it. But every time we have one of these deals, they all want to buy us. So now we’re saying, “Hey, this might be worth something” and we went–as individuals–to an industrial psychologist who evaluated our goals, our stress portfolio.
MG: This is like couples therapy for business partners?
AW: Yes. Exactly! They gave us adult IQ tests. The guy says, “Look, as you’re growing really rapidly here, either you all agree to sell the company, or you decide who wants to stay the course and you sell that person your shares.” Which would have been impossible. How do you value private shares? Acquisition offers were right in front of us. We could see real money now. “I’ll pay $10 million, $12 million, $15 million.”
MG: Had your lifestyle changed yet? Had you had enough time to have a lifestyle?
AW: We were very profitable. We all had to pay our student loans, so we paid ourselves a couple of hundred thousand dollars a year. In fact, when Bill Gates met me he said, “I saw your salary; you get twice as much as I do.” I go, “Well, maybe I’m more profitable than you.” I remember telling him that. Which was, of course, untrue. But I owned a house. I drove a VW-Rabbit Convertible. I could go on vacations wherever I wanted to. I could afford to buy the clothes I wanted. But I had to still have a budget for myself. That was quite a lot of money. There was more opportunity ahead, and I really didn’t have to fear the future. So we decided this company, UCELL, was our likely acquirer in Dallas. They offered $15 million cash. I had no debt. I could use this money for anything. I paid off my car loan and I bought some things for my family. But it was a huge amount of money. Two of my co-founderd retired. I could have said, “Okay, great, gee, I’ll open a dress store here in Farmington, Minnesota, and live happily ever after and grow tulips.”
MG: But?
AW: When I sold the company I was turning 32. Bill Gates was 28. So we’re still not very old, and we’re making things up as go along. So UCELL is a public company, I could sit on the Management Committee of a $200 million revenue company — it was a huge software company at the time. I agreed on a handshake to stay until I helped them find a new CEO.
MG: For your division of their much larger company.
AW: Exactly. So it turned out to be a great year, because they basically let me do my own thing. I had to extract myself from the company because I wasn’t going to run it — which is a hard thing. Psychologically it was a big adjustment for me to sell the company. I learned a lot about management. I did all the worldwide analyst tours. In fact, the head of Investor Relations at AOL now was the head of Investor Relations then at UCELL. So we toured the world telling the UCELL story. And guess what happens to the stock. It goes from $9 to $27! [laughs]
In the meantime, I had discovered, “Hey, winter is optional.” I could finally afford the option, so I moved to California in late November of ’84. The moving truck got lost with everything in it, so I lived in the Four Seasons Hotel for a month while they tried to locate all my belongings. Which was sort of fun.
MG: Were you there with a plan?
AW: I didn’t know what I was going to do next. But I had enough time that I could look around. It was an interesting time, because by this time we’re well into this PC thing, and a lot of land has been grabbed. In fact, it was a bad time for venture capitalists. VCs lost a lot of money. Because there wasn’t another Lotus ever, and there wasn’t another Microsoft ever.
MG: The tent poles were in place.
AW: So it turns out that it was a great thing for me. I think I said, “Why would I now, just having finished six years of doing the company thing, start up again immediately and get back on the treadmill? I can really try to get a bigger picture on things.” So I spent two years consulting, and reading. I helped Price-Waterhouse rewrite their whole framework for annual technology planning. I helped Microsoft work on their yearly strategy,. I helped a lot of little companies in venture capital. And then I met John Hummer in ’86…
MG: He was a professional basketball player, right?
AW: He finished playing in 1976. He got his MBA in the class of 1980 at Stanford. He was already a venture capitalist. He had been for six years.
MG: And along comes the Internet?
AW: The Internet wasn’t until ’95. There was distributive computing in the interim. That happens about 1989, when we started [Hummer-Winblad, their venture capital firm]–serendipitously. My first couple of deals were PC deals where we made money on them, but they were fringe things, like electronic clip art.

MG: When did you meet Bill Gates?
AW: Bill and I met in 1984 at Esther Dyson’s conference. I was in a really great state of mind. I had all this money, and I feel very comfortable about having chosen as my destiny to be in this Nerdland, and I’m not worried about what happens next. I’m learning a lot from this new CEO in UCELL, and this guy is really incredible, so that turns out to be some gift that was given to me accidentally along with the money. And Bill was just very interested in me. So we started seeing each other. I’ll skip the details in between there. We really have a lot of commonalities and a lot of differences. I was still living in Minneapolis and Bill was in Seattle. And we went out for four years. Microsoft goes public in ’85. Microsoft just had less than $100 million in sales when it went public.
MG: Were you involved? How to put this? You were a girlfriend, but also a very accomplished business-person.
AW: We talked about a lot of stuff. We talked a lot about the future, both of ourselves and of the industry. And Bill certainly shared a lot with me about his psyche. Bill is always thinking all the time. He’s very smart and he’s very confident. But he wouldn’t call me up and say, “Gee, I’ve got a big strategic problem; help me out here.” There was nothing unknown to me about Microsoft at that time, nothing unknown to him about that business that I was involved in, and there was a lot of confidence that we wouldn’t talk to anybody else about this, that and the other. That’s how the relationship worked.
MG: What’s the age difference?
AW: Bill is five years younger than me; he’s 28, I’m 33. Our birthdays are three days apart. It wasn’t like I had a goal of dating the richest guy in the world, because he wasn’t! I had to come up with the cash for a lot of this stuff.
MG: When you went out for pizza?
AW: He always carried a hundred-dollar-bill in his wallet, and he was very proud of that.
MG: Did he not want to break it?
AW: No, he did. But I would pay a lot of the times, too. It wasn’t like, “Oh, Bill, you’re the rich guy.” We knew each other as people. And we grew up a lot, a lot was happening to both of us. And we trusted each other about a lot of our thoughts and about a lot of things. So we developed a friendship that I think will last forever.
MG: So I assume you were a PC person, not a Mac person.
AW: I started using a Mac. I ditched my PC.
MG: The cliche is that the Apple guys were the counter-cultural dreamers and that Bill was the technocrat. Was it that simple?
AW: No. Bill was a really common-sense guy. I mean, he has done all the normal stuff, but he never did anything way off the track. He didn’t do Yoga class. And Steve Jobs has enough of that in him that it is woven in his mystique. I watched him for a year. He used to drink so much carrot juice, he would be orange.
I remember sitting in an audience once with Bill where Steve was speaking, and he’s theater. He loves the limelight. He likes speaking. He wasn’t nervous. And Bill said, “Some day I’ll be able to be as good a public speaker as he is. How do I do that? I’m going to work on that.” Steve was the first guy, in my mind, who actually knew what to do with the spotlight. And also, he was the only guy who did brands. He built a brand. Who else was building brands? Microsoft wasn’t. What’s Microsoft? Nothing to anybody. It’s like plumbing. So Steve was and is unusual in many respects. He’s the first great salesman, the first great public speaker, the first Cute Guy in our industry.
MG: The Rock Star of Computing?
AW: The first spin-meister. I mean, he never worked as well as his hype–in the beginning. He had this dorky computer called the Lisa which was a complete bomb. He was absolutely an abysmal manager. He’s terrorized people at Apple, an out-for-their-head type thing. Drinking carrot juice and turning orange. But he’s sexy. He had image. And we all just fell in love with the Mac. We all bought Macs. Bill bought a Mac. Bill was using a Macintosh. Not a PC, a Macintosh! I mean, we all used Macs! I think in many ways we all wanted to be Steve, just like Bill’s thing, “I wish I could talk like Steve.” It was sort of like we had envisioned ourselves in the spotlight–except we really weren’t. We were just like nerding along, getting bigger, and Microsoft was getting bigger than it ever thought it would, but Steve put us center-stage. And we’re all back on PCs now.
MG: When did Microsoft start to be portrayed as the dark side of the force?
AW: Well, I think you’ve got to be careful with this “dark side of the force.” Microsoft was growing by leaps and bounds. And I think what happened was that all of a sudden there was a winner. But it’s really challenging to be a winner in a marketplace where new entrants are coming in all the time. Because there are no gatekeepers closing anyone out. Like AOL. AOL has always been pioneering, on the curve, but no one gives them any credit. They’re like Rodney Dangerfield. How many times has Microsoft tried the equivalent of AOL and failed? Does AOL get any credit for that? No.
MG: Everybody hates a success?
AW: Exactly. And the success was already happening in the ’80s. Then, when we get into the late ’80s and early ’90s, it’s a whole different ballgame. Like, Apple forgot about servers. They should have cloned the operating system. They used the winning formula over and over again versus thinking of a new one. And Microsoft rethought their way through five computing generations–the mainframe, minicomputers, PCs, distributive computing, Internet. And all along the way, people get left behind — or decide to stay behind. Some people say, “This is it for me, I’ve done my bit in this, I’ve made my dough, I’m out of here.”
MG: You and Bill as a couple ends when?
AW: ’87. It’s interesting how we decided to sort of end this thing. In ’87, remember, I’m 37 and Bill is 32. At this point in time, I’ve got John Hummer breathing down my neck, and it’s like a lot of decisions had to be made. We were starting to write this plan then. We wrote the whole plan in ’87. We raised the money in ’88. So [Bill and I] decide to “just be friends,” just do our own thing. We’d spent every moment of our free time with each other in ’87, and Bill’s family was very unhappy about that. So then we make this pact…
MG: The famous pact!
AW: Yes. We always go on a trip with each other once a year.
MG: And do you still do it?
AW: Every year.
MG: Okay. So Hummer-Winblad opens its doors?
AW: It takes 110 meetings to make our first $35 million in over a year. People think the software market is in the toilet, return is at an all-time low, there is effectively a recession in technology.
MG: This is right after the October ’87 market crash?
AW: Yes. But John and I say we’re not going to give up. We’ve spent 14 months raising the money, five months getting all the documents together, getting all the lawyers. It is torture! It is hard! But of course, during the same time, it’s really great, because during that time you really learn how well you’re going to work in partnership with the other individual. And boy oh boy, did we learn a lot about each other. And we felt so much respect for each other during that year-and-a-half, it was just amazing. So there is nothing that can break our partnership. We do our first deal in the Fall of ’89.

MG:     So you’ve raised your…

AW:  $35 million.

MG:     You’ve raised your nut and now you’re going to start doing business.

AW:  Right.  And that’s what happened..

MG:     Do you have a set speech?

AW:  I have a rolling speech that I change all the time.  I upgrade it… In fact, that’s one thing I learned from Steve Jobs, is that he did not, you know, write a new speech all the time.  He had the same speech and he got really good at it, and he said what he really knew. 

MG:     All those hippies in the ’60s who thought they were going to change the world… You guys, the practical ones, you went and changed the world.  And what you did was, you gave… and I’ll say “us” here, because I’m not entirely impractical, but I was pretty impractical.  You gave us exactly what we thought would happen.  But it took the practical ones to go do it.  And yet, there was also this element of dreaminess in it, too…

AW:  Well, I don’t really get where the dreaminess comes from.  But there has to be some there.

MG:     You made a leap of faith.  Come on, you opened a business and you didn’t know what you were going to do!

AW:  [LAUGHS] I didn’t know anything.

MG:     Tell me that that’s not dreaming.

AW:  Yeah, it is dreaming.  And our dreams were based on reading books.  Their dreams are based on surfing the Net.  The images that they’re seeing, they’re not reading about Sarah Bernhardt, you know, or…

MG:     See, but I think that there’s a great, great potential for disaster in this…

AW:  Yeah, I do, too.

MG:     …because what is going to be forgotten is history.  History is going to disappear.  And they have no sense of history, they don’t care about history…

AW:  Real time.  It is all in real time.  Life is now… Nothing is linear.  Everything is a hyper-link to them.  And they’re not… They’re going to be raised not to think linear.  And it’s not that one is better.  They’re different.  I mean, creativity is not the same as imagination.  And also, the idea that everything is available to you on command… They are.  Snap your fingers, and it’s there.  It’s not like, “Well, but you might have to do something, wiggle a little courage,” not courage like Danger, but courage like “You don’t know.”  They want complete information before they go to Step 2.  Well, come on.  Go there.  Just try it out.