Developer, venture capitalist and businesswoman. Ann Winblad has been at the helm of myriad companies and startups and, with her nearly 40 years of experience in the tech industry, it could be argued that she practically built Silicon Valley. She is a living legend in the startup ecosystem and has a nose for innovation unlike any other: she was the first, in the 70s, to see that software was the future, which is why she decided to invest in Microsoft. She became not just investor but girlfriend to Bill Gates, with whom she stayed friends after their relationship ended. That friendship that will last a lifetime. There is an exceedingly strong bond between the two entrepreneurs and, in the 90s, Newsweek published the news that Microsoft’s top dog had even made his wife, Melinda, sign a prenup that guaranteed he could spend one weekend a year with his ex.
Winblad is visionary, eclectic and very, very determined. She has shattered the glass ceiling in one of the sectors with the smallest female contingents. She says things have really changed in recent years and that it was very hard at the beginning. It took a strong moral compass and a strong sense of business.
One of her most famous anecdotes is from the 80s at a venture capitalist event. As was often the case, Winblad was one of the few women present. The organisers decided to assign her a shared room with the other woman invited to the event, one of the performing “artists”: this artist turned out to be a stripper. “Let's put it this way, she wasn’t in the room much," said Winblad. "That kind of stuff hopefully does not happen any more.”
Data is the new oil.
And there are those who describe her as “the first female programmer”, to which she modestly replies that there were others before her, giving the example of Ada Lovelace, an English mathematician involved in the creation of Babbage’s analytical engine in the first half of the nineteenth century. “I’m still alive, though,” she points out, jokingly.
Winblad was born in quiet Minnesota. Her mother was a housewife and her father a high-school basketball coach. “[Coaching] is a great thing to do but you don’t make a lot of money and I’m the oldest of six kids.” It was within the walls of her low-income childhood home that this young girl learned to go it alone and showed early signs of a talent for numbers. The path was clear: at university she chose to double major in Mathematics and Economics. Her father played a key role in her career as her profession requires her to channel her passion into nurturing others’ talents: she says her father had been preparing her to become a coach all her life and that, when you make the transition from entrepreneur to venture capitalist, that’s exactly what you become. It’s a transformation: from player to coach.
“My father had been preparing me to become a coach all my life. When you make the transition from entrepreneur to venture capitalist, that’s exactly what you become. It’s a transformation: from player to coach.”
This was clearly her calling: after graduating, Winblad chose to pursue a Masters in International Economics with a focus on Education. This focus would come in very handy in carrying a team of professionals - each equipped with very different skills - to success. Beyond her passion, Winblad thanks her father for something else, too: she says he prepared her for the all-male climate of Silicon Valley as, with her father being the coach, she was “in [the men's] locker room a lot” for the post-match debrief. It helped her grow a thick skin, something Winblad has really needed to get on in an environment like the investment world. One company, Cado Systems, were extremely important for Winblad, as they were a retailer for her software. They were referred to as “Los Conquistadores”. She describes the first time she pitched her project to the retailers and how she struggled to look them in the eye - most of them had 20 years on her. She began the pitch in a very, very polite tone. The Managing Director asked for a break and took her aside. “Ann,” he said. “If you're gonna run with the big dogs, you gotta learn how to lift your leg.” She has never forgotten that phrase.
Years ago, if you joined a software company, it was considered fringe employment. But now, software is changing the infrastructure of commerce.
You can’t predict the future, but you can find it
It is Winblad’s infallible intuition on this point that, more than anything else, has determined her success. At the age of 26, she founded her startup. Open Systems Inc. was a company focused entirely on software development. She says it was a totally new thing and that, at that time, no one believed you could make money just from software. So much was this the case that, in order to sell her programmes, Winblad had to initiate a partnership with a hardware company. Things evolved quickly, though, and six years later the businesswoman sold her company for 15 million dollars - one of the largest sales of the times. At 32, Winblad had 15 million dollars quite literally in her pocket: it was a cash transaction. She tells the story of how everyone had maximum spending limits on their credit cards of 400 dollars a month while she was afforded this great availability of cash. For some years, Winblad worked as a consultant for tech giants, from IBM to Microsoft. Finally, in 1989, she realised what she wanted to do with her money and the wealth of skills and contacts that she had acquired over her career. She partnered up with ex-NBA player, John Hummer, who had graduated from the renowned Stanford Business School. Together, they founded Hummer Winblad, the first investment company dedicated exclusively to the software industry.
“We like real software, web scale infrastructure, cloud,” she says, exploring the details of their choice. And the decision to go for software was a bet that soon paid off. The two partners were pioneers in a field of investment into which many others threw themselves in the years that followed. Winblad says that, “Years ago, if you joined a software company, it was considered fringe employment. But now every major corporation has a software factory at the heart of its competitive advantage. Software is changing the infrastructure of commerce”.
In its first few years, Hummer Winblad venture capital firm launched 16 startups, half of which were later quoted on the stock market. This was a record-breaking for a sector with such a high rate of failure. Yet Winblad does not like to be labelled as “visionary”. It’s a term she says lots of investors like but with which she disagrees, believing that being a dreamer doesn’t lead to success but being able to spot an opportunity does. She prefers “opportunist” to “visionary”. According to Winblad, a successful investor can read the outside world, understand what the market and consumers want and - the biggest challenge - avoid preconceptions. “A colleague of mine wrote a book a couple of years ago called ‘The End of Science’. He wrote it to be controversial and questioning, saying that all the big things had been discovered.” Winblad clearly believes that is not true but that innovation needs to be patient: “Half of the things venture capitalists invest in are too premature; but wait about 10 years and many of them become big companies. So look at what’s being funded today and say, that’s really a stretch but keep your eyes on it.”
Our job isn't to predict the future, but it is to find the future.
Winblad also gave a forecast, some years ago, for the data revolution. In 2012, a journalist asked her what the next big innovation would be and she replied without hesitation: «Data is the new oil». This was well before the Cambridge Analytica scandal, when the unbridled potential of data analysis was still just an idea. Yet Winblad believes we have a long way to go before we fully understand the power of data and the value companies will be able to get from storing it.
“This is just the beginning,” she declares in her characteristically pragmatic style, practically tearing down the visionary aura of such a prediction. After all, Winblad doesn’t believe in predictions: “Our job isn't to predict the future,” she says, “But it is to find the future.”
What makes a successful entrepreneur?
Winblad’s career of helping entrepreneurs launch their own startups means no one knows better than she how to recognise the distinctive traits of a successful founder. There are three vital characteristics. The first is energy - both physical and mental. “If you get lazy, you will likely lose unless you are incredibly lucky,” and, for Winblad, even luck is difficult to come by without working hard. “When we see CEOs failing, they might have great intellectual stamina but they’re not willing to put the work in,” says Winblad. Secondly, is a need to stay positive, to always see the glass as half full because that is what gets you through difficult times. “Women in particular should hold this glass in front of them all the time,” she advises. The last quality Winblad believes a successful entrepreneur absolutely must have is motivation: “A question that successful entrepreneurs often ask themselves is, ‘Why am I doing this?’ and you go, ‘I think in some ways, I can change the world.’” That, she says, is how you keep moving forward. “If you get lost in the small picture, it’s hard to attract employees. In fact, an engineer in Silicon Valley will tell you that they are not motivated by salary, they are motivated by mission.”