A cheerleader and high school valedictorian walk into a bar. It sounds like the start of a joke, but it’s a description of acclaimed venture capitalist Ann Winblad ’75. It’s part of a story she told a crowd at a TED Talk decades ago when TED was just getting started. “The title of my talk was ‘Am I the cheerleader or the cocktail waitress?’” The answer is that she was a little bit of both, and they helped make her who she is.
You may have read about Winblad on the pages of Time, Fortune, The Wall Street Journal and even Vanity Fair and People magazine, as she’s known as one of the most powerful investors in the world. She’s appeared numerous times on CNBC, Fox Business and countless other networks to discuss financial investments. BusinessWeek named her one of the elite 25 power brokers in Silicon Valley and Time Digital listed her as one of technology’s 50 Cyber Elite. In early December 2024, she was inducted into the prestigious Bay Area Business Hall of Fame, which celebrates exceptional business and philanthropic leadership. Past inductees have included Apple founder Steve Jobs, eBay CEO Meg Whitman and acclaimed film director George Lucas.
It’s all quite the accomplishment for the woman who recounts that when she was a teenager, she had dreams of attending college out of state, either on the East Coast or the West Coast, far from her Minnesota home in what was then the small town of Farmington. But this oldest child of Wilbur and Elizabeth had never been on a plane. Winblad’s parents didn’t have the money to spare for plane tickets. In fact, from elementary school through 12th grade, Winblad had never even left the state of Minnesota.
“We sort of pretended we were a middle-income family, but we weren't quite middle income with six kids,” says Winblad, whose mom was a nurse and dad a high school teacher, renowned basketball coach, and subsequently a guidance counselor.
“At that time, growing up in the ’50s and ’60s, education was everything, especially to parents who were the first in their family to go to college,” she said. So, she was definitely going to college, with the help of scholarships, loans and part-time jobs, but she would end up staying in the state.
The decision transformed her life. Today, the former valedictorian is a mega-successful venture capitalist based in San Francisco's Silicon Valley and she travels all over the world, including back to Minnesota, where she sits on the Board of Trustees for her alma mater, the University of St. Thomas.
“Ann has exhibited extraordinary leadership during her tenure as a trustee at the University of St. Thomas,” said Father Dennis Dease, St. Thomas president emeritus who recruited her to the board in 1998. “Her unwavering commitment to the university’s health and well-being has played a pivotal role in the significant progress we’ve achieved in fulfilling our mission over the past several decades. In my view, Ann is nothing short of a board superstar.”
That’s high praise for an alum, but you have to know Winblad. She’s a risk-taker. She’s a world-renowned business leader who doesn’t take no for an answer, and she gets the job done.
Building business with sweat equity
Despite all her acclaim, Winblad remembers where she came from.
While her bachelor’s degree was from nearby St. Catherine, the math major spent most of her class time at St. Thomas, then an all-male college, which was her dad’s alma mater. (He received his master’s in guidance counseling in 1968).
“I only took about four classes at St. Kate’s and took the rest of my classes at St. Thomas,” she said. “I graduated as a math and business major and had the opportunity to take the first computer sciences classes, not yet a major, at St. Thomas.”
In 1975, Winblad was the first woman to receive a master’s degree in international economics and education from St. Thomas. On May 19, 2001, St. Thomas bestowed her with an honorary Doctorate of Laws for having “seized opportunities in the business world and the software industry, boldly taking risk-filled challenges and inspiring others to do the same.” In 2003, she received a distinguished alumna award, acknowledging her vast accomplishments as a business leader in the venture capitalist world, a field mostly dominated by men.
Winblad began her career, however, as a systems analyst and programmer at the Federal Reserve Bank of Minneapolis.
In 1976, she used $500 loaned from her brother to start Open Systems Inc., an accounting software company that she and her co-founders operated out of her apartment. Her co-founders were more experienced fellow colleagues from the Federal Reserve Bank whom she had convinced to leave to start the business with her.
“It was a true sweat equity operation,” she said about the business that eventually outgrew her living room, rising to more than 120 employees. By 1983, they sold the company for more than $15 million.
The following year, she moved to California, where six years later she founded Hummer Winblad Venture Partners, a prominent venture capital firm that invests exclusively in enterprise software companies – the first venture firm to be focused exclusively on software. It was a pioneering idea at the time that led to her being dubbed “the woman who built Silicon Valley.”
Winblad became an innovator, in part, she said, because when she was first starting out, she made a pledge to herself. “Twice a week, I'm going to meet strange people – new people. Then you know the network you're always building.”
Career clarity in a cocktail bar
Network-building and life lessons can happen even where you least expect it.
As a college student, Winblad lived in an apartment adjoining Cecil’s, a delicatessen on Cleveland Avenue and had a job as a cocktail waitress at a bar in St. Paul where she often met interesting people – people who tipped well if you provided good service.
During that time, Winblad remembered, it wasn’t always easy making money and saving money for college. Although she had scholarships, she said it wasn’t enough to make ends meet, so she also worked. She recommends it.
“It is really important to experience work early. It is very challenging to go to school and then start working (for the first time) afterward.”
Winblad took a different job every summer she was in college. She did bookkeeping at Cliff's hardware store on Snelling. She went door to door selling long-distance phone plans to thousands of small businesses. One summer, she worked in a pool table factory back office in Farmington.
She said in addition to what she learned in her college classes, every part-time job taught her something about running a business, including lessons she learned as a waitress at Pudge’s Cocktail Lounge in the Highland Park area of St. Paul.
Winblad said she was one of the few entrepreneurs who had ever seen a customer, taken an order and collected money. She knew how to create new products, deliver products and offer sales incentives.
“Any work experience, whether it’s on campus or off campus, you’re probably doing it because you need to do it for supplemental income, but think of that as part of your learning, too, because it really, really is.”
For this reason, she says for today’s college students “internships are extremely important. They help you determine the type of people, or company or industry you want to work with. Don’t wait till year four to try an internship and something that stretches you a bit because you’re going to need it to figure out what to even take as classes, to really understand how rapidly things are changing, and to know how you pick your tribe – your career.”
It’s similar to advice she gave a St. Thomas volleyball player this semester. “I said to her, ‘Look, you know, some days you’re tired and you’ve got a big game, but for some reason you get all jazzed up and ready to roll. And you’re not tired anymore. That’s how you want to feel about your career, about the job or company you’re taking.”
Forever a cheerleader
Winblad’s a cheerleader for St. Thomas students. She’s spoken several times, including in the classroom, as a commencement speaker and for the Schulze School of Entrepreneurship webinar in 2020 for Women’s Entrepreneurship Week at the Opus College of Business. She also has served as a judge for its business competitions, including e-Fest and the Fowler Business Concept Challenge
Laura Dunham, dean of the Opus College, said “Ann Winblad is both a mentor and a true friend. As a successful entrepreneur and venture capitalist, she eagerly helps aspiring entrepreneurs reach their goals. She has inspired and encouraged our students to pursue their dreams.”
“Ann’s expertise and generosity are inspiring to many of our students, especially aspiring female entrepreneurs,” added Danielle Campeau, the associate dean and Best Buy Distinguished Chair, Schulze School of Entrepreneurship. “As someone who has succeeded in industries dominated by men, Ann has been an inspiration and support to female students at St. Thomas who have expressed interest in entrepreneurship, venture capital and the tech sector.”
Just as Winblad invests in entrepreneurs, she invests in the future of St. Thomas students. She established the Wilbur and Elizabeth Winblad Endowed Scholarship Fund at St. Thomas in honor of her parents. Since the fund’s inception 26 years ago, 706 students have received scholarships totaling $3.6 million.
“Scholarships are really important. Most students need financial aid. And most of them can only come here because of scholarships.”
One Winblad fund recipient was Jake Sundeberg, a first-generation college student who obtained his bachelor’s degree in biochemistry from the College of Arts and Sciences at St. Thomas in 2011. He grew up in Blaine, Minnesota, as one of four boys. The cost of college was going to be a challenge, but he really wanted to attend St. Thomas.
Without the financial support from the Winblad fund, “I never would have been able to achieve my goal of becoming a physician,” he said. Sundeberg has been a doctor at Regions Hospital in St. Paul since completing his medical degree and residency at the University of Minnesota.
“Her decision to focus the endowment on students from middle-income families and those who do not qualify for state or federal grants was visionary,” said St. Thomas President Rob Vischer. “We are blessed by her support, as are the students. The graduates who have been impacted by her support include surgeons, military officers, social workers, engineers, software developers and many more.”
One of those graduates is Lauren Bucholz ’15, who received her bachelor’s degree in leadership management and Arabic. She was raised in River Falls, Wisconsin, by educator parents. After graduation she moved to London to work for a company that contracts with North American universities. “I hope I can convey to Ms. Winblad that these scholarships, for many students, really do mean everything.”
Abigail Fuchs ’20, who received a degree in marketing and started IGNITE, a nonpartisan organization for young women interested in politics, works in the office of Minnesota’s Third Congressional District, said the Winblad scholarship “made an immense impact on not only me, but the St. Thomas community through the continuous support for students at the university, helping us succeed in not only our studies, but in our lives after we graduate. Someday, I too want to be an alumni donor because of the great impact it can make on a student’s life.”
Risk-taker with a song in her head
Winblad said one of the reasons she achieved the success she did when she was still in her 20s was because she was a risk-taker, even then. True entrepreneurs, she said, view uncertainty as an opportunity to innovate and seize the moment, not as risk.
“I know for a lot of young women that there is this dialogue that women feel like they have to be overqualified for a job before they even try to qualify themselves. I never took that approach.”
Her approach was to forge ahead, with a song in her head.
“We used to have cassette tapes in our cars, and I used to play the ABBA song, ‘Take a Chance on Me,’” she said. It’s not so much so that the song built her confidence, she was always confident. It was just a matter of letting others know how capable she was given the times she was living in as usually the only woman at the table, surrounded by older men.
“I didn’t look like the normal person they’re doing business with. And I was trying to explain this new field of software. Then to stop any doubt, I would just have that ‘Take a Chance on Me’ tape play in the back of my head.”
Additionally, she said, “while I have had the privilege of helping to build many great companies, it has been even more gratifying to be in a position to pay it forward. I am eternally grateful to those who long ago gave money for scholarships so I could attend a remarkable university and to see the futures of St. Thomas Winblad scholarship recipients as they go on to become entrepreneurs, doctors, military officers, social workers, engineers, and more.”
Her advice to others is to remember that everybody’s taking a risk on the future. “None of us can predict the future. I’ve been a venture capitalist for 40 years, and I don’t have a crystal ball on the future – I am fortunate that I have a position to audition the future. I’m in the business of taking risk, and that’s a fun business to be in.”
