The key to making great investments, Don Valentine once said, is to “assume that the past is wrong, and to do something that’s not part of the past, to do something entirely differently.”

He did just that in 1960. Having studied chemistry at Fordham, he quickly grasped how silicon would transform the electronics industry. He joined the seminal startup Fairchild Semiconductor and was among the first to market and sell the silicon chip, the technological breakthrough at the heart of the digital age.

In 1972, he established the venture firm Sequoia Capital. Its first investment was in Atari, the pioneering arcade and home video game company. Valentine later met a young Atari employee named Steve Jobs, and with a $150,000 check in 1978, became one of the earliest investors in Apple Computer.

“When we invested in Apple … nobody had a personal computer,” Valentine said in a 2009 oral history interview. “The cheapest computer was $250,000. And Steve’s vision was, we’re going to make them so that everybody will have one. Pretty simple.”

Throughout his career, Valentine funded and advised entrepreneurs who went after big markets—the one for personal computers with Apple, for databases with Oracle, and for routers with Cisco Systems, the networking company Valentine led as chair for three decades.

He was known for asking startup founders, “Who cares?” in response to their pitches, urging them to hone their own ability to ask the right questions. It’s a habit of mind he attributed in part to his Jesuit education at Fordham, where he said faculty favored the Socratic technique of teaching. “My middle initial is T for Thomas, the doubting person,” he said in the 2009 oral history interview, noting that his natural “inquisitiveness and inclination not to believe what I was told or heard” had served him well.

Valentine died last October at his home in Woodside, California, at the age of 87. He had stepped aside from leading Sequoia in the mid-1990s, though he stayed involved with the firm, which has since partnered with Google, LinkedIn, WhatsApp, and YouTube, among other companies.

In recent years, he met with students and alumni of Fordham’s Gabelli School of Business at the University’s annual entrepreneurship dinner in Silicon Valley.

“Don Valentine was an incredible pioneer in so many ways,” said Gabelli School Dean Donna Rapaccioli, Ph.D., GABELLI ’83. “It was a privilege to spend time with him on several occasions—he pushed me and everyone around him to think more strategically and to tell a more compelling story.”

A Knack for Electronics

‘They Grow Fast, They Grow Big, and They’re Very Dramatic’

Looking for Big Markets, Leading with the Right Questions

Throughout his career, Valentine funded and advised entrepreneurs who went after big markets—the one for personal computers with Apple, for databases with Oracle, and for routers with Cisco Systems, the networking company Valentine led as chairman for three decades. He often encouraged entrepreneurs and would-be entrepreneurs to develop their listening and storytelling techniques. And he was known for asking startup founders, 
“Who cares?” in response to their pitches, urging them to hone their own ability to ask the right questions.

“My middle initial is T for Thomas, the doubting person,” he said in the 2009 oral history interview, noting that his natural “inquisitiveness and inclination not to believe what I was told or heard” had served him well as both an entrepreneur and venture capitalist.

It’s a skill that he saw in Apple co-founder Steve Jobs, “one of the best interrogators that I have ever either seen or heard,” Valentine said. “Somehow or other he knew what to focus on and how to build a sequence and series of questions that were additive to the answers.”

Valentine stepped aside from leading Sequoia in the mid-1990s, though he stayed involved with the firm, which has since expanded beyond Silicon Valley to Israel, China, and India, and partnered with companies including Google, LinkedIn WhatsApp, and YouTube.

In recent years, Valentine met with students and alumni of Fordham’s Gabelli School of Business at the University’s annual entrepreneurship dinner in Silicon Valley.

“In a few short minutes, Don proved to be a great teacher and mentor,” Chase McQuillan, GABELLI ’17, told Gabelli Connect in July 2015, when he was a rising junior at the Gabelli School and a member of the Fordham Foundry, the University’s hub for innovation and entrepreneurship.

“Don Valentine was an incredible pioneer in so many ways,” said Donna Rapaccioli, Ph.D., GABELLI ’83, dean of the Gabelli School of Business. “It was a privilege to spend time with him on several occasions—he pushed me and everyone around him to think more strategically and to tell a more compelling story.”

Valentine is survived by Rachel, his wife of 58 years; their three children, Christian, Mark, and Hilary; and seven grandchildren.

Gianna Migliorisi has worked in tech for more than a decade, but until last spring, she didn’t realize just how unwelcoming the industry could be for women.

“My entire career I was walking around, oblivious, thinking that I was no different from any of my male colleagues, that every other woman in technology was treated with the same respect and equality that I had been fortunate enough to encounter in the workplace,” she wrote in a post on Medium.

Her epiphany came at the 2018 Women of Silicon Valley conference in San Francisco, where she heard stories of female software engineers who had to work harder than their male counterparts in order to gain approval, or sometimes, even to get in the door. According to the National Center for Women & Information Technology, only 26% of professional computing jobs in the 2018 U.S. workforce were held by women, and only 20% of Fortune 500 chief information officer (CIO) positions were held by women in 2018.

The conference was such an eye-opener for her, she says, because she has always felt supported in her academic and career choices.

“I didn’t really appreciate how important it is for women in a science field to be recognized, because there are not many of us,” she says.

The Brooklyn native not only grew up with parents who both worked in the sciences—her mother is a scientist who taught anatomy to medical and nursing students, and her father is a pharmacist—but she also received a great deal of encouragement from faculty at Fordham.

During her sophomore year, computer science professor Robert Moniot, Ph.D., nominated her for a Clare Boothe Luce Scholarship for women in the sciences. The award gave her the financial support to enroll in Fordham’s dual-degree program in computer science. She began taking graduate-level courses as an undergraduate, and earned her master’s degree in 2008.

While finishing her master’s, Migliorisi began working at National Grid, the utilities company. She later joined HBO, where she was part of the team that launched the HBO Go app, and worked at a software company before joining Discovery Inc. in August 2015. As a senior director of technical product management, she works with engineers to build features and products for the company’s streaming apps, including those for TLC and Animal Planet.

Her professional success, and the experience she had at the Women in Silicon Valley Conference, has led Migliorisi to try to make sure she creates an environment in which other women can succeed.

“I’ve been making a conscious effort to try to be more supportive of [my women colleagues’]particular struggles,” she says. “I definitely make it more of a priority now to hire more women and make sure I look around to make sure other people are hiring more women.”

Migliorisi knows she was fortunate to find at Fordham an environment where she felt supported and could develop her skills and confidence.

“[My professors] never discouraged me from anything and never made me feel like I wasn’t capable of doing this job or learning,” she says. “They were super helpful, especially when you needed that extra effort, and they had a genuine interest in your success. I had a really, really good experience.”

Beyond academics, Migliorisi was a member of the Commuting Students Association, an orientation leader and orientation coordinator, and a member of the Senior Week Committee.

“As a commuter, I wanted to feel like I had a connection to my school and make sure that other commuters had that connection, too,” she says. “Fordham did a great job of catering to commuting students and making resources and activities available for them to be a part of.”

That positive experience has led Migliorisi to stay involved with Fordham however she can, from donating to attending events.

“Really, I had such a wonderful experience there that I definitely believe in giving back to a place that I feel like shaped me as a person.”

Fordham Five

What are you most passionate about?

This is hard because I get excited about a lot of things … but I feel like I’m most passionate about making others happy. I bake a lot, which relieves stress for me, but I bake things and bring them to work because it makes everyone so happy. Little things like that. Saying thank you for something small, buying someone some flowers to cheer them up … giving hugs … organizing happy hours. Everyone works really hard, and I like to make sure they know they’re appreciated, so it makes me happy to make others happy.

What’s the best piece of advice you’ve ever received?

“No one wants to mess with something that’s working.” My manager always reminds me of that when there is a lot of change going on in the workplace, and when certain changes can lead to uncertainty. Change isn’t easy, and when the future is uncertain, it makes it harder sometimes to concentrate and do your job. Remembering to just do your best and keep focusing on your mission will help you navigate the waters of change, and most of the time, bad change won’t come your way if things are going in the right direction.

What’s your favorite place in New York City? In the world?

How do you pick one place in New York City? I think anywhere there’s a spot of green in NYC is my favorite place. There’s nothing like hanging out at Bryant Park on a nice summer afternoon. In the world: Anywhere where there’s a beach with nice warm water is my happy place.

Name a book that has had a lasting influence on you.

Extreme Ownership: How U.S. Navy SEALs Lead and Win, by Jocko Willink and Leif Babin, has had a huge influence on me, particularly as a leader in a work environment. It teaches you to take ownership of everything, including the mistakes of a team. If you’re a leader, and your team is underperforming, it’s not their fault, it’s yours. You as a leader, no matter what situation you are in, have an obligation to the people you lead—to build trust, encourage, and inspire them. If someone on your team fails, it’s because you failed in some way. Never misplace the blame; always own your mistakes.

Who is the Fordham grad or professor you admire most?

Professor Stuart Sherman in the English department. I absolutely hated English classes, and English professors didn’t like me that much. I was never very good at analyzing things from a creative perspective (I’m a logical thinker) and my writing wasn’t amazing. Professor Sherman took the time to help me be a better writer. He taught his courses with so much passion and love and enthusiasm, it was infectious. He made me love a course I absolutely hated, and in my mind, that is the mark of an amazing teacher. I may not remember everything I learned in his classes, but I remember him for his energy and his kind heart and his love for teaching.

“It’s important you understand my goal,” says Calacanis, a veteran tech entrepreneur and an early investor in Uber and other successful startups. “I like winning. You’ve been picked by us out of all the hundreds of companies that applied—and by us, I mean me—because you can win. You are here to win. We’re going to win together.”

Calacanis started Launch to support entrepreneurs and inspire innovation. In addition to the incubator classes, he hosts the annual Launch Festival, a startup conference that draws thousands of attendees. He claims he might cut back on his involvement with the class this year, since he and his wife recently had twin girls (they also have a 6-year-old daughter). But he doesn’t seem to believe it. Just seconds later, he says he’ll probably come to all the sessions. And besides, it hasn’t been a time of cutting back for Calacanis. He also hosts This Week in Startups, a podcast named by several tech sites as one of the best of its kind, and he’ll soon star in a reality TV show he’s co-creating for Harvey Weinstein’s company about—no surprise—startups.

The show will be authentic, he promises, and different from others on entrepreneurship, such as Shark Tank, in that it will focus on how startups are actually created. He’ll personally pick the participants and judges, he says, and the show will help him achieve his goal of becoming the greatest angel investor of all time, helping others build wildly successful companies.

In class, Calacanis advises the entrepreneurs, often lacing his insights with expletives and exclamations. He decries Silicon Valley “tourists” who just want to get rich quick with “apps no one wants!” And he says there used to be too much money in startups, “now there’s no money!” But he tells his students they’re hard workers with skills and a real product, and he says what venture capitalists need to hear is simple: Who are your customers, how much money do they give you, and what’s your profit margin? Grinning broadly, he says it takes less than 30 seconds to make that kind of pitch, “and it’s everything investors want! Anything else is window dressing!”

A few days later, at his Launch offices in the Tenderloin district, Calacanis says there’s a good reason why he seems to be having the time of his life in his class: He is.

Calacanis has been in the tech world a long time. He started the Silicon Alley Reporter back in the mid-1990s and built it from a 16-page newsletter to a glossy magazine of a few hundred pages, becoming a key player in the internet industry as it was taking off in New York City. He not only published and edited the magazine, he delivered it as well, pulling a luggage cart around Manhattan. On the masthead, he listed himself as “Publisher, Editor, and Delivery Boy.”

The New Yorker called him “the kid who hooked up New York’s wired world,” and Charlie Rose, 60 Minutes, and other old-media giants sought the insights of the upstart publisher from Bay Ridge, Brooklyn, with a bartender father and a mom who worked as a nurse. He says it was a heady time. “All of a sudden you get to pick who’s on the cover of the magazine in the hottest technology sector in the history of mankind. There’s billions of dollars at stake, and you have 75 people working for you at the age of 27. For a kid with no power from Brooklyn who had to hop the turnstile, it’s pretty awesome.”

He displayed that kind of hustle getting into Fordham, a story he recounts fondly. With less-than-stellar grades, he knew Fordham was a long shot. But he was determined to go, so he listened to his taekwondo teacher, a Fordham alumnus, who told him to be persistent. Calacanis stayed in touch with an admission officer, bringing him reference letters from teachers and bosses, and showing him his senior year grades, which had risen significantly. Finally, Calacanis says, the admission officer told him he was leaving Fordham, and his last act at the University would be to grant admission to the most promising nontraditional student. When Calacanis told his father, his dad responded by saying that he’d just lost his bar for nonpayment of taxes. Good luck paying for school, he told his son.

After all that work to get in, Calacanis wasn’t going to let not having the tuition stop him. He went to Fordham full time at night and worked multiple jobs—as a barback, a waiter, and a tech in the University’s computer labs. He says he brought that work ethic to his founding of Silicon Alley Reporter. After it folded in the dotcom crash, he co-founded and built Weblogs Inc., a network of blogs supported by advertising. A few years later, in 2005, he sold it to AOL for more than $25 million.

Calacanis has called his investing success “dumb luck.” But as an early investor in Uber, Thumbtack, and other billion- and multimillion-dollar companies, he doesn’t actually believe that. “I say it as a joke to see if people are paying attention,” he says. “When I tell people I got lucky seven times, I’m trying to make a point to them, whether they get it or not, that I’m not lucky, I’m hardworking.”

Back at his Launch offices, Calacanis is summoned to get made up for his podcast. He continues talking as he walks upstairs. Now that he’s in his 40s, and he’s made his money and has a family, he says he’s outgrown his immature impulses to prove that his successes were more than just luck. And he wants to share his advice with a broader audience. Most reality shows are silly, he says, but if done well, they can teach people something about fashion, say, or cooking. He wants to do that for entrepreneurship—and not just for the ratings but for a fame that’s more lasting.

“I don’t need to be a celebrity or get any more press,” he says. “It all goes back to the grand plan to be the best angel investor of all time.”

—Emily Wilson