How a veteran entrepreneur is helping Microsoft double down on startups
No one would have thought Jeff Ma would land where he did, least of all Ma himself.
For decades, Ma has been known in Silicon Valley as an entrepreneur who launched and sold several successful and diverse companies. More famously, he was a member of the MIT blackjack team that won millions from Las Vegas casinos and the inspiration for the main character in the movie “21” and the book “Bringing Down the House.” Ma has been an options trader, was a water polo coach for years, is an author and professional speaker, and has been a writer and on-air personality for ESPN.
He is, in other words, someone who defies easy pigeonholing. And when Ma took on a new role in the spring, the move raised eyebrows across Silicon Valley’s startup community. The seasoned entrepreneur with the colorful and unpredictable career was going to … one of the world’s tech giants?
“The fact that he went to Microsoft is a big deal,” said Kevin Compton, former operating partner at Kleiner Perkins and now co-founder of Radar Partners, a venture capital firm based in Palo Alto. “People were surprised. He could have gone anywhere, and he went there.”
In April, Ma became the vice president of Microsoft for Startups, a program launched in 2018 to give startups access to Microsoft’s technologies and marketing expertise and allow them to co-sell their products through the company’s global sales force. Ma was working on a consulting project when his longtime friend Eric Boyd, corporate vice president of Microsoft’s AI platform, approached him about the job. Boyd figured Ma would be a good fit, but Ma was initially skeptical. He’d been an entrepreneur for decades and just couldn’t see himself working for Microsoft.
But Ma knew Microsoft’s culture had shifted dramatically since CEO Satya Nadella took the reins in 2014, and he was intrigued. He flew up to the company’s headquarters in Redmond, Washington, and met with some executives. What he heard and saw convinced him that there was a unique possibility before him, a chance to do more for entrepreneurs whose needs and challenges he understood as well as anyone.
“I realized it was a huge opportunity,” he said. “Satya has made it clear that nurturing an ecosystem and making our partners successful is ultimately the most important thing to us.”
Six months into the job, Jeff Ma is proactively seeking out targeted startups and strengthening Microsoft’s presence in Silicon Valley.
Now six months into the job, Ma is shaking up Microsoft’s startup strategy, proactively seeking out targeted startups and strengthening Microsoft’s presence in Silicon Valley, where, he acknowledges, the company has traditionally not been top of mind for startups. Ma aims to change that through a feet-on-the-ground approach — talking to entrepreneurs about what Microsoft can do for them and raising awareness among venture capitalists and other influencers.
“It’s ultimately the place we need to win. It’s the place where most of the successful startups come out of, and it’s the ecosystem that will have the greatest impact broadly on the rest of the ecosystem,” said Ma, who lives with his wife and their 1- and 3-year-old sons in Belvedere, just north of San Francisco.
Compton and others say if anyone can raise Microsoft’s profile in the hyper-competitive Silicon Valley, it’s Ma. They describe him as universally known in the valley’s startup world, an inclusive leader who builds teams of talented people and draws the best ideas from them. He’s charismatic, highly inquisitive and intensely smart, they say, able to process information and look at data in ways other people don’t, but also down-to-earth and fun to be around.
Ma is the type of person, Boyd said, who doesn’t just go to a restaurant, enjoy the experience and leave, like most people. He’ll chat up the chef, get to know the employees and strike up relationships.
“He’s a connector. He talks to everybody,” Boyd said. “He’s that type of personality that’s always sort of seeking out and finding people. I imagine he knows everyone in the valley and, if he doesn’t, then he knows someone who can get them in touch with them. In the startup world, connections are everything.”
Ma likes to talk about specialized versus generalized learning. A massive sports buff, he frames the distinction in those terms: Tiger Woods played golf from day one and is a specialized learner, he said, while Roger Federer was a generalized learner who played sports other than tennis while growing up. Ma is firmly in the latter category.
Born in Worcester, Massachusetts, to a chemical engineering professor father and a nurse anesthetist mother who both emigrated from China after the Communist takeover in 1949, Ma was the youngest of three children and the only boy. His parents were hardworking, strict and ambitious, sending their two daughters and son to the prestigious Phillips Exeter Academy in New Hampshire. Ma’s sisters enrolled as sophomores but he went as a freshman: As a strong-willed kid who was “too smart for my own good,” he chafed against his parents’ expectations and was eager to go away to school.
Ma graduated from Exeter and then the Massachusetts Institute of Technology, where he received a degree in mechanical engineering in 1994. His father wanted him to become a doctor and he did enroll in pre-med but eventually realized medicine wasn’t for him. It was hard to let his father down, Ma said. He thinks about the sacrifices his parents made, how selfless they were about giving him and his sisters opportunities to succeed.
There’s a story about Ma’s father that stands out in his mind. He arrived in Seattle on a boat from Taiwan, then took a train to South Bend, Indiana. He had only about $50 on him and bought two hot dogs for the trip, but was so anxious about spending money that he couldn’t bring himself to eat them.
“I think about the times that I’m sitting around on a weekend with friends drinking wine, just enjoying ourselves. And I just don’t think my parents ever had many moments like that in their life,” Ma said. “It’s not really what they wanted and it’s not what they were ever able to allow themselves to do. Everything they did was for us.”
The summer after Ma’s senior year, he was living in his fraternity house with a couple of friends who were playing on the MIT blackjack team as a summer job. Ma liked to play poker but thought there was something a little unsavory about gambling in casinos. Still, he wanted to hang out with his buddies, and when he found out how much they were making, he was willing to give it a try.
Ma started flying to Vegas with the team on weekends, winning at blackjack by counting cards. He got good at it — so good that he became one of the team’s top players, helping the team win around $5 million during the seven years he was part of it. One night at an Irish pub in Boston, he met writer Ben Mezrich and told him about his experiences on the team. The main character in Mezrich’s book is based on Ma; the book was followed by the movie, with Ma making a cameo as a blackjack dealer in Vegas.
Looking back, what Ma misses most about those days isn’t the lavish lifestyle or the excitement of beating the casinos — it’s the camaraderie.
“We were a real team. The only other times I’ve felt that amount of collegiality was when I started companies,” he said.
Ma left the team in 2001, taking with him valuable lessons about how to analyze and apply data, stay with a data-driven approach and avoid bad decisions based on emotion or bias. He detailed those insights in a 2010 book, “The House Advantage: Playing the Odds to Win Big in Business,” and applied them in the four companies he launched: instructional golf site GolfSpan.com (sold to Demand Media), loan management company CircleLending (sold to Virgin), fantasy sports site Citizen Sports (sold to Yahoo) and productivity web service tenXer (sold to Twitter).
Ma spent three and a half years at Twitter, where he was vice president of analytics and data science. His presence and network in Silicon Valley, success as an entrepreneur and experience working for an established company like Twitter made him the ideal person to head Microsoft for Startups, said Charlotte Yarkoni, Microsoft’s corporate vice president for Cloud + AI.
“Jeff is a tenured entrepreneur who’s had multiple startups. Amazingly enough, they’ve all had a positive exit, which is really challenging to do,” Yarkoni said. “It’s a really, really substantial skill set you have to have to be an entrepreneur and be successful.
“Part of what we were looking for was a seasoned entrepreneur who had been in the startup space,” she said, “but who also had the maturity to understand and be able to leverage the broader benefits of a large company like Microsoft so we could achieve our aspiration of helping startups be successful, regardless of what their stage of maturity is.”
We’re going to try to do a lot to change the way the entrepreneurial mix looks, from a diversity and inclusion, gender and opportunity standpoint.
Evan Reiser wasn’t even considering using a different cloud provider for his San Francisco-based security startup, Abnormal Security Corp. But Ma reached out a few months ago and told him about the support Microsoft for Startups could offer his two-and-half-year-old company beyond just technology.
“My immediate response was, ‘What are you talking about? Isn’t it all about technology?’” recalled Reiser, Abnormal’s CEO.
The business benefits of Microsoft prompted Abnormal to move its software onto the Azure platform. Under the partnership, Abnormal’s cybersecurity solution is now available to Microsoft’s large enterprise customers through its cloud storefronts, Azure Marketplace and App Source, as well as through its co-selling relationship. Those customers get Azure consumption credits for buying Abnormal’s solution and can purchase and easily integrate it directly through Microsoft, eliminating the lengthy procurement cycle that can sink startups.
Reiser said he’s impressed by Microsoft’s commitment to security and the advanced technologies, like Microsoft Azure Cognitive Services, accessible through Microsoft for Startups. The partnership strengthens Abnormal’s credibility, he said, and makes it easier to get in front of Fortune 500 companies.
“Our investment in the Microsoft ecosystem has helped us grow very quickly,” Reiser said. “I’m impressed from the top level down that there’s commitment from Microsoft to invest in startups and ultimately to enable all developers, whether at small companies or big companies, to build innovative things on their platform.”
Spending most of his days lately at home on Teams calls, Ma has been building his own team, which so far includes about 55 employees. His colleagues say he’s a leader who has strong opinions and is not afraid to disagree, but who is also caring and collaborative.
“Jeff is a really good leader because he sets very clear direction and a very clear strategy, but trusts you to do the right thing and execute against that strategy however you see fit,” said Lahini Arunachalam, Microsoft for Startup’s director of product management, who first worked with Ma at a tech company in 2018.
“He’ll listen to your opinion, listen to people on the team,” she said. “He wants to understand what’s going on, not only from a work perspective but also from a life and morale perspective. He cares deeply about his team and the people on his team.”
There are already thousands of companies in the Microsoft for Startups program, and Ma is focused on how to best support them and attract new ones in several different sectors. Longer term, he has two main goals in his role. He wants to shift the perception of Microsoft so entrepreneurs worldwide see it as the tech leader they want to work with. And he wants to create new programs and opportunities to help increase the number of startups launched by women and underrepresented minorities.
“Startup opportunity is definitely not distributed equally now, and it needs to be,” Ma said. “With Microsoft’s resources and ideas, we’re going to try to do a lot to change the way the entrepreneurial mix looks, from a diversity and inclusion, gender and opportunity standpoint.”
Ma’s oldest sister, Vivian, also worked for Microsoft before passing away in 2015. It’s bittersweet for him, thinking about how she would feel about his new role. “She would be so proud. I can only imagine how amazing it would be to be working here with her,” he said. “She would always still treat me like her little brother, which I think would be funny.”
Ma sees his position at Microsoft as a fortuitous confluence of choice and chance. His education — Exeter’s liberal arts environment and the technical world of MIT — and diverse career gave him a broad range of experience to bring to the role. But it was serendipity that Boyd thought to reach out to him about the job, he said, and serendipity that the opportunity came about during the COVID-19 pandemic, when a position at stable, thriving Microsoft was especially appealing.
“In many ways, I’ve never had any real idea of what I wanted to be. Even when I was an entrepreneur, it wasn’t really an intentional thing. It was, ‘This is an opportunity to learn and do something interesting.’ And that’s what I did,” Ma said.
“The Microsoft job is the first one that I have actually looked at and been like, ‘I’ve been building toward this my whole life, and it’s cool.’”Originally published on 10/30/2020 / Photos by Brian Smale / © Microsoft