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Tech Power Players 2023

The Boston tech sector’s defining characteristic in 2023? Resilience.

The Globe’s second annual list of the most influential people in the region’s tech sector tells the story of New England innovation in a challenging economic climate.

What distinguishes Boston’s tech sector is perseverance, determination, and confidence to take the long view — qualities exhibited by the diverse entrepreneurs, financiers, and intellectuals on The Boston Globe’s Tech Power Players 50 list.Adobe Stock images; Globe staff photo illustration

A defining characteristic of the Boston technology industry has always been resilience: the ability to make things happen, no matter the odds.

To illustrate: More than a decade ago, on two successive weeks in December, I met the founders of two startups, eager to show me prototype products that they thought could hit it big.

It was easy to come up with a laundry list of reasons why neither of these companies would succeed. And many potential investors were all too happy to recite that list: entrenched competitors; challenging sales models; the difficulties of designing, building, and supporting consumer electronics at an affordable price.


Today, the first company, Whoop, has raised more than $400 million, employs 500 people, and counts basketball star LeBron James, quarterback Patrick Mahomes, and golfer Rory McIlroy among its users. The second company, Toast, has a stock market value of about $9 billion and employs 4,500 people.

These companies and the entrepreneurs who built them are representative of what distinguishes Boston’s tech sector — perseverance, determination, and confidence to take the long view. And those same qualities distinguish the diverse entrepreneurs, financiers, and intellectuals on The Boston Globe’s Tech Power Players 50 list. I’ve met, in person, roughly 40 of them, and one word would aptly describe them all: bulldozers.

Their ability to bash through any obstacle will become increasingly important as high interest rates, tightening credit, parsimonious venture capitalists, the latest banking crisis, and a slowing economy pound the tech sector. But if Boston’s tech industry has shown anything over the decades — navigating the end of the minicomputer era, a dotcom bust, and a Great Recession — it will find a way to adapt, recover, and forge ahead stronger than before.


Take Toast, for example. In 2012, when I met cofounder Steve Fredette for lunch in Kendall Square, his company was pitching a mobile app that enabled diners to view their checks on their phones and pay with a credit card, rather than wait for the server. When the mobile app proved tough to integrate with existing cash register systems, the company built and sold its own cash register system, which is now found in some 79,000 restaurants.

A handheld device for restaurant servers developed by Toast.Courtesy of Toast

You’ve no doubt tapped your credit card on a Toast cash register in a coffee shop, or watched a server enter your order into one of the company’s ubiquitous, custom-made tablets.

Whoop founders Will Ahmed and Aurelian Nicolae were still Harvard students when I met them at the university’s innovation lab more than a decade ago. They showed off a wristband crowned by a chunky, cream-colored block that resembled a bar of soap, insisting that the sensors inside would tune into your pulse and body movements in a way that other fitness devices couldn’t.

They never complained that Boston was not supportive of startups, or that venture capitalists said “no” a lot, or that it was hard to find a VP of marketing with deep experience in a specific industry. They just got it done.

“Almost everyone I spoke to told me in some form or another that we would fail,” Ahmed recalls. “I just put up a wall to negative feedback.”

Rory McIlroy of Northern Ireland wearing a Whoop wristband during a practice round prior to the 2023 Masters Tournament at Augusta National Golf Club on April 4, 2023 in Augusta, Georgia. Patrick Smith/Getty

If the innovation ethos of Silicon Valley is, “Go big or go home,” then Boston’s might be, “Patience is a virtue.” Stefania Mallett, CEO and cofounder of ezCater, which operates a marketplace of restaurants and catering companies serving business customers, describes the key characteristic of the local tech scene as “grounded-ness.”


Grounded companies spend more time solving problems, and more time scaling up teams to sell the solutions. Boston has the patience to support a biotech company that may need a decade or more to perfect a way to attack a disease or create a new kind of vaccine. “It’s a very valuable trait, and nothing to be apologetic for,” Mallett says. “Thank you, Moderna.”

Boston, adds Katie Rae, CEO of The Engine, a venture capital fund started by MIT, is “the best place in the world for entrepreneurs who want to work on tough tech” — new approaches to personalized cell therapy, nuclear reactors, or massive batteries to store renewable energy.

But Boston being Boston, there is always a certain amount of analysis about what we could do better, and why we’re not spawning companies that grow to 50,000 or 100,000 employees, as we did in the days of Polaroid, minicomputer maker Digital Equipment Corp., or Lotus Development Corp., the company that introduced spreadsheets and e-mail into corporate America.

One opportunity might be generative AI, the technology that elbowed its way to center stage last year with the debut of apps such as ChatGPT. I spoke to Brian Halligan, cofounder of HubSpot and now a venture capitalist, just after he returned from San Francisco, where he attended several events focused on the new field. “There’s a new wave upon us, and that’s the generative AI wave,” Halligan says. “We have a lot of smart people. We have an opportunity to hop on this one.”


Boston entrepreneurs Steve Papa, cofounder of Endeca, Dileep George, cofounder of Vicarious AI, and Brian Halligan, cofounder of HubSpot, spoke to Anna Patterson, partner at Gradient Ventures, about uses for AI programs like ChatGPT at the Imagination in Action conference at MIT on April 13, 2023. JOHN WERNER

Boston can do better connecting its tens of thousands of college students with internships or employment in tech, or with resources to start their own companies, says Eric Paley, managing partner at Cambridge venture capital firm Founder Collective. It can also do more to make entrepreneurial education and early-stage funding accessible, building on efforts, such as Visible Hands and Entrepreneurship for All, to help underrepresented founders.

Niraj Shah, CEO of home-furnishings company Wayfair, raises other concerns. A good job is no longer enough to pull talent to Boston. When workers can live and work wherever they park their laptops, it’s essential for the state to focus on “transportation and housing challenges that are not getting better,” Shah says. “If you’re a business trying to attract people to the area, it’s getting tougher.”

When I spoke to Mallett of ezCater on a Wednesday, the population of her office near Post Office Square looked sparse. The company’s 800 employees work in 40 states and Canada. I asked Mallett about where her next 100 hires would be based. Her answer: “They could be anywhere.”


Stefania Mallett, cofounder and CEO of ezCater, poses for a portrait at her offices in Boston on Oct. 15, 2019. Craig F. Walker/Globe Staff/The Boston Globe

Some companies still believe in the power of proximity when you’re designing a 3-D printer, a robot, or a wrist-mounted device to monitor your health. Whoop, now designing apparel, is one of them. I dropped by Ahmed’s office on a Thursday in March, in part to introduce him to Fredette, the Toast cofounder. I was surprised the two had never met, despite their offices being a five-minute walk apart in the Fenway neighborhood.

Both Ahmed and Fredette say young entrepreneurs are programmed to be impatient, always urging their colleagues to do more, faster. But looking back to Toast’s early years, Fredette says, “It takes 10 years to build anything of consequence.”

The round table in Ahmed’s office was covered by Toast’s rugged black tablets and Whoop’s wristbands, now small, light, and sleek — no bulky bars of soap here. It happened to be opening day at Fenway Park, where a giant Whoop logo looms just to the left of the iconic Citgo sign.

Overhead, a plane towed a banner advertising DraftKings, another Boston company. A few blocks away, a building under construction sported the logo of CarGurus, an automobile listing site that went public in 2017.

From Ahmed’s office window, it did not look like a bad city in which to start a tech company.

The Whoop sign as seen from inside of Fenway Park on May 16, 2022.Jim Davis/Globe Staff

Scott Kirsner can be reached at Follow him @ScottKirsner.