Tech Winners & Losers of 2019

Is presidential candidate Andrew Yang the Tech Winner of the year?
Sheila Fitzgerald/Shutterstock
Is presidential candidate Andrew Yang the Tech Winner of the year?

Tech Winners & Losers of 2019

From New York’s longest standing Democratic presidential contender to the billionaire who couldn’t hack it in Queens, here are the year’s biggest tech winners and losers.
December 19, 2019

Sentiment against Big Tech has been building for a few years now, but 2019 may be the year that pent-up disdain came to the fore, as both federal and local governments probe how those companies amass market power and treat users’ data, for example. Lawmakers, public officials and tech executives themselves now have to navigate a new normal, wherein tech is no longer welcomed with open arms but is still essential for big cities and small towns alike to thrive. While the eyes of the nation have traditionally been fixed on Silicon Valley to spot who’s on top in the world of technology, it’s increasingly the case that some of tech’s biggest winners and losers reside – literally and figuratively – in New York. The loss of Amazon’s planned headquarters in Long Island City may be the biggest story of the year, but it’s not the only New York tech story in 2019, crazy as that notion may seem. From an upstate elected official to an ousted New York City agency head, City & State looked back at a tumultuous year in tech and picked out its biggest winners and losers.

Andrew Yang

Schenectady native and former tech executive Andrew Yang is making a name for himself in the Democratic presidential primary. Even if he is not selected as the Democrats’ choice to take on President Donald Trump, this math-loving, tie-hating New Yorker is a winner this year. Yang rose to prominence on his plan to give all Americans $1,000 per month, and this universal basic income idea brought not only Yang himself but the topic of automation and artificial intelligence to the debate stage and campaign trail. Even if he doesn’t advance beyond the primary, Yang will carry his hordes of online fans and friends in Silicon Valley to whatever his next endeavor is.

Ben Walsh

At the beginning of the year, when Syracuse Mayor Ben Walsh announced a tech-focused economic development initiative dubbed “Syracuse Surge,” the news may have caught some sidelong glances and critical comparisons to another alliterative upstate project, the Buffalo Billion. But in that time, Walsh landed on City & State’s winners list no fewer than three times for helping to establish Syracuse as an upstate tech hub. Syracuse, after all, has secured a 5G deal with Verizon and is home to a recently completed drone test corridor. Now, all that’s left is for Walsh to get Syracuse off that list of the nation’s most impoverished cities.

Andrei Greenawalt

Ride-hail giants like Uber and Lyft skated by in New York City up until late 2018 and early 2019, when a bevy of new regulations – like a minimum wage for drivers, a cap on new for-hire vehicle licenses and a congestion surcharge – were passed or went into effect. But even amid the city’s reining in of these app-based services, one winner emerged. Andrei Greenawalt, who heads public policy at the ride-share company Via, has had an easier time with some of the new rules – like a cap on time spent cruising without passengers in Manhattan – because Via’s cruising stats are already below the new limits. And rather than entangle itself in lawsuits against the city like its competitors, Via was selected by the city Department of Education to provide routing and other services for its nearly 10,000 school buses. As government sours on tech, Greenawalt appears to know how to stay on the city’s good side.

Jeff Bezos

If Rep. Alexandria Ocasio-Cortez, state Sen. Michael Gianaris and New York City Councilman Jimmy Van Bramer were the winners of 2019, then Amazon founder and CEO Jeff Bezos is undoubtedly a loser. While the $100 billion man may not have that much to lose sleep over, his failure to cement a new Amazon headquarters in Long Island City this year is a stain on Bezos’ record – a record that some are beginning to criticize in earnest, as reports suggest that the poor working conditions at his company’s fulfillment centers leave workers vulnerable to injury. It can’t feel good to be chased out of Queens and still have its politicians yelling after you months later.

Samir Saini

New York’s tech officials don’t have a track history of keeping long tenures with government agencies, and Samir Saini, the former head of the New York City Department of Information Technology and Telecommunications, is no exception. After just 18 months, Saini resigned his post in June to take a job in the private sector, but it’s unlikely his only reason for leaving was a higher payday. Saini was blamed for the crash of the city’s wireless network in April that took down remote controls for 12,000-plus traffic lights and NYPD license-plate readers. Look, we’re not all IT experts, but as the federal government provided a warning about how to prevent this specific crash, Saini shouldn’t be surprised that he was the one left holding the bag for this failure.

Adam Neumann

 WeWork founder Adam Neumann was set to lead New York’s first tech decacorn – a company valued at over $10 billion – to its initial public offering this year, but by October those plans had been shelved and Neumann was out as CEO, leaving investors to pick up the pieces and save the crumbling company from bankruptcy. WeWork is arguably not a tech company, but Neumann has been counted alongside former Uber CEO Travis Kalanick and Twitter CEO Jack Dorsey as one of technology’s mythical and eccentric founders. And now all Neumann has left is WeWork’s failed legacy. That, and $1.7 billion.

Annie McDonough
Annie McDonough
is a tech and policy reporter at City & State.