The fight over gig work is ugly, expensive, and nowhere near over

No: “Massachusetts isn't for sale.” Gig companies: “Wanna bet?”

A car-shaped piñata

The fight for votes has become less about substance and more about a glut of cash — a bit like the tech industry itself, in 2022.

Illustration: Christopher T. Fong/Protocol

When Uber, Lyft, DoorDash and Instacart emerged victorious in their California campaign to continue classifying gig workers as independent contractors, they left behind a battlefield so flooded with cash that their opponents drowned in it. The most expensive ballot measure in California history cost the companies a little over $200 million; their opponents spent just $20 million.

Now, the gig companies have brought the Proposition 22 fight to Massachusetts. They are expected to once again break records for campaign spending, quite possibly surpassing the state record of $60 million spent across all ballot measures in 2020. Lyft already broke the state’s one-time political contribution record when it made a $14.4 million donation late last year.

The “No” campaign — led by labor groups — admits its defeat in California was crushing. But its new leader, Wesley McEnany, thinks he has a novel strategy that could actually prevent the same type of bloodbath.

For McEnany, fresh from two years helping to lead the campaign to unionize tech workers at the Communication Workers of America, there’s no question that the ballot measure in California, and the similar one now proposed in Massachusetts, are deeply unfair to the companies’ workers. But he also believes that if the campaign keeps the fight solely about the workers themselves, they could lose again.

So instead, the campaign has rebranded itself from the “Coalition to Protect Workers Rights” to “Mass Not For Sale.” For the next eight months, McEnany and the “No” coalition will argue to the commonwealth of Massachusetts that “Big Tech” is trying to buy a law, and that voters should be outraged. “Big Tech” is a popular public enemy these days, so the “No” coalition plans to take advantage of that trope and bring up issues like privacy, safety and antitrust.

“Here we have corporations that are willing to spend hundreds of millions of dollars to use a ballot measure process to buy a law,” he said. “We are talking about workers — workers are going to be a very centered strategy, and drivers are part of the strategy. But if we allow the conversation to strictly be about one thing, the amount of resources and money [these companies] have to sort of confuse that issue is undeniable.”

The “Yes” campaign, represented by a group called the Massachusetts Coalition for Independent Work, is so confident in its legislative strategy that its spokesperson, Conor Yunits, told Protocol he was almost certain the Massachusetts legislature would create a law enshrining protections for gig-work companies before the ballot question ever reaches the ballot box. But in case the legislature does not, the campaign already has more than $17 million in the bank — and the opposition expects that to swell to $100 million by November. (Protocol contacted Uber and Lyft for this story. Uber did not respond and Lyft directed us to Yunits).

The fight for votes has become less about substance and more about a glut of cash — a bit like the tech industry itself, in 2022.

Despite the financial shenanigans, this fight has enormous implications for the future of work. Millions of full-time American jobs that currently provide health insurance and sick leave are primed to be giggified. This giggification is already spilling over into other sectors, such as health care: In California, a new Prop-22 simulacrum has emerged that proposes to classify health care workers who find their jobs on digital platforms as independent contractors, much like ride-hail and delivery drivers. And if the gig companies succeed in the deep blue, labor-friendly Massachusetts, they’ll have a political playbook ready to export around the U.S.

A three-pronged approach

The gig companies are fighting their case in courts, in the Massachusetts legislature and potentially on November ballots. This three-pronged approach is part of what makes this campaign so complicated and expensive. It also shows the gig companies have adopted a more sophisticated approach since the California Prop. 22 campaign — in Massachusetts, the coalition has a plan, a backup plan and a backup-backup plan.

The first prong — the court battle — kicked off in July 2020, when Massachusetts Attorney General Maura Healey (now the Democratic front-runner in the state’s gubernatorial election) filed a lawsuit arguing Uber and Lyft drivers should be classified as employees under existing state law.

Healey asserted that Massachusetts Wage and Hour Laws required gig companies to reclassify workers as employees. These laws had been in place for years, but hadn’t been enforced for gig companies. Healey’s lawsuit sought to grant gig workers access to minimum wage guarantees, earned sick time and overtime. (At the start of the pandemic, Uber and Lyft gave drivers limited assistance in the form of stipends for those who tested positive for COVID; drivers struggling to make ends meet later became one of the largest cohorts to receive federal aid under the Economic Injury Disaster Loans program.)

In March 2021, Uber and Lyft lost a motion to dismiss the lawsuit. While the suit is still ongoing, the gig companies don’t need to win if they are successful in changing the law underpinning it, either through the legislature or the voter ballot measure.

The gig companies decided to push for the ballot question because of the lawsuit, Yunits told Protocol. And in September, Healey certified two ballot questions put forth by the gig coalition — one that would require additional safety training for drivers, and another that wouldn’t. Voters will likely see only one version of the question on ballots, if it gets to that point.

But the gig coalition doesn’t actually need the question to make it onto the ballot, and it would save them a lot of trouble if it didn’t. Under Massachusetts law, the state legislature can choose to pick up ballot initiatives and decide the outcome for themselves, cutting in front of voters.

The Legislature now has the option of passing the measure directly, proposing a substitute or doing nothing. If they fail to do anything before May, the gig coalition will have until July to collect an additional 13,374 signatures. Only then would the question appear on ballots.

“We continue to push for a legislative solution to this issue and we’re confident that our legislative leaders can get it done,” Yunits said.

Protocol pressed Yunits on this further, asking whether he thought a legislative solution was more likely than the measure going to the ballots. “We remain very confident,” he responded.

The legislative opposition doesn’t share this view. “We anticipate that this will go before the voters this November,” said Massachusetts State Senator Paul R. Feeney. “We're going to be doing everything that we can to make sure that our voters understand the full truth of what companies like Uber and Lyft and DoorDash are trying to do here.”

Within the Statehouse, Feeney senses that the gig companies are preparing for the measure to go to ballots in November, despite their statements to the contrary. “There doesn’t seem to be much engagement in trying to figure out a legislative solution to this,” Feeney said. “We saw in California where they spent an ungodly amount of money to try and buy a law and confuse voters, and I think that’s where we’re heading in Massachusetts.”

In January, the No Campaign also filed a complaint against the ballot measure in Massachusetts Supreme Judicial Court, arguing that it shouldn’t have been certified in the first place.

“Not only do these proposals eliminate otherwise mandated rights, but they also blatantly violate our Constitution,” explained Nicole Decter, General Counsel of the Coalition to Protect Workers’ Rights.

The complaint also alleges that the measure is misleading to voters. It claims that Healey’s petition summary doesn’t adequately explain that drivers should already be classified as employees under Massachusetts state law.

It’s likely that neither campaign will get its best-case scenario: The “Yes” campaign won’t get a legislative victory to bypass ballots, and the “No” campaign won’t block the ballot initiative altogether through its court filing. That means Massachusetts voters will likely get the final say. If that happens, even more money would come flooding into Massachusetts; the debate would leave the cloistered rooms of the Statehouse and enter the frames of millions of smartphones and television screens.

Information warfare

“You hear the same lie four times, it becomes truth.”

That’s what Nicole Moore took away from the California Prop. 22 campaign. Moore is a part-time Lyft driver and organizer for Ride Share Drivers United. From her perspective, California voters were so inundated by the Yes Campaign’s media messaging that they didn’t fully understand what they were voting for.

Exit polls from California showed that 40% of those voting “yes” on Prop. 22 believed they were helping ensure that Uber, Lyft and DoorDash employees could earn a livable wage. But according to a 2019 UC Berkeley study, California gig workers would only really make $5.64 an hour, after accounting for hidden costs such as unpaid wait time and payroll taxes from the “guaranteed” minimum wage of $15.60. (Uber disputed the results, arguing in part that drivers should not be considered “on the clock” when waiting for ride assignments since they retain the agency to accept or reject offers.)

Moore said the gig companies saturated the media market to such an extent that “within a few hours, in your commute home, you’ve heard a couple messages on the radio, you open your Facebook when you get home [and] you get a message or two there, and you turn on the evening news and you get another message.”

The media campaign also directly targeted drivers, who received messaging from Uber and Lyft. The companies warned they would leave California entirely if the measure didn’t pass.

Lyft has once again started claiming that drivers are on its side. “Massachusetts drivers overwhelmingly support the ballot measure by a 7:1 margin because it allows them to keep their independence,” Lyft co-founder John Zimmer said in a November 2021 earnings call.

This kind of media saturation requires wads of cash. By November, the “No” campaign anticipates their opponents will have raised at least $100 million. The target fundraising goal for their own campaign is somewhere around $10 million, of which they’ve already raised about $1 million from a mix of labor and union groups. McEnany said he expects the financial difference to be slightly less important here than it was in California, given that the two groups have only a few major media markets to flood with ads, rather than California’s 14 — four of which are the most notoriously expensive in the country.

Beth Enrique Griffith, one of the members of the “No” coalition’s board, also believes that the money will matter less because the coalition is planning an early grassroots campaign with organizing groups across Massachusetts, a strategy largely absent from the California fight. “We’re going to hit the ground running, starting sooner rather than later, in this campaign,” she said. “We immediately connected with our grassroots organizations around the commonwealth and implemented a strategy and got them involved.”

The “Yes” campaign anticipates that each company will contribute about equally to the fundraising pool eventually, meaning that Uber, DoorDash and Instacart will likely match the record-breaking $14.4 million from Lyft at the very least, if they haven’t already (the campaigns aren’t required to report their donations since 2021 until September of this year). By the end of 2021, the “Yes” coalition had already spent more than $1.7 million just to gather signatures for the ballot proposal, another $600,000 on consulting and more than $100,000 on polling.

Those in-house polls show the ballot measure in a very favorable light. They ask gig workers whether they want to be independent contractors or employees (64% are in favor of being contractors), whether flexibility or full-time employee benefits are more important to them (70% say flexibility) and whether they support or oppose the ballot measure (83% support).

The opposition believes those questions are misleading and ask voters and drivers to believe a false paradigm: The gig companies want people to believe it’s flexibility or benefits, while the opposition thinks it’s possible to have both. But the “No” campaign also doesn’t think it can win when it’s arguing only about those details — instead, they believe they need to convince voters that Uber, Lyft, DoorDash and Instacart are trying to buy a piece of legislation.

Because for the opposition, it’s not only about Massachusetts, but the American way of life: What remains of today’s middle class will become tomorrow’s food couriers, on-demand nurses and uninsured ecommerce warehouse workers.

“We know that if they are successful here in Massachusetts with drivers, that this is only the beginning,” Feeney said. “We’re on the vanguard right now of protecting workers from this tidal wave of gig economy models that will carve out a separate class of workers.”

Massachusetts is set to become a proving ground for future Prop. 22-esque pushes. Opponents of the ballot measure believe Massachusetts will prove to be a tougher test than California for the gig companies, seeing as the commonwealth has a long pro-labor history and a highly engaged voter base. If the companies that depend on gig-worker labor can win in Massachusetts, they’ll be ready to win just about anywhere else.

“Our proposal for a new pragmatic approach is supported by 82% of drivers and 76% of voters,” Uber CEO Dara Khosrowshahi said in a November 2020 earnings call, referencing the passing of Prop. 22 in California. “It's a priority for us to work with governments across the U.S. and the world to make this a reality.”


Microsoft Exchange Online users face a key security deadline Saturday

The company will start disabling a highly vulnerable login option, known as "basic authentication," beginning on Oct. 1 — though customers will have one chance to buy more time to transition off the system.

Microsoft has been seeking to prod businesses to move off basic authentication for the past three years, but "unfortunately usage isn’t yet at zero," it said in a post earlier this month.

Illustration: Christopher T. Fong/Protocol

Microsoft is about to eliminate a method for logging into its Exchange Online email service that is widely considered vulnerable and outdated, but that some businesses still rely upon.

The company has said that as of Oct. 1, it will begin to disable what's known as "basic authentication" for customers that continue to use the system.

Keep Reading Show less
Kyle Alspach

Kyle Alspach ( @KyleAlspach) is a senior reporter at Protocol, focused on cybersecurity. He has covered the tech industry since 2010 for outlets including VentureBeat, CRN and the Boston Globe. He lives in Portland, Oregon, and can be reached at kalspach@protocol.com.

Sponsored Content

Great products are built on strong patents

Experts say robust intellectual property protection is essential to ensure the long-term R&D required to innovate and maintain America's technology leadership.

Every great tech product that you rely on each day, from the smartphone in your pocket to your music streaming service and navigational system in the car, shares one important thing: part of its innovative design is protected by intellectual property (IP) laws.

From 5G to artificial intelligence, IP protection offers a powerful incentive for researchers to create ground-breaking products, and governmental leaders say its protection is an essential part of maintaining US technology leadership. To quote Secretary of Commerce Gina Raimondo: "intellectual property protection is vital for American innovation and entrepreneurship.”

Keep Reading Show less
James Daly
James Daly has a deep knowledge of creating brand voice identity, including understanding various audiences and targeting messaging accordingly. He enjoys commissioning, editing, writing, and business development, particularly in launching new ventures and building passionate audiences. Daly has led teams large and small to multiple awards and quantifiable success through a strategy built on teamwork, passion, fact-checking, intelligence, analytics, and audience growth while meeting budget goals and production deadlines in fast-paced environments. Daly is the Editorial Director of 2030 Media and a contributor at Wired.

Gavin Newsom shows crypto some California love

“A more flexible approach is needed,” Gov. Newsom said in rejecting a bill that would require crypto companies to get a state license.

Strong bipartisan support wasn’t enough to convince Newsom that requiring crypto companies to register with the state’s Department of Financial Protection and Innovation is the smart path for California.

Photo: Jerod Harris/Getty Images for Vox Media

The Digital Financial Assets Law seemed like a legislative slam dunk in California for critics of the crypto industry.

But strong bipartisan support — it passed 71-0 in the state assembly and 31-6 in the Senate — wasn’t enough to convince Gov. Gavin Newsom that requiring crypto companies to register with the state’s Department of Financial Protection and Innovation is the smart path for California.

Keep Reading Show less
Benjamin Pimentel

Benjamin Pimentel ( @benpimentel) covers crypto and fintech from San Francisco. He has reported on many of the biggest tech stories over the past 20 years for the San Francisco Chronicle, Dow Jones MarketWatch and Business Insider, from the dot-com crash, the rise of cloud computing, social networking and AI to the impact of the Great Recession and the COVID crisis on Silicon Valley and beyond. He can be reached at bpimentel@protocol.com or via Google Voice at (925) 307-9342.


Slack’s rallying cry at Dreamforce: No more meetings

It’s not all cartoon bears and therapy pigs — work conferences are a good place to talk about the future of work.

“We want people to be able to work in whatever way works for them with flexible schedules, in meetings and out of meetings,” Slack chief product officer Tamar Yehoshua told Protocol at Dreamforce 2022.

Photo: Marlena Sloss/Bloomberg via Getty Images

Dreamforce is primarily Salesforce’s show. But Slack wasn’t to be left out, especially as the primary connector between Salesforce and the mainstream working world.

The average knowledge worker spends more time using a communication tool like Slack than a CRM like Salesforce, positioning it as the best Salesforce product to concern itself with the future of work. In between meeting a therapy pig and meditating by the Dreamforce waterfall, Protocol sat down with several Slack execs and conference-goers to chat about the shifting future.

Keep Reading Show less
Lizzy Lawrence

Lizzy Lawrence ( @LizzyLaw_) is a reporter at Protocol, covering tools and productivity in the workplace. She's a recent graduate of the University of Michigan, where she studied sociology and international studies. She served as editor in chief of The Michigan Daily, her school's independent newspaper. She's based in D.C., and can be reached at llawrence@protocol.com.

LA is a growing tech hub. But not everyone may fit.

LA has a housing crisis similar to Silicon Valley’s. And single-family-zoning laws are mostly to blame.

As the number of tech companies in the region grows, so does the number of tech workers, whose high salaries put them at an advantage in both LA's renting and buying markets.

Photo: Nat Rubio-Licht/Protocol

LA’s tech scene is on the rise. The number of unicorn companies in Los Angeles is growing, and the city has become the third-largest startup ecosystem nationally behind the Bay Area and New York with more than 4,000 VC-backed startups in industries ranging from aerospace to creators. As the number of tech companies in the region grows, so does the number of tech workers. The city is quickly becoming more and more like Silicon Valley — a new startup and a dozen tech workers on every corner and companies like Google, Netflix, and Twitter setting up offices there.

But with growth comes growing pains. Los Angeles, especially the burgeoning Silicon Beach area — which includes Santa Monica, Venice, and Marina del Rey — shares something in common with its namesake Silicon Valley: a severe lack of housing.

Keep Reading Show less
Nat Rubio-Licht

Nat Rubio-Licht is a Los Angeles-based news writer at Protocol. They graduated from Syracuse University with a degree in newspaper and online journalism in May 2020. Prior to joining the team, they worked at the Los Angeles Business Journal as a technology and aerospace reporter.

Latest Stories