Lyft Inc. has always played the nice guy. It branded itself with a friendly pink mustache in the early days, and encouraged riders to fist bump their drivers. It let people tip inside its application for years before Uber finally relented. And even as it’s grown, it’s retained a big brand advantage over its rival, particularly because of Uber’s various toxic-culture-fueled crises in 2017. But as Lyft prepares for an initial public offering, a few cracks are beginning to show in its nice guy image. A New York Times profile this week of Lyft’s chief executive officer, Logan Green, made the point that the other executives Green most admires (one of whom was Elon Musk) aren’t so nice at all. Can Lyft have it both ways—winning over customers with a positive reputation, while also convincing investors it has the gumption to build a breakout tech company? In a statement, the company’s chief operating officer called Green and his co-founder “cutthroat missionaries in service of creating positive change.” That’s an odd mashup. Lyft may get a chance to show Wall Street its ruthless side soon enough. In that crucible of markets New York City, officials have long frustrated ride-sharing companies with regulations. Historically, Uber has been the star of the show, but this time around it’s Lyft that’s stirring controversy. The startup, along with smaller ride-hailing company Juno, sued the city’s Taxi and Limousine Commission over new rules governing driver pay. With the lawsuit Lyft is challenging new regulations, slated to go into effect Friday, that are meant to increase drivers’ earnings to at least $17.22 an hour. The details of the legal fight are complicated, but essentially Lyft and Juno say that the commission’s rules favor Uber by rewarding companies that are able to keep drivers busiest. Lyft has said it’s fine with a minimum wage in theory—but says it would wind up paying more for drivers’ time than competitors. Uber, for its part, has said it’s going to try to pass the wage hike off to customers by raising prices. Regardless of the merits, the fight hasn’t put Lyft in a good light. New York Mayor Bill de Blasio lampooned the lawsuits in a tweet: “Unconscionable. The overwhelming majority of these companies’ drivers earn less than minimum wage. We won’t stand for it in New York City, and we’ll fight every step of the way to get workers the pay they deserve.” Lyft’s case highlights two uncomfortable facts for the company. For one, there are real business model disadvantages to being the smaller player. Uber doesn’t just have more riders and drivers; it’s able to connect them more quickly and efficiently. That’s good for Uber’s business and bad for Lyft. That gap will surely play into how public market investors value the two companies. Second, as Uber has embarked on an international charm offensive, Lyft may wind up looking like the bad guy more often. Being the underdog is tough, and Lyft has done a good job in the past few years of taking advantage of Uber’s fumbles. But this year it may prove more difficult than ever to keep up the fight and still retain its patina of friendliness. Green’s challenge will require delicate diplomacy—hopefully he won’t take too many cues from Elon Musk.


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