As someone who drove a taxi in Toronto during three summers of my college years, I have long begrudged the success of Uber. One could once make a decent living driving a cab, and my Toronto taxi license was always my insurance policy if I screwed up my career, which was always a formidable fear. I met plenty of drivers in Toronto who owned their own homes, put their kids through school, and took vacations.
Uber disrupted the taxi business, and for a time, its model benefited drivers and consumers. The company offered sweetheart incentives to entice people to use their vehicles and chauffeur others around town, and Uber’s passenger charges were significantly lower than prevailing taxi rates. An additional cost saving was that Uber drivers didn’t initially expect tips.
Fast forward to today, and the only person Uber is truly benefiting is CEO Dara Khosrowshahi, who since 2019 has pulled in a whopping $162.4 million for running a glorified national taxi operation that he neither pioneered nor meaningfully improved.
The brains behind Uber was Travis Kalanik, a savvy tech entrepreneur who by all accounts was a mega a-hole who had little regard for prevailing business norms or practices. Khosrowshahi brought civility, polish, and corporate kumbaya. What he did not bring was a better deal for drivers or riders.
As Khosrowshahi became obscenely richer, Uber drivers increasingly say they have been getting the shaft. Operating costs for gas and insurance have surged. Incentives have dwindled. Algorithms now prioritize shorter, lower-paying rides. Markets are oversaturated with too many drivers chasing too few decent fares. Uber’s shift to “Upfront Fares Plus Destination” pricing has further reduced driver pay per trip. Drivers say they must work longer hours to earn what they once made, and there are growing reports of drivers quitting in droves.
Meanwhile, Uber’s and Lyft’s prices have soared. When I moved to Los Angeles in 2016, I recall taking an Uber from my home to LAX for about $16. A few weeks ago, I took a Lyft to SoFi Stadium, which isn’t far from LAX, and it cost me about $50, even though it was a beautiful Sunday morning and there was no traffic. Typically, Uber and Lyft prices are similar, but my credit card offers meaningful benefits for using Lyft.
In a million years, I never thought I would embrace driverless taxis. I long viewed them not as progress, but as another Silicon Valley attempt to dehumanize everyday life and further reduce personal interaction. I remember a photo in a New York Times story years ago showing the writer riding in a Waymo while texting on her phone and thinking how depressing it looked. I used to enjoy talking to taxi drivers, particularly in San Francisco, where drivers once tended to be an interesting lot who migrated in the 1960s for drugs and rock ’n’ roll.
Some Uber and Lyft drivers have been interesting, but increasingly I have found myself feeling uncomfortable and unsafe. On a recent Lyft ride, the driver was blasting music I found unpleasant and driving more aggressively than I liked. I perceived something menacing about the situation and chose not to ask him to slow down or turn the music down.
My unease may not have been imagined. The New York Times recently published an investigation revealing that Uber has approved drivers with a wide range of criminal convictions, including violent felonies. According to internal data disclosed through litigation, Uber received a report of sexual assault or sexual misconduct in the United States nearly every eight minutes on average from 2017 through 2024, far more than the company has publicly acknowledged.
Perhaps Lyft does a better job screening its drivers. But in my experience, many drivers I have encountered work for both companies, which blurs any meaningful distinction between the two platforms.
A few weeks ago, Cousin Rob asked me to join him on a Waymo ride. I agreed reluctantly. I distrusted the technology and I despise Google, which owns Waymo. But the ride was exceptionally pleasant, and as I talked with Cousin Rob and his friend Alfred, I forgot there was no one driving the car.
Cousin Rob soon began using Waymo regularly, and when we went out to dinner recently, he summoned one. As someone who enjoys music, Cousin Rob appreciates Waymo’s feature that allows him to sync tunes from his iPhone. I had some fun testing Waymo’s customer support.
I activated the support function and suddenly found myself speaking with a cheerful young woman over the car’s speakers. She likely found it odd that I was simply confirming I could talk to a real person if needed, but she was gracious and assured me that help was always available. That said, Waymo customer support does not include conversation for people who might be feeling a tad lonely.
Tellingly, the woman was well trained not to volunteer much information. She would not say where she was located.
Over the past few days, I have needed transportation because my car was in the shop, and I opted to take Waymo because I had grown to prefer the service. Waymo typically charges less for rides than Uber and Lyft in Los Angeles, and when you factor in that no tipping is required, the savings can be meaningful.
Admittedly, using Waymo requires abandoning some long-standing habits. While waiting for my Waymo to arrive at my dealer, I spotted the vehicle down the street and began waving incessantly to catch its attention. I suspect I am not the first person to do that.
There was also an issue with the route my Waymo took, which did not seem the most direct. I instinctively asked the vehicle why it was turning left, before quickly realizing the foolishness of asking the question.
Another adjustment is that Waymos drive like many elderly drivers: extremely cautious, never exceeding the speed limit, and never rolling through stop signs. That is a plus for safety reasons, though if you are running late, the slowness can become frustrating.
Waymo’s obsessive focus on safety is why the company remains in business. Cruise, which was owned by General Motors, was once a formidable competitor in San Francisco but ran roughshod over regulators, who eventually forced GM to halt the service.
Cruise even managed to alienate San Francisco residents, among the most tech-savvy in the nation. There were repeated instances of residents disabling Cruise vehicles by placing traffic cones on them. Management was under enormous pressure to move fast and cut corners, especially as GM CEO Mary Barra, who chaired Cruise’s board, was regaling Wall Street with claims that Cruise would generate $50 billion in annual revenue by 2030.
Despite those lofty promises, Barra abruptly shuttered Cruise in late 2024.
By contrast, Google still treats Waymo as one of its so-called “moonshot” projects, and CEO Sundar Pichai has wisely avoided making grandiose predictions about its revenue potential. He does not need to.
Waymo was recently seeking a valuation north of $100 billion, impressive for a company operating in only a handful of cities. It is now testing service in Detroit to master winter driving conditions before expanding further. When it does, Waymo will be seen as something far more consequential than Mary Barra’s much-hyped EV “North Star.”
“Waymo’s in a multitrillion-dollar global market and as far as I can tell, there are no competitors that are close,” Vinod Khosla, a billionaire Silicon Valley investor, told Forbes. He said it could be “bigger than Google’s ad business,” and argued Alphabet should spend “tens of billions of dollars a year” to expand coverage and lock in market share.
It is precisely because of Waymo’s demonstrated caution that I trust the company and its vehicles. Elon Musk hopes to make Tesla a formidable competitor, but he has not demonstrated the slow, disciplined maturity of Waymo’s management. I am far from ready to experience Tesla’s driverless service. Admittedly, I would not support any business owned or controlled by Musk.
Rest assured, I am not naïve. I fully expect Waymo, and perhaps a small number of other companies, to eventually blow Uber and Lyft out of the water, only to jack up prices once competition disappears. That is how these tech disruption stories typically play out.
Unless Uber can offer reliable driverless rides within a few years, I would be surprised if the company survives having its own business disrupted by another tech disrupter.
That outcome would, of course, derail Dara Khosrowshahi’s nine-figure meal ticket.
It could not happen to a more deserving empty suit.