This SoftBank-Backed Startup Sought to Disrupt the Car Market. Instead, It Became a Poster Child for Disruption Gone Awry

We’ve come to “liberate” the employees from “prison” of Ford Motor Co., Scott Painter declared to the room.

It was July 2019, and Painter was speaking at the first all-hands meeting after his car-leasing startup Fair had agreed to acquire competitor Canvas from Ford. Painter at times came off as a great salesman—and at times preaching to the choir, according to attendees who spoke with Fortune.

He rambled on about subscription car services to a room full of employees, many of whom had spent much of their careers working in the sector, dragging the scheduled one-hour meeting into roughly two and discomfiting many in the crowd by likening Ford to a prisoner-of-war camp. Painter was joined at the meeting by his brother Tyler, who served as Fair’s CFO, and Lisa Russell, an associate who served as the company’s executive vice president of people and culture.

By the time Painter finished, the catered spread of tacos was stone cold. And positive sentiment seemed to have cooled too—not just toward Painter but toward Fair as well, some of those attendees later said.

When it launched in 2017, Fair was marketed as a potential game changer for car ownership and rentals in the age of the sharing economy. The pitch: No longer would consumers be buried under a complex process of haggling with dealerships and making sense of fine print, registration details, and insurance contracts. Instead, renters could choose a car with little more than a few taps on their phone. Fair would buy the car and lease it out to consumers on a monthly basis. It sounded like a great deal for commitment-phobic customers—if they wanted to turn in their car for another model or no car at all the next month, all it took was a few more taps. It was also a cash-burn intensive business. Fair owned the vehicle and would be responsible for finding a customer to take over the contract.

Employees of TrueCar celebrated while ringing the opening bell for the Nasdaq Exchange in Times Square on May 16, 2014, in New York City.
Andrew Burton—Getty Images

“It’s clear that technology is transforming how we buy and own our cars, and the consumer is the winner—with simpler, more flexible, and more cost-effective options than ever before,” Painter said in a 2017 news release announcing nearly $1 billion in capital raised from investors. “Fair is on the forefront of making personal mobility more accessible for a new generation of customers.”

His reputation for being a good salesman was not unwarranted. Painter had a track record and a kind of enthusiasm that investors gravitated toward, particularly at a time when mega venture rounds were chasing the next big thing. SoftBank had invested in Fair’s Series A round, but by late 2018 the Japanese investor led its $385 million Series B. Overall, Fair raised more than $2 billion in equity and debt, according to Crunchbase, valuing the business at $1.2 billion, and putting Painter just where every Silicon Valley founder wanted to be: at the helm of a unicorn, backed by the deepest pockets around.

Fast-forward to the end of 2019, the picture looks quite different. Fair has laid off 40% of its workforce. It is the subject of audits by backer SoftBank. Once rapidly scaling up its fleet, it is now in the process of selling off cars, and Painter has stepped down as CEO. There’s no longer talk of hypergrowth as the company instead seeks to navigate the uncertain road ahead.

What went wrong? Interviews with 29 current and former employees, who spoke with Fortune on the condition of anonymity for fear of violating nondisclosure agreements, paint a picture of a company in which controls were few, chaotic record-keeping meant basic business functions were run in an unprofessional way, and a “bro” culture was allowed to flourish. Fortune gave both Fair and Painter the opportunity to address the allegations made in this story, but both declined to comment.

Indeed, the story of Fair encompasses themes that will be familiar to many startups that launched this decade. It is a cautionary tale of what happens inside a company when you combine a charismatic founder, more funding than a company knows what to do with, a mandate for hypergrowth, and the true-believer syndrome that your startup is destined to change the world.

Now, as cooler heads prevail, a startup that existed to break all the rules is trying to figure out how to play by them to survive.

Hypergrowth at all costs

Fair was actually at least one of a dozen automotive startups founded by serial entrepreneur Painter—all focused on injecting technology into the car-buying and ownership experience. The 51-year-old attended West Point, where he studied political science and systems engineering. From 1987 to 1991, he also served as a Spanish-speaking interrogator in the U.S. Army, according to his LinkedIn profile. Painter transferred in 1991 to the University of California at Berkeley, where he studied economics but left before graduation to launch AUTOAccess, an electronic database of used cars.

Cars Direct, a company that introduced upfront pricing to auto retail, was one of his early ventures (he also detoured from cars, into dentistry, serving as the VP of marketing for 1-800-DENTIST). Then came his next startup, TrueCar, which aimed to eliminate the negotiating process from car-buying by opening up access to pricing data from a network of TrueCar certified dealers. Though he saw TrueCar to a successful IPO in 2014, the venture led to a tumultuous relationship with dealerships—contributing in part to his resignation in 2015, when, as he told shareholders, it was “time for a change.” A few months later he launched Fair along with Georg Bauer, former head of financial services for Tesla and BMW AG.

Though Fair grew quickly and attracted millions in early venture funding, the drive for growth meant an incredibly high burn rate. The company was expanding rapidly into new markets such as Nashville, Chicago, and San Francisco—betting on its ability to gain market share by underpricing its competitors. Another sign of the company’s ability to attract talent: It also announced the addition of a chief strategy officer from Tesla—Diarmuid O’Connell—with much fanfare in 2018. But there was also turmoil. COO & CFO Fedor Artiles—also a former Tesla executive—left in June 2018 officially to raise his family in Europe—but employees noted he had often butted heads with Painter. After a few months, Scott’s brother Tyler took over as CFO. O’Connell had also quietly disappeared. By the final months of 2018, employees recall Painter worrying that Fair was “coming close to the rocks”—running low on cash, and even in arrears on payments to some vendors.

But Painter had an idea. Fair already had a relationship with one of the biggest SoftBank-backed companies of them all: Uber. Fair had acquired the ride-sharing giant’s car leasing business, Xchange Leasing, in early 2018. SoftBank had participated in Fair’s Series A round. Now, as Fair’s coffers began to run dry, SoftBank came through in a big way, ponying up $385 million in Series B funding at a time when Uber was cleaning up for its own IPO.

Encouraged by SoftBank, Fair leaned even more heavily on the partnership with Uber, beginning an ambitious project internally known as “Shasta” in late 2018, according to former employees who spoke with Fortune. Previously, Fair would acquire cars for customers and usually allow them to pick up at dealerships. Under Shasta (also known as “Fair Go,”) Fair would buy cars in bulk, use its own lots to house the cars, and push the product to ride-sharing drivers who might want to rent on a weekly basis. Painter early on set a goal to acquire 20,000 vehicles for the project, sources say.

Fair now had plenty of money to do this, thanks in part to SoftBank and the company’s multiple lines of credit from the likes of Japanese bank Mizuho and Credit Suisse. But cars weren’t the only thing the company began to spend heavily on. As part of the project, the company rented an Airbnb house in Malibu for a team of engineers—stocked with catered foods and masseuses—so engineers could work around the clock on Fair Go.

It was consistent with the “bro” culture that employees said grew inside the walls of the company’s Santa Monica office. In one coding exercise created to help engineers familiarize themselves with Fair’s tech infrastructure, a manager asked employees to determine the youngest woman they could date based on the engineer’s age. If the engineer’s age was too high, a digital message would pop up that read: “You remind me of my daddy,” employees recall. The eventual answer: half your age plus seven. While it was a joke derived from the hit TV series How I Met Your Mother, it didn’t diminish the insensitivity of the exercise, according to three employees who were present.

After complaints from employees, the company removed the exercise.

Employees recall that Painter was also given to cursing and relied heavily on sailing-related references in all-hands Fair meetings. It was also a stressful time personally. Painter was known to be going through a divorce, and the father of four was also rebuilding his burned down Bel Air home, employees say.

For many, it was the beginning of an exhausting expansion. Fair was dedicating significant resources to Shasta, even while receiving a steady number of complaints on Facebook about basic issues, such as logging in to the app. Fair flew in employees from around the country to stay in the city for weeks on end, maxing out their company credit cards, employees said. 

There was one big problem as Fair tried to get Shasta off the ground. Fair was having difficulty keeping track of the available cars it had or where they were, employees said. While aggressively ramping up the Uber partnership, the company had neglected to build out a uniform fleet management platform system. Instead, dozens of checklist items including a car’s identity, location, condition, and availability were managed off Google spreadsheets—over and over again for thousands of cars across multiple locations. Some cars were found in impound lots and salvage yards, former employees say.

 It was “a mess,” former employees say, manually documenting the company’s Shasta vehicles—a fleet that numbered some 14,000 cars—by copying information from spreadsheet to spreadsheet.

Even so, Painter was focused on raising more money, talking up the fact that he planned to raise another $1 billion in the fall of 2019 to fuel further growth, employees say.

Painter’s confidence was not unfounded. Typically, venture investors test if a startup has what it takes to make it big by placing smaller amounts into early-stage companies in their Series A or B rounds. In 2018, for instance, companies backed by prominent venture capitalists focused on tech raised about an average $30.7 million in a Series B round, according to an analysis by venture capital firm Wing.

But SoftBank, in particular, was known for going big. It sought huge potential winners that promised a lengthy time horizon. Other SoftBank portfolio companies such as WeWork, Lemonade, and Katerra had seen the Japanese investor lead round after round of eye-popping fundings even in the early stages. Fair would be no exception: SoftBank sank more than $300 million—10 times the average—into Fair’s Series B.

Back at headquarters, Fair was burning through cash at a terrific pace. In theory, the company would acquire capital-heavy cars through its lines of credit from the likes of one of its banks, such as Mizuho. But since the credit lines often came with restrictions—for example, requiring a customer name tied to the vehicle—Fair was at times acquiring cars with cash, per sources.

To compound the problem, the Shasta waitlist was booming in its early markets. Fair poured millions upon millions into new cars in a bid to match demand, even while it had a fleet of empty cars spread around the country in the dark, former employees say.

In Fair’s mission to get as many cars out to as many consumers as possible, it had not implemented the strong identity-check software that other car rental companies used, and also accepted prepaid credit cards that allowed consumers to make the initial payment and skip out on the rest, sources say. Hertz, by comparison, typically accepts only major credit cards.

In the end, the identity check woes brought up further complications in tracking down individuals for repossession of cars or collection of fees, employees said. Delinquencies and repossessions became a concern. Suddenly, even creditors were pushing to see collection and repossession rates from Fair, former employees said.

But problems persisted. In one instance, Fair was missing a notable number of cars in the Chicago area thanks to fraud, two former employees close to the matter said. Those mostly higher-end cars such as Land Rovers worth over $30,000 each would occasionally pop up in other ride-sharing programs or crime scenes.

As the summer wore on, Fair tried to resolve the most egregious issues. The company told employees that it was using a fleet management system known as Fleetio that now knew where over 97% of its Shasta cars were located.

There was a pattern of chasing the next big project—creating new fires before old ones could be extinguished, former employees say. For example, in early 2019, Fair decided to spend millions on a vehicle restoration facility planned for an old Walmart location around Oakland. The idea was to quickly fix up vehicles in need of repair rather than to lose them for weeks at an external shop. That project has since been paused, a source said. 

And even in the higher echelons of the company, the picture was less than perfect. In April 2019, after spending just over a year with the company, former Googler and chief product officer Dylan Casey left the company. Upper management, former employees say, was filled with big personalities.

The end of an era

But the real shock came in October. That’s when Softbank’s huge bet on a WeWork’s IPO came crashing down, and at a time when the Japanese giant was in the process of raising a massive Vision Fund II. That same month, SoftBank dispatched a fleet of auditors to act as an in-house cleanup crew as several of its other investments also came under scrutiny. And Fair was beginning to run low on cash.

Soon after the review began, Painter addressed his staff at a “Fair Family” all-hands at its Santa Monica headquarters. Fair needed to become profitable and stop overpaying for vehicles, he told the crowd while trying to keep the group optimistic. Still, he appeared tired and threw in a larger number of f-bombs than usual, saying that the company would grow and shrink as needed. To some, it appeared he was suggesting that if they didn’t believe in the Fair vision anymore, they could leave, employees say.  

Thus began a new chapter at the startup. Hypergrowth was replaced by shrinkage. SoftBank had agreed to offer a $25 million bridge loan in return for major changes at Fair, sources say. That meant those same layoffs and a more focused business plan.

On Oct. 25, management decided to cut staff by 40%. Then came another shock: On October 30, Painter would be stepping down.

Later, among other initiatives, the company began selling off cars, in part to manage its cash crunch. Fair also “temporarily curtailed” its existing business in Dealertrack, an on-demand software company for dealers, and RouteOne, a vehicle financing portal. The decision was made “so we can dedicate our full attention to evaluating our future model and processes,” Georg Bauer, cofounder and vice chairman, wrote in a Nov. 14 note to its dealer partners seen by Fortune. “We ask you to bear with us over the coming days and weeks as we continue to reshape our business focus,” Bauer added.

What’s next for Fair

One week after stepping down as CEO, Painter showed up at Web Summit, an annual tech conference with more than 70,000 attendees in Lisbon, where he was scheduled to speak on a panel, moderated by a Fortune reporter, called “No Downside to the Sharing Economy.”

In the days before Web Summit, it wasn’t clear if Painter would show up. He didn’t respond to an email planning thread, and Web Summit organizers said they hadn’t heard from him. It wasn’t until November 5, the day before the panel, that Painter’s assistant replied and said he would be there.

In person, Painter was quick to spin the news of his resignation as a positive for the company, heaping praise on SoftBank and reiterating that the company isn’t another WeWork.

“Everyone wants to write about SoftBank right now,” Painter told Fortune at Web Summit. He added that what’s happening at Fair “really isn’t as exciting” as it is being made out to be in the media. 

“We are a victim of our own success,” Painter said. Several times, he mentioned that Fair had 65,000 customers in the past year.

“That’s 65,000 cars!” he said. “That’s more than a lot!”

Painter was joined backstage by Sam Zaid, CEO of Getaround, a car-sharing platform that is another SoftBank-backed company, and who was also appearing on the panel. The two were friendly and said they had known each other for a while. Painter told Zaid he had been busy with meetings in Saudi Arabia the week before Web Summit.

Onstage, Painter maintained his optimism about Fair’s prospects and painted a picture of a company that wasn’t in disarray but was instead addressing its growing pains. Growth is messy, he said. And what Fair is experiencing is simply what happens when you’re trying to build a business.

“It is pretty clear that in today’s environment, you have to be focused on sustainable growth,” he said. “For us, we started growing so fast in support of our ride-share and consumer business that we started to grow folks in parts of the business that we really didn’t intend to in the first place.”

After the layoffs, Fair plans to pivot away from “people intensive” areas. Many of the job cuts would be addressed by automating certain processes, Painter said.

Still, he remained ever the salesman. He used the opportunity to pitch Fair to an audience of people from around the world, perhaps future customers, touting how the company could allow people access to a car without having to go into debt.

For good measure, he said, the plan is to grow the personal driver business “three to four times” over the next 12 to 18 months.

“We are entering a new phase of our growth,” he said.

SoftBank and Fair are now considering what parts of the business to cut, sources say, with SoftBank actively overseeing the investment. A Nov. 7 note from the car startup’s interim CEO Adam Hieber detailed that the executive had been through “countless” brainstorm sessions in the office as it seeks a path to sustainable growth. Specifically, Fair expects to focus on relaunching its consumer subscription product and “sharpening” its ride-sharing side of the business.

SoftBank and its founder, Masayoshi Son, were looking 300 years into the future, according to a 2010 slide pitch to investors. But they failed to appreciate the scrutiny investors would place on these unicorns as they marched toward IPOs.

Indeed, as one decade ends and another begins, the landscape looks very different. Profits are in; so is governance. “Visionary” founders maybe aren’t quite as venerated as they once were. And, as one company learned, building an idea into a company can be a bumpy road that isn’t always, one could say, Fair.

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