Updated February 19, 2022 at 6:28 PM ET
In 2010, Australian entrepreneur Domm Holland had an idea: he was going to punk the country's largest airline.
He had bought the domain Qant.as for just $20 and practically waved it in the face of Qantas Airways.
"The domain name Qant.as could be snapped up by a competitor so damage to Qantas's business could be in the millions of dollars," Holland told the Australian at the time.
To apply even more pressure, Holland redirected Qant.as' web traffic to Virgin Blue, a rival airline.
He eventually claimed he had sold the domain for $1.3 million, but refused to identify the buyer.
Records show that it is now registered to Qantas Airways Limited. The site is currently inactive. The airline did not return a request for comment.
It's an early career example of something Holland would become known for in Australia: pushing boundaries to command attention and make a buck.
Now he's exported that brash style to the U.S., where venture capitalists have lapped it up. They have lined up in droves, pouring millions into Fast, Holland's San Francisco startup that offers one-click checkout and password storage, a competitive corner of e-commerce where a handful of upstarts are attempting to challenge the might of Apple, Google and Amazon.
Some in Australia say the way he has reinvented his image is a deliberate escape from his past and an insult to those harmed by his past business.
With a new image, aiming to be a 'unicorn'
In some ways, Holland fits the stereotype of a flashy tech executive who relishes thrills and wears the capitalist rebel badge on his sleeve.
He skydives and boasts about his sports boat on Instagram. Last fall, he started a press conference in Tampa, Fla., where his family now lives, by getting into a NASCAR truck and spinning out in donuts before exiting through the window to applause and loud cheers as a handler slipped a salmon-colored blazer on him. He calls himself "the world's fastest CEO."
Tampa is now the @fast-est city pic.twitter.com/27nJi32p4W
— domm (@domm) August 5, 2021
People who know Holland say he has the gift of gab and can easily get people energized about his ideas.
Stripe, which helps businesses process credit card payments, is one of the most valuable startups in the world. Its venture capital arm is influential and seen as a kind of kingmaker in Silicon Valley. Last year, it announced with venture capital firm Addition a $102 million funding round for Fast. Analytics firm PitchBook pegs the company's valuation at $584 million. But internal Fast documents reviewed by NPR show that the company's most conservative estimate to new hires is that it will eventually be worth about $1 billion, also known as 'unicorn' status. According to the document, company officials say Fast could one day be valued at $12 billion.
Who wants to skydive with @domm? pic.twitter.com/cFmIqgyB4s
— Fast (@fast) April 4, 2021
Back in Holland's home country, though, some cannot believe their eyes.
As some Australians see it, Holland moved to the U.S. to refashion his identity and move beyond the controversial legacy of his last business.
While failure and reinvention are embraced in Silicon Valley, the way Holland has rewritten and polished his past raises questions about how far the envelope can be pushed before crossing ethical lines.
Ilya Strebulaev, a professor of finance who studies the venture capital industry at Stanford University, noted that more than 80% of startups fail, so past stumbles alone have never been counted against a founder. But, he said, the details matter.
"Failure is not a curse," Strebulaev said. "But what's important is how the failure happened."
Over the course of three weeks, NPR asked repeatedly for an interview with Holland and for on-the-record responses to questions about his past and Fast's business. All were denied. On Tuesday, Fast Chief Communications Officer Jason Alderman sent NPR a minute-long audio recording of a prepared statement.
Australian tow-truck owner: 'There's a lot of people he ripped off'
Joe Andriske is quick to offer his assessment of how Holland's last business failed.
"It was a disaster," Andriske said.
Andriske runs Harvey's Towing Services in the Australian state of Queensland, a region in the northeastern part of the country that contains the major metropolitan area of Brisbane and the Gold Coast's more than 40 miles of coastline popular with surfers and tourists.
Holland's former startup Tow.com.au aimed to be "the Uber of towing" there by providing a quick way to call a towing contractor like Andriske when a vehicle had to be impounded for violating what Australia calls "anti-hoon" laws, or laws against reckless driving.
Tow won an exclusive contract with the Queensland police and was involved in the towing of some 100 vehicles a day when business was really humming, according to a former employee of the company.
Holland acknowledges his experience with the towing startup on his social media accounts and on Fast's website. On the latter, it says he founded "an on-demand vehicle towing platform in Australia that processed more than $50M in transactions," before highlighting his business awards for the startup, including winning the Brisbane Young Entrepreneur of the Year.
"He definitely left some stuff out," Andriske said.
Namely, Andriske notes, a multimillion-dollar billing dispute with the Australian state government over towing and impounding fees that led to the startup's liquidation in 2018.
Many cars that were towed were not worth much, so owners never showed up to repossess them, which created a massive unpaid bill to the tow companies. Holland said the government should pay, while the government countered that it was Holland's responsibility.
A legal fight ensued when Holland sued the government, accusing Australian officials of "the nation's most horrific case of wage theft," according to a text message he sent to his former employees reviewed by NPR.
Eventually the mounting unsettled towing and impounding fees drained the company's coffers and sent it on the brink of bankruptcy.
When Holland was running out of cash, he told the Australian Broadcasting Corporation he had planned to sell the personal data, like bank accounts and drivers' licenses, of more than 21,000 people obtained through his towing app.
"A driver's license detail on the black market is worth $80 and we're talking tens of thousands of these types of records," Holland told the ABC. "It is hugely valuable information for people looking to obtain that kind of detail."
Government officials rushed to court to enjoin Holland from doing so, and the country's Supreme Court forced him to surrender the sensitive trove of data, an order that carried the risk of arrest if violated.
"That action really typified the way he's willing to fight. He's willing to really bend the rules of what's acceptable and sometimes ethically and morally," said ABC Reporter Kristian Silva, who covered the downfall of Tow, which was based in Brisbane. "When he's backed up into a corner, he'll pull out any tactic he can to win."
Some locals, he said, viewed Holland's move to the U.S. as a way of running from his past. Silva said longtime observers of Holland noticed that in interviews about his new company Fast, he started going by "Domm," rather than "Dominic," which is how he would typically address himself to Australian journalists. Holland tweets under the handle @Domm, and he now can be seen in publicity photos sporting a T-shirt that says "Domm."
Interviews with half a dozen people in Australia who were once close to Holland indicate that some friends had long called him "Domm," and that nicknames are common in Australia. Several of them, however, did think that professionally, there seemed to be a shift in how he identified himself.
A search of news articles in the database Lexis Nexis shows that his first use of "Domm Holland" in the media was in March 2020, just as the payment-processing company Stripe announced its initial $20 million investment in Fast.
"There was a sense that he was trying to bury what had happened in Brisbane and start afresh," Silva said.
Alderman, the Fast spokesman, strongly disputes that Holland has ever tried to conceal any part of his history with Tow.
The Australian state government settled Tow's legal dispute for less than $1 million in September 2019, as Holland began winding down the company.
An Australian liquidator that prepared a report on Tow.com.au confirmed that, in the end, it owed $5.7 million Australian dollars (or about $4.1 million in U.S. dollars) to mostly small towing businesses.
Andriske was one of them. He received a fraction of the amount he says he was due. His lawyer wrote to Holland's company in March 2018 stating that Harvey's Towing was still owed $594,477.39 in Australian dollars (or about $423,000 in U.S. dollars), according to a document reviewed by NPR.
"He made a promise, made a promise. We get a small payment then he disappeared, mate," Andriske said in an interview, referring to his correspondence with Holland after Andriske said he stopped getting paid. "He then jumped on a plane and he's flying to America."
Andriske decided not to sue Holland. He tried to move on. Yet, he said, seeing Holland's publicity stunts and his startup's soaring valuation rankles him and other small business owners that never got paid.
"There's a lot of people he ripped off. They want their money. I know I want my money," Andriske said. "So if he's got several million over there, how about he sends a bit back over here?" he said.
While the liquidation process does not hold Holland personally responsible for the millions the company owed, Andriske says the right thing to do would be to make him and others in his situation whole.
Alderman, the Fast spokesman, claims Holland tried to do that.
"Unfortunately, Tow was caught in the middle between independent towing contractors who were legitimately owed money and the Queensland state police, Tow's largest client who refused to pay their debts," Alderman said in the recorded statement. "Of course, this is not the result any CEO wants for their employees, partners or their company. Domm fought hard to get every dollar possible to make the tow-truck drivers whole."
Alderman said the Tow saga was revealed to investors at every round of the company's fundraising.
"Domm embraces Tow as part of his journey," Alderman said. "It has made him a better CEO and Fast is a stronger company as a result."
Two venture capitalists who backed Fast told NPR they knew how Holland's towing startup dissolved, but did not see it as a red flag. Other VCs unconnected to Fast had mixed reactions. Some said the Australian saga should not be disqualifying while one, a prominent investor, said Holland's history would dissuade them from doing business with him.
Eric Ries, who has been in the startup world and has written about it for decades, said investors can learn quite a bit from how a founder's previous startup tanked.
"Silicon Valley has long been the home of second — and even third — chances," Ries said. "But it's really important to hold to high standards of honesty and integrity. People tend to respond to the next big thing without seeing why the previous big things failed."
Fast has 'utterly irrational' growth expectations, says former worker
Like all founders, Holland likes to talk about the aha moment that launched his current company Fast: When his wife's grandmother couldn't remember her password to order groceries online.
"This is such a preposterous situation that still exists today," Holland said in an early video about Fast. "Out of frustration, I built a prototype of password-less authentication."
So in March 2019, he founded Fast, a service that is supposed to follow you around the Internet, remembering your passwords to make buying things easier, or as Nicolas Carteron, a reviewer of Fast's pitch deck to investors put it, "make buyers forget they are even buying/paying for something."
Companies like PayPal, Apple, Bolt and Shopify offer similar services, but Holland argues Fast can do it more quickly and seamlessly than others. Holland likes to say that Fast is trying to give the rest of the Internet what is already offered by Amazon, a one-click checkout pioneer whose patent on one-click checkout expired about five years ago.
"Amazon is really quite a great service, at least here in the U.S. Outside of Amazon, that's just not true, so we really want to be able to let businesses compete with Amazon and offer that same delightful consumer experience to their customers outside of Amazon," said Holland on the podcast This Week in Startups.
NPR talked to six former Fast employees about its business challenges, the workplace and Holland. Some pointed to the struggles the startup is facing in bringing customers fully on board with one-click checkout.
NPR used the analytics tool BuiltWith to view more than 1,000 websites that include Fast's technology in their websites code. Out of a random sampling of 50 of the e-commerce sites, 19 never presented the option of Fast's one-click checkout. Former Fast engineers and sales representatives told NPR that integrating the tool on merchant sites has been a challenge, with some sellers reporting that it did not always function properly. But when it does work, and if a merchant lets the tool appear on a product page, buying something is indeed fast and easy.
Other Fast employees describe a workplace culture not unusual for a Silicon Valley startup: Growth and sales goals constantly shifting and sometimes completely unfeasible, or "utterly irrational," as one former employee put it. Workers felt like they were sidelined for trying to align quotas with reality. When issues were raised about data and security practices, these employees said the company was slow to respond. And at the center of it a bombastic founder whose penchant for hijinks did not impress everyone at the company of some 400 people.
"The one time a week we heard from the executive team, Domm was often not there because he was skydiving," said one ex-Fast employee who, like the five others who talked to NPR, requested anonymity for fear of retaliation. "I always thought that was a great metaphor for how the entire company was managed."
Another former Fast worker said Holland seemed more interested in slickly-produced commercials featuring people snowboarding and surfing than anything else.
"They've been able to spin up an image around this company that has nothing to do with payments whatsoever," this person said. "It's just branding and optics."
Nigerian engineers say they weren't credited for early work
Three ex-employees also pointed to something else that caused a debate inside the company: Holland's use of engineers in Nigeria.
In Fast's early stage, it contracted with about a dozen experienced Nigerian software engineers to build out a prototype of the company's product. Holland offered the developers $800 a month, or about $5 an hour, to work full time on designing and building the company's website, mobile app and features, according to a 2019 email Holland sent to engineers in Nigeria that was reviewed by NPR.
Contracting foreign labor to keep costs down is not uncommon for startups. Still, the way Holland handled the relationship raised eyebrows among Fast employees.
Fast has claimed it paid market-rate wages to the engineers in Nigeria, but two engineers in Lagos countered that the rate is lower than what many other U.S. tech companies pay. They said Nigerian tech companies pay about $1,000 a month to entry-level developers, but that this work demanded more advanced skills.
Fast sent the contractors in Nigeria company swag, like Fast T-shirts. A photo from 2019 shows about two dozen mostly young men in Nigeria, wearing Fast gear, posing for a photo. An engineer in Lagos said Holland asked those who took Fast contracts to attend conferences in the country and to spread the word about the company – until they were abruptly let go.
One of the Nigerian engineers said three months into his contract, he tried to log into Fast's Slack, a workplace communication service, and his credentials did not work.
"We just got kicked out with no notice. Slack stopped working. Domm stopped replying. It was really weird," the developer said.
But the biggest insult, according to the developers, who requested anonymity for fear of retaliation, was that Holland never credited them for their work. Instead, Holland, a self-taught engineer, told investors he had built the prototype himself.
A venture capitalist who once worked with Holland defended him, saying trying to acknowledge every developer in pitch meetings would be cumbersome and interfere with how a founder tells a story about a product.
Still, the software engineers in Nigeria who worked on Fast say they still can't shake the feeling that they were exploited.
"He fired everyone from Nigeria. He completely erased us even though we built the first version of the app he was demo-ing to VCs," one of the developers said. "A lot of people were really, really pained. It's like we never existed, but we didn't want to speak up, because we didn't want to develop a bad name in Silicon Valley."
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