- Brian Kelly is the founder and CEO of The Points Guy, a travel and credit-card-rewards website also known as TPG.
- Kelly lives a lavish lifestyle of first-class flights and luxury hotel suites in destinations including the Maldives, Venice, and Japan.
- Some former and current TPG employees described a workplace atmosphere they saw as toxic, including allegations of verbal abuse and public shaming by Kelly.
- Two former freelancers each said Kelly asked them to buy cocaine for him while on a work trip in Asia.
- One of those freelancers, a producer, alleged Kelly made an unwanted sexual advance during a work trip to Costa Rica in 2016.
- In a statement to Business Insider, TPG’s parent company, Red Ventures, said Kelly “unequivocally denies all allegations of drug use, sexual harassment and assault.”
- Visit Business Insider’s homepage for more stories.
This past holiday season was a busy one for Brian Kelly.
First, he hopped aboard a first-class flight from New York to Abu Dhabi, United Arab Emirates, in a private cabin with butler service and its own bathroom. Then came a stay at a $3,000-a-night five-star resort in the Maldives, replete with sunrise yoga and Champagne, before moving on to a luxury resort in Jaipur, India, for Christmas.
It may sound extravagant, but for Kelly, the founder of The Points Guy, it’s just another week on the job.
The Points Guy, a travel and credit-card-rewards website also known as TPG, was founded 10 years ago. Since then, it has grown from a one-man blog into a company with more than 100 employees who bring in 10 million monthly unique visitors to the site.
Last year, according to sources, the site generated more than $50 million in profit. It rakes in affiliate fees by getting readers to sign up for credit cards or reward programs.
To many, working at TPG seemed like a dream job where they were promised a slice of Kelly’s jet-setting lifestyle, which he broadcasts daily to his 232,000 followers. Photos of him cavorting at $2,000-a-night-plus hotels in Venice and the Caribbean sit alongside images of Kelly hobnobbing with Martha Stewart and partying at the Oscars as a Marriott executive’s date.
But while the 6-foot-7 Kelly sells the dream of glamorous travel to both his readers and his staffers, the reality of working alongside the 37-year-old travel guru can be a nightmare, according to a number of former and current employees with whom we spoke.
Multiple sources described Kelly, who was also known for his generosity, as having a quick temper. Some say Kelly subjected them to verbal abuse and berated them in public Slack channels. In one case, a freelance producer claimed Kelly made an inappropriate sexual advance during a trip to Costa Rica. The CEO’s splurges — like a $50,000 personal-security bill for a work trip to Israel — became a concern for TPG’s parent company, Red Ventures, according to a former editorial employee.
The company has seen an exodus of senior employees since early 2019. At least 11 senior employees have left the company or been fired in the past 14 months.
Business Insider spoke with 28 current and former employees, freelancers, and contractors, 23 of whom described a toxic work environment they said was fostered by Kelly. Many current and former employees who spoke with Business Insider did so on condition of anonymity for fear of retribution from Kelly.
In a statement to Business Insider, Red Ventures wrote: “Mr. Kelly unequivocally denies all allegations of drug use, sexual harassment and assault. TPG and its parent company, Red Ventures, do not tolerate any form of harassment, exploitation or discrimination in the workplace and take seriously their responsibility to create environments where people feel safe, respected, and able to do their best work. All employees are held accountable to the same standards of conduct and integrity.”
Kelly’s spokesperson, Melanie Bonvicino, said in a statement: “My client Brian Kelly was unable respond to Business Insider’s query due to the confidential terms of his employment contract with TPG’s parent company.”
Success and a life of excess
Kelly got his start as a recruiter at Morgan Stanley, where he made less than $70,000 a year. The University of Pittsburgh grad began charging people $50 for his counsel on how best to use their travel reward points. In 2010, Kelly left his full-time job, and with a $10,000 loan from his parents, he launched The Points Guy.
Two years later, he sold the blog to Bankrate for more than $20 million, according to a source with knowledge of the deal. TPG is now owned by Red Ventures, which bought Bankrate for $1.24 billion in 2017. TPG, which is based in Manhattan, also has a London office that opened in 2019.
The company has been profitable every year it has existed, and its top-line revenue grew by more than 50% in 2018, Kelly told Digiday, an online trade magazine for online media, in October. Most of this revenue comes from commissions. Every time someone signs up for a credit card or rewards program via the site, the company collects anywhere from $25 to $700, the former editorial employee told Business Insider.
“I think the big thing that [TPG] got right, which is something that publishing is waking up to from a business-model standpoint, is that just putting ads in front of people isn’t good enough. You have to get people to take action,” Brian Morrissey, the president of Digiday, said.
Despite his incredible professional success, several former employees told Business Insider that they didn’t believe Kelly was fit to be the CEO of a 100-person company.
Even Kelly, who had no prior media experience before starting TPG, said in a 2019 interview with Lifehacker that he “never really wanted to run a large company.”
His ultimate goal, sources said, was simply to be famous.
“Brian would name the website ‘The Points God’ if he could,” a former employee who worked on TPG’s marketing team said.
“He got money and he got notoriety, and he was like a ‘Don’t you know who the f— I am?’ kind of person,” the former marketing employee said. “He thinks he’s a celebrity.”
Josh Dixon, a former Olympic gymnast who dated Kelly from 2016 to 2017, said his ex “definitely has an extravagant lifestyle.”
Dixon said Kelly had free rein at TPG and would take him and pals on all-expenses-paid trips around the world, traveling to the Maldives, Greece, and London, among other destinations.
“I was whisked away to Coachella for 36 hours on a private jet. I was like, ‘Oh wow, this isn’t normal,'” Dixon said.
Bankrate, the financial-services and marketing company that purchased TPG in 2012, appeared to approve of, or at least not question, the company’s spending habits.
“There was a lot of wiggle room with what he could get away with,” Dixon said, citing an extravagant 2016 TPG holiday party aboard the Intrepid, a maritime museum inside a ship docked on the Hudson River in Manhattan. “At the end of the day, he would always perform what he had to do.”
But when Red Ventures, a portfolio of digital-marketing and e-commerce companies, purchased Bankrate in 2017, Kelly’s excessiveness was suddenly seen as a liability.
During a 2019 work trip to Israel, Kelly allotted $50,000 to his personal security detail.
It was the single largest expense of the $138,000 13-day trip on which Kelly and four crew members embarked.
According to the company budget memo obtained by Business Insider, another $30,000 was estimated for a local tour company. The hotel budget was $35,000, and airfare and hotel transfers were expected to be $8,000. The rest was allocated for local fixers and location fees.
The trip included Kelly flying first class on El Al Airlines and staying in a suite at the Waldorf Astoria in Jerusalem, the latter of which Kelly booked with points.
Red Ventures cracked down on the company’s overall spending and slashed perks, replacing unlimited Seamless lunches every day with catered lunch four days per week, according to a current employee. TPG also used to reimburse everyone’s personal-credit-card fees but has now capped the reimbursements at various rates depending on the card, he added.
“When I talk to people, one of the things people will say is the perks have been getting worse,” the current employee said. “And while they’ve gotten worse, we’ve never been more profitable.”
Concerns over Kelly’s rampant partying
While Red Ventures attempted to tame TPG’s spending, Kelly still remained known for an over-the-top lifestyle in his personal life, which Dixon described as “sex, drugs, and rock ‘n’ roll.”
The travel honcho hosted parties at his homes in Manhattan, the Hamptons, Pennsylvania, and Miami Beach, the latter of which he sold for $2.59 million in 2019.
“There were a few times where even he would say he had been partied out of house and home in East Hampton,” Dixon said, adding that the raging would become too much for Kelly to handle and he would leave his own house while his guests continued carousing.
Another Kelly associate said, “There would be points where I would be concerned about some of the drug use … it was very jarring.”
The partying would sometimes seep into Kelly’s work life too, according to sources.
A contractor who traveled with Kelly said that on work trips, the CEO “was drinking and partying in a way that was not professional. I think that he was a bit disinterested in the work and more interested in getting drunk.”
A freelance producer said Kelly got “blackout drunk” during a 2016 work trip to Las Vegas. After Kelly attended a Jennifer Lopez concert, the CEO was unreachable the following morning, according to the freelance producer, and the team missed its flight to the Sundance Film Festival in Utah.
“He didn’t wake up until like 2 in the afternoon, and he had to book a private plane to get us there,” the freelance producer said. A TPG contributor who was also in Vegas confirmed the incident to Business Insider.
That same freelance producer, in addition to the TPG contributor, said they witnessed Kelly doing cocaine on at least two work trips. The freelance producer said on one occasion, he saw Kelly partake in the illegal substance in a room at the Nobu Hotel during the 2016 Vegas trip.
Two individuals, the freelance producer and another source, also said Kelly asked them to procure cocaine for him on work trips in Asia.
During a trip to Japan in spring 2016, the freelance producer said Kelly requested cocaine — demanding he not come back without it.
“He basically makes it like your job depends on it,” the freelance producer said.
The other source echoed the sentiment, saying Kelly told him during a separate Asia trip, “If you want to get the other half of this check,” when the CEO requested the source go out and find him drugs.
Nonetheless, even after partying, Kelly managed to put on a presentable front for TPG.
In 2013, a friend said Kelly “went on live TV after not sleeping and on a bender,” adding that with Kelly’s composure, “you would never know.”
But his partying, at one point, led to an allegation of an inappropriate sexual advance during a work trip.
The freelance producer who had traveled to Japan and Vegas, said Kelly attempted to kiss him in the pool at the Andaz Costa Rica Resort at Peninsula Papagayo during a work trip in March 2016, a few weeks before they traveled to Asia.
“Our last night in Costa Rica, we were filming for JetBlue, and he just kept on getting more and more tequila and then he wanted to go in the pool afterwards,” the freelance producer said.
“He swam up to me and came up in front, so I had my back to the wall, and put his arms on both sides of me, so I was kind of trapped. And then he pushed his whole body up against me so I was pinned between him and the wall. He just started trying to make out with me and I was like, ‘What the f—?’ and pushed him off and swam away.”
According to the freelance producer, two friends of Kelly’s were in the pool at the time. One friend did not respond to requests for comment. The second friend said he was “not sure what you’re referring to” when emailed about the incident at the hotel pool. When Business Insider provided further details via email, the second friend did not respond.
The freelance producer says that he went back to his room at the Andaz Papagayo hotel alone after the incident with Kelly.
“I was just in shock and very uncomfortable,” the freelance producer said. The next day, the freelance producer flew to Mexico to meet up with his friends. He said he did not make a complaint to human resources because he was hired as a contractor and it was his only job at that time since he had just moved to New York.
The freelance producer told both his best friend and another TPG contractor about the incident. The TPG contractor confirmed to Business Insider that he remembered hearing the freelance producer’s account the next morning, and the best friend confirmed he had heard it two days later, in person in Mexico.
While Kelly’s drug use remained an “open secret” among colleagues at TPG, according to the former editorial employee, Red Ventures enforced a strict no-tolerance policy. A former senior colleague and the former editorial employee told Business Insider that one of their coworkers was fired after acknowledging using a marijuana vape pen in June at the New York City Pride March, where TPG had a Boeing 747-themed parade float.
After Red Ventures bought TPG, all new employees were required to take a drug test. Those already at the company were spared, multiple current and former employees told Business Insider.
Some ex-employees describe Kelly’s treatment of his staffers as condescending, rude, and unprofessional
Despite working at a company hailing high-flying travel and five-star hotels, office life could be tense at TPG, according to sources.
Several former employees described a pattern: If you didn’t challenge Kelly, they said, you’d stay on his good side. But the moment you started to question his decisions, your days at TPG were numbered.
“I’ve seen it happen with three separate people,” a former staffer said. “You get on that bad side, and then it snowballs and snowballs, and then you’re eventually pushed out.”
Often, Kelly’s “public shaming,” as several sources called it, would take place on Slack.
Instead of sending a direct message to the person and their manager, Kelly would regularly attack the person in the companywide Slack channel, according to sources. The former senior colleague said Kelly would ridicule staffers and write comments along the lines of: “How could you not have thought of this already? How could you still be failing like this?”
Some said his temper was well-known among employees.
On one occasion, during a meeting in Kelly’s office, a former high-level TPG source said the travel CEO “threw down his phone in anger” regarding a work-related matter, and it bounced across the desk toward her.
“I was very startled,” she said. “Not only was it unprofessional, inappropriate, and a reaction disproportionate to the situation, it was honestly very scary coming from someone who was in a top position of power. I’d never had a fellow employee — let alone a superior — display physical aggression like that in a meeting.”
A former executive said that when he was at the company, Kelly would occasionally miss meetings with important partners, such as airline and credit-card representatives, and be hostile with those who actually attended, contesting decisions made in his absence.
The former senior colleague said she thought Kelly had little faith in his team members.
“He would trust almost anybody in the world before he trusts his own employees,” she said. “He will trust [reader] comments over what we say is the best strategy, or a random person he met at a party over anything that we would have to say.”
A number of employees would resort to asking their friends to leave comments on TPG stories, videos, or posts so that Kelly would see their suggestions and hopefully execute them.
A contractor who worked with Kelly for about one year said, “I found the job so emotionally and professionally abusive that I needed to seek therapy.”
A volatile work environment
The current employee told Business Insider that The Points Guy’s Manhattan office is a revolving door, with Kelly ousting people he doesn’t like with little to no explanation.
“It leads to a sense of confusion in the office of, ‘What’s going on? Who’s next?'” he said.
A second current employee added: “Everyone who deals with him personally complains about it.”
The former senior colleague said that Kelly gravitated toward the newer employees.
“Brian likes new and shiny things,” the former senior colleague said. “Whenever there’s a new person that is hired, they’re his new favorite toy … he treats you like you are the smartest person in the world. He takes everything you say to heart. It’s great. But I’ve never seen that last with anyone at the company.”
Three former employees told Business Insider of an instance when a freelancer was offered a full-time job at TPG after working at the company for several months. According to each, the freelancer accepted the written offer, after which she disclosed she was pregnant. Over the course of negotiating, TPG abruptly withdrew the offer, telling her the position was no longer available. By that time, she was almost five months pregnant. It was later discovered that the job listing had been posted on LinkedIn shortly before the freelancer’s offer was rescinded.
Former employees said that despite the downsides of working at TPG, Kelly could be generous and charming.
Amy Nobile, a friend of Kelly’s who has traveled with him to places including Guatemala and Iceland, told Business Insider that Kelly is a “generous soul” with his friends and family and would often have lavish surprises planned for their trips, including a helicopter ride to Reykjavik, Iceland, after they exited an ice cave.
Years after a former colleague’s husband helped teach Kelly search-engine optimization, Kelly gifted the family enough points for a trip to Ireland.
This generosity sometimes extended to his employees.
“If someone in the office is getting married, then there might be points for a honeymoon,” Nobile said.
At a 2018 party Kelly hosted for TPG employees on the rooftop of his apartment in Manhattan’s Flatiron District, the former editorial employee said he gave away flight credits for the person who typed in Slack the fastest: “Brian is the world’s best boss.”
The former high-level TPG source likened her experience of working with Kelly to having an alcoholic father.
“You might get the dad that is in a great mood and is giving out gifts and praise like it’s candy, or you might get the bad dad who is on a raging bender,” she said.
Despite raking in millions, some insiders say Kelly lacks credibility
While many insiders in the points and miles industry admire Kelly for bringing their niche to the mainstream, some believe Kelly’s coziness with credit-card issuers prevents him from offering unbiased credit-card advice.
“It’s a difficult balancing act because at the end of the day, people won’t trust your recommendations for credit cards if they think they’re being driven by the needs of the credit-card companies,” Digiday president Brian Morrissey said.
Much of this boiled over when Marriott’s global marketing officer took Kelly as her date to the 2019 Oscars.
Kelly defended himself in an Instagram post, saying he was invited to the Oscars as part of a small group of ambassadors for Marriott Bonvoy, the brand’s loyalty program, which a Marriott spokesperson confirmed to Business Insider.
I try to take two solo trips a year- to slow things down and refocus. At first solo travel is a little awkward, but you get used to it once you stop caring what other people think (why is this guy by himself on a romantic honeymoon island?!) Last year my trips were to @amanyara_resort and @kayamawa_malawi, the latter being incredible and the former being decent. This year is @barosmaldives and ???. Any suggestions? Ideally I like good diving spots. Palau? Tahiti? Philippines?
Despite the criticism, friends describe him as a visionary with deep commitment to his work.
Adam Kotkin, TPG’s former chief of staff, told Business Insider that if Kelly didn’t like running the company, “he probably wouldn’t be there.”
“Without a doubt, he wouldn’t want to do anything else … he is giddy about airplanes … and trying new things,” Dixon added. “There’s no question that he loves what he built.”
Still, the life of excess has its pitfalls.
“If you’re really good at it, it’s going to be exhausting,” Dixon said. “At points, I remember sitting in a hammock in the Hamptons and asking him, ‘Is this lonely?’ And he was like, ‘Yeah, it is.'”
Disclaimer: Insider Inc, Business Insider’s parent company, has an affiliate business partnership with The Points Guy.