Racquet Magazine’s Future Up In The Air After One Cofounder Removes The Other

1:27 PM EST on November 13, 2023

Trendy tennis magazine Racquet is facing an uncertain future after the removal of top editor and cofounder David Shaftel, whose exit was the culmination of months of disagreement between him and publisher/cofounder Caitlin Thompson over the direction and financial state of the company.

In an email sent to staff and contributors on Nov. 3, Thompson announced that Shaftel had left the company "after we couldn't agree on the best path forward."

"Obviously after building Racquet together over the better part of eight years, this wasn't a turn of events that in any way was taken lightly," Thompson wrote in the email, which was viewed by Defector. "I know a lot of you are very close with Dave, and I truly tried everything I (and a whole bunch of lawyers) could think of to avoid this, but in anticipation of things ending up with this outcome, I've been in planning and transition mode for some time. I've got a new board and management team gearing up to take things to where I and the investors think they need to go, and I hope that means that we'll continue to work together in the months, weeks and years to come."

According to Shaftel, Thompson had urged the company's preferred shareholders to remove him from the board—they were the only two people on the board—so she could fire him, although he continues to retain approximately 32 percent of shares. (The company was essentially split into thirds among him, Thompson, and various preferred shareholders, with a small number of unallocated shares.) Shaftel told Defector that the reason for his ousting was because he had lost confidence in Thompson's business management, and that her decisions caused Racquet to run out of funds in October.

Thompson said in a conversation with Defector that since September she and Shaftel have mainly communicated through lawyers, and that he was the one who tried to push her out because he "just didn't want to go forward together." (Shaftel called this "revisionist history.") She said that when she presented a plan to the shareholders for the future of Racquet and Shaftel did not, the shareholders voted to remove him. When asked whether the company currently had money, Thompson said, "We're getting a new round of investment." She declined to elaborate.

"We had a schism in the way we wanted to go forward with the business," Thompson said. "Increasingly we've been growing, which is great, but also we've had a difference of opinion in how to spend our time and how to punch above our weight, as something really small."

For Shaftel, the fundamental issue was that he believed Thompson was more interested in revenue than profit in order to create a high valuation for the company, while he said he wanted sustainable growth and to become cash-positive. In his eyes, the magazine had a small but loyal audience and could succeed if it focused on growing that readership organically. "When we got to a point where things became too grandiose, that was really where we went wrong," he said. "The plans became too grandiose and unrealistic."

Shaftel acknowledged that there were legitimate ways to scale while raising money—Racquet had gone through two small rounds of investment in 2019 and 2021, according to Thompson—but found it unreasonable for the company in its current state. He also said he no longer trusted Thompson to spend those funds judiciously.

What Shaftel referred to as "the end of the company as we knew it" was due to a pair of crippling financial missteps earlier this year.

"She will say that the company was insolvent, and I wouldn't let her raise money, because she needs me to sign off to raise money," Shaftel told Defector. "That is true, but if I was to take a red pen to that statement, I would say: We are insolvent because of her reckless actions, and I wouldn't let her raise money because I lost faith in her leadership."

Thompson and Shaftel first met through a mutual friend who had worked with each of them at separate publications. They met in 2007 and bonded over watching tennis at a bar; days later they attended a U.S. Open match between Rafael Nadal and David Ferrer. As they got to know each other, they talked about the idea of starting a publication that would cover the sport in a way that wasn't accomplished by traditional tennis media.

Incorporated in 2015, Racquet launched its first issue in the summer of 2016, after a successful Kickstarter campaign raised $55,000. Its mission was to cover tennis culture beyond individual matches, with a specific style and emphasis on sleek illustrations and photography that thrived in the print magazine format. The magazine featured contributions from writers like Taffy Brodesser-Akner and Ben Rothenberg, and players like Andrea Petkovic. In 2021, Naomi Osaka guest-edited an issue. In addition to her role as publisher, Thompson hosts a podcast with former Grand Slam doubles champ and tennis coach Rennae Stubbs. Defector staff writer Giri Nathan regularly contributed to the magazine and its Friday newsletter, On Court. (Nathan said he was told by Thompson that the newsletter had been "put on pause," and he had no current projects in the works for Racquet.)

Tennis has always had a satisfying aesthetic, and Racquet was "the purveyor of all the things cool and fashionable in this sport," according to one person who worked on the creative side of the company and requested not to be named. The crisp colors, distinct fashion, and picturesque courts translated well to a print format that really popped on a coffee table or desk. The accompanying articles were enthusiastic and adventurous. Racquet was doing its own thing, seeking to advance tennis writing beyond "Roger Federer as Religious Experience," and the community embraced it.

Thompson served as publisher, and Shaftel as editor. Due to the slim staff, their responsibilities would sometimes overlap; in smoother times, Thompson would contribute on the editorial side and Shaftel would have a voice in the business aspect. But Shaftel primarily handled the editing and writing, and Thompson would set up meetings and find ways to get money through projects or investments.

"Most of my job is email, and I can do that from anywhere," Thompson said in a September interview with The Cut. "I’m talking to people, pitching brands, working on our events, merger calls, et cetera. But the actual work I do is managing the vision as it comes to life. This morning, I answered emails and got some admin out of the way to keep projects moving, all from the bench while waiting to get on the court. I meet with people on the court, whether they’re investors or collaborators, because it gets people in a state of play. When they’re in a state of play, they’re creative, they’re open, they’re a more vulnerable version of themselves."

Craig Shapiro, a documentary filmmaker and the host of an eponymous tennis podcast, first learned of Racquet in 2016, when he showed up to one of the magazine's events at the private tennis club Court 16 in Brooklyn. A self-described "hired gun/friend of the magazine," he befriended both founders, wrote articles for Racquet, and collaborated with Thompson on other projects for the site through his production company.

Shapiro, who sat in on calls as Thompson met with clients, said she had a lot of charisma as the face of the magazine and was adept at getting people to buy in, but tended to overpromise and force him to scramble when the circumstances of a project changed.

Over the years, Thompson had come up with extraordinarily ambitious ideas for the future of Racquet. "All she ever really talked about was valuations and money-raising, and buying these big crazy things," Shapiro said. He and Shaftel independently mentioned times when Thompson mused about wanting to acquire a tennis club in Spain, or buy the TV network Tennis Channel, or even the United States Tennis Association. But it was unclear where the money would ultimately come from, and the dreams never solidified into real plans. When asked by Defector, Thompson denied these ambitions. "I didn't discuss buying those things, but we did discuss maybe doing some partnerships," she said.

As time went on and more brands got involved, the company took on increasingly more aspects of a creative agency, seeking a path to monetize Racquet's cultivated coolness. It published non-editorial content and worked on projects for brands including Fila and Sergio Tacchini. There were collaborations with Adidas, including a custom shoe. For the first issue, Racquet threw an event at the Ace Hotel location in London. These projects presented another revenue stream beyond subscriptions and merchandise.

It's not uncommon for a stylish magazine to capitalize on businesses desiring a piece of that style. Canadian journalist Tyler Brûlé founded the design magazine Wallpaper in 1996, sold it to Time Inc. a year later, then launched the agency Winkreative in 1998. In 2007, after his non-compete clause lapsed, he founded another fancy magazine called Monocle. For Thompson, part of the inspiration for Racquet came from a 2015 Nieman Lab interview with Brûlé, in which he talked about how to grow a "quality audience." In a 2017 Nieman Lab prediction, Thompson wrote that Racquet's goal was "identifying a niche audience centered around highbrow tennis culture and providing a premium experience at a premium price." Shaftel, who had previously freelanced for Monocle, drew from his experience only "in the sense that I wanted it to be a useful magazine, something that you could read cover to cover, rather than something that just looks pretty." Thompson pitched that combination of style and substance to people with advertising budgets.

"That's the blueprint for a print magazine becoming profitable," Shapiro said. "You become the creative agency for the brands that want to be in Racquet. Where can Chase Bank, or Evian, or American Express, or Yonex, or Adidas—where can they go once you leave that tournament? Racquet. It was the perfect place to hang your hat."

While there were differing opinions on whether some of these projects were on-brand for Racquet, the company's approach was alluring to the tennis world and provided plenty of opportunities to make money. But those who spoke with Defector broadly agreed that there was an issue with Thompson's inability to execute on these opportunities. "It did not have a person leading that charge that had the business acumen to follow through on those promises," said the person who worked on the creative side, who then left the company when it was clear that Thompson's goal was to plan events at an unrealistic frequency.

According to Shaftel, the decision that struck a critical blow to the company came this past May. Thompson was in charge of organizing the Racquet House at the Palais de Tokyo in Paris, held before the French Open. She planned the three-day event under the belief that the sponsors would come through with the money promised in a verbal commitment, but the final number came in a lot lower, leading the magazine's party to be approximately $200,000 over budget. Shaftel told Defector that he saw that deal as a "sackable offense," and had a falling-out with Thompson, but they attempted to repair the partnership and move on.

Roughly three months later, it more or less happened again. Thompson planned another multi-day Racquet House event in August at Rockefeller Center in New York City, as part of the lead-up to the U.S. Open. It included speaking panels, a party, a special tennis court, and more. Racquet had a prime location and received a mention in a Today show segment. Again, the budget for the project did not match the sponsors' financial commitment: The difference was approximately $200,000. When asked about budgets for the two events, Thompson declined to comment on financial details of the company.

"We were out of money before [Racquet House NYC]," Shaftel said. "The fact that that happened again, and we lost a ton of money again in New York, three months later ... We had a talk and we tried to patch it up and keep going after Paris, and by the time it became clear to me that we were also going to lose a lot of money—the same exact series of unforced errors was going to happen again—I just couldn't believe it. I couldn't believe we were in the same position again, and once that happened, things were irrevocably fucked."

Shaftel had spent the last couple of months working on the 24th issue of Racquet, but pushed it back to January to coincide with the Australian Open, because he said there was no money to continue putting it together. In the weeks before his firing, he said he focused on publishing the newsletter and speaking with lawyers.

When asked about his future plans, Shaftel said he hoped to work on something new within the same realm. "Through this process, I've felt very supported by the creative community that's helped me make the magazine, and I plan to continue working with them."

Before her falling-out with Shaftel, Thompson had dinner with Shapiro in Los Angeles, and said she tried to convince him to do more work with her.

"I essentially said, Just work it out with Dave. Once this thing resolves itself, let's see how this thing goes," Shapiro said.

That dinner was the end of their collaboration. "I knew at that moment that we were never gonna talk ever again," he said. "That's how I feel right now. If we do speak, it's gonna be pretty acrimonious, is my guess."

The future of Racquet is unknown. In speaking with Defector, Thompson said multiple times that she wanted to find a way forward with Shaftel to keep the company going and continue the print issue. "My hope is we can still figure out how to somehow work together, if not in the same place, then certainly within parallel ways to make Racquet work," Thompson said. "At the end of the day, Dave really cares about this, as do I." She said she planned to hire four or five people within the next 18 months.

"I don't have any intention of letting this fail," Thompson told Defector. "For me, going big is in a lot of ways the best way to make the best future for Racquet possible. I think that's, at its core, a little bit of a difference between us."

Shapiro didn't think it was out of the realm of possibility for Racquet to successfully complete its pivot to a creative agency, depending on whether Thompson can pull it off. His words illustrated a running theme among the conversations former contributors had with Defector: They were proud of the work they did, and frustrated that it all fell apart like this. "We honored the past, we garnered the new kids, we pulled a community together in a way that nobody else has done in tennis," Shapiro said, "and it was something special."