Editor’s Note:  Caitlin Thompson is the founder and publisher of Racquet Magazine — a cultural tennis publication, platform and movement like no other.

Caitlin and I caught up in Miami Beach on the tail end of ‘Racquet House’ — a quarterly in-person celebration of Racquet, grassroots tennis and its global community.

This interview has been edited for length and clarity. You can listen to the full conversation here.

Racquet House is state of mind. It's a roving community where people can walk in the front door of tennis.

On Racquet House.

Cornelius McGrath
Caitlin Thompson. Welcome to Miami, I guess.

Caitlin Thompson

Welcome to the house we're staying in. Got a little pool, a little Palm tree.

So this is Racquet House?

Racquet House is a little bit of a state of mind, Cornelius. This is not the venue for our event. Our events typically occur at various luxury properties, public tennis courts, and everything in between.

We like to do both the public and private merging together. So we had access to a very glamorous house, which was great. We've done a few events at places like that, but also we want to make the tennis portion very accessible to people. So we like to also partner with public tennis facilities and bring people into tennis who maybe don't have the first idea about how to step into it.

By covering the costs and giving them instruction and making it fun, and wrapping it around either a very high-end real estate experience or something as simple as showing up to the courts down their street, we feel like we can philosophically align.

So this particular house is not Racquet House. This is just where we're staying for the weekend. Racquet House is, like I said, a state of mind. It's a roving community where people can walk in the front door of tennis as a sport that is beginning to understand the possibility of what happens when you invite more people in than you did before and how that can change you and the sport for the better.

Wonderfully said. So let's set the scene. It's 90 degrees. It's baking. This might be the hottest podcast I've done. I've just met you at the Miami Beach Tennis Centre, catching the tail end of Racquet House. This is the third that you've done?

This is the fifth that we've done. We've done one in Palm Springs. We did two in LA. Now Miami. I'm leaving one off. It'll come back to me. The next one is in London on Arthur road, which, if anyone knows SW19, is a stone's throw from the All England Club.

We'll have the backyard, pool, and garden area of a beautiful private home, very close to Wimbledon Village and the tennis tournament. The idea is to really bring communities together. So the idea is that they're either a cool class of people, a crew of people who live in a place that's already amazing.

Like when we go and do live podcast taping in London, whether it's in Shoreditch or at St John's in the middle of town or, more on the west side. We're finding people who love art, culture, and love music. They have a tastemaker sort of veracity of authentic viewpoints, but also, they're voracious in how they consume culture and ideas. London is a very strong tennis community, especially during the fortnight.

And so that collision of people who are maybe the culture people and the people who are training their lens on tennis can overlap if you make a space for them too. And so that's how we think about where we bring this the manifestation of the pages of Racquet magazine, or an embodiment of sort of the visual language that we've developed for more distributed social media channels, like Instagram and other places, or the conversations we have on our podcasts. Those can all collide at a location if there's a community and sort of a good reason and good timing for them to do that. And so we look at these things as popups that happen where we can sort of offer space and really pull in some naturally occurring things that might not have occurred to people.

So this is your fifth Racquet House. Tell me about your first.

The first one was in Palm Springs at the Dinah Shore Estate, which is a traditional mid-century modern House. There was a private tennis court. There was a pool. There was a pool cabana. And like any Racquet House, what we try to do is a combination of really high-end F&B. We worked with several sponsors, Ciroc, Sergio Tacchini sponsored it. We had a sponsor in the form of Wilson who did all of our on-court activations. We had a few other very generous sponsors - Stella Artois and Jess Lauder. And I'm not trying to rifle off names of brands as much as just to sort of say these were all brands who wanted to be in the tennis space and maybe didn't have the sort of younger cultural way to do it before we offered it them.

Traditional sponsorship opportunities where you have the Stella Artois logo on a giant billboard at a tennis tournament or paying to be in the background of a TV shot are tried and true methods of getting your brand out there. On the other hand, they're not high return, storytelling driven mechanisms. And so when we're putting together Racquet Houses, it's important for us to work with brands because we don't charge people to attend them. That's a huge, crucial component of how we think about them. We want this community to feel like they can step into this. And the cost is something that is very sensitive in the tennis space, because I think wrongly, a lot of people assume it's all about money and you have to have a private club membership and you have to have the gear and all this stuff.

And the truth is tennis is quite inexpensive. You can play on a public court with two Racquets and a ball. But the opportunity for people to do that and the storytelling around it hasn't emphasized that anything other than a cloistered country club environ is the way to do it. And I think for us because we don't charge people to attend because it's invite-only because we want people from all walks of life in every way - socioeconomically, racially, gender, sexuality—all the stuff.

We want a true reflection of our community who are tastemakers and maybe, in some cases, influential or influencers, but the idea is that they can come and partake of this and share the messaging. Sure. But also we can get it paid for because brands are more than happy to have a really vibrant community embracing or learning about, maybe new product launches that they have or things that feel really authentic to them and us.

And so that's how we pay for them. We get these sort of relationships built, and we don't charge people money because we have found that if you charge people money to attend something, you tend to get people with money who are not necessarily reflective of our audience. Tennis has, for a long time been about expense and elite.

And those things are not only not interesting to us, I think they're déclassé. And gauche, frankly. So, we have wealthy people asking to be put on the list. And they say, "we can pay." And we say, "oh, are you cool? Are you going to bring the right energy to this? Do you understand what you're doing? What we're doing here?" And if the answers are yes, we will absolutely invite anybody. But it's more about fitting this model of the community that is self-policing at this point and self-referential.

And I think that's something that I'm really proud that we've built because we think about that community, whether we're programming a Racquet House where there's on-court activation, food and bev, a place for a brand to have a meeting. We're recording live podcasts, we're creating content, and we're doing a photo shoot. You caught us today at the tail end of a photo shoot, which I'm sure we will talk about. But the idea of this whole thing is that we're creating the culture. And so, to do that, you need to get the right mix of people who are creators to be part of it, whether they're attendees or collaborators, or, as in many cases, both.

So, how do you know you've been successful? Is it a feeling? And I guess from first to the fifth Racquet House, what have you learned about what works and what doesn't?

The first one popped off right before the pandemic. We did the first one and then had about an 18-month break because almost no one was convening in person. And so for us, we had a lot of time to think about what looked great but wasn't actually that great in person. What maybe looked less exciting but was really great in person and how we could get the content that we created in those spaces to be even better. I was unhappy with the first photoshoot we did for the product. I didn't think it was as good as it could have been. I didn't think we cast the models right. Just the sort of things that you're like, "ah, knowing what I know now, how do we do this?"

What we found is a lot of the artifice, and a lot of the sort of constructs people come to us with. Like the first photographer we worked with on that first photoshoot for Sergio Tuchinni in March of 2020. It was a casting agency, and there were models, and they were bussed in, and we spent a lot of money, and there were stylists, and that's all great. There are some tremendous, tremendous people in this space. The stylist we worked with, Sarah, she's a fantastic stylist. I would love to work with her again. But the photography wasn't quite right; the models weren't quite right. I'm sort of harping on this because the truth is the food and bev portion was awesome.

The party was awesome. Our sponsors were awesome. The court was popping off, whether we had a clinic planned for new tennis players, experienced tennis players or anyone in between. Like there was always action going on. There were always people in the pool, and the coolest people came through. Some boldface names, but also the creative director who's in from Lacoste from Paris is here, and his crew are chilling by the pool, and they're going to play a set. Collisions and collaborations and ideas are created. And that is one throughline that we've kept that I'm thrilled with. Just from a sort of product standpoint, I think that that the photography was not us. It felt stilted. It was very 'fashion' in a way. We found our fans don't like the artifice.

And so today, when we did a photoshoot with the incredible Molly Crana, we let her and one of our staff, art direct, and it was using the implements of a public tennis court. And it was so much more of us. We had many more sorts of tattoos. Nobody looked airbrushed in a way that I think when people looked too "modely" they don't play tennis. At least I can tell when you're watching somebody who's meant to model sports clothes, and they don't play the sport. And I think that is an immediate signifier that somebody's co-opting a community instead of celebrating it. And so what we started doing is casting photo shoots, product ideas, and collaborations from our own community. And today, we have had a friend and a former professional tennis player - who's now going to be our intern - be the main models of the photoshoot. And that is one concrete example that I can say we've really evolved. Our products have gotten better, and the way we produce imagery has gotten better because it's much more aligned with how we cast it and how we're using it to further the community's efforts, ideas, membership, whatever it is.

We make it cool for these players to step into our culture. They want to come because they understand that we're doing something that has a different dimension.

On Creating Cultural Currency.

What's the...