When I first started dreaming about our future Bradenton beach house, I knew I wanted to niche hard into the sports world and IMG Academy vibes. For months, I spent hours at night with ChatGPT — exploring how I wanted people to feel, who I wanted to host, and what would make this space different yet absolutely needed. (Many names and logos came and went during that season, and yes, Chat — a.k.a. “Goldie” — became my new bestie in the process.)
The first house we were under contract on didn’t work out, but honestly? That was the best twist of all. What became The Sideline Club is far more aligned with my vision than I could have imagined. Proof that unanswered prayers are sometimes the sweetest gift.
Design, though, was going to be crucial. Having designed my own STRs (and a handful for clients), I knew I could get lost in the rabbit holes of indecision, and time was not on my side. That’s when I called on the perfect partner to bring my Vintage Varsity storyline to life: Paige Hayes with Hayes & Company. Equal parts badass hipster and old-school class, she was the match made in heaven I absolutely knew I needed to land.
It couldn’t have been easy for her to hear me insist on nailing a very specific guest avatar — all while both of us were rejecting the cliché “Florida beach house” aesthetic. But maybe that’s exactly why she took the project. Together, we had one big goal: to design a stay that felt as intentional as it was a vibe — stylish enough to feel like a boutique resort, but purposeful enough to hone in on performance and recovery.
From that foundation, the design story started to unfold. We weren’t just picking paint colors or furniture — we were building a brand. The Sideline Club had to feel nostalgic, like stepping into a throwback racquet club where all belonged, Every material, the layout choice, and chosen amenities had to answer two questions: Does it feel intentional? and Does it support performance?
At the same time, I was pulling together the dream team of women who would help shape The Sideline Club into reality. My friend, the talented Umi Haft-Funke, who designed my original Nest Collective logo, was the first call to set the tone. She helped put to paper the brand colors and logos I was describing with words, that now will give The Sideline Club its bold, recognizable identity.
Because the guest experience has always been as important to me as design, I turned to Dawn Asher of The Olive Jar. Together, we’ve been crafting those key touchpoints — the little moments of surprise, delight, and consistency that turn a stay into a hospitality experience. Dawn’s presence onsite became the icing on the cake, seamlessly pairing with Paige Hayes’s design vision to make this space feel as intentional as it is on brand.
From day one, I’ve described the concept like this to them: “If Ralph Lauren and Lacoste had a baby, and Aviator Nation was the godparent… that’s how I want The Sideline Club to feel.” Bringing that vision full circle has been possible also thanks to Steph Weber of The Weber Co, who laid the foundation for our content and marketing strategy. Email marketing has always been my kryptonite, and brand strategy can feel like a foreign language — but Steph gave us the playbook. Slowly but surely, I’m determined to make her proud.
And soon, as construction wraps up, I’ll get to cross the finish line with the help of my dear friend Kim Fitzpatrick of The Launched Host. Kim will carry this project from design into launch, ensuring every last detail delivers on the promise we’ve all worked so hard to create.
So you see, the “design” of The Sideline Club isn’t just mood boards and product sourcing. It’s been a collaboration of incredible women I’ve met in the vacation rental space over the past five years — each one bringing her own genius to the table. To me, that feels so fitting. I’ve always believed in “community over competition,” and now I get to live that out in the most tangible way. The Sideline Club is becoming every trophy pun imaginable — not because of me alone, but because of the tribe of strong, talented women who are helping bring this dream to life.