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🪩 Volume 134 | April 29, 2026

 

I spend a lot of time in this newsletter dissecting brands—what they did, why it worked, what you can steal. And I LOVE it. But also hey hi just FYI, I don’t always wake up thinking about brand strategy… in fact most days I wake up with a 4 year old asking me if she can turn on the lights and color (lol).

 

I also often wake up checking my calendar, and getting the kids ready to go off to school. Or if it’s the weekend, waking up slow for breakfast and hanging out with my kids (staying far away from WORK).

 

Sometimes the most useful thing I can do is bring you into my day-to-day and show you how marketing shapes my world as a consumer. Take what you need.

 

I spent almost all of last weekend outside with my family—completely off the content hamster wheel. It’s Florida in late April, which, if you've never experienced it, is somehow still perfect before the scorching heat hits. We took the boat out to Sanibel—my FAVORITE beach, 45 minutes from our dock—and the water was UNREAL (crystal clear).

 

After the beach, we grabbed lunch at Gramma Dot's—dockside at the Sanibel Marina, no reservations (they don't take them).They’re  absolutely PACKED from the moment they open. Then my husband and I went RV shopping—yes, we are becoming RV people, more on that in a second—at Blue Compass RV in Fort Myers. And then we ended the weekend at Blossom & Brie—a farm-to-table restaurant on an 86-acre working farm in the literal middle of North Fort Myers—where I had the best steak of my entire life.

 

No ads were involved in the making of this weekend. No influencer recommendations, either. I found each of these places through being local, being curious, and being a person who was just present in her own life for two days.

 

Which obviously got me big time thinking today… ready to go on a ‘lil adventure??

 

 

 

 

 

It shouldn't still be THE spot. Sanibel has no shortage of waterfront restaurants. It's a tourist island—new spots open, influencers cycle through, TripAdvisor rankings shift. And yet Gramma Dot's, which has been sitting at the Sanibel Marina since 1989 and is literally named after a real woman (Dorothy Sterns, who arrived on the island in 1963), is still the one everyone goes to. The one locals bring their out-of-towners to. The one that was standing room only when we pulled up by boat on a late April afternoon—which is supposedly the shoulder season.

 

They don't take reservations or do call-aheads. They are a casual dockside seafood with warm hospitality, fresh fish and ridden with families smiling big about their beachy “vacation.” They've won the People's Choice Award seven times in a row!

 

For your business: Are you THE place for something? Not the best in the world, not the cheapest in town—just the ONE, for a very specific feeling or moment or person. Gramma Dot's is the place you go when you want to feel like you're really on Sanibel. What's your version of that? And more importantly—does every single touchpoint in your business actually deliver it?

 

 

 

Let me set the scene: my husband and I walked into an RV dealership on a Saturday afternoon having done approximately zero research (other than renting a Coleman Lantern 17B a few weeks ago for a weekend). We know we want a travel trailer—bunk beds, queen bed, dinette, bathroom, small kitchen—because we're road-tripping to New York this summer and the hotel thing isn't cutting it anymore. That was literally the extent of our brief.

 

Now, if you’ve ever bought a car, you know the feeling of walking onto a dealership lot (and the pep talk you give yourself to hold firm in your negotiation skills, or if you’re like me, shake in your boots because you have none HAHA). The immediate sense that someone is about to work their sales schemes on you, the performative friendliness that doesn't quite reach the eyes, aaaand the subtle pressure that starts the moment you make eye contact.

 

Blue Compass didn't feel like that AT ALL. Our sales(wo)man [Zoe, I adore her] didn't pitch us. She asked questions, listened to what we actually needed and eliminated options instead of adding them. We walked out having narrowed down to exactly what we want, without feeling like we'd been talked over, ignored, or upsold on something we didn’t need.

 

According to my digging, Blue Compass has been on a deliberate mission to rebuild what buying an RV feels like—and it shows in how their team is trained, how their space is designed, and how their new flagship was built from the ground up with customer experience at its core.

 

For your business: What's the default assumption someone makes before they walk through your door—or land on your website? Every industry has its baggage. Car dealerships have theirs. What's yours? And what would it mean to be the business in your category that actively, visibly dismantles it from the very first touchpoint?

 

 

 

This place should not work on paper. It's not on a main road, not in a trendy neighborhood and has ZERO foot traffic. You have to WANT to go there—which means you have to KNOW about it first, which means someone had to tell you (or you have to stumble across them on IG).

 

And yet: Blossom & Brie has 28,000 Instagram followers, a Gulfshore Life feature and a plethora of reviews that read less like Yelp entries and more like someone trying to explain a feeling they can't quite get out of their chest. (I know because I've been that person since Saturday night.)

 

They built a restaurant where the farm IS the experience. About 80% of the produce comes from the property—including a 40-foot hydroponic freight farm they installed specifically to maintain steady harvests through Florida's storm season. The meat is sourced on-site (until they run out, and then they locally source). The dining room is essentially a linen-clad mess hall surrounded by actual livestock and fields. You can SEE where your food was sourced FROM YOUR TABLE. That’s what sends people 45 minutes out of their way, and has them texting their friends about it before they've even finished dessert.

 

For your business: Specificity is a magnet, not a filter. The more clearly and completely you commit to what you ARE—even if it means a lot of people won't get it, won't find it, won't bother—the harder the RIGHT people will drive to reach you. Blossom & Brie isn't for everyone—but the right people WILL find it, rave about it, and come back.

 

 

I'm not saying these places don't market themselves at all.

 

But the reason they were all FULL on a random April weekend wasn't the ad spend. It was that none of them are out here chasing a tactic that has nothing to do with who they are. The trap a lot of local businesses (and a lot of brands trying to grow) fall into is thinking that more reach equals more relevance—so they start throwing budget at whatever's trending, when the most compelling thing about them was already there.

 

Gramma Dot's doesn't need to go viral. Blue Compass doesn't need a rebrand gimmick. Blossom & Brie doesn't need to be on every food blog in Southwest Florida. They just needed to be really, genuinely, COMPLETELY themselves—and let that do the work.

 

The shiny tactic will always exist. The question is whether your foundation is strong enough that you don't actually need it.

 

I have been watching Gap do its THANG lately and I cannot look away.

 

This is a brand that, let's be honest, spent a solid decade being the punchline of its own nostalgia. And now: they just wrapped up Coachella as the festival's EXCLUSIVE clothing apparel sponsor, with a pop-up called Hoodie House where festivalgoers could customize a limited-edition $100 Gap x Coachella hoodie on-site. Central Cee performed in custom Gap. KATSEYE dropped six individually-designed limited-edition hoodies timed to their Coachella debut, sold exclusively through Complex. And then THIS week, the Gap x Victoria Beckham collab dropped—38 pieces, prices starting at $38, almost certainly sold out by the time you're reading this.

 

The thing that's interesting to me isn't any one moment—it's the SYSTEM. Under creative director Zac Posen, Gap has been methodically rebuilding its cultural equity through music (Tyla, Troye Sivan, Young Miko, KATSEYE), designer collabs (Sandy Liang, Cult Gaia, Dôen, now VB), and IRL activations that give people something to actually FEEL. Instead of chasing trends, they're re-planting a flag on the thing they've always owned—the iconic American hoodie—and using culture to remind everyone why they cared in the first place.

 

I have a lot more thoughts on this one. We might need to dedicate a full issue to the Gap renaissance soon. 👀