Hi. I'm Jessica.
Welcome to the first Fair Winds.
I am one half of Son of a Sailor (Billy's every bit as chatty—I just happen to be the one sitting at the computer), and I've been wanting to write something like this for a long time.
I'm terrible at journaling. If you ask any of my friends, I'm much more likely to document life with a camera than a notebook. But lately I've realized there's a whole side of this business that never really makes it onto Instagram. The internet has become a place where we're all constantly making content, but not always saying much. I miss stories, context, and hearing how people got from point A to point B.
So that's what I'm hoping Fair Winds can be. A place to talk a little more deeply about design, craftsmanship, running a small business, finding balance, building community, and all of the little moments that shape this business but rarely make it into a Reel. Not a highlight reel, not a sales pitch—just the reality of what it looks like to build a creative life and business, one month at a time.
Fifteen years ago we had a company blog called Every of the Stuff (a play on All of the Things), which, in hindsight, was a pretty accurate reflection of how we've always approached running this business. We've always wanted to do everything, make everything, share everything, and somehow keep all of the balls in the air at once. Billy and I are both chronic over-explainers, so a monthly letter where I get to ramble a little honestly feels a lot more natural than trying to cram a month's worth of thoughts into a social media caption.
One thing I've spent an enormous amount of time doing lately is editing ourselves.
One of the strange side effects of being in business for fifteen years is that you slowly accumulate...well...a lot. of. stuff. We love color. We love options. We love saying, "Well, what if we made it in six more colors?" Unfortunately, after a decade and a half, that starts to snowball.
This spring, we went through nearly every product we make and asked ourselves whether it still feels like Son of a Sailor. We've added more longtime favorites to our Classics collection and retired a surprising number of designs altogether. Clearing space turns out to be a creative act all by itself.
We also worked with our photographer, Carly, to re-photograph everything we're keeping around. Our favorites deserved fresh glamour shots, and we're excited to re-energize some of our favorite work that we're still super in love with.
All of this distillation of our previous work has been very therapeutic. More importantly, it's made room for new work.
I've been quietly working on a collection that I'm overly excited about. It's inspired by vintage Norwegian fishing floats—those colorful glass buoys that once drifted alongside working fishing boats. I love that they were designed purely for utility, yet ended up becoming these beautiful little objects all on their own. We've paired hand-blown glass with forged wire to create pieces that feel architectural, organic, and colorful, and I genuinely think it's one of the most "Son of a Sailor" collections we've ever made. I've already sold one pair of prototype earrings to a friend and gifted another pair to another, and the feedback has me even more excited to get the whole shebang out into the world in just a couple of weeks!
Sneak peek below -- the rest will be unveiled over the next three weeks!
Billy has been doing much the same. He finally finished a wallet design that's been rattling around in his notebook for what feels like forever. We have pages and pages of ideas like that—things we've wanted to make but never seemed to have the uninterrupted design time to actually bring to life. I suspect that's the eternal struggle of anyone who makes things for a living.
Ironically, the thing that finally gave us that push was a deadline.
This August we're heading back to Shoppe Object in New York, our first trade show since before COVID. Before 2020, trade shows shaped our year. We'd build collections around them, pack up the booth, head to New York or Las Vegas, spend a few days talking with retailers from around the country, and come home exhausted but energized.
After Covid we just...weren't ready.
In the years since, we've moved our home, moved our business, built a new studio, learned a new city, and slowly figured out what this next version of Son of a Sailor looks like. There simply wasn't enough room, mentally or creatively, to jump back into wholesale in the way we wanted to. Also, to be completely honest, we were scared about investing that kind of money and time into trade shows again after being so battered and bruised from Covid. We survived, unlike many of our peers, but it has been hard. Unless you've been living under a rock for the past 6 years, you already understand.
Now, though, it feels different. We finally feel settled here in San Antonio—not just in our building, but in our neighborhood and our community. One of the most unexpected gifts of this move has been watching customers become friends. After losing our pup Bruce Willis in August, we were devastated a few weeks ago, when we had to say goodbye to his brother Clint Eastwood, our neighbors Matt & Sara and Michael showed up for us with such genuine kindness that it honestly caught us off guard. (Thanks, you guys.)
Those are the relationships we hoped we'd find when we moved here. The kind where the line between customer and neighbor starts to blur. Where people celebrate your wins, show up for your losses, and remind you that where you choose to build a business can become so much more than where you go to work.
Maybe that's why the creative energy has come rushing back.
We're still knee-deep in prototypes, product photography, booth planning, and a hundred tiny decisions that somehow always accompany a new collection, but for the first time in a while it all feels energizing instead of overwhelming. I'm excited to head back to New York with work that feels unmistakably like us, and even more excited to see what this next chapter holds.
My hope is that Fair Winds becomes a place where I can share more of the creative process, more behind the scenes, more of the conversations, tiny victories, and inevitable failures that never quite make it onto social media. Running a small business is messy and rewarding and occasionally absurd, and the people behind the work are just as much a part of Son of a Sailor as the things we make.
Thanks for reading the first one. I'm really glad you're here, and I can't wait to share more with you next month.
Fair winds and following seas,
