There’s an old adage: "the cobbler’s children have no shoes." That is, the person with the skill to make and fix everyone else’s shoes never gets around to ensuring their own kids aren’t running around barefoot. Busy professionals who spend their expertise on clients and employers, and have nothing left over for the people closest to them.
I own a beach rental property called Barefoot Beach Club, which I remodeled from one large house into three separate condos. For more than three years, my day job has taken up my free time, and I left marketing, if you can call a filtered search on Airbnb "marketing", to listings that are hopefully found when someone is planning a trip to coastal North Carolina.
So when I experienced a recent layoff due to reorg, finally allowing me to sit down, scope a brand system, build an entire web presence, and position from scratch, the pun wasn’t lost on me. My kids got new shoes. On purpose. (The irony of the property address on Barefoot Lane, and being named after the location, wasn’t wasted on me either.)
Why vacation rentals are getting the full GTM treatment
Barefoot Beach Club is one house at Atlantic Beach, North Carolina, subdivided into three condos that can be booked individually or combined for a full buyout. Before I touched it, the entire online presence was a Linktree landing page that contained nothing more than a couple links pointing to the five Airbnb listings. Functional, forgettable, and doing none of the work a property with distinct booking configurations needs to get done. And it certainly wasn’t highlighting any of the local attractions on the island that makes up the Crystal Coast area.
I didn’t rebuild it because the business demanded it at any urgent scale. I rebuilt it because I had the skill sitting idle, and idle skill is a waste I don’t tolerate well, professionally or otherwise.
The result is a full five-page static site with its own visual identity, distinct from anything on my professional brand work, built around the actual guest decision tree: which condo, what configuration, what season, what’s nearby. I was careful about language that matters more than it seems like it should. Each unit gets called a condo, never a cottage or a house, because "the house" only ever refers to all three units together as the Entire Club. That kind of precision is a small thing until a guest books the wrong configuration and the whole reservation becomes a mess to untangle.
The unglamorous parts are still the parts that matter
None of this was flashy. It was the same instinct I bring to a cybersecurity GTM stack: nail the taxonomy before you touch the design, get the language guests actually search for, make sure the off-season doesn’t just go dark. Barefoot Beach Club routes to a Zillow listing in the off-season instead of leaving stale content up on a dead page. Contact currently runs through a mailto placeholder until I build out real booking infrastructure, which is intentional sequencing, not an oversight. I didn’t promise "book direct" language until direct booking actually exists. Overpromising on a five-page rental site is still overpromising.
Why I keep doing this while I’m job hunting
I’m in an active search for a VP of Marketing or CMO role at a pre-IPO cybersecurity company right now. It would be reasonable to assume a beach rental site is a distraction from that. It’s the opposite.
Every skill that goes into building Barefoot Beach Club, information architecture, positioning, brand systems, conversion-minded copy, SEO structure, is the same skill I’d bring to a demand gen function or a category launch. The stakes are different. The muscle is identical. When there’s downtime in a search, and there always is, I don’t let it sit empty. I point it at something real, with real guests and a real booking calendar, so the skill stays sharp instead of theoretical.
It’s also just honest positioning. I don’t hide the fact that I own this property, and rent it when I’m not there to offset the mortgage costs. A GTM leader who can architect go-to-market for enterprise security software and also run positioning, brand, and booking strategy for a hospitality property isn’t diluting focus. That’s the same operator instinct applied to two different markets, and if anything it’s a more current, hands-on proof point than a case study from two roles ago.
Work in progress, on purpose
Barefoot Beach Club isn’t finished. The booking backend isn’t built yet. The listing pages are thin. There’s more to do than what’s live. I’m fine with that, because it’s not supposed to be finished. It’s supposed to be moving, the same way any GTM motion worth running is always moving, iterating, and getting sharper with the next round.
The cobbler’s kids got new shoes because I refused to let the one business that’s entirely mine be the one thing I didn’t bother applying my own craft to. Everything else I’m building right now, the diagnostic tool, the job search radar, the next role I’m walking into, runs on the same principle.