I think “brand commentary” as a growth mechanism is overplayed. In general, I believe brands — especially media companies — should keep doing the work. As a consumer, I don’t really care what was hard for Mr. Founder. Keep moving. Spare me the Spotify Wrapped, or the emotional video with a fuzzy RØDE mic and a dead-pan stare titled “I Have a Confession.”
That said, I know a lot of people reading this are a bit less cynical than I am (slightly) and genuinely want to see under the hood. So as we ring in the new year, let’s take a quick look at what happened in 2025 — because a lot did — and while we’re here, let’s look ahead to 2026. If nothing else, it keeps me accountable.
I present to you a brief hiatus from Need, Wrote, Ate and instead…
Did, Didn’t, Doing.
Next Sunday, we’re right back to business.
DID
Weekly Newsletter
This whole thing really started as a New Year’s resolution: every Sunday, I would write to you. No layups, no half-assing — genuine, value-add pieces.
Between breakups, a broken knee, ADD, a full-time job, and the occasional hangover, some Sundays were harder than others — but nothing has brought me more real happiness than writing this newsletter. It’s been therapeutic through the good, the bad, and the ugly.
As of today, we’re at 929 subscribers, up a couple hundred since September. I like our odds of hitting 1,000 early in 2026.
Folded In Three Full-Time Writers
Hey
Hey
Hey
Alongside a handful of guest contributors, these three consistently brought thoughtful pieces aligned with the brand — and real excitement for what we’re building. I feel indebted to them, and I hope Outpost continues to be a stage where they (and others) can grow and build their own personal brands.
In 2026 we’re doubling down. If you’re a writer, musician, videographer, creator, designer — or something I haven’t even thought of — email info@outpostnyc.co. We’re building infrastructure to raise all ships.
Launched Outpostnyc.co
Our biggest push in 2025: launching the website.
I’ve always believed we need a true home base outside the newsletter — a place to build a catalog of media, curated products, and events. I built it myself. It was frustrating. Many late nights yelling at ChatGPT, pretending to be a coder.
The goal was simple: get it to a point where people could say, “Okay — I get it.” Functionally, it still needs work. The good news: I’m meeting with a friend — one of the best web designers I’ve ever met — the first week of 2026. We’ll make it foundational to the brand.
Hats
After countless trips to an embroider in china town who yells at me every time I give him business (but I think likes me?) we made hats and everyone seemed to want one. Most annual subscribers now have theirs.
A few are still outstanding — I’m sorry. Top two priorities on January 1:
Hats
Clean up the website.
In that order.
Hosted a Launch Party & Caroling Party
Events are in our DNA. Many of you first knew Outpost when it was Conte Supper Club. That spirit remains.
We started with a friends-and-family launch party, followed by a caroling party we pulled together in four days. Outpost subsidized some decor, port, champagne, and little extras — but most of it came from people genuinely wanting to show up and buy tickets. I’m incredibly grateful.
Expect more next year.
Cleaned Up the Brand
Thanks to our wonderful graphic designer Wylee Musnicki, real visual identity started to take shape. We graduated from Canva chaos to thoughtful, legit design — and introduced some fun new elements along the way.
Expect more refinement in 2026.
DIDN’T
Weekly Interviews
My first misstep: promising weekly interviews.
Two things happened:
I underestimated how hard it would be to lock people down — even for free publicity. Busy schedules, polite declines — it surprised me.
I wasn’t sure whether it should be a separate Wednesday email or folded into Sunday.
Decision: one Sunday email — including interviews, recipes, videos, and contributor work. Cleaner, stronger, better.
Stowe Train, London Garden Party, Black Tie Soirée
Back in August, I promised these. They’re still happening — just not yet. Building the media side took more energy than expected.
The good news:
A London party will happen — it’s a matter of timing.
I signed the contract for a Black Tie dinner at The Explorers Club: Thursday, February 17. Mend your tux, steam your gown, mark your calendars.
The train hurt the most. I love the romance of old ski cars leaving Grand Central for weekend adventures. I spent August on weekly calls, inspected an actual train car, and briefly thought Outpost might become a rail company. But I couldn’t justify charging $1,000 for an experience that wasn’t good enough — yet.
I met the right people, though. It’s not dead. Hold me to it next winter.
Overall? I genuinely think we accomplished nearly everything we set out to do.
DOING
I’ll keep this short — partly because we’re running long, and partly because I don’t want to show all the cards. But here’s a taste:
Exclusive Outpost products – Canvas carry bags, umbrellas, a tuxedo collab. When we find brands that make things we want to use, we’ll promote them. When we can’t find something — why don’t we just do it ourselves?
Job postings – A place for young New Yorkers to find quality opportunities and for companies to find quality talent.
Music – Music is a big part of my life, and I want to find more meaningful ways to promote talented artists.
Sunday lunches – Toying with the idea of more Sunday events at restaurants and venues I love, on a day that I love.
Weekly interviews – Just adding this again to keep myself accountable.
An annual hardcover edition of Outpost – I’ve teamed up with the wonderful , who is building out the first edition of our physical edition.
Interior design – A talented designer reached out before break — I want to find a way to fold her in. Stay tuned.
More guides and product picks – Because affiliate + brand partners is the engine that funds all of this.
That’s all for now. I am leaving for the airport in 15 minutes to ring in the New Year in the Cotswolds after being snowed in for two days back in Connecticut.
I’ll leave you with this: while exhausting at times, building Outpost brings me so much joy. Writing, putting out content, and building a stage to promote other like-minded people is rewarding to no end.
The support and kindness I’ve been shown in 2025 — after just four months of launching Outpost — has been mind-blowing. It’s easy to look elsewhere and think there’s more that can be done — more content, more subscribers, more paid media — but when it’s all said and done, I’m really proud of what we’ve accomplished so far.
And it’s only the beginning.
Cheers,
