
Alright friends -
Things have been a bit crazy over here.
Update 1: Rebuilding a town takes a lot of work… I’ve been meeting with tenants, bankers, engineers, legal eagles, interior designers, architects, town inspectors, general contractors, and a long list of subcontractors that seemingly go on forever. We’re currently flat out, racing to button up the buildings, install septic, and insulate before winter — our goal is to get some staff housing open for January 1st (push, push, push).
It’s been incredible to watch this project come together over the past few years and it finally feels like rubber has hit the road. I’ll put together a letter where I deep dive further into the project and long term vision another day.
Update 2: I recently returned from Durham where I was entrusted with a microphone to speak about the future of local media at Local News Camp — spoiler: I’m insanely optimistic. My goal was to shatter the antiquated beliefs of what the term local media even means, let alone what types of businesses we can build within that industry… all while wearing crocs with socks.

Update 3: For my local friends, come by the Autumn Howl event tomorrow 10/24. The weather will be grand and I’ll buy you a beer or three. Plus we got a cash prize for a steinholding competition → details
Alright time to get down to brass tacks. I want to share a bit more about PREMIUM SUBSCRIPTIONS and hopefully you’ll walk away in a few minutes with a broader imagination of what’s possible and how with the right execution you can expand your business offering and generate more revenue for your business.
The current state of Premium Subscriptions is incredibly underwhelming.
I don’t want a mug with your logo on it. I don’t want a birthday shoutout. Perhaps the paywalled article is good, but that’s not always the case.
So as I’ve thought long and hard about what a Premium Subscription looks like for Catskill Crew — I’ve challenged myself to create something worthy enough that it would get even a tough nut like myself to open their wallet and type in the credit card number.
What I have ended up with is a new experiment for my business — and if executed properly will enhance the offering, generate 6-figures in recurring revenue, with additional streams off that main artery.
My goal for Y1 is $120,000 in ARR purely from membership.
Let’s break it down.

Ignore the jankiness of this here gif
As of this week, Catskill Crew has officially launched the Crew Club — my take on a Premium Subscription.
Let’s start with what the Crew Club IS NOT.
The Crew Club is not a paywall.
Joining does not grant you access to gated articles. And while that is the reality for most media companies, that does not interest me in the slightest and most importantly, it would be a fast path to a cataclysmic burn out.
Trying to provide just enough value for the freemium readers to continue returning and tease just enough for them to upgrade, meanwhile ensuring the gated content is differentiated enough to justify the cost of premium.
Woof. Not for me. But perhaps that’s for you.
Now let’s talk about what the Crew Club IS.

It is the foundation for a new chapter for my local media company, and ideally a new revenue and value generator for the business.
This may fail dramatically. Or it may require subtle adjustments. Or it may be a wild success straight out the gate and within 365 days it will be generating hundreds of thousands of dollars in new revenue. Time shall tell.
At launch, the Crew Club costs $10/mo and has several value props (beyond just “supporting local media”) — while I intend to grow from here — let’s examine what exists today.
GAMES & LEADERBOARDS
Once you sign up and log in as a premium Crew Club Member, you get access to daily games - these range from Crossword puzzles, W?rds, Trivia, and River Legends.
The system is completely customized with logic sourcing, ability to weigh topics, and an automated system that generates and publishes games every-single-day.
Each game has a daily and monthly leaderboard — and there are plans to add more games as time goes on.
People like games. Heck, how much revenue does NYT generate because of wordle alone… Well, Catskill Crew now has our own version.
More games in the works. More fun in the pipeline. Each game is another offering I can point to in the main newsletter to drive more sign ups.
MERCH & PRODUCTS
Crew Club Members unlock access to exclusive merch and products.
At the moment, there is a limited edition hoodie and tech-dad-cap. These are listed on the store, but without being a premium member, there is no buy button.
Some products will be exclusive for the Crew Club for a set period of time before going out to the general public — others are perma-exclusive.

When a new product launches, I will absolutely be promoting that in the newsletter in order to drive more sign ups for the Club.
There is already early validation for the exclusive product offers as several readers have signed up and instantly made a product purchase — thus driving more revenue, and deepening their relationship with the brand.
EVENTS
I have plans to launch a limited series of events that are private for Crew Club Members — however, putting any barrier around friendship is a pretty crap move — so this will be light.
Some events will cost money. Others will be free. Speaking of…
FREEBIES
I have plans in the works and products already arriving that will be free for claim by Crew Club Members.
These will be fun little doodads (wow, that’s how you spell that word, huh?) that I will also promote in the newsletter and within the premium page.
These could be stickers, art prints, photographs, hats — who knows what else.
The first will be these sweet bumper stickers.

Some freebies will be run in limited quantities and designed for first to claim while others will be for all.
FUTURE PLANS
There are several new features in the works including a points system to gamify memberships — but I have more experimentation to run with Phase 1 prior to deploying these new features.
So that’s it. That’s my premium offering. It circumvents the trad-paywall model to create something new and unique.
It also generates new revenue streams for exclusive merch, products, and events. Maybe in time, game upgrades.
Anything is possible.
OK well, I have to run, because I need to give a tour to a prospective restaurateur for one of the buildings and then meet 6 brewers who are coming to the Catskills for the Autumn Howl event.
Take care. Reach out anytime. Stay creative and keep having fun.
Nuggets
Currently reading A Pattern Language it’s extremely dense but fascinating.
New ballpoint pen the ZENTO Signature Model .38mm this one.
Rewatching Lister’s greatest birding film of all time — if you haven’t watched it, fix that roll the film.
I wrote this entire letter to you listening to the OG Morrowind Soundtrack listen here.

The view from the bar I’m building
Want to launch or level up your local newsletter?
Join over 300 founders and come build with us.


