Hi!

You likely signed up for this after reading one of my essays on Medium, my personal website, or seeing something on X/Twitter. I send this thing every few months, mostly a wrap-up of stuff I’m working on and thinking about. There are always typos.

Now, to the newsletter…

Celebrating NYE by shooting off some roof fireworks,
a storied tradition like no other

I have sporadically done year-end reviews, but I don’t feel an urge to send one most years. I attribute this to the difference between “heads up” seasons and “heads down” seasons.

When you are in “heads up” season you are open to new ideas and uncertainty. You’re looking up to see where you should run next. Being in between jobs is usually a “heads up” season. So is crossing an age milestone, accomplishing a long held goal, suffering some sort of loss, or bracingly realizing that your life needs some shaking up.

And then there are “heads down” seasons. I like these seasons because you’re not wondering about alternative paths you could be walking. You don’t care, you have your head down building. If your life were a movie, this is where the montage happens. You’re going for it.

I feel most compelled to send an update when I’m shifting directions and about to head into heads down season. 

As you might have guessed, hi, hello that’s where I am. Let’s talk about it.

I guess this is a business.

In July 2024, I left my last full-time role as VP of Content at Crossbeam, which made 2025 my first full year in business as Gate Check Studios.

My personal goal was simple: make more than I made in my full time role.

My professional goal was to use the freedom to explore where the internet, content, and media were heading in the age of AI and build the next chapter of my career for the next platform shift.

As I close the books on 2025, I am pleased to report: mission accomplished on both fronts. 

If you were to look at my revenue chart, it appears like a smooth-ish upward slope. But there are hard lessons, embarrassing moments, and dumb mistakes contained in that journey.

Here’s what I’ve learned about the business and myself:

• Are you a business or a freelancer? When I ventured out on my own, some mentors advised me that it would take 1-3 years to even understand what my offer was. To start, my approach was to take meetings with CEOs and CMOs, ask them about their pain points and then suggest ways I could help. I would say “yes” to pretty much anything, which made me a freelance employee in all but name. That’s when I learned…
  

• I’m not a “generalist” marketer. I would see a problem that, say, an outbound sales motion would help. But knowing the next step and having the mastery to execute at a high level are different. I was humbled a few times trying to step outside of my sweet spot. Knowing what to do and being able to execute it as a world class level are different things. (Thats one of those things that is obvious to write but difficult to truly internalize). Which then begged the question: what, exactly, is my sweet spot? Why do people pay me? What do all my good clients have in common?  
  

• What makes a good client? What am I uniquely good at? After getting all clients through my professional network, I wanted to create a system or approach to my business to invite likeminded potential clients. What, exactly, is the thing I am offering? Figuring this out is one of the most difficult things I’ve done in my career. I haven't written publicly in nearly a year because I’ve been in the lab with a pen and a pad doing this.
  

• I was playing scared. After a decade-plus running at startup speed I was tired when I left Crossbeam and I thought I would be content to have a tiny one-man operation flying under the radar. I didn’t need to “be public”, I could just do good work. I thought that was humility talking, but it was fear. “Under the radar” meant any failures or bad ideas from me sailed by with little notice from the outside world. Being bold means proclaiming what your business is and what you stand for. I wasn’t doing that. I let the market come to me. In 2026, I will no longer do that.
  

• Friends are good. Under the banner Anthology, Nathalie Arbel, John Collins, and I have done some work together. It feels like the Avengers: we come together when we can’t accomplish the work solo. Nathalie and John have 15+ combined years as solo operators, so I’m privileged to get to work alongside them from time to time.
  

• AI, man. I haven't felt this optimistic and this invigorated about the internet since I first learned how to FTP files in 1998. The lessons compound and everything feels like magic. I use Claude Code on my local machine and it feels like I have four employees.

This year, I’m going for it. We’re in the midst of a once-in-a-generation platform shift and I want to see what Gate Check Studios can be.

The short version:

• My best clients are companies that are ready to play offense — to push into new markets, create a new category, or the next level of revenue.
  

• I build publishing and content systems that produce quality content at a scale that has a business impact.
  

• I distribute that content in a way that’s not dependent on the platforms. 
  

• My best clients are long-term thinkers and ready to invest in efforts that compound over time. Systems not campaigns. If you want to hit your leads quota next quarter, go hire a demand gen person. That’s not me. If you want to change the market’s perception of you + hit your revenue quota in the next 12 months, let’s talk.

I’ve narrowed my focus and messaging (see it here) and launched a new newsletter called Human Internet (if you are a subscriber to this list for content/media/discourse takes, you’ll like it!)

We moved!

You give me 3 minutes and Canva, and I’ll give you gold.

Don’t worry, I’m still in Philadelphia.

When my wife and I moved into Point Breeze (a neighborhood in South Philadelphia) in 2018 I often told people, “I’m retiring in this house and living here until I can’t get up the stairs.”

When we moved to Point Breeze in 2018, we had long-term goals but there were some things we couldn’t foresee. For example, how our careers would unfold, where various family members would live, COVID, and how many children we would eventually have (and thus how important schools and number of bedrooms would be.) In 2023, the answer was “two, final answer.”

I loved that house, that neighborhood, and that block - but some cracks started to show:

• We would befriend other young families who saw the area as their “starter house” and not their forever place and would promptly move out as soon as their kids got to school age. We went through this cycle a handful of times.

• We toured our local school and while I personally loved it, It was clear that most parents pulled their kids out for magnet, charter, or private options at a specific age. It wasn’t a long term option for community building.

• Much of our life started anchoring itself in our new neighborhood. Amenities, services, friends, schools: all there. I felt like every time I left the house I was walking the same route to the same area.

• We were lucky to snag a COVID-era interest rate, which made renting that house economically viable.

My goal in life is to never be in a school drop off / pick up car line. So we were not moving to the suburbs. 

I’d rather die.

With a load of mixed emotions we made the jump and moved a few neighborhoods over. While I sometimes curse leaving a very complete and lived-in home for a work-in-progress home, it was the best move for the things we cared about most: raising our children in a loving community of friends they can grow up with and adults that can look after them.

We can buy a new water heater more easily than we can line nearby blocks with kids the same age as ours. Also, somewhat selfishly, being able to walk to your office, your gym, your kids’ schools, your family, your favorite bars and restaurants, three parks, and your friends in less than 10 mins is pretty great.

As always, I’m long localism.

Smaller updates/thoughts:

• Getting my health in order. There’s a side of my family tree where no male has lived past 55. Turns out I have a genetic marker that leads to clogged arteries. After working with a preventative cardiologist, my heart metrics are in very healthy ranges and I have regular scans at one of the top hospitals in the country. Thank you, Penn!
  

• Polymarket obsessed, then disillusioned. I spent a few months obsessively tracking and following the prediction site Polymarket. But then, it became clear that it was yet another vehicle for fraud. Mainly, disputed markets (like this one) and insider trading (like this). Polymarket’s square bettors are effectively subsidizing a news service where insiders can trade on non-public information without fear of penalty. No thanks. 

  
  

• No more social media. After seeing how one’s likeness can be used with Grok or Sora, I’ve all but stopped using social media. I have an X account I use as a newsreader but the platforms are no longer social and are going to be a path to feeding AI models with our likeness. I couldn't, say, post pictures of my children after seeing that. Can you imagine turning 18 and knowing your likeness is already out of your control?
  

• Getting the writing bug again. I had become discouraged with writing and sharing ideas online. I would start to write something and get in my own head. Is this good? Does it help my business? I had to regain the love of writing not to be read, but to work through ideas.

It’s good to see you again, friend. Reply and tell me what you’re up to. Even if we’ve never met! 

- Sean

(Programming note: I’ve moved this mailing list to a new service after some deliverability issues, so if you’re getting this after not getting the past few, I'm sorry! Unsub here.)