Dispatches from the Long Game

Howdy friend!

Welcome to Dispatches from the Long Game, a radically transparent newsletter for entrepreneurial creators. Every now and again, I pull back the curtain and share everything—good, bad, and ugly—about how I’m building Ungated Media into a business I’ll love for years, or decades, to come.

If you’re new here, my big experiment in 2021 is working in seven-week cycles, then taking the eighth week off. The goal is partly to beat burnout (which isn’t going great, tbh), but also to work in discreet chunks, where I can run self-contained experiments, and see how they go.

Anyhow, today is the first day of my third cycle. I’ve been off the grid for the last week, resting and rejuvenating, and I’m ready for action!

So this post will be a thorough recap of how my business did from from February 21st to April 11th. I’ll share my numbers, my wins, challenges, and next steps.

But first, here are some things that delighted me during the week off.

Book: Friendly Ambitious Nerd by Visakan Veerasamy.
Course: Linking Your Thinking by Nick Milo. I spent most of my sabbatical gleefully working through and implementing this course, and it is so freakin’ good. My PKM system is finally turning into something valuable and sustainable after years of struggling to make BASB and Zettelkasten work.
Album: Roll The Bones X by Shakey Graves. This is a 10-year reissue of my most-listened to album ever, which makes me feel old. My favorite song is probably Business Lunch, or his cover of Springsteen’s I’m on Fire.
Show: Billions. Holy moly, this is a solid, dark show. There are no good guys here, yet you somehow still root for them all.
Coffee: Sermon from Verve Coffee Roasters. It’s like drinking a cup of blueberry pie.

Alrighty. Now here’s my deep dive into how the last seven weeks went in Ungated land.

Business Health Checkup - The 20,000 Foot View

Articles published: 7 (6 free, 1 premium). The goal was 7 free, 7 premium, so definitely fell a bit short on that one 😂
Traffic: 5.1K site views from 1.8K visitors. This is a tiny uptick from the previous update. Yet it’s still virtually identical to both December 2020, and February of 2021. To be fair, I’ve hardly promoted myself at all, and an increasing portion of this is from SEO, which pleases me.
Total email subscribers: 221 (+62%)
Total paid members: 60 - 56 lifetime, 4 annual (+44%)
Churned members: 0 (still too early to tell, but I just made the membership way more valuable, so fingers crossed that churn will be super low next year!)
New Coaching/Consulting Clients: 1 (I’m still working with the 8 from last cycle, so this is plenty enough for me)
Net revenue: $7249 (+73%)
Expenses: $512 (The biggest expense this time was paying for a year up front of Ghost Pro, and moving away from my much cheaper, but unreliable, self-hosted install.)
Profit: $6737 (Not too shabby for seven weeks of work, especially given how new this business still is)
Morale: 8/10

Wins to Celebrate

Consolidation of brands and radical simplicity

Far and away, the biggest win of this cycle was bringing Ungated and Filmmaker Freedom (my first business) closer together. I’m starting to consolidate these brands in a way that makes my online life simpler, and frees up energy to create new stuff and interact with my peeps.

My biggest move so far has been merging the Ungated community (which used to live in Circle) into Mighty Networks.

I’ve been running a community for indie filmmakers in MN for the last three years. Since it was already geared around entrepreneurship and marketing, it made sense to bring in other types of creators as well.

The whole thing has been rebranded into the Ungated Collective, and I’m freakin’ stoked about it. I wrote more about that decision in this article, but the biggest takeaway is that I now have one kick-ass community that I love instead of two mediocre ones that I feel perpetually guilty about not spending enough time in.

Also, even though Mighty Networks isn’t nearly as clean/intuitive as Circle, its built-in course functionality is really good. So now, I don’t need a third party course platform. All of my courses and community live inside Mighty Networks, as do all the membership benefits for Ungated.

I can’t stress how big of a win this was. Talk about killing multiple birds with one stone, and keeping things radically simple.

But wait, there’s more!

To take this a step further, my next project is to merge the Filmmaker Freedom and Ungated email lists together.

Like the communities, I’ve been slacking on my newsletters and email marketing because I’ve felt stretched thin. For those of you who know me, you know authentic email marketing is MY JAM. So it’s been killing me to basically ignore these lists I’ve worked so hard to build.

Once I merge them, however, I’ll have more space and energy to do what I love, which is creating an ecosystem of delightful rabbit holes to brighten up your inbox.

This also means the Ungated email list will go from 221 subscribers to somewhere around 5200 in the course of 10 minutes. Take that, growth hackers! 😂

Now, the actual merge is probably going to suck. The Filmmaker Freedom list needs some major cleanup. There are all sorts of sequences and automations and tags and custom fields and segments that I’m never going to use again. Plus, I have to figure out how to handle the overlapping subscribers and make sure they’re still segmented properly. All of this will be tedious, and not particularly fun.

And finally, before I do the merge, I’ll have to make sure the Filmmaker Freedom peeps know that the list is no longer explicitly about filmmaking, but creative entrepreneurship and marketing. So I suspect I’ll have a substantial chunk of unsubscribes when I make that announcement. But that’s ok. Because I can’t serve those people well anyway.

So yeah, that’s where I’m at. It’s been a lot of logistical, behind the scenes work. But I’m stoked for the energy if frees up.

One community instead of two. One email list instead of two. Quality over quantity. Radical simplicity.

Since the beginning of the year, I’ve been woefully inconsistent with my side project, Citizen Within. Up until a few weeks ago, I’d only published a few pieces, and only when I felt like it. There was no consistency, and no commitment.

That bugs me, partly because I know Citizen Within can play a role in healing the political landscape, but also because I want it to be a case study for Ungated. I want to show how I’m using principles like NicheCraft and the Identity Theorem to build a business in a niche totally separate from the “teaching creators how to create” space.

Anyhow, I’ve known for awhile that I needed to jumpstart my creative process and truly commit to Citizen Within. But every time I sat down to write, I got so wrapped up my head, and stuck in the mire of imposter syndrome, that I couldn’t ship anything.

So I hired a coach. His name is Michael Ashcroft, and he’s helping me stop overthinking, ship new creative work consistently, and (wait for it) actually ENJOY myself during the process.

It’s crazy how my analytical brain, so full of useful strategies and good intentions, can be such a hindrance when it comes to creating and shipping new work.

Working with Michael has been great so far. We’ve been focusing in on some of the internal stories preventing me from creating consistently for Citizen Within, and exploring how it would look/feel to do the work for its own sake. And lemme tell you, that’s been insanely helpful.

From there, I decided to make a real, ongoing commitment to Citizen Within, starting with a weekly newsletter called No Easy Answers. Every Saturday morning for the next year, I’ll be curating a handful of stories to help others (but mostly myself) think more deeply about the issues of the day, and make sense of a nutty world.

I have big plans for Citizen Within, and I suspect that in a year or three, it’ll look substantially different. But I know this small, humble commitment is the perfect way to lay a strong foundation without overwhelming myself.

So that’s a major win in my book.

Settled into the long game, and honed my positioning

Like most creators in the early days of a new venture, I often feel anxious about how slow everything is. I want my list and revenue to be growing way faster than they are, and I feel like a failure when it doesn’t happen.

But I had a bit of a breakthrough on that front over the last seven weeks.

I realized it’s ok to take it slow and steady. It’s ok to chip away at your goals, even when the world around you is like 10X YOUR BIZ RIGHT NOW OR YOU SUCK. It’s hard to tune that stuff out and not let it effect you. But I’ve been getting a lot better at it.

More specifically, I’ve been better at noticing those feelings of anxiety and failure, disconnecting from them, and reminding myself that I’m playing the long game with Ungated. I don’t need it to be spitting out cash right away. I can continue building relationships and assets, even if on the surface, it looks like nothing’s happening.

While everyone else is zipping around being obsessed with NFTs, cohort-based courses, and 10x-ing their twitter following, I’m perfectly happy to sit back and keep chipping away at my vision, even if it’s not immediately sexy or trendy.

How is any of this translating into reality? For one, I’ve stopped trying to use twitter to “build an audience.” Instead, I’m just there to have fun, make friends, and help where I can. Few things are as important to the long game as strong relationships, and actually enjoying yourself. So making that shift on twitter has really lightened my spirits, and helped me avoid anxiety traps.

The second big breakthrough I had here was with the positioning/differentiation for Ungated. After all, there are literally eleventy million creators in the “creating for other creators” space. (It’s very reminiscent of the bullshit industrial complex.)

Anyhow, I’ve always positioned myself against the hordes of gurus who promise the “secrets” of online success and 10x audience growth and all that shit. I’m the opposite of those clowns in every conceivable way. But I’m always looking to put a finer point on who I serve.

In that vein, I’m now explicitly for “creators who want to play the long game of business.” That was always implied in the goal of making 1,000 True Fans a reality for more people, but now I’m putting the “long game” idea front and center.

For me, this is a filtering mechanism. I want to repel people who are only interested in short-term value extraction. I want to drive away the growth hackers, the “creator economy” bandwagon folks, and the people who think their newsletter will make them rich overnight. I can’t help them, nor do I want to.

My people are the ones who have meaningful creative work inside them, and a desire to still be doing that work, in a sustainable way, for the next ten or twenty years.

So getting clarity on that, and weaving it into my messaging, has felt good and aligned. I’m getting closer and closer to the old Seth Godin adage of “find the others.”

Challenges

Learned a hard, but obvious lesson. You get what you pay for.

I don’t know about you, but I love saving money. It makes me feel smart and sophisticated.

But during my year of radical simplicity, my attempts to save money have made my life more complicated.

In December, I moved Ungated from Webflow to Ghost. That was a fantastic decision. But instead of paying for the official version of Ghost and forgetting about it, I opted to do a self-hosted install on Digital Ocean. Instead of $29/month, I was paying $5.

Now here’s the problem. The Ungated site went down 4-5 times in from January to March. Like, totally offline. And I, as a technologically illiterate person, couldn’t do a damn thing to solve the problem myself, or prevent it from happening again.

That kind of nonsense just isn’t worth the money I was saving. It gave me a constant sense of low-level anxiety, and when it happened, it pulled me away from meaningful creative work.

So, when Ghost released version 4.0 of its platform, I bit the bullet and ponied up for the Pro version that’s hosted by them. It took some time to migrate my old site over and make sure everything worked properly. But now, I don’t have to think about those stupid crashes anymore.

And I learned an important lesson. If you value simplicity and peace of mind, it’s worth paying extra for.

A quickie launch that didn’t quite meet expectations

You know that email list of 5K subs I mentioned earlier? It’s from Filmmaker Freedom. I’ve been working on it for years, with a focus on building relationships and offering great entrepreneurial content.

I figured it was about time to share what I’ve been up to with Ungated, and let them in on the ground floor of the new venture. So I did a very quick, but compelling launch offer on the Ungated Lifetime Membership that I thought they’d be stoked for.

(Narrator: They weren’t particularly stoked)

When it was all over, I’d made 21 sales on a $200 product. Don’t get me wrong, that’s real money. And I’m happy with it. But given the list size, and the strength of the offer, I was expecting somewhere in the neighborhood of 40-50 sales.

Honestly, I think there are a handful of factors contributing to this somewhat disappointing launch.

Most of my true fans from Filmmaker Freedom knew about Ungated and were already paid members. Honestly, had those fans not already been Ungated customers, I’m certain this launch would have been much larger.
The offer wasn’t explicitly for indie filmmakers, so it likely didn’t resonate with this list as it would for a broader range of “creators.”
It’s been a solid five months since I broadcasted to this list. There are a couple of sequences and a shadow newsletter working in the background, but the vast majority of subs haven’t heard from me in awhile. Honestly, it was probably jarring (and bad form on my part) to jump straight into daily content and a launch like that. I had about 120 unsubscribes over five days.
I dramatically undersold the value of this thing. Just the Accelerator course is worth $400, at least. And lifetime group coaching with me? Other folks would charge $5k for that shit. Not to mention lifetime access to all the courses and workshops I’m creating in the future. Part of me feels like I should have emphasized this value way more, but I have such an aversion to being perceived as hype-y or manipulative.

All in all, this wasn’t really a loss or a challenge. It just felt that way at the time. Now that I’m writing about it, I can see where my expectations didn’t quite make sense.

Worked my ass off to ship a course and made…. 2 sales

During my second cycle, I finally finished the Find Your Niche course, and quietly rolled it out. This thing took two solid months of work, and it’s really freakin’ good.

But somewhere along the way, I had a realization. I don’t want to make big, precisely-structured courses like this anymore. Hell, my flagship course for Filmmaker Freedom, the Audience Accelerator, took ten months to finish. These kinds of projects just bring out the worst of my perfectionist tendencies.

What I really want is to kick perfectionism to the curb, and ship A TON of educational goodies for my members. My hope is the library grows quickly, and it becomes a fun a choose-your-own-adventure kind of thing. No matter where someone is in their creator journey, I hope to have some quality training to help them solve problems and move forward.

So, for the foreseeable future, I’m going to be focusing on quick and dirty workshops instead of big fancy courses. I’m going to pull together my best strategies on one crunchy topic at a time, record the workshop live, then add the recording to my vault. Lather, rinse, repeat.

This year, I’ll be doing workshops on positioning, market research, email marketing, content promotion, online personas, curation, and more.

As for that bit about only selling two copies of Find Your Niche, I suspect that’s because I didn’t promote it, outside of writing an article that basically gave the course’s ideas away for free. 😂

It also doesn’t help that these courses/workshops are included in membership, so that means there’s very little incentive to buy them individually.

By the way, if you’re sick of hearing “find your niche” and you actually want to do it, boy howdy will this course rock your world. If you’re reading this right now, you’re a paid member and already have access to it. So jump into the community and sign up from the membership hub.

Internal challenges around creating and promoting

My giant article about how to niche down was 80% done for six straight weeks. Getting it across the finish line was excruciating.

I’m also working on another giant article about why the concept of a “personal monopoly” is alluring, but ultimately unhelpful if your goal is to build a business. I worry about whether that one will ever see the light of day.

And when you factor in all the things I’ve written, but haven’t shared yet, it’s honestly staggering that I’m getting any real traffic at all.

Frankly, it never ceases to amaze me how much resistance I feel when it comes to creating original stuff and promoting myself. Even after eight years in the trenches of online writing and business, the resistance gets the better of me all the damn time.

Like, I know how to create world-class content. I know how be an effective, delightful marketer. I know how to attract and engage and build trust. I have the knowledge.

But none of that changes the fact that good work and ethical marketing are an act of vulnerability. You’re putting yourself out there, and making yourself seen. And that shit is scary. At least for me.

That’s a big part of why I hired Michael Ashcroft, who I mentioned earlier. I have no qualms about paying for a coach anymore, especially during times like these when I’m massively in my own way. So Michael’s been helping me cut through the bullshit stories I’ve got going on in my head, and get back to having fun again.

There’s also some intriguing metaphysical shit at play here. When I’m all caught up in my head, and when I try to force it, my content and marketing and products are worse. But when I’m having fun, and letting the work flow through me, it shines through in the finished product, and attracts more fun people into my world. It’s like magic.

So yeah, I’m working on these things with Michael. Day by day, I’m becoming less of a tightly-wound brainiac who can’t stop overthinking everything, and more of a borderline fun human person. 😂

What’s next

Ok, so that’s a pretty solid rundown of where I’ve been these last two months. Here’s what I’m hoping to get done in the coming cycle.

Merge the Filmmaker Freedom and Ungated email lists.
Create new onboarding for the Ungated Collective community.
Flesh out the “True Fan Fundamentals” series, and turn it into an email course.
Keep writing and publishing articles in the “Adventures in NicheCraft” series.
Publish several new case-studies from my clients, as well as one for Citizen Within.
Run a paid workshop and add the recording to the membership. I’m leaning towards doing the workshop on positioning.

If you’ve made it this far, thanks for reading. Hope you got something out of it, and I’ll see y’all in the community!

-Rob