It’s been a little over four years since I made a go at turning this newsletter into a full-time gig, and from the very beginning I assumed that I’d be publishing regular dispatches about my progress. After all, the entire focus of this project is to make media entrepreneurs better at their jobs, and what better way to do that than to share the insights from my own journey?

And for the first few years I did bang out these self-reflective missives on a semi-regular basis. I wrote about how I structure my workweek, the different ways I optimize my newsletter, and the gritty reality for Substack’s “middle class.” My audience really seemed to like these pieces, as evidenced by the fact that they often attracted more shares than average. And I received a lot of value from them as well, as they gave me the opportunity to stop and think more deeply about the lessons I’d learned in the previous months.

But then something changed. I started publishing these pieces less and less often. At first, I’d check in on the business roughly once every six months. Then it turned into an end-of-year tradition. But when 2024 came around I couldn’t muster the energy to write one. The excitement I used to derive from penning these pieces was completely gone, and even the thought of doing so filled me with dread.

Why? Because at a certain point in 2023 I really started to realize how little I actually knew about running a successful media business. This might sound strange coming from a guy who spends 50+ hours a week writing and podcasting about media operators, but if there’s one thing I’ve learned from interviewing 200+ successful content entrepreneurs, it’s that no two success stories are the same; I couldn’t simply copy and paste someone else’s playbook and expect to see identical results.

By December 2023, I finally admitted to myself that many of the assumptions I’d made about my own media business were completely wrong and that my revenue growth had stalled out. Actually, if I’m being honest with myself, it had started to backslide, which was a pretty horrific prospect for someone who was still so far away from his ultimate goal.

Was that revelation depressing? Sure, a little. But it also came as a bit of relief since it forced me to cast aside what I thought I knew about my business and think comprehensively about a new strategy. In January, I opened up a Google Doc and began writing a stream-of-consciousness screed that gradually spanned into thousands of words. The document analyzed my past failures and attempted to pinpoint my differentiated skill sets. From there, I began to map out a business strategy that actually aligns with my core strengths as a content creator. 

Four months later, I feel like I’ve settled on a strategy that caters to those strengths and is actually sustainable. I want to outline that strategy in detail, but first I think it might be helpful to talk a little bit more about all the mistakes that led up to that late 2023 revelation.

A winding road of bad assumptions

People often ask me when I launched my newsletter, and I usually tell them that it was in early 2020, but that isn’t completely true. That’s when I launched the paid version of my newsletter.

I actually debuted the free edition in 2014, though it looked nothing like it does today. I had recently left my full-time office job to run my own content marketing consultancy. In an effort to find clients, I poured all my available free time into writing longform articles for Medium. Over a period of several years I wrote profiles of media operators at mainstream outlets and interviewed founders of successful media startups. Some of these pieces did extremely well, and I racked up over 14,000 followers on Medium. What’s more, these articles served as an excellent calling card for potential clients, and within a short period of time several companies were paying me monthly retainers to run their own content strategies.

This was around the same time that personal newsletters were starting to take off, and there was this burgeoning industry discussion about the importance of “owning” your audience. That’s how I ended up launching on Tinyletter in 2014. To grow it, I placed a call-to-action in the middle of my Medium articles that encouraged readers to sign up, and they did so in dribs and drabs.

For the first six years of the newsletter’s existence, it was little more than a link roundup — a way to send my small audience to articles I was publishing elsewhere. But in the back of my mind I always knew I wanted to turn it into its own media business. I’d watched the rise of Ben Thompson’s Stratechery with keen interest, and I understood early on that Substack would be a game changer for the feasibility of such businesses. The question was not if I’d pursue a solo media career, but when.

And then in early 2020, I got my chance. The pandemic hit, and we had those few months of limbo when no one knew whether the economy would collapse. As a precautionary measure, almost all of my consulting clients put a pause on freelance work. I suddenly had a lot of free time on my hands, and so I announced to my audience that they could now support my work with a paid subscription. By the time those consulting clients came crawling back a few months later, I was too committed to this new career. I turned them all down.

Now, anyone launching a paid product will tell you that you need to clearly define what the product is so potential customers can make an adequate assessment of whether they want to purchase it. But I only had around 1,000 free subscribers at that point, and I knew that I needed way more than that to achieve the kind of critical mass that would sustain a business. I didn’t want to tie my hand behind my back by announcing all sorts of paid benefits that would take me away from creating the free content that would help grow my audience.

So I was intentionally vague about what a paid subscription would actually get you. For the first two years or so, I basically operated it as a patronage model wherein people mainly subscribed to financially support my work. Sure, I occasionally sent out paid newsletters and other perks, but for the most part I just tried to use “guilt” messaging to drive paid conversions. As you can imagine, this didn’t actually perform all that well, and the readers who did subscribe ended up churning at a relatively high rate.

Did this approach hinder my revenue growth? Almost certainly. But it also allowed me to focus on expanding my audience, and by early 2022 I was achieving some real momentum on that front. Not only was my email list steadily building, but I was attracting the right kinds of readers — top executives who worked in media, marketing, and tech. Whereas before it was an uphill battle to get people to share my stuff, I had now reached a point where almost every newsletter was widely promulgated on Twitter and other platforms.

And then in March 2022, Substack threw gasoline on the fire when it debuted its Recommendations tool. Because I wrote so much about the business of newsletters, several top Substack writers were big fans of my work and had added me to their recommended lists. Within a period of just a few months, my free list grew from 4,000 to over 10,000. I was approaching the critical mass I needed to build a sustainable business.

It was at this point that I should have started focusing on designing a well-defined subscription offering, but I got distracted by an entirely new line of business. In 2020, the only viable path for a solo writing career was through paid subscriptions, but by 2022 a growing number of Substack writers were beginning to diversify their revenue by selling sponsorships. Some had even eschewed subscriptions and built six figure businesses through sponsorships alone.

I was starting to receive emails from businesses inquiring about my sponsorship rates, and so, almost on a whim, I put together a media kit and sent out a newsletter announcing that I was open for business. Within a relatively short period of time, I had sold out several months of ad slots, and I eventually sold out all my inventory for 2022.

It was a “holy shit” moment where I doubled my revenue virtually overnight. Suddenly, it didn’t seem so far-fetched that subscriptions could remain a relatively small part of my business while ads brought in the bulk of the revenue. So instead of focusing on building out a comprehensive subscription offering, I instead doubled down on the free content that would help me grow my audience, since a larger email list would allow me to charge more to advertisers.

By the end of 2022, I was feeling pretty good about myself. My email list had more than doubled that year, and I was seeing plenty of inbound demand for sponsorships. I decided it was time to increase my ad rates and ride that momentum to my first year of six figure revenue…

…and that’s pretty much the exact point that my business came to a complete standstill.

It’s probably not too hard for you to guess why. In its effort to curb inflation, the Federal Reserve had begun aggressively hiking interest rates, and by early 2023 the entire business community was girding itself for a coming recession. In times of economic uncertainty, a company’s marketing spend is always the first budget item to be cut, and pretty much the entire media industry saw an immediate downturn in advertising revenue. My tiny newsletter did not escape this trend.

In a span of weeks, I went from sold-out inventory to going entire months without a single sponsor. At first, I didn’t panic; I figured that this was similar to that early period of the pandemic when companies just needed to get a lay of the land before recommitting their marketing spend.

But by Summer of that year, I began to acknowledge that the demand wasn’t coming back anytime soon. I reached out to other operators in my space — especially those with experience in ad sales — and determined that there were plenty of ad dollars up for grabs, but I would need to work for them. I could no longer just rely on inbound demand from my own audience; I would have to develop a real sales process that involved outbound cold pitches.

Let me issue the caveat that I have nothing against people who sell ads. It’s a perfectly legit profession and plays an important role in funding media. But I fucking hated the very idea of spending time each week scouring the depths of LinkedIn so I could send cold emails to executives who wanted nothing to do with me. The idea of badgering these people week after week just felt so anathema to what I wanted to be doing with my life, and those few weeks when I was preparing to engage in this activity were some of my unhappiest since the launch of my newsletter business.

Ultimately, I couldn’t go through with it. Was I losing out on a good bit of money by simply refusing to send a few emails? Yes. Did I feel a tremendous sense of relief once I decided that I wouldn’t have to spend time each week hunting down the contact information of a company’s chief marketing officer? Also yes.

With that decision out of the way, I was back to the central question of how I would actually monetize my content. And while I briefly considered the idea of selling evergreen products like ebooks and courses, I eventually settled on the same solution I’d come to four years ago: recurring subscriptions.

By this point, I was approaching the end of 2023. Subscriptions had always been on the backburner, but I had been tinkering around with various paid offerings — live office hours, longform case studies, subscriber Q&As. Each of them drove some conversions, but not at the rate required to overcome churn and generate real growth.

The epiphany came a few months later — when I was writing that stream-of-consciousness Google Doc I mentioned above — that what my subscription offerings really needed were some clear parameters and definitions. I had spent so many years vacillating between different experiments that no-one in my audience — on either my free or paid list — could concisely sum up what they received if they entered their credit card information and opted into recurring payments.

Hence why I’m writing this piece today. I want to spend the remainder of it talking about the subscriber benefits I settled on and why I chose them. Let’s jump into it…

Paid benefits for subscribers

So I’ve always thought that a freemium model should have some level of differentiation between the paid and free services. As such, I didn’t want to simply start sending out extra newsletters each week with a paywall slapped onto them. Instead, I developed three benefits that go above and beyond what I offer to my non-paying audience.

Introductory phone calls

So early on in my newsletter journey I created an automated email that was triggered whenever someone bought a subscription. The subject line was “What do you create and how can I help?” It basically just encouraged the subscribers to reply to the email and tell me a little bit about themselves.

Lots of subscribers did reply, and many of them had impressive backgrounds as media operators and entrepreneurs. Given that these were just the sort of people I like to speak to for my newsletter and podcast, I’d often respond with an offer to jump on a half hour phone call.

These calls were beneficial to both parties. For me, it was a great way to develop relationships with working media operators, and many of those phone calls led to podcast interviews and/or case studies down the line. For the subscribers, it was a great opportunity for them to pick my brain about challenges they were facing in their own businesses.

There was a third benefit as well: I noticed over time that the people I had these phone calls with churned at much lower rates. There was something about the act of talking to me on a Zoom call that made them less likely to cancel their subscriptions.

So with these insights in hand, I changed that automated email Substack sends out when someone buys a subscription. Instead of a request for biographical information, they’re given a Calendly link that allows them to book a half-hour phone call with me.

Obviously, I was a little nervous about opening up this service to the masses, but so far it’s gone great. I would say that about 50% of my subscribers actually take advantage of this benefit, and in most cases I feel like they’ve come away from these calls with a new insight they can use in their careers. They’ve been fun!

Monthly Q&As

As I mentioned above, I experimented with semi-regular “Office Hours” that I would conduct live on Zoom. Basically, about twice a month I’d send a newsletter out to my paid list that included a date, a time, and a Zoom link. Sometimes the calls would be open ended; other times I’d invite on special guests to answer questions around specific topics.

In some ways, these calls were a tremendous success. They allowed my audience to interact with me on a regular basis, and I could tell that the attendees got a kick out of chatting with each other and sharing insights.

The problem was that these calls didn’t scale very well; once they got up to about 30 attendees, it got difficult for me to facilitate discussion and ensure deep engagement with everyone who wanted it. Also, because my audience was spread all across the globe, there were lots of subscribers who were unable to attend these calls because they were hosted at inconvenient times.

So I eventually transitioned from these live calls to asynchronous Q&As. Basically, at the beginning of each month I send out a newsletter titled “Ask me a question” to my paid list. The subscribers are encouraged to jump into the comments section to ask me a question, and then I spend the rest of the month attempting to answer them in podcasts, newsletters, and directly in the comments section. I’ve especially enjoyed teaming up with Alexis Grant, the founder of They Got Acquired, to record a monthly video podcast where we answer subscriber questions.  

Were some people disappointed that I phased out the Office Hours? Yes, definitely. But the good thing about this solution is that it’s available to all subscribers, regardless of their availability and time zones. I do hope to bring the Office Hours series back though once I can hire a freelance producer to help facilitate them.

Premium video podcasts

So the two benefits I listed above provide great opportunities for personal interactions, but they offer limited longterm utility. Having an intro phone call is a lot of fun, but it doesn’t justify an ongoing subscription that lasts months or even years. For that, I needed to build out some kind of regular content series.

As I mentioned, I didn’t want to simply send out extra newsletters and slap a paywall on them. Whatever content I produced, I wanted it to be evergreen and to offer up actionable intelligence that a subscriber could incorporate into their own line of work.

So what could I offer subscribers that no other journalist could? Well, one of the things I’m most proud of is that I’ve built out a huge rolodex of the world’s most successful media entrepreneurs. I’ve interviewed hundreds of them for my newsletter and podcast, and they’ve been extremely open about the exact methods they used to build their businesses.

The idea I settled on is an interview series where we home in on a very specific aspect of their media business. Rather than a wide-spanning interview about their whole business — the kind I conduct for my free podcast — I instead spend 30 minutes grilling them on the ins and outs of how they do a very specific task. To get an idea of what I’m talking about, check out this sampling of headlines from the series:

1. How Political Wire built its successful subscription offering

2. How The Author Stack grew to over 31,000 subscribers

3. How the Geekout newsletter grew to 30,000 subscribers

4. How the Wonder Tools newsletter grew to 39,000 subscribers

The great thing about Substack is that it allows paid subscribers to generate their own customized feeds into their podcast player of choice — whether it’s Spotify, Apple, or Overcast. Once that feed has been activated, then all future podcasts are automatically populated into their podcast players for as long as they remain paid subscribers.

But I knew that not all of my audience consists of dedicated podcast listeners, so I needed to create a version that’s easily consumable in the browser. So not only do I automatically generate a transcript for each interview, but I also upload a video version of the interview to YouTube. I publish it as “unlisted” and then embed the video behind the paywall. This way, my subscribers can watch the interviews during their lunch breaks or on their subway rides home. They can even forward the video link to their colleagues.

What I like about this approach is that these interviews are evergreen, so the value of a subscription will only increase as I publish more of them. My hope is to eventually amass hundreds of interviews that new subscribers can browse through at their leisure. 

Some concluding thoughts

I know I struck a rather pessimistic tone through much of this article, but the truth is that the last four years have been the most rewarding in my career. I love the amount of creative freedom this job affords me, and I truly enjoy nearly every aspect of my work week — from talking to successful media operators to creating the content.

I’ve been extremely lucky that I have a supporting spouse who provides a steady income through her job, but that doesn’t guarantee that I’ll be able to continue this work indefinitely. Without sustainable revenue, I’ll eventually have to go back out and find a traditional job.

So if you’ve made it this far and these benefits sound at all enticing to you, consider becoming a subscriber. With every newsletter I put out and every podcast I produce, I try to help you with your career, so now would be a great time for you to help me with mine. Use the link below and you can get 20% off for the first year. Thanks for reading this far, and I hope to have you as a reader for years to come.

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