How Giving Away More Content for Free Helped Me Get — and Convert — More Subscribers

After a few years of experimentation, I’ve finally found a simple, reliable way to convert more readers of my free tech advice newsletter into paid subscribers.

All I had to do was start offering most of the paid newsletter for free.

This strategy might seem counterintuitive. For years I feared that giving away too much would erode the value of a paid subscription. It turns out the opposite is true: Erring on the side of generosity has made people even more likely to pay for the rest.

Two newsletters and one big dilemma

Let’s back up a bit because my newsletter situation is somewhat complex.

I’ve been a professional tech journalist for about 15 years. In 2016, I launched a free newsletter called Cord Cutter Weekly, which helps folks save money on TV service. I promote the newsletter through my weekly column on cord cutting over at TechHive and hit the 10,000 reader mark within 18 months. Today, Cord Cutter Weekly has nearly 31,000 readers.

Drawing on that success, I launched a weekly paid subscription newsletter called Advisorator in 2018. The idea was that if people trusted my advice on streaming and cord cutting, some of them might pay for a newsletter that helped them navigate the wider tech world.

It’s been a modest success, growing by a couple hundred subscribers yearly. Still, even now, with more than a thousand subscribers, the conversion rate isn’t stellar, given the size of Cord Cutter Weekly’s readership. Without a free entry point to Advisorator, I also excluded potential readers with no interest in cord cutting.

All this led me to experiment with a free version of Advisorator a few years ago. Every week, I put together a brief excerpt from the paid edition and would link to the newsletter on sites like PCWorld and Fast Company, where I write about topics other than cord cutting. This free edition now has nearly 3,800 readers.

But compared to Cord Cutter Weekly, it’s even worse at generating paid subscriptions. This scenario created an awkward situation in which I’d mostly stick to promoting Advisorator’s paid edition in Cord Cutter Weekly while promoting the free version everywhere else.

Bulking up the free edition

Deep down, I knew the problem: Advisorator’s free edition wasn’t all that great. I tried several approaches — excerpting a quick tip or two, highlighting a notable deal, and even switching to a more news-oriented format — but they all felt lightweight, and none helped draw in more paid subscribers. Most weeks, I was lucky to convert a single reader; I often got none.

All that changed in April when I saw what Janko Roettgers was doing with his weekly Lowpass newsletter. While his news analysis and link roundups are free, his feature column at the top includes just a few intro paragraphs, with the full story paywalled for non-subscribers.

The approach had crossed my mind before, especially after reading CJ Chilvers’ reflections on 35 years of newsletter publishing. (“You’re probably not giving enough away,” he wrote.) But seeing it done by Janko — a fellow longtime tech journalist whose work I admire — was just the nudge I needed.

The new format for Advisorator’s free weekly edition looks like this:

• An in-depth feature column, paywalled after a few paragraphs.
• A roundup of tech news with tangible consumer impact.
• One to three brief tips or apps to try.
• Quick links to interesting stories around the web.
• One notable deal on a tech product.
• Another paywall for the full list of deals.

Essentially, it’s the same newsletter as the paid edition, minus a couple of paywalled elements. The average issue of Advisorator runs about 2,000 words, and more than half of them are now free.

While you might think this would discourage paid subscriptions, conversion rates immediately went up after making the change.

From January to mid-April, about 13% of my new paid subscribers were readers of Advisorator’s free edition, with the rest coming exclusively from Cord Cutter Weekly. That ratio has since jumped to around 25%. Some weeks, I convert even more subscribers from Advisorator’s free audience of 3,800 than from Cord Cutter Weekly’s audience of 31,000, which was practically unheard of before.

Just as importantly, I’m proud of the free edition now. It feels like a substantial publication rather than table scraps. I plan to start advertising it in Cord Cutter Weekly instead of pushing those readers directly toward the paid edition.

Why it worked

In hindsight, it’s obvious to me why giving more of Advisorator away is better at converting subscribers:

• The feature column’s intro text — combined with a conspicuous paywall — clearly indicates what readers get with a paid subscription.
• Every newsletter still provides plenty of standalone value, encouraging people to open it in the first place. (Open rates tend to be just short of 50%.)
• Advisorator’s online archives and guides are still reserved for paid subscribers, so having a robust free edition creates more chances to link back to paywalled content.
• A little paywalled material at the bottom of the newsletter serves as a last reminder to check out the paid version.

The great thing about personal newsletters, in general, is that they help build relationships with readers. (There’s another lesson from CJ.) Big companies might be able to offer more content, but they struggle to replicate the sense of connection that comes from an individually-crafted newsletter. That’s what allows me to have a viable and still-growing subscription business, even in an age of subscription fatigue.

Being more generous with my free newsletter helps strengthen those relationships with readers and encourages more people to support my work. I only wish I’d realized that sooner.