Letter.ly’s Money Issues


A few additional thoughts around the “paid” part of paid newsletters; in short, I’m wondering whether introducing money into the system is actually worth it for personal email newsletter creators.

1. Money as Motivation for Writers

A couple of letter.ly writers have mentioned the motivation to write that comes from having paid subscribers as a factor in their decision to try running a paid email newsletter, but I don’t entirely…um, buy this.

Having paid subscribers creates an obligation to write, rather than amotivation, and confusing those two can easily lead to intense feelings of stress and guilt without producing any additional writing.

Getting paid (even a token amount) can also provide justification for writing more, but that again is very different from providing the motivation to write more.

2. Money as Incentive for Comparison Shopping

Adding money to the system invites comparison to other sources of paid content, and for me, the obvious ruler was Daring Fireball. I pay $19/yr for Daring Fireball “membership,” which basically gets me all the writing that John Gruber puts up for free anyway, plus a bonus feeling of smug superiority.

I took a quick look at the DF archive, and Gruber posts at least one (and usually two or more) substantial pieces of writing each week, plus a number of small links/quotes with a sentence of commentary each day. And while you may or may not like Gruber’s style and positions, he’s an extremely good writer offering solid analysis and insights.

The quantity and quality of Daring Fireball at $19 makes me look hard at the $24 – $48 range that letter.ly writers are settling into; everything I’ve subscribed to has been good, but are the $3.99 newsletters actually $1 better than the $2.99 newsletters? Are they all “worth” more than Daring Fireball? Because I’m paying for them those comparisons inevitably come up, for better or worse.

3. Money as Proxy for Audience Commitment/Engagement

Sam Lessin (letter.ly creator) noted that one of his reasons for switching to a paid newsletter was that he wants an engaged audience, and that with letter.ly readers signal their commitment by paying for the subscription.

Despite the number of words I threw into the “comparative pricing” section of this post, I think that money — particularly a small amount of money — is a terrible proxy for commitment in this case.

Having to pay for a subscription puts a barrier up front, keeping out the most casual and disengaged of potential readers, but once a reader has subscribed we’re talking about a very small recurring charge on their monthly credit card bill: the newsletters that I subscribe to combined cost less than a single drink at some NYC bars.

Unless a writer sends out something that irritates a reader into using the unsubscribe link at the bottom of the email, I suspect that a combination of inertia and social pressure [“X will know that I unsubscribed, will they take it the wrong way?”] will be enough to get people to ignore that latte-sized charge when reviewing their credit card bill each month — whether or not they’re actually paying attention to the newsletter.

4. Whit’s Alternative Formulations

I understand and agree with many of the motivations behind letter.ly, but I do question whether paid subscriptions are the most effective means for achieving letter.ly’s goals.

If the issue is curating your audience, then take some responsibility as ringmaster. Why not forget using money as a no-effort proxy and follow the route that the Pho list does? Have people send you an email explaining who they are and why they want to be on the list.

Select from among the people who are willing to make an investment of time and effort to be a part of your list, rather than just accepting anyone willing to spend a couple of bucks a month.

If the issue is ensuring an engaged, active audience, then require real activity from your newsletter subscribers. What if, rather than an unsubscribe link in each email, you had a “keep me subscribed” link? If a subscriber doesn’t click that link (or hasn’t clicked it for n consecutive newsletters), they’re automatically removed from the list.

Or take the same basic approach, but requiring a reply email at least once every n newsletters: if you’re not writing newsletters that people really want and pay attention to, your subscription count shows it.

Put a system in place so that an inactive user an unsubscribed user.