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by Jacob O'Bryant

Help me sponsor your newsletter

Summary: I've made a directory for newsletters that sell self-serve ads. Read on for background info.

Now that Yakread's core features are complete and I feel good about the app's design and structure, I've turned my focus towards optimizing retention. It's one thing to make an app that scratches your own itch, which I've done. It's another, much harder thing to design the user experience well enough so that lots of other people can get value from your app. Your own product instincts aren't enough; you need to base your decisions on feedback and data from your users.

And to do that, it helps to have a steady flow of new signups so that you can try out different things and find out what works. That's why I've started buying ads in newsletters. Recently I've scheduled about $1,700 worth of ads to run over the next couple months, and going forward I'd like to spend about $500 - $1,000 per month. I'm not too focused on getting positive ROI from ads yet; for now, I just need enough people to use Yakread so that I have some analytics data to work with.

Last year I spent about $15k advertising The Sample – I know the exact number since I started doing my taxes on Saturday – so I have a little experience with various ways to lose money on ads. Suffice it to say that this time around, I'm focusing on sponsoring newsletters.

Newsletter ads are a good fit because Yakread is an app for reading newsletters. If you subscribe to a newsletter, you're a potential user to whom I'd like to advertise. The downside of newsletter ads vs. Facebook or Google ads is that they take more legwork. Facebook makes it very easy to give them your money, and as a result the bulk of my ad spend last year went to them. But what newsletter ads lack in convenience, they make up for in quality.

There is a lot of potential to make it easier to spend money on newsletter ads, and the easier it gets, the more money will be spent. I have some ideas about how to do that, and I'd like to give it a shot both to aid my own advertising efforts and as a way to support the newsletter ecosystem more broadly. If we want to unbundle social media, developing a robust advertising alternative to Facebook et. al. will be an important part of that.

So how do we make newsletter advertising more convenient, especially for small-time buyers like me and small-time sellers like, perhaps, you?

Affiliate-style ads are one option: ad buyers set up a deal of some sort, and then ~anyone can run the ad and get paid based on how much traffic or how many conversions they drive. There are several platforms already that assist with affiliate newsletter advertising. I've even built affiliate/referral programs into Yakread and The Sample, where you get free advertising credit in return for referring new users.

But there's another, complementary method that I'd like to see more emphasis on: self-serve. Instead of trying to aggregate sellers or buyers, just make it really easy for buyers and sellers to transact directly. If you run ads in your newsletter, can someone buy an ad without needing to email you? You can set a higher price for people who want to sponsor you specifically, while using affiliate deals whenever you have unfilled ad space.

Aggregation can be built on top of self-serve. For example, if you've got a list of newsletters that do self-serve ads, you could compile them into a directory to help buyers find newsletters to advertise in. And spoiler alert, this is exactly what I'd like to help kickstart.

Step one: set up self-serve ads in your newsletter

There are already several tools you can repurpose for selling newsletter ads. I recommend Calendly. I set up an example booking page that you can poke around. I connected it to my Stripe account for receiving payments; you can also use PayPal. You need to be on the $12/month plan to receive payments, though you'll start out with a 2-week free trial.

A few other options, the first two of which I've seen in the wild:

  • YouCanBookMe. $10/month. I started setting up an example booking page with this but found it to be a bit more complicated than Calendly. You have to connect an external calendar instead of directly entering the time slots you're available.
  • Typeform. $25/month. I personally hate Typeform, but maybe, like pop-up subscription forms, the one-question-at-a-time thing is good for conversion despite the crappy user experience.
  • Stripe Payment Links + Google forms or whatever. I haven't actually seen anyone do this, but it could be a good option if you really don't want to pay a monthly fee. It'll take a little more work to set up than Calendly and the end result won't be quite as nice (for buyers or for you), but eh.
  • Sponsy, the only thing here that's purpose-built for newsletters. Cheapest plan is $399/year (which comes to about $33/month). They (I think it's a solo founder?) seem to be targeting large publications with more complex needs, which makes sense. This might be a good option if you outgrow Calendly.

Step two: add your newsletter to my handy-dandy self-serve ads directory

As a public service and in an attempt to encourage collaboration, I have created a free directory on this page: You can submit your newsletter there, and you can view all the previous submissions. If you're an ad buyer and don't mind sharing, you're also welcome to submit any newsletters you're aware of that have self-serve ads. The directory is hosted on Airtable. I've seeded it with a handful of newsletters I've run into, some of which I've sponsored myself.

This actually isn't the first newsletter directory I've made. As an experiment, I made a similar Airtable-backed directory to go along with The Sample. When people join The Sample, they can opt to join the directory as well. That one has fields to specify if you're interested in cross-promotion, buying ads, and/or selling ads. It has 920 participants as of writing. But the vast majority of them don't provide self-serve booking, so I'm hoping to encourage that with this new directory.

There are many ways the directory could be improved (shoot me an email if you want to take that on as a side hustle). But even in this minimal form it should be helpful, at least if it gets enough participants. If you submit your own newsletter, I can at least guarantee that you'll have one potential sponsor from it 🙂.

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Published 28 Feb 2023

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