Hello! Who are you and what newsletter did you start?

I’m Jacob O’Bryant, and I made The Sample.

The Sample is an unusual newsletter. Instead of sending subscribers content that I’ve written myself, I forward them posts from other newsletters that have opted-in. I try to help other newsletters get subscribers.

When people sign up for The Sample, they can specify a few topics they’re interested in, and we use a recommendation algorithm to pick which newsletters get forwarded to which subscribers.

How did you launch it and what did you do to get the first 100 subscribers?

I had been working on other recommendation-related products for a couple years when I started The Sample, so I started out by announcing it to people who had already signed up for other stuff I made. Findka Essays for example was The Sample’s immediate predecessor and it had 400 or so subscribers at the time, mostly from Hacker News.

Besides that, I looked for discussions on forums etc. where people were discussing newsletter cross-promotion, and I emailed people directly. I said stuff like “Hi! I’ve been going through discussions about newsletter cross-promotion on Indie Hackers and I saw your post here: [link]. You mentioned [something relevant]. I just made a product that you might be interested in. [More explanation]. Would you be interested in trying it out?”

I did a similar thing to get some initial users for Findka Essays actually; for that I searched for Hacker News discussions about RSS. I think it’s a good tactic in general for getting some initial users, as long as you’re tactful about it and demonstrate that you actually read their post and stuff. It is a lot of work for only a small number of signups though.

I don’t remember if that got me past 100 or not, but I also took out some classified ads in other newsletters which I also think is an excellent way to start out for anyone doing a newsletter. It’s difficult to make advertising scale profitably, so I wouldn’t recommend it as an ongoing growth strategy unless you know what you’re doing and the numbers work out. But if you don’t mind spending at least several hundred bucks, it’s probably the easiest way to get to the 100 subscriber mark and hopefully have some readers who will give you some feedback.

What does your process for creating the content look like?

Since The Sample just syndicates content from participating newsletters, the process is simple: I let other people do it 🙂. It did take a lot of up front effort to design and build The Sample though. I had to set up a system to import newsletter posts automatically. Before we forward the posts, we also have to add our own header and footer and strip out various things from the original post like unsubscribe links. And then there’s the recommendation algorithm which crunches all the usage data we get from our subscribers and decides which newsletters to send them next. And there’s a bunch of stuff on the writer side, so people can see how many times their newsletter has been forwarded, how many subscribers they’ve received, etc etc. But now that all of that is set up, I mostly just let it run.

What tools are you using to create, send, and grow the newsletter?

The whole thing is built with custom code. (I have a software engineering background, if that wasn’t already evident). We use Mailgun to send the emails. We have a referral program where newsletter writers can share a link to The Sample, and then we forward their newsletter more often in return.

What have you tried to monetize the newsletter and how well did it work?

At first I tried regular classified ads. I set up a self-serve advertising page where people could put in a link and some text, then we’d insert it in the header that we stick at the top of the newsletters we forward. They got very few clicks. I think the ad CTR was like 0.2% or something.

So we scrapped that, and instead we started letting writers pay to have their newsletters forwarded more often. It uses an automated bidding system like Facebook or Google ads. You set some spending limits, for example, maybe you say you’re willing to pay up to $3 for a subscriber and up to $100 per week. Then we’ll give you some extra forwards and you pay for each additional subscriber you get. On the readers’ side, these newsletters are marked with a “sponsored” label. This has worked fabulously.

Since launch, what has worked to attract and retain subscribers?

The biggest thing was getting lucky. After getting up to about 600 subscribers mostly via newsletter ads, I did a Show Hacker News post that got on the front page and referred another 300 subscribers. Also on a whim I submitted The Sample to Recomendo. They featured The Sample and it drove over 2,000 signups almost overnight. I was going out of my mind. I’m eternally grateful for that.

After The Sample had hit the milestone of referring 10,000 subscribers to other newsletters, I wrote a post about the product that included a bunch of business metrics and stuff. I shared it in a couple newsletter communities and it was well received. We got an uptick in subscribers and newsletter submissions from that, and I think the post also got some exposure to people in the media industry. I noticed it was shared by the founder of NiemanLab, for example.

The cross-promotion system I mentioned has also helped a bunch. 21% of our active subscribers came from it. That also drives a lot of the newsletter submissions we get; writers have been very happy to share The Sample with each other. I also still do some newsletter advertising somewhat passively. The biggest ad I’ve ran cost $1,000 and went out in July, and we just hit ROI positive on it a few days ago.

How are you doing today and what are your plans for the future?

We have about 10,000 subscribers right now, and we do anywhere from $1,500 to $3,000 in revenue each month. Unfortunately The Sample has pretty low long-term retention. Everyone churns eventually. Last I checked, subscriber activity (in terms of # of forwarded newsletters they subscribe to, which is our main metric) was highest right when a cohort signs up, and it declines linearly until about day 200, after which it pretty much hits zero.

As a result, we’ve been on a plateau forever. Right after Recomendo featured us, we were driving 700 or so signups for participating newsletters every week. We’ve never been able to get past that; lately we’ve been doing 500 or 600 per week.

Much of this year was spent trying to figure out if we could either (1) change the product in some way to make it retain better, or (2) make paid acquisition work well enough that we can just get tons of paid signups all the time and recoup the acquisition costs before they churn. My conclusion on both is “probably not,” although our newsletter ads have been doing better than I expected. Those take a lot of work to scale though, and I’m not sure if we could do it profitably enough to make a stable living.

So I’ve actually started working on a new complementary product, Yakread. I think that will provide a better “beach head” so to speak. If I can turn that into a successful business, I think it’ll open up opportunities to do even more interesting things with The Sample down the road.

Ultimately the plan is to be part of the answer to the question, “what comes after social media?”

What’s one piece of advice you’d like to share with someone who wants to get started or is just starting out?

I’d hesitate to give advice for newsletter writers since that’s not my main thing. But probably the most important thing I’ve learned about being an entrepreneur is that I don’t genuinely care about it that much.

Entrepreneurship is a means to an end for me; what I truly care about is invention. I think much of my time would’ve been better spent if I dropped the “do this as a profitable business” goal.

I’m in kind of deep at this point and I do think I still have a chance of pulling it off, but there’s also a possibility that I end up getting a job and only work on my projects on the weekend. That wouldn’t be the end of the world, especially if I can pull off getting a 4-day-per-week thing or do consulting, and if I make enough that I can hire someone to help me build out my ideas part-time. (Perks of working in tech.)

So I guess I might say “try to figure out what you actually care about, and if that doesn’t line up with building a profitable business, that’s OK.”

Where can we go to learn more?

• The post I mentioned earlier

• We need better tools for online speech, an essay in which I lay out my long-term ambitions

• My three most recent posts which discuss Yakread: part one, part two, part three