I published the first issue of Now I Know on June 22, 2010. It went to 20 people. I knew most of them – a few others came in from, if I recall correctly, a Facebook post by Jimmy Wales, who I used to work for at Wikia. Only 12 people opened it – that’s high, at 60%, but low, at 12 people.

On June 22, 2011, Now I Know went to 5,897 people. And on August 1, 2011, it broke the 10k mark: the email went to 10,013 people.

Here’s how I got there. (Or, at least, this is how I remember it.)

Before starting, I laid out a few ground rules for how I’d grow the newsletter.

1) No paid-for ads. I did not (nor do not now know) the lifetime value of a subscriber, and I don’t want to run this in the red. Other than a $20 buy on reddit – mostly to learn how their ad system worked – I haven’t spent a dime on ads. (The reddit ad got me something like 3 or 4 subscribers.)

2) No premiums. “Premiums” are those bonus offers one gets for subscribing to something – kind of like how banks used to give out toasters to people who open new savings accounts. This rule also includes a ban on sweepstakes (“sign up for a chance to win an Amazon gift card!”) types of offers. The reason here? I want people to sign up because of the content, and not for some ulterior motive.

3) Double opt-in. If you want to be on the list, you have to subscribe through the site and then confirm your subscription by clicking a link in an automatically generated confirmation email. I did not even sign up my mother or father myself. (My mom isn’t subscribed at all; my dad went through the double opt-in process.)

Violating any of these three would have let me grow the list faster, but the restrictions helped tremendously in improving the product.

I also have one other restriction – no SEO. This isn’t by choice (and in fact, I’m hoping to fix it, but I don’t have the time or development chops). Basically, all the archives are on Mailchimp’s servers, with horrible URL structures and other problems. So I’ve received basically no search engine traffic to date.

So, what did I do?

The early days of the list are a bit of a blur, but looking back, my posture was that I was experimenting, trying to figure out the editorial product as I went along, and I needed people to read it to help me figure it out. (This was honestly the case, for what it’s worth.) At the time, I had about 500-700 twitter followers, my general (real-life friends) base on Facebook, and a few people – Wales, of course, but also Marshall Kirkpatrick, Jeff Pulver, and others who I most certainly am forgetting (sorry!) adding a tweet to that effort. And in about two weeks, I had 100 people subscribed.

But beyond the standard “leverage your network,” here is what worked for me. And, what didn’t.

1) I actively sought out potential promotional partners.

The “others with similar content” crowd is an obvious way to go. I’ve spoken to the people at MentalFloss, Brain Pickings, an editor at National Geographic, and many many others. Most have been receptive to cross-promotions, content sharing/syndication, or just plain being friendly and helping.

There’s an advantage, though, to being an email newsletters as opposed to, say a blog. The medium is so under-utilized that, by simply being in the space, there’s a small community of fellow travelers available to me.

To that end, I’ve spoken with Kale Davis at Hacker Newsletter probably two dozen times over the last year, but also with many other newsletter publishers. This helps tremendously – not just when it comes to promoting each other, but also in figuring out the ins and outs of the platforms you are using. (You may note at the bottom of Now I Know’s landing page that I explicitly mention Hacker Newsletter – Kale let me borrow their landing page design.)

And getting a mention in another newsletter is uniquely effective for another reason: their readers are already willing to accept newsletters in their inbox.

2) I let others republish my work.

My basic rule is that you can take my newsletter content and republish it on your blog if (a) you ask me first and (b) you put a plug for the newsletter at the top and bottom of the post. I have specific wording I ask for, which MentalFloss actually developed, but seems to work.

This also helps with SEO. Google “abraham lincoln secret service” and the reproduced version of my article, on mentalfloss.com, comes up. They get the traffic, I get a fantastic ad for my newsletter. Win/win.

3) I’m trying harder not to be shy.

This is a hard one for me.

I think it was Wayne Gretzky who said that you miss 100% of the shots you don’t take. It’s a crude analogy, of course, but aren’t all analogies crude?

Anyway, one of the best sources for subscribers has been this single post by Brain Pickings, suggesting Now I Know as one of five “fantastic daily email newsletters for a better life.” Beyond being flattering, it’s actually driven a good sum of people to sign up. (After all, they don’t have to take my word for it!)

How did Maria Popova, the editor of Brain Pickings, find out about Now I Know? It turns out I emailed her, unsolicited, about it. That’s it.

It’s a fine line, of course, between spamming and networking, and one I am very concerned about crossing. I probably should do more of it, not less, but again, I’m trying harder to not be shy. It’s very foreign to me, though.

4) I participate in online communities.

Here’s a poorly-kept secret of the Internet: If you participate (properly) in a community, opportunities spring up.

Reddit is an obvious one. I’ve been a redditor for five years, collecting 15,000 “link” karma over the span, and another 6,000 or so comment karma. I keep an eye out for Now I Know issues which are posted there (and sometimes post them myself, although in the case, the below does not apply) and when I find it, I thank the submitter and then point out where the article came from. That’s gone over pretty well, as seen here. I also answer a lot of questions in the Ask Reddit section, and when appropriate, mention my work. That’s also been viewed as acceptable if not welcome.

I’m also a somewhat active commentor (commenter? Neither are right. We need better dictionaries) on Fred Wilson’s blog. He picked up on one of my comments and invited me to write a guest blog post, so I did – one which mentioned Now I Know.

In each of these case, I wasn’t some random passerby who happened to spew out my content. I was a regular at both of the sites well before the opportunities arose.

5) I decided to go with “email newsletter” instead of “blog.”

Okay, okay, part of it goes without saying – you can’t build an email newsletter to 10,000 subscribers unless you’re building an email newsletter. But that’s not my point here.

There’s a certain novelty to being an email newsletter publisher instead of a blog publisher. That’s why the Brain Pickings post above makes sense; that’s why when Smashing Magazine can make a post about email newsletters worth subscribing to. Imagine how weird it would be to have a post called “blogs worth reading!”

* * *

Okay, what hasn’t worked?

1) Content isn’t king.

Over the last four months, Now I Know’s archives have picked up 1,078,095 page views from about 790,000 “absolute unique visitors,” whatever that means. Views to archived pages do not include the “copies” sent to subscribers, forwarded by them to friends, or a few other things.

In that same amount of time, Now I Know has picked up about 6,000 subscribers. That’s a capture of under 1%. And it’s actually much, much lower. I have a StatCounter tracker on the Now I Know landing and archive pages. I can’t measure conversions precisely, but anecdotally, I know that a tiny fraction of those 6,000 came through the archives. Getting an endorsement from someone, be it on twitter, their blog, etc. which sends the potential subscriber to the landing page does the trick. The content doesn’t do the job.

This may be my fault. The content is good (I hope!) but I’m not really doing a good job optimizing to convert passersby into subscribers. I don’t really feel like there’s a big opportunity here though (without running Popup Domination) of converting a significantly higher number.

2) Tweets aren’t so great.

This may be specific to me and my product.

I have gotten some great endorsements from twitter users with tens of thousands and even hundreds of thousands followers. None of them have been gangbusters in terms of growth, at least not quantitatively.

I still try, and I still ask, for these types of tweets. But the engagement driven by those tweets isn’t so amazing.

Why? Topically, I’m a wild card. I think if someone who had a reputation for odd-ball curiosity were to send a tweet out, I’d see a lot more in the results column. Second, I think most of these tweets are one-offs, unrelated to another, so there’s no critical mass and I’m not hitting the “rule of seven."

3) My product isn’t very viral.

This isn’t terribly surprising, but it’s definitely true. To the extent that there are people who regularly share (by forwarding) the content with their friends, there are some conversions, but not a whole lot. I do not measure this directly, but anecdotally, again, it does not seem like it is fueling significant growth. Don’t misunderstand: it is definitely net positive, and it helps, but it’s not going to drive growth on its own.

* * *

The future is hard to say. Traffic still comes in fits and spurts, and pullback/unsubscribes are probably (relatively speaking) no greater than before, although they clearly are in absolute terms. So far, August is disappointing, but it shouldn’t be – I’ve experienced 8% growth this month, which is definitely a good thing. The disappointment stems more from the fact that a really great day, gaining 150 new readers, isn’t as awesome now as it was when I had, say, 500 subscribers.

All that said, I think I’ve done a decent job so far and I’ve set the list up to move in the right direction.