Patrick McKenzie (patio11) here. You're getting this email because you requested my periodic thoughts on making and selling software. Sorry that it has been a while since my last essay -- my time budget for writing has been absorbed by other projects as of late. (Regarding which, more later.)
[Edit: Actually, it's possible that you've never gotten an email from me. Somebody might have just given you the link to this page, which is an online archive of an email that I sent to folks who had asked for it. If you'd like to get articles like this in your inbox, totally free, about once a week or two, give me your email address.]
The industry comes up with the least appealing names for some of the most important concepts. One of my favorite examples is "growth hacker", which is the industry's favorite way to describe much of what I do for a living and, simultaneously, a crime I will never plead to. Another is "content marketing," which describes what J.R.R. Tolkien and Britney Spears would have in common if both were pathologically insecure about their art.
I make and sell software. Writing is an incredible asset in accomplishing that, both for directly encouraging sales and for collecting an audience of people who would be good prospects for my software/services if they only knew they existed.
This is broadly true for many software companies -- Fog Creek and Basecamp (formerly known as 37signals) both were extraordinarily successful with using writing as a friendcatcher both for their philosophies of the world and, secondarily, for their paid products. Many SaaS companies have cottoned onto the fact that writing (and podcasting, and making videos, and the like) is often less expensive than leasing traffic from Google on a monthly basis. Unfortunately, many make mistakes in tactics and strategies which blunt the good that writing can do for their audience and their business.
Let's talk blogging. I hate blogging, in that peculiar manner of hatred that one only discovers after spending lots of time getting good at the hated thing. How do I hate blogging, let me count the ways.
The Framing of "Content" Often Devalues It
People are extraordinarily sensitive to framing. "Art" is valuable. "Content" is not.
"Content" suggests that something is mass-produced in a factory-like setting, which is unfortunate, because the type of people you're trying to sell to probably don't think that "mass-produced in a factory" describes anything that they want to buy. A quick anthropological thought experiment: if you're selling enterprise software, do you think the decisionmaker considers themselves the kind of person who eats Kraft singles or the kind of person who appreciates artisanal cheeses? You should probably meet them where they are, rather than producing the written equivalent of pink slime, like TechCrunch or ValleyWag.
That was a low blow. Sorry, pink slime.
The industry uses the word "content" primarily because it is form-factor agnostic, but that is again unfortunate, because people have really strong opinions about form-factors. They even have very strong opinions about the names of form-factors. For example, articles and essays suggest erudite writing created by experts... and then there are blog posts.
Blog posts are quickly-depreciating commoditized drek. Everything about the design and packaging of them says Do Not Take Me Seriously. The format encourages function -- real-time short-form reporting and snap analysis -- which in turn makes short-form reporting and snap analysis into people's default grading scheme for all blog posts.
This is very unfortunate to businesses, because it structurally inhibits value creation. Ideally, we want to create things we can keep. Your writing will, for the most part, favor timeless "evergreen" topics that will be equally relevant to your audience / potential customers years from now. (There's a place in your business for seasonal promotions and announcements, of course, but that's a relatively small portion of one's ongoing writing efforts. Three years from now it will not matter whether the announcement of the 7th point release of your software was well-written or not.)
I once wrote an article about salary negotiation. If you go by the numbers, it created more value for more people than any other single thing I've ever written. (I keep a label in Gmail for when folks tell me they got a raise as a direct result of advice in there. The running tally is in the high seven figures a year these days.) I think if I were to revisit the topic today I'd write substantially the same advice. However, that article has a date on it, just the fact of it having a date on it makes it less useful.
I have seen variants of the following conversation happen on Twitter / Reddit / HN / etc multiple times.
"I just got a job offer as a front-end engineer at a Valley company. How do I handle the salary negotiation?"
"Patrick wrote about that here. It is good advice."
"That looks like it was written in 2012. Do you have anything more up-to-date?"
History is a pretty wild rollercoaster, but nothing which happened in the interim has suddenly made "Don't negotiate your salary!" or "If you do negotiate your salary, start by naming a nice low number. You can always work your way up later!" into good advice. And yet if you put a date on your work, people immediately assume it gets stale. This is even institutionalized in some forums -- Hacker News, for example, will append e.g. "(2012)" to the title of anything published in a different calendar year. If you've got your server logs opened with tail -f (I have weird hobbies, what can I say), you can watch in real time as that date makes the link less likely to be clicked on or commented about.
"But publication dates often provide important context!" Horsepuckey. You can, and should, make the strategic decision that you'll primarily write things which retain their value. (It takes approximately the same amount of work to create great writing which lasts versus creating great writing which ages quickly. Given the choice, unless you're the New York Times and your entire business is built around throwing out some of the world's best writing every day right after breakfast, you should choose to write things which last. After all, you don't write software with the explicit intention that it will suffer bitrot hours after release, now do you?)
If the context were truly important some of the time and not others, people would make the considered decision "Does this post need a publication date?", but nobody does that. Most writing only carries a publication date because that was inserted several years ago into the WordPress template by a designer. The designer likely knows nothing about your company, to say nothing of the instant work. He put in a date because WordPress makes it really easy and because everyone knows that blog posts have dates. He also probably made the decision to make the date front-and-center in the blog post, rather than treating it as minimal-impact metadata and burying it after the main text or putting it in a bots-only header.
Improving Discoverability of Your Work Through Better Navigation
You can certainly use WordPress for your business, by the way. (It is probably the best general-purpose CMS. It makes it easy to get started making things, which is important, because that makes it much likely that you or other folks at your company will successfully make things.) Just don't blog your best work. Reserve the blog for ephemera like upcoming conference dates.
Call your essays essays. Call your comprehensive guides comprehensive guides. Take the dates off their templates, or treat the dates as unimportant metadata rather than getting equal billing with e.g. the byline of the industry expert that you had write the article.
Build your best work into the core navigation of your site, just like you'd build important features into the core navigation of your applications. One of the reasons that blog posts tend to depreciate straight off a cliff is that they're often only discoverable if you page through Archives, which is something that most readers will not do.
This makes your work more discoverable by both people who are already on your site and, through being an appeasing offering to the gods of Mountain View, people who have not already heard of you yet. Most of your writing will get its first, and likely most important, burst of algorithmically discoverably trust signals via links from you. When you embed your writing into the core navigation of your website, it tends to automatically pick up more juice from your most trusted pages. If you put it on the blog, when it is on the top page of the blog it will have a bit of authority, but as the post ages it will (typically) have the link graph change in ways which are detrimental to it, and by consequence, to you. (SEO sidenote: Most blogging software out of the box almost tries to make Google hate its archive pages. That's a curious decision. Prefer per-month archives rather than paginated archives. This is particularly true for those of you who will extend or custom-build CMSes yourself to take advantage of opportunities discussed below.)
Have Concrete Goals For Everything You Produce
Some companies are really, really good at producing compelling work, but not quite as good as having that compelling work serve actual business goals. Frequently, this is because they are either confused as to what their immediate business goals are, or they just don't make a process of tying them to the things they produce.
I'd encourage you to not fall into this trap. Assuming an average level of skill at producing great things which spread, 10Xing the number of people who see your work requires quite a bit of effort. 10Xing the business results of the work can be really, really easy. Do you not routinely put calls to action on it? Put a call to action on it. Done.
What should that call to action be? In most cases, rather than immediately asking for someone's credit card, you're just going to ask for permission to continue the conversation started by your work. This can either be literally a conversation -- many software companies have unit economics which easily support their experts talking to potential customers -- or it can be asking for someone's email address so that you can continue sending them things they'll like.
You can spend an awful lot of time on optimizing the collection and use of email addresses. I once produced an entire course on this topic. Here are a few tactics which are fairly easy to implement and virtually invariably work:
Promise your audience that you'll give them immediate marginal value in exchange for their email address. For example, if you're Basecamp and you happen to have a bestselling business book just lying around, you could offer that in exchange for email addresses.
The industry commonly offers guides / white papers for this purpose. There's nothing wrong with a particularly well-executed guide (though please, please, please don't call it a "PDF file"), but I personally love being able to make something which sticks out a bit.
Jason Cohen used to ship people an honest-to-God you-can-smell-it trees-died-to-get-you-this paper book on code review, absolutely free, back when he was trying to evangelize code review as a routine practice in software development. If your unit economics work out such that a lead is worth $10~$20 -- and they easily do in enterprise software -- then this is affordable and buys you a lot of goodwill with customers.
As to where to put calls to action, I like a combination of clearly-templated house ads (such as the ones you'll often find on the sidebars of blogs) and then one or two understated in-content callouts. I generally put towards the end of a piece rather than towards the beginning. This tends to result in you getting less leads, but I think that it keeps the early emphasis of the piece on providing value for the customers rather than extracting value from oneself, which strikes me as the right balance. (Although I suppose one could edit one's work after it has initially been posted, such that it tilts towards the customer for the spread phase of its lifecycle and, after initially spreading, gets a bit more aggressive about accomplishing business goals.)
Have multiple incentives available. As you get more sophisticated in targeting stuff which you make towards customer segments or particular customer needs, it makes less and less sense to give everyone the same offer.
Let me ding myself for this one: I presently have exactly one entry point into my main email list. It offers a video on optimizing the first-run experience of a SaaS application. When I first published that I was pretty proud of it, but it covers only a small portion of what I write and speak about. I might get the opportunity to speak at a conference about e.g. SaaS pricing grids, and "Thanks for listening. What a fun topic! If you want to hear about something completely different, give me your email." is not the most natural call to action for the last slide of that presentation. One of these days when I have a bit of time free I'm going to either create or repurpose five-ish pretty in-depth guides on particular software-oriented topics, so that I generally have a compelling offer at the ready for new posts / presentations / videos.
People at larger organizations in particular please pay attention to this. You might be under the misapprehension that you can have multiple teams coordinate their release schedules so that you get e.g. a blog post, an incentive, and an email campaign all ready on the same subject at the same time. This almost never works. It is far, far easier to develop a catalogue of incentives and a catalogue of e.g. email courses and then just have the folks in charge of producing things pick whichever offers they think are most appropriate to the thing they're working on. This increases the pace at which you successfully ship things and will reduce scheduling conflicts and stress.
As long as I'm on the topic of customer onboarding in SaaS applications: Samuel Hulick owns that space these days. I really like his work, partly because he came out of nowhere one day and wrote me "It seems like nobody writes about SaaS onboarding. Someone should. That someone is going to be me." I appreciate the pluckiness there, because Samuel did not get into the paralyzing "But I'm not really an expert! I just know some stuff!" attitude that often makes folks fail to share their knowledge with people who would benefit from it. Most people who write on subjects are not The Certified Expert on them. God knows I wasn't when I started writing and, for that matter, still am not. But since you've got to start somewhere, start somewhere. Besides, given that there's a nearly boundless and expanding multitude of topics to work in, just planting your flag on a subject and then working on it in an intelligent and sustained fashion for a few years often actually would make you The Certified Expert on it. It's not like they offer PhD programs on SaaS app user experience -- the folks working on moving that field forward are moving into terra nullius practically every day. (Samuel has a book out, by the way. It's a no-brainer if you run a SaaS app.)
Align incentives with the conversation you're going to have. It might be obvious, but obvious advice is often valuable, so here we go: if the top of your marketing funnel is friendcatching work about X, and you promise people a guide about X in return for their email address, you should prefer sending them initial emails about X-like topics as opposed to email about Y.
This can take a bit of work, but if you're smart about your email strategy, you can make the work a little less daunting. For example, if you sell your software in 12 distinct verticals, writing 12 distinct email campaigns for each vertical could probably occupy your email expert for half of a year. Rather than doing that, instead create the skeleton of an email campaign (say, a one-month email course on accounting in $INDUSTRY) with 75% of the emails being about generic accounting issues and 25% of them being specific to the core unique concerns of $INDUSTRY.
One of the beautiful things about email marketing is that customers only see the small slice you expose to them rather than all of your email marketing in parallel, so a customer only seeing your emails about "accounting for consultancies" would come to the (accurate!) conclusion that your company knew a lot about accounting for consultancies.
Since most of you don't actually have any email strategy, though, let me recommend that you actually start sending email prior to worrying about mass-customization and segmenting your emails. (I've worked with maybe two dozen B2B SaaS companies operating at admirable levels of sophistication. Only the top five were at the point where they'd really benefit from having multiple email funnels. But hey, if you're one of the companies up in those rarefied airs, get on it -- a modest boost in your conversion from email subscriber to lead for your software pays for the effort several times over.)
Build internal libraries of your best work and use them for remixing. One of the classic conflicts between artists and audiences is that the artist is perpetually engaged with their art and so always wants to be breaking new ground, but the audience is made of individual members who individually have far less engagement with the work, and they often are best served by art which is, to the artist, old news. Stan Lee used to tell artists at Marvel "Remember, every issue is someone's first and someone's last."
Unfortunately, in comic books, that results in decades-long statis for characters. You don't have to bore yourself to death by covering Lois Lane getting kidnapped by someone wanting to hurt Superman again, but you'll probably want to reprise topics more often than you're naturally comfortable with.
This counsels having a back catalogue of your best work, hopefully in a format which is easy to re-use internally. For example, you can pull information out of e.g. a case study which you published with a particular customer and re-use that as part of an email course for people in their industry. You can revisit old articles to inform podcast conversations. (Bonus points: you can revisit comments people left on old articles to inform podcast conversations. This rewards people for keeping engaged with you and simultaneously guarantees that you're talking about things that people outside your own building actually care about.)
In addition to being strategically lazy in the finest tradition of the best engineers, this gives you the opportunity to get ongoing value out of one-off expenditures of effort. For example, if you do conference presentations, the conference presenters will often arrange to have them videotaped. Conference presentations are some of my best work, so I always ask for a copy of the videotape afterwards. This lets me add a transcript to the slides and video, and then for only an hour or so of editing, I get to show that presentation to an audience many times larger than the size of the room I originally presented in.
Bonus points: conference organizers will love you for doing this. Their main business concern is selling out next year's conference, so evidence that last year's conference was awesome helps them tremendously. Many software companies have to scramble like mad to get RFPs responded to to get speaking slots, or they explicitly buy speaking opportunities via sponsorships. Instead, just make a habit of delighting the organizers by giving them a shoutout when you remix your conference presentation into post-conference opportunities. Conference organizers, like folks in every industry and trade, talk to their buddies about what/who worked out and what didn't at their events. Every time I publish a previous speech I get inbound interest for further speeches. If this accomplishes business goals for you, this gives you a straightforward and repeatable process for getting those opportunities. (The primary thing I "sold" via speaking, back in the day, was consulting engagements. There exist many, many software companies which add five or six figures of yearly revenue for every hour they get in front of a trade audience, though.)
Having a library of components which you can remix as appropriately also helps to avoid one of the pathologies of content strategies, which is talking way over the heads of your audience.
Experts Do Not Only Write For Experts
I'm indebted to Aaron Wall for this insight: most people in a given market are not experts. This is particularly true for the most interesting slice of software markets, which is "People who have enough budget to buy a software product but not enough budget/need/sophistication to hire a team of engineers and scratch-build a custom system."
Those of us who are building businesses are generally either experts or soon-to-be experts with regards to our problem domains. We often produce work targeted at an audience which is at our own level or slightly above it. (I have a bad habit -- I sometimes thrown in phrases purely because they pattern-match with "things that would really please my English teacher." Terra nullius.)
There's certainly a place for expert-level writing. It helps you connect with other experts, it gives your entire body of work the expert imprimatur even when the instant work is not expert-level, and it satisfies the desires of an important sliver of your audience. Just remember that, in most cases, experts are only a small fraction of the audience.
(I'm speaking of expertise in your problem domain. Your average customer has forgotten more than you'll ever know about their main problem domains, and woe to us entrepreneurs who forget this. I recently had the surreal experience of fielding a question about Heartbleed from someone who doesn't understand SSL but has intimate experience with cardiac hemorrhaging. Just because they're new to your particular slice of the world doesn't mean that they're idiots.)
Concretely, for your content strategy, I'd strongly advise:
High-quality beginners' guides: They spread tremendously well, are often structurally guaranteed to be evergreen (since the basics of most fields change much slower than the best practices among the experts), and encounter customers at a point where they're very malleable in their approach to your space. If you get folks early, you'll often have the opportunity to influence their take on your business for years to come. (A great example of a beginner's guide is the Beginner's Guide to SEO, a Moz production which is one of my go-to recommendations for people looking for a single good entry point into the space.)
Next steps for intermediate learners: One of the problem with beginner-focused writing is that almost anyone can produce it and, as a result, the marketplace is often very crowded with information which is theoretically responsive to their needs. Additionally, beginners often aren't qualified to separate wheat from chaff, so entire fields get clogged up with low-value listicles (10 Amazing Tricks The IRS Doesn't Want You To Know!).
Meanwhile, it is both harder to produce things which meaningfully make a dent on an intermediate user's understanding of the problem space, and making a dent for them might matter more for your business. Beginners are often (not always) less senior folks in the organization or less inclined to spend money on solving their problems. People with intermediate expertise are often aware of how hard-won that expertise was and how valuable the problem space is, so they're willing to actually spend money to improve their results. This often makes them extraordinarily lucrative as potential software customers. (You can frequently position your software solution as a compelling alternative to hiring an external expert.)
Dedicated task-oriented content: I've written a lot about scalable content creation over the years, but it occurs to me that this is most important for when your writing is directly responsive to a task that someone knows they have to do. "Make our business more secure" is not a task. "Configure a Cisco router to open up HTTP" is a task.
Google has enormous volumes of people who come to it with task-oriented needs. They're often seeking solutions which you could describe for an entire universe of tasks in an efficient manner, using data which you already have in your business or which would be cost-effective to collect.
I've covered this topic extensively, since it basically ran my business for the first several years. The best single entry point is the articles about Content Creation on my Greatest Hits page. (Speaking of which -- if you do anything, make a curated list of the best of everything you've ever done. It's very little marginal work for surprising amounts of marginal benefit. That page does everything from making my morning email rounds easier -- "Yeah, I've written about that topic before, see copy/paste link" -- to functioning as a surrogate CV to giving me an easy way to flow algorithmic signals of authority to pieces which I have particular reasons to want to highlight.)
What I've Been Working On Lately
As alluded to above, it has been a while since I've had sustained time to sit down and write. Sorry about that -- I really do mean to get these out on a plus-or-minus biweekly basis, but I've never been able to carve out the time for it consistently.
Anyhow, two things:
I recently wrote a pretty in-depth look at Tarsnap's business. Tarsnap is an enormous technical achievement created by an Internet buddy of mine -- it's the only secure backup service worth using. Unfortunately, the technical achievement is being underserved by the marketing and positioning, so I took a whack at improving that. Some of the lessons generalize pretty well, so if you're interested in software businesses I'd encourage you to take a look.
I have been hard-at-work on the upcoming course about conversion optimization for software businesses. You'll hear more from me in the next few weeks. I appreciate your patience -- business and personal things have thrown more than a few wrenches at me, but it is getting closer to shipping.
As always, if there's anything you'd like to hear about in more depth, please feel free to drop me an email. I'm in heads-down-ship-all-the-things mode for most of the next month, but I'll read them all and try my best at responding.
Until next time.
P.S. Rand Fishkin, one of the co-founders of Moz, had a really excellent presentation recently on failure modes for content marketing. It is fantastic. You should, in particular, pay attention to the points made about "amplification" (starts on slide 48), which is his term for the post-creation marketing of your work to encourage more people to see it. Failure to do this causes a lot of really good work to languish in obscurity, where it neither helps the potential audience nor the business which underwrote its creation.