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How to write good startup advice articles

Startup articles, much like some other content niches, have a tendency to be addictive but content-free. Everyone is guilty of doing it. I've done it too. I don't think there are any regular authors of startup-related article who don't sometimes produce articles which are perhaps entertaining, perhaps even enticing, but which add nothing to the reader's life.

Those articles are, by definition, a waste of time.

Since I spend a lot of time both reading and writing startup articles, here are some key points to bear in mind if you prefer to write articles of substance, which others can learn from and apply in their own startups.

1. Avoid over-generalisation

The most common flaw of pointless startup articles is over-generalisation. Entrepreneur brains are by necessity obsessed with finding patterns in chaos. That's what we do every day. So it's natural that we see many patterns that look like they could be general rules.

A wise man once said, "the plural of anecdotes is not data". When writing a startup article, be very careful not to extrapolate from one experience that happened to you to a general rule for startup. "X startup mistakes" or "Y startup tips" like this one (written by me a long time ago) are basically collections of generalisations based on personal experiences. Some of your points may even be correct by sheer luck, but the short-form nature of a list of tips means that even those don't have the necessary context to be really useful.

2. When talking about personal experience, include context

Some parts of running a startup can be analysed scientifically, but a great many cannot. You cannot a/b test your ability to close a sale in person. You cannot a/b test your pitch to Paul Graham on YC interview day. Each sale, each pitch, anything involving person-to-person contact is unique. Some general principles may apply, but unless you repeat the process a lot (e.g. you're a sales person who has pitched 500 enterprise customers), it is very hard to come up with any kind of reliable "law".

Even things that don't directly involve people are often contextual. "The best technology to build your statup" depends on the kind of business you're building, the sorts of products you're considering, available talent nearby, your long-term objectives, your budget, and so on. And it will change year by year, if not month by month.

That's fine. Not every post needs to be declaring a new law of nature. But when you post something which is a personal experience or opinion offered up to others, be sure to include as much context as possible. Otherwise, people will not be able to properly make use of it, because they won't know if it might apply to their specific context.

"This is what you must do so that your startup can be successful" is useless. "This is what I did and it helped my startup succeed" is marginally less useless. "In this context, I did that and I believe it helped my startup be successful" is potentially useful.

You don't need to preface every sentence with "I believe" or "in my experience" - doing that will make your writing weak. But make sure you give the right amount of context, and qualify those of your statements which are really just wild guesses rather than tried and tested theories.

3. Avoid posts with no actionable points

Posts like this or this, listing attributes of successful entrepreneurs, or programmers, or businesses, or whatevers, are not actionable. They're just entertainment - possibly even a damaging form of entertainment, since they contribute to the myth that successful entrepreneurs are heroes and goddesses that are out of the reach of the common man.

Whenever writing up advice for startups, ask yourself "what do I want readers to change about what they do after reading this?" If the answer is "nothing", your article is entertainment, not advice. If the answer is not "nothing", then make sure the advice is clear to the reader by the time they reach the end of your article (even if they skim!).

4. Be brief, but not too brief

Entrepreneurs are busy people. The ones who most need your advice are often juggling a full time job along with their startup. They don't have the time to read a 3,000 word rant in order to extract a couple of meaningful points. Be respectful of your readers and their limited time.

After you've written your article, but before you post it, ask yourself "is any part of this outside the scope of this article? is any part long and rambling? is there any section that I added just because I wanted to talk about it, rather than because it's useful?" Cut mercilessly.

At the same time, don't cut too much. Seth Godin's blog is a good example of advice that's been cut down so much that it becomes useless. Startup advice is only useful with context. If you cut the context out, you might as well not post the article. (of course, Seth's goal is probably not to post startup advice, but merely to maintain readership so he can sell his books)

If you just have too much content and all of it is relevant to your points, you're trying to make too many points. Break the article up into several articles in a series. As a bonus, this is said to be good for getting RSS subscribers...

5. Present your article properly

Presentation matters. If you wrap your life-changing, mind-expanding point in a badly formatted post on a generic wordpress (or posterous, or tumblr) blog, you are hurting your chances of making a positive difference. Make sure your article comes in a credible package.

Consider also the visual appearance of your article before you post it. It should be clear, at a glance, what the article is about. It should not look daunting, with huge paragraphs and no subtitles. It should be possible to skim it and still get the gist of it.

In conclusion

If you have advice that you'd like to share with the community (and many entrepreneurs do), try to follow these points when doing so:

  • Avoid over-generalisation so you don't give thoroughly incorrect advice by wild extrapolation
  • Include enough context for the reader to be able to decide whether this applies to their context
  • Avoid posts with no actionable points: they are just entertainment, not advice.
  • Be brief, but not too brief. Respect your readers' time, but include enough context to be useful.
  • Get the presentation right, so that people take your article seriously and can read it efficiently.

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What being on the front page of HN will do for you
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