You are seemingly only permitted to be positive. This is the case not only for entrepreneurs but true for anyone: job seekers, execs, managers, you name it.
Having doubts or problems is an inescapable part of life, yet our public lives aren't permitted to reflect this reality. We need to masquerade: happy, motivated, fearless. I myself have agonized over this regarding my blog. As a participant it the job market, I can't shake the fear that saying anything negative will hurt my prospects in whatever path I may choose.
This dissonance with reality, the need to deceive not only others but yourself is at best tiring and at worst torturous.
People dig the truth, and the truth can be rather damning and quite negative at times. Some of my posts which get the most attention are from that general perspective.
'Google's "free food" is not free' got a lot of responses right here on HN, and that was a post about exposing something which happens in the recruitment pipeline.
People have come to me offering jobs and seeking custom work as a direct result of reading my posts. I just don't see the connection.
Loved reading the article (thanks!) but even this article flips the the lack of mastery on its head by expressing the author's enthusiasm for progress, his implied conviction of future growth, and a supporting cast that will help him get there. The negativity serves as a literary element to highlight his positive attitude and optimism.
What if he felt truly overwhelmed and hopeless, having lost key team members to a freak accident or freak legal issues? Would he be able to post expressing his purely hopeless despair? I doubt it :(
In my opinion, "time" is the biggest one; he mentions it first, but I don't think the gravity is expressed adequately. I have time to waste on HN because I spent a year and a half building the one I'm on now; at this point a blog... just doesn't matter. That's most certainly not meant to be a general comment, but in my case, time was a problem to the point where, once it wasn't (as much), a blog was no longer valuable.
Whether it's valuable or not is highly dependent on your product, your goals, and your audience. I don't think there are many areas where it's totally worthless, but if you're actually an entrepreneur and not just tentatively trying something out and looking for backers, in my experience it's hard to find enough time to both blog and promote your blog unless you're either a minority-share-of-the-grunt-work partner or already so plugged in to some popular scene that you don't actually have to worry about the exposure a blog would otherwise be intended to bring.
I guess the point of this is that "I can't blog" is the equivalent of a first-world problem in a first-world profession: If you have the time and/or connections to do it and make it effective, it's likely you'd succeed in a very similar way without it.
The problem is that when you are a startup founder, most of the things you deal with on a daily basis are confidential.
You're doing it wrong. Either you're too paranoid, or you're focusing too much on confidential stuff. It's not like your company develops stealth technology for the military ("Swedish one stop bargain shop on the web"). There must be an infinite number of industry insights that you can share.
As a CEO, one good reason to blog is to be perceived as a thought leader in your space. One of the reasons Silicon Valley is a successful technology hub is all the shared knowledge. Many successful entrepreneurs here may not blog that much, but they do share insights through interviews or talks. Others (like Paul Graham) enjoy writing, and they share unique knowledge. Are you keeping this kind of knowledge to yourself because you believe it's a competitive advantage?
Startups are small, and so is the startup world. Personal lives and professional lives are very much meshed together, and as business is a purely social occupation, burning bridges is pretty much the worst thing you can do.
So if you blog about how you solved a conflict with employee X, or how your talks with fellow entrepreneur Y went, chances are a) they read your blog/twitter/HN comments/etc. and b) they'll realize you're talking about them, and most won't appreciate it. This is typically undesirable.
So no, you're not developing military grade technology, but it's not about paranoia either.
Similarly, if you blog about how you're having problems {growing your userbase|scaling your product|etc.}, it pretty much guarantees that your investors will get scared. "Hey, you're telling the world you're encountering problem P, but your competitors aren't! [it's just because they were smarter than you about that] Why should we trust you with our dollars?"
Conversely if you blog about how awesome your company is and how everything is peachy, no one will care, so what's the point?
I agree with the general premise of your last paragraph; that being said, you'll notice that a lot of entrepreneurs giving talks do so after they made it big, and that people like Paul Graham aren't CEOs, so they don't share the same incentives and fears.
I don't think anybody is saying that there isn't some confidential stuff that you shouldn't blog about. But if most of what you are dealing with is so confidential you can't talk about it (even if you have to redact some details), I agree that that sounds a bit dodgy. Besides, what are the chances that anybody really wants to read about the mundane day to day operational stuff anyway? Unless there's some bit of salacious gossip in there... but us humans get get our fix of salacious gossip from People or Us or somewhere else.
Similarly, if you blog about how you're having problems {growing your userbase|scaling your product|etc.}, it pretty much guarantees that your investors will get scared. "Hey, you're telling the world you're encountering problem P, but your competitors aren't! [it's just because they were smarter than you about that] Why should we trust you with our dollars?"
Feh... your competitors probably are having the same problem, and being more open about things shows that you have the confidence to be open, which - to my way of thinking - inspires more confidence, not less. If people are keeping secrets, I wonder what they're hiding. If they're being open and transparent, I can see what's going on, see what progress they're making, etc.
The guys from PMRobot made a really fascinating post[1] a while back, touching on the whole transparency thing. It inspired us to do the same thing[2], and I have to say, it felt good and I think it's the right thing to do in the long run. Besides, anybody who might want to invest in us, but chooses not to because of a blog post, was an investor we didn't want to begin with (disclaimer: We have no outside investors at this time and aren't seeking any).
You obviously did not read my blog while I was CEO of IndexTank, a funded startup acquired by LinkedIn. I found plenty to blog about, and many of my posts were on the front page of this site.
All the petty things that you mentioned happen to most startups, and don't usually make for interesting posts. That's my point about the OP.
As a first-time entrepreneur, I do have a blogging dilemma but it isn't related to confidentiality. My problem is that I both don't have time, and don't know what I am doing.
Everyday is a struggle to figure things out as fast as possible. Given the situation, I can either (1) blog about how I am struggling during the struggle, or (2) move forward as fast as possible without wasting the time it takes to write and manage a blog.
Lately, I have opted for (2) with the hope that I will be able to blog more meaningfully with some real experience under my belt.
While a public medium like a blog may not always be appropriate, writing about your struggle can often help you formalize the problem, reason about it in new ways, and suss out solutions. While grappling with the problem, quietly thinking, listening to music, coding, writing, talking, sketching -- each seems to recruit different aspects of the problem-solving engine.
There is something to the idea of "rubber duck debugging", especially if you're on a very small team, or a team of one.
I wonder how the rate of blogging among startup founders relates to the average blogging rate among other people (IE, more or less). Based on the upvotes I'm guessing a lot of people relate to this, but I'm not sure I'm convinced that startup founders blog less than the average person.
Personally, the reason I don't really blog is because what you write on the internet is (mostly) permanent. I tend to subscribe to the notion of "strong views, weakly held", but the transient nature of that philosophy clashes with the permanency of publicly stating an opinion that's easily searchable and indexable. I think at some point culture will catch up and we'll recognize that what people wrote five years ago isn't necessarily representative of who they are now, but I'm not sure we're there yet. So I avoid blogging because I don't want to burn bridges because I wrote some rant that in a years time I don't even agree with.
Emphatic disagreement.
The more I talk about what I'm working on at Wellposed,
the more I talk about how I'm solving problems, etc, the more opportunities I've stumbled into / potential customers I've found.
Amusingly, I've actually had more and more requests over time to start blogging about even the parts of my technical work that I'd consider pretty unsophisticated!
Point being (as businessy as this may sound), the more channels you have to engage with your customers in a positive, engaging, informative (and hopefully educational) manner.
I'm pretty sure that every business that is doing something sophisticated benefits from providing more channels for passive customer discovery and education. (or so I'd hope!)
That said, it could be argued that I've a pretty unusual business so I may have have opinions that won't make sense for normal businesses.
Why are you blogging? If you're blogging strategically, you should be trying to establish yourself as a subject matter expert in your startup's field. The best way to do so, which is beneficial to you AND the community, is by giving away for free useful information (insights, advice, analyses, etc). So, just choose useful information you happen to know that is not confidential - I'm pretty sure every founder has got a lot of that. If the insights come from real cases that you'd like to recount but you can't discuss publicly, anonymize them.
EDIT: The real dilemma - but the author barely scratches the surface there - is time. How much should you devote to writing vs to developing your business? I don't have an answer here, but I'm seriously thinking about hiring someone to help me there.
OKCupid was great for this in the early and middle days. They'd present a lot of analysis that showed some particular group of insights based on their data. This was before 'big data' was on the CEO's radar and, even with the presentation of their analytical methods, had a feel of 'magic'. It also increased confidence that, if they could use their data to find out and disclose actionable ways in which people could increase the probability of success, they would be able to generate more probably matches than their competitors.
A similar example, Wolfram's team has moved a number of similar posts from the journal and other channels to the blogs, and it's fun as well. They keep it light-hearted in tone but show off some of the "look how easy this is" with the system.
What I like about the Mathematica examples is that they are reproducible by anyone with the software (OK, a non-zero barrier to entry there) or, with effort, the time to write the part of the stack employed in the solution.
This is an awesome way to generate 'popular' interest while marketing your product. Coupling this with Wolfram waking up and offering the 'Home Edition' for some of their products and they're rebuilding a base that has been eroding since mma was de-emphasized in University educational programs.
You don't have to blog exclusively about your venture, surely? There are countless topics out there in your industry and others, nice features you've seen in other products, etc.
(Note: I'm going to put links to my own posts here, not to be blatantly self-promotional, but to illustrate points I'm talking about, since the topic of this discussion is blogging. Feel free to ignore the links).
I've been blogging more than ever lately, and - FWIW - here are my observations:
1. Time is my biggest "problem" vis-a-vis blogging. Given everything else I could be doing with that time, it's sometimes hard to prioritize writing a blog post over writing code, or any number of other things.
2. There's not a lot that I want to write about, but feel constrained from writing about. We haven't had a lot of internal co-founder drama or turmoil, or any inter-personal scandals, or especially bad relationships with investors, customers, media, etc. so there isn't a whole lot that I have to restrict myself from talking about from the "avoid upsetting people" point-of-view.
3. That said, I do sometimes write a post[1] that challenges something somebody else said, or is a bit argumentative or controversial. A good recent example was when I read a WRAL Techwire post by Joe Procopio, took it one way, and sat down to write up a testy response. But then I emailed Joe to say "Hey man, I read your article, and I'm thinking about posting this in response, do you have any comment first"? He replied, clarified some points, sent some links to other works, etc., and I rewrote a big chunk of the post. The spirit of the post remained the same, but it became less of a specific response to his article, and more of a general observation / commentary. So no hurt feelings or conflict needed.
4. The blog is marketing. Blog posts are a way to drive traffic to our site, gain search engine positioning, achieve TOMA, establish credibility, etc.
5. I feel that I need to stop writing about "startup stuff" so much, because writing about startups isn't doing anything to drive revenue for us. It's time for us to focus on blogging stuff that will attract our customers to our site, by writing about: the industries we are targeting, the executives we want to attract attention from, the kinds of problems we are working on solving, etc. The blog is content marketing, and people who want to read about startup drama just aren't our customers. People running plants making nonwoven technical textiles, or furniture, or farm tractors, etc., are customers. Ergo, we need to write about the nonwoven technical textiles industry, the furniture industry, or the farm tractor industry, OR something that will be relevant to people in those industries. So, for example, if we want to get our message to CIOs, CTOs, IT Directors, etc. we write posts like this[2] and this[3].
6. The blog is a form of "market education". So it's important for us to blog things that educate the market in a way that helps align them with what we're trying to do. We are working on incorporating a specific methodology into how we engage with customers, so we write blog posts that explain it and advocate for it.[4][5][6]
7. I'm not a big fan of "newsjacking" per-se, but if there's a topic that is "in the news" AND I happen to actually have a strong opinion on the topic, I like to write about it[7][8]. It's usually good for getting traffic and sometimes it leads to an interesting discussion. And, per The Cluetrain Manifesto - "markets are conversations".
8. Sometimes it's cool to just have fun and post something kinda random or seemingly silly.[9]
9. I wouldn't have a problem blogging about some aspects of our strategy, and we do strive for a high level of transparency. Heck, we're an Open Source company, so we have to be transparent to a certain point, by definition. But there will always be some secret sauce that we don't go around telling everybody. And that's fine. Nobody says you have to blog everything.
Perhaps a dumb question but what is TOMA? I google'd and Urban Dictionary'd and I came up with the "Tennessee Osteopathic Medical Association" which my gut tells me is not what you're trying to achieve.
Thanks for clarifying.
BTW, #5 point is great. I've thought about writing posts that I thought might "do well on HN" but in retrospect, I stopped myself because realized our demographic isn't HN and so even if #1, it'd be a waste of traffic (except from a recruitment perspective perhaps).
TOMA is what's going on if I ask you to "name an American car company" and you immediately reply "Ford". And chances are you will say "Ford" and not "Buick" or "Chrysler" or whatever. Ford have done a good job of building TOMA. Likewise if I said "name a carbonated cola", it's a lot more likely you're going to say "Coke" than "Mr Pibb".
Having doubts or problems is an inescapable part of life, yet our public lives aren't permitted to reflect this reality. We need to masquerade: happy, motivated, fearless. I myself have agonized over this regarding my blog. As a participant it the job market, I can't shake the fear that saying anything negative will hurt my prospects in whatever path I may choose.
This dissonance with reality, the need to deceive not only others but yourself is at best tiring and at worst torturous.