Last time I wrote about Marco Arment selling Instapaper to Betaworks. I talked a little about Marco’s state of mind and a few of my own thoughts on that. I can relate to Marco’s feelings as I have had many of them myself.

At the end of the day what I believe every independent (indie) developer wants is financial security and the freedom to work on whatever interests him. I’m not sure Marco makes this same decision if he doesn’t have income coming in from other places.

Let me be clear that I have no insight into Instapaper’s revenues and Marco hasn’t talked about them specifically. Maybe the revenues, in the face of competition, has dwindled to the point where the revenues aren’t helping that much. But when it comes to indie developers, sole proprietorship in general, every extra dollar helps and diversity of income is critical. If The Magazine revenue drops then blog revenues are there to pick up the slack. Marco, on the surface, has four revenue streams that all related to each other: a blog, a podcast, The Magazine and Instapaper. All were geared around reading and listening. They all appealed to the same audience and thus could cross-sell those services. He has dropped one of those — or at least now has less of a stream from it — meaning at least in the short term his stool has three legs instead of four.

The financial security earned from a combination of revenue streams means almost everything to an indie dev. It is the backbone by which creative security is built. After all, if I need to make money to pay the bills then I am beholden to other people to earn that money, whether it is a job or contract work or something else. That financial security enables folks like Marco to do whatever he wants. There is nothing like knowing that you have less than three months in your personal bank account. It makes it nearly impossible to focus.

Marco talked, on various podcasts, about the stress and guilt of Instapaper. The stress of working on a product he no longer wanted to work on, the guilt of ignoring his customers, and feeling this way when he has had so much success. That, too, is palpable. I’ve spent plenty of days stressing over the code I can’t bring myself to touch. The motivations are done, whether it is because the app isn’t making you any money or because the code is old and break-prone or because heart and sole was already dumped into the project long ago and there is just nothing more to give. I think, give it a week, give myself a break. But a week passes and I’m still not ready to touch the code.

That’s when the spiral happens. The guilt over not touching it takes my brain to bad places which makes it even harder to focus on touching the code. Breaking that spiral is nearly impossible. And when coupled with the constant 24 hour a day worry over the servers going down, a worry that plays in the brain all night, a worry that keeps the head awake even when the body needs to sleep, well, there is no recovery from years of that. There are plenty of mornings I wake up at 6am after 8 hours in bed and feel like I just did an all-nighter. After four years, that gets really old.

The catch to all this is that there is a clear path forward for Instapaper, one that could potentially provide the security Marco, I believe, is looking for. More on that later. But maybe the stress and guilt had gotten to be too much. Maybe Marco just felt like it was time to do something different. That’s okay, too. I know I’ll be watching closely to see what it is.

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This concludes Part 2. Part 1 | Part 3

Marco Arment sold Instapaper.

Boy, did that take me by surprise but since the news came out and I have had a chance to listen to Marco talk about it in his own words, I am less and less surprised. Instapaper, the read-it-later app, was an early mobile web pioneer. From the beginning is a web app that made the content fit the screen (not a desktop web app that could run on a mobile screen). Now we call this responsive design and it is everywhere. But back then a website designed for the smartphone screen was rare.

In 2008 when Apple opened up the iPhone for apps, Instapaper was there on day two or three. It was a huge success, as so many apps were back then. Six years later and the app is still strong but has some mighty powerful competitors, all free and backed by big money. (Instapaper is $3.99.)

As Marco explained, he was burned out and guilt-ridden. Every day he would wake up worried that a competitor had wiped out his business. Every night he stressed that a server would crash and he wouldn’t wake up to fix it. He was guilty about not getting updates done, guilty about angry customers, and even guilt about his own complaining when he was successful [1].

The good news for Marco is that he was clear about what he wanted: to run a small business, feed his family, and not have any employees. And it was clear to him that Instapaper required more than what he could provide. So he spent time and found Instapaper a home at Betaworks. There’s security here: Instapaper and its customers have found a home where the app won’t be sunset and Marco knows that the residuals from Instapaper, revenues from The Magazine, and income from his blog and podcast will help keep him and his young family afloat.

I hope he doesn’t regret this decision. It is painfully difficult to build an app with the success of Instapaper. I believe he owes his success with The Magazine to Instapaper. And I believe there was a clear road forward for Instapaper, one where subscription revenues could play a big part. Could he have found an independent non-employee employee to help with the next generation of Instapaper just like he found in Glenn Fleishman to help with The Magazine? I believe so, if he wanted to look.

Another thing to factor in is that Marco and his wife had their first baby within the last year. If I learned anything from having two kids, never ever ever make life changing decisions during that first year. The brain is just not right. The adjustment to parenthood, the sleepless nights, it just makes for some funny thinking. I hope Marco doesn’t regret the move later, when his brain returns from Fuzzyland.

I have more I want to write on this. Marco is so open with his thinking and feelings. Plus I think there is a clear path forward for the service, one that can generate the kinds of revenue security most people would die for. (Not most of us crazy entrepreneurs but most indie developers and normal human beings I know.) Those topics will have to wait for another day.

In the meantime, good luck Marco. I hope you find the next big thing for you. But it won’t be easy. As you said yourself, you couldn’t have done Instapaper today. The time to build from website to iPhone app to iPad app to Android app, the build up of services, just aren’t available to indie developers today. Today he would have needed money and staff, both of which are things Marco has no interest in dealing with.

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This concludes Part 1. Part 2 | Part 3

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[1] This is a Midwest thing. Like Marco, I too was born in Ohio and all too familiar with this feeling.

Really smart article by Ben Thompson:

There is a “Mobile Hierarchy of Needs”, and understanding what needs have already been met, and by who, helps clarify the current basis of competition, who the relevant players are, and who is winning or losing.

Now Ben’s talking about platforms (iOS, Android), but every developer I know (or at least the smart ones) are looking at the relatable tier (services) and asking how they play there. The prices in the market for one-off revenue are suppressive, perfect for hobbyists and no one else. The only future is recurring revenues, at least if the goal is to build something sustainable. So far I’m hearing a lot about three models: ads, subscriptions, and in app purchases, where in app purchases aren’t “buy once and have forever” but where in app means selling the same or new things to the same customers over and over again. I’m waiting to see breakthrough revenue models as well.