I recently installed a media sharing app to one of my servers. It was simple to install, but it hid a dastardly trap for long-term maintenance.

Every time a user uploaded a file, the web app saved it to the local filesystem. If I ever blew away the server and rebuilt it, I’d have to backup and restore every file manually. The better architecture would be for the app to write its files to a separate storage server, but I didn’t want to spend months rewriting the app to make that possible.

Prior to February 2019, I published all my retrospectives on Indie Hackers:

• Is It Keto Month 3: Returning to a Site that Grew without Me

I wish that I had found this book nine years ago. It taught me a great deal about choosing the right product to build and the advantages of targeting small niches. The author makes compelling points about the importance of marketing and small founders’ common pitfall of treating it as an afterthought.

Unfortunately, much of the content aged poorly. Published in 2010, Walling intentionally kept the book pragmatic, recommending specific tools and strategies that were popular at the time. Reading it in 2019, many of the services he recommends are either irrelevant or dead. It would be nice to see an updated edition, which Walling has suggested is a possibility.

Congratulations! You’ve finally written so many lines of code that you can afford a beach house. You hire Peter Keating, an architect world-famous for his skyscrapers, who assures you that he has brilliant plans for your beachfront property.

Months later, you arrive at the grand unveiling. Your new home is an imposing five-story behemoth of steel, concrete, and reflective glass. As you pass through the revolving doors, you track sand onto the opulent marble floor. Inside, you find a reception desk backed by an elevator bank. Upstairs, your master bedroom and three guest rooms are just four adjoining office cubicles.

Many software founders fail for a simple reason: they ship too late. They spend years developing a product in a vacuum only to see it crumble the first time a real customer touches it.

The Indie Hackers podcast features many such stories. The show’s stated mission is to help listeners learn from the mistakes of startup founders, but host Courtland Allen frequently expresses existential angst about whether this is even possible: