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People keep asking whether Overcast is the original name I wanted, or the alternative I picked to avoid a potential trademark conflict, a process I had tweeted about a few months ago.

It’s the original one I wanted.

The naming process might be interesting to other people, though, so here’s what else I came up with and why I decided not to use any of them.

I brainstormed many potential names in a giant text file over a couple of weeks, enlisting help from friends, Invent-a-Word, Wordoid, and lists of English prefixes and prepositions. Even if I knew a name was bad or unusable immediately, I still wrote it down in case it could later inspire a usable variation.

Instacast was taken, of course,¹ but I wouldn’t have used it anyway. A business of mine that has nothing to do with Instapaper shouldn’t have a name that suggests otherwise, and the “insta-” prefix is so crowded today that I don’t think any new products should be named that anymore.

I was looking to satisfy as many of these as possible:

• Memorable
• Short
• Easy to pronounce
• Easy to guess its spelling if you heard someone say it
• Related to podcasts somehow
• Available on Twitter
• Domain available on a major TLD like .com or .net, or at least .fm
• No trademark conflicts
• Not too crowded of a meaning in Google

Naming a podcast app is tricky. First, I went through words ending or containing “cast”. Here were the top contenders:

• Monocast: This was my chosen backup if I couldn’t get Overcast. It’s audio- and podcast-related (and most podcasts are mono), short, easy to remember, easy to spell, and easy to pronounce; yet it’s not a real word, so it was available everywhere except Twitter — I even registered monoca.st and bought the .com from a squatter for $750 because I was so sure I was going to end up settling for this name. But it wasn’t memorable and, somewhat fatally for a podcast app, evokes poor sound quality.
• Castaway: My original prototype was named this, but it’s a bit lonely and sad, there are tons of conflicts, and I’m afraid of movie-studio lawyers.
• Procast, Protocast, Ultracast, Viacast, Unicast, Epicast, Outcast, Polycast, Transcast, Upcast, Hypercast, Bitcast, Omnicast: Boring, undifferentiated, a little too geeky. Many of these already had computer-related meanings or uses. Some had fatal trademark conflicts.

Since the app has a server component, I explored more cloud-related names (which is what originally led me to Overcast):

• Nimbus: A top contender. A few conflicts, but nothing fatal. The cloud relationship is good, but I was afraid people would have a hard time spelling or remembering it since it’s not a commonly used (or known) word.
• Nimbostratus: Same benefits and drawbacks as Nimbus with fewer conflicts, but longer, harder to remember, and harder to spell.
• Overadio: .com available, but a bit too weird for me.

Since I didn’t have a lot of good options, I took a different route: trying to evoke qualities of podcasts or the experience of being a podcast listener. But it was hard to find words that didn’t also evoke loneliness and weren’t already taken.

I tried references to dialogue and commentary:

• Comment or Commentary: Both .fms were available, but I hate web comments, so I couldn’t get excited about this homonym.
• Remarks, Analysis, Debate, Articulate, Pronounce, Rhetoric, Eloquence, Dialog, Dialogue, Audience: None stood out, all were very crowded, and some had fatal conflicts.

I then explored terrestrial radio, audio hardware, and mastering:

• Headphonic: One of the only good names that didn’t contain “cast”. It was widely available, and I love the headphone reference, since podcasts are so often heard through headphones. But it’s hard to spell — it’s the kind of name that you couldn’t just tell someone about aloud (such as… on a podcast) without also spelling it out. And, fatally, it was uncomfortably close to Auphonic, a podcast-related service.
• Driver: Great Phish/headphones cross-reference, but nobody would ever get it, and it has a very crowded meaning.
• Audiosyncrasy or Audiosyncratic: Long, hard to spell.
• Antiradio: Not quite the right idea, and a bit awkward.
• Upgradio: .com available, but a little too cute and gimmicky.
• Auradio: Awkward.
• Remaster, Mastered, Engineer, Amplify, Amplitude, Amplicast, Decibels, Clearly, Auditory, W: Too far removed from what most people know about audio, and many conflicts.

I didn’t love any of these. Absolutely none. I showed lists to a few friends, and they all agreed: Overcast was better.

None of the other names made me excited to work on the app or announce the name in public. “Here’s my new app, Mediocrity!”

So I decided to take the hard road to get the right name, and arranged with the other trademark’s owner to use Overcast legally.

I love Overcast. It’s great on so many levels, and it’s practical, too: simple, memorable, easy to spell, easy to pronounce, relates to podcasting easily by ending in “-cast”, and not too crowded in commerce or Google despite being an English word.

The owner of @overcast on Twitter wasn’t interested in selling, and I couldn’t get it on Tumblr, Pinterest, or Facebook. So I registered @OvercastFM on Twitter, App.net, Tumblr, and Pinterest, and facebook.com/OvercastFM.² I also took @overcast on App.net just in case, but I’m not going to use it unless I get the matching name everywhere else in the future — consistency between services is more important than having the best available name on just one or two of them.

I couldn’t get the .com — its squatter wants $100,000,000 for it. That’s right, a hundred million dollars. I tried to get him to come down a bit, and he said he’d take $95 million. I offered him $1,000, which quickly ended negotiations.

I decided instead to register the .fm for $70, and I don’t think it will ever really matter that I don’t own the .com.