Startup lessons: 5 mistakes I made when I chose my brand name

Choosing “Opsitive” as the brand name for my teaching and mentoring business was a mistake. I know that now, and in this article, I’ll explain what made me realize that there’s much more to branding than just being clever. I’ll outline the tests that helped me identify the weaknesses of my current brand and verify that my new choice, “Monospace Mentor”, is going to be much stronger.

A few weeks ago, I discovered “Creator Science“, a podcast for content creators I can already highly recommend. One of the latest episodes peaked my interest in particular: “How to invent a GREAT brand name.“. For years, I’ve been dissatisfied with my hosting company’s branding, so I was eager to learn more about this topic. And learn I did!

On the podcast, branding expert Alexandra Watkins outlined two acronyms she invented to gauge the quality of a brand name; one checks the attributes to aim at, the other points out pitfalls to avoid. These acronyms are “SMILE” and “SCRATCH”, and you can find their detailed explanations over on Alexandra’s website, “Eat my words“.

Failing the SCRATCH test

Applying these checks to our hosting product confirmed my gut feeling — its name bombed spectacularly. We’ll address this issue in the marketing strategy development process that we’ve just launched recently. But then I did the same test with “Opsitive”, and it dropped on me that it was weak sauce, too!

First of all, the term “Opsitive”, while being a play on the words “Ops” and “Positive”, does look like a typo and thus fails the first “S” in the SCRATCH test, “Spelling challenged”. The fact that I kept getting emails meant for an online shop for women’s healthcare should have alerted me early on.

Its wordplay character also makes the name suffer from the “curse of knowledge”, symbolized by the second “C” in SCRATCH. If you’re not familiar with the fact that “Ops” is short for “IT Operations”, you’ll not get the joke.

Taking a less negative perspective, the name is unfortunately also lacking all of the qualities you should strive for in a brand name according to the SMILE guidelines:

  • It’s not suggestive. It doesn’t say much at all, really.
  • As a made-up play on words, it’s hard to memorize. Was it “Opsitive”, or “Opositive” like the blood type, or maybe just “Opsitiv”?
  • It doesn’t conjure any image because it’s abstract at best and nonsensical at worst.
  • It doesn’t have much legs in that it can be extended to other topics. In fact, its explicit emphasis on “Ops” already puts software development out of scope, an area I definitely want to cover!
  • For the same reasons for which it fails to spur imagination, it’s also not emotional.

There’s another important shortcoming of the old name. It doesn’t put me in the centre, even though that’s the core of my business model: It’s not about the topics I teach, it’s about how I teach them, about my unique way to guide my mentees to their success.

So I needed a new name.

Finding a new name

Coming up with a new name was hard. At first, it seemed that all the good names were already taken. My main problem was finding a name that could accommodate both sides of DevOps, operations and development, but wasn’t at the same time terribly generic. I used several thesaurus websites to research variations on the themes of teaching and mentorship. After many experiments and letting ideas germinate in my brain for days, inspiration finally hit me. There is one thing that unites all system administrators and software developers: they use terminal emulators, text editors and IDEs. And in those, they use monospace fonts. Nerds love their fonts. There are dozens of websites showcasing the huge spectrum of programming fonts, and some people like me even pay good money for a neat commercial one.

And since I just can’t shake my silliness completely, I went for an alliteration as my new brand name. From here on out, I’ll be the “Monospace Mentor”, and my web presence is now at!

Let’s do the SMILE check again.

  • “Monospace Mentor” is suggestive of personal teaching, and it conjures the image of a programmer’s computer screen.
  • It is easy to memorize, helped by the alliteration.
  • It does have legs for expansion in the area of DevOps education.
  • Is it emotional? I’m not sure, but it’s definitely whimsical!

Did I eliminate the problems of the old name?

  • It doesn’t look like a typo.
  • It’s not confusingly similar to the brand of anyone in the teaching space I know of.
  • It doesn’t restrict later expansion.
  • It’s not annoying.
  • It’s not too tame or bland.
  • No curse of knowledge issue.
  • And it’s easy and unambiguous to pronounce.

Much better!

Lots of work ahead

I’ll admit that I’m a bit self-conscious about making this kind of a sharp turn. Curiously, we don’t have these inhibitions when we’re coding. Hey, naming and cache invalidation, amirite? 😄 And after all, learning in public is at the core of what I do.

Since I never had any marketing training, I’m grateful that people like Alexandra Watkins share their expertise so others like me can learn from it. The SMILE and SCRATCH tests were tremendously helpful in finding a name that doesn’t make me anxious it’ll lose me potential business simply for the reason that it doesn’t really work as a brand.

Now I’ve got my work cut out for myself. I have to create new brand assets and update the many places where my teaching business is already present.

I’m happy with the new name. Are you, too? Please let me know what you think on my new Mastodon account or on the Opsitive — wait, no — Monospace Mentor Discord!

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