How do you like the name I chose for this Substack: Failing Forward? Pretty great, right?
It sounds strong. It conveys the mission of this periodical. And somehow, it feels titular—granting authority and professionalism to something nascent. I hope you dig the name as much as I do.
But here’s the problem: it’s also terrible and will likely give me a ton of trouble in the coming months and years.
Don’t believe me? Here is why.
Naming Workstream
There are many ways to brainstorm names for a new company, product, or content project. But what’s fraught is what happens when you hear the name that clicks.
Here is our story: between leaving my old job and formally starting Workstream with Chris, I had the pleasure of hanging with some of my oldest and closest buddies in Bear Valley, California. Four of us decamped for a weekend to my friend’s cabin for an idyllic getaway.
I was showing everyone some initial product wireframes and concepts, explaining how our proposed collaboration solution would “streamline a team’s analytical workstreams.” To which my buddy responded:
“So you’re naming the company Workstream, right? Kinda seems like a no-brainer.”
No matter how much we brainstormed alternatives, that name just stuck. And I think that’s because:
Great names sound great
Your founder journey to this moment was likely different, but most end with a name you simply cannot unhear.
You can’t forget it because it sounds perfect to you. I mean exactly that: the sound.
You want your name to sound great. You want to feel good using it and proud when telling your loved ones and friends. You rehearse introducing yourself: “Hi, I’m Nick Freund, the Founder of Workstream.”
Impressive! You hear your team using it: “This is Scott calling from Workstream, do you have five minutes to chat?”
Damn, that just imbues authority in a 22-year-old sales rep. Workstream just sounds perfect—it could already be a multi-billion-dollar business!
Better names describe the product & its benefits
If great names sound great, better names go further: they communicate to the market what you do.
At one point, I met an experienced brand consultant from Facebook who had started his career as a Don Draper-like ad man. He taught me there are two main subtypes of these “better names”:
Literal names describe the exact thing your product or service provides. Both Workstream and Failing Forward are literal names. Workstream streamlined the work of data and analytics teams. And to boot, “workstream” is a buzzword douchey business people like me use to refer to a unique project or work area.
Similarly, Failing Forward describes the value of this newsletter to my audience and me: it pays forward my learnings to other founders and cathartically helps me move forward from failure.
Aspirational names communicate the “promised land” state your customer aspires to and hopes you can deliver.
The legendary venture capital firm Sequoia is a great example. When they invest, your company becomes enduring and mighty, like the great tree of Northern California. Or take the business intelligence company Tableau, a name implying you can now see the whole scene.
When choosing one name from the many possibilities, ensuring your name both sounds great and is descriptive is an attractive and seemingly important bar.
The best names are impossible to find
Unfortunately, much of this is a distraction in the context of creating the best names. That’s because the best names will sound good and be descriptive—but more importantly, they will be unique and defensible.
Selecting a unique and defensible name is the most important criterion. And to every founder’s eternal frustration, it is nearly impossible to meet all three criteria simultaneously.
Why?
Because you and your co-founders aren’t the first people to do an Ideo-inspired design thinking exercise. Starting new ventures is as American as apple pie and BBQs on Independence Day. There are over two million corporate entities registered in Delaware alone.
This means all the good names are almost certainly already taken. Much like the settlement of the American West, the frontier has closed, and there are no longer any “uninhabited” parcels of land available for you to settle and defend.
So what defines a unique and defensible name?
There is no one else doing business with your name. Ideally, no corporate entity, ever, in the history of business. But at a minimum, make sure there are no notable entities in your market using it. Define “notable” and “your market” as broadly as possible. Reasonably this means “no household name” or “well known startup” in “your market sector / tech.”
You can buy and protect the domain and related assets. The internet has been around for awhile, and in case you didn't know people are squatting on almost every good .com. Ideally the .com (or another premier top level domain like .io) is available for a reasonable price. You also need to ensure that you can also buy as many related TLDs as possible (i.e, getworkstream.com, workstream.ai, etc), and reserve desirable social media handles to prevent future brand confusion.
Finding a good sounding and descriptive name that also hits these criteria is almost impossible. So what do many companies end up doing?
They just make up a name, or choose something obscure and foreign. Names like these, which do not live in any dictionary, are less likely to have been previously trampled upon.
Skeptical this works? Look at NVIDIA. Today, it’s a marquee company despite its odd spelling and prononciation. Here is the story, according to chatgpt:
The name NVIDIA comes from the Latin word "invidia", meaning "envy," symbolizing the color green, their signature hue. The prefix "NV" originally stood for "next version," reflecting innovation. The name embodies their focus on cutting-edge technology and being forward-thinking.
Was Workstream the best choice?
So how did we do across these criteria at Workstream? Unfortunately, our choice led to market confusion and created headwinds for brand building and customer acquisition.
While I was able to cheaply buy Workstream.io from a squatter (for $15K), Applied Materials owned—and continues to own—Workstream.com. But over time the company operating at Workstream.us caused us far greater problems.
When getting started, I was aware of another Seed stage startup called Workstream offering a solution to hire and retain hourly employees. I justified our naming decision by telling myself we were selling into corporate data teams, not fast food hiring managers.
However, as time unfolded the decision turned out to be both bad and unlucky.
The other Workstream quickly achieved product-market fit and went on to raise a Series A. Today they have raised over $100M and are well known in tech circles. This resulted in tactical confusion with VCs; there were times I would take an investor meeting where they were presumably excited to to speak with the founder of the other company 🤦.
More importantly, the name caused confusion in the market. We often got installs from marquee names like Chic-Fil-A, or Burger King. My team would get excited, only to then see installing users that were hiring managers, or new employees looking for the other product. Search ranking for our own name was challenging.
Our choice of name caused tactical confusion, bad installs, distorted metrics, and market distraction. And ultimately, it led us to change our doing-business name to Workstream.io to ensure that people knew who we were and could find us.
How are we doing with Failing Forward?
Let us review:
The name sounds great, so it is a great name. And the name describes the product (or content), so that means it is even better. But unfortunately, it fails the unique and defensible test; so it is not the best name I could find.
Try visiting failingforward.com, or googling “Failing Forward.” You will be directed to the leadership consulting practice of Jonathan Maxwell, whose book Failing Forward is widely associated with the term. When a name feels too perfect, it probably is.
So what is a founder to do? Should I change the name to something more obscure and defensible?
Probably. But do you know what?
I’m too emotionally attached already. I like the name too much. It feels right. And it hasn’t caused me problems — yet.
F&ck it. Some lessons die hard.
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