How to Choose A Name For Your Startup

Naming a product is tough. It's thankless, there's no objective criteria for success, and when you're first starting out, it can seem unproductive. But none of these are legitimate excuses for not spending a tremendous amount of time and energy picking that name. Later on, when you have paying customers, the name that shows up on their credit card statements will be a soothing reminder of your consistent and trustworthy brand. Changing it requires far more effort than most founders imagine, so do it right the first time. Here's a concrete step-by-step guide to finding a great name for your startup's product.

Create a list of possible names.

There are dozens of excellent articles that can get you started with the process of brainstorming possible names. Most of these articles do an excellent job of summarizing the most common guidelines, so I will only briefly mention them here:

• The shorter the name, the better.
• Choose something that can be verbed. "I'm going to Twitter this" works much better than "I'm going to ShortMessagesWithFriends" this.
• Choose a relevant name, if you are starting an invoicing company, bikemanufacturers.com probably isn't appropriate.
• Choose names with greater phonetic clarity. The word "phonetic," for example is terrible because it isn't clear when spoken whether it should be spelled "fonetic," "phonetic," "fonetik," or "phonetik." The proliferation of mis-spelled domains and product names have exacerbated this problem.
• For products that create new markets (AirBnB for instance), it won't be important to have a name with high SEO value like "bestbnb.com." If search discoverability is important, however, consider shelling out cash for a name that will rank for your keywords. You can think of this as money well spent compared to the Adwords, conference attendance, and content marketing you would need to do later to drum up traffic for a less discoverable domain.
• If you are struggling to come up with ideas, I recommend using Impossibility, which has the added benefit of only showing you available, non-parked domains.

Check availability and price.

For my second startup, we generated about 150 possible names to start. My cofounders and I checked their availability using InstantDomainSearch, and weeded out names that both didn't excite us and were unavailable. Since we were creating a product that was unlikely to benefit a great deal from organic SEO, we disqualified quite a few domains that were selling for more than a few thousand dollars. [1]

Gather relevant data.

Next, my founders and I rated each name on a scale of 1-10. Using this data, we created an average score for each name that equally represented our preferences. We sorted the names using our aggregate scores and chose the top 15.

We then create a Google form, and sent the top 15 names to 30 people who were either potential customers, close friends, or both. The form asked recipients to rate the names using the same 1-10 scale.

Using the data from real potential customers and those who were heavily invested in our success, we created a final index of each each name's overall goodness.

Steve Blank says that products rarely survive first contact with customers, and the same is true of names. In our case, we had an internal favorite which was disliked by our friends and potential customers. If we hadn't sought feedback, we would have chosen a terrible name!

Contacting Domain Owners

Domain names can be shockingly expensive [2], but for most product-based companies, it doesn't make sense to spend very much on the domain. Quality products take thousands of hours to build, brand, and market. Invest your time in a new name rather than fighting the baggage left by the domain's previous owner.

After getting feedback about our choices, we disqualified the lowest five options and focused on getting one of the top ten names. Of those, only one was not registered, two were unwilling to sell, two did not return our inquiry email, and the remainder quoted prices ranging from $32,000 to $700. The audience favorite, however, was listed for $788, which we ended up purchasing.

Conclusion

Considering the costs associated with re-branding, it makes monetary sense to invest heavily in choosing the best available name. It took us 20-30 hours to make our decision, and among the tasks associated with getting a new business started, I count those hours as some of the most valuable.

[1] Interestingly, the most expensive domain we discovered had a "suggested retail price" of $80,000.

[2] For kicks, you might enjoy checking out the list of the most expensive domain names ever sold. The current king is $35.6M for insurance.com.

I Want To Unsubscribe, Not "Manage My Preferences"

Spam is a huge problem. But my experience with the Gmail spam filter has been heavenly; it's been years since I've seen spam in my inbox promising to enlarge my manhood with a Rolex.

The big problem today is opt-in email. I have been actively unsubscribing from email lists for months. But newsletters, special updates, coupon offers, and other email marketing still arrive every day in droves. During the last seven days I have received 14 notifications from meetup.com, 6 Google+ friend requests, 3 Facebook event reminders, 2 notifications from job boards, 2 newsletters from services I've long since stopped using, 2 survey requests for services I've recently used, 1 LinkedIn update, 1 travel advertisement, and 1 airline advertisement. That's 32 emails in 7 days. I never consciously opted into any of these emails and have tried to unsubscribe myself as best I can.

But increasingly, I see emails sent from large, respectable companies [1] that provide me with no unsubscribe link. Instead there is an insidious trend towards "Managing Preferences," which invariably requires a log in, a brief search to find the unsubscribe option, and a form submit. And after all that am I unsubscribed? Apparently not because I keep getting messages. The companies assure me that I'm off XY email list while seemingly putting me on ZQW list simultaneously. Perhaps most irritating of all, I am spending an increasing amount of time browsing and checking email from my phone, and elaborate unsubscribe workflows thwart my ability to quickly opt out.

As the founder of a web startup myself I do not believe there is anything wrong with emailing customers. I don't even mind that I'm being opted into email lists by default; it actually makes a lot of sense. We did an A/B test a while back to see whether visitors to our site wanted to subscribe to five introductory tip emails [2]. Interestingly, we found that just putting the option to get email--we phrased the offer several different ways-- decreased signups, even though 78% chose to receive them, and getting them vs. not getting them made no difference in conversion past the free trial. Users didn't mind getting email, but they did mind being asked. We derive monetary value from sending customers email, and subscribing users by default causes fewer than 1 complaint per 10,000 emails sent. In summary, a company has every incentive to email its customers, and I don't begrudge those attempts. The problem is that these companies aren't respecting my ability to unsubscribe.

Skritter and CodeCombat newsletters go out to a lot of people every month, and folks seem to enjoy it. We easily get 10x the number of positive responses to our newsletter for every request to unsubscribe. I suspect the reason is that we provide a one-click unsubscribe link that respects people's time and privacy. If my company were 20x larger, we would probably want to send more and different email to customers. But complexity doesn't magic away a company's responsibility to allow innocents like me to easily opt out of their email presence. When a company asks me to "Manage my Preferences," they disrespect my time and fracture my trust.

[1] LinkedIn and TripAdvisor spring to mind as companies that have foisted this on me just in the past 7 days. I still can't figure out how to make the Trip Advisor emails to stop, even after wandering around the "My Account" section on my laptop for several minutes.

[2] The tip emails were a series of 5 emails sent to users during their trial periods that introduced them to site features. They were 100% instructional and intended to increase engagement. We didn't put marketing or sales materials in them.

How Netflix Can Ruin Your App's Value Proposition

When you are running a subscription-based web app, cancellations are a part of everyday life. At Skritter, we realized early on that knowing why people cancelled would be of critical importance. We ask everyone who cancels to let us know why, and a surprising 50% of people actually do. We get these missives via emails and I track them to keep a pulse on what we need to improve. And so it was a fairly routine morning a few weeks back, while reading one such cancellation email, that I was struck by what the user had written:

"I have no money these days. Great program, but $10 is a bit too expensive. Would sign up and keep it for 1/2 the price. Netflix costs less than you guys."

Comparing prices between products is nothing new of course, and the big players in any space will always influence prices for the little guys, but this was personal for two reasons. First, I use Netflix all the time and personally love the company and their product. Second, I also happen to run a small startup which charges more per month than the big red giant I so adore. This user's comment was damning because while Skritter helps people a lot, it was hard to argue that Skritter is more fun or better value than renting 20,000 streaming movies.

This got me thinking about web app subscriptions as a whole. For founders, choosing a price for your product is difficult. It's also one of the most important decisions you will make as a business owner. So it's no surprise, faced with such an important decision, that many founders--ourselves included--look to the market for pricing clues.

The market for subscription services is homogenizing and falling. Back when monthly subscriptions were relatively unusual, there was less consensus regarding what an online web application should cost per month. Was it $50? Or was it $2? There was and is no one right answer for all teams. Unlike the market 2 years ago, however, customers seem more certain today how about much web apps should cost. This certainty is being driven by relative giants, the Netflixes and Xbox Lives of the world, who seem to be settling on a base price between $5-10/mo.

Just as people browsing the App Store expect paid apps to be a few dollars [1], so too do customers now expect to pay a certain amount for consumer web applications.

Big companies are providing customers with price anchors which will increasingly impact customer perceptions of value. While individual web apps will always have unique aspects that enable variable pricing, I don't think the day is far off when a young entrepreneur starting a B2C web app will unthinkingly set his price at $8.95/mo because that's what everyone expects.

The trend, however, is worse still. Because large consumer internet brands--like the industrial widget manufacturers of old--can leverage similar mass production economics, the perceived "correct" cost of a web app is likely to decline over time. Netflix already benefits from a virtuous cycle of user adoption, which allows it to reap more profit by lowering prices. There will be some basement price at which Netflix will no longer want to lower their price, but given that it used to cost $14.99/mo to get worse service than I currently get for $7.95/mo, I suspect that price is lower still. [2]

For those of us in the far remote niches of the internet, I believe that companies like Netflix have an increasing ability to ruin the perceived value add of B2C products through increasingly lower prices. And here I thought the selection was the worst part of Netflix streaming.

[1] $4.03 for iPhones, and $4.37 for iPads, according to marketing firm Distimo.

[2] And perhaps more importantly, the predictability of revenue streams.

Why You Should Refuse to Build a Company on Content

As web business models go, content is well understood: you produce something of value and then monetize through ads, lead generation, or just charging for what you produce. I refuse to start a new business based on selling content and so should you. Here's why:

It Doesn't Pay

The web has produced an extreme abundance of content. It has simultaneously failed to fix micro-transactions. This has resulted in the expected value of any specific information falling to zero. There are isolated niches in which content is still worth money, but they are becoming fewer and father between [1]. As a test of this mindset: would you be reading this right now if I had asked you to pay me even $0.10 for the privilege?

The average piece of content is worth almost nothing. This means that most people in the US can't make a living wage producing content. If you are a good developer, for instance, your time is worth many times more producing code than it is producing content of almost any type.

Producing Content is Unpleasant Work

Some people have realized that content has become too expensive to have people keep producing it. These new content companies (like Demand Media) are highly profitable while traditional content producers (like newspapers) wither and die. Algorithms will be increasingly important in content creation, and they do it just well enough to invite a click and then frustrate you into (hopefully) clicking an ad. Sites like About.com and Mahalo flood search results with just-good-enough information at scale and it's hard to beat companies that wield hundred of millions of links.

With that as your competition, you are forced to create bad/mediocre content as quickly as possible. Producing content is therefore a race to the bottom in which you must compete with the lowest paid global workers to produce bad content as quickly as possible. I don't want to make anything that sucks, much less in large quantities.

There Aren't Any Interesting Problems

You could argue that monetizing content in a sustainable way is an interesting problem, but I would beg to differ. Creating ever-more complex link farms at scale isn't my idea of doing great work. And past that problem, producing content is essentially the same process as it was 500 years ago. I do not mean to imply that creating good content is easy, but the problem is well understood, labor intensive, and has reached a level of development where success is defined more by cutting input costs than by creating better outputs.

Piracy Exists

But just for the sake of argument, let's ignore everything above. If you have a real itch to write the next revolutionary book of jQuery tutorials, there's the issue of piracy. Despite misguided legislation attempting to curb the behavior, piracy is easier today than it was when I downloaded my first MP3 on Napster in 2001. If it's easy to take from you and all you have is takeable, you are in a position of extreme vulnerability.

Again, there are content businesses that make money, but you'll notice such businesses are almost always established B2B companies operating in specialized markets where the liability of piracy is higher than the cost of acquiring material.

This Situation Is Deplorable

I say all of this with the greatest sadness. If people can't make ends meet producing good content, the world is a poorer place. I won't really miss another review of the iPad 9, but I will miss proper journalism. I just finished reading the book 1491. It was both enthralling and breathtaking in the scope of research that went into it. But reading it was a guilty pleasure because I knew the author had to take a huge gamble to write the book, and his odds of making money on his investment were poor. If societies lose people that make it their business to seek truth and produce content, those societies become worse. Watergate was only exposed because 2 Washington Post journalists spent more than three years researching and seeking truth full time. I want to live in a world where people like that can feed their children.

At the same time, I realize I'm not prepared to devote 10 years fighting this issue, and so I refuse to start a company based upon content, and I think if you realistically evaluate the costs, you will too.

[1] I can imagine a number of niche B2B content business models in which you charge for access to highly specialized technical information that changes a great deal. Perversely, one such content business model is law, which doesn't produce any economic value, law merely re-allocating resources between parties.

It's Insanely Hard to Make a Kick-Ass Mobile App

It would be hard to find a self-respecting geek and technologist who disagrees with the phrase "the future is mobile." All the coolest new gadgets are tablets and smartphones and all the biggest plays in content are on those devices. The market dominance of the biggest tech companies depends on how you use that device in your pocket or backpack.

So we get it. Mobile is hot. Mobile is irreplaceable. And most importantly, mobile is the future. But this mobile future takes software for granted.

At both Skritter and CodeCombat, we learned that because we built mobile versions of our apps for iOS. We found that there are so many apps, they have been devalued to the point of monetary irrelevance. That's sad because a good app is a piece of art. The user flows, the interface, the streamlined backend, all the pieces of a finely-tuned app take so much time and energy to perfect that I wanted to write a post to call attention to the level of software perfection that most people have acclimated to without even knowing it. Here are three reasons why it's insanely hard to make a kick-ass Mobile app:

System Constraints

You could say that Objective C is the problem, or put another way, the lack of >insert language< or >insert framework<. But the reason why developers are shackled to Objective C is to make sure processes finish in human time, and this is fundamentally a performance bottleneck in mobile hardware. Swift is a great step forward, but it's immature and for complex backend work, Objective C is still necessary. 

Skritter's iPhone app is great, but at core it is just an app to learn Chinese characters. Skritter doesn't pilot your car or allow you to edit movies or do any other mind blowingly complex task. But when it first launched, it wouldn't run on all but the n-1 generation of devices. When we tried to launch CodeCombat's tablet app, on the iPad 2 Air could run it at decent speeds. Why? Because older devices have limited memory, CPU cycles, and bandwidth, newer versions of iOS brick older devices, and news features are only available to developers on newer versions of iOS.

For a generation of coders accustomed to limitless managed memory, high-level programming abstractions, and thousands of deeply functional opensource libraries, mobile is a step back to the Byzantine world of Commodore 64s.

If you have built an app that doesn't choke on graphics and feels responsive, you have accomplished an incredible challenge and I tip my hat to you.

No Features

User-software interaction paradigms are changing and simplifying. Photoshop's submenus, window management, and setting screens afford it a level of feature depth I don't believe can be achieved in a mobile environment no matter how sophisticated and intuitive UI conventions become.

Put another way, there is a terminal threshold of feature depth to an app and this limits the scope and usefulness of any one app. That's not an intractable problem and the solution that has been embraced to date is app fragmentation. There are separate Skritter Chinese and Japanese apps for this exact reason. But consider the logical extreme of this design trend: if you were to make a fully-featured Photoshop app work on a mobile device, you would end up with several hundred micro-apps to do one thing very simply. Just download Instagram to see what I mean.

So, if you are attempting to make a kick-ass mobile app, you must make a lot of decisions that ultimately come down to "how little will my customers allow me to integrate into this thing?" Err on the side of simplicity and you might end up with a fart app. Go the other direction and you have a pile of unusable menus and sliders.

Extreme Polish

The app market is cruel; even moreso for the need to do a Hollywood launch. Because nobody has solved the discoverability problem in the app store, you need to launch big and magically figure out exactly what users want ahead of time. That last point is especially troublesome for people used to iteratively designing for the web. The road to app store success is littered with the corpses of apps that launched big but hadn't fine-tuned their interfaces, didn't have time to include that key feature users wanted, or just failed to make the app novel in some primal way.

Even the basic business sense of not overbuilding is turned on its head for mobile development. If you somehow manage to land that sweet TechCrunch article or New York Times acknowledgment, the app has to be perfect not just from an implementation point of view, but from a feature and context perspective as well. A perfectly implemented, compelling, novel app isn't enough; you have to know that your customers will agree about your choices.

There's always another app for whatever you are doing, and that makes customers more picky. The pressure to get it right the first time can be crushing.

So Get Insane and Start Building

I write all this not to discourage, but to uplift all those developers struggling with their mobile projects. It's tough to make something good, let alone make something good that also happens to make enough money to warrant the effort. For those out there building apps of consequence, I want this to read as a note of enouragement: stick to it and overcome the difficulties I've written about above. The mobile future is depending on you.