Startup PR Tip: To Get Press, Don't Pitch Your Product

Posted by Dharmesh Shah on Thu, May 16, 2013

Entrepreneurs that are looking to get attention from bloggers and journalists will often pitch their businesses themselves or though a PR agency.

It's sad that most of those pitches fall flat and are likely to be completely ignored. A waste of time and money for everyone.

For example, here’s a pitch from a PR professional. I’ve changed it slightly to avoid embarrassing anyone:

“I’m working with a wonderful new business… The owners grew up together and decided to go into business… it’s a story I’m sure your readers will care a lot about!”

Uh, no. It's unlikely that people are going to care about this story.

Don’t get me wrong. I’m sure the entrepreneurs are great people, but many entrepreneurs can tell a tale of struggle and euphoria and heartbreak and someday, against all odds, turning their dreams into reality and making their business a success. While occasionally readers might be inspired or motivated, for the most part we’re just not that interested in other people’s stories. Unless those stories are particularly remarkable we're more apt to just keep living our own dreams and writing our own stories. So, the things we're interested in is not other people's stories, but information that helps us write our own.

So what should you do if you’re trying to spread the word about new products and services, landing new customers, bringing investors onboard… all the stuff you hire PR agencies to do for you or, more likely, try to do on your own?

If you’re looking for press, forget the formulaic, cookbook approach to crafting a winning media pitch. That approach may result in coverage in a few outlets… but not the ones you really want.

Quick rule of thumb: Any media outlet that will do a story based on a crappy pitch is a media outlet that will get you crappy exposure.

Let’s pretend you’re thinking about pitching me an article idea for OnStartups.com (which has a modestly sized, but awesome audience).  You can apply the following to any media outlet or blog, though.

Here’s what to do and not to do:

Don’t tell me your story is unique.

No offense, but it really isn’t. There are thousands of Ramen noodle stories. There are thousands of 3 am “Eureka!” stories. There are thousands of maxed-out credit cards, relatives won’t return your calls, last-minute financing savior stories.

Your story is deservedly fascinating to you because you lived it (just as my story is fascinating to me), but to the average reader your story sounds a lot like every other entrepreneur’s story. Claiming your story is unique creates an expectation that, if not met, negatively impacts the rest of your pitch.

And if your story truly is unique, I’ll know. You won’t have to tell me.

Don’t tell me how much a little publicity will help you.

Never waste time by explaining how this could be a win-win relationship or, worse, by claiming you want to share your wisdom because you simply want to help others.

I know you want publicity, and I know why. I get it. I've been there. We’re cool.

Know what I’ve done recently.

It’s easy to think, “Hey, he recently wrote about choosing a co-founder, so I should pitch a story about how I help people find co-founders”

Um, probably not. If just wrote about co-founders. I’m probably good for a little bit on that topic. Never assume one article indicates an abiding fascination with a particular topic.

But do feel free to pitch if you aren’t a member of the choir I just preached to. Different points of view catch my attention; same thing, different day does not.

Know my interests.

You certainly don’t need to know I enjoy late-night walks on the beach. (Hey, who doesn’t?) But skim a few posts and you’ll know I have a soft spot for company culture, startup funding and startup marketing

So if you really want to get my attention, don’t use the tried-but-in-no-way-true “mention you really enjoyed something recent the writer wrote” approach.

Instead put your effort into finding an angle that may appeal to my interests. If you can’t be bothered to do that you’ll never get the publicity you want.

Forget a profile piece.

Straight profile pieces that tell the story of a business are boring. (At least I think so, which is why I don't post those)

The best articles let readers learn from your experience, your mistakes, and your knowledge. Always focus on benefiting readers: When you do, your company gets to bask in the reflected PR glow.

So,readers don’t want to know what you do; they want to know what you know. If you started a company, share five things you learned about landing financing. If you developed a product, share four mistakes you made early on. If you entered a new market, share three strategies you used to steal market share from competitors.

And while you may think the “5 steps to” or “4 ways to” approach is overdone, keep in mind readers love them… and even if I decide not to frame the story that way, developing mental bullet points ahead of time is a great way to organize your information (which helps me) and ensure you have great talking points (which definitely helps you.)

Realize that the more you feel you need to say… the less you really have to say.

Some people think bloggers are lazy and look for stories that write themselves. I can’t argue with the lazy part, but I really don’t want to read a 1,000-word pitch with a comprehensive overview of the topic and a list of semi-relevant statistics. The best products can be described in a few sentences, and so can the best pitches:

So now let’s get specific. Pretend you’re crafting your pitch:

Remember: forget what you want.

Many people think, “Wow, it would be awesome if OnStartups.com ran a story about our new product—think of the exposure! So many VCs would read it! We're looking for funding!"

Maybe so, but unless you focus on how readers can benefit from the story (learning about your new product isn’t a benefit to readers), that’s not going to happen.

Then, think about what I want.

I want to inform and occasionally – hopefully – entertain readers; the more you can help me accomplish that goal, the more interested I am in what you have to say.

Then craft your pitch with publicity as a secondary goal.

In the example above, the PR pro didn’t offer readers anything. His only focus was on getting publicity to benefit his clients.

Flip it around and focus solely on how you can benefit readers. When you do, your company will benefit by extension.

For example, if you want to spread the word about:

· New products or services: Share four lessons learned during the product development process; describe three ways you listened to customers and determined how to better meet their needs; explain the steps involved in manufacturing products overseas, especially including what you did wrong.

· Landing a major customer: Describe how you changed your sales process to allow you to compete with heavy hitters in your industry; share three stories about major sales that got away and what you learned from failing to reel them in; detail the steps you took to quickly ramp up capacity while ensuring current customers needs were still met.

· Bringing in key investors: Explain how you helped investors embrace your vision for the company; describe four key provisions that create the foundation for a solid partnership agreement; share the stories of three pitches to VCs that went horribly wrong and how those experiences helped you shape a winning pitch.

Sound like a lot of work? It is, but it’s worth it. When you offer to help people solve problems and learn from your mistakes, bloggers and writers will be a lot more interested.

More importantly, readers will be more interested in the news you want to share because first you helped them—and that gives them a great reason to be interested in your business.

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Getting Crunched, Mashed Or Beaten Is Not A Launch Strategy

Posted by Dharmesh Shah on Tue, Mar 19, 2013

This is a guest post by Alex Turnbull.  Alex is a serial SaaS entrepreneur and the CEO of Groove, a customer support software platform for startups and small businesses.  Alex was previously a co-founder of Bantam Live, acquired by Constant Contact in 2011.

It’s here!

After many, many months of long hours, take-out and cheap beer, launch day is finally here.

Your eyes are sore from not having looked up from your computer in what seems like ages, and every part of your body is screaming at you to get some sleep, but you’re too hopped up on coffee and adrenaline to listen.

This is it. This is what we’ve been working our asses off for. To reveal ourselves to the world in all of our disruptive glory. Silicon Valley will kneel before us.

It’s like the slow, painstaking ride to the top of the first drop on a roller coaster; you just know it’s going to be absolutely exhilarating, but first you have to trudge all the way to the peak of a steep climb. Tired of waiting but itching with anticipation, you finally reach the top, and then…

Nothing.

Not a damn thing.

Scoble isn’t billing you as the next Instagram. You’re not showing up on Techmeme with a dozen stories about your launch. And the traffic. That sweet, traction-building traffic that you’ve been awaiting — the traffic that was going to prove that people were interested. That they wanted you. It never comes.

Who’s to blame for all of this?

That’s easy. TechCrunch. Those bastards.

If only they had read your press release, they would’ve seen that your story needs to be told! Your product is unique and compelling, dammit! How could they do this to you? How could they crush your dreams of a successful launch by totally ignoring your pitch?

Of course, you’re a startup. Bouncing back is in your DNA, and you get right back to work. But the experience is discouraging, and I've seen this story play out way too many times with friends and founders I’ve spoken to. And know that I’m speaking from experience: I've absolutely made this mistake before, too.

Here’s the reality: pitching TechCrunch is not a launch strategy.

It seems obvious, but it takes more than one hand for me to count the number of times a founder has told me that they expect their launch traction to come from getting picked up by TC (or Mashable, or VentureBeat, or AllThingsD, or any one of a number of similar outlets).

What every single hopeful founder with a similar plan doesn't realize (or doesn't take seriously enough) is that there are hundreds of other founders doing the exact same thing, and hitting the exact same “Tips” email account with their pitches.

Don’t get me wrong, here. Press is good, startup bloggers tell important stories and press outreach should be a part of your launch strategy. But it’s not enough.

So what’s a startup to do?

Let’s get this out of the way: a lot of folks will tell you that the first thing you should be focused on is building a great product that improves people’s lives. And they’re absolutely right. Nobody wants to hear about a crappy product, and more importantly, nobody wants to share your crappy product with their friends.

But let’s assume you've got something amazing. How do you get the world to notice?

First of all, shift your thinking. F*ck the world. It’s “tell everyone” approaches like this that lead to launch strategies like the one above. You don’t need the world to notice. You need highly qualified potential users to notice, and there’s a huge difference.

At Groove, we spent twelve months in beta, rigorously testing and iterating our HelpDesk and LiveChat apps to get them ready to launch.

But here’s something else we did, that you can do, too: we spent that time rabidly collecting email addresses of potential users. We asked our most engaged beta users to share our website (and lead collection portal) with their networks, we blogged about topics that were interesting to a customer support audience, and we wrote content for external outlets that brought value to readers, and loads of inbound leads to us.

When launch day came, we were ready: press release, pitch list, product video, blog post, email blast, the works. Here’s how it played out:

We pitched our press list.

The good people at TheNextWeb covered our beta launch a year ago, so they were interested in how far we've come. They wrote a great piece about us, and the inbound traffic got us about a few hundred signups. It was awesome.

Like everyone else, we also wanted to get Crunched. Or Mashed. Or Beaten.

Ouch.

But what hurt even more, is that like almost everyone else, we didn't get covered by any of them.

I have no doubt that a barrage of press coverage would've gotten us even more new users, but we knew that the odds were against us, so we planned for it.

Taking our carefully nurtured list of email addresses, we sent out an announcement about our launch, with clear calls to action to sign up and get in on the fun.

The result?

Double the signups, at nearly four times the conversion rate of visitors coming from the TNW piece.

Note that we didn't email this list cold: we had spent months giving away content for free, nurturing the relationships, before asking for anything. I can’t stress the importance of this enough.

We also sent an email out to beta users, announcing the launch and asking them to share Groove with friends who might find it useful. That email netted us another 120 users, at a conversion rate nearly double that of the TNW traffic.

It shouldn't be surprising that the most valuable traffic we got came from qualified leads we had already nurtured. But the problem is that most startups won’t make the effort to build that audience until after launch. I know, because as I've mentioned, I've made that mistake, too.

Look, I know that as an early-stage team, the chances that you have a full-time content person are nonexistent. But the chances that someone on your team has a modicum of writing chops are pretty damn good, and getting them to invest a couple of hours a week in this exercise can pay off in spades when the time comes.

At a loss for what to write about? Every startup should know how their customers think, and knowing what’s interesting to them is a major part of that, and it’s absolutely okay to ask them what they’d like to read about from you. Email them, survey them, chat with them. They'll appreciate it. Trust me.

In the meantime, here are a few ideas:

• Write about your startup experiences - be honest and transparent (check out Balsamiq-founder Peldi’s blog, where he captures this masterfully)
• Stir the pot. Share your thoughts on controversial topics with your audience.
• Offer best practices for your space.
• You’re probably an expert in whatever it is that you do — share your knowledge.
• Everyone likes a success story. Or one about failure. Tell yours.
• Show off case studies and interviews with your customers. This clues your audience in to what others using your product are doing well, and makes the featured customers feel good about themselves (and their relationship with your company).

Summary: Getting Crunched is not a launch strategy, and you shouldn't bet on it to make your startup blow up. Reach out to the press, but diversify your launch plan to reach qualified leads that you've already been nurturing. Invest in content. Profit. The end.

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Our PR Stinks: Here's What Your Startup Can Learn From It

Posted by Dharmesh Shah on Thu, Dec 20, 2012

We were convinced from the very beginning that strong PR would be the answer to our market entry prayers. This is the story of how our reality turned into something of the opposite effect.

The Familiar Doubt

Many friends, fellow founders and business professionals told us along the way that creating a B2B interactive business platform would be a difficult project. (Hey, we knew that.)

People later told us that the most difficult aspect would be market entry. (Again, no surprise there.) The consensus among those critical of our venture was consistent, and usually along the lines of, “Don’t you want to do something more glamorous than a B2B platform? Maybe something B2C?”

(Actually, we believe our concept is glamorous and quite frankly, exactly what we believe the B2B market calls for.)

Any way you thought about it, the task at hand was going to be tough. The start was the most challenging, with an idea and an empty platform. But we were not the first facing this issue; surely there would be ways to maneuver our way into our key markets?

We knew some companies who successfully bought profiles or created fake ones, but decided that if we really believed in our concept, we would need real people behind genuine profiles and articles. And that we would need press coverage.

How did we solve the first problem of filling the platform?

We first talked face-to-face with various professionals we knew to get them interested and excited enough to participate on the platform, even though the it was new. It was hard, but we did it. Twice. Once on the German site, and again, when we went international with the English platform.

We were ready to move onto the next stage.

 Growth.

How do you go about growing something like a self-publishing platform for B2B professionals? How do you create public awareness? Would press coverage do the trick? High-profile technology publications, with all of their reach, would be a nice start…wouldn’t they?

Indeed, we tried various forms of press outreach. After making a bad choice with a PR company for the German market, we chose the PR Company for our international venture with care. After months of consideration, research and negotiation, we made a deal with high hopes that we would see the benefits of this lucrative investment. While it would be wrong to say we gained nothing from this several month contract, it would be an exaggeration to say that it was worth the time, energy and money to do it again.

Maybe we chose the wrong firm or worked with people not experienced enough with an international, startup market. Regardless of the reason, we only barely inched along.

Eventually, we were forced to go out on our own to create brand awareness and ignite public interest.

The Big Guys

This time, we aimed for the big guys and landed one on our own. Coverage on GigaOM inspired positive feedback surrounding our concept and functionality. But as it turns out, getting highly coveted coverage is not enough. What happens is this: you get a spike of traffic, a couple of hundred or even thousands of visits for a day, but only a fraction of the traffic persists.

PR can work if you manage to stay continually on the radar of journalists. We did not succeed in getting enough “coverable” news out over and over again and thus faced the problem of limited exposure.

After personal and fired efforts, what did we learn?

Our PR still stank.

Without a celebrity investor or seven-figure financial round each month, we were forced to do what startups do best: build something from nothing, by using what we had.

Looking back, this hardship turned out to be a great thing for our business development. Without being able to rely on press coverage, we were forced to learn and engage in a marketing strategy - to find other ways to generate traffic and convert our target audience.

Essentially, our lukewarm PR made us better entrepreneurs.

How, exactly, did we manage to grow?

As a social publishing and content marketing platform we decided to do exactly what we had been advising our target group to do: run a content-based, social media campaign. The steps were as follows:

1. Research our target group: This involved getting to know the habits and motivations of our target group within each social media and online channel. It also required us to understand the conversations that were talking place about issues relevant to our service and knowing what our industry influencers were saying. Specific to our success, were analyzing Twitter and LinkedIn.

2. Connect with influencers: Connecting with influencers allowed us to learn the language of our industry and lay the foundation for future interaction. When we later began to produce content, we could guest post on these influencers’ blogs/websites and involve them in a series of interviews. In both cases, we found ways to expose ourselves to their followers.

3. Create content of utility: We knew that content had to be informative and engaging. Yet, the content that really made a difference for us was that which offered our platform and social media communities a sense of utility. If our content could be used to better understand the industry or tackle a common problem, it was more likely to be shared and discussed.

4. Publish content: This was when we had the opportunity to do what we had been advising our target group to do the whole time: publish on exploreB2B. Not only did we publish articles on our platform, we guest posted on active and relevant sites and blogs.

5. Distribute content: Publishing content was only one step of the battle. Distributing the totality of our content through our social communities served to create leads to our platform and, in turn, grow these subsidiary networks.

6. Continue to grow online communities: This was one of the largest factors in our spike in traffic and referrals. Once we grew our Twitter accounts and initiated daily interaction in LinkedIn groups, whole communities of like-minded people were exposed to – and became familiar with – our brand name. Growing our Twitter account from miniscule numbers to five-figure followers became a powerful increase in our visibility. Even though we are B2B, this kind of “social branding” played a large role in our growth.

Through a campaign of trial and error, we learned that social media and content marketing success is not immediate – and that it is not the result of one magical post. The persistence of our actions and the combination of the different measures resulted in a social media following, trust in our content, visibility, and stable platform growth.

What were our end results with PR?

1. A spike in traffic during April 2012.

Yes, that’s it. And it was smaller than our current (steady) growth rates.

What were our end results with content marketing?

1. Brand awareness.

2. Connection to key, industry influencers.

3. Large and active social media followings on more than one network.

4. Trust in our useful and engaging content.

5. An increase in weekly visits by a factor of ten.

6. An increase in registrations by a factor of ten.

In the few months we have spent content marketing, we have achieved something that gives much more value to our company than traffic spikes created by media coverage. We have an ongoing dialogue with our users, a network base that constantly returns to our site, and consistently grow our traffic.

Results from our content marketing campaign far outweigh any benefits we gained from being covered in the press.

We have survived by making ourselves the leaders of our own movement, utilizing the platform we created, employing the marketing strategy we recommend and connecting to thought leaders in our field.

Weekly traffic of exploreB2B from March 2012 to November 2012

Though our content marketing results were not instant, we were able to use this time to build trust and establish a reputation in “social business.”

With positive user feedback and a steady increase in their own article production, we now sense real stability in our social media and platform interactions.

At this point in time, our PR still sucks.

But, maybe that is just the point. It is due to the fact that our PR was not successful that we attained something that has proven more valuable in the end: steady, self-achieved, and sustainable growth.

The Fate of Your Brand

My advice for startup growth is to not rely on press to determine your market reputation. Instead, formulate a connection to your target group members by telling your own stories and sharing knowledge that defines your industry leadership. This provides a foundation for your own means of security and growth.

Using methods such as social media and content marketing, figure out where you can reach your target group and pursue them in helpful and entertaining ways. It’s not the tech journalists, bloggers and authors covering your competitors who protect and ensure the bottom line of your company.

In the end, it comes down to the people who trust you and find value in your ideas to decide the fate of your brand.

This was a guest post by Susanna Gebauer.  She is one of the founders of the social publishing and content marketing platform, exploreB2B. You can also find Susanna on Twitter.

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Building It Is Not Enough: 5 Practical Tips On User Acquisition

Posted by Dharmesh Shah on Wed, May 02, 2012

The following is a guest post by Brian Balfour, Co-Founder and CMO of Boundless. You can read more of his writing on his blog at BrianBalfour.com.

Stories about the growth of "hot" startups such as Facebook, Instagram, AirBNB, and others have created a belief that if you build the right product, customer acquisition will be easy. Don't be fooled. These stories are the exception, not the rule, and don't tell the entire story of the immense effort it took to grow their customer bases. Finding scalable acquisition channels is a time consuming and strategic effort.

If you build it, they may not come.

You probably have a product roadmap and a development process. But do you have a process and plan to discovering your scalable customer acquisition channels? For software development we have well documented processes such as Agile, Waterfall and Kanban. For finding product market fit we have an increasingly defined process in customer development and the lean startup methodology.

Finding scalable customer acquisition channels is as much of a process as software development or finding product market fit. Here are five mistakes to avoid in finding your initial customer acquisition channels.

1. Do Not Test A Lot Of Channels At Once

This is the ol' throw stuff against the wall and see what sticks strategy. Unfortunately this rarely works. Consider this, with Facebook ads you typically need to change your creative every 24-48 hours across 10 - 20 different segmentation combinations, with 4 - 10 ads per combination. That is in addition to all of the landing page testing you'll need to do for those combinations. It is easily a full time role. Think you will have time to focus on another channel at the same time?

Inbound marketing takes an incredible amount of time for content development. SEO requires testing thousands of page combinations, time to build influential links, and plenty of on-page optimization. My point is, properly testing any single customer acquisition channel is extremely time consuming and requires focus.

It is easy to think that the fastest way to find a channel is to test a lot at once. But with limited resources it is the exact opposite. Let's look at it a different way. If you had very limited engineering resources, would you have them try to build 4 different products at once to find one that works? I hope not. You would end up with 4 partially built products with little information on which one is going to to work.

Instead, you would likely evaluate each product idea, strategically choose one, focus, iterate on it for at least a couple months, and only then decide to keep moving forward or move on. Finding scalable customer acquisition requires a similar amount of strategic decisions, focus, and iteration.

The quickest way to finding your first scalable channel with limited resources is to focus on one at a single time and iterate based on feedback (metrics) just like you would with building product. At Boundless, we have been lucky to have enough resources to test two channels at once. But even with close to $10M in funding, we won't go beyond testing and optimizing two channels for awhile. Don't underestimate what it takes to properly test and optimize a single customer acquisition channel.

2. Diversity Of Channels Is Not Important In The Early Stage

Entire companies are typically built on the back of one or two channels. Look how far Zynga has gotten with basically two channels - Facebook Ads and Viral Mechanics. Only now are they starting to diversify with the launch of their new platform. Facebook itself relied completely on viral growth until they had reached millions of users. Only then did they start optimizing for SEO. AirBNB grew their initial user base almost completely on the back of craigslist.

For reasons discussed in number one, diversity of channels actually increases your risk that you never find a scalable channel at all. Remember this - momentum of growth trumps diversity of channels. Once you find a channel that is working at a small scale, don't be tempted to add another channel to the mix. Instead, focus on optimizing, scaling, and milking your initial channel for all its worth.

Your goal in the early stages is to grow as fast as possible with limited resources. Finding further growth in a channel that is already working is typically easier than finding a completely new acquisition channel. When you start to reach the max potential (where the growth curve starts to flatten), only then should you add another channel to the mix.

3. Paying For Users Is Ok

Magical stories of instant viral growth has formed a negative stigma around paying for users especially in the early days of a product. Entrepreneurs almost feel guilty if they pay for users. This leads to startup pitches that often include a slide that says "we've grown to X# of users with out paying for a single one."

Every, and I mean every, acquisition channel costs money. It is just a question of whether the cost is direct or indirect. Channels such as PPC obviously have a direct cost. However channels such as SEO and Viral are commonly seen as "free" channels. They aren't. To properly optimize SEO and Viral mechanics takes significant engineering and other employees' time. That time is costing you money. The cost is indirect, but you are still paying for users.

Those "free" channels are certainly valuable in the long term. But they often come with short term disadvantages. For example, SEO typically takes months of effort before you gain meaningful traffic. In the early stages, speed of learning is the most valuable thing. Do you really want to wait a few months to learn the same thing you could learn in less time with another channel?

Viral growth deserves its own mention here. It is the treasure that most entrepreneurs are seeking. They want to be the next Pinterest or Instagram. Keep in mind a lot of products aren't suited for viral growth. I think a lot of entrepreneurs overestimate whether or not their product is a fit for pure viral growth. If your business isn't suited for viral growth, that doesn't mean you have a bad business. You just need to find a different customer acquisition strategy.

4. You Only Need 3 Tools To Test Your Customer Acquisition Channels

The "measure everything" mantra has lead to a belief that an array of tools is needed to find a scalable channel. Between analytics, A/B testing, ad platforms, feedback, support and a host of other tools it is easy to get lost. If you wanted to learn to play basketball, would you go out and spend $1000 on the latest gear first? Or would you just grab a ball, find a hoop and start playing? Hopefully you answered the latter.

To test any customer acquisition channel all you typically need is Google Analytics, Excel, and some basic SQL skills. Those three things will take you surprisingly far for any channel before you need anything else. Don't get caught up with the tools, just get testing.

5. Avoid The Button Color A/B Testing Rabbit Hole

The rise in A/B testing and other analytics tools have created fairy tale stories of changing a button color, or moving the CTA from the left to the right and suddenly you have game changing improvements. Once again, these stories are the exception, not the rule. It typically takes 10 A/B tests to find one that produces any improvement at all. And when you do have a positive improvement, it is typically incremental instead of game changing.

Being metrics focused is important. But knowing how to properly influence them is even more critical.

In the early stage you should not be focused on incremental improvements. Your initial CPA for any new channel is likely to be a factor off from your target. That means you need to try and make big improvements to understand the viability of the channel. To see big improvements, focus on messaging, targeting and activation methods. Save your color experiments for when you are ready to optimize and scale a channel. Not when you are testing the viability of a channel.  

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What do you think?  Any additional tips on how to acquire users for early-stage product?

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Startup Branding: A Practical Guide for Entrepreneurs

Posted by Dharmesh Shah on Fri, Jan 20, 2012

The following is a guest post by Mike Troiano. Mike is a former New York ad man turned venture-funded entrepreneur, now a Principal at Boston-based Holland-Mark. You can follow him on Twitter at @miketrap, and connect with him elsewhere through About Me.

1. What does startup branding really mean for an early-stage company? Is it just picking a name and a logo?

"Brand" is one of those words everybody uses and nobody really understands, so I'll start with a definition.

It's important for entrepreneurs to understand that their "Brand" is the collective emotional response to their product or service. A brand is not a logo, and it's certainly not a URL. Those things are the stimulus, while the brand is the response. It's something out there, in the hearts and minds of the people you hope to sell to.

So... Do I think it's important for startups to be thoughtful about the nature of the emotional response that might serve their interests, and try to build a graphic identity designed to elicit that response? Abso-freaking-lutely.

2. Any favorite startup examples that they think are particularly clueful about brand and drawing out the right emotional response?

Sure, a few come time mind right away:

Zipcar a brand we've played a role in since the beginning - isn't about urban lifetstyle, or being green, or collective commerce, really. From day one it's been about Freedom, from both the hassles of car ownership and car rental (Wheels when you want them.) Focus on that emotional value proposition has guided everything from brand identity to vehicle selection at the company, and Zipsters around the world have responded with not just loyalty, but advocacy.

Path 1.0 was a decent execution of an interesting idea, that you could derive more value from a smaller social graph of actual friends than you could from Facebook's comparatively industrial-sized cohort. Problem was, there wasn't anything in the original UI to inspire an emotional response, and the service foundered. While much has been made of the radical turnaround in user experience for v 2.0, for me the result of those improvements is a kind of easy intimacy on the mobile device, something that distinguishes Path from other networks, and is the root of user's newfound enthusiasm for the product.

Instagram is interesting because they got it so right in the product, and so wrong in the messaging. Does anybody really love Instagram because it offers Fast, beautiful photo sharing on the iPhone? Really? I think Instagram helps us notice and share more of what we find beautiful in the world. And I know that promoting it that way would help them grow faster.

3. Speaking of names, how do I pick a great name for my startup? Does it really matter all that much?

I've always thought it matters less than people think.

10% of names are great and that helps a business at the margin, and 10% of names are crap and that hurts a business at the margin. The implication is that 80% of names are not a material driver of brand impact or business success, so sometimes it's just best to get on with it.

For proof of this, there's a great story George Lois once told me, about the first time he heard about a client called "Xerox," in the 60's.

"It sounds like a Chinese laxative," he said. I bet it did to most people, and they did OK.

The point is you can make just about any name mean something to people with great product execution over time. Spend some time getting the tactical fundamentals right - url-friendly, sticky, distinctive, that kind of thing then pick something 3 of your cooler friends think is decent, and move on.

4. What about logos? Can I just hack something together? Use a crowdsourcing service like 99Designs? Or is that a waste of time?

I think logos and the graphical identities of which they are a part matter a lot. They're something the West coast and NY-based guys seem to care about and do way better than Boston-based startups, and that's always bugged me.

Look... in the early going perception is reality for a startup. So is it worth investing a little dough to encourage the perception that you're professionals; that this is a serious and professional undertaking; that you care about design and brand response? I guess there are a few businesses where it isn't. But for the vast majority I'd say it absolutely is, that it's worth investing in a professional identity.

If you're among this vast majority, you want to work toward something smart, not just something pretty. What I mean by that is you want to start by being thoughtful about your brand meaning the emotional response you want your product to elicit as well as any practical ideas or metaphors that will help people understand what you do. Armed with that you should sit down with a reasonably-priced freelance designer to brainstorm some treatments, and keep at it until you hit on something you and others seem to like.

In my experience great design comes from the collaboration between someone with a clear vision for a problem (a thoughtful entrepreneur,) and a professional with the talent and craft to create something great (a real designer.) You just don't get that interaction using the crowdsourcing guys, which is why I think you get what you pay for there.

5. Any tips on where to find a great freelance designer for a startup logo? And, what would you consider reasonably priced?

Try checking the portfolio sites, like Carbonmade. Find someone whose work you admire, then call them to talk about your project. Look for someone with whom you have chemistry, who can bring ideas to the table and not just pictures. And take theiry're advice when they offer it they do this for a living.

Expect to pay $50-75/hour, and to be glad you did.

6. How do I decide what category my startup falls into? Is it better to find an existing category, or blaze the trail of a new one?

The short answer is, it depends, but on balance it's better to pick a category that already exists.

From a marketing communications standpoint, a category is a frame of reference for the buyer. If you think of it that way the value of one becomes clear, as does the time, hassle, and expense of creating your own.

That's not to say that sometimes it doesn't make sense to create a new category, and I've used HubSpot as an example of a company for which it was necessary. For entrepreneurs enamored of that idea, I often follow my HubSpot observation with the question, "So how's your book coming?" That question is usually met by a blank stare, but the truth is that level of commitment to IP is what it's going to take to create a category.

If the opportunity cost of doing that is too much for you, just hold your nose, pick a category, and focus on communicating your distinction within that category in a way that resonates with your target.

7. How much does good branding matter when trying to raise capital? Is smart money really fooled by that kind of this? Will I look foolish for having invested in brandinged in one?

I'll say it again: Perception is reality for an early-stage startup. One can argue  that the world would be a better place if this were not so, if Excel drove more decisions than PowerPoint. But that argument is a waste of time, my friends.

VCs invest in the companies that win over their hearts and their minds, usually in that order. If you're trying to raise money it's important to remember this, and to invest the time and energy you need to court a little loving, and not just a good first look scorecard.

And the same is certainly true for customers, so sooner or later you're going to need to spruce up a bit and look like a brand they want to be a part of. Why not start now?

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Cult of Product: Marketing Isn't Just For Losers Who Pay For Sex

Posted by Dharmesh Shah on Wed, Nov 30, 2011

The following is a guest post by Mike Troiano. Mike is a former New York ad man turned venture-funded entrepreneur, now a Principal at Boston-based Holland-Mark.  You can follow him on Twitter at @miketrap, and connect with him elsewhere through About Me.

Product, product, product. More focus on product was at the center of Brad Feld's comments at last week's Silicon Valley Bank CEO event, in response to a question about what he'd do differently if he had it to do over. More focus on product is at the core of the Lean Startup Revolution we're all getting behind, and in the spine of the Steve Jobs bio we're all reading, and in the frequent posts of the startup bloggers we all pay attention to.

And it's all true. Product is the key, at the very center of building a viable business from nothing. And by implication, marketing is so 15 minutes ago. Marketing is for products unworthy of passionate advocacy, a crutch for nice-to-have startups who invest in sprawling web sites and launch parties like losers with no choice but to pay for sex.

I spend a lot of time fighting this perception, talking about the difference between the kind of strategic marketing that can corrupt your vision with the external reality, marketing communications, which consists largely of the promotional sham-ware of the mid-twentieth century.

But you know what? I'm giving all that up. I'm going to take another approach, one I think will resonate more clearly with the Cult of Product sub-culture which seems to be sucking all of the oxygen out of the shill-o-sphere.

Ready? Here it is: You should focus on the desired response to your product, not just on the product itself.

Why must you focus so intently on your product? Isn't it because you want people to respond to your product in ways that propel your businesses to greatness? Isn't your product, then, a means to an end? Isn't it a stimulus hoping to evoke the right response on the part of the customers who buy it?

In a very real way, I'd argue yes. More than that, I'd argue that the primary dimension of product response that propels businesses to greatness is emotional response.

What do great un-advertised, Billion-dollar brands like Dropbox, Facebook, and even (until recently) Google have in common? We love them. They make us feel respectively Liberated, Connected, and Empowered in ways that enrich our lives. They make us grateful, make us want to share with others. A brand is nothing more than an emotional response out there in the world, but building brands with products instead of print advertising doesn't make them any less important, or any less worthy of early focus, thoughtful strategy, and effective execution.

It's becoming a cliche to say your product is your marketing, in an era where customers trust each other more than they do media. Well if that's true it might be time to bring a little more marketing into your product, in the form of treating the softer science of brand development with the same respect you give the harder sciences of product management and engineering.

What do you think?  Where do you stand on the Cult of Product? Would love to read your comments.

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Forget The MBA: How About a Masters In Startup Awesomeness?

Posted by Dharmesh Shah on Mon, Nov 07, 2011

This weekend marks the 6 year anniversary of OnStartups.com (it was launched on November 5, 2005).  The OnStartups community has grown -- a lot.  There are now over 30,000 RSS subscribers, and 218,000 members in the OnStartups LinkedIn Group -- making it the largest entrepreneurial community on LinkedIn.  There's also OnStartups on Facebook, with over 27,000 people there.  And, of course, the Q&A OnStartups powered by StackExchange. 

Thanks very much for all of the support and encouragement over the years.  The blog started as a birthday present to myself, but it also had an academic purpose.  I was working on my master's degree at MIT at the time, and as part of my degree requirements, I had to write a graduate thesis. The title of my thesis was “On Startups: The Patterns and Practices of Contemporary Software Entrepreneurs”. I needed some “real world” feedback from actual software entrepreneurs to include in the thesis. I figured out quickly that this would involve talking to humans (something I found reasonably unpleasant). And, I had heard about this “blogging thing” so decided to give it a shot. I took the first two words of my thesis title, tacked it together, and came up with OnStartups.com.

I had a really good time in business school at MIT. Learned a lot, met some exceptional people.  But, I think the whole MBA thing is a little old-fashioned. How many people do you know that want to get really good at business administation? What would be cool instead is a Masters in Business Awesomeness.  The coolest would be a Masters in Startup Awesomeness. Of course, there is no such thing, and no university you can go to get that degree yet (but there should be).  The good news is MIT -- and other great universities are starting to introduce much more entrepreneurial content in their programs. [Shout out to my friend Bill Aulet, chair of the MIT Entrepreneurship Center]

So, below, are some of my favorite (and I think most useful) articles from 6 years of OnStartups.com. If I were to design a curriculum for the Masters In Startup Awesomeness, some of this material would likely be included. I recognize that this a lot of stuff, so feel free to just bookmark this article and read later.

The Best Articles From 6 Years of OnStartups.com 

Sales and Marketing

Startup Websites That Work

Startup Marketing: Tactical Tips From The Trenches

17 Mutable Suggestions for Naming A Startup

The 5 Minute Guide to Cheap Startup Advertising

Building Startup Sales Teams: Tips for Founders

How to Pick a Company Name: Tips From The Trenches

A Geek's Guide to Hiring Marketing People

5 Startup Sales Tips From Turkish Rug Dealers

The 900 Pound Gorrilla: Why Strategic Partnerships Aren't

People

Choosing A Minimum Viable Co-Founder

14 Ways To Be A Great Startup CEO

The 11 Harsh Realities of Being An Entrepreneur

SaaS 101: 7 Simple Insights From Inside HubSpot

Startup Founder Compensation: The Good, The Bad and the Irrelevant

17 Pithy Insights for Startup Employees

Startup Hiring: Why You Should Date Before Getting Married

Pricing

Important Questions Startup Co-Founders Should Ask Each Other

How to Price Software Without Just Rolling The Dice

Startups and the Challenges Of The Freemium Pricing Model

Strategy

4 Quick Tips on Raising Funding Without a Plan or a PowerPoint

14 Reasons Why You Need To Start A Startup

The @dharmesh Test: 16 Questions for Better SaaS Companies

Startups: 10 Things MBA Schools Won't Teach You

Startups: Your Customers Are Not Ignorant, Selfish, Control Freaks

Development Shortcuts Are Not Free: Understanding Technology Debt

17 Pithy Insights for Startup Founders

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Thanks again for all of your support.  If you want to find me online, I'm @dharmesh on twitter and +Dharmesh Shah  

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How To Lose 1% Of Your Customers With Just 1 Email

Posted by Dharmesh Shah on Mon, Mar 28, 2011

• Expectations are key. Short and sweet like my girlfriend. Our emails have always been that way. Then on a great deal we bombarded busy people with 2,000+ words which they weren’t expecting

• Connect with your key customers. I personally emailed most past buyers who unsubscribed. Trying to apologize and learn for the future. We were even able to win some back, http://ericbrown.com/a-lesson-in-customer-relations.htm

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The 5 Minute Guide To Cheap Startup Advertising

Posted by Dharmesh Shah on Fri, Mar 18, 2011

The following is a guest post by Rob Walling.  Rob Walling has been an entrepreneur for most of his life and is author of the book Start Small, Stay Small: A Developer's Guide to Launching a Startup.  He also authors the top 20 startup blog Software By Rob, that's read by tens of thousands of startup entrepreneurs every month and he owns the leading ASP.NET invoicing software on the market in addition to a handful of profitable web properties.

Imagine that you've just completed version 1 of your product and you're preparing for launch. You’ve greased the wheels with a few bloggers, targeted some keywords with SEO, created a bit of linkbait, and scheduled the press release to launch in the morning. At this point your co-founder turns to you and says: “What are we going to do with the $300 we have stashed away for advertising?” Consider this your lucky day. The goal of this article is to provide you with the core of what you need to know about cheap startup advertising as quickly as possible, so you can start spending that ad budget wisely. Let's get started.

Two Key Advertising Strategies

The half-life of advertising traffic is zero. This means that the moment you stop shelling out cash, the traffic stops. The problem is that with typical conversion rates of 1-2% you're paying for 98 or 99 out of every 100 people to walk away and never come back to your site. To combat this inherent wastefulness of advertising, I have two key strategies I recommend no matter which method of advertising you use.

Strategy #1: Try to Get Permission

Seriously consider offering something in exchange for a visitor's email address. It can be a free trial, a free report, or maybe even a free book. But gaining the means and permission to contact that customer again will increase your conversion rate over time in most cases. There is great power in an email list.

Strategy #2: Use Advertising to Test

Use advertising as a testing tool rather than a long-term stream of customers. Very few startups can withstand the cash outlay required to turn advertising into a marketing activity with positive ROI. Even if you figure it out, advertising is a volatile marketing medium. Prices increase rapidly in online advertising as new competition crops up or prospects grow bored of your ad and your click through rate drops. When this happens, all of the time you invested in optimizing your ad campaign is *poof*...gone. So instead of relying on ad traffic as an ongoing stream, use it for what it's best at: the ability to generate a slew of visitors very quickly, and to be turned off just as quickly. This kind of traffic source makes it great for split testing and user behavior testing using tools like Clicktale and Crazyegg. It also gives you insight into how certain traffic converts for you. With properly tracked conversions and an ad on Facebook, you can determine that men from 35-45 convert at a rate 15% lower than women of the same age. This is valuable information, especially early in your marketing effort when you're still trying to figure out the ideal market for your application. Often this is not the largest market; it's the one to whom you can market for the lowest cost. As another example, with AdWords you can learn in a hurry which keywords convert for you, and which don't. This is insanely valuable as you invest the time and money on the long-haul of search engine optimization. Knowing the keywords that really convert for your business, as opposed to the ones that you think will convert, can save you piles of cash and many months of SEO effort.

The "First Five" Advertising Options

With the above strategies in mind, let's look at the first five advertising options you should consider.

Option #1: Niche Advertising

As a startup, there are hundreds of general advertising options available, and thousands more niche opportunities. Depending on the niche you're catering to you should be able to find a forum, blog, magazine or website in which to spend some ad dollars. The tighter the niche the better. Remember that niche sites tend to be cheaper to advertise on and drive more targeted traffic, which makes a huge difference in your conversion rate. (And if you're not targeting a niche because you want your audience to be the "whole world," you're going to need a lot more than $300 in your ad budget). In general, if you are marketing to a niche you will know the sites to target. If you don't it's time to pound the pavement and find out what they are. By "pound the pavement" I mean search on Google and contact people in the niche to find out where they hang out online. Two reputable niche ad networks I've worked with in the past are:

• InfluAds - With an increasing number of advertising "communities" covering design & UX, startups and entrepreneurs, work & productivity and web development, InfluAds can work with budgets as small as the $300-400 range. They sell a minimum set of granted impressions, and if more traffic is available during a month then existing advertisers receive it for free. Image ads only.
• BuySellAds - Though they've traditionally focused on the design & UX space, BuySellAds is in the process of branching into many other niches. This image-only ad network was the primary source of traffic for a design-oriented website I owned, and made the difference between a few hundred dollars a month in sales, and a few thousand. Advertising is purchased by impression or on a monthly basis from individual advertisers, meaning each offers different pricing. But the minimum buy is very cheap - in the $10-$20/month range.

Option #2: Google AdWords

• Ad Format: Text or image
• Ad Components (for text ads): 25-character deadline, 2 lines of body copy @ 35 characters each, 35-character display URL
• Approval Process: Automated, with manual review if you trip a filter

A few years ago, Google AdWords was great for startups. Many niches were untouched, and 5 and 10 cent clicks were commonplace. But these days, the vast majority of niches worth pursuing have ever-escalating click prices as more advertising dollars move online, including dollars from large corporations that don't blink an eye about spending $5 to produce a single visitor to their website. With a 1% conversion rate you need a $500 lifetime customer value to break even. This is more than a stretch for most startups who are scraping by on 0.5% conversion rates and sub-$100 lifetime customer values (at least to start with). But with Google carpet-bombing $75 AdWords coupons to every business in the civilized world, the number of advertisers, and thus the competition, is increasing. For the most part, the days of cheap clicks are over. The $1-2 per click I used to pay to advertise my invoicing software has become a negative ROI for me at $4-5 per click. But all is not lost. There is still a place in the backwoods of AdWords where the wild-west mentality (and cheap clicks) reign. That place is the content network. People traditionally think of Google AdWords as the ads that appear to the right of the search results. But the lesser known cousin of search ads are the ads that appear in every AdSense block you see around the web. These are ads placed through the Google AdWords content network. The content network is less targeted, higher volume, and typically much cheaper to advertise on, than the search results. While we don't have time here to delve into specifics of how to place ads on the content network, the most consistent approach I've seen that works over the long-term is to use their cost-per-action tool called the Conversion Optimizer. There's a great write-up of how it works from Patrick McKenzie of Bingo Card Creator fame, here. There are also some helpful tips on advertising on the content network here. And if you're willing to drop a few bucks, by far the best AdWords book available is the Ultimate Guide to Google AdWords, which includes a section on using the content network.

Option #3: Facebook

• Ad Format: Text with required image
• Ad Components: 110x80 image, 25 character headline, 135 characters of body copy
• Approval Process: Manual (sometimes slow)

Facebook is still viable for startups with its ability to deliver 10-15 cent clicks under the right circumstances. But it's a bit like the Wild West: if you approach Facebook advertising incorrectly you will pay a premium, around 75-90 cents per click. The value of Facebook is its ability to show your ads to exactly who you want to see it based on information in a user's profile. You can easily segment on gender, age, location, relationship status and a number of other fixed parameters, along with thousands of interests and occupations you can target using keywords. The key to low cost Facebook clicks is having a high click through rate (CTR). The key to a high CTR is a combination of a powerful image, an engaging headline, and laser-focused targeting. Due to space constraints we're not going to cover the basics of choosing a powerful image or writing an engaging headline. Not when there are perfectly good articles already written on the subject for those who would like to know more: choosing an image / writing a headline. But once your ad is written, there is a trick to achieving those 10 cent clicks. Based on a tip from my friend JD, I now use the following method with Facebook ads:

1. Target your demographic information so tightly that you can write a headline that addresses them specifically. Example: if you are selling shoes online to the U.S. market, create 10 different versions of the ad, one for each of the major metro areas in the U.S. Also include the qualifying "interests" keyword: shoes. Now make each ad headline address its group specifically, using a formula like "Need Shoes in [city name]?"
2. Start the ads with a modest budget of, say, $5-10 per ad per day.
3. After 12-24 hours review the ads. Some will have high CTRs and costs per click around 10-15 cents. Others will have low CTRs and clicks in the 80-90 cent range.
4. Pause the higher cost ads and increase the budget for the low cost ads to whatever you can afford; $100 per day or more per ad.
5. For a few days you will receive extremely low-cost, targeted traffic. But since you've chosen a small group of people, they will start to tune out the ad rather quickly. At this point your CTR will drop and your cost will climb. Pause the ad, and start over with new cities, new images or new headlines.

This approach requires ongoing maintenance but if you can generate targeted, 10-cent clicks it's worth the effort.

Option #4: StumbleUpon

• Ad Format: not applicable
• Ad Components: just your URL
• Approval Process: Manual

I recently advertised my developer's guide to launching a startup on StumbleUpon. The plus side of StumbleUpon is that all clicks are 5 cents. The downside is the bounce rate is high since people are basically channel surfing. I achieved a 96.88% bounce rate in my experiment, with an average stay of 2 seconds. I wonder if it was something I said? In my test, only 25 visitors stayed longer than 5 seconds. I paid $50 for 1000 clicks, but since only 25 of them stayed long enough to read anything, I effectively paid $2 per click. Your mileage may vary, but through this and other experiments I've gathered the following tips for advertising on StumbleUpon:

• Your #1 goal is to get stumblers to stay longer than 5 seconds. Your #2 goal is to get them to up-vote your page. Paying $50 for 1000 clicks is one thing. Having it go viral and receiving 10,000 clicks for the same price is another.
• Don't send StumbleUpon traffic to a landing page that asks for an email address. StumbleUpon users are notoriously fickle about providing their email.
• People stumble to be entertained, so if your page doesn't have the potential to go viral or turn into linkbait, you will not likely fare well.
• Blog-like content and videos seem to work best. Anything that resembles a traditional landing page will bomb.

Option #5: Reddit

• Ad Format: Text with optional image
• Ad Components: 70x70 image, title, URL
• Approval Process: Manual (two-day lead time)

Reddit uses an interesting approach for their ad pricing: advertisers bid a certain amount per day, all of the money goes into one big pot, and each advertiser receives their share of the impressions based on the percetage of funds they contributed. It's a simple system, but it means there's a bit of uncertainty about what you're going to get for your money. However, Reddit has the potential to provide some very cheap clicks - I've seen as low as 3 cents - if you play your card right. Similar to StumbleUpon, Reddit provides your ad with the potential to go viral. Gabriel Weinberg has a great write-up of the 20,700 clicks he scored for 3.14 cents each for his new search engine Duck Duck Go. His eye-catching image and tech-focused startup served him well with the audience. As he says:

First, a search engine ad is a good fit for reddit ads in general. It has broad market appeal and redditters in general like trying out new technology. Second, I think the ad is particularly well structured. The circular duck icon draws your attention, is contrasting to site colors, and sticks out because it is a circle (as most images are square). I believe the title also has appeal.

Gyutae Park also has a nice write-up of the 434 clicks he purchased for 9 cents each here. One of my recent experiments was a bit more pricey: 187 clicks at 40 cents each. My lackluster performance was a combination of landing on a competitive advertising day, and using a poor-quality header image. In retrospect, I have no idea what I was thinking using this unreadable image: Reddit ads are so simple (just two visible components) that the only tip I have is self-evident: your image has to rock, and so does your title. It's all about choosing an image and headline that makes people click.

Conclusion

To conclude, I want to reiterate what I said early in this article: unless you have deep pockets think of advertising not as a long-term traffic strategy, but as a testing tool to improve your website and find out more about your ideal visitor. Few bootstrapped startups can withstand the cash outlay required to turn advertising into a marketing activity with a positive ROI, but that shouldn't keep you from testing the waters to find out for yourself. I look forward to hearing about your advertising experience and recommendations in the comments.

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17 Mutable Suggestions For Naming A Startup

Posted by Dharmesh Shah on Fri, Oct 15, 2010

Naming a startup is hard.  Very hard.  On the one hand, the pragmatic entrepreneur thinks: “I shouldn’t be wasting time on this — for every successful company with a great name, there’s one with a crappy name that did just fine.  It doesn’t seem like a name has much influence on the outcome at all.  I’m going to get back to writing code.”  I sort of agree with this.  You shouldn’t obssess about your name.  But, you also shouldn’t dismiss it as unimportant.  Part of the startup game is to try and remove unnecessary friction to your growth.  Sure, you could build a spectacularly successful company despite having a lousy name — but why not stack the odds in your favor?   

One more reason why spending calories on picking a great name is important:  It’s a one-time cost to get a great name — but the benefit is forever.  Conversely, if you short-change this and dismiss it completely, you’re going to incur what I’d call “branding debt”.  Not bad at first, and maybe not a big deal for you ever, but every year, as you grow, you’ll have this small voice nagging inside your head “should I change the name of the company…”.  It’s going to be annoying.  And the longer you wait, the more expensive the decision is, and the less likely you are to do it.  Save yourself some of that future pain, and invest early in picking a decent name.  You may still get it wrong, but at least you’ll know you tried. 

One last note before we get started:  Not all of these are weighted equally.  And, remember that these are suggestions not laws.  They’re also mutable. 

The 17 Mutable Suggestions Of Startup Naming

1. Make sure it’s legal!  This should be obvious, but it’s an important step that too many entrepreneurs skip.  Before attaching yourself to a name, make sure that someone else doesn’t already have claim to it by way of a trademark.  In the U.S., you should take a quick peek at http://uspto.gov.  The good news is that if you satisfy some of the other conditions below (domain name, twitter handle, Facebook name), odds are relatively low that someone’s already using the name.

2. Hint At What You Do:  You have two paths to go when picking a startup name.  You can pick a name that is “synthetic” and made-up (example: Wufoo or Quora) or you can use somthing that is somewhat descriptive of what you do (example: Backupify or KISSmetrics).  I lean a bit towards the descriptive side of the spectrum.  But, a lot depends on what you’re building.  Synthetic names are often great in the long, long-term (easily trademarkable, and you can truly “own” them and infuse them with meaning) — but most of the time, I’m more worried about surviving in the short-term.  So, I like simple names that convey a bit of what the company actually does or stands for.

3. Make it easy to remember: How do you know whether a startup name is easy to remember?  You don’t know.  So, test it.  Talk to people.  Describe the company.  At the end of a 2–10 minute conversation, casually ask them if they remember what the name of the company is.  If it didn’t “register” it’s not a failure on their part (and make sure to tell them that), but a failure on your part for not having something that’s memorable enough.

4. Make it unambiguous when spoken:  A quick way to test this is to ask friends and family what they think of the name over the phone — and ask them to spell it back to you.  If a decent percent of them get it wrong — or are uncertain, you’ve got a problem.

5. Make it unambiguous in Google:  Many of the tricks of the trade you’ll use to monitor conversations that mention your company on the web will involve doing some sort of search.  If your name is something like “Pumpkin”, you’re going to have a harder time distinguishing when people are talking about the generic term, or when they’re talking about your company.  Of course, there are plenty of examples where a startup started with a generic word and went on to be pretty successful (Mint.com jumps to mind).  That’s why these are suggestions (not laws) and they’re mutable. 

6. Start early in the alphabet.  In the pre-Google world, this was done so that you’d show up earlier in a lists of things that are often sorted alphabetically (like when you win an award).  In the post-Google world, a similar rationale applies, but what’s more important is the position of links to your website when it shows up in a list of things (like a directory).  If possible, you want to be in the first page of a multi-page article that mentions a bunch of companies.  The first page of a multi-page directory usually passes more SEO authority to your website than subsequent pages.

7. The “.com” has to be “gettable”.  By “gettable”, I mean that it is either not registered yet — or, it is available for purchase at a price you’re willing to pay.  Don’t play tricks with the domain name either — like including hyphens.  Also, stay away from clever domain names like del.icio.us.  The reason is simple:  It’s not natural for people to type domains that way.  (Note: Even del.icio.us eventually switched to the much easier domain, delicious.com).

8.  The twitter handle has to be available.  No tricks with numbers and underscores and stuff.  You want the most natural, obvious twitter handle that matches your company name.  This is not quite as hard as .com domain names — but getting harder every day.

9. The facebook page should be available:  To test this, try visiting http://facebook.com/yourname and see if there’s something there.  Or, do a search on Facebook and see what you find. 

10. Keep it short.  Always good advice, but particularly true in the age of Twitter.  The more characters in your company name, the more characters in the tweets that people write that mention your company name.  The more characters your company name uses up, the less you can actually say in a tweet.  Generally, try to stay 10 characters or under.  Also, number of characters is not the only consideration, it should be short when spoken as well (that is, have fewer syllables).  The fewer the syllables, the easier it is for people to say.  Great examples of one and two-syllable names:  Dropbox, Mint, FreshBooks, ZenDesk.  I’d shy away from anything that is over 3 syllables.

11. Don’t leave out vowels or add punctuation.  Just because Flickr was successful does not mean it’s OK for you to drop vowels from your name.  Name your company in whatever way is natural — for humans.  And, don’t add punctuation (like an exclamation mark) to your name.  Yes, it’s distinctive and it worked for Yahoo! but there’s no sense spending calories on this. 

12. Try to get your main keyword into the name.  This helps with SEO and signals to potential visitors what they might find on your site.  For example, this site is called OnStartups.com.  Not particularly creative, but you have to admit — it’s clear.  (And, is likely partly responsible for my high rankings in Google for a bunch of startup related words).

13. Start with an uppercase letter.  If it’s good enough for Google, Amazon and a thousand other really successful companies, it’s good enough for you.  Sure, starting with a lower-case letter is cute and might demonstate some humility, but 99% of the people are going to spell it wrong and you’re going to spend too many cycles worrying about training them — and you’re still going to fail.  If you’re going to ask the world a favor, save it for the big stuff — not “can you please be sure to spell our company name with a lower-case letter”.

14. Don’t name your company after yourself.  Yes, I know it’s tempting because it’s so easy.  And, you might even think “hey, customers should know who they’re doing business with”.  You might even make an argument like “there have been plenty of successful startups that were named after their founder.”  Though that might all be true, on average, this is a losing approach.  When customers hear something like “Dharmesh Shah Enterprises” (granted, your name is probably not as odd as mine), it doesn’t make them immediately think “Wow, that must be an awfully cool/successful/stable company”.  It sounds a bit amateurish right at the get go.  The other reason is that if you name the company after yourself, too many people are going to want to talk to you.  That’s ok when you’re the only person in the company to talk to, but becomes problematic as your startup grows and there are other people trying to sell/support/market.

15. Don't Use An Acronym:  These were all the rage at various points in time -- but I'm not a big fan.  It's hard to get emotional about a three letter acronym.  It's hard to hug an acronym.  As a corollary to this, try not to have a company name with three words in it, because it's long enough that people are going to be tempted to reduce it to an acronym.

16. Have a story.  When someone asks (and they will), so why did you pick X for your name, it’s nice to have something relatively interesting to say.  Names are a part of your personality, and the absence of a personality is rarely a good thing.  For example, when I started my first company (I was 24, and didn’t know what branding was), the name I picked violated many of the rules in this list.  The company name was “Pyramid Digital Solutions”.  But, it had a pretty good story.  I started first with the acronym P.D.S.  I wanted to name the company after my dad (whose initials are PDS).  He’s a tad superstitious and didn’t want me to name the company after him (it’s  a long story).  And,  wanting to prove him wrong I started with the acronym PDS.  Then, for the first word, I picked “Pyramid” because I was passionate about strong, architectural software design.  We were going to build products that stood the test of time — much like the Pyramids.  The other two words (Digital Solutions) were sort fluff words.  Summary:  It’s OK to be purely scientific in your name selection, but a good story never hurts. 

16. Pay attention to character sequences in multi-word names:  This one’s a bit subtle.  But, if you have a name that is two words stuck together, then be mindful of what character ends the first word, and what starts the second.  I’d stay away from names where both of those letters are the same.  Example: If your company name is something like BetterReading, it’s sub-optimal (because Better ends with “R” and reading starts with “R”.  Normally, that’s OK, but when you type it out as a URL, people will often see:  betterreading.com — which is not terrible, but does cause the brain to “pause” for a micro-second because it feels a tad unnatural.  And, I’d be remiss if I didn’t bring up the widely popular example of unfortunate character sequences:  expertsexchange.com.  When capitalized properly, this name is just fine (ExpertsExchange) which is what the site owners intended.  But, it turns out, this can be confused as “ExpertSexChange” (which is not what was intended).  Make sure you think through the combinations properly.

17. Seek timeless instead of trendy:  It seems that every generation of startups has their own “trendy” approach to names.  Examples are the dropping-vowels thing (like Flickr), the breaking up of words (like del.icio.us) or the newly fashionable “.ly” names.  I’d suggest that names that don’t necessarily indicate when you started are a good thing (on the off-chance that your company outlives that particular fad or trend).  Pick a name that is timeliness.  One that people will see 10 years from now and not think “Hey, they’re one of those companies…”. 

That’s all I have for now.  For more on the topic, you might want to check out Guy Kawasaki's article on the topic (makes some similar points, but he's a better writer).  Also, hat tip to the "22 Immutable Laws of Branding" whose title was an inspiration for this blog post.  More floating around in my head, but I’m a believer in the “release early, release often” mantra.  So, what do you think?  Any other tips or rules of thumb you use when coming up with startup names?

Oh, and I'm thinking of creating a simple web-based tool that assesses a name (which I think is hard to do via software).  What do you think of that idea?  What kind of features would you want to see?

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