“What’s in a name?” A famous question that is as relevant today as the day it was penned. There are a few things that are completely in your control when you think about starting a business or kicking off a new project, and the name that you select is one of them. It never ceases to amaze me how few people give the name selection process the attention it deserves when they are commencing.

There once was a time when you could take a product almost all the way to the finish line and come up with your name then. The companies who really understood marketing and brand management would spend considerably more time on this exercise, but some of them are the worst offenders when it comes to coming up with names. More often than not, what they would bring to market is a line extension, utilizing some portion of an existing brand (i.e. Coke Zero, Miller Lite). They successfully bi-furcated the target market, and end up losing cumulative share.

The Internet changed the importance of a name in a few ways that may not be immediately obvious when you are thinking through a name, but are exceedingly obvious when you hear them said out loud. The discovery process that consumers go through today for information about your product or company will most likely (I really want to say “absolutely will”) begin with a search engine. Thus the question, “what’s in a name?” Perhaps a more contemporary version (much to the horror of Shakespeare lovers around the world) is “how Google-able is your product?”

A great example of this is a language invented by Anders Hejlsberg, and released by Microsoft in 2000. Initially, the code name for C# was “Cool” (supposedly for “C-like Object Oriented Language”), but in an effort to tie the language to the anchor brand of the C programming language, Microsoft opted for “C#” – pronounced “C sharp.” The only problem with this is at the time, the “#” character was a non-allowable character for search engine crawlers. They ignored anything after the “#” because the “#” is used for HTML to mark an anchor on the page. Further, at the time, most search engines ignored the “#” as an input character on the search page. This meant that anyone typing “C#” into a search engine would get a search for “C,” as the search engines would strip out the “#” character. Worse, not only would customers be confused if they found links to the older “C” programming language, but what if they were presented with stock information for Citibank, whose NYSE stock ticker is “C?”

Imagine how frustrating this must have been for anyone who heard about this cool new language and immediately went to the search engines to get more information. Sure, the year was 2000, so search engines were still new-ish, but the primary consumer of a new programming language, especially in 2000, would certainly be search engine savvy. The search would have come up empty, or, worse, pointing to many non-relevant sites.

Further compounding this naming gaffe is the fact that the character “#” is not usable in a URL. What? In plain English, Microsoft could not have the URL “http://www.microsoft.com/c#”. The “# is supposed to represent an anchor within the document, but without addition text after the “#,” the URL doesn’t work. Failing in finding the information in a search engine, a customer might try to simply tack the name of the new product on the end of the company domain. Again, the tech savvy customer who would be seeking this information would be stymied in their attempts. Even today, in 2009, this URL fails.

Typing “www.microsoft.com/c#”

What’s interesting about this is that even today, the Microsoft search box throws out the “#” for the customer. You can see this by looking at the search term presented on the lower left. As you can see, because the URL failed, Microsoft conducted a search for what came after the dot com, and thinks I was looking for “C.” With this as a failure, a customer might spell out “csharp” and find that the URL www.microsoft.com/csharp comes up empty:

Typing in the URL “www.microsoft.com/csharp”

Unbelievably, they repeated this error in 2005 with their new language F#.

When we first started IMSafer, the name wasn’t IMSafer. In fact, that name was more of a serendipitous discovery than anything else. The original name of the company was Collabarent. I was trying to be cute, and was hoping to convey the concept of parents collaborating. It’s a pretty awful name. Tough to spell and even harder to say if you aren’t ready for it.

One of the design principles of the product was meant to harness the collective wisdom of the parents using the system. We weren’t really clear what problem we were trying to solve other than taking on the “parental controls market.”

The challenge put to me by Tommy, my VP of engineering and co-founder, was that we didn’t have any focus. Without focus, and a clearly laid out problem set, there was a good chance that we would try to do too many things, and in fact do none of them well. The name I had chosen had pretty much demonstrated that sentiment.

Tommy took the challenge one step further and suggested that we really ought to spend time thinking about the core problem set, the impacted customers, the feelings we wanted to evoke from those customers, and see if a name would evolve. We set forth the following requirements: The name had to be:

1. “Google-able,”
2. Memorable
3. Not confusing with other products in the market
4. Immediately convey the purpose of the product

We also needed to ensure we could get the domain. You must always, always, always get the domain, and it must be a “.com.”

I want to take a quick moment to hit this point about domains really hard. Don’t underestimate the need, nay requirement, for a .com address. When Microsoft first shipped their Zune player, they didn’t own Zune.com. They do now, but at the time, it was www.zune.net. The same story played out for their Silverlight technology, except that Microsoft still doesn’t own the .com URL.

How many respectable or popular businesses do you know of that have a “.net” URL? Very few. The opportunity cost in terms of lost traffic and customer mindshare is pretty high, especially if there are two commas in your marketing budget. This problem is further exacerbated should your product or company have any level of market success and you decide that you are going to procure the .com address if it’s being squatted. Your market success will have the perverse effect of driving up the price for the .com version of your domain.

Back to Collabarent. With the above guiding principles in mind, we set about on an exercise to enumerate the problem sets we wanted to tackle, list out our customers, and decide what feelings we wanted to evoke. The final test for any proposed name was whether or not GoDaddy told us the domain was available. We came up with a bunch of names, but for one reason or another, the each failed the tests above. Finally, Tommy said, mostly out of frustration, “I just want parents to know their kids can IM safer.” I remember my first thought was that there was no way that domain was available. The likelihood of any seven letter domain comprised of any real words being available in early 2006 was pretty low. IMSafer.com was available. Unbelievable.

Sounds like we had a winner, right? Sort of. There were two problems which wouldn’t present until much later in our cycle. First, my board of directors, and many people we spoke to, often dropped the “r” from the name, and were convinced we were “IMSafe.” We did not own that domain, and spent a good deal of our time correcting people. We failed the rule of not testing the idea with enough people. Had we done that bit, we would have discovered this issue.

Second, the “IM” part of the name had the potential limiting effect on design and product direction. Company versus product name is a discussion for another essay, but it’s something to keep in mind when you are thinking about your company and your product portfolio. By adopting the name of our flagship product for the company name, there was a potential branding issue down the road should we have decided to broaden the scope of the company.

We had a similar problem at AskMe.com. When we started the company, it was known as “Xpertsite.com.” Yes, we spent a good deal of our time repeating the following, in one form or another: “no, w-w-w-dot-x, no e, p-e-r-t-site.com.” Very annoying, and distracting for potential customers. When we switched to AskMe.com, we spent a lot of our time explaining to people that we weren’t Ask.com the search engine. To this day, when I tell people that I worked for AskMe, some people tell me that they “use that search engine.”

The moral? First, make sure that you have a name that can be found in a search engine, and is unique enough that you are not going to get lost amongst the information about irrelevant products. Second, make sure that your name is not only easy to remember, but that it won’t get confused with some other existing product which already occupies some spot in the mind of your potential customer. Third, it helps if the product name immediately conveys purpose or relevance to your target customers. Lastly, make sure you can get the domain name, and make sure it’s a .com.

I don’t know about you, but many times when a supposed flash of brilliance hits me, I believe I have the mental equivalent of gold. I tend to get a bit ahead of myself, and start thinking about all of the money that I am going to make, what the product is going to be, how much customers are going to love it, how I am going to sell it, and who is going to buy it. Somewhere in the middle of that process, I start designing the product; making decisions about the absolutes of what the product will and won’t be.

You will find that your first idea is seldom your best one. This is true along two separate axes. First, if you spend any incremental time on design and storyboarding, you are likely to improve upon the original idea in immeasurable ways. Second, if you start letting your mind wander, you may come up with a completely different product/solution that addresses the same need, either directly or tangentially, and does so in a far better way than your first idea.

Just as the notion of testing your idea with only one person is a guaranteed recipe for fail, using yourself as the sole testing point will likely land you in a situation where you could potentially create something that no one will want. This is especially true if you just start building the first thing is that pops into your head.

Building is something that you should only be taking on after you have thought through what it is you are hoping to accomplish. Let your thoughts percolate for a little. Then let them simmer. I’m not talking about taking weeks or months, but don’t be afraid to let an idea sit for a day or two before you act.

Further, if you have a set of people you trust to not crap on your ideas, you will find that the simple act of trying to describe what it is that you want to do will reveal cracks in your idea. If you can’t explain it, you probably shouldn’t be building it. Even if your colleagues don’t buy into the concept, it’s likely that they will ask questions which will force you to think about what it is you are actually trying to do, and whether or not you are accomplishing that goal.

How many times have you said “I know what I want to say, I just don’t know how to say it?” My eighth grade English teacher would beg to differ. If you can’t explain it to someone else, why do you have any reason to believe that your translation of what’s in your head to an actual product will make any more sense? A great example of this is a focus group. If you have ever sat in a focus group, there’s a high probability that in your head you were screaming something along the lines of “why are you doing that you stupid customer?!?! You’re not supposed to use it that way. No!!!!” The physical instantiation of your idea is simply a representation of your ability to explain what it is that you wanted to do, and if you can’t explain it, you certainly can’t build it.

When I first came up with the idea for IMSafer, the product concept was to have a local program running on a computer doing all of the language analysis, and to have the code based on an open source product called Snort. IMSafer was envisioned as a program which was supposed to trap all of the traffic on a local home network, and perhaps even talk to the house router/cable modem. In not thinking through the idea, and not sharing the idea with anyone, I started making design decisions that were terrible. Awful, actually.

The team and I spent some afternoons and nights at the local Starbucks during the very early formative days of IMSafer, and just the exercise of trying to explain to them what I was trying to do showed me that I was designing something that not only would not scale (that’s a fail), but would also fail the grandma test (“can grandma install and use this?”). There was no way to make a customer friendly and easy to install piece of software doing it the way I originally wanted to do. Here’s a useful tip: any time you have to use the words “network” and “configuration” in a product intended for home use – fail.

It was clear from just the first conversation that we needed to vastly simplify the product, and that meant changing where the code lived. It also meant removing the number of moving parts from the customer computer. Our target customer was a parent in their late 40s to early 50s, and at the time we started IMSafer, that particular demographic was not the most technically savvy. If I had just rushed headlong into development, I would have either made design decisions which would have destined the product to failure, or would have cost me a great deal of time, energy, and effort to redesign when we finally figured out that what we had built was wrong.

All of this reminds me of an old joke that I love:

There’s an old bull and a younger bull sitting on a hill. The younger bull says, “Look at all those cows. Let’s run down and shag one of them.” The older bull ponders this for a moment, considers his answer carefully, and says, “How about we walk down and shag them all?”

The moral? If you take your time and think through what you are doing, you will more than likely get an optimized result.

The funny thing about great ideas – they are most often loved by the creator and completely misunderstood by those around him or her. Imagine Evan Williams trying to explain Twitter (www.twitter.com) in 2006 to people right before he went live with it. How many people do you think told him that a) they didn’t get it or, b) it was a terrible idea?

We’ve already established that passion for the project is one of the most important factors in determining whether or not there is going to be a success or fail. People with whom you share your idea are far less likely to have the same passion for the project that you have. After all, you have come up with this idea in what you would describe as nothing less than a flash of brilliance. In fact, you have probably spent many hours thinking about this one thing; how you would create it, how it will work, and, most importantly, why people will love it. Those around you with whom you plan on sharing this idea have not, and therefore won’t care and won’t get it.

The single most dangerous thing you can do when you have a brilliant idea for some new project is to ask just one person. Overcoming the gap of single denial is treacherous and terribly important for any new venture to see the light of day. After all, you are in love with this idea, but, like most new entrepreneurs, you are probably feeling terribly self-conscious about the notion that somehow you are going to have this great idea that no one else has had. Further, you will have doubts about your ability to execute against it. It’s very easy, then, for a would-be entrepreneur to become a wayward one by virtue of the fact that they asked but one person what they thought of their idea.

The reason people will crap on your idea, in my opinion, is that most people don’t like change. They don’t like things to be different than what they would consider the status quo. The notion of a friend of theirs stepping out on their own, for most people, is just too hard to imagine. Some of us are lucky to have friends or colleagues who are entrepreneurs, and so they understand. However, for the vast majority of the population, they see this change as a risk. People don’t like risk. They like knowing that a paycheck is coming every two weeks and that someone is going to be providing their benefits. They don’t like the idea that those securities go away, and they certainly don’t like new things. Not unless the masses tell them that they need to get this thing. When first presented with this new idea, however, they won’t get it, and in fact will do whatever they can to dissuade you from following a path that would lead to you endeavoring to create it.

I remember one day in college when I had just returned from my first summer internship with Microsoft. I met my best friend during that internship, and to this day I bring up this story any time he decides to shit on one of my ideas. The year was 1994, and the web was very, very new. Netscape hadn’t come out. Mosaic was the first browser, and for those of us nerds in college, we knew about this coming tidal wave. I can still remember the first day I used Mosaic. I knew right then that my world had just changed.

One afternoon we were in the campus store looking at books, and I uttered the single infamous question. Standing there, staring at books about technology, I thought to myself how surprising it was that there were so few books about the Internet. It’s a hard image to conjure, for sure, but I assure you, there once was a time when there were virtually no books about the Internet. I turned to Alex and said, “You know what would be cool for us to do? We should write a book about how to use the Internet for college kids.” I don’t remember his exact words, but the way I tell the story he turned to me and said, “That’s the stupidest idea I have ever heard. Who would buy such a book?”

To set context, this was a time when there was actually a product called, I’m not kidding, “Internet in a Box.”

 Figure – Internet in a Box Product Image

This is back when getting online was very challenging, and there was nothing, and I mean nothing that was readily available for the average Joe. So in my mind, the idea of a book about how to use the Internet for college students made tons of sense. I made the mistake of testing the idea on one college student. He wasn’t my target market, mind you, since Alex easily outclassed me on the technical nerd scale. Asking him made no sense. I did what most of you will do, however, in that I didn’t seek market research from my target market; I didn’t verify that there was in fact a market. Alas, I simply asked one friend. Since I think he’s pretty much one of the smartest people I know, I figured he must be right, and moved on.

There’s no guarantee that had I pursued that venture that I would have had any success, but the market for Internet and technology related books certainly exploded through the mid to late 90s on into the new century. I gave up too early because of my sample size of one.

Here’s another great example of not letting a sample size of one influence your decisions. I had a good friend of mine in college go to Stanford for his MBA. This friend and I had spent many hours working on labs and project teams together in college, and we both held each other in very high regard. So it was with great skepticism that I listened to him tell me about how he was going to start a new business.

It’s so clear in my mind, I remember the exact location. We were sitting in Mel’s Dinner in San Francisco, with another friend of ours, also a Stanford MBA student. Jeff was sharing this idea for a new company he was going to start. He was so excited about it, but I couldn’t be dissuaded from my advice. I said, simply, that bailing on his second year of business school to pursue this company idea was insane. What would happen if he failed? At least if he had the MBA, he would have that as a fallback position. Besides, based on the idea as I understood it, eBay would pound him into the ground so fast that he wouldn’t stand a chance.

At this point, I had been out of business school for a few years and was convinced (COVINCED!) that having the MBA was responsible for opening doors to greater opportunities. So I told him, in no uncertain terms, that making this decision was a huge mistake. I didn’t make much of an impression. Jeff went on to start a company called Liquid Seats, later renamed to StubHub. eBay come along some years later and purchased that company for $310 million. I give myself an epic fail on that one.

The moral? Most people are not going to share your same level of excitement or passion for your project. They will bring their own fears or prejudices into any feedback they give you, and that feedback will most likely be negative. Further, if you are going to spend time sharing your idea, make sure that you share it with more than one person, lest you get dissuaded too easily. Last, make sure you share that idea with people who have actually gone out on their own, and not people who are office dwellers without a hint of entrepreneurial spirit in their body.

I carry a little notebook around with me everywhere I go. I keep this notebook so that I can jot down the ideas for random businesses which pop into my mind. I’ve had plenty of them, and some of them I have pursued with mixed results. When you are considering venturing off, there’s a two part question you have to ask yourself when deciding to get up off the couch and start your next thing which will drive whether you are searching for happy face or sad face emoticon in your email to your buddies.

First, “do you have any relevant experience?” If the answer to that question is “no,” that’s fine. It’s more than fine actually, as many a successful business has been started by someone who was in way over their head. You need to understand that your lack of domain knowledge will necessarily create some hurdles for you to clear, and some of the hurdles universal to all new businesses will get a little bit higher. However, there have been plenty of people who learn on the job en route to building a very successful business. How you ask? Well, that’s the second question.

What is it that can counteract the bludgeon of ignorance? It’s a really important question, and it must have a “yes” answer if your answer to the first question was “no.” “Are you really passionate about whatever this thing is that you want to go do?” You must have a “yes” answer to this one if your answer to the last question was “no.” Without that passion, the hurdles that are going to be in your way are going to seem pretty impassable. It’s that passion for what you do that is going to get you through the hard times, and believe me there will be plenty of hard times.

So what about the other two possible answers? If you have relevant domain knowledge and are passionate about this project, then you are in the best position of all. You are going to clear over many of the early hurdles, and probably have many of the necessary contacts and rhythms to get yourself started. Further, as your business evolves, the likelihood that you run into blind spots is greatly reduced on account of your domain knowledge. Consider yourself in an enviable spot.

If you said you had relevant domain knowledge, but that you couldn’t be passionate about the project, I actually think this is worse than having said “no” to both. How could that be? You’re bringing domain knowledge to the business, so that has to count for something right? Sure, if you care about the problem. If you don’t care about the problem, why on Earth would you sign up for all of the stress of doing this as your own gig? Running or starting a company isn’t all about fun and games, and as we’ll talk about later you will come to understand that there are a great many things that you simply don’t care to do but have to do. Quickbooks anyone? The stories I could tell about my absolute hate and distaste for having to ever deal with Quickbooks are legend.

You see, if you have the domain knowledge it’s probably because you are already working in the field. You have some security associated with that in that you are pulling down a paycheck, have benefits, and can count yourself pretty lucky to have a job. Jumping to something new brings many new risks. When you are ultimately the last line of defense between success and fail, it’s a tough thing to take on if you really and truly don’t have a deep passion for it. You are essentially signing up for your old job, without the security and without the benefits. What fun is there in that? You are basically setting yourself up for failure.

In true business school form, let’s construct a 2×2 matrix to analyze the problem. Along one axis is the “do you have passion” question, and along the other is the “do you have relevant knowledge” question. I’m always happy to put the $50K plus that I spent on my MBA to work to boil down long winded discussions to a really simple 2×2 matrix. Want to hear something funny? There’s an MBA or MBA-candidate reading this right now trying to optimize this matrix. That just makes me laugh to think about.

The genesis for the project came about when my wife was pregnant with our first child. I was surprised at the state of the children’s DVD market. First, some of the titles were/are just terrible. Second, they are expensive given the amount of content you typically get with a DVD. Third, there wasn’t anything terribly innovative going on with the products. I’m a tech nerd, and thought I could do better, so I set about investigating my idea.

The basic premise was to create a series of DVDs that had stories on them, “animated,” and with dual audio voice over (one female “grandmother” and one male “grandfather” voice). Each DVD would have three stories, and a parent could choose which audio track they wanted to hear. The real interesting idea I had for the DVD was that through the use of some tricks in DVD authoring, each story would be made up of chapters, and each chapter represented one page of the story. The chapters would play in the right order, but each chapter actually had three different versions of itself. After the text of the page was read, there would be question asked about something happening on the page. Each of the three versions had a different question. This is akin to how you would read a story to a child. With the randomness element mixed into the ordering of which version of the page played, a parent could get multiple playback value out of the DVD, and would likely never hear the same order. I thought this was huge. Ask any parent how many Dora or Thomas DVDs they can recite from memory, and hate themselves for it.

My wife and I both thought that this sounded like a great idea. I secured the rights to some stories, prototyped the product, fixed some issues, had professional illustrators (hired via eLance) work on contract to bring the stories to life, and had the stories mapped to the DVD. I even provided the voice over work for the first version to save on costs. I pushed this all the way through to the manufacturing of many boxes full of DVDs.

What happened? I didn’t have passion for the project. I got caught up in some other things, and selling kids DVDs is actually pretty hard, especially when you aren’t 100% focused on it. If you want to get on the shelves of the stores, you need to go through a distributor. When you sell retail, there are margin issues. Oh, and retail also has “returns” issues. These were the sorts of things about which I didn’t know anything, and actually didn’t want to know anything about.

Unfortunately for me, I come from a software background, where you sell bits (not atoms).  Bits have zero marginal cost of production, and getting distribution is easy. My passion waned, and I ultimately ended up with a bunch of boxes in my garage. The obstacles that were placed in front of me became impassable. Had I been honest with myself from the beginning, I would have realized I was in the “probably screwed” box, and would have saved myself a ton of trouble and money.

As a side note, if you have a child between the ages of 2 and 5 and are looking for some interesting, limited edition DVDs, please drop me a note.

The moral? It’s OK if you don’t have domain knowledge for your project, so long as you have passion for it. If you are going to get outside of your comfort zone, you have to have that passion or the roadblocks will become impassable and you will fail. Having no domain knowledge and no passion is a terrible spot, because you are placing an order for “risk” topped with “I don’t give a shit.” That’s a recipe for fail. If you do have domain knowledge, and you are passionate about the project, you are in the best position of all.

There could be any number of reasons that I finally decided to write this. I guess the biggest reason is that I keep saying that I will.  The astute reader will note that I have been guilty of breaking the very first rule.  I can’t have that, can I?  Besides, I am not a multi-millionaire, despite having worked for Microsoft through the mid-90s, a dot-com before the bust, and for one of Wall Street’s most hallowed names.  “How could that be?,” you ask.  Great question.  I will attempt to answer that within the confines of the essays herein, but I think the most obvious answer is that I’m just not that good.

That must be the reason, right?  I’m just not that good.  I’m not as smart as I think I am.  All of the talent, schooling, and work experience have failed me in my quest to hit it big.  Of course, I could put forth some of the statistics as they relate to the percentages of people who have actually accumulated a multi-million dollar net worth, but that wouldn’t matter.  Rest assured, it’s a very, very small percentage of the population.

We all know one or two people who have hit it big with the stock options at one of the companies we could name.  I know I can.  The funny thing is, there are a good percentage of the people who have hit it big who can chalk that up to luck more than anything else.  Yes, they were good enough to get hired at the right company, but let’s be honest, there are a lot of people who have ridden coat-tails of luck, and there are a lot of people who just got lucky in getting hooked up with the right company.  And that’s OK.

Another issue is that there’s a real survivorship bias built into the many stories with which you are regaled about the multitude of startup successes, all of which are intended to make you feel some sense of inadequacy with regard to your own progression through life.  Failures are a boring topic about which to write.  Nothing is more exciting than reading about a life you don’t have but want, rather than don’t have and don’t want.  Could you imagine a magazine, like People or Us Weekly, which followed the mundane lives of everyday people?  Call it “15 Minutes.”  That was actually one of my ideas once upon a time.  Unfortunately, trivialities are just not nearly as exciting as reading about fabulous people going to fabulous parties wearing fabulous gowns (i.e. People).

One of the biggest lessons I have learned over the course the last two decades is that if you spend your time comparing yourself to your peer group, you are on the express bus to Pissed-Off town.  The funny thing about going to the “best” schools and working for the “best” companies is that you will invariably know some very, very successful people, even if you are not one of them.  I can name at least 10 personal friends worth over $10 million dollars.  *I* don’t have that kind of money, and might never.  There’s always someone smarter than you, richer than you, in a bigger house than yours, or with a better sounding job.  So what are you going to do about that?  You can spend your time being mad about it, or you can try to learn what they already know about success and hopefully apply it to your own life.

I’ve always enjoyed writing, and I’ve always been a story teller.  I’ve had the wonderful luck of being involved with some of the coolest people and companies during some of the most innovative periods in our history.  I’ve seen some great things, and some not so great things.  Most importantly, I always considered myself a student, and I have made it a point to learn from each of my experiences.  Right now I’m enjoying a break from my last venture – I made what I like to call a “wifestyle” decision, and not head-rush into the next venture (we’ll talk about that in the “Running the Business” chapter).  As I have been thinking about the things on which I am currently working, and the projects which will come down the road, I wanted to codify the many things I have learned so as to create a blue print for the next gig.  During that thought process, I decided I would share it with you.

You see, I got a bit tired of all the books that basically pump you up with inspirational stories and little substance, or try to tell you that their one way of doing something will make you a million dollars.  It’s patently absurd.  You can’t control for luck.  You can’t script million dollar ideas.  You can control desire and work ethic, as well as experience.  Experience tends to trump all.  Experience and the network of people you have around you.  I’ve seen some good blog posts about failure, and I will link to those in the essays.  What I had never seen, in any book store, was honesty about failure.    Honesty about why the author wasn’t a bazillionaire.  Honesty about why their company (or companies) failed.  I actually don’t mind being the lone voice of fail.  I suspect that the number of people who have tried and failed far outweighs the number of multi-millionaires.  We all have a story to tell, and this book is just the beginning.

They say that it’s only a mistake if you do the same wrong thing twice.  The first time is for learning.  What I’m hoping to do with this book is prevent you from making the first mistake.  I’ve made many of them already, sometimes with hilarious results.  I’ve also had some pretty solid wins, and many things of which I am very proud.  With each of the stories, I hope to not leave you thinking “what a drag,” but rather leave you pumped up with a moral of the story.  Aesop I am not, but hopefully the lessons will keep you from reaching The Failing Point.

This is the first essay from the first chapter in my community book “The Failing Point” – essays will be published here online first, and I’m looking for feedback from the community.  The permanent site will be live shortly.  Each essay title finished the sentence “Under no circumstances should you…”

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I can’t tell you how many great ideas I have had in the last decade. I am literally a legend in my own mind when it comes to creating awesome products that everyone in the world must buy. It seems like I have a new idea every day. Here are a few examples:

• Spinner rims for baby strollers
• A teddy bear with a beeper network activated voice box
• A book about the Internet for college kids
• A location based dating application for the iPhone
• An SMS based trivia text game
• Fleece gloves which are sleeve length
• Children’s utensils that have cars, trucks, boats built into the utensil

As much as I would love to believe that I am the master of generating million dollar ideas, one look at this list would tell you that I am as much a fool as the next guy. However, being the eternal optimist, when I came up with these ideas I thought they were, in the words of Kenny Bania from Seinfeld, “gold, Jerry, gold!”

In any event, once I have come up with the most awesome product in the world, I come up with the most awesome name, which of course has the proper awesome domain name available, and then of course I figure out how I am going to promote this awesome product via a blog, Facebook, or even Twitter. The romance period of thinking up ideas often involves thinking I am awesome, which I clearly am not. The challenge is that these are all ideas, without any action plan. I never once put in the time, energy and effort to kick start any of these projects.

As someone who used to be a semi-professional motorcycle racer (which basically means that I paid way more than I ever hoped to make), I can tell you that the time honored tradition of bench racing is not reserved for those of us who used to flog around a track on two or four wheels. As racers, we all used to love getting together after a race and talk about this lap or that pass. It’s pretty funny that I was always faster and closer to the front of the pack the more time that had elapsed from the race itself.

Startups and bench racing go hand in hand. It’s like peanut butter and chocolate (not to be confused with peanut butter and jelly, an abomination I don’t get, which is further compounded by those loons at Smuckers who put them both in the same jar). People love to sit around and talk about that company they are going to start “one day.” Or, better yet, “when the economy improves a little bit.” Or, my personal favorite, “when I’ve saved up enough money to tell my boss to shove it and start my own gig.”

What it is about the startup that has so many people spending so many hours fantasizing about taking on such huge risks, with extremely low probability of success, and really is quite a thankless task? It’s the fantasizing on which they spend so much time. Not the “start”-ing or the “up”-ing (as in – get up off the damn couch), but the fantasizing. Let’s call it aspirational dreaming. All the energy which is wasted thinking about how a person would spend the millions they are going to make when they eventually start their company would be far better served accomplishing tasks toward the goal of getting your idea off the ground.

The biggest mistake that people make is setting some big hairy audacious goal without properly level setting expectations as to what is required to get there. Nerds and tech folks love this big hairy audacious goal (or “BHAG”s as it’s called), because for them it’s like a badge of honor to have accomplished this big hairy thing. A great example of this would be Google. They want to “organize the world’s information and make it universally accessible and useful.” Wow. That’s big. Hairy even. Sergey and Larry didn’t start with that one though. Their original vision was slightly more mundane: “The anatomy of a large-scale hypertextual Web search engine.” You see, before you can start working toward your BHAG, you need to have accomplished a few smaller items to get some momentum.

There is no greater killer of an idea than lack of forward momentum. The easiest way to set yourself up for success is to decide what the end point is, and break the task into a series of smaller tasks. Preferably, there would be some very small, very easily accomplished tasks on the front end such that you can feel like you have made some noticeable level of progress in a reasonable period of time. This is a little trick I learned many years ago. You trick the mind into thinking you have forward momentum. Celebrate some of the early successes. You know what happens next? Each successive step actually requires less and less effort.

Here’s a great example. I’ve been saying I was going to write a book for 15 years now. Why haven’t I done it? All signs would point to the fact that I am quite the able bodied accomplishment engine. How could it be that this over-achieving, type-A person would have so much trouble getting off his ass for one of his ideas? To put in bluntly, it just seemed too hard. Every book on my shelf appears thick and meaty. Lots of pages. Plenty of words. That just seemed like too hairy a goal for me, for whatever reason, and I never got around to it.

This time is different. First, I broke the task down so that I could make progress every day. There was coming up with the topic, then coming up with the chapter topics, then working through the potential names, and of course finally getting around to writing the content. Specifically because I broke down the BHAG (“to be a NY Times Best Selling Author”) into a series of mundane tasks (“come up with a topic”, “come up with a name”, “come up with some topics”, etc) I was able to make some progress quickly, get my excitement levels up, and maintain the energy.

The moral? You can get off the couch and start that thing, whatever it is. If you can’t seem to muster the excitement, you either have a terrible idea, or too big of one. If the latter, then break it down to some smaller pieces and get moving.