As a technology-focused founder, what could be better than building a cool new machine?  Innovating for its own sake is fun, challenging and it lets you learn powerful new tools.  A clever new technology is seductive – you want to tinker with it, improve it, add features, tweak the design.  But great technology most certainly does not imply a great business model.  That’s the Technologist’s Curse – a technical founder falling in love with his or her new machine and losing sight of the underlying business case for the product.

I’ve certainly been guilty of that myself.  Take the legal services profession – it’s an area that by any measure is crying out for technological innovation.  Law firms frequently still use Windows XP and Office 2003.  Often it’s easier to find things on Google than your own expensive knowledge management system.  And as a lawyer, you spend so much of your day fighting with the technology you already have.  Getting the formatting right on a big agreement is one task that every corporate lawyer has struggled with.  It’s so deeply frustrating to attorneys – all you want is to get something out to your client and it usually feels like the tech is the thing that’s slowing you down.

For me, once of the biggest frustrations was looking at the same type of agreement again and again, yet not having any easy-to-use procedure for ensuring it had all the language I wanted.  There just must be some way to avoid reinventing the wheel again and again (not to mention relying solely on my own experience and judgment rather than using a sort of checklist to back these up).  My solution was simple – I’ll just build a machine to check over the contract to ensure it contained everything it should contain!  Easy!

Legal language is rarely drafted from scratch – you almost always work from a model.  An attorney’s nightmare is having a judge say, “You drafted this term differently from what every other lawyer from time immemorial has drafted.  Therefore, you must have intended a different result.”  Legal text is deeply conservative and thus it lends itself to lexical analysis more than free text language.  That’s when the seduction began…

Text analytics is tantalizing since you can get pretty good results without that much effort.  But that’s when things start getting much, much harder.  There are a plethora of algorithms, techniques and black magic in text analytics, from natural language processing to grammatical parsing to the Porter stemming algorithm to all sorts of machine learning tools.  Fidgeting with the various levers typically improves one type of result while degrading another.

Thus it’s easy to fall into the “just one more adjustment” mindset that eats valuable time without necessarily providing any business-level benefits.  I spent months trying to get this right – I’d tweak one setting, get a small improvement, but it would break something else.  Being a prudent, Steve Blank-reading entrepreneur, I tried during this time to get customer validation that the vision was actually something valuable.  As it turned out, the technology that got more enthusiasm was actually simpler – instead of actually getting into the interpretation of specific provisions, it was enough for now just to classify them for user analysis.  That alone saved lawyers tons of time and helped prevent mistakes.  But learning this was a painful lesson that only sank in after making these mistakes myself.  That’s like so much of entrepreneurship – you’re aware of this advice on an intellectual level, but unless you’ve done it before, you just don’t know what it feels like to get it right.

A corollary to the Technologist’s Curse, and one I’m really focused on now, is just-one-more-feature-ism: if I build just one more feature, people will start buying in droves.  This is rarely the case, but to people who regularly use, build and even enjoy technology, the power that comes with additional features is seductive…and the coding behind them is just so clever!

There’s something to be said for at least one founder without a deep, behind-the-scenes understanding of the underlying technology – it’s easier to have some distance from your product and see it more objectively.  If sales aren’t going as quickly as you want (isn’t that always?), a technologist naturally focuses on what he knows best – the underlying technology – despite evidence to suggest that this might not be the problem at all.  That’s where an objective set of eyes is really critical.

Photo Credit: Tantalus – Giulio Samuto, 1565, illustrations to Ovid’s Metamorphoses, in Modern Languages / Anthropology 3043: Folklore & Mythology. Laura Gibbs, Ph.D.

Being an entrepreneur isn’t for everybody.  I tend to think it’s something you’ve either got in your blood or not.  Regardless of the hardships, the excitement, the ups and downs, I think those who have the bug will become entrepreneurs no matter what.  So for those who take the plunge, here are some things I experienced when I started GreenLine Legal.

1. You’ll have trouble getting people to pay attention.  If you came from a well-recognized company or firm, that name has real power.  Especially if you were a junior person at your previous employer, people would listen to you because of the brand name (and all that time you thought it was because of the valuable things you say…).  As an entrepreneur, you need to prove yourself, over and over again.

2. It can be very lonely.  Starting a company requires you reach far down into your reserve of self-confidence. Remember the scene in “There Will Be Blood” when Daniel Plainview is chipping away by himself in his oil prospecting mine (and then breaks his leg and almost blows himself up)?  You must be comfortable going it alone, though of course having a co-founder or two significantly eases the psychological (and literal) burden.

3. Nothing happens unless you make it happen.  If you don’t build your product, nobody else will.  If you don’t sell, market, negotiate, plan, hire, manage or raise capital yourself, it won’t get done.  You lose the comfort of having others to cover for you in a pinch.

4. Nobody tells you what to do.  This is perhaps the biggest mental change when you start off on your own.  You can (and should) get advice from those who have been through it before, but nobody will tell you where you need to focus each day.  This is actually one of the best parts of being an entrepreneur once you get used to it.

5. You are responsible for what happens.  Responsibility, for those who take it seriously, is hard.  Sure, there are benefits of being in charge, but if things go wrong, you take the blame.

6. People won’t understand what you’re doing.  This is particularly true for people who aren’t your target customers.  The usual response that I’ve heard again and again is, “Well, that’s very exciting!”, similar to when you told your parents you wanted to become a rock star.  I think this is really just a cover-up when people think you’re off your rocker and are building some bizarre contraption that nobody will want (though of course this isn’t the case with you…).

7. You’ll be afraid.  At least in my book, fear is the inevitable companion to entrepreneurship – fear of screwing up your career, burning through all your money, watching your classmates and former colleagues rise in their professions, rejection by customers and on and on.  Fear is an emotional reaction to risk (risk = uncertainty x severity of consequences), and as such, some people feel more, others less.  But however much anxiety you experience, you need to find a way to live with it.  Reduce risk by (i) decreasing uncertainty and (ii) decreasing the severity of consequences.  Decrease uncertainty by doing things that make it more likely you’ll succeed – listen and understand your customers, carefully budget your resources, get advice from those more experienced than yourself.  Decrease the severity of consequences by taking small steps and scaling – make incremental changes where failure won’t make or break you and don’t incur big expenses before you actually need to.

8. You’ll make many mistakes.  You’ll be making decisions in the face of massive uncertainty.  Some of those decisions will be wrong – it’s best to accept this and try to learn from them.  Avoid getting into a decision that is make-or-break by taking incremental steps.

9. You’ll hear “no” more than you ever have before.  If you’ve done well in school/work/sports or whatever, you won’t be used to hearing no.  You might have gotten a couple no’s from potential employers or the schools you applied to, but the ratio of no’s to yes’s wasn’t anywhere near where it is when you actually try to sell something new.  It’s hard when people say no.  You want to blame them or think they don’t understand the value of what you’re offering.  But you’ve got to learn from them – they will tell you critically important information if you dig a bit deeper.

10. Am I employed?  Starting a company is nothing like “having a job”.  It doesn’t feel like work.  On one hand, it’s lots of fun, but on the other, it’s seven days a week, think-about-while-you-can’t-sleep-at-night, live, breathe, eat, drink work.  It’s gritty.  You’re in the trenches.  If you gave up a decent salary or a well-known employer to start your company, you’ll need to get used to doing without this buttress to your self-esteem.

11. High Highs, Low Lows.  It’s a bipolar existence – one day you think your company is going public, the next you’re about ready to start looking for a “real” job.  I wish there was a better way to dampen the swings, but I think until you’re either profitable or at least scaling a verified business model, it’s up and down, over and over again.

Again, certainly not for everyone, but if it’s in your blood then nothing else can really compare.  Each day you create something new – it’s the ultimate blank sheet.  The rewards are consummate with the risk, though I believe many entrepreneurs’ minds are wired differently for computing risk.  But whatever you do, successes and failures, ups and downs, just make sure you enjoy the ride.