Venturebent

I heard an amazing story at my Church this weekend. I drew many parallels from it to my own life including some of the things I’ve learned in my journey as an entrepreneur. The story goes like this:

Alexander the Great’s powerful army spent years overwhelming opposing armies in their conquests. His men were fierce and swelled with the confidence that comes with consistent victory. Yet when Alexander and his men arrived on the shores of Persia they were visibly outnumbered.  Clearly outmanned, his men pleaded that it would be wise to go back and get more men. Alexander responded by ordering the men to burn their boats. As their only means of retreat went up in flames, legend has it that Alexander turned to his men and said, “We go home in Persian ships, or we die.”

One of the key themes from this story I relate to entrepreneurship is the nature of options. The inherent ambiguity you face in an early stage company often causes you to think 2 steps ahead. What if it fails? What if people don’t like the product? Often times these lingering questions can compel us to find ways to hedge our bets…for better or worse.

What I love about this story is that Alexander the Great made one of the bravest decisions anyone can make by intentionally removing his options.  His command sent a message to his men, but more importantly it put them in a new position: one defined by focus where there is no other option but to do your absolute best…or be defeated.

I’ve come to realize startup founders often find themselves similar circumstances. You’re a small company trying to disrupt a space typically occupied by larger incumbents. The odds are stacked against you and the uncertainty of success is evident.

I’d like to believe the odds of success for founders who disengage their options are far greater than those who don’t. Its extraordinary what you’re capable of when you put yourself in a corner. The straightforwardness of succeed or die propels you to do things you’d never do. Coupled with  laser-like focus, this is a powerful combination. Compare this with someone who gets back in the boat when the going gets tough. I know who my money is on.

For the record, I understand the importance of remaining objective, failing fast, and having a backup plan. I think the best founders integrate these things with the all or nothing approach exemplified by this story.

Early on make the decision whether or not you’re going to burn your boats. If you do, successful or not, the simple fact that you gave it everything you had will bring you peace regardless of the outcome. I feel that founders who are truly passionate about solving the problem they have set out to tackle are the ones  that will always be the first to burn their boats. This will be the subject of a future post.

Last week, my fellow Venturebent writer Nick Gavronsky wrote about how critical it is for startups to create their own unique culture and the various ways the initial leadership team can do so.  Part of what goes into the cultivation of this culture is the intrinsic ethos that entrepreneurs and management teams themselves bring to the table.  Oftentimes, the primary component of this ethos is dogged determination, the notion that even if no one believes in your idea, you and your team do — and that is all that matters on Day 1.

Over the last several months, as I’ve gotten to know numerous young entrepreneurs in NYC, I have found this stubborn persistence in every person I’ve met. This attitude was perfectly encapsulated in a recent post by Reece Pacheco, one of the entrepreneurs I’ve gotten to know. After raising a round of funding for Shelby.tv, Reece reiterates the importance of a key mantra: expect nothing, earn everything. This attitude is one I’ve adopted during my efforts to break into NYC’s tech scene, and I’ve also seen it in all the guys on our Venturebent roster as well as others entrenched in the NYC tech scene whether they’ve taken the plunge of starting a company or not.

Alex Taub recently tweeted that he has a circle on Google+ called “Young and Hungry Tech,” a phrase which epitomizes Venturebent’s mission as well as the best part about the NYC tech community. As this tech wave continues, I have no doubt that NYC’s startup scene and the guys I write with on Venturebent won’t get full on current successes, but rather will look to feast on future endeavors.

Over 4th of July weekend I had a great talk with a friend’s Dad whose had a pretty stellar career in private equity. He probably still has American Online and couldn’t tell you what a hashtag is, but the guy is a total sage when it comes to business insight across the board.

We talked about how important it is to find a career that truly excites you: nothing new there. A more thought provoking conversation surrounded how we must objectively evaluate our personal strengths and weaknesses to see where we can win professionally. Its an incredible insight that I think is particularly important for entrepreneurs to think about.

If I was a betting man, or a VC : ), I’d always put my money on entrepreneurs who I think have a competitive advantage. I think an advantage can manifest itself in a few ways: talent, insight, relationships, and you might be able to throw timing in there. If you don’t feel like you have one of these going for you take a look in the mirror and ask yourself how you can win. If your answer is a unique idea my chips are on the other guy.  Let’s break these down:

Talent: Be objective about the talent you have and your chances of winning given those circumstances. Odds are if your team’s technical abilities are limited you shouldn’t try to build the most advanced search algorithm known to man. Unless of course you can hire the person who can do this. Stick to your guns and play ball at a level you can legitimately compete at. You’ll give yourself a better chance of succeeding. I say this not to discourage innovation, but to encourage success. If the sky’s the limit than rock on and let me know what you’re building.

Insight: The term “unique domain insight” is coveted for a reason – entrepreneurs who build businesses around spaces they deeply understand are more likely to win. They can see opportunities others can’t just as easily as they can anticipate potential hurdles and understand how to overcome them – so important. If you have no idea about the space you’re competing in hire or talk at length with someone that does.

Relationships: Sadly its not always the best products that win; sometimes its those who have forged the best strategic relationships. If you have them, good for you – this can make up for other shortcomings. If you don’t, evaluate the playing field and understand who does and what that means for your business. Do you want exclusive access to the twitter firehose for a groundbreaking data service. Better make sure somebody whose doing the same thing hasn’t beaten you to the punch.

Timing: This one is tough to argue because technically anyone interested in building a business has the same timing as you. I think this more speaks to first mover advantage (which isn’t always good) or unique insight into a confluence of factors. Both of these are a bit redundant. First mover advantage ultimately manifests itself as relationships with users, consumers, and partners. Insight on timing is, well, insight.

Ultimately, the thesis of this post requires entrepreneurs to ask themselves one question: are they poised to build the business they’rebuilding? I’m not asking are they the most poised because there will always be people out there who are better suited to do something. I’m asking at some level do you possess something that will enable you to win? Those who can answer yes have a far better chance of succeeding. If you can’t answer yes think about the collective superpowers of your team and where you can win – if you find something there that excites you the sky’s the limit.

Scott wrote a fantastic post earlier today about always finishing.  It really got me thinking about what makes me most productive and I think he’s absolutely right. As I was writing a comment to his post, it got kind of long so I though I might as well just post a short follow-up.

Ultimately, I believe everyone has their own personal strategies and tactics for how to be most productive.  The thing I’ve found is no matter what these things are for anyone individually, three main points underlie what it means to “always finish” and you will find them in all successful entrepreneurs (including Scott): discipline, focus and consistency.

I believe that whether it’s exercise, diet, sleep, to-do lists, careful organization, meditation or any number of things that you find help you do more faster personally, the most important thing – what’s at the core of it all – is that you stick to whatever works for you and have the discipline to stick with it 100% despite everything else pulling you in a million directions at any given time.  By doing so, you achieve ultimate command of yourself through consistently reinforcing the habit of following through, executing and being at your best.

So how do you master this illusive and fleeting state of always bringing your ‘A’ game?  Primarily, I think that it’s embedded in us from a young age by our parents and role models (being surrounded by people with a strong work ethic throughout my life no doubt had a huge impact on me).  However, if you’re looking for something you can control right now – when you feel yourself slipping, start small and build up some momentum sticking to and finishing whatever it is that makes you personally productive.  If I can’t set my mind to something, I just start doing it and that almost always has the effect of setting my mind to it for me.

Want the ultimate fix?  Sure – it all comes back to those same old clichés: Have a passion for what you do and a chip on your shoulder – something to prove, whether to yourself or someone else.  Unfortunately, I can’t help you be passionate about something you’re not.  However, if I really want to be productive and make sure I ‘always finish’, I found that the following never fails: I tell 10 of my closest friends and family members that I’m going to do something and ask them to hold me to it.  If I need even more of a spark, I would offer to pay them each $100 if I don’t follow through.  You will finish – I promise.

If all else fails, there’s always coffee.