Your Entrepreneurial Spawn

Recently I found myself going through a bit of a ‘thing’ – in a good way. Certain forces within the confines of the CitySquares fortress have forced me to think about some exciting opportunities on the road ahead, as well as some challenges that I’ve never had to face before. And just as I’ve had to think about these good and exciting things, I’ve also had to think about worst-case-scenarios, as the market and economy put a damper on things and forced us to have backup plans. These things, coupled with a few family emergencies and close-calls, have caused me to shift my focus a little bit. You know how if you look at something bright for a little too long it can stain your vision for a short while? Well, think of entrepreneurship as the source of bright light, and the rest of reality as the backdrop to the stain. Let me explain…

As this company grows and gets closer to cash flow positivity, and as we continue to rack up traffic numbers, questions come to mind, like, “what next?” and “what does this really mean?” On the flip side, when the economy nosedives, and our primary markets stop cooperating so well, I’ve also been forced to ask those same questions but in a very different context. What a conflict! Furthermore, there was a very close-call with a member of my immediate family. These personal/family moments have a way of acting like gravity and pulling you down to earth very fast and hard sometimes.

So, these things have forced me to pause for a bit and think about who I really am. Because in either scenario, entrepreneurial success or failure, I am left with one single common denominator – me, myself, and I.

When you a third of your life dedicated to entrepreneurship, you inevitably become party defined by it. Things change. Your perceptions change, as well how others perceive you, including friends and family. Suddenly you’re no longer defined by the things that always defined you, but now you’re defined by what you spend 24/7/365 on – your business, your entrepreneurial drive. You are truly and without a doubt, true and through, an entrepreneur.

This changes you, and I’m not so sure it changes you for the better. Why? Because you lose a part of yourself. It’s unavoidable. When you put so much of yourself into one thing, for so long, you inevitably have to sacrifice other parts of yourself. It’s simply impossible to be an entrepreneur without sacrificing other parts of your Self. And when the business you create starts to take on it’s own life, its own characteristics, its own heartbeat and blood flow, suddenly you realize that it’s not a part of you anymore, it’s an entire entity unto itself. This entity is a being, if you will, that is the very personification of your entrepreneurial passions – its the result of it. It’s your entrepreneurial spawn, and it embodies everything that defined you.

I experienced this event, if you will, over the past several months, or rather, this epiphany. I had to ask myself, what if this thing actually, really, seriously takes off!? What if it really, actually, seriously becomes something!? What if it actually meets or exceeds my most realistic expectations? Or contrarily, what if it flops? What if the economy strangles it? What if outside influences and forces suffocate us? In either event – what happens to me? What do I do? Who am I, then?

So, here I am now, writing this post post-entrepreneurial-identity-crisis, I think. And I also think I’ve figured it out so some extent. I’m working hard now at trying to gather some of the missing pieces back together because I am not defined by my business, by my profession, by my entrepreneurial passions. I am defined by other things, who I am, how I treat people, how my family and friends view me, how my community views me. That is who I am, for better or for worse. I’m getting back to more balance in my life, and so far, I’m loving it.

The moral of the story is probably obvious – but just for the sake of clarity: As an entrepreneur, do not lose yourself. Do not lose sight of who you are and of the big picture, and of what’s really important in life. Maintain a balance in life. Many many years from now, when you are on your death bed, breathing your last few breaths, you will not utter words about how you wish you made more money, or how you wish you accepted that VCs terms, or shouldn’t have sold your company to Big Corp. You will think about family, about friends, about places you’ve been in the world, about those most simplest of things. So enjoy what your doing right now, and if you’re not, make a change.

I’m still trying to figure all this out, I definitely don’t have the answers. I may never have the answers! This is probably one of the big questions in life, ya know? I just know that I found a new perspective, and it’s working in the most meaningful ways.

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Perspective

Today’s New York Times had a brief but attention grabbing article on its cover page titled “In Web World of 24/7 Stress, Writers Blog Till They Drop.” Greg Sterling responded before the sun came up in Oakland, Om Malik also responded, and Michael Arrington is quoted in the article saying, “At some point, I’ll have a nervous breakdown and be admitted to the hospital, or something else will happen. This is not sustainable.” It’s truly shocking to me sometimes how so many people I know, or know of, who are also so bright and intelligent, choose to work themselves to … well, to death. Don’t get me wrong, I’m including myself in at least the later half of that statement. I work 90% of the time I’m awake, and I, like Michael Arrington, have a sleeping disorder. I’ve been to neurologists for it and I’ve undergone sleep studies and the doctors ultimately conclude that I need to relax and get into a more consistent sleep schedule. So I’m guilty of it too. But I like to think that I’m getting better at it and that I do have some perspective.

Work can quite literally become one’s life, making the delineation between “work” and “life” nearly undetectable. Many of my own friends and family would say that CitySquares is Ben, and some might dare to say that Ben is CitySquares. Frankly, I find both of those assessments bordering on offensive, but I do understand their perspective.

What drives me might be different from what drives, say, Om Malik. What drives Om might be quite different from what drives Mike Arrington. And as an entrepreneur on my second business, and knowing many other entrepreneurs in varying stages, I can comfortably say that I know what drives me, but I cannot profess to know what drives them.

Over the past few year I’ve learned a good amount about balance too though. Sometimes a death in the family brings you back to earth, or the birth of a child – whatever it may be, but usually a major life event has a way of doing that – giving one perspective. I’d like to think that I don’t need a life event to remind me. Om Malik needed a heart attack to bring him back to earth. I’ve had some of my own personal wake-up-calls that I frequently use to keep my feet on the ground. I am constantly reminding myself that nothing is more important than family and health. And ironically, it’s precisely those two things that I’m working so hard for!

I’ve forced myself into a pattern of a fairly regular sleep schedule, which has significantly lessened the symptoms of my sleeping disorder. I’ve also learned to set time aside for the most important people in my life as well as time for myself. I’ve been practicing turning off the Blackberry, closing the lid on my laptop, taking a deep breath and just – letting go. But if I don’t practice balance, and it does take practice, than I start to forget why I’m doing all this, why I’m working so hard, why I choose this life – rather than this life choosing me.

This blog, Your Suspect, is most often about these very themes – these struggles between my own identity and Self, and my identity as an entrepreneur. I hope that this blog will tell a story one day, a story that I am living and that I plan on sharing with my own child.

I’m reminded of a line from John Lennon’s “Beautiful Boy”, Life is what happens to you while you’re busy making other plans.

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Why I Will Succeed

I write this post with a heavy heart. I recently lost a close relative, in tragic fashion. As untimely as death is, this one really was untimely. My wife and I spent the past seven days with family in Florida and NY.

In the midst of all this I had a board meeting, some deadlines, and other work activities that still needed tending to. Thankfully my team at Citysquares had things well under control and I knew I could count on them to make sure things run efficiently and that the impact of my absense would be minimal. I found myself confident that I could be away from the office. Of course, having a BlackBerry sure helps.

Anyway, during the past several days, having the confidence that the company was running on its own, and disconnecting myself from day-to-day operations, in addition to mourning the loss of a loved one with my family, I found myself being reminded of why I’m doing this entrepreneurial thing. I was reminded not of fame and fortune, not of career advancement, not of fancy boats or cars. I was reminded of the importance of family. I’m 31 years old, I’m married. We want children. I have a big family, here in New England, in NY, and in Florida. I have a life to build and to live.

I’m doing this Citysquares thing for good reasons, reasons other than fame and fortune. The #1 reason is so that I can build a life for myself, my wife, my family. And that reason makes it all the more important that I succeed.