Point Counterpoint: Entrepreneurship

There are a lot of gainfully employed people out there who are considering the entrepreneurial path. I meet them all the time. Some are nascent entrepreneurs who have the idea but they lack the courage to just do it. They point to many things as reasons, excuses, rationalizations, what have you. Oftentimes these folks are listening to their gut – which is a good thing. They’re afraid of something, and they don’t quite know what it is. Having been on both sides of the equation, I thought I’d present my own version of Point Counterpoint based on some of the things I’ve heard wannabe entrepreneurs say to me. But first, a little history to create some context.

After futzing around in sales for a bit, I jumped into the high tech industry in the mid 1990’s and worked in a wide range of roles for Fortune 500 companies like DEC, GE Capital, Bell Atlantic, among others up until late 1998 when I joined a Cambridge, MA based dot com. That variety of work in the high tech and Internet industries provided me with incredibly valuable exposure, experience, and skills. It also fanned the flames of an entrepreneurial spirit that I think I’ve had all my life. After surviving several rounds of layoffs at the dot-com, my day came on January 4, 2001. The next morning, I woke up and told myself I was done being “an employee” and decided to start my own company, using the skills, experience, passion, gusto, and entrepreneurial energy that was now almost uncontainable. Hindsight being 20/20 of course, I started that company for a mix of the right and wrong reasons. The second company, CitySquares, I started for all the right reasons. I don’t need to walk you through my next 10 years, so I’ll jump ahead.

On January 4, 2011 (10 years to the day), I became “an employee” once again, not at a company of my own founding, but as Litle & Co.‘s new Vice President of Marketing. It’s been six months in this new role; at a successful, profitable, 200 person company, with a 12 person Marketing team, and I can say with both pride and joy that I’m very happy.

Having a solid decade of hard-nosed, scrappy, sometimes bloody, mostly enjoyable, and relatively fruitful entrepreneurial experience has given me an entirely new perspective and approach to being “an employee.” The kind of professional maturity, growth, and development that being an entrepreneur provides simply can’t be gained with any schooling or, I believe, traditional employment.

Point 1: I just can’t work my ass off, put in long days, week after week, month after month, year after year, all while putting up with someone else’s bullshit, stupidity, and politics with no real upside and payout at the end. So, being an entrepreneur puts me closer to the end-game, puts me in the drivers seat, and because I’m in charge, my success or failure is almost entirely up to me.

Counterpoint: That sounds really nice, and I said the same thing 10 years ago. The reality is that while, yes, you do end up in the drivers seat, you are in charge, your success or failure is almost entirely up to you, you still need others to get there. Unless your Tim Ferris, you’re going to need some partners (of some form), some staff, legal and financial services, and if you have half a brain you’ll leverage an advisory board. You might even need capital, and hence you’ll end up with interested shareholders, perhaps a board of directors. So yeah, now you’re the one creating the bullshit, the stupidity, and politicking. While you’re the one in charge of your success or failure, you’re also the one in charge of everyone else’s success or failure too. How’s that for pressure? How’s that for long days, weeks, months, years? The likelihood of “success” is no greater or lesser because you are in charge, if anything you just created more obstacles for yourself. It really boils down to one thing: how you define your success. Success means different things to different people, I’ve opined on this quite a bit here on this blog. So think about what you really expect out of this move you want to make, and sit on it for a while.

Point 2: I’ve got a killer product and I don’t want my employer to have a piece of it – it’s my idea, so I’m going to start my own company.

Counterpoint: Really? The only way is by yourself? I’m glad Christopher Columbus didn’t say that, or Neil Armstrong. Even Leonardo DaVinci had help from the Catholic Church. So OK, you’re the genius with the killer product, but you need to do product stuff right? Cool, and congrats on that title by the way, it’ll come in handy when the going gets tough, or when real business matters need attention – cuz you’re pretty much off the hook. Oftentimes you hear the “product entrepreneur” say, “I just need a partner, someone who can help me raise the money, move some product (aka ‘sell’ the product) while I build it.” There is nothing more annoying to me. If you’re an entrepreneur, you need to do that stuff too, jerk! So, because you’re the nerd with the new gadget you get to scurry off into a corner somewhere while everyone else protects you from the bad people who want to make money off it? How dare they! Maybe you should go start a non-profit then, or build it and give it to a third world country – all so you can sleep better at night and keep your moral high-ground. Face facts Wozniak, you need to get some skin in the game too. Being an entrepreneur is about making business decisions, not product decisions. You don’t get to bake your cake and eat it too, while others sell the cakes, clean the bakery, and stock the shelves. You need to develop some real business skills, skills that will pay off for you in the end. If you don’t develop those business skills, everyone else will figure out a way to take your toy from you while you’re picking your nose. Trust me on this, those bad people who want to take your toy and get rich, they got skills – they’re trickier than you are. You might be a genius, but they’re snakes. Smarten up, and think twice before you hit the streets with your fancy new toy. In fact, given all this, if you really don’t have the chops, really don’t have what it takes, maybe you wanna reconsider talking to your employer about it – but talk to a lawyer first (you know, the bad people who do law stuff).

Point 3: I have big dreams, man. I wanna live this life, I wanna go places and see things, but I wanna do it in style – like on my own yacht, with my friends. You know, I wanna be a pimp!

Counterpoint 3: Playa please! I can’t even respond to you without wanting to punch your mouth. Ya know what – you’re right. Go out there, baller, get that money. I’ll be right here when that album you were gonna drop falls through the cracks, or when your steroids website costs more to build than it ever generates in cashflow, or that “super connected” club promoter ends up being shady and stops returning your calls. Yes, lightning does strike and some people in this world (out of 6 billion) do get rich quick. But if you get struck by lightning, it ain’t gonna make you rich, it might make you a bit brighter though… we can only hope.

Point 4: I just can’t work for someone else. I need to work at my own pace, in my way, with my style.

Counterpoint 4: You must be a millenial. I bet you went to a Charter school too. Hey, I mean that with respect – you are indeed one of god’s special creatures. This world is going to be a much better place once those baby boomers and gen-x’rs are outta the way. I honestly don’t know what to tell you, Moonbeam. I think you have some really really hard lessons ahead of you, and you’re going to find out that mommy and daddy learned the hard way too. They tried to protect you, they really did, but they were kidding themselves and actually doing you quite the disservice. Where’s Tiger Mom? Can you spend a couple days with her? I think she’s onto something. No one appreciates the beauty with which you see the world, and no one quite understands that the world can be a better place if they’d only _____. I think you should lead the way. The fact of the matter here is that no matter what I tell you, no matter what anyone tells you, you are a special creature that needs to experience real pain and suffering before you will listen to anyone. Sorry, that was advice.

Point 5: Life is short, I don’t want to spend it working in a cubicle, or on a construction site.

Counterpoint 5: See above. Also, what’s wrong with work? You know, that’s just a part of life right? You realize that Julius Caesar worked hard, right? You realize that Bill Gates still works his ass off right? You know those special ops guys who killed Bin Laden, Team 6? Yeah, those guys work their effing asses off. Are you better than them? If you don’t want to work, drop out of society and backpack around the world. Or better yet, find something you’re truly passionate about, and find a way to make a living doing it. It’s simple. Now stop whining and get back to work.

I’ll stop there. I hope I’ve made my point. Entrepreneurship is really effing hard, and when people go into business for themselves (be it their own bakery, their own manufacturing company, their own high tech company, ad agency, whatever) – it’s work, it’s hard work. Entrepreneurship is no yellow brick road, Dorothy. It can be, yes, it has the potential to yield wonderful results. You really need to consider the reasons for becoming an entrepreneur. That’s what needs assessment, not how you’ll do it, but why you’re doing it.

Am I better off now than I was when I started? Oh hell yeah. Did I fulfill the dream I had when I started? Oh hell no. But that dream changed with time. I started down the entrepreneurial path when I was 25. I’m 35 now – I’m a different person, with different values, different perspectives, different dreams and goals.

After 10 years of entrepreneurship, personally speaking, I’m a much happier and healthier person, no doubt, and I’m a better member of society. Professionally speaking, I feel like I’m just getting started.

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