Passion Renewed

Just as entrepreneurship requires unbridled enthusiasm, passion, and dare I say faith, so does a job. I know that may come as a surprise to some, because rarely do most of us wake up in the morning and spring out of bed with unbridled enthusiasm for going to their job. But success doesn’t come without it.

I recently started my new job (yes, a job) at Litle & Co., just north of Boston in Lowell. Litle employees a little less than 200 people. It’s a very innovative company that powers the payment processing for brands like Gilt Group, GoDaddy, Overstock, and many others. I’ve known a number of Litle employees for over a decade, including a couple of the executives. As Litle’s new Vice President of Marketing I’ve been asked to affect change not only in Marketing, but within the organization as a whole. Now, I get to take so many of the lessons I’ve learned as an entrepreneur for the past 10 years, and apply them to an established, profitable, growing company as a member of the management team. I’m humbled, flattered, honored, as well as excited, enthusiastic, and passionate. And I know of no other way to go about it.

I’ve been doing my own thing for 10 years – exactly to the day actually. It was January 4, 2001, when I was one of the last people left at an Internet startup in Cambridge, MA, and laid off. I woke up on January 5, 2001 and said to myself, “I’m never doing that again.” So I embarked on a 10 year journey of entrepreneurship, starting with Atomic in the first five years, and concluding with CitySquares over the last five. On January 4, 2011 I started in my new role at Litle – doing it again!

I’ve spent a lot of time over the past several months reviewing all I’ve done, won, lost, learned, and earned over the past 10 years. I’m now in my mid thirties. I embarked on this journey in my mid twenties. How much things have changed. It’s hard to quantify who and what I’ve become, and frankly I don’t think it’s interesting reading. So let me put it like this: For a variety of reasons I did not graduate high school. I was asked to leave actually. I wasn’t thrown out, to be clear, in the classic sense. Rather, I was asked to leave and advised to “start my life.” That was a very sad day. I’ll never forget it. I’ll never forget the feeling I had when I drove by my old high school on graduation day – choked up about what I was missing, about what I’d never experience. Choked up about what my friends were experiencing, about what they’d never forget. Jealous, yes, but sad, regretful, disappointed in myself. Not long after I went out and got my GED, something I’m embarrassed to admit here publicly. A few years later I tried my hand at college, at Bunker Hill Community College. That lasted one semester, barely.

A few months ago I was speaking at Boston College to a classroom full of business students, studying entrepreneurship. It was my third time speaking at BC, at the request of a wonderful professor. One of the questions asked by a student was where I’d gone to college. It was very difficult to answer him. He, a student at BC, and me a high school dropout and entrepreneur on the cusp of selling his company. My reply was awkward, but truthful. I learned by doing. I learned by failing, by succeeding, by winning, by losing. I continue to learn that way. But that’s my way, not a way that works for everyone. He asked what my secret was, a question that also made me feel awkward, as if I had a secret, a genie in a bottle. My answer was simple: passion, but it’s not a secret. Passion, attitude, perspective, these are qualitative attributes that we all possess.

This blog has long been about entrepreneurship, pure and simple. For the foreseeable future I’m taking a long break from entrepreneurship. I’ve got a lot more on the job training to go through. I still have some rough edges that I need to smooth out. And I don’t have any patience for investors. Litle is providing me with fertile ground for me to continue spreading my roots. The company is at an exciting inflection point, facing challenges I can help with, no investors, unrivaled technology, talent, a legacy that won the #1 on the Inc. 500, a customer obsessed culture that won the prestigious Stevie Award last year and is nominated for it yet again. So Your Suspect will now allow me to express and inform on how I apply the lessons of entrepreneurship to a maturing B2B organization, to the Marketing organization within it, to how I interact with and among, learn from, and inspire the Chairman, the CEO, my colleagues, my peers, vendors, clients, etc. And let me tell you, barely two weeks in, I’m overwhelmed by how much opportunity there is to do just that and so much more.

This was a much longer post than I intended, but one that’s long overdue. As I contribute new content to Your Suspect, I will also revisit some of the themes of previous posts, and revisit my experiences with CitySquares, the events leading up to its sale, the sale itself, and the outcome for me, employees, and investors.

I leave you with that, and welcome your comments. Now, I shovel!

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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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Right Now…

Right now is the most important moment in your business.
Right now is the only chance you’ll have to have right now again.
Right now is the moment you’ll wish you had in a few minutes, a few days, or a few years.

Go thank a staff member for something they deserve a thanks for, right now.
Call that investor you’ve been nervous to talk to, right now.
Ask that board member to hear you out, right now.
Thank your better half for putting up with you, right now.
Call a customer to say hello and offer your help with something, right now.
That thing you’ve been putting off? Yeah, do that, right now.

If you’re an entrepreneur, and you’re not doing something important for your business, for your company, right now, than piss off – because you’re wasting your time, and your wasting everyone else’s time.

I’ve been seeing a lot of tweets, emails, and so forth, lately from “entrepreneurs” who are moaning and groaning, and carrying on. They’re quite vocal about how shitty things are for them, how tough it is out there for them. YOU POOR THING! How can the rest of us help you?

Bullshit. Get off your ass and deal with it, like everyone else. Help yourself, like you need to. Earn it, like everyone should.

Sometimes being an entrepreneur sucks. It’s not a dream job, you’re not an astronaut – even astronauts don’t want to spacewalk sometimes! Sometimes it can be thankless. Sometimes your sacrifices go unnoticed, sometimes your just not happy. But that’s part of being an entrepreneur! You made the decision you sicko! You’re the one who’s been calling yourself an entrepreneur, networking, grooving and moving, shakin’ shit up, makin’ things happen. But now, what? Times are tough, and you’re kickin’ pebbles around like someone just stole your lunch? Bullshit! Get off your ass and get to work! Maybe you need some time off… WRONG. Get to work.

It’s not how you handle the good times, how much fun you had when things were great, how great you looked in that picture for that article, how awesome the feedback was at that demo, or what Arrington said about your business model at a party, it’s what you do when things are hard, when leadership is needed the most, when those around you judge you the harshest, when your product is screwed up, when people aren’t around, when even the local paper forgot who you are.

Right now is the most important moment in your life. If you’re really an entrepreneur, you’ll close your browser right now – or close your email client – and you’ll do something you’ve been putting off right now, you’ll snap out of it and get with the program – right now!

P.S. – That’s Eddie Van Halen – a reference to his song Right Now

Doing What You’re Good At

Seth Godin posted a nice little piece today, as he frequently does, about passion and expertise in whatever you do. Very timely, as I’ve been facing this very question in the past few weeks.

CitySquares has a tribe member who’s been with us for about a year now. She’s a rock star in so many ways. She also really enjoys her job and is proud to work at CitySquares. This is partly what makes her a true member of the tribe.

For the last year she has filled some big shoes, and performed in a job that was not well defined for her. She kicked ass at it, like I never thought possible. And over the course of time she’s naturally filled a role within the company that not only has been a bit of a vacancy within the organization, but is something she’s simply really good at.

No one asked her to do these things, no one pointed her in that direction. Instead, she saw a need in the company, and then filled that need. She’s done so with poise, enthusiasm, with total ease. Today, she was formally moved into that role.

What she did over the course of time, perhaps unknowingly, is what she’s good at, and what she enjoysvoluntarilyon her own. She did so because she has a natural expertise with it, and because she has a passion for it. You just can’t buy that.  The result, and hopefully the result of good observation by management, is a permanent move into that role. This will result in even better performance in this role, it addresses a need within the company, in a happier, more efficient, effective successful company, it results in happier customers and better retention rates, and best of all – a member of the tribe who’s even happier and more successful.