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.

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!

Related articles

• Are passion and energy requirements for the job? (customerthink.com)
• 5 Things I Wish I Had Figured Out in College (thegloss.com)
• The Passionate Leader (brandimpact.wordpress.com)
• Got Passion? (socialmediaexplorer.com)

The whole idea of The Funded really intrigued me, and had something in common with a little side project of mine called The Founder’s Quandary. But I had no idea who was behind The Funded, so I had no idea who to contact about getting involved or at least offering a virtual high-five.

For it’s first six months it was unknown who “Ted” really was. That is, until Ted unveiled himself as Adeo Ressi, a well known, somewhat controversial, entrepreneur. In the past couple of years Adeo and I have exchanged a number of emails, mostly about how I might help The Funded and perhaps even help with something here in Boston. Well, the good news is that The Funded has announced Founder Institute, and it’s arrived in Boston!

The Funded Founder Institute, a four month program to help founders build the next generation of world-class technology companies, is launching a new semester in Boston from July, 2010, until October, 2010. The program is run by founders for founders, providing a structure for successful entrepreneurs to share their experiences and to provide guidance. Everyone that graduates from the program is invited to join a pool to share in the equity upside generated from the success of their peers. This adds a unique camaraderie to the program and creates a long-term peer support group with a vested interest in your success. If you have a new company or if you are thinking to start a company, take a moment and apply to the program. The program has an early acceptance deadline of May 23rd. Apply here.

If you’re an entrepreneur in Boston I hope you’ll take a look at this opportunity and get involved! I’m just thrilled to see this happen, and I’m eager to see Founder Institute nurture and provide fertile ground for entrepreneurs!

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• The Founder Institute Launches In Boston, Now Incubating Startups In 10 Cities (techcrunch.com)
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• Born in Silicon Valley, Founder Institute Expands to Boston (xconomy.com)

There are countless books on leadership. I’ve read a few, from Jack Welch to Rudy Guiliani, to Seth Godin. In this entrepreneurial age we’re living in, leadership has taken on a new meaning. Leadership is a bit more scientific too, than say entrepreneurship. Yet leadership can also be as enigmatic as entrepreneurship.

I’ve been thinking about these things lately, thinking about the essence of leadership in an entrepreneurial setting.

Fred Wilson, on his blog, said the following the other day:

I’ve heard people say, “If you want to know about a company, all you need to do is look at the leader” and it certainly is true that companies exhibit the traits of their leaders. But it’s also true that companies exhibit the traits of their founders. In fact, I’d argue that founders leave a longer and more indelible imprint on the DNA of companies than the person who is currently running them.

There are a host of reasons for why that is. To start, the business that the company is in is more often than not determined by the founder. And companies can move into different businesses over time, but most stay fairly rooted in the initial business that they started in. It’s also true that the culture of a company is defined early on and it’s hard to change it. Some companies are technology driven, some are product driven, others are marketing driven, and others are sales driven. That most often comes from the founder and it’s hard for a new leader to change that mindset. Another important reason that the founders often have the greatest impact on the DNA of a company is the entire initial management team is most often built by the founder. That initial selection of people is a critical determinant in the way companies evolve and behave and new management will always struggle to change the behaviors a company exhibits.

Founders are entrepreneurs, whether they like it or not. That’s just inherent in founding a company. It’s like giving birth to a child, you are a mother. However, just because you’re a founder, or just because you’re an entrepreneur, doesn’t mean you’re a leader.

I recently read Tribal Leadership, by various others, and Tribes, by Seth Godin. I’m trying to better understand my own style of leadership, the qualities and the characteristics of it. I’m trying to be a better leader, and know where my weaknesses as a leader may lie in order to do so.

What I enjoy most about doing what I do every day here at CitySquares is not closing deals, analyzing Excel workbooks, or conducting board meetings. I don’t particularly enjoy any of those duties and tasks, or many of the countless other responsibilities that come with being the CEO. And none of those things actually make me a leader. What I do enjoy doing is working with the people within CitySquares, as well as the customers and the advisors. I enjoy affecting change, helping the company move forward as a single unit, as a tribe, who actually enjoy their jobs. I enjoy protecting them from the noise outside these walls, and from those who may try to stop them from succeeding. I enjoy achieving our goals, collectively. I enjoy inspiring. I enjoy seeing them smile at our holiday party, as if they’re actually happy to be there because they like the company, they like who they work for, they like who they work with. I enjoy working with my team to find new ways of accomplishing the greater mission of CitySquares. I enjoy inspiring and affecting change then watching them execute, and learn, and get even better at it.

Is this leadership? I don’t know. It’s me, I know that. It’s who I am and it’s what I do best, I think.

I made a mistake this weekend – I forgot about balance and paid the price. Actually, it’s not so much that I forgot about it, rather that I neglected to enforce it for myself and I know now that it’s been happening for a while. If there’s one thing that’s certain about these stressful times, with the economy and, for me, with CitySquares being at such an exciting precipice, it’s more important than ever that we all keep a healthy balance in our daily lives. Everyone is a bit more on edge these days than normal. People are inevitably going to be a little short-fused, or edgy. Myself included.

As an entrepreneur, my work tends to take over everything in my life – literally everything. When I hop out of bed in the morning, it’s game time. In fact, I don’t sleep much, because in between sleep phases I’m still gaming. When I sleep, I often dream of work. When I’m in the shower, I’m thinking about CitySquares. My iPhone is only an arm’s length away, always. Throughout the day I’m full-on. When I get home to see my wife, I’m full-on. When I eat dinner, when I watch TV or a movie, when I’m out and about, my mind is spinning about CitySquares. I may fake it well, but I’m constantly working. It takes a lot to bring me back down. Like, horse tranquilizer strength to bring me down.

Now, this is mostly expected from an entrepreneur and founder of a company – it’s actually normal in the world I live in every day. But as it pertains being a human and living out my life, it’s not normal – it’s harmful. It hurts. It hurts my relationships with others, my mental health, emotional and physical health. It’s literally caused me health problems – some I’m watching closely. In very rare circumstances it can affect others, even hurt them.

This weekend I had an eye-opening and very plainly realized that I’m on a path to self-destruction if I don’t correct this right now. I must get back to balance. I have some hobbies that I’ve neglected lately, some friends and family that I’ve neglected, some passions that I’ve ignored. Maybe I need a long weekend away on a beach somewhere. I’m not sure, but I’m going to figure it out fast.

As with everything in life, there must be moderation. And that goes for entrepreneurs too! In this fast-paced, web 2.0, always-connected, get-ahead entrepreneurial way of life it’s so easy to get lost in it all.

I believe it was Buddha who said, “everything in moderation, even moderation.”

‘Nuff said.

Jason’s email has a “focus on the entrepreneurial and startup depression and economic downturns/depressions–and how you can deal with them.” He suggests that the economic downturns we’re seeing right now will kill 50-80% of startups within the next 18 months, and that entrepreneurs need to be prepared to take certain steps to fortify, but also to monitor and address their own “entrepreneurial depression and anxiety.”

I love this topic. I’ve stated many times on this blog, and otherwise, that one of the biggest defining characteristics of an entrepreneur is his/her perseverence and resiliency. Those characteristics are to an entrepreneur like water to a fish. These are traits that an entrepreneur just requires 100% of the time. Jason states,

“Depending on your DNA, getting your ass kicked is either complete torture or deviantly rewarding. Truth be told, I like getting my ass kicked because it makes me angry, motivated and focused.”

That’s just worded perfectly. You either got it or you don’t folks! I know, for myself, I work best when the chips are down. When I’m in second place, I move into first. When I’m behind in the count, I hit a double. I’ve always been like that. I think most entrepreneurs are wired the same way.

Jason makes some very specific recommendations about things you can do right now to cover your ass. Some of those recommendations are as follows:

1. Execute better: This is fairly simple, as I describe above. Rank
yourself and your performance and improve it.

2. Grow the talent you have: When the market is down, it’s a great
time to get your team educated and to the next level. Invest in
training and education of your top people, because they are the ones
who will lead your company through this mess.

3. Firing the average people: Again, it’s totally politically
incorrect, but I highly recommend firing anyone who is good or
average. Startups are an Olympic sport and every slot on your team is
critical. You wouldn’t put a “good” swimmer in a relay, would you?
Don’t have one in your startup. Fire the good and replace them with
the great.

4. Cut spending every where you can: Recurring costs like
connectivity, phones, rent and insurance are things that you can
easily cut. Go to each of your providers and ask for 20% relief
immediately or you’re leaving. Most, not all, will give it to you.

5. Find a revenue stream and ride it: If you don’t have a revenue
stream right now, you’d better find one on Monday. Seriously, by the
end of the day. Once you find this revenue stream, ride it. Put at
least 25% of your effort into bringing in revenue.

6. Focus on your profitable clients: If you have revenue, start
focusing on which clients are most profitable. Take them to lunch and
figure out how you can over-service them and sell them another product
(or more of your current product). You’re gonna want to protect these
accounts because the folks reading Point Five are going to be calling
them!

7. Make your top ten 10% better: Look at the top ten aspects of your
business and come up with a plan to make each 10% better in the next
30 days. Ask everyone in your company to make suggestions for the 10%
better program and execute on the ones that will provide the most bang
for the buck. Sometimes, there are things you can do today that will
make something 10% better for free–you just haven’t brainstormed
enough.

8. Hold an optional off-site breakfast meeting on a Sunday and see who
shows up: If folks don’t show up for you to grow/save the company on a
Sunday for a two hour breakfast, they probably aren’t going to step up
when the sh#$%t really hits the fan. You need to know who the real
killers on your team are and you need to get close with them now.
Again, it’s fine to have 9-5ers on your team–if you’re the Post
Office. You can’t have them at a startup company. Note: if you reading
this and saying I’m anti-family, save it. Folks don’t have to work at
startups and some of the hardest working folks I’ve met have families
and figure out how to balance things.

9. Build marketshare: One of the best things to do in the down market
is build marketshare. Look for competitors that are going out of
business and buy them or just “steal” their clients and talent (i.e.
pick them up).

10. Raise money: I know I said above most folks won’t be able to raise
money in the down market, but that’s not because the money isn’t out
there–clearly it is. The issue is that the big money out there
doesn’t want to fund small ideas that are in the death spiral. Build a
plan based on revenue and taking market share and folks will consider
funding you.

I think it’s also worth noting entrepreneur and author Seth Godin‘s statements in a recent blog entry:

“Inc. magazine reports that a huge percentage of companies in this year’s Inc. 500 were founded within months of 9/11. Talk about uncertain times.

But uncertain times, frozen liquidity, political change and poor astrological forecasts (not to mention chicken entrails) all lead to less competition, more available talent and a do-or-die attitude that causes real change to happen.

If I wasn’t already running my own business, today is the day I’d start one.”

I wholly agree with this and it seems others do too. Many contend that the best time to start a business is now, during a recession.

Inc Magazine has a nice piece from May that tells the story about a select few businesses who started during a downturn, and prospered too. Fast Company readers respond to this article.

The Industry Standard gives Five reasons why a recession is a good time to start a company.

With Congress on the verge of approving some sort of bail-out for this financial nightmare, it’s important that people keep their heads on straight and stay focused. Perhaps this is an overly simplistic analogy, but it’s sort of like when the power goes out during a winter storm. You don’t know when the power will come back on, you feel the temperature in your house dropping, the pipes might start to freeze, and your children, your pets, and everything starts to be affected. But that doesn’t mean you light a fire in your house either. You don’t start burning the furniture. You stay calm, you buckle in. You get prepared to ride it out by finding sweaters and doubling up on socks. You fill up jugs of water, you let the ice melt, you light a few candles, but not all of them, you play a board game, keep your spirits high, and take it slow. But you also have a plan.

Now is the time to fortify and strengthen, get better, get mean! Those who panic aren’t thinking and don’t have a plan. So think – have a plan. Have a plan B. But most importantly, stop for minute – recognize the opportunity that’s in front of you! These opportunities don’t come around too often.

(Wow I just made the Apollo missions sound really simple didn’t I?)

I was raised to believe that anything was possible. Both of my parents are good like that. No matter what crazy idea I had, they supported me, as long as it wasn’t harmful, but they didn’t indulge me too much either. When I wanted to be a fighter pilot, they supported me. I’d study the G force and read about Chuck Yeager. When I wanted to be a major league pitcher, my father taught me proper form and challenged me during little league practice. I could go on. The point is, I tried, and I worked at it very hard. No matter how far off the destination seemed, I believed in myself and I had the support of my parents. I may not have been capable of being a fighter pilot, because of my poor eyesight, but that didn’t matter – anything was possible. My fastball was pretty nasty, but that was all I had. Yet I had the potential.

Entrepreneurship is very much the same way. You have to believe in yourself to a point that others may even laugh at you, think you’re ridiculous, out of your mind even. But hopefully, if you’re fortunate enough, you have people around you who also believe in you. I have my wife and my parents.

My sister, Jodi, put herself through school at William and Mary University in the early-mid 90s. She studied psychology at W&M, and studied a bit about entrepreneurial psychology. We got to talking the other night about entrepreneurship, and what drives an entrepreneur. It was a fascinating conversation, one that, once again, I found myself talking about objectivism and existentialism and ‘the bigger picture’. One thing she kept trying to drive home with me was that something else is driving me. My philosophies may be a nice justification or rationalization of my efforts because I happen to be an entrepreneur, but there’s something else driving me. We struggled to figure it out but we were able to arrive at this conclusion, at least temporarily: I believe that anything is possible. Nothing is in my way. I have nothing to risk and everything to gain. One way of explaining this is my perspective on bad luck. When shitty things happen to me, I don’t say “hey, things can only get better from here.” Actually, what I say is “hey, things can get a lot worse from here.” I never really analyzed this until this conversation with Jodi. One attitude indicates a passive attitude, one that says “its OK, things will work out for me and I’ll be happy.” The other attitude indicates an active attitude that says “shit, this isn’t good, and it could get worse, let’s get going!” There’s a huge difference in attitude. And I don’t think that’s an attitude that can be learned. That is, perhaps, my best definition of an entrepreneur.

I meet other entrepreneurs all the time, naturally, but I find myself associating best with entrepreneurs who have that same energy. There’s a sort of pie-eyed optimism that we share, an almost ignorance that we carry around with us that masks our refusal to quit, our denial of failure. I could name a few of these entrepreneurs, and perhaps I will another time. I could also name other entrepreneurs who seem to have what it takes, but behind the skill, the technical know-how, there’s something lacking – that spirit, that pie-eyed optimism, that ignorance.

Another thing that I was taught as a kid, by both of my parents, was that all you have to do is envision the goal, see it happening, and you can get there. I can hear my father now, “See the ball go into the catcher’s mitt” and “see the ball go in the basket” and “see yourself getting into the Air Force Academy.” I still use that visualization technique today. I might be golfing, and I’ll see the ball soar through the air and land, well, not in a bush! I’ll see CitySquares getting to the next milestone, a milestone towards the ultimate goal, which I also can see. I can still see the moon too, from my window next to this table. I believe I can get there, because I can see myself there.

Startup companies are families. If you’re part of a startup, you know what I mean. If you’re not, ask someone, and join a startup. It’s special. There are some people who were with CitySquares for only a few months, going back to 2005, some I think of very fondly, others not so much. Those people, no matter how short or long a period of time they were with the CitySquares, influenced its personality, shaped its culture, impacted today’s family members. Once the company received financing it was inevitable that the culture was going to change, and perhaps a bit radically, and quickly. Sure enough, it did, but again, in positive ways. I’ve always kept company culture in our sights, ensuring that CitySquares was a place that people wanted to be, enjoyed coming in. There’s simply nothing worse than not looking forward to going to work because of its people, or because of its culture, or because you don’t fit in. That was unacceptable to me from the beginning. Good attitudes have been, and still are, essential to being here. As our job descriptions always indicate, guts and passion are requirements. If you don’t got the guts to jump into the deep end, in the shallow end you’ll stay, forever. If you don’t have a passion for what you do, or for CitySquares, stay home.

We’ve also always had a diverse group of people working for us. White, black, Hispanic, man, woman, gay, lesbian, it doesn’t matter. Can you do the job? Do you have something to offer this company? Will you add some new flavor to the dish, in a good way? Will you last? Do you have goals? Passions? Do you have a life outside of work? That’s what we have today, a diverse, fun, whip-smart, ambitious, and real people at CitySquares. They’re my family, and I’m theirs. We see each other more than we see our own families, spouses, children!

The hardest part, however, is having to see one of these brothers and sisters leave us, whether on their own accord, which hasn’t happened much, or because we ask them to leave, which happens more often than I can stomach (once is enough). There’s nothing harder, nothing more difficulty for me and for the others, than to see someone leave. To have to clean up their desk, forward their email, redirect their phone calls, pick up where they left off, sucks. It totally sucks. There’s something almost macabre about it. I have a certain affection for everyone here at CitySquares. I have an affection for most of those who’ve left the company, on good terms anyway. I’m still in touch with many of them. I think we all have that affection.

There are the good times, and there are the bad times, especially in a startup company. Change is inevitable. It’s not predictable either. Can everyone adapt? Can everyone accept the changes? Everyone has to have a certain amount of faith in a startup. If someone doesn’t buy-in, it can jeopardize momentum. If someone’s not performing as needed, the tolerance is low. We’re only as strong as our weakest link. No matter how much it hurts, change can come at will, or it can be forced. It’s our choice. I’d rather choose my own change than have it forced on me.

The best is yet to come, and I keep reminding myself how so many others here at CitySquares have never been a part of the next phase of a startup, the growth phase. I have fond memories of my days at Delphi and Prospero, when the company ballooned from 12 employees in a crappy office on Mass Ave in Cambridge, to a much larger, sunnier, more vibrant place in Kendall Square. I remember the growth, the excitement, the thrill in the air. Everyday was so exciting! CitySquares is close to that feeling. My family is about to experience such excitement, thrill, anticipation, and that makes it all worth the heartache and pain.

At my previous company I frequently found myself dealing with A/P and A/R, collections, or dealing with technical challenges, project management, sub/contractor matters, and more. At the time I would have told you that I didn’t have a choice because “someone’s gotta do it and if it’s gonna get done right, it better be me.” Something else I found myself doing quite a bit of, which I greatly enjoyed, was working closely with customers. And it’s interesting how this concept of “working on the business, not in the business” can be somewhat confusing. To some, working with customers might be considered working in the business, and it can be, if the context is perhaps more operational and tactical than strategic. At CitySquares I frequently interact with customers. In fact, I have my own accounts that only I handle. These are my projects, if you will. I experiment with them and use them as case studies to learn more about their needs and keep my finger on the pulse of the local market. I also interact closely with community organizations like Somerville Local First, among others. This kind of finger-on-the-pulse approach is very much about working on the business.

Along my way over the last few years I discovered two books that made the biggest difference in my professional life. The first is called the “The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It” by Michael Gerber. It’s written well but with over-the-top case-and-point scenarios, but it definitely hammers the point home. This book was a sort of kick in the ass for me and it helped me, as Mr. Gerber might say, “stop baking pies and start building a pie company.” It’s essentially about the mindset of the founder (technician vs. manager vs. entrepreneur). And it was the E-Myth that helped me start CitySquares with the correct mindset, and I’m constantly reminding myself of this and working to improve upon it. The second book is called “Small Giants – Companies That Choose to Be Great Instead of Big“ by Bo Burlingham. This book helped me see a bigger picture, one about being more than a business, one about being a responsible company, a company that gives a shit, that does the right thing by it’s customers, by it’s employees, by it’s community. It’s also about socially responsible business and that’s something that’s baked into the DNA at CitySquares. I highly recommend both of these books to any entrepreneur out there.

I guess my point here is that while some may tell you to “work more on the business and work less in the business” it’s a lot harder than it sounds. One can’t just wake up one day, 5 years into the business, and make her business grow, or change its culture, or its mission. It’s just doesn’t work like that. What she has is baked into the company’s DNA from day 1 and, in my opinion, it’s very difficult to change (although it can be done). If you’re an entrepreneur, or on your way to becoming one, make sure you understand these concepts, make sure you really get it and if you have any doubts about this be sure to pick up the E-Myth and Small Giants.

Finally be sure to buy these books at an independent bookstore! If you’re in the Boston area you can find a locally owned and independent bookstore at CitySquares.com. Really, get off your butt and visit one. Trust me, Amazon will survive.

I was packing up a room this morning, and I came across an old boombox. I noticed there was a CD in it. It happened to be Neil Young’s Harvest Moon, a slow, acoustic, melancholy album. Among the songs that came on was “One of These Days.” It really took me back – I mean way back. The last time I heard this song was probably in the mid 90s, on a snowy day just like today, with an old friend. A friend I miss dearly. There are many friends who I miss dearly. It’s ironic that the last time I heard it was with an old friend who I miss dearly. Among the lyrics of the song:

“One of these days, I’m gonna sit down and write a long letter, to all the good friends I’ve known…

I never tried to burn any bridges. Though I know I let some good things go…

From down in L.A., all the way to Nashville,
From New York City, to my Canadian prairie home,
All my friends are scattered like leaves from an old maple.
Some are weak, some are strong.

One of these days, I’m gonna sit down and write a long letter to all the good friends I’ve known, and it won’t be long.

Songs mean a lot of things to each of us, and to many there is nothing more powerful than a heartfelt song. Today I had one of those moments.I was reminded of so much – so much that I’ve tried to forget, so much that I’ve tried to move on from. And for the most part I have, but much of it’s still with me, mostly good stuff. I guess as life goes on, so much sticks to you, other things don’t. And we don’t get to pick and choose. All we can do is make decisions about right now. Those decisions influence those we’ll be faced with tomorrow.

I guess what inspired me to sit down and write this in the middle of packing is that it really reminded of what I’m working so hard for. I’m working for a better life – for myself, for my wife, for a family that I’ll build. I’m working to make sure that I’m the best person I can be. To live right. I didn’t set out to be an entrepreneur. I didn’t get a degree in business. It’s not intentional, this entrepreneurial thing. And It’s not about the money, it’s not about having a notch on my belt, it’s not about being an entrepreneur, or being connected to wealthy and powerful people, or an ego. It’s about building the best life I know how to build.

I’m glad I put that CD on today, I’m glad the song came on, I’m glad I remembered.

(Sorry for the cheesiness.)