Your Suspect

Entrepreneurs come in different flavors, different sizes, different languages, and different abilities. Some entrepreneurs are brilliant engineers, some are opportunists, some are really good at sales and marketing. One thing is for sure though - not all entrepreneurs are leaders.

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.

CitySquares, Entrepreneurship Entrepreneurship, fred wilson, leadership, seth godin, tribal, tribe

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.

Entrepreneurship, startups balance, Entrepreneurship, health, moderation, stress

Serial Entrepreneur Jason Calacanis who recently retired from blogging and started, instead, an email newsletter has always been straight-talker. His candor and quick tongue are traits I find in myself that often, like Jason, get me into trouble. If you subscribe to Jason’s newsletter you certainly received his latest. If not, you can find it here on Alley Insider.

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.” Read more…

Entrepreneurship, startups depression, economy, Entrepreneurship, failure, fast company, inc magazine, industry standard, jason calacanis, opportunity, panic, perseverance, recession, resilience, seth godin

I believe that if you can see it, you can get there. I was reminded of that notion this morning. I was on my porch early this Sunday morning enjoying the crisp silence of this last day of summer. I looked up and saw a beautiful half moon staring down at me against a sharp blue sky. I stared at it for a moment and remembered how close the moon really is to us, no matter how far away it might seem. But it’s all relative isn’t it? I imagine that during the Apollo missions NASA said the same thing to itself - “We see it. It’s right there. We have the ability, we have the technology. We understand the laws of physics. All we have to do is get there.” And sure enough, one step at a time, they not only got to the moon, they not only orbited the moon, they not only landed on it, they walked on it. Then they drove vehicles on it. Not once, but several times! All it took was some technology, some ability, imagination, innovation, teamwork, and belief in success.

(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. Read more…

Entrepreneurship Entrepreneurship, motivation, psychology

CitySquares isn’t the first startup company I’ve been a part of, but it’s certainly the most special, because it’s my creation. This company has taken on a life of its own. It took some time for it to develop this heartbeat and to get this personality. No doubt it’s is an entity all to itself, more so than just a tax ID with the government. From the very beginning in August 2005, a culture was starting to take shape. We’d sit at my kitchen table in Davis Square and talk about what this could be, how it would work, what kind of future should we plan for, what kind of company do we want this to be. Even when it was just three of us, and even when we had sales people making minimum wage out on the streets all day, every day, it was forming a personality. It was largely out of my control too. I could influence the culture a bit, just by being a part of the business, and setting the vision. But the personality, the culture that the company takes on is essentially a manifestation of the personalities and cultures brought into it by its staff, even those that come and go. Read more…

CitySquares, Entrepreneurship, startups CitySquares, Entrepreneurship, startups

Two of the most important and valuable lessons that I’ve learned over my past 10 years of entrepreneurial experience is the following: work on the business, not in the business, and do the right thing with your business. These simple concepts are actually quite difficult to consistently execute on and as far as I can see, they’re the difference between building a typical business and a great company.

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.

Entrepreneurship e-myth, Entrepreneurship, small giants

Ali and I are moving to a new home in a few days, so naturally our current place a mess. Boxes everywhere, dust bunnies skating across the hardwood floors, the smell of packing tape is in the air, and the sound of tape guns can be heard from one room to the next.

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.)

Entrepreneurship Entrepreneurship, motivation

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.

Entrepreneurship Entrepreneurship, family, motivation

I must apologize - I’ve been neglecting my blog lately, something I promised to myself that I wouldn’t do. This is meant to be an update of sorts, and a promise to you.

So I’m sitting here in my new office, with my window wide open, looking out over the south end. A couple of residents are sitting on their rooftop patios reading, with their dogs sitting patiently next to them. Many thoughts are going through my mind. I’m thinking about my new Board of Directors, about Bob’s presentation that he’s doing soon, about sales, our new employees, about cash flow, about company morale and culture, about my own morale, and how strange it feels to not wake up on the edge of a cliff every morning.

Last night we attended a friend’s graduation party. She just graduated from Harvard and they had a nice BBQ with friends and family, in Teele Square. It was a nice time. I got to talking with her father about business, entrepreneurship and so forth. Turns out he had a big hand in revitalizing the Midwest during the rust belt era. Interesting guy. I told him how ever since we got funded how I’ve felt like I needed to clear my head and press my reset button and how it’s been a bit of a struggle. As someone who, through the government, seeded the entrepreneurial communities of the Midwest in the 70s and 80s, he had some wisdom for me. He reminded me of the importance of taking care of yourself - finding those things in your personal life that make you feel whole and not depending on your business to do that for you. It was an interesting discussion and it really opened my eyes. I continue to work hard, work my butt off, but I can’t help but feel like I’m still not doing enough - like I’m not working hard enough. I’m almost wondering where the pain is. It was almost 2 years that we felt pain and pressure and now that it’s gone, I almost feel like an abused dog that is no longer with an abusive family - confused, disoriented. I’m slowly coming out of it though too, out of the dizzy-spell. I’m starting to zero in on new and fresh priorities. I’m also starting to really enjoy actually running a company, not just a business. That’s probably one of the biggest changes for me - switching gears from running a tiny little business to running a company and having to manage it. Since winding Atomic down, I forgot what it was like to run a company, with employees, and with initiatives and a mission. I pretended, but I also forgot. Now it’s coming back to me. This is fun stuff. But it’s also not what life is about. It’s not the be-all-end-all of life. I must remind myself to take care of myself, to enjoy what I do and to take it seriously, but also to value my time away from the desk, from the laptop, from the BlackBerry. I must remember to sit on my own patio, read a book, hang out and just enjoy - well just enjoy.

Anyway, a bit of a ramble there, but hopefully that gives you a little insight into my lack of blogging lately - it’s been a period of transition and, like a typical guy I suppose, I keep it inside - I don’t express it - I try to work it out on my own (a little Dr. Ruth, or Dr. Phil, or Dr. Melphi for ya). But what I realized the other day was that by not blogging, I’m not staying true to myself or to my personal and professional mission, as it pertains Citysquares. I want to be transparent, honest, candid, and I think I’ve done so historically, but lately I haven’t. So, my apologies to you all.

I hereby promise that I will continue to honor that commitment to you all and to myself. This blog is not just about business, but its about people, about community. It’s about community outside the walls of my office, in the Ethernet and fiber and hard drives of the Internet, and about the community within the walls of Citysquares. This blog is about me, as your host and entrepreneur, and CEO in training. This blog is about grit, determination, honesty, hard work, passion, foolishness, and optimism. It’s about perseverance, guts, openness. I must honor that.

No more blog lag. (Like that? I just made it up. You can use that if you want.)

CitySquares, Entrepreneurship CitySquares, Entrepreneurship, motivation, transition

In my experience as an entrepreneur one of the hardest day-to-day battles is prioritizing. As an entrepreneur who is now fortunate enough to be running a funded company, this has never been more true than right now.

I’ve long been a believer in letting fires burn. By that, what I mean is, having priorities, a short list of priorities, and anything that is outside of that list of priorities is ‘a fire and it needs to burn.’

As CEO of Citysquares, my list of priorities is more strategic than it is tactical. For instance, one of the priorities on my list might be “get this damn sales engine firing on all pistons.” Really - that’s written down on a yellow piece of paper on my desk. That priority is a big priority - and it involves lots of tactics, but that doesnt mean I should get bogged down in the tactics. That’s why I hire people. The employees help with the execution, it’s my job to see it through from start to finish. Anything that is not in-line with that priority, strategically or tactically, is a distraction - a non-priority - and it needs to go on the “back burner” as they say. I don’t care for the “back burner” expression. I prefer, instead, to say that it’s a fire and it needs to burn! But hey - that’s what it is. It’s a little brush fire that needs to burn itself out. If the fire grows to be larger than a brush fire, well than it needs attention and someone needs to put it out.

Now that I have a board of directors to answer to, investors to please, goals to meet, a vision to reach, a real and growing staff to manage, this philosophy is only becoming more and more critical. Since we’ve become funded I’ve found myself doing a lot of operational things - things that just need to get done so everyone can get to work and do so more efficiently than ever before. Most of that stuff is done, and I now find myself taking a little time to regroup - to get even more focused, to assess those priorities and get situated and ready to go. I guess I need that once in a while, time to regroup and assess.

Right now, my priority is to assess my priorities. Anything else is a distraction - a fire, and it needs to burn.

CitySquares, Entrepreneurship Entrepreneurship, motivation, productivity