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!

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As some of you likely know, it was announced in early December that CitySquares was sold to Backyard, a west coast based startup with funding from Google CEO Eric Schmidt, celebrity entrepreneur and investor Jason Calacanis, and self described greedy, blood-sucking venture capitalist Dave McClure. It’s not the investors that make Backyard exciting, to me anyway (although it certainly has a nice ring to it), it’s the founder and CEO Steve Espinosa. I’ve known Steve for a few years now, and at 22 he’s already a very well admired veteran of the Local space and I’d bet on him any day of the week. So it’s an honor to have sold CitySquares to such a great guy with an equally great vision.

Now that CitySquares is largely behind me (I will still be involved as an advisor), I’m moving on from Local. Plainly put, 2010 kicked my ass, and CitySquares’ prospects for regaining its edge wasn’t getting any brighter as this year passed for reasons I won’t get into right now (but I will once the dust settles). As Greg Sterling penned on his site announcing the acquisition of CitySquares,

Given the noise and competition now in local Saren is not unahppy about exiting the segment for now…When CitySquares launched, for example, there was no Google Places, no Facebook Deals, no Groupon and no Foursquare (et al).

There’s a whole lot of truth in those two sentences. More truth than you know. I can proudly say that CitySquares pioneered hyper-local search. No one was doing local search at the neighborhood level until CitySquares came along – and I mean really doing it at the neighborhood level. And to this day, I will boldly state that still, no one has the mashup of hyper-local geospatial data and local business listings that CitySquares.com has. Alas, the mobile platform is the future of local search, of hyper-local search. OK, it’s not the future, it’s the now! So of the many things I can hang my hat on as I close the door on my CitySquares.com chapter, this is one of them.

Another thing I can hang my hat on are my relationships with countless people, of so many background, cultures, and talents. I’m proud to call many entrepreneurs, investors, employees, associates, vendors, partners, across the country and in many corners of the globe colleagues, acquaintances, even friends. CitySquares took me places I never imagined going, both literally and figuratively. I’m most proud of this.

So it’s with both excitement and with sadness that I say goodbye to 2010, and with open arms that I welcome 2011. I will be making an announcement about my next step within the next week or two. In short, it’s a big change for me, and a change I’m thrilled about.

Before I sign off for the year, I’d like to wish you a very healthy, happy, prosperous 2011. See you on the other side!

Au revoir

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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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Is the Democrat from Connecticut out of his mind? What is he trying to achieve here, raising revenues for the federal government? I don’t get it – where’s the logic in this provision? Maybe someone smarter than me can help me understand, but in the meantime if you are for entrepreneurship, for innovation, for job creation, for small business, then go here and sign the petition to stop this nonsense.

More information can be found here on The Huffington Post, in a well penned piece from Robert Litan. A quote follows:

Various studies published or sponsored by the Kauffman Foundation have made it abundantly clear how dependent the U.S. economy has been and will continue to be on the formation and growth of new companies. Angel investors are important funders of new companies. There is no good time to make it more difficult for them to invest in startups, and now — when the economy is struggling to recover from what may be the deepest recession since the Great Depression — is the very worst possible time to discourage angel investment.

Sign the petition here.

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My colleague, Todd, and I had back-to-back-to-back meetings from even before the preconference started on Monday morning. By the time I left the hotel late Wednesday night, it wasn’t without three more impromptu meetings that kept me busy and well fed right up until I had to leave for the airport at 7pm. Here I am, 1:30 the next day, 60 minutes away from a follow-up meeting.

I wonder sometimes how some businesses in my industry (vertical? space?) are even able to stick around or grow without attending shows like these. These shows are sort of like annual or biannual checkpoints for many companies; are you still in it? are you thriving? surviving? ready to grow? growing? ready to do that deal you put-off last time around? changing models?

Since I started attending these shows almost five years ago now, I’ve seen many companies come and go. It’s exciting to grow alongside other companies, competitive or complementary or otherwise – it really is something to have those brothers and sisters to grow up with. It’s also sad and disheartening to see some of them vanish, never to be heard of again – to reminisce with others about those brands, faces, names, stories.

Perhaps the one point that really stands out for me though is how clear it is to me that these kinds of conferences and trade shows are so vital for me as an entrepreneur, and for CitySquares as a business. Some thoughts I’d like to share while they’re still fresh:

1. Never judge a book by its cover. It’s so easy to dismiss a company because their slides may have seemed boring, or overly complicated, or the speaker wasn’t charismatic enough, or was even too charming. It’s easy to dismiss a company because their booth wasn’t fancy enough, or because someone was shy or anxious and didn’t have a drink at the mixer. I’ve been surprised so many times. Be bold, be brave – talk to everyone – but don’t be too aggressive about it. Just be there. Being there is the first step. Before you know it you’re deeply engrossed in a conversation and discovering common denominators.
2. Don’t go to bed. I mean this. You didn’t spend your or your company’s money to go to bed when the best stuff happens. The best time to meet people, to learn, and to establish relationships and prospect for deals is during the hours following each day’s show. Whether in the bar, the restaurant, in the lobby, in the hallways, or outside the hotel at dinner and bar meetings – that’s when it happens. Simply put, be available. Don’t drink? No problem – but be there. You can make up the sleep on the plane or when you get back to your hometown. This way you’ll really be taking advantage of all the networking opportunities.
3. Be real, be curious, be yourself. Don’t know about a topic being discussed, ask the panelists questions when the mic goes around. If the mic doesn’t make its way to you, stick around after the panel and track down the people you want to talk with. They’re at the show for the same reasons you are!
4. Have business cards. I know it’s a no-brainer, but there is nothing worse then meeting someone and not getting their business card, or vice versa. Bring three times as many business cards as you think you’ll need. I can assure you that if you’re doing all of the above, you’ll use them. You may even need to run up to your hotel room to get more cards.
5. Ask for time. If you meet someone you’d like to get to know better, or learn more about their business or talk about some ideas you have for working together, just ask them to meet with you. This is so easy – whether its an early breakfast meeting the following day, a chat in the hallway at a table, outside in the sun, at the bar that evening, over lunch or dinner, or even out in town – just ask them for their time. You’d be surprised. I’ve never been turned down. Sometimes you meet with someone and you find there’s just not a fit. OK – now you know! Time wasted? Absolutely not! More often than not though, there’s a synergy somewhere – but don’t force it either.
6. Follow up. LinkedIn is the best way to follow-up. If you’re not on LinkedIn – get with the program! Really though. When you gather up all those cards every day, before you finally close your laptop at the end of the night, set them down, search LinkedIn for each person and write a personal message to them – remind them who you are and add some context to the message. A lot of names and faces get mixed up, business cards are just the reminder. Mention the topic you were discussing, be it business or even something casual that was discussed. It’s hard to remember who everyone is, but when you add context it jogs the memory and make it a lot easier for the recipient to accept your request. Follow up again a few days later with an email or a phone call.
7. Go to the sponsored parties and events. Most evenings after the day’s events, there are company sponsored parties and gatherings. Go to them! If you find out its exclusive, and invitation only, just find out who’s doing the inviting and ask if you can attend – its rare that you’ll get turned down. Again, that’s what these events are for and the more people that show up, the better off that company looks – they want a good turnout! They want to be sold out and want people talking about it.
8. Relax. This is especially important because no one wants to talk business 100% of the time. Be yourself, talk about where you’re from, learn about where others are from, talk sports, schools, family, hobbies. You’d be surprised when you do – often times you’ll find that you have a lot in common, and what was at first perhaps an awkward introduction turns into laughter, common interests or connections.
9. Keep it simple. You’re wearing a name tag. People will look at it. After shaking someone’s hand and introductions the first question will be “so what does [your company name] do?” Don’t go into a 10-minute monologue about your special patent-pending technology that’s going to change the game and disrupt the whole business. First, no one likes to hear that their business is threatened by yours, and two, no one likes a bore. Be able to explain in less than 3-4 sentences what you’re business does – specifically what problem it’s working to solve. But don’t be secretive either. No one likes a spy or stealth company being sly.
10. Know the right people. This is huge. Get to know a few people who run the conference, or who seem to know the right people, the folks at the booths, and others. If you see someone talking to someone you’d like to speak with, just ask for an introduction! They’ll be flattered you asked them. Knowing the right people does not mean shadowing people, tagging alongside them like a pet dog though either.

I hope these 10 points ring true for you, or inspire you to get out there more. And if you have any tips you’d like to add to this list, I’d love to hear from you, as would my readers.

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I’m reminded of this word, this strong and intimidating word, by watching American Idol tonight. I know, cheesy, but as an entrepreneur often does, I tend to put lots of everyday observations into the context of entrepreneurship so bear with me. One of the contestants on tonight’s episode was pleading and begging with the judges (Simon, Randy, Kara, and guest judge Ellen Degeneres). The judges were resolute in their decision, there was no chance in hell she was going to beg a “yes” from them, yet she continued until it got a bit pathetic. Ellen was quite clear and concise in the way she explained to the contestant that this “no” was not the end of her life, nor was it the last “no” she’ll ever hear, rather this moment is something that she’ll look back on as just another “no” that made her stronger. That kind of wisdom, that Ellen applied, is only gained after overcoming the word “no” and having something to really show for it. Most successful people, no matter what kind of success they’ve had – be it artistic success, professional success, financial success, success through freedom – have overcome this word and made it an opportunity, not an obstacle.

I’m reminded of how many times I heard the word “no” as a teenager when asking a girl out (I did hear “yes” from time to time!). I’m reminded of how many times I heard the word “no” when I didn’t make the team, when job hunting, when selling something, or when pitching venture capitalists.

The word “no” is rarely the end of the road, more often it’s an opportunity. Hearing the word “no” automatically prompts a follow-up question that you can hear from children more often than adults, and it’s “but why not?” or “how come?” That question, that follow-up to the “no”, is the opportunity to learn more, to understand why you aren’t getting what you want.

That’s what “no” is – an opportunity to learn, to improve, to achieve wisdom. Next time you may still get a “no” but perhaps a little later in the conversation.

Being able to overcome the word “no” is a defining characteristic for optimists or idealists. On the flip-side, not being able to overcome this word is a often a defining characteristic of the unambitious, or of pessimists.

Being able to deal with this word is also a defining characteristic for entrepreneurs. I’ve heard this word the first time I hit the streets to sell a CitySquares product, and I learned from it. I bettered the product, or the pitch, and heard it again, and again, until finally I heard Yes once, then twice, then again. I heard the word “no” when raising money for CitySquares, when we weren’t ready. I heard it when I thought we were ready and thought the prospective investors were crazy or foolish. I heard it when I tried to close our first really big sale, or when I tried to establish a big partnership. Yet never has “no” been finite for me.

The word “yes” is an exciting word, it means you got something right, or got what you wanted but the word “no” can oftentimes be more valuable.

• As soon as the hard times hit I saw an immediate response by the staff at CitySquares. For the most part, the team held together and today we’re tighter and stronger for it. Like a tribe, we stuck together and hunkered down while battles and storms happened all around us. We were not well fortified but we survived and now we’re about to thrive! On the other side of the coin, a couple of our tribesmen demonstrated an inability to persevere and overcome these challenges, and some weaknesses were exposed and ultimately eliminated. Thankfully that ended rather quickly and the tribe was/is better for it.
• Small businesses, specifically brick and mortars and mom-and-pops, got their asses kicked much like we did. Those who hadn’t yet learned to fly unfortunately fell from the nest and met their demise in ways that were hard to watch. Balances went unpaid, phones disconnected, and personal stories of financial tragedy were common. It was truly heartbreaking to see. Yet many also survived and are resurfacing with tougher skins and stronger businesses!
• Beyond the staff at CitySquares I also experienced something completely new and foreign to me – board members and shareholders reacting in different ways. The vast majority of them demonstrated a wisdom and calmness that really impressed me and taught me a whole lot about pragmatism and experience. That, however, was not always the case. In a couple of isolated incidents I witnessed naked panic, fear, and fright and this came from the worst places possible in the corporate structure. I will not divulge the details not for lack of transparency but for reasons of respect and professionalism – that is a fine balance you know! As a result of these panicked and frightened reactions it was apparent to me that something had to change and change immediately or the company was destined to collapse for unacceptable reasons. It’s one thing to fail because a business model fails, or because of timing or market and/or economic reasons, but its another to fail because of human emotions, poor judgement, and failure to communicate and work as a team. At the end of the day, however, our shareholders demonstrated their commitments to the company but continuing to support us financially and through other supportive means. Again, we are now better for it!
• As a leader I learned so many lessons in the past 12+ months, but two in particular that I will not ever forget. For the sake of brevity there were a few incidents in the first half of 2009 when I lost control of my emotions and let anger and fear win. These incidents are not something I care to revisit in detail and am embarrassed to detail. I have made amends in both instances. These two cases taught me some huge lessons, lessons that took me months to truly understand and apply to life and work.
• In a tribal organization like ours, loyalty, communication, and teamwork are absolutely vital. What became incredibly apparent to me was how strong the tribe is when communication is at its best, when leadership is performing in the right ways, and when the tribesmen are truly committed to each other and to the tribe’s visions and beliefs. There is something almost dogmatic about a small company! I saw people step up to the plate in the most amazing ways. It’s still happening today. People are not willing to settle for less, nor willing to sit back and be OK with the way things are or may be heading, they expect more from themselves, from the others, and from the tribe as a whole. There is much of this happening right now, as it should always be! A sort of shuffling is happening internally, and its happening in a way that is uniting the tribe only more and making the company better and more focused and determined than ever before.

These points are the major ones that stand out for me, as an entrepreneur and as the chief of the tribe. There’s lots of business related stuff too, like how we got through the last 15 months, and what changes we made to our business/model/execution, etc. And those things are continuing to happen, but the reality is this: CitySquares is stronger, more successful, and closer to our goals than ever before! Its because of the above points, among lots of others, that we are here today.

A few of my entrepreneurial goals for 2010 are as follows, and I will soon be blogging about these things:

1. Continue to grow and mature as an entrepreneur, as a CEO, and a tribal chief. How? Continue to identify and improve those leadership traits where I am weakest, and harness and cultivate those where I am strongest. I cannot do this alone either, I need my tribe to help me, I need to read and learn more, talk less, say more, listen more.
2. Blog here more often, with transparency, and with purpose.
3. Create and participate more in entrepreneurial circles, networks, and communities (e.g., The Founder’s Quandary)

I am still working on these ideas and a couple others. I will be blogging again here very shortly. Stay tuned for more!

2010 is going to be an extremely good year for CitySquares. No doubt we still have lots of lessons to learn and battles to fight, that’s par for the course. But if we can survive and unite the way we did in 2009, than 2010 is really going to be something else!

Happy new year to you all, may your 2010 be filled with new found freedom, with health, and prosperity.

When I look back at the entrepreneur I was four years ago and compare that guy to the entrepreneur I am today, I see two very different people. The entrepreneur in 2005 was much more naive and immature. I was so much more of an idealist, so much more pie-eyed, and I had a sharp tongue and quick trigger-finger that I had a hard time controlling. I’m still an idealist, I’m still pie-eyed, and I’m still naive and probably still a bit immature, but today I’m much more rooted, more grounded, more focused, and much more thoughtful about how I communicate and how I handle stress. That’s been a real battle for me – balancing life, making sure that my work does not define me, and hence dominate me.

So much has changed in the local search arena too. When we started many of the players we hear about today were as small as we were. Citysearch was really the only major player. We hardly knew what we were stepping into and local search is a more crowded and competitive space than I ever anticipated, and rightfully so, the market opportunity is massive. That kind of competitive environment has only kept our edges sharp and kept our eyes keenly focused.

The business itself has matured in many ways yet the model itself is still largely intact. That’s a real testament to the market opportunity and do our original business model. While the economy has presented a number of substantial challenges, we’ve been able to navigate our way through the choppy waters and in some ways its actually helped us sharpen our tools. It took us a few years to understand a number of the most fundamental parts of our business model and test them, and now, through some amazing partnerships and alliances we’re about to unleash some powerful solutions to a core problem in the marketplace.

Some of our identity changed over the past four years too. Unfortunately, as a small business with limited resources, there are only so many things we can accomplish. Our heart is big here at CitySquares, and we want to do so many things, want to give and contribute so much to society. If we were a non-profit, we could focus all of our time on these things, but we’re not – we’re a business. We’re in business for a reason, to tackle the market, solve a problem, deliver value for our customers, and along the way make money and provide a return for our investors. It’s not complicated, but realizing that took some time. I look forward to returning to those ideals at some point, be it through CitySquares or other channels.

My partnership with Bob has grown so much, and it’s just been awesome to watch him grow as a professional in parallel to my growth. Bob has stepped up, challenged himself, and done so through some very difficult circumstances. Not only has my partnership with Bob grown and blossomed into a very solid and loyal one, but our friendship has strengthened immensely. We may not hang out as much as we both would like but we don’t need to. I see Bob more than I see my own wife, and our friendship is evident to those who work with us and evident in our ability to work together through thick and thin.

I’ve also had the pleasure of seeing my colleagues grow as people, as life inevitably happens, and see them grow as professionals. Start-up life is not for everyone! That’s a fact! People who I work alongside, like Justin, Kim, Michael, Amber have proven themselves not just as contributors to the business and the company, but as loyal companions who continue to illustrate every day what tenacity and perseverance is about. They are the embodiment of these characteristics. They’ve also become friends and I’m so proud of them, and I’m excited to work with them in the months and years to come, and be able to provide for them and support them as they grow.

I’d like to point out some of the folks who’ve joined the team, stuck it out, and supported us in any number of ways. These people are not all necessarily employees, they’re friends to CitySquares too and their contributions to the company and the business have just been awesome. These folks continue to support us. The list is long, they know who they are. I’m not sure that this anniversary merits thanking them publicly, not quite yet – that day will come, I’m sure of it.

Along the way over the past four years we’ve made friends in the business too, with competitors, industry experts, vendors, service providers, consultants, press and media, and fellow startups and entrepreneurs. They’ve all added to the fun and the experience of CitySquares. Along the way we’ve also seen companies fail to succeed, entrepreneurs see their dreams crushed, and see the underbelly of entrepreneurship, startup life, and even see unethical behaviors by people and companies. These things have all taught us, made us stronger, and made us wiser. No different than a person going through life – learning lessons and becoming wiser in the process.

We’ve made mistakes, of course. I’ve made mistakes, no doubt. But today, on our 4th anniversary I can proudly admit that we’re doing something right. It takes a team to make that happen. No one person is responsible – everyone and everything listed above, and more, is just one of the puzzle.

So while an anniversary such as today’s is special, its just a milestone. There’s still so much work to be done. We can celebrate briefly, but the work continues. Every day is another day in the trenches and we need to advance our lines.

Onward and upward we climb, into our fifth year, heads held high, humbled, courageous, wiser, and focused more than ever.

Thank you for reading.