Adios 2010

Adios 2010, sayonara, salaam, lehit, au revoir, ciao. There aren’t enough ways to say goodbye to 2010. It was a tough year for America, and for much of the world. Speaking for myself, professionally, 2010 was a year I’ll never forget. Truth be told, I’ve been thinking about this blog post for some time now. I’ve fantasized about addressing the entrepreneurial challenges I faced in 2010, facing of a severely depressed economy, an increasingly crowded local search segment, a handful of souring investor relationships, among other disappointments. But I’ve changed my mind. I’m going to spare you, my reader, from my bitching and from some opportunistic ‘lessons learned’ and drop my weapon so as to not injure anyone. Instead, I’ll end this year’s blogging, this decade’s blogging, by closing the chapter on a decade and an era I’m most grateful for.

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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Speaking at Marketplaces 2010

The Kelsey Group is like the ESPN of the local search and advertising world. They’re the authority. They host about four major conferences every year, attracting industry insiders from around the globe. Their next one is next week in San Diego, called MARKETPLACES 2010: THE LOCAL VERTICAL OPPORTUNITY. It’s the who’s-who and that what’s-what of local and vertical solutions and advertising. I’ve attended numerous Kelsey shows and have come to know the Kelsey staff as warm and generous professionals, and many of the conference regulars. The Kelsey Group and their conferences have been absolutely critical for CitySquares. If it wasn’t for them and their shows, I don’t think we’d be a player on this big and competitive field.

I was asked to speak at the Marketplaces show alongside Colin Pape with ShopCity and David Vazdauskas of Local Thunder. The panel will be moderated by Steve Marshall, who I always enjoy. He doesnt pull punches and he adds a certain kind of intensity to the panels. I’m looking forward to it.

I’ll be at the show from Sunday through Wednesday with my colleague and VP National Sales Todd Salerno. We have a few meetings teed up but if you’d like to catch up with one of us just email me, tweet me or send smoke signals, whatever works for ya!

If anyone wants to go, but does not yet have tickets, please get in touch with me, I have a discount code for you to save a little.

Looking forward to seeing a whole lotta people! See you there!

“You stay classy San Diego” – Ron Burgundy

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Entrepreneurial Lessons in 2009

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2009, you sucked! Good riddance to you! That was a horrible year that I just get sick thinking about. As it pertains business matters, it all started in late 2008, the second half of September to be precise, when the economy tanked. The entire country panicked, and the global economy didn’t respond any better. It really was the Global Economic Crisis, and as NPR is now reporting apparently it’s been “abated” but the effects are to linger for quite some time. One thing is certain, CitySquares was affected greatly and quite immediately. I won’t go into the details and the describe the punches we took, those we handed out, and the battle scars we have to show for it, but I will highlight some of the challenges and battles that really stand out in my mind:

  • 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.

Four Years

iStock_000002119635SmallToday is a special day for CitySquares. It was four years ago today that Bob and I launched the CitySquares.com website. We launched it with only 7 neighborhoods: Porter, Davis, Harvard, Central, Kendall, Union, and Inman. We actually held a launch party in Davis Square, invited local businesses, residents, artists, musicians and others to come and join the festivities. It was a blast! Check out the CitySquares.com Launch Party on YouTube.

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.

Decisions, Decisions

iStock_000006048082SmallAh, decisions decisions. They never end in life, unless you just decide to spend your life as a lump on a log. But even then you still have to make decisions, starting with “I’m going to be a lump on a log.” If, however, you’ve chosen a life beyond lumping on a log, your life is full of decisions. Every day we’re faced with them:

Should I get out of bed?
Should I eat?
Should I wear the wrinkled shirt?
Should I get gas?

Those are routine daily decisions that we all have to make, and there’s nothing  exciting or risky about them – we all make them. We’re not paralyzed by them, unless we suffer from a disorder, as some do.

There are other decisions that are far more important, that we don’t face every day, decisions that affect our lives and the lives of those around us. Decisions like…

Should I marry her?
Should I have children?
Should I buy this house?
Should I get that operation?
Should my child get that operation?

People who are in business for themselves, whether they’re a self-employed contractor doing roof work around town, or an MIT scientist who discovers a new  vaccine, face a whole different set of decisions. These entrepreneurs make a huge decision once they decide to go into business. Some decisions entrepreneurs face…

Should I start my own business?
How do I get my first customer?
Can I afford to pay a staff?
Can I afford to pay myself?
Do I really have a business here?
Can I make money?
Should I raise money?
Should I incorporate?
Should I trade equity for money?
How much control do I give up?
Should I keep doing this?
Should I fire this person?
Should we expand the business?
Can I keep doing this?

The list goes on and on. These decisions have a way of putting an abnormal amount of stress on an entrepreneur because they’re piled on top of the routine/daily decisions, the big life changing decisions, and yet at the same time an entrepreneurs decisions affect herself, her spouse, her children, her family, her social life, her employees, her partners, her customers, her investors, shareholders, board members, etc. There are more people who have a stake in an entrepreneur’s decisions than one might first realize. It’s facing those decisions every day that partly define an entrepreneur. Some are good at these decisions, some aren’t. Some can make these decisions with little help, others need lots of help.

The hardest decisions I’ve faced as an entrepreneur have been the ones that affect individual people – like having to lay someone off, or fire them. There is just no way around it – it hurts the entrepreneur, the employee, and those around the employee.

Recently I faced another hard decision. This one pertained the direction of my company and pertaining those who were at the helm with me. You might say that I was at a point where I felt like my number of options were becoming more and more limited. And for an entrepreneur like me, who’s a fast decision maker after a quick risk/reward assessment, there’s nothing worse than being out of options.

Over the last few months I’ve had to face a reality that was hard to come to terms with – that the company that I’ve built with Bob over the last four years, that I’ve put so much of myself into, was slipping from my grip. I was not pleased with the direction it was going and my vision for the company was moving towards my periphery instead of where it had always been – straight in front of me. Something had to change, and some decisions needed to be made. Others agreed.

Ah, decisions decisions. They can halt you in your tracks. Some people can go their whole lives regretting one decision, and it becomes something of a curse. I knew I was at one of these splits in the road but I couldn’t be hasty. This decision required a lot of thought, and it required a lot of smaller decisions along the way, like playing a game of chess or poker.

A couple of weeks ago, the decision was made and almost immediate effect at many levels. And at the risk of being secretive, but in light of the fact that this decision was a sensitive one, I’m unable to explain what the decision actually was. It’d be inappropriate of me. Also, not knowing the ultimate outcome yet, it’d be reckless. But what it pertains is the very course that CitySquares takes in the near future and long term future. It’s the difference between surviving and thriving. It’s the difference between growth and prosperity or slowly suffocating. It’s about change. And change starts at the top.

Sometimes you don’t know if your decision was the right one for quite a while, and sometimes you know instantly. Sometimes you can go back and change your decision, other times they’re finite. This one was finite.

I learned something during this process, and it was something that I knew but hearing it from one of my investors, hearing him articulate it, and having him look straight into my eyes while saying it, really drove it home. What I learned was this: I am the founder of this company. While I have shareholders and a board of directors, it’s me and my vision that the investors bought into. It’s my passion, my knowledge of the space, my guts and gusto, my vision that got us this far. And if I believe in myself at least as much as my investors believe in me, then I must have an equal amount of conviction and gusto when presented with decisions that do not align with my vision and strategy of the business.

At the end of the day, when I have to rest my head on my pillow, I have to be able to say “I made the right decisions today.” Not making the right decisions, and not making them in timely manner, is the difference between sleeping well and not sleeping well – the difference between doing right by my own Self, doing right by those that trust me (from investors and shareholders to staff and customers) and one day living with regret.

I’m extremely pleased with my decision so far, and I’m proud that I turned this corner as an entrepreneur. Time will tell if they were the right decisions, but I refuse to be a lump on log and let others make them for me.

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