Passion Renewed

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

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

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

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

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

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

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

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

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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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Kill Section 926

If you read this blog, you don’t need to be reminded that I’m an entrepreneur, or that CitySquares has been funded by angel investors from eCoast Angel Network, to Jonathan Kraft, and Mark Cuban, among others. The bottom line is that CitySquares would not be here today if it were not for our angel investors, but more generally if it were not for Angel Investing as a whole. Most importantly though, angel investing is good for America, that simply cannot be disputed. So why is Senator Chris Dodd trying to make it harder for entrepreneurs and companies to raise angel financing, and why is he going to raise the minimum requirements to be an accredited investor, and on top of it all make the SEC review every angel deal before it can get done?

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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Ten Conference and Networking Tips

The Kelsey Group, or should I say BIA/Kelsey, held their annual Marketplaces conference this week in sunny San Diego. A heck of a show it was. So good that I probably was only able to sit in a handful of sessions. I say that because when I first started going to Kelsey shows in 2005 I was a newbie to the local scene, a newbie to local search conferences, and I probably sat in on 90% of the sessions, and soaked up information like a dry sponge. And that was the intent – to learn as much as possible, and then learn more. While my desire to learn at these shows hasn’t changed, my priorities have – it’s all about networking now and prospecting and establishing business relationships, of all types.

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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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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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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When the Going Get Tough…

I’m posting this blog entry in two ways – video and the usual text blog entry. I thought I’d try this out and see how it goes. Please let me know your thoughts on all this, I’d love to hear from ya. Video is below, followed by the text.

[viddler id-2b584a47 h-370 w-437]

No doubt life is full of challenges, pain, suffering, obstacles – and all those things define who you really are. It’s not the good times that define you, shape your character, and test you, it’s the hard times, the darkest days.

This recession is doing exactly that to millions of people, if not billions. It’s global, and everyone is being affected – every day citizens, worker bees, small businesses, entrepreneurs, investors – no one is safe from this. And if you are not feeling the pain, than either you’re clueless and not paying attention, or you own a pawn shop.

CitySquares has felt the pain, pretty substantially. It started in the second half of September 2009, when the stock markets took a nosedive in the worst way. Our Q3 pipeline was a hefty one, and we were just on the verge of closing tens of thousands of dollars in new business. When the economy began collapsing, our pipeline just fell out from underneath us. It was pretty ugly. The first thing we noticed was the immediate and extreme reaction that everyone had to the economic downturn, but for us it was the small businesses that really highlighted the severity of things. They reacted as human beings, as real people – they reacted emotionally. So, over the next few weeks and into the holiday season we observed small businesses all across the country go totally radio silent. But what were they doing, aside from freaking out? They were trying to secure credit lines to pay their bills, trying to make payroll, keep their lights on. And all this right when the credit market was seizing up – no money for them. Then the holiday season showed up, and what do you have but small businesses with overstocked stock rooms, shelves loaded up with product that over the course of the weeks preceding the holiday season stayed that way. Now how are these businesses supposed to pay their vendors for those inventory orders? They weren’t able to move any product – and they’re stuck with all this inventory. Now it’s January and the invoices start showing up.

lifeboatThen it really got ugly for them. They started shutting their doors, turning their lights off, letting their employees go. All those businesses, those local merchants, who give so much of themselves to their businesses – closing their doors for the last time. It was painful for us to watch. And we too, felt the pain. Those local merchants, they’re our customers. So we got hurt pretty badly too.

Well, here it is now, July 2009, and the economy still sucks. But small businesses are a resilient bunch, somehow. Lots of them managed to get through that long rough patch, and the fog seems to be clearing up a bit. Although unemployment continues to climb, and consumer spending continues to fall, those small businesses that weren’t really going to make it to begin with seem to have fallen off the tree like dead leaves. Perhaps there was a bit of a shakeout, a necessary one? I’m not a data analyst, nor do I desire to be, but from our standpoint at CitySquares, we’re seeing a bit of a lull here – less businesses shutting their doors, and more businesses just hanging in there, maintaining, and even others that are wising up to online advertising (perhaps the subject for another blog entry).

Well, here’s my point of all this. CitySquares is not unlike small businesses. We are not loaded with cash. Yes, we raised money in 2007 and again in 2008, and sure that included some big name investors like Mark Cuban and Jonathan Kraft. But we’ve never been interested in raising a boat load of cash – for lots of good reasons. And because of that we are learning some really valuable lessons. You might even gather from this that because we’re not swimming in capital that we’re learning some lessons that others may not – what its like to really be lean, mean, and hungry. Just like in 2005 and 2006, when we were bootstrapping our business, we were forced to be really damn smart about how we executed on our strategy, and how we tested business model ideas. Here we are now, three years later, basically going through the same process.

CitySquares had to make some cost reductions, and that included lots of things, from renegotiating with vendors, to trimming the fat off our budget, and the worst part of all, reducing headcount. I can’t tell you the pain that I’ve felt having to do that last part – letting people go. It’s caused me more stress, sleepless nights, and soul searching than perhaps anything else in my professional life. It wasn’t the first time I’ve had to let people go and it won’t be the last. One thing is for sure – it never gets easier.

Today, like the small businesses all across the country, CitySquares is running very lean, and running a tight ship. We learned some very valuable lessons over the past couple of years, and I also learned some valuable lessons.

It’s actually pretty fascinating to see how people react and handle these kinds of stresses. This is when you really see who people really are, beneath the facade. Investors, board members, employees, vendors, partners, friends and enemies – you see their true nature during tough times. I can tell you straight up that there are some folks involved in CitySquares that have demonstrated their strength, their will to persevere, their guts, and those are the people that I want to surround myself with. Then there are others, who have demonstrated their lack of heart, passion, wisdom, their lack of leadership. Those are the people that I would prefer to be in the other lifeboat. Those people really scare me, those are the people that cause the plane to go down, the ones that will press the self-destruct button.

But perhaps most intriguing to me is how stressful times can inspire people to do great things, and with ease and control. In times like these you not only witness the strength in strong people, but the ability to dust off and not just get back in the race, but run to the front of the pack. Human beings are really damn good at surviving.

When people say, “hey ya know, it can’t get much worse that this right!” I always find myself responding quite quickly in saying, “Are you kidding me? Of course it can. It can get a lot worse!” And that’s not a way of suggesting that – oh no we need to head for the hills! Rather, it’s a way of saying – look, things can always get worse. You don’t know the bottom until after you’ve been there. So just prepare for the worst, get ready for it, but meanwhile work hard to make things better. You can always fall down another rung on the ladder. And ya know, in my personal experience, the ladder is pretty much bottomless. The higher you climb, the harder you fall. The idea is that hopefully you only fall a couple rungs, and not the whole damn way down.

Alright, well I’m speaking in tongue again. But I think I’ve made my point, but just in case I’ll sum it up this way…

Entrepreneurs: Things can always get worse. And rest assured that things will get worse. Maybe not today, maybe not tomorrow, but some day, things will get worse. Don’t ever think that you’re insulated somehow. That’ll be your downfall. Instead of looking down and kicking the dirt, or crawling around your cave looking for a better source of fire, get outside the cave and listen to the wind – watch the tides – look at what the animals are doing – look at the horizon – the signs are all around you. Go with the tide, go with the wind, go where the horizon is sunniest. Follow the momentum that is around you.

For CitySquares, that means we’re getting back to some basic concepts and focusing a whole lot less on complexity, and entirely on core value. We’re done listening to the weak ones, the ones who’ve never really been there or done that. We’re watching the horizon, listening to the wind, and steering our boat to go with the tides.

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Sixth Photo Meme

My friend Sooz tagged me in a little Interweb game called Sixth Photo Meme. Basically, Sooz went to her Flickr account, to her 6th page of pictures, and to the 6th picture on that page and then tagged me in the picture. Now although I’m not actually in the picture isn’t the point – the point is that this viral game spreads like wildfire. It’s fun! The one caveat is that you need to have a Flickr account to participate, but even still you need to have at least 6 pages of photos.

So here’s my Sixth Photo Meme! This is a picture of the best game of baseball I’ve ever had the pleasure to attend – October 17, 2004. It was the 2004 American League Championship Series, game 4 at Fenway Park – Boston vs New York. This was the game 4. The one that resulted in the best comeback in sports history, the comeback that ended the Red Sox’s 86 year championship drought. I had the great fortune of attending this pivotal game, this pivotal moment in baseball history. I watched Dave Roberts steal second base – the single moment, the single play that changed it all. This is a picture of Mariano Rivera, perhaps the best closer in baseball history, on the mound in the midst of this game as it unravelled for the Bombers. Anyway, here’s my 6th photo from page 6:
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So it’s my turn to pick 6 people to play this game. Here we go:

Ryan Sarver, Sean Coon, Nate Aune, Tara Hunt, Dana Zemack, CitySquares

Two Simple Statements

610xAs I was leaving the ILM:08 conference Friday afternoon I made my way around the various rooms and hallways to say goodbye and shake the hands of the many people I met with over the last few days. As I neared the lobby of the hotel I bumped into the Localeze crew hanging out and waiting for a cab to the airport. I walked over to thank them for the dinner and drinks from the previous evening. We joked around about a few things, as we usually do, and when I thanked Brian Wool, Vice President at Localeze, he responded “No Ben, thank you, we really appreciate your business.” I didn’t think much of it, we chatted for a minute longer and then I left the hotel for the airport.

Coincidentally, when I arrived my airport terminal I bumped into Geoff Jeff Beard, President of Localeze. We chatted a bit while until it was time to board the plane. I turned, shook his hand, and said “thanks again for the great time last night, really” and his response was “It was our pleasure, and thank you, we really appreciate your business.”

That’s when it hit me – “Thank you” and “we really appreciate your business” – two very simple statements, but so powerful. And sadly enough, as consumers and customers we just don’t hear it enough. Instead, we see a generic sign from the hardware store hanging in a window, or on the back of a cash register, that reads “Thank you, come again!” or “We value your business” but so rarely is it actually spoken.

When I sat on the plane I started to realize something – I’ve heard these statements many times from Localeze. In fact, I’ve heard it from each and every one of them either oh the phone or in person. I found myself rather dumbstruck by this, as simple as it is. All of this translates into something else, something vital in business – loyalty.

Like all companies there are a number of service providers, partners, and vendors that we work with at CitySquares. Nearly all of these relationships have lasted because, well obviously they provide value, but also because they appreciate our business and they make sure I know that. They make us feel like we’re valued. If I don’t feel like they appreciate my business, I’ll continue doing business with them but if someone else comes along and makes me a better offer, I’d give it serious consideration.

CitySquares’ relationships with our customers are our biggest asset. We have a high customer renewal rate because we take care of them, we provide them with value, and we appreciate their business. In fact, every month we have what we call Customer Love Day. Yeah I know, it sounds a little corny but that’s what it is; Customer Appreciation Day sounds so corporate and cliche. The point is that we make a concerted effort to make the time and we go out of our way to check in with our customers, provide them with additional value and to thank them and let them know that we appreciate their business. This is a process that’s simply in CitySquares’ DNA.

In these tough economic times, as businesses struggle in various ways it’s never ever too late to tell your partners and customers that you appreciate their business, to thank them. You can’t build loyalty in one phone call though, it takes time – but you can start today.

Clear a few minutes off your calendar and call just one of your customers today, or one more. Thank them, do something for them, go the extra mile. It only takes a moment and the worst you get out of it is a happy customer.