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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