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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Jack Dorsey Offers Advice

At this week’s TechCrunch Disrupt, twitter creator Jack Dorsey demo’d his new product and company called Square, very cool stuff. Check out the video below to learn more. But what I enjoyed was Jack‘s very refreshing and relevant advice to entrepreneurs looking to raise money from venture capitalists. Surely this applies to angels too, but @jack was really talking about VCs. Check it out, it’s about 14 minutes in.

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Founder Institute Comes to Boston

In early 2007 a new website was founded by someone only known as Ted. The website was simply called The Funded. Simply put, The Funded allows entrepreneurs to rate and review venture capital firms and angel investor groups. While the site, and its founder, has been highly criticized, The Funded took off. For the first time ever, entrepreneurs had a place to go and rate and review investors, and for those searching for potential financing, a place to read those ratings and reviews. The Funded has, in it’s own small way, leveled the playing field and has served the entrepreneurial and VC communities well. For the first time ever, VCs were publicly being held accountable. For example, see here for the most loved VCs of 2009. Some say it’s a one-sided forum, and many just don’t care. Most entrepreneurs agree though – The Funded is a good thing.

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.

Founder Institute has already lined up great mentors for Boston, including;
  • Phil Libin, CEO, Evernote
  • Craig Kanarick, Cofounder of Razorfish
  • Dan Shapiro, CEO of Ontela
  • Eric Melin, CEO of Philanthropist.org
  • Stephen Hau, CEO of Sharable Ink and Patientkeeper
  • Doug Brenhouse, Cofounder of Metacarta
  • Ryan Alfred, Cofounder of Brightscope.com
  • Roger Yee, Former CEO of ShadowLogic
  • Matt Johnson, CEO of OmniStrat
  • And more…
The Institute training and apprenticeship program is complimentary with other incubators, such as Y Combinator and TechStars, both of whom have history in Boston.  “Several people have suggested that the program is competitive with TechStars… However, I just don’t see it that way and encourage all kinds of programs like this in the entrepreneurial ecosystem,” states Brad Feld (TechStars Co-Founder) on his blog, encouraging entrepreneurs to apply to the Institute.
Boston is the third East Coast location, eighth U.S. location, and 10th chapter of the Founder Institute worldwide. The Institute now expects to enroll 800 founders per year in a four-month training and apprenticeship program, differentiated by shared equity upside of all participants. Apply here today!

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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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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