Thriving Startup Community in Raleigh-Durham

There’s something about Raleigh-Durham’s high-tech startup scene that’s reminiscent of how the greater Boston area’s high-tech startup scene felt to me in the late 1990s and early 2000s. While I was 15 years younger then, and certainly more naive than I am now, that energy in Boston and Cambridge in those days was unmistakable and those who were part of the scene then will remember it as fondly as I do. Raleigh-Durham feels very much like that to me now and I suspect that other smaller markets comparable to Raleigh-Durham might feel the same way, as they each go through their own startup renaissance.  There are high degrees of enthusiasm, passion, and intelligence with very little arrogance, inferiority complexes and entitlement. While the startup ecosystem here has all the right pieces in place (world class educational institutes, state and local policy, public and private investments, infrastructure, talent, etc.) some for longer than others, the area needs a bit more time and cultivation until it gets to the next inflection point. There’s even a (mostly) friendly competition between Raleigh and Durham that adds to the area’s development.

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You Can Be Very Abrasive!

That’s what she said to me. It was around 2004 and she was a mentor to me. I held her in such high regard, I admired her and when she spoke I listened. We were having lunch on a beautiful spring day in Harvard Square, dining on a restaurant patio. She was cultured, she had the pedigrees, she’d been around the world and back, and she’d totally kicked ass over her highly entrepreneurial career. Now, in her early 60s, she was as wise as she was inspiring. And she said, “you know, you can be very abrasive sometimes.” My fork stayed steady in my hand while I paused and humbly and sheepishly responded, “I know.” I sat back to hear her out.

A few years later I find myself far from the guy I was then, yet very much still that guy. I feel like I’ve come full circle in many ways. And only when you go on that journey do you really learn. A pattern has been revealed.

Today I start a new stage of my career. After two and a half years at Litle & Co., as their Vice President of Marketing, and through their late 2012 acquisition by publicly traded Vantiv, I’m getting back to what I do best – startups and entrepreneurship. My experience at Litle & Co. was nothing short of educational and enjoyable. I learned so much. Most of all, I proved something to myself, and that was the biggest gain.

For the most part I’m taking time off, to enjoy spring and summer, to see friends and family, to enjoy life, but also to make my next move a smart one. The next stage of my career is an important one. At 37 it has to be wise. Not conservative, mind you, but wise. I often fantasize about a totally different career path, one of journalism, or of science, always something that might make real change in the world. As one of my best friends often says, “the last thing we need is another app to help me find the pizza, review the pizza, get a deal on the pizza, take a picture of the pizza, and clip recipes of the pizza.” I’m often frustrated by the lack of real innovation out there, truly transformative stuff, specifically in the digital space. Stuff that really makes a difference. But it’s not enough to be frustrated, that breeds apathy. Instead I’m embarking on something new here. I’m also often frustrated by what I’ll call the cult of personality that’s come out of and surrounds the Internet’s entrepreneurial scene, here in Boston, in NY, in Silicon Valley. Scenesters, hipsters, hangers-on. Me toos. That stuff is just such a turn off. And none of it even really matters. But again, it’s not enough to be frustrated and annoyed by it.

So with that I’m launching an experiment, if you will. I call it Sure Shot Labs. Sure Shot Labs will be the vehicle that helps me navigate this transition, these bumpy roads. Through Sure Shot myself and a few trusted and passionate colleagues will try something new for all of us. We’ll build products and invest in ideas we have, on our terms. The traditional start-up model is gone. The lean startup is here. We will consult, yes, we will make our clients happy indeed, and we will take the proceeds from those engagements and invest them in the lab, in our experiments, in innovation and in products. This will be fun.

When I think about that conversation with my mentor nearly 10 years ago, I think about the young man I was. I think about how “abrasive” I was. It was unearned confidence and it was fear. Back then I had to compete with others who were smarter, bigger, stronger, more experienced, more wealthy, more well connected, and more educated. Today I still have to compete with those people. And they still might be bigger than me, stronger than me, smarter than me, wealthier than me, more well connected and more educated. But what they lack, and have never been able to compete with, is my endless tenacity, my ability to wear them out, like a wolf and its prey. And the street smarts, the innate will to work smarter, to work harder, to out-think and out-smart, to out-play, to outwit and out-will. I’ve always been out of my league. I’ve always been in over my head. I’ve rarely done things their way. I don’t plan on starting today.

 

Point Counterpoint: Entrepreneurship

There are a lot of gainfully employed people out there who are considering the entrepreneurial path. I meet them all the time. Some are nascent entrepreneurs who have the idea but they lack the courage to just do it. They point to many things as reasons, excuses, rationalizations, what have you. Oftentimes these folks are listening to their gut – which is a good thing. They’re afraid of something, and they don’t quite know what it is. Having been on both sides of the equation, I thought I’d present my own version of Point Counterpoint based on some of the things I’ve heard wannabe entrepreneurs say to me. But first, a little history to create some context.

After futzing around in sales for a bit, I jumped into the high tech industry in the mid 1990’s and worked in a wide range of roles for Fortune 500 companies like DEC, GE Capital, Bell Atlantic, among others up until late 1998 when I joined a Cambridge, MA based dot com. That variety of work in the high tech and Internet industries provided me with incredibly valuable exposure, experience, and skills. It also fanned the flames of an entrepreneurial spirit that I think I’ve had all my life. After surviving several rounds of layoffs at the dot-com, my day came on January 4, 2001. The next morning, I woke up and told myself I was done being “an employee” and decided to start my own company, using the skills, experience, passion, gusto, and entrepreneurial energy that was now almost uncontainable. Hindsight being 20/20 of course, I started that company for a mix of the right and wrong reasons. The second company, CitySquares, I started for all the right reasons. I don’t need to walk you through my next 10 years, so I’ll jump ahead.

On January 4, 2011 (10 years to the day), I became “an employee” once again, not at a company of my own founding, but as Litle & Co.‘s new Vice President of Marketing. It’s been six months in this new role; at a successful, profitable, 200 person company, with a 12 person Marketing team, and I can say with both pride and joy that I’m very happy.

Having a solid decade of hard-nosed, scrappy, sometimes bloody, mostly enjoyable, and relatively fruitful entrepreneurial experience has given me an entirely new perspective and approach to being “an employee.” The kind of professional maturity, growth, and development that being an entrepreneur provides simply can’t be gained with any schooling or, I believe, traditional employment.

Point 1: I just can’t work my ass off, put in long days, week after week, month after month, year after year, all while putting up with someone else’s bullshit, stupidity, and politics with no real upside and payout at the end. So, being an entrepreneur puts me closer to the end-game, puts me in the drivers seat, and because I’m in charge, my success or failure is almost entirely up to me.

Counterpoint: That sounds really nice, and I said the same thing 10 years ago. The reality is that while, yes, you do end up in the drivers seat, you are in charge, your success or failure is almost entirely up to you, you still need others to get there. Unless your Tim Ferris, you’re going to need some partners (of some form), some staff, legal and financial services, and if you have half a brain you’ll leverage an advisory board. You might even need capital, and hence you’ll end up with interested shareholders, perhaps a board of directors. So yeah, now you’re the one creating the bullshit, the stupidity, and politicking. While you’re the one in charge of your success or failure, you’re also the one in charge of everyone else’s success or failure too. How’s that for pressure? How’s that for long days, weeks, months, years? The likelihood of “success” is no greater or lesser because you are in charge, if anything you just created more obstacles for yourself. It really boils down to one thing: how you define your success. Success means different things to different people, I’ve opined on this quite a bit here on this blog. So think about what you really expect out of this move you want to make, and sit on it for a while.

Point 2: I’ve got a killer product and I don’t want my employer to have a piece of it – it’s my idea, so I’m going to start my own company.

Counterpoint: Really? The only way is by yourself? I’m glad Christopher Columbus didn’t say that, or Neil Armstrong. Even Leonardo DaVinci had help from the Catholic Church. So OK, you’re the genius with the killer product, but you need to do product stuff right? Cool, and congrats on that title by the way, it’ll come in handy when the going gets tough, or when real business matters need attention – cuz you’re pretty much off the hook. Oftentimes you hear the “product entrepreneur” say, “I just need a partner, someone who can help me raise the money, move some product (aka ‘sell’ the product) while I build it.” There is nothing more annoying to me. If you’re an entrepreneur, you need to do that stuff too, jerk! So, because you’re the nerd with the new gadget you get to scurry off into a corner somewhere while everyone else protects you from the bad people who want to make money off it? How dare they! Maybe you should go start a non-profit then, or build it and give it to a third world country – all so you can sleep better at night and keep your moral high-ground. Face facts Wozniak, you need to get some skin in the game too. Being an entrepreneur is about making business decisions, not product decisions. You don’t get to bake your cake and eat it too, while others sell the cakes, clean the bakery, and stock the shelves. You need to develop some real business skills, skills that will pay off for you in the end. If you don’t develop those business skills, everyone else will figure out a way to take your toy from you while you’re picking your nose. Trust me on this, those bad people who want to take your toy and get rich, they got skills – they’re trickier than you are. You might be a genius, but they’re snakes. Smarten up, and think twice before you hit the streets with your fancy new toy. In fact, given all this, if you really don’t have the chops, really don’t have what it takes, maybe you wanna reconsider talking to your employer about it – but talk to a lawyer first (you know, the bad people who do law stuff).

Point 3: I have big dreams, man. I wanna live this life, I wanna go places and see things, but I wanna do it in style – like on my own yacht, with my friends. You know, I wanna be a pimp!

Counterpoint 3: Playa please! I can’t even respond to you without wanting to punch your mouth. Ya know what – you’re right. Go out there, baller, get that money. I’ll be right here when that album you were gonna drop falls through the cracks, or when your steroids website costs more to build than it ever generates in cashflow, or that “super connected” club promoter ends up being shady and stops returning your calls. Yes, lightning does strike and some people in this world (out of 6 billion) do get rich quick. But if you get struck by lightning, it ain’t gonna make you rich, it might make you a bit brighter though… we can only hope.

Point 4: I just can’t work for someone else. I need to work at my own pace, in my way, with my style.

Counterpoint 4: You must be a millenial. I bet you went to a Charter school too. Hey, I mean that with respect – you are indeed one of god’s special creatures. This world is going to be a much better place once those baby boomers and gen-x’rs are outta the way. I honestly don’t know what to tell you, Moonbeam. I think you have some really really hard lessons ahead of you, and you’re going to find out that mommy and daddy learned the hard way too. They tried to protect you, they really did, but they were kidding themselves and actually doing you quite the disservice. Where’s Tiger Mom? Can you spend a couple days with her? I think she’s onto something. No one appreciates the beauty with which you see the world, and no one quite understands that the world can be a better place if they’d only _____. I think you should lead the way. The fact of the matter here is that no matter what I tell you, no matter what anyone tells you, you are a special creature that needs to experience real pain and suffering before you will listen to anyone. Sorry, that was advice.

Point 5: Life is short, I don’t want to spend it working in a cubicle, or on a construction site.

Counterpoint 5: See above. Also, what’s wrong with work? You know, that’s just a part of life right? You realize that Julius Caesar worked hard, right? You realize that Bill Gates still works his ass off right? You know those special ops guys who killed Bin Laden, Team 6? Yeah, those guys work their effing asses off. Are you better than them? If you don’t want to work, drop out of society and backpack around the world. Or better yet, find something you’re truly passionate about, and find a way to make a living doing it. It’s simple. Now stop whining and get back to work.

I’ll stop there. I hope I’ve made my point. Entrepreneurship is really effing hard, and when people go into business for themselves (be it their own bakery, their own manufacturing company, their own high tech company, ad agency, whatever) – it’s work, it’s hard work. Entrepreneurship is no yellow brick road, Dorothy. It can be, yes, it has the potential to yield wonderful results. You really need to consider the reasons for becoming an entrepreneur. That’s what needs assessment, not how you’ll do it, but why you’re doing it.

Am I better off now than I was when I started? Oh hell yeah. Did I fulfill the dream I had when I started? Oh hell no. But that dream changed with time. I started down the entrepreneurial path when I was 25. I’m 35 now – I’m a different person, with different values, different perspectives, different dreams and goals.

After 10 years of entrepreneurship, personally speaking, I’m a much happier and healthier person, no doubt, and I’m a better member of society. Professionally speaking, I feel like I’m just getting started.

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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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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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