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.

 

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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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.