D’ya play poker? Do you stay in for every hand? Of course not. Well, some of you may and I bet you lose a lot more than you win. I have a friend who’s reputed for staying in far longer than he should, and each time asked why he stayed in, he gladly volunteers, “I wanted to see what you had.” Needless to say he’s not a good poker player, and he loses more than he wins but he’s in it for the fun, not the profits, not to improve his game, not for the skill. That’s a choice he makes. The most disciplined skill a poker player can hone in his/her overall strategy is simply knowing when to fold. As sure as my friend’s strategy will drain his wallet, a slower and more frustrating way to lose is by losing ante after ante, bleeding your pockets empty, all while waiting for the right hand – which never comes. And some poker nights go like that. You never really win, but you never really lose – you just bleed out. Yet you can’t win if you don’t play, and you can’t play if you don’t ante. In poker, as in life, there’s a time for daring and there’s a time for caution.

I’ve played some good hands over the last few years. At times cautious and conservative, and at others more aggressive and risky. Professionally speaking, 2013 was a good year. A comfortable year. So was 2012. And the year before it. But I’m not one for comfort. I get really stir-crazy, and start to see structure and boundaries as schackles and walls. In May, a few months after Litle’s acquisition, I turned down what would have surely been a very comfortable position, a challenging one too, but comfortable. And when I left I set two goals for myself: enjoy summer and go into 2014 with a bigger ante on the table, or in other words at a startup I could be truly excited about (either my own or another’s) and one I could add real value to. So, I fully enjoyed my summer, through Sure Shot Labs I kept moderately busy and mostly kept off Ali’s nerves, and along the way started Influential, a nascent and hubris attempt at solving problems (as we see them) in the democratic process. With summer long gone, Sure Shot and Influential intentionally not long term career moves, I’m very excited to be joining a young and exciting Boston-based startup called CO Everywhere.

A little digression, if you’ll allow it: Back in 2005 when Bob and I started CitySquares our big and most broadly stated underlying vision was to bring all things local to the web. Broadly speaking again, we envisioned a platform that truly did exactly that and what became CitySquares’ tagline, Your Neighborhood, Online, was as good an articulation as any of our audacious vision. At the heart of the vision was location and everything therein – people, places, things, and all the metadata that accompanies it. While CitySquares made its mark as a pioneer of hyperlocal search, and while we did things in that five year period that took others years to do, and while those are very much things we hang our hats on, the result was different from our initial vision. It’s probably fair to say that we put up a big ante and maybe we didn’t get to play our hand as long as we’d have liked.

The startup world of 2014 is as different now as it’s ever been. Today’s startup landscape includes all the trappings that accompany today’s trends, mainstream or otherwise. In other words, the startups of the Web 2.0 movement were as different as those preceding in the late 90s, as startups today are different from those of the mid 2000s. Hindsight being what it is, local and location is still, in many ways, a fascinating and underserved, if not very difficult, space with many undiscovered shores and lands. And in this society, in the high-tech world, one thing is certain: adapt or die. You simply can’t get comfortable, companies and people have to always be on the edge, always be evolving. Otherwise you wake up one morning and realize you’re obsolete and hanging onto old ideas that simply don’t apply anymore and sales are flat (or worse) or no one will hire you.

This blog, odd as it is, was initially started (6 years ago as of last month) as a way to chronicle my entrepreneural journey, the second phase of it anyway. Looking back at this blog now, at the frequency of posts (and at times a lack thereof), it’s become mostly what I’d intended – a chronicle of my journey, at least that of my thirtees. Along the way there have been wins and losses, successes and failures, victories and disappointment but always antes. The journey continues now, and with it unpredictable twists and turns. And therein lies the crux of it: It’s time to ante up again. My next move has to be a smart one. A mere 5 years from now I’ll find myself in my early 40s so today I have a choice: stay comfortable and likely wake up one January morning in 2019 finding myself becoming obsolete, or to take a (calculated) risk, ante up, and stay relevant and on the edge. I choose the latter, I choose risk and the edge, I choose the game. The cards have been dealt.

Tying it back to CO Everywhere, what Tony and Dan have done with modest success is build, with little money and in a very short period of time, a beautifully designed app with one simple value proposition: put location first. And with virtually no investment in marketing they’ve managed to attract a respectable number of users and fans in no less than 14 114 countries. The current use cases are novel, and the potential is extraordinary. The product, young and nascent as it is, hooked me instantly and provoked big, visionary, and very exciting ideas and discussions from the first meeting with Tony and Dan over beers one summer evening. Initially I wasn’t looking for an opportunity but one revealed itself pretty quickly and it started to represent everything I was looking for in my next career move: founders with passion and talent who know how to execute, but also who don’t pretend to have all the answers, who’ve attracted exceptional technical talent, and a venture in a space I have strong expertise in and can immediately add value to, and those intangible qualities and characteristics that are so hard to find. And as was announced a few days ago, they just closed an unlikely round for a Boston-based consumer play. The challenges are real, a few are sobering, and I couldn’t be more excited to join the team.

A friend of mine recently suggested that I’m “so lucky that these things just fall into my lap.” I took great exception to that, offended even. From an outside perspective it might look that way, like opportunities and successes just come my way. Nothing could be further from the truth and I explained that nothing, certainly nothing in my career, fell into my lap or is a result of just being lucky. I had to remind him of some of the detours and accidents in my journey, and how unlikely this journey really was, which quickly recalibrated his perspective. And what is luck if not what Roman philosopher Seneca the Younger famously (and disputedly) defined as “what happens when opportunity meets preparation.” Or put another way, hard work and putting yourself out-there. The two are not mutually exclusive. In this day and age it’s not enough to work hard, and it’s not enough to be at the right place at the right time – it takes both to, if you’ll forgive the 2013 pun, get lucky. You have to ante up.

I’m eager to work with Tony and Dan, and will starting January 15. Their sense of urgency is palpable and what I continue to be impressed with is their clear-headed decision making. But perhaps most pronounced is not just their determination but it’s their chops. And that’s critical. Too many entrepreneurs have the determination, the vision, sometimes even natural leadership qualities, but they lack real skill. This may be their first funded tech startup, that they’ve founded anyway, but you might not know that at first. They’re seasoned and battle-scarred – which makes them all the more authentic. I respect their game. They’ve anted up before, but this is their biggest ante. And I want play the game with players who are in it to win and whose games I respect.


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