When I was in college, at Fordham's scenic Rose Hill campus in the Bronx, I deeply rooted into my community.  I was one of that handful of student leaders that ran five or six different things at one time and who couldn't walk from one classroom building to another without running into someone I had to talk to about a meeting, an intramural sport or something social.  Being intensely involved in community life there made the campus seem small and familiar. 

After I graduated in 2001, I remember it seeming impossible to feel the same way about living in New York City.  I thought to myself that only by being elected to public office or by being an actor could you plug into a big enough platform to create community around you in such a big place.  It was a time before the widespread use of social networks, obviously. 

Fast forward twelve years and I've rooted not only into the NYC tech community, but also participate in communities around recreational team sports and volunteering around waterfront paddling.  I joke around that the number of different ways that I could run into someone in the city is a bit ridiculous--but it's also fantastic.  I've created that same familiar feeling that I had on campus in one of the biggest cities in the world.

Passing on that experience has been at the core of what I do in the NYC tech community for the better part of the last decade.  I'm always looking for new ways to turn big and intimidating into small and familiar.  That challenge has changed over the last year or two.  Previously, the challenge was awareness--helping people find where the community was.  Over 7,000 subscribers later, my weekly newsletter has helped shed light on the comings and goings of NY tech for a lot of folks--and I'm thrilled that it's been able to help people connect.  Now, the problem is a little different.  

The New York Tech Meetup isn't in the back conference room of Scott's offices at Meetup anymore.  We're big time, and while that's great, I was reminded recently that "big" isn't always the interaction that people want to have.  New York Tech Day, with 10,000 people at Pier 94, can be intimidating just as it is inspiring.  When you see too many faces, you might not take the time to learn the names that go with any of them.

That's why I've been seeking ways to return to the small, familiar groups I used to experience back in 2005-2008.  Back then, we used to head to The Park--the restaurant over by the Highline, after the New York Tech Meetup at IAC.  If we had 15 people with us, it was a lot.  That's when we really felt like we had a community--when you could go to a big event, but then bring it back down to a handful of people you knew really well.

One avenue I've been using this year to accomplish that is food.  At SXSW, after feeling completely overwhelmed by last year's event, I decided to pre-book reservations at a bunch of restaurants far in advance.  When I couldn't get reservations, I used Taskrabbits to wait on line to grab tables.  I then reached out to the people I wanted to spend time with and offered up spots with small, curated groups around great food.  It was a fantastic way to dive in and get to know people, or reconnect with friends that I didn't get to spend nearly enough time with when I was in NYC.  I made SXSW small again and I loved it.  

I decided to take that same setup back to the tech community in the form of small group dinners.  With the help of the Kitchensurfing platform (I'm not an investor, I just like it as a user), I've gotten together with nearly a dozen hosts to have people fro the tech, startup, and digital media community together in apartments from Park Slope to Midtown, from the West Village to Williamsburg and beyond.  I pay for the hosts and fill the seats, but the hosts do most of the hard work--negotiating menus, booking chefs, and pretending that their apartments are always so clean and neat.  

The dinners have been fantastic.  It's been a great opportunity to get to know people better, and connect people locally who, in most cases, live just blocks from each other and had never met.  Someone asked me the other night why I'm doing this.  The best reason I could come up with is that it's the interaction with other people in the community that *I* want to have.  At this stage of my career, I don't get nearly as much out of going to a huge blowout event as I get when I have a great conversation with just a handful of people.  If I can share that experience with others in a scalable way, I'm all for it.  I will have setup at least two dozen of these things before the the year is out and it's the equivalent of sponsoring a two hundred plus person event, for just a couple grand of total cost in a completely manageable way.  That's important for one guy with a tiny fund.  

I've mostly sourced people from my own network and from recommendations, but now that I've got this operating a little more smoothly, I've decided to open it up a bit.  I can't guarantee that I'll be able to accomodate everyone--because I've been mixing and matching people that I think would make a great group, and there are variables like times, dates, neighborhoods, food preferences.  Still, it would be great to get some new faces.  

So, if you'd like to join us, fill out this form.  Tell us who you are and, of uniquely NYC importance, where you are, lest we invite an Upper West Sider out to Queens.  It might be a while before you hear anything, if at all, but I'll be doing my best to try and get as many people involved as possible.  Also, let us know if you're willing to host.

Salute!

I've had two entrepreneurs I know in the last week come to this same conclusion.  Despite the fact that they're great sales founders, selling isn't actually their job.  Being the sole salesperson on your team, no matter how good you are, isn't scalable.  You need to figure out what it is that you do to sell, the scripts you know by heart that you never wrote out, the way you get a feel for which customers are warmer than others, and find a way to teach it to others.  That's the way you build a real business.  When you reach product/market fit, companies scale as sales teams scale.  

Scaling a sales team is a completely different challenge than being a good salesperson.  It's about establishing process, tracking metrics and creating a supportive learning environment.  Some people will tell you that half your salespeople won't work out--but that feels a bit like conceding defeat to me.  Ideally, I think it's worthwhile to try to build the kind of sales environment where anyone could be successful--where it's about process and learning.  

When you're a startup founder, taking your foot off the gas when you know you have something that customers want is incredibly hard.  Cash is a drug--and it's hard not to make another customer call to get another hit.  You do that and you're taking time away from recruiting and training a team, or figuring out the right individual salesperson economics and incentives.  Carefully constructing the onboarding process and incentive structure of your first give salespeople has ripple effects that will be felt for a long time in your company (or a short time if you mess it up.)

I'd love to hear about tips, good resources, and experiences from early sales team members of startups.  Who is in the process of building a sales team now?  Who has built the best sales teams in NYC?  What did things look like for the first three salespeople?

The other day I went to dinner with a friend.  My phone was low on power--drained from listening to the Mets take 20 innings to lose a game.  I plugged in before we went out.

When we were ready to go, I instinctively reached for my phone, because I never really walk out the door without it.  We weren't going far, but that wasn't the point.  It has become an appendage--a tether to the rest of the world, preventing me from straying too far from the other billions.  

For some reason, I stopped.  I realized that all I was doing was heading out to eat at a new place I was excited to go to for the first time and to catch up with a good friend.  Neither of these tasks--eating, listening, talking, required an internet connection, let alone a phone.  I decided to leave it.  

"No phone with food," I said.  

We ate at Bar Corvo.  The food was terrific.  Get the chicken--it's incredibly tasty.  I focused on my friend across from me.  An interesting byproduct of not having the phone on me was that there was a little extra incentive to maintain a good conversation.  I couldn't supplement it with a wikipedia search for the official definition of "gratin" or a private viewing of the day's Instagram photos.  I had to be fresh, original, and thoughtful.  It was Humans Unplugged and it was really nice.

I think that's going to be the rule from now on--no phone with food--and I think I'm going to like it.  

New York City is a fantastic place to live--I've been here all my life.  I wouldn't want to live anywhere else.

That being said, it isn't necessarily the easiest place to live, but it's worth it.  

That's why I get excited when companies in my industry create businesses that improve the living experience of being here.  The mobile phone has the potential to be incredibly transformative for the lives of NYC residents.

So when the city government seems to be bending over backwards to make tech companies want to start and grow their businesses here, conducting business here might be another story.  Companies that make people's lives easier, should they run into entrenched Big Apple interests like housing and transport, aren't finding that NYC is as easy a place to offer their services to NYC residents.

Remember the on again, off again Uber and Halio taxi fiasco?  Hailing a ride using your phone in NYC has had more hiccups, false starts, and court filings than you can shake a Citibike at, and I'm sure it's likely to continue.  Ride sharing service SideCar was recently the target of a NYC police sting that resulted in two cars being impounded--cars belonging to drivers in their network offering rides to people. 

Gone are the days of stepping out onto the road and offering up a thumb, because what you might get back from the city is a finger.  

Government served an incredibly important role regulating ground transportation in the past.  Oversight prevents outer borough price gauging on behalf of car services and abuse of unsuspecting tourists who don't realize that LGA is closer to the city than you think.  

But do we need government playing the same exact role when loosely constructed networks can serve that same purpose.  A bad Uber or Sidecar driver will never get another ride--and user side data can instruct people what they should expect to pay before they get a ride.  It's not an accident that Uber drivers are some of the friendliest, nicest folks you'll ever get a ride with--they're working for stars!  

Technology can also redeploy assets quicker than government can regulate licenses.  If one particular area is being underserved, drivers on new networks can swoop in because of the economic opportunity to service customers.  Apps can attract drivers to areas they wouldn't otherwise cruise through.

It's better for drivers, too.  It makes getting your next pickup more efficient, and the user experience around taxi tipping has been shown to increase gratuities by nearly double.

That's why I faceplant when New York City seems to be the toughest place for all of these new services to operate.  It's embarrassing for us as a tech community.  We're supposed to be startup friendly, but the startups that want to come here and offer life improving services to the community can't operate freely.  

It's even worse when it comes to housing and hotels.  New York City has some of the highest average hotel costs in the world--and it's clogging up the free flow of entrepreneurs, startups and talent in the tech community.  If a kid out of Carnegie Mellon majoring in computer science wants to come and check out the Big Apple for a week, it will cost her a lot more than two bits to stay here.  

Enter Airbnb.  It's undoubtedly the number one form of lodging for NYC tech entrepreneurs heading out west to pitch for venture capital--and for founders and startup professionals to come here to work on deals with clients and other companies when they come here.  It makes NYC stays a lot easier.  

Yet, in a misguided attempt to crack down on poor quality short term hotels, the city passed a law effectively banning Airbnb unless the resident is in the apartment.  Instead, they limited the number of reasonable options.  I'm sure there were some really awful hell holes being offered up for cheap--but transparency is the solution, not bathwater tossing.  On a network like Airbnb, just like in the taxi situation, bad suppliers can't make revenue--and everyone has the incentive to offer a better service.  If anything, the city should be encouraging people to use Airbnb--because it effectively outsources the impossible oversight job of checking on the safety and cleanliness of every last lodging space in the city on a regular basis.  You can try to fight the illegal hotels, or you could encourage consumers to use options that have ratings, photos, and reviews in trusted communities.

The other problem with the city's Airbnb regulation is that a lot of people use Airbnb to make living in NYC affordable.  They'll shack up with a friend for a bit to defray the cost of expensive rent.  I know more than one NYC startup founder who keeps their business going because they essentially get their housing paid for by sleeping in the office or with family every so often. 

It's kind of ironic, too, that Airbnb helped people find housing during Hurricane Sandy, yet this new regulation returns the favor with a good swift kick in the teeth.

NYC is a difficult place to be a legislator at all--so many competing interests.  It's impossible to please everyone--but it does seem like we're a more difficult, more regulation intense place to conduct business than in other cities.   If that's the case for startup companies--that they're going to be less able to run their businesses here than in other places, what impact is that going to have for company creation here?  How many fewer ribbon cuttings will NYC's next Mayor be able to to attend for SF businesses opening up here if it's just a pain in the neck to offer up services that SF residents always seem to get first?

The hurdles that companies like Uber and Airbnb have had to go through in NYC are an embarrassment to our startup community.  Being on the forefront of digital innovation here doesn't just mean wifi and it doesn't just mean apps hackathons.  If the city's goal is to "help the world’s greatest city become the world’s most innovative city through online and mobile technologies that help citizens and enhance the quality of services", we need to be a place where regulation promotes new and more transparent business models, not stifles them with a ton of protectionist red tape.

I don't need to explain what Dots is, because you're already playing it.  Don't lie.

In fact, you're playing it so much, that it better teach you some lessons as a founder, otherwise, it's probably distracting you from your startup.

Here's a list to defend your high score from your investors:

1) Reset the Board: Don't fall in love with your first idea. Find the best possible starting point to create momentum.

2) Expanders: Eliminate as many features and possible directions right away. Clear the board of all the dots of one color in the same way that you focus on less things in your startup to do them better.

3) Buy some time: Raise a little more money than you need because cash (time) always runs out at the worst possible moment.

4) Don't look at the leaderboard: Other people will be dramatically more successful than you--to the extent whether they've discovered a cheat or are playing a different game altogether.  Don't worry too much and focus on your own game.

5) Just make squares: It's tempting to go for rectangles, but squares get you all the points you need.  Just focus on what you need to move your company forward each day.  Great startups are a series of small victories, not giant, pointless wacks at making a lot of noise.

6) Shrinkers: Get stuff off your plate when it's in the way.  It's easy to work on just the things you like to do, but focus on what's really holding you up and tackle it head on.  Eliminate the dots that are directly in your path to making a square.

7) Stay calm: If you start freaking out when things are starting to go your way, or not going your way, you won't be able to focus.  It's a marathon, 65 seconds at a time.

8) Don't freeze: Keep those fingers moving.  There's always something you could be doing--reaching out to one more customer, eliminating one more dot.  You don't have a lot of time, so idle time can kill you.

9) Know your next move:  The moment your thumb hits the screen, you need to be looking elsewhere on the board to figure out where you're likely to find another square.  If you have to relook at the board from scratch each and every time, or if you do that with your market, you won't be fast enough.

10) Don't stop short on a square: You see it, you're running your thumb over it... and MISS!  Nothing.  DAMMIT.  You went over it too fast, too sloppy, and now you totally effed the whole board.  Hit the easy ones out of the park and do what you need to do.  It's easy in a startup to run around like a chicken without a head, but that's going to make you stumble on the easiest of tasks.