How I learned to change the oil in my car and found a new office because of Shake Shack and a hackathon

Random story that I recounted recently to someone the other day.  It's super interesting to go back and trace connections and relationships that led to new opportunities.  If nothing else, it serves as a good reminder that every thing you do now is an investment in the future.  

In 2009, I was introduced to Havi Hoffman.  She was working as a developer evangelist at Yahoo! and got me on a panel at a hackathon she was working on.  In turn, I wound up inviting her to a 300 person event that I threw at the Shake Shack in Madison Square Park.  After seeing my ability to bring a big community together, she wound up introducing me to TK because he was running a hackathon of his own around the first Techcrunch Disrupt in NYC in 2010.  

Hi Charlie,

My friends Daniel Raffel (colleague, yahoo) and Tarikh Korula (Uncommon Projects, Brooklyn) + Etsy’s Chad Dickerson are organizing a weekend Hack day on 5/22-5/23 in association with TechCrunch Disrupt. More detail from Tarikh below. They’d love your help getting the word out and can answer any questions. It’d be great to get a mention in NYC Innovation. Thanks in advance for help getting the word out.

Regards, Havi

I wound up not only helping to promote that event, but actually attending, because if a bunch of hackers were going to be in a place in NYC, as an early stage investor I figured I should be there.  So I went--the only investor at the time to actually hangout during the pizza and hacking part of the hackathon, not just the demos.

Techcrunch Disrupt is where I met Steve and Jared from GroupMe and what led to me backing the company when I was with First Round Capital.

Later in 2010, I was introduced by Fabian to Andres Wuerfel, who was leading Deustche Telekom's Innovation Group.  It seemed like a good intro for GroupMe, so then I put Andres together with the GroupMe team.

Andres stayed in touch.  When I launched my fund, he reached out and asked if I'd be willing to speak on a panel in Berlin.  Why?  Because someone who launches a fund in Brooklyn would have an idea of how ecosystems outside the Valley can survive and thrive--so that's what I spoke about.  It was a great trip, but it also reconnected me with some New Yorkers that I hadn't seen in a while--namely Chris Muscarella, the co-founder of Kitchensurfing.  

When I checked in on the app formally known as Foursquare, Chris reached out and invited me to a dinner in Berlin--which is where his co-founder Bo was from.

That's partly when my obsession with building communities around food began.  I got to know Chris and Bo and wound up at a Kitchensurfing chef test meal, as they were vetting the chefs that wanted to join the platform.  I met Chris' brother Stephen at that lunch.  Stephen is an interesting dude who builds things and wants to enable other people to learn to build things, too.  He bikes a lot and isn't too shabby at softball, so he wound up joining my softball team.  

He also wound up teaching me how to change the oil in my car.

Getting to know the Muscarella brothers is also what led to a change of scenery for Brooklyn Bridge Ventures.  About a year ago, I started talking to some of the crew from Studiomates about joining them in a new location.  Their old home at 10 Jay was being renovated and that community was trying to figure out where it would go next.  

As it happens, Kitchensurfing wound up growing out of their space in Gowanus and recently moved out.  Chris reached out to me to ask if I knew anyone that wanted to take over.  Our group was still on the hunt for space and so it wound up being a great fit.  

So by the end of the month, I'll be moving Brooklyn Bridge Ventures from Dumbo over to Gowanus and bunking up with a great group of folks that are tied into the same community that produced Brooklyn Beta and led me to my investments in Tinybop and Editorially.  Gowanus is an up and coming Brooklyn neighborhood that is now home to a Dino BBQ, the best pie place in NYC, a shuffleboard club, an Ample Hills and soon, a new boutique hotel.  

I'll still be in Manhattan regularly and making the regular ride up and down Brooklyn's western shore to my investments in Williamsburg and Greenpoint, but I'm excited about the new surroundings, my new housemates, and the even shorter commute to work.

10 Things I've Learned in 10 years of Blogging

1. The attention you get from saying something intelligent and thoughtful comes slower and in smaller amounts than the attention you get from being controversial, but it lasts longer, compounding over time.  

2. Focus on the topics you care about and that you find interesting, not what everyone else is talking about.

3. Take a position and stand for something, but be open to learning from others.  

4. The less words you need to make a point, the better.  It's also really hard to stop writing when you're passionate about something.

5. You don't have to talk about your personal life for people to get to know who you are--let your personal style shine through your professional discourse.  

6. Try to make one point at a time.

7. Nuance is lost on crowds.

8. You can rarely predict what other people will find interesting about what you have to say--and it's never the things you say to try to be interesting.  

9. A small group of people will spite you for thinking you have anything to say whatsoever.  Listen to what they have to say, check yourself, and then ignore them.

10. Take all the time in the world to go from someone who asks a lot of questions to someone who makes a lot of statements.  

When New York City comes together for the Marathon #ingnycm

There are only a few times in my life where I felt like all of NYC was on the same page--sharing the same moment, and most of them were pretty bad.  We all went through 9/11 and Hurricane Sandy together, but of course, we'd rather not have had to endure those tragedies, even though we were resiliant.  

The blackout was shared citywide, and I suppose we fared ok, taking it in stride and even having a little fun, but again, we probably wouldn't choose to go through it again if we had to.

Sports championships aren't the same.  Yankee fans weren't all that enthused in '86 and lord knows us long sufferring blue and orange folk weren't thrilled to have to see the Pinstripes come down Broadway time and time again.  At least I'm not a Jet fan, too.

But yesterday--yesterday was all in for the NYC Marathon, including me.  I finally ran my first after last year obviously didn't work out.  The race was extremely hard.  I'm not going to lie--it was the hardest phyiscal thing I've ever pushed myself to do, and I say that after doing four NYC Triathlons and a Tough Mudder.  

Pro Tip:  Write your name on your shirt so everyone cheering will call your name out across all 26.2 miles.  That really helped.

Being a part of yesterday was like something I've never experienced.  Literally, the whole city was watching--across so many different communities, both local and international.  Standing on the Verrazano Bridge was amazing--and it's the one time you can do that.  I've cycled over just about every other bridge we have.  

Honestly, it was really hard not to run too fast, which I completely did, because of all the excitement.  Yes, I blame you, NYC, with all your cheering, makeshift signage and little kid high fives, for convincing me that I could run at an 8:15 pace the whole day.  That dream died around Mile 17, with 8:30 dying around Mile 20.  

Damn you supportive folk!

I saw my dad just after the bridge, on the turn to 92nd street in Bay Ridge.  I ran out of the turn over to give him a high five.  I think he was holding the "Go Charlie" sign my mom had made for one of my triathlons.  Hilarious.

I'm glad he made it out, because he has a knack for talking himself out of crowds and events.  He'd generally watch things on the big screen and his couch, and avoid the frustration of parking, pushing, shoving, but he picked out a spot and made it work.  

I need to thank two other specific people.  One kid, I'll probably never know.  Around Mile 18 on the Upper East Side, I was in serious need of some food.  I burned right through breakfast, and was on the hunt for something solid, regretting that I had passed on earlier offerings.  I visually scanned the crowd for small yellow curvatures and spotted one out of the corner of my eye--a little kid who was awkwardly holding onto a banana.  He was so small that I think he was standing under the rope.  I'm not totally sure he knew what he was supposed to do with it.  I almost ran past him and then doubled back a little bit with my hand out.  I hope that wasn't his banana, but he did hand it to me as I approached.  It was a lifesaver.  Thanks, kid.  

Once I got through the Bronx and back into the city, I was in one foot in front of the other mode, chanting "Forward" to myself as I mentally did the math on how fast I needed to go to still make four hours.  Things were not going well and the mile markers weren't coming fast enough.  As I exited the park, each attempt to move just a little faster was greeted with cramps in each calf.  

Then, out of the blue, I saw Cyna Alderman, who runs the NY Daily News Innovation Lab and who couldn't be more enthusiastic about working with the startup community.  A career lawyer, she's turned her attention towards innovation in the publishing space and has been incredibly fun to work with.  I didn't expect to see her--other than my Dad and a random friend from junior high school I hadn't spotted too many people in the crowd that day.  It couldn't have been better timing.  She screamed her head off when she saw me and it was enough to kickstart my legs.  I started my ususal all out sprint to the finish with about a half mile to go.

My legs had other plans and my left hamstring cramped up big time.  I said out loud, "Oh, no no no no... we're doing this.  I don't care, " and ran through it.  I'll deal with you later, legs.  I sprinted into the park and grunted my way in with each step.  There might have been grandstands of people, I'm really not sure.  I just locked onto the Finish Line, and just pumped as hard as I could. 


It was incredibly rewarding--but honestly, that wasn't even the best part.

The best part was after--on the street, in the subways, on Twitter and Instagram.  Everyone knows what you went through.  The moment I finished, I was getting texts of congratulations.  I called my mom as soon as I crossed, knowing that she was tracking me on the iPad she's just learning to use.  She's not feeling well enough quite yet to navigate the walk and the crowds, but the internet and Apple brought the race into her living room in a very personal way.

Some Hispanic guy on the subway fistbumped me after asking about the run.

"All five boroughs?  Serious?  Mad props, yo.  Congrats."

There was a couple who had just gotten engaged riding along with us.  Seemed like she said yes, but perhaps on the condition that he gets his lazy ass into the race next year.  

A girl tried to give me her seat, but I was too afraid I wouldn't be able to get back up again.  I'd rather lean against the pole in my bright orange poncho, but thanks.  The sales associate in Foot Locker asked me if I had won--and I thought about the Kenyans.  You know, everyone thinks what they do is about stamina, but then you have to remember that they're running like 12-13 miles per hour, too.  That's the most impressive part about their run--they're running the whole marathon faster than most people can sprint.  

Everyone I saw on the street congratulated me--and there were thousands, millions of people headed home, talking about the race.  Everyone gets behind you, whether they know you or not.

Well, thank you, New York.  I couldn't have done it without you.  I'm glad to see you back up on your feet after last year.  It's days like yesterday that make me wonder why anyone ever asks me, "Do you think you'll ever live somewhere else?"  



Making the NYC Community Smaller

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.  

Outdoor Tech #kitchensurfing

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.  

Tech Kitchensurfing #2... Another big success!  Thx to @ohheylara for hosting!

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.  

Tech #kitchensurfing still going... Prob should have taken photos beforehand.

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.



No Phone with Food

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.