There are certain realities behind venture capital one cannot escape from:

• At the end of the day, the more of the best companies we own, the more money we make. 
• We don’t always know which companies will be successful, but if a bunch of other smart people think that a company has promise, there’s a good shot we’ll want in.
• We don’t always want to get off the merry-go-round the same time the entrepreneur does—and often times we want to go around again, at twice the speed.

Fortunately, some firms, like the two that I’ve been fortunate enough to work for, Union Square Ventures and my current firm, First Round Capital, understand the following:

• Owning less of *more* great companies works just fine, too—especially if that means you’re left with highly incentivized entrepreneurs who receive appropriate amounts of financing at the right time, focusing their efforts.
• We should strive to be *the* smart people that other people want to work with—by working hard to get smarter about the areas we invest in.
• At the end of the day, smaller funds can deal with the “high class problem” of the $100 million exit just fine, because we don’t need a billion dollar exit to make our find economics. 

But why do I like working with startup companies? 

I think that’s important for someone to understand when pitch their idea or project and agree to take on an investor.  I’d encourage every entrepreneur to ask the people that they’re pitching to, “Why do you do this?”

Some people are deal guys (or girls).  Always be closing—they love the transaction.  They just like having money behind them and putting it to work.  The bigger the deal the better.  They’re tough negotiators and they like pushing the envelope on how much they can get.  It’s a money and power thing.  Their steak dinners are outlandishly full of more food than anyone can actually eat.  Perhaps they were salespeople or bankers in the past.  I’m definitely not that guy. 

Other people are all about having better toys—getting into the hot deals.  They need the fastest, the best, the smallest, and their stuff is better than yours.  They don’t just order steak—they order the super secret cut of Kobe steak that was grass fed by albino ninjas wearing a certain kind of slippers.  They’ll wait until the train looks like it’s leaving the station and then they’ll come swooping in, absolutely needing to push their way in because they need to have it.  I’m not that guy either.

Me? 

I think I’m two things.  First and foremost I’m a relationship builder.  I doubt you’ll find someone in NYC who knows as many people in the innovation community as I do—simply because I love it.  (And PS…  there’s still a few thousand of you I haven’t met yet!)  I love meeting and getting to know interesting people—and venture capital just happens to be an industry where you’ve got unparalleled incentive to make a habit of this.  Plus, this is a self-selected group particularly high in awesomeness.  Maybe that’s why steak is celebratory food for me.  My best friend of 24 years and I take each other out to top tier NYC steakhouses for our respective birthdays.  Sure, we love the food, but it’s really all about the person on the other side of the table—and it’s the same with startups.  The people on the other side of the table over the last 6+ years have been amazing to work with.

Second, I’m a systems designer of sorts.  I like thinking about how data and other elements flow through a system and produce outcomes.  It’s the way a portfolio manager constructs a pool of assets within certain constraints.  It’s fascinating to me to try and take the randomness out of the equation and to try and figure out where the startups are coming from, what kinds of people are building them and what is making them successful—to turn those learnings into a strategy with actionable criteria, filters and decision points.  What that means is that I’m trying to figure out whether the waitress at Del Frisco’s is actually flirting with me or whether she’s systematically making every dumb guy like me feel like they’re special to get a better tip—and what percentage increase that generates in her net pay.  These are the kinds of things I’m thinking about.

Lastly, I have this teaching gene.  I take a lot more pride in the success of others than in my own.  When I play softball, I could get 4 hits in a game and not be nearly as excited compared to when that girl who never gets a hit drives in her first run after I taught her how to swing.  Now, granted most of the entrepreneurs I meet wind up teaching me more than I could ever teach them, it still means a lot to me to be able to help someone achieve success.  It’s kind of like introducing someone to the crabcakes at Ben Benson’s—it’s great to be able to help someone have a great experience like that.

And as a bonus, another driver of why I love working with startups is my New York City pride.  I was born and raised here and love when people find what they’re looking for here—success, inspiration, a challenge, or just a good sysadmin. 

For the record, I’m not as big of a fan of Peter Lugars or Sparks as others are, and Del Frisco’s remains my favorite.  Other solid choices are Old Homestead, Wolfgangs, Angelo and Maxies and Strip House.

It's been a busy couple of weeks, but I wanted to recap my first triathlon-- the Nautica NYC Triathlon. 

So let's start out with my expectations coming in.

I taught myself to swim this year--at least to swim with any kind of regular stroke. Before that, you could bet on me not to drown and be an awesome water treader/doggie paddler, but that's about it.  That being said, I still wasn't very confident in my freestyle, so I decided to do a breaststroke.

I figured about 38 minutes for the swim, and wound up doing it in 20:56. 

Thank you Hudson River current.

Seriously, the current is insane.  As soon as I got into the water, I had to hold on to the barge to make sure I didn't float down river too early.  You could go down on your back making snow angels and probably be there in about 30 minutes. 

What was really annoying, though, was that it took so long from when I got there to when I actually got in the water.  It's nearly two hours of just standing around, getting in lines, etc.  I suppose there's not much you can do about the whole thing, but it does require a lot of patience. 

That leads me to Tips #1 and #2.  Some people try to save time by bringing all their stuff the day before to lay next to your bike.  This would be a great idea, except that this year, it rained.  So if you do bring stuff... seal it all up or cover it.  The guy next to me on the swim line returned to soggy running shoes. 

Second tip is to bring your own black marker.  You need to have your number on your arm and your leg, but the lines for getting marked were way long.  Save time by bringing your own, asking the person next to you to mark you, and then throw the marker out.

When I first got in the water, it was a bit crazy.  People were climbing over me to swim, and I was definitely getting kicked.  Fight through it and get over to the side as much as possible. It's every swimmer for himself for the first 100 yards or so.  It threw me off and I had real trouble getting my stroke going.

Once we got seperation, I mentally regrouped and settled down.  I tried to be as deliberate as possible about my strokes--and once I did that, I started moving fine.  One thing about doing the breaststroke in a wetsuit is that I was actually too bouyant.  My legs and feet kept popping out of the water and so I was having a bit of trouble keeping them down.  Next year, I'll try to get a shorter suit if I use the same stroke.

I may very well use the same stroke, because, to be honest--this isn't about swimming.  How much better could I get?  Could I shave 5 minutes off my time?  Even if I did, it wouldn't nearly compare to how much time I could shave off biking and running with improvements there, so why sweat it that much?

First transition went pretty well.... 6:21.  I was wearing swim shorts under my wetsuit, so all I needed to do was throw on a shirt.  I put on mesh shorts over the swim shorts just b/c I didn't want to be all Spandexy looking.  Low cut socks and my sneakers, which I had opened up the laces of nice and wide earlier finished it off.  Last thing you want to do is kick off your shoes in the beginning and waste 30 seconds picking out a knot or something.

The actual biking wasn't so hot.  It was very hilly and I had the absolutely worst bike in the race--no question.  I mean, I didn't even have racing handlebars.  It was pretty sad.  Guys with teardrop helmets and those solid back wheels were humming by me.  On the downhills, I just didn't have the gears to maintain my speeds.  I got up to about 32 MPH on the downhills, but I had to slow down to 25 before I could actually continue pedaling for real. 

That's what makes me want to do it so badly again next year, because I know I can improve so much on my bike time with a better bike.  I finished in 1:26, but there's no way I can't shave at least 10 minutes off my time--and in this race, ten minutes brings you up 20% in the rankings.

Second transition was quick... 2:13, because it's really just getting off the bike.  This is where I made a pee stop during the race, though.  I think it would be hard to go the whole race without it given how much water and stuff you're told to drink beforehand--despite the fact that I went in some bushes right before the swim.  TMI?  Sorry... there was like one portapotty for every 1000 swimmers.  Everyone was doing it. 

The run was great.  I'm a good no energy runner, and it's only a little over 6 miles.  So, no matter what I had left, I'm just good at willing my legs to maintain a certain stride at a certain pace, despite the hills around the park.  I even sprinted at the end with whatever I had left!  My run time was 49:43 and my overall finish was 2:45:40, which was just below the median for my group.  I might be able to go down to about 47 min, but that's probably where I'd top off.  I don't think I could do much better than 7:30 min miles.

The race was great fun--definitely doing it again.  Triathlons are great because you never get bored of any individual activity--so you don't really have enough time to listen to your own head doubting your ability to finish. 

With about a minute better on the swim, 12 min improvement on the bike, and 2 min off the run, I'll be trying for 2:30 next year.  Can't wait!

This Sunday morning, I'll be competing in my firt triathlon--the Nautica New York City Triathlon.  It's very exciting, but honestly, I'll just be happy to finish.  I basically learned to swim this year, and the only stroke I could really figure out how to last a mile at is the breaststroke.  So don't count on me breaking any records in the swim.

I told my college roommate that I think it will take me 40-45 minutes to do the swim and he replied, "In that current, a bag of Doritos could finish in 45 minutes."

So, expect me to finish right behind the bag.

Anyway, if you want to see me, here's an estimation of where I'll be and when.  If you see me, please tweet out or post a Twitpic and mention my Twitter screename @ceonyc.

I'm looking at the times from last year and eyeballing it makes me think that 40 minutes would be bottom decile--but I am really slow, so let's say 38 minutes is my swim target.  Tack on another 6 minutes for transition, since this is my first.  I'm getting in the water at 7:33AM, so that means get out of the water at 8:11 and start biking at 8:17AM.

Actually, if you wanted to catch me a few times, you could come by the swim exit/bike start at 8AM on 79th Street, hangout there for a little while, and then head towards Central Park after you see me.

I don't have the best bike in the world, but I'm pretty sure I'll be able to do the bike in about 1:25.  That means I have to average about 17.6MPH and I'm pretty sure I can do that.  The route is north to the Mosh parkway in the Bronx, back down to 59th street and then back up to the transition area.

That means I'll be back in the bike transition area at around 9:42.  Since I'm just hoping off the bike, ditching it, and running, this should be a quick transition.  Let's say 2 minutes.  Ok, so I start running at 9:44, and I think I'll be on about an 8:30/mile pace.  I definitely want to finish the 10k  in less than an hour and it looks like about half of the people did that.  I'm a good runner when tired--can run on next to no energy, so I'm cautiously optimistic about being in the top half of the runners.  That means I should finish at 10:40 for a total time of 3 hours and 7 minutes.  If I were running last year, that would put me just below the median.  I'd be very happy with that. 

Here's a rough estimate on a map:

The other day, I wrote about how something seemed, well, gray at SXSW--like something was missing. It had been kind of--meh.

I felt like there were too many panels that just went through the motions, and the parties were just kind of crowed and rather uninspired.  Throw in some nippy, cloudy, rainy weather on top of that and what it all was amounting to wasn't a heck of a lot.

Then, something happened on Sunday. 

The sun broke out in the afternoon and it got warmer.  Almost like magic, the buzz started to return.  People got excited.  More people piled out into the surrounding streets, filling Austin with geek chatter.  I had a fantastic sushi dinner (yes, sushi...  we had all had more than enough ribs over the course of the weekend) with the Angelsoft folks--we could have featured our discussion as a panel in itself, talking about what makes content inspiring both online and in person.  Around nine last night, I wandered over to the Tumblr party at the Cedar St. Courtyard. 

The line was pretty long, but luckily, we spotted David Karp and he slipped us in the upper patio door.  Two minutes later, he was bringing food to his guests--quite a number of platefuls at a time.  Perhaps he's done the busboy thing before. 

Cedar St. Courtyard is a fantastic open venue with neighborhoody/block party feel.  The crowd was really fantastic.  Everyone was in a good mood because of the weather.  I met John Malone for the first time and we had a really great conversation.  Apparently, he's been lurking around my blog for a while!  I also caught up with Richard Johnson again after seeing him earlier in the day.  Peter Kafka was there, too, and we were joking around about how much easier it was to catch up with NYC people while we were in Austin--no calendars, no conflicts.

If you're ever in the middle of an otherwise dull conference, do yourself a favor--find the New Yorkers.

Around midnight, Gary Vee tweeted:

"Going to my hotel room to pick up 6 cases of wine and bring it to the Tumblr party let's make it a 1230am thing .. I'll tweet when Rdy"

I don't have to tell you how much of a party it became after that.

Between the venue, David and John's hospitality, and Gary Vee going the extra mile, this was the embodiment of what SXSW was supposed to be--inspiring people gathered together in an inspiring place for a blending of the professional and the social.  Even people who weren't at the conference were tweeting that it was obvious that the Tumblr party really rocked.  So thanks to all involved... Spending my night at Cedar St. really turned the whole event around for me.

Now if only everyone else had dance moves like Crystal Beasley, then we really would have had something. 

When I worked in institutional asset management, my managing director was very much an academic, and influenced the way I think about the world significantly--particularly around the nature of risk, uncertainty, and attribution of success. He always tried to look at things as a set of bets. You never knew exactly how your investments were going to turn out, but if you had a clear idea of what your bets were, you could at least manage where you were taking your risks.

In my life, I have a very clear bet on relationships. I know that I am relying on the strength of the bonds I have made with people to get me to the next level. Relationship bets often feel a little bit like insider trading--because its information you alone have about your experiences and information that give you any kind of certainty. Its certainly not public information, and it often appears sketchy or risky to depend on a relationship to come through.

On the contrary, that's something I feel comes through more often than not. Surrounding myself with good people through strong relationships has paid off for me time and time again, and I think its the one aspect of creating a business that entrepreneurs neglect most.

"Who's going to come through for you?" is something I want to ask most newbie entrepreneurs I meet. "Who is your friend in PR who will help pitch your story? Are your angels there for you when the money runs dry?" You can't necessarily put this into a business plan, but its as sure of an inside tip if there ever was one.

I was having a conversation with a friend of mine who is a member of the Church of Latter Day Saints (a Mormon) about being chaste.  (About her being chaste, obviously...  bit late for me.)  Oh and PS, she doesn't agree with her church's stand on gay marriage and hey, neither do I, so lets cut that comment bait off right away.

I have to be honest, defending people's typical behaviors with regard to sex isn't the easiest thing in the world.  It's especially hard when you're like me and you don't drink.  I'm already in the mindset of not doing things that pretty much everyone does because it's just not something you want for your own life. 

The reality is that most single people's personal lives are either a trainwreck or one in the making, and sex is often a complicating or distracting factor.  It emotionally binds you into situations you'd probably be better off without and it's often misinterpreted.  In fact, I'd venture to say its misinterpreted more often than its presence is interpreted correctly. 

I asked my friend a whole bunch of questions about her feelings and philosophy.  I made the argument about it's ability to bring two people who are in love closer together, and she asked me if you were in love why wouldn't you get married?

And therein lies my achillies heel in this conversation.  I've never had a particularly good answer to that question, because I feel like most people overcomplicate relationships.  I've been in a couple of situations where if the girl would have been up for it, I would have absolutely been married now.  I just feel like nothing could possibly prepare you for a lifetime committment so the best you can do is find someone you care about that you think you can handle the unknown with and make that relationship into what you both want it to be.  The idea that any of that is predictable when the divorce rate is 50% just seems like a lot of insecure indecisiveness to me.  I honestly think that my chances of a happy life with the next person I fall for are just as good as they are with any other person I might fall for... or, moreover, that I have no way of predicting otherwise.

So when I see young Mormon couples get married after just a short period of time, I totally get it.  In fact, I can't help but feeling a bit envious of people who so actively make their lives what they want them to be and work hard at overcoming the difficulties.  It's a lot more admirable than us New Yorkers hemming and hawing about not being able to meet anyone well into our 30's.  Our situation is kind of sad in comparison actually.

It's an interesting thing to be introspective about--and I realized something she described the pain of seperation when relationships don't work out--and how that can be exaserbated by intimacy.  Physical intimacy doesn't create emotion--it reflects it.  On one hand, you could use that as an arugment to support chastity.  On the other hand, since it's not creating any, then it's not really making it more difficult when a relationship doesn't work out either.  And that's, when it comes down to it, what I realize that I fear and what most people want to avoid in the first place--being hurt.  Choosing to be intimate or not with your partner at any given point, in my mind, doesn't increase or decrease the chances of being hurt.  Lack of communication, lack of honesty--these are all things that cause pain--not intimacy.  I don't want to get hurt anymore than the next person, and I don't take on a relationship assuming it will fail.

So, I think, when it comes down to it, focusing on the act is really focusing on the wrong issue.  I found myself feeling like I was making the conversation all about sex, and it's easy to oversimplify it that way.  That's a lesson I had to learn about alcohol early on--that you could very easily throw the baby out with the bathwater (bathtub gin?) and make the whole issue about drinking or not drinking, versus the kind of relationship you want to have with others and yourself.  By choosing to be chaste to the degree that practicing Mormons do, you're really choosing a certain way of relating to other people--one without a certain level of risk, vulnerability...  and it's not necessarily how I want to encounter people--with preconditions, limits, boundries. 

Will I find a relationship that naturally developes its own unique path around intimacy?  Perhaps.  Do I want to be thinking about those limitations on the first date?  That presents a lot of difficulty that can suffocate a relationship from the start. 

more music charts

Why are markets for people horrifically bad?

Finding the right hire? Extremely difficult.

Finding someone reasonable to date? Darn near impossible.

The market makers--job sites, dating sites, extract a lot of value in the middle and never really seem to come through.

I think part of the reason is the lack of data and how to understand it. I want to throw my blog at a dating site and have it understand the semantics: The food I eat, the sports teams I follow, the career I'm in, and the places I frequent. But why stop at my blog? Throw in Twitter, last.fm, del.icio.us, and Flickr, too.

Sites like Spoke, Naymz, and Rapleaf will just point to people and their digital footprints, but no one really takes the time to understand them across various services.

It's pretty obvious that I'm a Met fan, regardless of what I list in any prepopulated field on a social networking site. I've talked about the Mets on my blog and I have Flickr pics of Shea Stadium.

Careerwise, it's also pretty obvious that I know something about social media from my digital presence...but the search that people really want is who in NYC has 4-8 years experience and just talks about "users" the most.

Its not just more data, but also understanding the data in its context.

Sometimes life moves faster than you can possibly imagine--like when a relationship suddenly sours. One day things seem fine and the next, every exchange is toxic and things are snowballiing out of control.

Things slow to a crawl at the worst moments sometimes. People in hospitals seem to experience time with unprecidented drag. My one hospital experience--sitting in a Bronx emergency room with 104.4 fever and Lyme Disease, seemed to take forever--even though it lasted only 36 hours so I could get my fever down. What went in the blink of an eye was the softball game I pitched directly after I got home. I'm not sure I remember any of that.

When I was little, little league at bats were so quick. II walked up and in the blink of an eye I turned around and walked back. I couldn't tell you anything about the short sequence of pitches I had just faced.

One day, I made contact finally, and everything started to slow down. I felt like you couldn't put one by me and I had enough control to place the ball into right field. I could see what used to be a blur.

Ever just lay around with someone special late on a Saturday afternoon? You move slow, but time moves fast. Doing absolutely nothing passes four hours in the blink of an eye. All of the sudden, you're amazed at what the clock is telling you. You and your significant other seem to have slipped through cracks in the space-time continuum.

If only all the rifts could be so stragtegically placed.

I was talking to my entreprenuership class the other day and made an important discovery--a lot of them lacked for inspiration from the people around them.  A lot of us have great friends--mostly people that life just put in our laps by geography or by shared interest--and they wind up being people you share a lot of history with.

However, those aren't always the people that get your brain stirring the most.  You know what I'm talking about--when you can actually feel, even hear, that little hamster spinning away on the wheel.  Your mind races faster than you can speak, and you trip over your words as you try and get them out into a verbal blueprint of some big mental breakthrough.

Marc Andreessen once quoted Dr. James Austin on the topic of luck, and how just getting your mind going increases the chances that you stumble upon something big:

"A certain [basic] level of action "stirs up the pot", brings in random ideas that will collide and stick together in fresh combinations, lets chance operate.

Motion yields a network of new experiences which, like a sieve, filter best when in constant up-and-down, side-to-side movement..."

I have a friend that is always coming up with big and sometimes ridiculous new ideas.  Once, he was going to get an aquarium for his apartment and populate it with agressive fish--"fish that eat other fish".  He was so psyched about it.  I couldn't help but be equally excited, but also somewhat suspect about the feasability of this endeavor.  Either way, it got my mind going.

Nate has a similar effect on me, too.  He has an idea a minute.  Perhaps one day he'll settle on something, but for the moment, he remains the Wile E. Coyote of Silicon Alley--always working up blueprints for something big.  You can't help but get the wheels turning when you talk to Nate, even if you totally disagree with him, because you're going to wind up exploring the idea and learn something along the way--or take something away from it that could help you with something completely different. 

These are the kinds of people I go out of my way to spend time with.  I probably take about three meetings a week with people who have inspiring ideas completely unrelated to what I'm up to, because it's a mental workout for me.  It helps me think better and gain perspective about my own ideas--a rigorous cerebral exercise.  What I was trying to explain to my students is that, if you're going to make a living off of your creativity and innovation, you need to set your life up in such a way that you spend more time with people who inspire you to think, as opposed to just spending your time with whoever lives on your floor, or the people next to you in class.

Along the way, we've all met pretty interesting people in passing, but we don't always stop them and demand more of their time.  That's active management--making a point to be more deliberate in our scheduling, and its something we all should do more of.  When's the last time you had a really inspiring conversation with someone?  Who was it?  What did they make you think about?  How likely is it that you'll talk to them again soon?   Perhaps you should ensure that happens sooner rather than later by asking them to grab coffee or something.  My life is filled with what I call "onesies"--people not really connected to the rest of my world but that I've pulled in because my interaction with them really lights a fire for me.

Who does it for you?  Why don't you drop them a line...

"charlie, can't believe someone took your bike.   Hopefully they'll crash into a wall."  -- Plugoo message left by my mom.

Perfect storm: I just started teaching my entrepreneurship class again at Fordham this semester, @shakeshack is tomorrow, I'm raising capital for Path 101, dodgeball and softball are starting up for the fall again...    but no worries.  No blogging hiatuses.

I had a VC ask me today how I have the time to blog.

It's 11:41PM right now.  I'm in the office, and I'm blogging.  I make the time.

Can't wait to bike home tonight... it's such a nice night out.

Last night, I stopped to see my friend Amy on my way home, because she broke her ankle.  She's been pretty shut in over the last few months.

This is the x-ray of her ankle.  You can actually see the faint lines of where she broke it, in two places.  One break is right where the leftmost screw starts the grooves, just to the left of it... and the other is midway between the bottom two screws on the right.

Anyway, I locked my bike up in front of her apartment, but not right in front of the doorman, because there's construction and no place to put it in plain sight.  I was maybe there for about an hour and when I came back, the bike was gone and all that was left was my broken lock and chain. 

I wasn't that bothered by it actually.  I never spend more than $250 on a bike, because I assume it will get stolen every two years or so.  This one I got three years out of.  Tack on the $200 of various accessories and maintenance I did and I averaged about a $12.50 a month cost.  That's pretty good, considering all the train fare I saved--definitely came out ahead.

So now I'm in the market for a new bike.  I definitely want something lighter and taller than I had, and mildly considering a single speed bike, but the ones I've seen are a bit hard on the suspension or seem not to have any at all.  

So, if you know anyone selling a used bike that would fit a 34" inseam for $250 or less, please let me know.

Its been at least a week since I've taken the subway to work. I'm leaving for SF tonight and so I'm wheeling a small piece of luggage around with me. Tonight I'll be participating in the logistics olympics, trying to play a softball playoff game at 6:30, leave by 7:40 from 148th/Riverside and be at JFK for a 9:10 flight. As long as there are no major hiccups, I should be fine--especially for August. Hopefully we put enough runs up early that I can leave 10 minutes early.

Today will be research day at work... I need to put together a clear and consice picture of what's going on in the recruiting market, what's needed, and why we're it. The nice thing is that, because it's such a lucrative market, and that it cuts across enterprises as well as consumers, it's very well covered by some really smart folks.

I thought those two people, the dirty blonde and the tan guy with the goatee, were together when they walked into the car. I guess not. Still, they're standing next to each other, hands on the overhead bar, facing out towards the window. Maybe I should introduce them to each other.

People are so oddly shaped. I'm staring down at my phone typing this and I'm noticing what is obviously my grandfather's ribcage passed on through heredity. I'm sort of barrel chested. I don't know where to go with that. I'm just sayin'.

Glen Frey just randomly came up on my iPod. This always makes me think of the Mets '86 Championship video.

What company makes all these orange and red cellephane veggie bags that all the Asians who get off at Canal St carry? Whoever it is, they have a total monopoly.

The guy next to me is reading a comic book.

This seemed like a short ride.

The woman next to me is listening to a Podcast of WNYC "On the Media". I agree with @tismoi. Very few people look happy in this car.

Kilsy just came on....hard to miss. I knew it right away. They need to make more music or tour more or do anything... very good stuff.