This blog represents my own views, not those of my employer, Brooklyn Bridge Ventures.

Do not pitch me a story or book review for me to write about. This is my personal blog. For more info on that, see this post.


Subscribe by Email

Preview | Powered by FeedBlitz


Want to meet? 

Request a meeting by clicking this calendar...

If you'd like to pitch your startup to me, there's no such thing as too early to talk. Drop me a line at or see if I want to meet in person at






Chris Christie Should Own the Cone #trafficgate

I am stunned over this #trafficgate scandal where Chris Christie apparently caused a bunch of traffic with some fake road closures in order to strongarm another politico into getting his support.

Just stunned...  that people don't think this kind of thing goes on everyday.

And stunned that we think this is anywhere near the worst of it.  I don't know about you, but this seems like child's play compared to my assumptions around what probably happens in Washington.  

I mean, you guys have been watching House of Cards, right?

This is why all you have in Washington are fake political types--because, by the time anyone reaches that height, the only people left standing aren't the best people, they're the best at playing the game.  They aren't the people who accomplished the most--they're the people who avoided headlines and never get their hands dirty.

Well, maybe we could use a guy who gets his hands dirty and says some things he shouldn't now and then.  It's not like the current system works.  Wouldn't you want Obama to cause some huge traffic jam in Utah right now over their reversal on gay marriage?  What if, instead of having to curry favor by overspending on other people's pet projects, we could just settle this with traffic jams?   I'd love to see someone cause a few traffic jams in Republican districts.

If I were Chris Christie right now, I'd seriously consider owning this, because the media is never going to let him forget it otherwise.  They were dying to cast him as Tony Soprano--the fat guy from Jersey who breaks a few bones now and then.  Now the story is that an ambulence was delayed because of the traffic jam.  Didn't you know where it was going there?  The fat bully from Jersey kills people!  They tried to do that with Citibikes.  Same story.  Citibike racks caused a delay in getting a patient out of a building--bike sharing kills!!

That's what the media does--and boy, do we eat it up.  Christie Christie is now the mafia.  You don't want to elect a mafia president, right?

I dunno.

Maybe things would... actually get done.

If I were Chris Christie, I'd say, "Yes, I'm a fat guy from Jersey and in addition to causing traffic jams, we occasionally put horses heads in people's beds and send fish.  Sometimes, we get other politicians on board through fear and intimidation and that's how it works.  You don't like it, but does it really surprise you?  If you would rather pretend that we live in a world of puppies and rainbows, where politicians just work find ways to work together for the greater good of the people, cast your votes elsewhere the next time I'm running for something.  I want to live in that world, but that's just not reality.  You either play tough or you sell out.  Most politicians are sellouts.  If you'd rather someone build coalitions by agreeing to spend money on other people's pork projects, then I'll never be your guy.  Did we cause a traffic jam?  You bet your ass we did.  Am I sorry for it?  Not one bit.  Chris Christie is a guy not to be fucked with.  Elect me president and North Korea will experience the worst traffic jam you've ever seen."

Instead, he's going to deny the whole thing and lie to our faces.  Any hopes of putting a real person in office, not that I even supported him, will be dashed and he'll just become another huge empty suit playing the game.

Did I mention I could never ever get elected to any political office? 

Local Schwag Bearers

Stick around long enough in a big tech community and you'll see your share of big company evangelists come and go.  They're always hired with the best of intentions--someone meant to be the eyes and ears on the ground for a company trying to turn today's future stars into tomorrow's big customers.  They support entreprenership because they see the ROI: Be helpful to a startup now, be there when they're high on promise and low on cash, and you could be the platform that the next Facebook runs on for a long time to come.  

They want someone who can be a friend to startups--someone with a great network, knows everyone, knows product, technical evangelist... someone who can win over the VCs, the CTOs, create content, etc. all at once.

In other words, a unicorn.

The best evangelist I've ever seen is John Britton when he worked at Twilio.  All he had to do was hangout at hackathons and do demos where he wrote code live.  It was simple and brilliant all at the same time.  I feel like NYC knew Twillio because NYC knew John.

That's great, except that when John left, Twilio seemed not to be top of mind anymore.  It wasn't clear that he had put lasting structures in place that would survive past his own association with the company.  

I mean, what do you want him to do, everything?  

Someone like that would make a great role player on a team of extraordinary part-timers, organized by someone who is just that--an organizer.  Someone who could define roles, identify players, and put protocols and manuals in place--so that when your hacker-in-residence leaves, you know exactly what their day to day responsibilities where and you can easily slot someone else in, give them goals and deliverables, and not miss a beat.  

I think big companies (and sometimes VC firms) invest too much in personalities when a big personality or someone with a big network should be used more like a tool than a centerpiece.  Plus, you can't really get one of these folks as a centerpiece forever--because they're unlikely to want to say at a big company for long.

Here's what I think a local evangelist should do for you:

1) Work you know they have other reasons to meet with people besides pitching your product.  That makes their role in the community more authentic.

2) Write a bunch of manuals on how a team of on the ground people is supposed to work, what their jobs are and *especially* what their deliverables are.

3) Go find best-of-breed specialists and hire them, also in part-time roles... a content producer, a technical person who knows your product and loves it, an events manager, etc.

4) Introduce your organization to people here, so that they're not the front person and they don't leave with all your contacts.  

5) Set me up with free event space whenever I need.*

* Just kidding**

** Not really.


Don't Read the Manual, Write the Manual

One of the hardest thing I've had to do as the sole founder of a venture capital fund is bring on help.  I'm not adding partners.  No, I just need a little administrative help here and there.  I found someone great to work with, but it's been slow going to offload things. 

Why?  What's the holdup?

It's the same thing that gets in the way of most people's ability to delegate.  If you're doing everything yourself, there are a million little tiny things that are completely necessary to getting the job done that are in your head.  You can't ask someone else to book a venue to run a Meetup unless that person knows who the contact person is.  You know who they are.  In fact, you just DM them when you need space, so the first time you have someone make that ask, it's going to take like 5 times as long.  You'll need to build up a list of venues, list of contacts, their contact info, and maybe even a form note for the ask.  It is work that no one has time for, but if you don't do it, you'll never get it off your plate.

One of the things I'm having my assistant work on together is writing up operating manuals--and it's something you should give as the first task to anyone who works for you.  This way, ideally, you'll never have to do it again in case they leave, or you add on new people.  Having a great set of operating manuals makes a small business much more scalable and resistant to natural employee turnover.  Everyone in the company should be recording exactly how they do their job.

Startup people don't like to read manuals, but they should all be dilgently writing them.  

Get Off My Lawn! Crazy Kids and Their Sex, Drugs and Startup Advice!

There is nothing I've ever written that makes me feel older than this post.  

"Get off my lawn!"

That's what this post is going to sound like, but I think it needs to be said.  There are too many people giving advice who have been through one or two startups, none of which grew into a huge company, got to profitability, or an IPO.  I think we all need to be a lot more discerning about where advice is coming from.  The startup world, which is supposed to be tolerant of failure, rarely admits when failure occurs.  We sugar coat everything and we're so super supportive of each other, we never hold each other to a high standard--making the difference between real success and mediocrity nearly indistinguishable.  

How's anyone supposed to figure out who to actually learn from?

For example, as an investor, I've never invested in a company that has gotten to an IPO or a billion dollar exit.  I can't tell you how to do that.  If that's what you're counting on to learn from me, I'm not your guy.  I'm very conscious about what I've done and what I haven't done.  I'm good at finding early winners and helping them get up and off the ground, but I've never sat on a board for seven years through all the ups and downs to be around to see a 500 person company ring the bell at the stock exchange.  

That's why I'll probably hang around the Canary board a little longer than I would otherwise--to learn from future later stage investors as the fast growing company, now around 20 people, grows over the next few years into a powerhouse.

That doesn't feel like the perspective you get from a lot of advice givers these days.  A founder will raise one party round worth of seed money and they'll go teach a class on how to raise venture capital.  A BD person at an aqui-hire will write a book on the art of the deal.  Growth hacking?  Don't get me started.  Everyone's an expert there with a participation trophy to prove it.

It's fine when you advise people on how to get hired at a small startup, because you did exactly that, and probably talked to others in the same position.  Your advice matches the experience of your accomplishments.

But, managing your career?  You haven't had a career yet.  

You're like 25.  

Yet, it all sounds like awesome advice to other startup people--i.e. other 25 year olds.  These represent the bulk of the people commenting, retweeting and liking your posts and sending it viral.  They're the ones showing up to the classes you teach.  Sometimes, it's good advice.  A lot of times, it's horribly misguided, but they'll probably never understand why.  

That's because a lot of people don't respect or understand the difference between levels of success.  Really successful rocketship riders are often pretty heads down about it.  There were tons of people early at eBay or Amazon or Google who worked there for 10 years and had a stratospheric ride up into key positions in the company.  They grew with the company and flurished as they learned how to be managers.  They'll probably disagree with a lot of what you said about startup careers, but you'll never hear from them.  

While what you've done feels successful to you because you're at a startup that has gotten a lot of early downloads for a free app, there are other people who are really hitting it out of the park that possess knowledge and insight that you don't have.  Yet, you're out there like you've got it all figured out--you and your PR startegy webinar on how to get covered in Techcrunch while your competitor is getting interviewed on ABC News.

Take this guy, Alex.  Alex writes a blog about giving things up.  It's funny and entertaining--and generally worth reading for fun.  

Alex got fired from his startup job.  Not as funny:

"I joined the company eight months ago when it was just three guys with laptops, and I’d watched it successfully launch, raise $3.7M in funding, and expand from 3 employees to 13—three of which I’d recruited and hired. I was proud of my first 8 months at work. I ran a viral email campaign that signed up a person a minute for the week preceding launch, and then generated a firestorm of media coverage when the product opened for business. Shit, I had just released a new version of our website two days prior that improved on-site conversions by 400%.

What happened?

It’s painfully simple. I excelled at the company’s growth stage because I had a ton of hustle, a lightening fast ability to learn, and the entrepreneurial wherewithal to juggle 30 skills at once. Now, the company had blossomed, hired a new VP of Marketing with twenty-five years experience, and had reached a point where it “needed specialists instead of generalists.”


So... the way in which he fell short was that he was so awesome that he helped the company grow to a point where it didn't need him.

This is like when someone asks you for your worst quality and you tell them that you're too much of a perfectionist.

He then goes on to dole out some career wisdom:

"I would go so far as encouraging everyone to get their ass handed to them along with an Employee Termination Letter at least once in their life. It’s an unforgettable feeling, and getting kicked in the gut by the unforgiving boot of unemployment is a beautiful thing. As long as you have the resilience to counter it with a roundhouse kick to the face."

What?  Try to get fired?  Umm...  I don't see how this is good advice at all.  Sure, getting fired isn't the end of the world, but neither is cutting off your left pinky.  You likely won't die from it and you'll likely be able to lead a normal life without a pinky, but that doesn't mean it's a good idea.

"You remember friends, right? Those things you pushed aside in favor of late work nights? You know, something other than your laptop’s blueish hue? I thought I did too—but after getting canned, that view changed.

After that fateful Friday lunch, I immediately started calling friends. Close friends. Old friends. New friends. Friends in high places. Friends in low places. I talked to over 40 people in 4 days. So many were unbelievably willing to help. They readily dispensed advice, made intros, and lent sympathetic ears. It was tremendously humbling"

It better have been humbling.  Who pushes friends aside in favor of work?  I'll tell you who.  Assholes.  Don't be an asshole to your friends, your family, or anyone.  Making time for others and living a balanced life would have made this nugget wholely unnecessary.  

So you only learn to appreciate your friends because now you need their help?  Last I checked, the definition of friends wasn't "people who can help you find a job."  What about what you do for them?  If someone ditched me over the last few years in favor of their job, my first response wouldn't have been to stick my neck out for them.  It would have been to ask, "Dude, where've you been?"

It's sad that it took getting fired for this guy to appreciate his friends.

"Other than being an affable goofball, there was not one thing I was best at in this last company. Our designer is a better designer. Our engineers are better coders. Our CEO is a better marketer. Our Chief of Staff is a better leader. Yes, I was very good at those things, but was I the best at any one of them? No. Painful, but true.

In other words: I was expendable. That phrase “we need specialists instead of generalists,” already haunts me. It will also be the last time I hear those words. Think I’m going to become a master in my next job? Yep. Better fucking believe it."

This is the most humble section in this post, barely.  I'm glad he aims to master a craft in his *next* job, but what he misses out is taking some responsibility for not learning how to do that in *this* job.  And was there absolutely no warning given along the way that he wasn't going to be what the company needed in the future?  Feels hard to believe that this came out of nowhere--with no opportunity given to him to step up into a bigger role.    

The vast number of startup employees at the most successful companies are totally unqualified for their jobs.  Even if they have prior experience, they don't have experience at *this* company at *this* particular moment in technology with *this* particular product.  It's all new to them and the most successful people adopt, learn, change, and grow.  

That didn't happen here and the author never asks why or holds himself accountable for that failure.  Why did he fail to see the need for new skills coming?  Skate to where the puck is going, dude.

With every hiccup I've had in my career, I've tried to make the best of it, of course, but the first question needed to be "Could I have done better?"

I got hired as a two year analyst at Union Square Ventures--as did Andrew Parker after me.  When my time was close to being up and we discussed my next moves as a firm, it just seemed like a normal transition.

When Andrew stayed longer than two years and started sourcing investments--I realized that anything short of surpassing expectations at my job was a failure on my part.  Maybe if I had been better, a transition conversation wouldn't have happened.  Just because it was only supposed to be two years didn't mean it was written in stone.

That's why, when I got hired for a one year stint at First Round to help them build a presence in NYC, I made it a point to say that my goal was to be indespensible.  It was kind of a crazy thing to say when they had plenty of east coast coverage and no partnership positions available.  Instead of one year, I was kept on for a second year and I wound up leading seven investments while I was there.  That wasn't even supposed to have been my job, but it didn't matter.  

Surpassing expectations was my job--and even then, I was still trying to be good enough for them to add on a *fifth* east coast partner.  Of course, it didn't make sense economically, but working on the things that would have made that even a consideration was still in my head.  For example, why didn't *I* find Birchbox before anyone else?  I was at that Internet Week when Katia and Hayley were networking pre-raise.  Who didn't I talk to there that I should have that would have introduced me?  Why wasn't I in Makerbot?  I knew people from NYC Resistor. 

So before you concede that you aren't a fit for something, or that some outside force prevents you from success, try being a bit tougher on yourself.  Resist putting on the spin of a happy post-mortem and be honest with yourself about what you might have been capable of had you done better.  You'll thank yourself later for kicking yourself in the ass instead of patting yourself on the back every time things don't go your way.

Changing my mind about blogging

I've been dolling out career advice ever since I walked into college with a paid internship in finance.  I seemed to know what I was doing, so lots of people asked me for help.  I spent a lot of time thinking about what seemed to be driving my career and the paths of others, because I wanted to make sure I really believed that the advice that I was sharing could work.  

I focused a lot on personal branding.  Given that fostering my own personal brand online has propelled much of my success, I certainly believed in it.  I told everyone to start a blog--and I believe that.  Journaling is a great way to make sense of all of the disparete information that gets thrown at you everyday.  A blog is also a mental portfolio for knowledge workers.  It's how I understand the thinking that you bring to the table that facilitated the accomplishments on your resume. 

There was only one problem.

Blogging is hard.

As I come up on the 10th anniversary of my blog, I know well what it takes to maintain a blog.  When I started in early 2004, very few people were blogging--and then I watched blogging take off.  It seemed like everyone was starting one.  Keeping up with it, however, proved to be a big challenge.  Eventually, people went in one of two directions.  Either they went pro, which led to publications like Techcrunch, or they just went silently into the night.  The web is riddled with dead blogs and rare is the consistant indie blogger who just writes because they like to.

Still, I trudged on with the same advice, until recently.  I came to the realization that if no one was going to take it and it was too much trouble, what was the point.  It became like the diet that advises you to stop eating everything you like.  It might work in theory, but fails completely in practice.  

Even when you do keep up with it, blogging sucks in a lot of other ways, too.  First off, it's all on you.  The nature of the platform is such that it's up to you to create all the content.  Sure, you could be a curator like Laughing Squid or Swiss Miss, but it's still up to you to find all these great sources.  

On top of that, you have to feel like you have something to say.  The act of publishing on the web feels authoritative, and a lot of people can't get past that.  A lot of people who actually do have lots to say don't want to come off that way, so they'd rather not put their ideas out there in public.  It's a loss to the rest of us, but I don't see what gets them out of that thinking.  I've told them to think about it as being a student in public, but that doesn't seem to convince them.

Plus, blog subscriptions have never really been figured out.  No one uses RSS anymore, and Twitter is kind of a substitute, but only a small percentage of your followers are going to see the tweet about your new post.  Marketing isn't really integrated into the platform at all, so it's up to you to generate your own interest.  That's perhaps the hardest thing about blogging.  You pour your heart into your writing and for a good long time, no one reads it.

That's when I realized how much more important to me another digital medium had become--my weekly NYC tech newsletter.  Don't get me wrong.  I love blogging and will continue to do so, but if I had to choose one to keep, it's kind of a no brainer.  I can easily say that the weekly note I send out to over 8,000 people a week in the NYC tech community is a far more important channel for me than my blog.  That's why, for the first time, I told a friend who said she wanted to start blogging that she should think about starting a newsletter instead.  

I gave her the following reasons:

  • When you come up with a structure that isn't just writing, curation is easier.  My newsletter started out as a pure events newsletter.  I didn't even have to write anything, and people would reply every week asking to post events.  If you start adding things like jobs and links, they'll do the same, and you don't have to do that much work.  You could have a submissions button on your blog, but that feels like a much higher barrier than having someone just hit reply.  When you curate, this takes the pressure of feeling authoritative off.  It comes off more like, "Hey, I'm just trying to be helpful by sharing this cool stuff that I found with you."
  • A newsletter works with a small group--because the readers are self selecting for being *really* interested.  An inbox is pretty personal--so if someone is going to let you in, they're going to have to find what you write pretty valuable.  The engagement statistics on my weekly newsletter blow my blog out of the water by far.  
  • E-mail is the best feed reader, especially on mobile.  Everyone knows how to type an e-mail into a box.  It's an easy sign up process and it's right in people's workflow.  Plus, over a third of people's time on their phones is in their inbox.  Compare that to how few people have actually downloaded a mobile RSS reader.  
  • You can still blog in a newsletter.  If you're curating links, you can add your own to the list when you've got something good.  I do that all the time, but not with every single one of my posts.  Link to a blog you keep on Medium.  That feels like a good place to write when you don't write that often.  You can also just post your thoughts directly in the newsletter if you'd like.  
  • Newsletters are more easily monetized.  Because of the high engagement rates and self selection of the audience, it's easier to make money off a newsletter.  I could put an ad on my blog, but who's really going to get excited about a banner on the web.  On the other hand, if you've got a message you want to send out to 8,000 people in the tech community in NYC, right into their inbox, that ad feels like a more compelling value proposition.  

Newsletters aren't perfect, though.  There are still a lot of things broken in the newsletter world.

  • Discovery sucks.  There are some really great under the radar newsletters out there and it's tough to find them.
  • Curating content is a bit clunky.  There's no easy way to get from a cool link to e-mail html.  You basically have to cut and paste everything yourself, and if you have a custom template, there's going to be some handcoded html in there as well.  Plus, there's no easy way to work the submissions process.  People ask me to post ads, but managing the text ad, the link, and the payment is full of duct tape and bubble gum. 

I'm looking into ways to fix this and business models around it.  If you write a newsletter with a strong, engaged following, I'd love to chat.