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

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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.  

How do others hear your story?

Storytelling is one of the most important skills you can have as a founder.  You tell stories to investors, customers, potential new hires, the press and partners.  The key to telling a good story, and what I find most often lacking, is the ability to put yourself in someone else's shoes.  

Who is this person and what about this story are they going to care about?  

You can, and should, tell the story of your business a hundred different ways if you're telling it to a hundred different types of people.  An investor wants to understand how this is going to make them rich.  A potential hire wants to understand why this is going to be a cool place to work.  A reporter needs this article to turn into pageviews.  Every line in your story needs to be delivered with that context in mind. 

Key to that is realizing your role.  When you get into a pitch meeting, it isn't a press conference.  It's a campfire.  The story doesn't move forward based on the questions from the audience--bobbing and weaving at the whim of the investor.  It moves because you move it.  You're walking them through, telling the story that you know will excite them.  You need well timed exclamations, pauses--it's a production, not an inquisition.  You drive.  I want to get taken for the ride of my life.  All day, people send me boring stuff--be the most exciting thing I've seen today.  Be the thing I can't wait to tell my significant other about.

If you're not literally imagining this investor opening the door to their place and tripping over themselves to tell their significant other about your company, then you're never going to capture your attention.  You need to understand why that particular person will get excited about what you're doing.  A good storyteller tailors to their audience and knows what will excite and delight them.  


Resolve to Be

Last night, at a New Years Eve party, I asked a few people if they had any resolutions for 2014.  It was a mix of the usual--get more sleep, wake up early, eat better, go to the gym, get something accomplished at work, etc.

No matter what people said, though--it all seemed kind of... well... fragile.  When you resolve to do something, so many things could get in the way, not the least of which is a change of priorities.  Maybe running a marathon isn't going to be nearly as important to you by the time November comes. 

That's why instead of resolving to *do* anything, I'm thinking about the ways I could resolve to *be*.  I may or may not break 2:30 in my triathalon, but I can be more attentive, be a better friend, be more organized, more thoughtful and more curious.  

Goals about what kind of person I want to be keeps me focused on the drivers and intentions, not the results.  If you can change your intentions, it's like fixing the operating system versus changing up the apps--and everything will run closer to the way you want it to.


Paul Graham and The World Out There

There is a controversial interview with Paul Graham floating around and I'm left to wonder why we're still paying attention to guys like him.  He is accused by people of being, at best, oblivious and at worst, sexist.  I've never sat down with the guy, so I can't speak to that, but I'm tired of hearing about the same voices over and over again when I'm not even sure they're relevant.  

Why give more airtime to someone whose peak of influence, and perhaps success, is clearly behind him--especially to talk about topics where he clearly isn't adding value to the conversation.  Every time he opens his mouth about founder diversity, he seems completely out of his league to address the topic.  I want to hear Paul Graham's thoughts on gender equality and inclusive participation in the Valley as much as I want to hearCharlton Heston's thoughts on gun control.  

"God knows what you would do to get 13 year old girls interested in computers. I would have to stop and think about that," he offers.  

Clearly he's never heard of littlebitsGoldieBloxRoominate, or Hopscotch--not to mention Codecademy [EDIT: Codecademy is a YC company, so duh on my part] or Makerbot.  

Well, maybe he should do that... Stop--AND think.  As a guy, I know how hard it is for us to do either of those things, let alone do both at the same time.  However, in this moment, I think one's career in venture capital depends on changing your perspective.  

The biggest question I think VC's face right now is whether or not, in the future, the best founders will look and act like the best founders of the past.  Will they come from the same places as today's industry leaders, or from the far corners of the earth and from underrepresented groups?  The world is getting flatter than ever before and the white American male is exerting less and less influence over it each day.  

If you are a venture capital investor and you're not preparing yourself to succeed in a more diverse ecosystem of entrepreneurs, you're just going to get left behind.  

Considering the myopia at the top, it's not surprising that turning point may have already happened for YCombinator.  YC's best investing days may be behind it.

YCombinator had a great run from 2007 through early 2009 investing at a time when there weren't nearly as many seed funds and accelerators as there are now.   They picked up Airbnb, Heroku and Dropbox. 

Since Airbnb, however, it feels like not only is YC missing another billion dollar plus home run, but the percent of companies worth $40 million (a standard YC has used in the press), either by financing or exit, seems low.  I'm thinking maybe I found about three dozen companies worth that much in the nearly 400 companies that have been through YC since Airbnb.  That's less than 10%.   The classes got too big and quality was diluted because, by PG's own admission, YC "grew too fast."  

You could argue that the recent companies are too early, so I'll take that challenge and compare it with my own portfolio.  Given that they do $17-20k per founder across 350+ companies, we're in the ballpark of the amount of money we're invested--just south of $10mm.  

My own track record as a VC across First Round Capital and Brooklyn Bridge Ventures actually starts in January of 2010, *after* the Airbnb class of Winter 2009.  I've closed on about 20 early stage investments and, by comparison, 5 of my investments are now worth $40 million or more either via financing or exit (with three more over $25 million).  That's 25%...  a far higher rate than YC has appeared to have done since then.  My total valuation multiple across that span is nearly 4x and the return rate is up over 110% IRR.  The initial base of capital has already been returned in those investments, so it's not a made up return based on just paper gains either.

Most relevant to this conversation, though, is that I didn't do it by only funding only hacker dudes in the Valley:

  • Nine of my twenty investments have female founders or co-founders--nearly 50%.
  • All of the companies but one were funded in NYC, with the other in Boston.  
  • Of the 20 teams, only half count an engineer as a founder or co-founder.

A couple of years ago, I went to a networking event sponsored by a top tier VC firm.  It was held at a trendy Lower East Side bar where the price of the drinks made it the kind of place that a typical NYC entrepreneur would never actually go.  The invitees were a who's who of the NYC tech scene--all the most visible folks.  

It was exactly how you'd imagine a venture firm to throw a party.  You could see that conversation happening:

"Hey, let's reach out to the community.  What's the coolest place to go to?  Let's invite all the important venture and startup people people we know of--and don't forget to throw in a few women, too."

You wind up a far cry from Shake Shack when that happens, I'll tell you that.  

That's when I realized what separates how the next generation of successful VCs will look at the world.

That party was a bet that the best future opportunities would come from an insider network of people already connected to the establishment--that getting the next Google or Facebook meant connecting to the people "in here".  

I'm certain, however, that the more interesting stuff is going on "out there".  I believe that the most successful companies that I will get to work with over the course of my career will come from people not currently connected to the insider ecosystem, and from people who don't look like yesterday's notable founders.  I'm making a huge bet on the people "out there" because they have new ways of looking at things, new approaches to running businesses and are tackling problems being felt most deeply by the people outside the inner circles.  

If I'm going to be successful in that world, I better damn well have a view on how to make the ecosystem more inclusive.  I need to watch my style to make sure I appear approachable versus authoritative.  I need to learn from my mistakes where I may not have done all I could to make people feel welcome and respected--and surely I've made 'em.  

My brand needs to be one of a dutiful civil servant in a welcoming city rather than what I see from certain investors--acting like royalty in a place that investors believe is the only one that matters in the world.  

The media needs to do it's part, too.  Let's stop paying so much attention to what old voices are saying about the establishment, and instead strive to seek new voices and new perspectives.  Otherwise, we risk signaling to future generations that these are the people in charge and that nothing is going to change.  

We need to send a strong, clear message to that 13 year old girl, the 13 year old black kid, and the 13 year old growing up outside of anywhere anyone thought to call a venture hotbed to tell them that they can be successful and that they'll get the help they need from openminded professionals.

Why Floored is Awesome, and Not Just for the Real Estate Industry

The other day, I looked at some real estate on behalf of one of my portfolio companies.

The owner sent me this...




Maybe I just don't have enough imagination or lack the requisite architecture degree.  At least it's better than showing an actual picture of what the office looks like now, after the last tenant trashed the place on their way out.  Or, if they didn't trash it, they subdivided it for a colony of bees and painted it what can best be described as neon beige.  

This is what Floored does, with a turnaround time of just a few hours... 

If you don't understand the value of that to anyone who sells space, you probably also read the directions on toothpaste. 

But it's not just selling space--it's what goes inside the space, too.  Floored's technology isn't just going to help you imagine your new office or new home, but walk through and buy all the furniture, paint, flooring, etc that goes into it.

That's exciting--and I'm glad RRE and Greycroft felt the same way.  They just led a $5m+ seed round in the company.   It's a nice bump for my seed portfolio (I invested about a year ago) and a big win for the company, which is already on a serious revenue ramp.

Congrats Team Floored!