In my limited capacity working in the “venturepreneurial” community here in New York, I’ve come to realize that this industry is built firmly on relationships.  Countless VCs have mentioned that warm intros are the price of entry to getting in the door (cold-calling/emailing has a guaranteed 0% chance of success).  Chris Dixon has said that early-stage investing is “99% [the person] and 1% [market/idea].”  Fred Wilson, who is one of the most prominent (if not the most prominent) person in the New York venture scene, has espoused managing your own personal brand, with emphasis on your online presence.  I don’t think that these ideas apply only to the world of venture capital—in fact, I think they apply to the vast majority of other industries where there is any element of human interaction.

So what is the take away?  In business that is largely opaque, it’s easy for a few bad apples to spoil the bunch.  Stories of VCs screwing over entrepreneurs, citing “fiduciary” responsibility, bathe venture capital in a stereotypically bad light.  That being said, when it’s hard to see into an industry and people say one thing and do another, transparency, integrity and honesty go a long way.  Great examples of this are the blogs owned by venture capitalists and entrepreneurs alike.  Anything that brings greater clarity to the space makes venture capital less scary, and more about interpersonal relationships.  When I meet an entrepreneur, the first thing I do is Google them.  In the complex formula that ultimately makes a successful entrepreneur, I consider managing your online presence fundamental.  If you can’t manage your own online presence, who’s to say that you can create a successful product when so much hinges on creating traction and leveraging its online reputation.  On the flip side, if you have a thoughtful blog, your LinkedIn profile is up to date, etc. that’s a good signal, at least for me.

The same advice goes for venture capitalists.  When the landscape is mostly entrepreneurs seeking money from VCs (and rarely VCs seeking to get into an oversubscribed round), it’s easy for VCs to exhibit characteristics that will often earn them a bad reputation.  Being unresponsive or roundabout is often interpreted by entrepreneurs as negative, when that’s not necessarily the case.  As Jeff Bussgang mentioned in his book, time is on the side of VCs and against entrepreneurs—it grants VCs more information to make better decisions, but as raising money is a time-consuming process, it’s best for entrepreneurs if it is as short as possible.  But, as a venture capitalist, if you are timely in your responses and honest in your feedback, regardless of whether you invest or not, an entrepreneur will walk away feeling much better about you.  A few months ago, Mark Suster wrote a blog posted called “Don’t be a Grin-Fucker.”  I’d go further and advise not only that, but maybe just try being a stand-up person.  Give respect to get respect.

In the past few months, I’ve had the amazing opportunity to speak with hundreds of people.  Of course, every interaction is different, but the ones that stand out most in my mind are when there was no wall between me and the other party.  It’s hard enough as it is to have a candid conversation with someone.  When you factor in the whole investor dynamic, it makes things ever worse.  So when I have a conversation with an entrepreneur who respects me and respects him or herself, that goes a long way.  I think that it should be the responsibility of venture capitalists and entrepreneurs alike, as the space becomes increasingly transparent, to take the “douche” out of “fiduciary.”

Perhaps one of the most useful and simplest browser tools I’ve come across.  With the push of a button, Readability delivers a beautiful, condensed version of the text that you’re reading without the clutter of ads, banners or segmentation.  Readability was even used by Apple in their new Safari 5 Reader interface.  Definitely check it out here.

Back in March, at SXSW, Danah Boyd gave a great keynote about privacy and how large companies like Facebook and Google have botched the issue.  She basically said that privacy wasn’t even close to being dead and that users are still adamant about it.  The problem for social media companies is that privacy is a double-edged sword.  On one hand, users want more of it and it’s important to give them what they want in order to attract them as users.  On the other hand, the less privacy there is, the richer the social network can be, the more the data set can be mined and the more targeted advertisements can be (= $$$).  It’s no surprise that large companies opt for the latter.  As a result, both Facebook and Google have been hit with criticism lately regarding their eroding privacy controls, and more specifically Facebook’s plan to take over the internet.  But let’s take a step back, look at this issue on a larger scale and see how we got here.

One of the major paradigm shifts that has occurred with the adoption of social media by the masses is this large-scale marginalization of privacy.  In my mind, privacy and social media (as we conventionally know it) are two mutually exclusive entities.  The more connected I am on Facebook and Twitter, the more public my activities, friendships and interests are.  The more times I check in on Foursquare, the greater the chances of me being robbed (not really).  I also just recently got back into using last.fm after a nearly 3-year hiatus, meaning that anyone can know exactly what I’m listening to at any given moment (and how many times I’ve listened to “Party in the U.S.A.” in the past week).  But what larger implications does all this relatively harmless sharing hold?  A gradual convergence of my personal and digital lives.

Now this wouldn’t really matter if I didn’t care about my privacy, but there are a number of reasons why I should care.  People have lost their jobs and gotten robbed over this increased transparency.  Furthermore, privacy goes hand in hand with security.  Blippy had a PR meltdown the other week when some of its users’ credit card numbers were found in Google.  Facebook, with all its engineers, couldn’t prevent the chat mishap yesterday.  All of these horror stories scare and drive away users, which is why it is essential for up and coming social media companies that leverage semi-private data to keep their data on lock (Mint.com did a great job of this).

Two hot trends right now—geolocation and mobile payments, deal with very sensitive information.  If you asked people 10 years ago, they would say that their exact whereabouts, their credit card numbers and their purchase histories are absolutely private information not to be shared.  So it’s no surprise that companies like TopGuest and Offermatic will have some adoption hurdles to jump over if they want to reach a critical mass of users.  Foursquare took just over a year to reach a million users, and I’ll be curious to see if they will match the accelerated user growth that Twitter saw.  The bottom line is that every new social media company is upping the privacy ante.  Facebook started out innocuously enough when your parents started friending you, but then Twitter blew the doors off of transparency and no 140 characters were sacred.  Now, companies like Blippy and Foursquare are pushing the boundaries of people’s comfort zones of sharing.  The most important thing to keep in mind is to not be too far ahead of the adoption curve.  It’s the difference between Apple’s iPad and Apple’s Newton.

I look forward to the day when all of our data is archived and managed by a benevolent company (I can dream, right?).  With each step we take in that direction, there are explosions of business opportunities and innovations (helllooo local business advertising).  But it’ll be a long road to get there, full of mishaps, bungled launches and PR disasters.  Advice for those brave social media companies planning to explore this final frontier of privacy: The less your early-adopters have to worry about their sensitive information being leaked, the more they’ll be willing to join.

Crowdsourcing is one of the many great things that have evolved and from the connectivity provided by the internet.  The most salient example is probably Wikipedia, a pinnacle in crowdsourced intelligence and proof that sometimes, the crowd is smarter than the individual (contradicting that timeless quote by Agent K in Men In Black: “A person is smart. People are dumb”).

One of the more interesting prospects of crowdsourcing, for me, is design.  Why?  Well because it’s so hard to come up with good design in the first place, but everyone has the capacity to judge it.  All you need is one person in a crowd to come up with a good idea and everyone else can rally behind it (and they will if it really is a good idea).  A great example of this is the t-shirt website Threadless.  The company is 10 years old, which is basically ancient in internet years.  The founders, Jake Nickell and Jacob DeHart had the genius idea of allowing people to submit their own t-shirt designs for the community to vote on.  The highest rated shirts would be printed by Threadless and put up for sale—and would inevitably sell out because the demand was already there.  It’s a beautiful business model that makes perfect sense.

It’s strange that it’s taken so long for the same idea to permeate into other areas of consumer products, but it’s starting to happen.  Quirky is basically a crowdsourced MoMA store.  Prospective customers “buy” submitted products, which are manufactured once a certain number of orders are filled.  Quirky just closed a Series A round last week for a cool $6 million from RRE Ventures, Village Ventures, Contour Venture Partners and Lowercase Capital.  The founder is Ben Kaufman, who was behind the insanely successful crowdsourced iPod “Mophie” accessory line (acquired by mStation in 2007) and the less successful crowdsource  startup Kluster.

Another promising company (just because I love design) is MyFab, a Chinese-based furniture company that is expanding to the states.  They’re not exactly crowdsourcing the public, but they are eliminating the middlemen between manufacturers and consumers, allowing you to effectively browse a factory’s catalogue at deeply discounted prices (and based on Groupon’s recent $1.2b valuation, we all know how valuable discounted prices are).  The more interesting part of MyFab’s site is their voting page, where you can vote on designers and effectively choose which products MyFab offers next.  If you think about it, it’s pretty genius, because there are so many factories out there just waiting to pump out products with pre-established demand.  If MyFab can carve a niche out for itself as an online IKEA of sorts, it has a very bright future ahead of itself.

Two other crowdsourcing startups are Kickstarter and FashionStake.  Kickstarter is crowdsourced funding for cool projects where investors get gifts from the investees and money is only transferred if a fundraising goal is met.  Some Etsy-established fashion designers have used Kickstarter to help fund their own lines, which I think fills a gaping funding hole in the fashion world.  That hole is what FashionStake is also aiming to fill, where people crowdfund designers in return for credits that they can use on the clothes that eventually get produced.  It would seem like this is a no-brainer business model (like Threadless), but moving past t-shirts gets infinitely trickier, in my opinion.  But if they can curate the designers and collections well, they could be a sort of crowdsourced Gilt Groupe hybrid beast—and I could see that being very successful.

All in all, I think that the implications of crowdsourcing are very exciting when applied to design (there are already sites like crowdSPRING and Rent A Coder for services).  Anything that can provide me with better designed products at lower cost is a winner in my book.

As connectivity and transparency increases rapidly on a global scale, proliferated by the internet, we are experiencing repercussions in all areas of our lives.  Facebook, Twitter, Foursquare and all other social media outlets are quickly merging our real lives with our digital ones.  But there are some corners of the internet where anonymity, one of the web’s core tenants, is still cherished.  Though it has come under more fire recently in many forms—anti p2p movements, fights against illicit activity and internet predation—the most recent incarnation may be the most important: the fight against WikiLeaks.

WikiLeaks is an internet-based organization that offers whistle-blowers a place to submit and publish sensitive documents (governmental/corporate/organizational/religious) while remaining anonymous.  Contributors’ identities are kept secret by bouncing the original submission from user to user within the WikiLeaks network, similar to how Tor works.  The reason why WikiLeaks is such a game-changer is that right now, national laws against libel, gag-orders and injunctions have no jurisdiction over post-national entities like WikiLeaks.

As you might expect, WikiLeaks doesn’t have many fans in the sectors that it acts to shed light on.  They are holding approximately 1.2 million documents and have already published a number of notable leaks including a copy of the standard operating procedures in Guantanamo Bay, information about the Peru “Petrogate” oil scandal, the membership list of the far-right British National Party, and the Minton Report on toxic dumping in Africa by commodities giant Trafigura.  A number of pieces have been written in the past few weeks covering the Pentagon’s targeting of WikiLeaks due to possession of a decrypted video showing the alleged killing of civilians via airstrikes in Afghanistan.  The video is slated to be released tomorrow, April 5th.

Although the war over WikiLeaks is certainly worthy of attention and support (feel free to donate to WikiLeaks—they need it), the ramifications of this issue are far more expansive than a singular website.  In this video interview, WikiLeaks editor Julian Assange talks about the two different roads that journalism can take.  One path is that of censorship and control—taken by China and Iran where the solution to those pesky investigate journalists is massive firewalling and policing.  The other is where free press trumps injunctions and gag-orders and transparency is the name of the game.

The argument against the first option is relatively simple and compelling.  Anyone who wishes to avoid an Orwellian-like society ought to know that as soon as the government controls the media, it is just one small step away from realizing those nightmarish scenarios.  Take North Korea for example: one doesn’t have to be a libertarian to argue that once propaganda and press are synonymous, civilians are more susceptible to brainwashing.  Moving away from the totalitarian North Korea, a more salient example is China’s censorship laws and Google’s recent decision to pull out.  Another example of government control over media is during the Iranian elections and subsequent protests, where the government prevented syndicated news sources from publishing anything about the protests and bloodshed.  People turned to sites like Twitter in order to report news from the front lines of the protests.  As journalism evolves along with the internet, oppressive regimes will attempt to control each outlet in an ongoing game of whack-a-mole.

The argument against freedom of the press rests mostly on the issue of national security.  The leaking of sensitive information, say troop movement or patrol routes, could lead to people getting killed.  Information with even larger repercussions like nuclear codes or weapons research projects is more aptly categorized as espionage.  But these arguments don’t hold water in the debate over WikiLeaks and investigative journalism.  These organizations are attempting to expose corruption and undo cover-ups, not release national secrets.

As the world converges to the point where a decision must be made about anonymity, censorship and freedom of the press, we need to make a concerted effort to preserve the independence of journalism and reporting—otherwise we might not have anything to read on our fancy next-gen iPads.  To the governments and corporations that look upon WikiLeaks with anger and fear, I’m reminded of Google CEO Eric Schmidt, who said, “If you have something that you don’t want anyone to know, maybe you shouldn’t be doing it in the first place.”

UPDATE: WikiLeaks has released their video of the airstrikes.  It’s bad.

(image from wikipedia.org)

I just ate this for my birthday lunch.  It’s a Triple Shack Stack from Shake Shack (3 cheeseburger patties and 1 deep fried portobello mushroom injected with melted muenster cheese).  When I ordered it, the gentleman at the register called back to the kitchen, “Can we make a Triple Shack Stack?”  This was met by looks ranging from awe to horror, but with a unanimous “Yes!”  Ringing it up was a little more difficult, as the computer system was not built to enter such a behemoth (Double Shack Stack + Cheeseburger was the solution).  All in all, it took about 20 minutes to eat and I highly doubt I’ll eat anything else for the rest of the day.  I’m also pretty sure that I’ve discretely reduced my number of future birthdays with this meal.

Two days ago, I got a chance to visit the month-old HQ of Diapers.com in Jersey City.  It was very easy to get to (one stop on PATH from WTC) and the new space was enormous.  It’s hard to believe that they’re already trying to find more space in the building, but at the rate Diapers.com is expanding (fastest growing retail company for 3 years in a row according to Inc.), I’m not surprised.  This post is intended to be sort of a half-year follow up to the WSJ post in October of last year.

To give this post a little context, a couple weeks ago, Josh Kopelman wrote a thought provoking piece on the state of eCommerce and how the top 15 trafficked eCommerce sites are virtually the same as 12 years ago (except for NewEgg).  He noted how surprising it was that none have changed and said that “we’ve seen more innovation (and potential for disruption) in eCommerce in the last 10 months than we have in the last 10 years — with group buying, demand aggregation, game mechanics, flash/group sales, leveraging the social graph for customer acquisition and mobile.”  One thing I will point out, though, is that Josh was using the top 15 most trafficked eCommerce sites, not based on revenue or profitability.  For example, Overstock (ranked #9) posted $834 million revenue with net income of -$12.7 million (yes, negative) in 2008.  In contrast, Zappos.com had $635 million in revenue with a net income of $10.8 million in 2008.

This past Sunday, Sarah Tavel wrote an interesting post about how innovation in eCommerce is coming in the form of customer service.  STELLAService ratings of online customer service reveals that the top overall list is different from the trafficked rankings:

Everyone’s heard of Zappos and most aspiring pre-MBAs have read the case study about Tony Hsieh and the legendary practices within the company.  Customer service is their forte—just check out some of their recent commercials which feature actual phone calls.  Another key aspect of Zappos is returning benefits to customers (i.e. free return/rush shipping).  However, the ironclad golden rule of “marginal customer acquisition cost” < “customer life time value” (LTV) holds true, no matter how many bells and whistles are attached to the business.

Judging from the explosive revenue growth (3,473.8% from 2005 to 2008), Diapers.com is doing something—a lot of things—very, very right.  Their customer service is equally legendary, to the point where those who call in and speak with a customer service rep have a higher LTV than those who don’t.  They’re even wondering whether a self-help online customer service module might drive down overall loyalty and LTV if it drops the number of customer call ins considerably.

One great advantage Diapers.com has is their customer base (and prospective customers).  Expecting parents and recent parents are a tightly-knit, sharing community no matter where you live (think baby showers).  New grandparents pass down tips and pointers to their children on parenting.  When a recent parent discovers how wonderful and easy to use Diapers.com is, he or she typically wants to share that with their friends and network.  The subsequent word of mouth coefficient and velocity is very powerful—a recent awareness study reflects a significant percentage of mothers in Manhattan know about Diapers.com.

Diapers.com is expanding so quickly that their most pressing limitation is actually physical space.  Already taking up an entire floor at 10 Exchange Place in Jersey City, they’re looking for more space in the building.  They’ve also recently leased one of the larger warehouses in Pennsylvania to help expand their operations (using Kiva Systems, which also deals with Zappos, Staples, Walgreens and Gap).  Their warehouse locations allow them to ship overnight to the majority of the country, with 2-day shipping everywhere else.  Interestingly enough, first-time customers in next-day zones who order on Saturdays (and don’t get their orders until Monday) exhibit similar loyalty and LTV as those in 2-day zones (read: less).  Returns, of course, are free, no questions asked.

To give you an idea on how Diapers.com and Zappos.com match up with each other, their respective revenues 3 years out of the gate are $89.4 million vs. $32 million.  Four years out of the gate, Zappos posted $70M in revenue, meaning that Diapers.com has leapfrogged an entire year over Zappos’ growth trajectory.  In addition, Diapers.com deals with a product that has a much faster refresh rate than Zappos (how often do you run out of shoes?), driving per year purchases up along with customer loyalty and LTV. 

Considering that Zappos was acquired by Amazon for $1.2 billion last year, Diapers.com is well on its own way to becoming what Mike Maples might call a “Thunder Lizard,” minting quite a pretty penny for investors: Leonard Lodish, Nicholas Negroponte, BEV Capital, Bessemer Venture Partners, Accel Partners, New Enterprise Associates, and MentorTech Ventures.  Everyone else just soiled their… well, pants.

My college roommate, David Haber, started his own blog here.  He just wrote a pretty interesting post on the potential future of the (indie) music industry.  His main thesis is that with the barriers to entry coming down for both the VC and music worlds, a sort of Y-Combinator for bands might prove to be as effective in grooming/selecting big hits.  Read the full post here.

ATTENTION: This is a collaborative re-post from Brad Hargreaves’ blog.

Lots of you enjoyed my post a few weeks ago on buzz and fund size among NYC venture firms. But why not take it further? Why not use all the data in Crunchbase of financings of NYC companies over the past five years?

So that’s what we did. And we got data for 814 venture financings since March 2005 worth a total of $3.1 billion. We were careful to exclude angel and strategic investors, since data around those deals are poor and would make the results harder to parse.

To start, let’s look at all venture firms that have completed over 7 financings of NYC-based companies in the past 5 years. Here, you can see how they stack up based on number of deals done:

Keep in mind that there’s a long tail here — this chart represents 300 total financing events, only 37% of all the venture financings of NYC-based companies in Crunchbase. The rest of financings were done by other firms.

But this is just parsed by the number of financings — with no thought given to the size of the deals. Thus, let’s look at the (relative) deal size by the firms listed above when investing in NYC companies:

You’ll probably notice that there aren’t any labels on the Y-axis. In brief, I don’t trust the absolute data here. It’s often impossible to distinguish the relative contributions of investors in a syndicated deal. For example, if Union Square does a $1 MM seed deal, there isn’t any ambiguity there. But if the company’s next round is a $10 MM round syndicated among two growth capital firms and Union Square, there’s no way to really know how much each firm invested. However, it is probably safe to say that the growth capital firms do bigger deals than Union Square, since they first joined the syndicate at a later (bigger) round. Thus, the relative data is accurate, but the absolute numbers are highly questionable.

Since we selected these financings based on the zip code of the funded company’s headquarters, we can drill down a bit further and draw some really interesting conclusions. Specifically, where are funded companies? The following map looks at two factors: the number of financings in the zip code (the color of the dot) and the total amount of venture money invested in the zip code (the size of the dot):

There are certainly some surprising things here, at least to me. This entire map seems to be shifted a bit further north than I expected; are there really that many well-funded startups in Murray Hill? I also expected to see a bigger presence in TriBeCa.

There’s a lot of data here, and I’m sure there will be follow-up posts — especially as we dive into the data on the types of companies that are receiving this financing.

I’ve been thinking a lot about the mobile payment world lately and think that there’s a lot of potential in space for barcode/QR scanning and geolocation.  I wrote up a short description for an idea that I had.  I’d be interested to hear people’s thoughts!

ZIPPAY

Zippay is a mobile application that allows users to seamlessly send payments to each other (similar to VenMo and Paypal’s new Bump feature) by scanning barcodes (because we all know that it’s fun—case in point, the success of RedLaser).  Each user’s Zippay account is linked to a credit card and they are assigned a unique barcode.  Here’s an example situation:

Fred and John are out at lunch and the bill comes.  Unfortunately, Fred left his wallet at home, and his portion of the bill is $12.  No problem.  John takes out his iPhone and launches the Zippay application, as does Fred.  John clicks the “Accept payment” option and enters “$12”.  His unique barcode is now displayed on his iPhone, which Fred scans with his own Zippay app after selecting “Scan”.  Fred’s iPhone recognizes the barcode and he’s prompted with a receipt for $12.  He signs with his finger on the screen of his phone and presses “Okay”.  A copy of the virtual receipt is sent to both Fred and John’s email accounts, which are already linked to their Zippay accounts.  After the transaction, Fred is prompted with the option of linking the recently scanned barcode to a contact in his address book making future payments easier, or allowing him to make payments to John even if they’re not close to each other.

However, the real potential of Zippay goes beyond just peer-to-peer payments.  Companies can easily get a Zippay account and use employee iPhones to process customer checkouts (like Square, but without the clunky hardware).  Employees would just use Zippay to scan all of the items the customer is purchasing, creating a virtual shopping cart, and then display a barcode at the end that the customer scans with Zippay.  No employee iPhones?  No problem!  Stores can just use existing checkout lanes and have display screens show the barcodes or use receipt printers to print the Zippay scannable barcode.

An even more powerful iteration of this is allowing the customer to check out by themselves (self-checkout is becoming increasingly popular).  As a customer shops, she scan items and drop them into her physical cart, while a virtual cart is building on her Zippay app.  She can view totals, edit quantities and remove items seamlessly and easily.  When the customer is ready to checkout, they just enter the store’s Zippay information or scan the store’s Zippay barcode and voila—checkout complete!  This completely bypasses the traditional checkout lane, cutting down on average shopping times or frustrating lines, granting everyone an “express checkout”.

In addition, Zippay can combine with geolocation to allow stores and nearby businesses to push promotions to customers in real-time.  As customers build virtual carts, advertisements can change accordingly.  Shopping for clothes at Barneys in the afternoon?  Maybe you might want to know that a nearby restaurant is running a special Prix-Fixe menu tonight.  Or maybe you’re buying cereal at a grocery store and there’s a sale on milk.

Zippay stands to eliminate the online checkout process as well.  Online shopping would go normally until the checkout screen.  Now instead of customers having to set up a new account and fill in all of their information (which many people are averse to), customers can just scan the e-tailer’s generated barcode.  The customer’s stored shipping information is used to calculate shipping, and they finish the checkout right there on their phone with a receipt of the transaction sent to the business.

For customers, powerful purchase history tools allow them to track their spending.  Visualization and budgeting services (like Mint.com’s) provide detailed information about your month’s expenses.  Geolocation adds another layer, where you can view your purchases on Google Maps, and even play through your month’s expenditures in a time-lapse video.  Find a particular purchase or series of purchases interesting?  Share it with your friends with a click of a button, or even share your whole month’s bill.

Across the Pacific, in Japan, all you really need is your cell phone, or “keitei.”  You can pay by swiping your phone, which stores your credit card information, at checkout kiosks.  However, with Zippay, businesses and cell phone manufacturers don’t need to implement expensive RFID chips in all of their checkout lanes, and online e-tailers can do away with their clunky checkout systems.

Zippay stands to revolutionize the way payments are made on the go: how we shop for things in person, online or how we settle tabs between friends.  At the end of the day, Zippay just wants to make our lives simpler and easier.