Startup Weekend NYC FTW!, originally uploaded by ceonyc.

Lotsa work going on right up to the finish.

People who actually know me recognize the image to the left as my avatar.  They might not know what it is, but they know they see it across many of my various profiles and instant messenger accounts.  It’s actually the screenshot of a Voki character that I created—a little bald dude with headphones in front of a baseball, surrounded by a fireball.  It’s meaningful to me because I was the Director of Consumer Products at Oddcast when Voki was launched.

Fred told a similar story this week about his avatar:

“I began to use it a bit here and there around the web as I set up new profiles. But by no means was it the only profile picture I used. For corporate oriented services like LinkedIn, I'd use my Union Square Ventures headshot. For social nets like Facebook, I'd use a regular headshot. I used a photo of me taking a photo on Flickr for a long time.

But then I started to realize that the Wallstrip avatar was becoming my online identity. People would comment about it all the time. Around the time we sold Wallstrip, Howard asked Jenny to do a real painting of it which I now have in my office at Union Square Ventures. It's a real conversation starter.

Sometime in early 2008, I just decided to go with it everywhere. It's at the top of this blog and everywhere else I have an online identity. It's my online brand now.”

One of his commenters agreed: “thats how i recognize the Fred Wilson brand online.”

The key here is that, by making our online interactions personal, Fred and I are creating a brand for ourselves that has real business ROI.  Followers of my blog and my Twitter account know that I bike, play softball, and kayak.  They’ll joke with me about my taste for heavy industrial music, and they don’t mind so much the occasional snark I use in my writing, because when you deal with me professionally, you get Charlie O’Donnell the person, not just the resume.

It shouldn’t be any surprise, then, that I think of my online presence as my most important business asset—and that I conduct a lot of important business through these casual and personal channels. 

That’s also why, more and more, LinkedIn is becoming less of a place of business for me, and more like a static rolodex.  At the end of the day, LinkedIn just isn’t a place where I want to spend much time.  I don’t engage in nearly the kind of interesting back and forth that I do on Twitter or on Disqus comments either on my both or that of others.  It’s just a well connected rolodex of over 1300 of my best contacts…   but in the grand scheme of things, I’d rank it a distant fourth in terms of my most important online profiles behind my blog, Twitter, and Facebook.

So when I got notified that not only had LinkedIn removed my avatar, but had revoked my photo privileges, I was pretty stunned.  They told me that “as a professional networking site” they give users the opportunity to upload a photo to assist other members in recognizing me. 

Actually, I don’t need photos to help others remember who I am—because I only connect to people that already know me… and tend to know me pretty well.  If you just saw my bald head at a conference and that’s all you have to go on, I’d rather you didn’t try to connect. 

On top of that, LinkedIn’s language of photo “privileges” and giving me an “opportunity” is a rather interesting choice of words for a site that depends on its users’ content and active use of the site to upload their contacts to produce revenue.  If anything, LinkedIn should be thanking me for the privilege I gave it to monetize my network, instead of reprimanding me for improper use of the “opportunity” it gave me like I was a child.  Furthermore, who are they to tell me what acceptable professionalism is online?  Clearly, over 1300 people find me acceptably professional.  If they didn’t, they wouldn’t connect to me.  How about removing all of the privileges of random people who don’t know me and try to connect. 

I’ve been an active user of LinkedIn for years—advocating its usage and teaching about it up at Fordham.  There are lots of things I wish it did—like helping me actively monitor relevant changes in my network or having better group tools.  One problem I did not have, nor did anyone else, was too many people putting up avators or corporate logos as their image.  It’s not a complaint you hear about Twitter—that the site is unprofessional because people don’t use their real pictures.  LinkedIn may not care about how people conduct business now online—it’s making too much money selling access to my profile to recruiters.  However, things have changed.  More and more people are gathering in more friendly, social places online around common interests outside of their career and getting more business done like that than on a buttoned up resume site.  Policing photos and reprimanding users that other users want to connect to shouldn’t be a priority for LinkedIn if it really wants to be the kind of place that up and coming professionals want to spend any time in.

Congratulations to the future Mr. & Mrs. Cuthbert, originally uploaded by ceonyc.

My best friend since 1st grade just got hitched in Central Park.

Yesterday, I bought an Xbox off of BigDeal.com, one of our First Round Capital portfolio companies. I spent nearly an hour and a half bidding against some guy to try and buy at increments from about $18 all the way to $168.  I tried every strategy I knew…  holding out to the last second to try and lull him into a sense of security and then jump in…  then brute forcing it by counterbidding every second all throughout the $30 and $60 range to try to wear him out.  It was an addictive bidding frenzy—and my downside was just buying it at the Amazon price, so I couldn’t really lose.  (I didn’t win, but I’ll be back!)

TechCrunch did a good job of covering the company yesterday, so I’ll just pull the highlights:

“BigDeal lets users purchase virtual bids $0.75 each which can then be used to bid on goods ranging from video games to high-end televisions. Whenever you bid on an item, its price increases by $0.15 and an extra 30 seconds are tacked on to the duration of the auction. With this model, items end up selling substantially below their market value. But one of the main criticisms of Swoopo was the risk of losing your money spent on bids (regardless of whether you win or not) when the auction concludes. BigDeal takes a couple of steps to mitigate this risk.

With BigDeal’s model, any users who get outbid get a full credit of the money uses for bids to buy the item via a “Buy Item Now” option (which Swoopo also has, called “Swoop-it-now”). So if you spent $10 on bids, your Buy It Now price will be dropped by $10. Of course, the Buy It Now price will frequently be higher than the price of item sold for in the auction but at least users aren’t necessarily losing money all together. And the Buy It Now price is set at the same price that Amazon lists for the same product.

That’s not all. BigDeal provides an added incentive for bids by letting all users trade in the money they spent on bids for gift cards. All users get $1 gift card discount for every $1 spent on bids. So if you buy $25 in bids, BigDeal will give you a $100 gift card for $75…

…It seems that Big Deal has taken the best elements of Swoopo’s model and added several features which make it more of a win-win for consumers. Plus, it adds information, like bidding history, to the process to make the auction more fair.”

I’ll be interested to see how the company works towards providing more and more auction transparency.  Admittedly, when I bought my Xbox, I didn’t realize that I wasn’t getting my bid points back when I took the “buy it now” price.  I thought everyone was seeing the same price, like a loaded gun on the table, and that everyone’s bid lowered it.  I figured everyone else’s lost bids were subsidizing my price, but as it turns out, I didn’t really get “refunded” my points back—they just came off the MSRP.  So, I effectively just paid the MSRP price…  not what I wanted, but not a terrible outcome, since it’s been years since I had a game system and I was kind of itching to get back into it.  Perhaps I’ll bring it to the new First Round offices in Union Square (coming this January) and we’ll have entrepreneur Madden tourneys!

I've been thinking a lot about where entrepreneurs and startup talent come out of in NYC. A lot of folks believe that you can train people coming out of the financial services base to do something entrepreneurial, but honestly, I'm not so sure about that. What I do think, however, is that it takes more than just a visionary leader or a ninja-level hacker to start a business. There are tons of startup companies in New York City, many already making money or well funded, that are looking for top supporting talent--engineers, designers, salespeople, business development pros, product managers, etc. This is where we, as the startup community, can do a better job--mining the installed base of talent in big companies. I'm actively looking for ideas on how to tell the masses of talented, experiences folks slaving away in Cubeworld that there's a thriving innovation community in New York City with lots of great companies looking for talent. How do we pick apart the CondeNasts, JP Morgans, and Time Inc's? Please talk to me about it. If you're a recovering Fortune 500 employee, tell me how you got out. (charlie@firstround.com) One way the nextNY community is trying to help is with Matchup Camp.

MatchupCamp is for skilled professionals to find new opportunities—for developers to find inspiring projects, for salespeople to find interesting products to sell, etc.  It’s not a bunch of unemployed people handing out resumes.  It’s for people looking to explore where they might best fit.  When we did this two years ago, technical talent probably made up 40% of the crowd and we’re working hard to make sure it’s not just people with ideas, but people who can make them happen.

When: December 8th at 6:30

Where: FYI Studio 22 West 27th, 6th Floor

RSVP here

Wow… what a long way we’ve come.  In February 2006, I started nextNY because the only community-wide event in town was the NY Tech Meetup and, at the time, it didn’t have much community about it.  I think I was member #71 and now it’s got over 10,000.  At the same time, the NY tech community has exploded with events, both educational and social.  One look at GarysGuide and you can get quickly overwhelmed.

A number of people asked me at recent nextNY events how they can find out about what’s going on.  Pointing a busy entrepreneur or executive to the nextNY listserv, which buzzes all day with discussion of memory caches, CMS’s, and finding a bookkeeper clearly isn’t the answer. 

Therefore, I’ve decided to take the attendee lists from the last two Shakeshack events and some recent nextNY talks and start a once a week e-mail newsletter as a curated version of what’s going on around town and in the online communities as well.  In the future, I’ll also be highlighting some open job positions, maybe some companies, and maybe just some recommendations on people that you should follow.  If you’d like to sign up for the list, just go here.  It’s going to look pretty texty and unformatted for a bit, but I’ll dress it up soon.

Event of the Week:

The Net Neutrality TechDebate, an Oxford style competitive back and forth on what is probably the most important topic in technology today that few of us have a clue about. 

The debate will be held on Tuesday, November 17th at the IAC Building, 555 W 18th St btw 10th & 11th ave.  Doors open at 7:00 PM.   **RSVP here**

The Debaters

Against

James Assey - Executive Vice President, National Cable and Telecommunications Association
Robert Quinn -  Senior Vice President-Federal Regulatory, AT&T
Christopher Yoo - Professor of Law and Communication; Director, Center for Technology, Innovation, and Competition, UPenn Law

For

Tim Wu - Coined the term "Network Neutrality"; Professor of Law, Columbia Law
Brad Burnham - VC, Union Square Ventures
Nicholas Economides - Professor of Economics, Stern School of
Business, New York University.

Can't make it?

The debate will be streamed live at: http://www.livestream.com/techdebate
A podcast will be available after the event at: http://tech-debate.com

Would rather drink? 

Check out the NYVC Happy Hour instead.

=========================================

This week is O’Reilly’s Web 2.0 Expo at the Javits Center.  By registering for an Expo Pass, you can get in free to see all the keynotes, the sponsored sessions, Web2Open, Launch Pad, and the Birds of a Feather sessions.  

Here’s what you won’t want to miss:

Monday

Ignite NYC – 5 minutes, 20 slides.  Geeks + Slideshows = Awesomeness

7PM at New World Stages: 340 West 50th Street

Tuesday

2PM: A Conversation with Caterina Fake Jennifer Pahlka (Code for America), Caterina Fake (Hunch)

2:25PM: Streams of Content, Limited Attention: The Flow of Information through Social Media danah boyd (Microsoft Research)

Wednesday

2:20pm A Conversation about the Realtime Web Brady Forrest (O'Reilly Media, Inc.), John Borthwick (betaworks)

Thursday

9:15am A Conversation with Beth Noveck Tim O'Reilly (O'Reilly Media, Inc.), Beth Noveck (Executive Office of the President/OSTP)  <—Yes, *the* President

=========================================

It’s also Entrepreneur Week and there are a couple of noteworthy panels.  Unfortunately the event is sold out, but there will be a livestream available on their site soon.

I think the pick of the conference is this panel at 2:15PM on Thursday:

The Revenue Inflection Point: The New Reality of Scaling a Business to $100MM in Revenue

MODERATOR: Bob Tedeschi, New York Times Technology Columnist

PANELISTS:

Stephen Messer, Co-Founder of Linkshare

Omar Amanat, Entrepreneur in Residence, Wharton School of Business

Marc Cenedella, Founder & CEO of TheLadders.com

Nancy Pedot, Former CEO of Gymboree & Party City

Chris McCann, President of 1-800 Flowers.com

Also right up there is this Friday panel at 10:30AM:

A Roadmap for the Entrepreneur Pt. 2: Top Venture Capitalists Reflect

MODERATOR: Murat Aktihanoglu, Founder of Centrl & Entrepreneurs Roundtable

PANELISTS:

Albert Wenger, Partner at Union Square Ventures

Jim Robinson, Co-Founder & Managing Partner of RRE Ventures

Anthony Marino, Managing Partner at Virgin Investments

Howard Morgan, Partner at First Round Capital

=========================================

This weekend is Startup Weekend.  Startup Weekend recruits a highly motivated group of developers, business managers, startup enthusiasts, marketing gurus, graphic artists and more to a 54 hour event that builds communities, companies and projects. 

David Kidder will be speaking Friday night while Nate Westheimer, Sam Lessin, and I will be on the Sunday night panel.

Last week, First Round Capital had its annual meeting, where we got to walk through our portfolio with our investors.  Honestly, I didn’t realize how many cool companies we had invested in, so I’m going to take the time each Friday to highlight another company.

Since I got a “One of Josh Kopelman’s friends likes your photo” note from Thread yesterday, that’s going to be today’s spotlight.

Thread is a pretty simple concept: Meet people through your friends on Facebook.  Now, conceptually, meeting people through social networks is a good idea—but we all know how unappealing setups can be.  Thread enables you to get proactive about searching your friends’ networks while minimizing the effort and risk they put in as a middleman. 

What I really like is the anonymizing features of the site—where someone can reach out to you, but they’re shown to you in a group.  You only get matched when there’s mutual interest.  That keeps down the awkwardness of a turndown should you ever meet in person.  For all they know, you just don’t check the site.  This works a little like those “One of your friends likes you” viral sites from the late 90’s, but now you’ve got the assurance that there’s a real human behind the interest. 

The site could do a little better job learning about my preferences and keeping me searching for more people, but overall, it’s a pretty solid concept and execution.  So, if you feel like you’ve got a pretty good network of single friends, but don’t really want to get too involved with matching people up, let the interwebz do all the heavy lifting and sign up for Thread.  You can just sit back and reap all the social capital.

[My Plugoo] [grr] how do i no if my my dog is dying
12:38 PM
[grr] she is only 4 months old
12:39 PM
[grr] hello plz i need an answer

ceonyc12:39 PM
Take her to the vet.

myplugoo12:40 PM
[grr] i done have enough money

ceonyc12:41 PM
Most vets will at least look at a sick animal for free if you really don't have enough
12:41 PM
it's worth a try... I can't see them turning away a sick animal b/c you can't pay

myplugoo12:41 PM
[grr] she breathes weird she doesnt want to move a bit and will a few days ago she took a little totsie roll out of my hand

ceonyc12:42 PM
chocolate is very harmful to dogs...you should take her to the vet

myplugoo12:42 PM
[grr] i should

ceonyc12:42 PM
Yes... worry about the money later

myplugoo12:42 PM
[grr] ok thx

ceonyc12:42 PM
no prob

myplugoo12:42 PM
[grr] will bye

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.

I just got off the phone with an entrepreneur that hit all the right points… 

- Followed up on a small idea to figure out if there were any customers for his service—turned out there were more than expected.

- Worked with other startups to figure out proxies for the set of most demanded features and compatibilities—and made a plan to offer them. 

- Got up and running right away—and on the cheap—to start testing the service.

- Crashed the service several times with early alpha users, leading to improved product.

- Almost as immediately, went out and started talking to all of his potential competitors, finding out where this service was on their roadmap.  Even found a way to derisk competitive threat by thinking about ways to work with them.

- Now that he’s done research and has initial customer validation, he’s raising just enough to get to the next milestone—to figure out what his business strategy will be out of a limited set of scenarios that he’s narrowed down to.  This will be dictated by real metrics like cost of acquisition, sales cycles, margins and capital requirements.

Color me impressed. 

A lot of times, when I see a startup’s advisory board, it’s a skippable slide.  You’re a vertical search for Play-Doh and you have some guy that owned a toy store for 20 years as an advisor.  That’s a yawner because their are probably 50,000 people just like that guy around.  It’s nothing special to get him involved, and while he has some domain expertise, it’s not so unique that he gives you an innate advantage—nor can he get you any doors opened that you couldn’t get yourself.  Now if you had the inventor of Play-Doh or the Chairman of the Play-Doh corporation, that would be something, because now you’re talking about people who have relatively unique experience and the ability to command unparalleled influence and respect in the market. 

When I first started Path 101, I made a list of who would be the ultimate people I’d like to get involved in the company as angels or advisors.  The founders of any of the big job boards were tops on that list, so I immediately looked up what they were up to now and did my best to network my way to at least a conversation with guys like Richard Johnson, who was the Founder of Hotjobs. 

That turned out to be important, because the more people I talked to in the jobs space, the more people wound up asking me if I had ever spoken to Richard and what he thought of the company.  Had I answered that I had never met him, that would make it seem like I didn’t have the ability to make the connections I was going to need to push the company forward. 

Investors do that all the time.  They leverage their network for second opinions and to try to provide help to portfolio companies.  I’m often sending companies that I meet to the best networking contacts that I can think of—but in reality, even though it rarely happens, I’m always thinking that the folks I send them to are connections the company should have already made. 

So, if you’re a startup in the fashion space, you should have already talked to the founders of Gilt—and actually that’s probably where I should have gotten the recommendation to meet with you in the first place.  When successful industry folks send me a company, in a way, it already derisks the competition question.  It means that the big gorilla in a space probably doesn’t initially see you as competitive, but that you’ve got something that people who should know what they’re talking about believes will get you to success. 

So who’s your ultimate “Who’s Who?” list of people you’d like to get involved in the company either as advisors, investors, or just champions?  Don’t wait until you raise money or even have your product launched to have a dialogue with them.  They’re undoubtedly the best people you can possibly get feedback from on the viability of your idea, what the customer pain points are, and what will sell in your market—and whether or not they might ever want to buy you or eat your lunch.  I’m going to eventually go to them anyway for due diligence as well, so best that they know and understand your story firsthand—and that you’ve sold them on it.  Also, if in fact you do get them on as angels, it provides the company with a nice validation on the market side.

So who’s who?

Here’s a list of the types of people you should be checking off:

• CEOs of companies that you want (or need!) business development relationships with
• CEOs of companies that you’re in possible competition with (Hey, you never know)
• The very top of the heap of pundits and thought leaders in your industry, including top industry analysts
• Financial backers of the most successful company in your space
• Original founders of the most successful companies in your space

Also, convincing top industry folks to champion your cause should conceivably be a helluva lot easier than driving $10 million dollars in revenues or signing the business development deals that will get your product the distribution it needs.  If you can’t sign up an advisor to a deal where they get a little equity in your company for a quarter call and a quickly returned phonecall, how are you going to ever hire that rockstar developer away from Google or sign that tipping point deal?  It speaks volumes if you’ve already hustled and hacked your way to the right people versus sitting on the sidelines without having tried.  You’ve not nothing to lose and everything to gain!

I’ve now had my Kindle for a couple of months and I’m really liking it.  The battery life is amazing, purchases are seemless and fast, and the screen is easy to read from.  I’ve probably done more reading in the last couple of months than I have in the last year.

There’s something consipicuously absent from the Kindle, though—other people.  Reading and shopping from the Kindle is a disappointingly closed and solitary experience.  I can’t see what other friends of mine are reading from Amazon.  I can’t tweet my latest purchases.  I underline portions of books, but those clips just sit dormant on the device, completely unsharable.  What I’d really like to do is share all my book quotes on Tumblr. 

It shouldn’t be too surprising, though.  Despite purchasing Shelfari, Amazon has severely lagged behind the social game.  Despite the company’s blowout financial performance, you have to imagine the company is leaving even more on the table by not pulling its users into the service through social networking.  It could lock in loyalty to it’s fantastic Kindle hardware with network effects with a few simple features—like letting users opt in to sharing purchases.  The closest it ever came was letting Facebook post Amazon purchases through Beacon—and that didn’t turn out so well.  Perhaps they were left a bit bruised from that experience?

Still, you have to believe that a well thought out social strategy could cement Amazon’s place in the hearts and wallets of consumers and it boggles my mind that they’ve done so little in this area.

While I never did really stop seeing new deals, even when I was out of VC, now that I’m back in, I’ve really ramped up the deal flow engine.  I’ve been enjoying the meetings I’ve had over the last few weeks, but some of them have reminded me what I routinely see missing from most pitches. 

Here are the things that nearly every early stage investor needs to bet on that are too often missing:

1) Strong sense of the key milestones – Entrepreneurs often ask what metrics they need to get to in order to get an investment.  I often turn that question around and get them to tell me what the important milestones are.  Having 100,000 users may not be the right metric for everyone, and it also depends on stage.  A TechForward, a First Round Portfolio company, the team needed to find out whether or not consumers would buy into the idea of paying to protect their electronics purchases from obsolescence—and they needed a very small amount to prove it.  They knew exactly what metrics they were looking for—percent upsell—and how it was going to inform the business strategy—and whether or not there was actually a business to be made. 

Milestones are a waterfall—and having them as goals should inform product, marketing, financing, etc.  If you tell me getting to 25% penetration is critical mass, that’s what I’m going to judge your ability to execute against, and that’s how I’m going to evaluate the appropriateness and risk of the financing.  If you can’t identify a set of metrics that you’re driving at, there’s probably a zero percent chance that you’ll reach them.

2) Implementation of a product strategy – Especially at the stage that First Round is looking at deals (as early as a Powerpoint), we all know that the current product, as designed, is no doubt going to need a lot of work.  The idea will change.  So how is anyone supposed to know whether or not these future changes will not only be for the better, but that they’ll be implemented in a focused way that drive key milestones in the right direction?  You may think that search box needs to move, but how do you know?  More importantly, how do I know that you’re not going to spend the whole financing moving the search box around when it turned out that being on mobile was more critical to your success?  Do you have a roadmap?  How do features make it to the roadmap?  Moreover, how do features get removed from the roadmap, because chances are you’re not going to be able to do all of these things.

More so than any other aspect of the business, the thing I see early entrepreneurs tend to drop the ball on most—myself included—is product strategy.  I’m not saying you have to know all the answers, but you should at least know what your landing pages are trying to accomplish, where they’re going wrong, and what steps you’re taking to identify the solution.  I like to know that, even if you haven’t figured everything out, you have a process around product—so this way I can bet that you have the tools to figure it out.

3)  A theory on customer acquisition – You may not even have your product out yet, but having a reasonable sense on how people are going to discover it—past the buzz around your launch, is necessarily.  Just tell me how the first 10,000 users who aren’t your friends find it—and if it’s viral, tell me why people pass it on other than “because there’s an invite friends link.”  Zoominfo, for example, probably made a bet one day and said, “50% of people on the web do a vanity search at least once a year—and we’ll probably have 25% of those people in the US in our database to start, and 2% of those people, if we rank high enough, will come and claim their profile, which amounts to X number of users.”  

These numbers may always need to be adjusted, but at least you’re starting with someone you can measure against and identify where the issues are.  If your strategy is to reach out to all the bloggers in your industry and get them to write about you, that’s pretty much what every other startup is going to do—and anyone who has done it will tell you the results will likely be underwhelming. 

4) A financing strategy that gets you *somewhere* – For whatever reason, there are psychologically satisfying numbers out there that people seem to latch onto when raising money: $250k, $500k, $750k, $1.5mm, $2mm, etc… Nice round numbers.  Unfortunately, too many people pick one of these numbers based on the confidence they have in their ability to raise and quality of their network, versus picking an amount that actually gets you somewhere.  When I say somewhere, I really mean one of three outcomes:  getting critical mass (whatever that is for you) or at a product milestone that makes you venture fundable, starting to get revenues, or cashflow positive.  When someone asks you, “What does this money get you?” they really want to know that it gets you to some amount of users, coverage of certain platforms, first enterprise customers, whatever it is… just something more mission critical than “18 months”.

5) Specific value creation- The easiest way to show value creation is to say that each customer is worth X dollars in revenue.  Pair that with the cost of customer acquisition, and net net, there’s your business.  I don’t care if these are wild ass guesses—at least make some attempt at showing that at customer N, your business is worth X.  Would it hurt to make an attempt?  Sometimes, the value creation is in the network effects.  That’s fine, too… what do we think that network is worth?  I’m not saying you need an Excel spreadsheet, but very often I talk to entrepreneurs who have never even thought about these numbers and wind up realizing that the market their going after, even if they were a huge success, just isn’t very large.  Back of the napkin is totally fine.  If you’re running a music startup that helps people find experts to help them learn an instrument, saying that, each year, x number of people try to find a music teacher, the avg lesson is $20/hour, they stick with it an avg of 5 hours, then figuring out the price of lead gen for X number of $100 lifetime value customers goes a long way to figuring out how big this market can be. 

One thing I often hear when I talk to other venture capital professionals when I mention a particular deal is “There are a ton of people in that space” or “So many companies have tried that before.”  

I never figured out why that’s a bad thing.

If a problem is worth solving, of course a lot of people are going to go after it.  That’s why there are a million ad networks and more security software companies than you can shake a stick at.  These are huge markets and numerous companies are minting money in these spaces.  In fact, I’d beware of spaces where absolutely no one is playing.  Capital moves pretty efficiently.  If anyone else thought there was money to be made in what you’re doing—I find it hard to believe no one else would be trying it.

Not to mention that, if there are a bunch of people trying to do something, chances are no one has completely solved the problem.  Last I checked, ads are still pretty irrelevant and people still hack into things.

On top of that, we all know that being first doesn’t necessarily mean you’ll be the winner.  Google certainly wasn’t the first search engine, and Facebook wasn’t the first social network.  Apple didn’t make the first MP3 player either.

Rather than being dismissive about there being too much competition or a bunch of people who have tried to solve that problem and failed, I’m going to start pushing back when I hear this.  Why did they fail?  What did this next company figure out that might enable them to succeed?  Where these companies just too early?  Did they fail to develop a key feature?  Did they misunderstand how people wanted to use the product?

Often times, it’s a small feature that makes a big difference—like how del.icio.us basically redid Third Voice, but had tags instead of folders, and defaulted to public sharing. 

Whatever the case is—if you’re an investor and you feel like you’ve seen 20 other companies in this space, you should spend some time trying to figure out what you believe makes a winner—and why everyone else hasn’t had success yet, before you completely dismiss the whole space.