Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

Whitney Hess for 2008 Information Architecture Institute board of directors

"I believe I can help to grow our community, evolve the purpose of the organization, strengthen our partnerships with related organizations, and evangelize our vision to the greater population. I bring a fresh perspective and want to challenge some of the preconceived notions about what’s possible in this community. We’re at the tipping point of going mainstream and need to prepare for the influx of new professionals to come. I want to help make it happen."

- Whitney Hess

 

Whitney is super-committed to building community and I'm a big fan of her professional approach.  If you are an IAI member, please consider giving her your vote.

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Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

Consuming my friends

The other day, someone asked on the nextNY list who my "must read" blogs where.

I went to my feedreader and noticed something interesting.  By almost a 2:1 margin, the people whose blogs I read are people I know.  By and large, they were either blogs of friends, or blogs of professional contacts I had interacted with extensively either online or offline.

So my blog list is really just a list of people I know.  I read very few people just because I feel like I have to read them, and those that used to be in that category I've since tried to meet, if nothing more than just saying hi at a conference and e-mailing.

To me, that makes a lot more sense, because blogs, at their heart, are really made out of people.  They're a social technology, and if you're not socializing as part of your blog reading, as the lolcats say, "ur doin it wrong."   When you read a blog and never comment, never e-mail the author on the side, don't show up to the same meetups and conferences, you're basically treating blogs a passive, non-interactive mainstream media--and really missing out on a lot of potential. 

If you're reading this blog and not commenting, I can't see how you're really getting that much value, to be honest.  You could read about social media and tech stuff anywhere--but you can't get ME anywhere, and I'm just a comment, e-mail, or Plugoo message away.  (Can't say enough about that widget... my mom messages me almost everyday through it.)

The desire to consume and publish content to and from a small group of closely connected people is something tech types always underestimate.  Web 2.0 fanboys often know very little about the dynamics of places like LiveJournal, where an intensely loyal and close-knit community often shared with just 3 or 4 people on average--and there are a lot more LJers than there are Scobles of the world.  I've said it before, but most people don't want to broadcast to the world and be the most popular, nor do they want more content from people they don't know--they want relevance, and a sense of authentic community, which tends to be smaller.   That's also why Tumblr is taking off.  If you think it's just another blogging tool, you're not seeing the people connections in between. 

At the end of the day, I just don't have the time to hear about everything in the world...   but I need to make time to hear about what's going on in my friends' lives, and also to use them as a filter for content.  They are a filter not because we like the same stuff, but because their content meets the most important criteria of them all:

"Stuff someone I care about is likely to talk to me about soon..."

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Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

Another Voice Warns of an Innovation Slowdown - NYTimes.com

This scares me, too.  Kids are too into Paris Hilton and not into science.  We prevent people with technical skills from coming into this country b/c our immigration policy is FAIL. 

"Ms. Estrins book is the latest call to action during the last several years by scientists, technologists and political leaders worried about the countrys future competitiveness in technology. In 2005, the National Academies published Rising Above the Gathering Storm, a report requested by Congress, which found that federal financing of research in the physical sciences was 45 percent less in 2004 than in 1976 and that 93 percent of students in grades five through eight learn science from teachers who do not hold degrees or certifications in the topics. In 2007, the book Innovation Nation by John Kao, a business consultant, revived the debate."

Another Voice Warns of an Innovation Slowdown - NYTimes.com

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Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

NYC needs another early stage VC, or two, or three

Let me make this clear:  There's no shortage of money in NYC. 

A lot of deals get funded by random groups of angels, hedge fund managers, and other out of the way pockets of cash. 

There is, however, a shortage of experienced, local venture capital firms actively putting money to work here.  I'm sure people will disagree about the value that a VC can bring to a deal, but in my mind, they bring significant value to the community.

I was talking with a banker today about it, and there's definitely something to the "Silicon Valley VC mafia" phenomenon--that they all know each other and do deals together.  What they also do, which is incredibly valuable, is work with local universities, tech counsels, entrepreneur groups, etc., and actively participate in the community.  Their deals get huge press at funding time.  Their reputation of success is the community's reputation. 

By being consistantly active, they draw startups closer to them geographically.  That doesn't happen when a random hedge fund guy and his buddies put two million in a startup here in New York, because only that startup knows them.  That money builds a company, not a community.  Sure, money is nice, but VC's provide glue for the community in terms of the networks formed among deals they've invested in and support of the local community. 

Unfortuately, we don't have much of that in NYC.  If you're an early stage technology company, you're going to Union Square Ventures, Greycroft, Venrock, DFJGotham, SAVP, RRE, Softbank...and...  and who else?  These are good firms, but they don't represent enough of a critical mass--a mafia, if you will--to attract companies and talent here from the outside the way VC firms in the Valley do.  To be honest, USV and Greycroft haven't even been around for that long, even though their partners have.  RRE, which is a good firm with a successful record, says they generally invest between $5-10 million on their site, although they did less than that in drop.io.  I do hear they're looking to go earlier and smaller, so that's good.  Plus, I suppose Bessemer is in Larchmont and Canaan is in Connecticut.  These are clearly top tier firms, but if you can't go to the Shake Shack for lunch on a regular basis, are you really in the middle of this community? 

Comparatively, I'm going out to the Valley for VC meetings in mid-September, and I've got meetings with a dozen firms in three days--basically within blocks of each other in SF and then two days in similar proximity down in the Valley.  I know there are just a ton more firms out there, but it shouldn't be that there's such a difference in experience for an entrepreneur.

One major difference is community presence.  A lot of NYC-area entrepreneurs can't name more than a handful of NYC area funds and have never met a VC in person at a startup event.  I think a lot of NYC-area VCs could stand to be a lot more visable--attracting more deal flow by participation the way Union Square Ventures does.  Two or three NYC firms blogging and being transparent they way they are would count like 8 more firms doing deals here.

In terms of other firms, there's one firm not listed here that you might not realize that has done 10 technology deals right here in NYC since October of 2005. 

Take a guess.

Figured it out yet?

It's Spark Capital.  Ten out of their twenty-two deals have been done right here in the Big Apple--the most they've done in any city.   Spark has invested in 10 New York companies: 5min, AdMeld, Bug Labs, Covester, iminlikewithyou, Inform, KickApps, Next New Networks, Tumblr, and Clear.  Perhaps Spark should open an office here.  I, for one, would welcome another firm with a presense right here in the city.   Frankly, it surprises me that there aren't more, given the number of deals that get done here.  Even if you didn't plan on making all your investments in NYC, it's pretty centrally located on the east coast to do deals in DC, Boston, even Toronto. 

And it's not like deals aren't getting done here--but by out of town firms.  Redpoint did Right Media.  Accel put a bunch of cash into Etsy.  Emergence Capital just invested in Lotame.  Again, this helps the individual companies, but doesn't really help the community at large as would more early stage players doing similar kinds of tech deals with each other.

So who here is actually doing deals here in the New York Metro area?   I went into Thompson's VentureXpert database and ran some numbers on which firms have done "Early Stage", "Information Technology" deals in the last 5 years.  I'm sure some of the numbers are off (like Spark's number, which would seem to make it the 2nd most prolific NYC investor), but here's a list below of all the firms that had done two or more deals.  I don't have much more to say about the topic... hopefully you guys have some interesting takes on the situation...

 

Venture Firm

Total

Union Square Ventures

13

RRE Ventures LLC

9

Spark Capital

7

SOFTBANK Capital Partners

7

General Catalyst Partners (FKA: General Catalyst Group LLC)

7

Draper Fisher Jurvetson (FKA: Draper Associates)

7

Trident Capital

6

SAS Investors

6

Milestone Venture Partners

6

Accel Partners

6

FirstMark/Pequot

6

Draper Fisher Jurvetson Gotham Venture Partners

6

Connecticut Innovations

6

Village Ventures

5

Silicon Alley Venture Partners LLC (AKA: SAVP)

5

New Jersey Economic Development Authority

5

Masthead Venture Partners

5

Kodiak Venture Partners

5

Greycroft Partners

5

Bessemer Venture Partners

5

Bain Capital Ventures

5

3i (US)

4

Rho Ventures (AKA: RHO Management)

4

New Jersey Technology Council (AKA: NJTC)

4

Longworth Venture Partners

4

Intel Capital

4

First Round Capital

4

Edison Venture Fund

4

Canaan Partners

4

Oak Investment Partners

3

New Enterprise Associates

3

NeoCarta Ventures

3

BEV Capital (FKA: Brand Equity Ventures)

3

Lightspeed Venture Partners

3

Battery Ventures

3

Greylock Partners

3

Gemini Capital Fund Management

3

European Founders Fund GmbH

3

Draper Fisher Jurvetson New England (AKA: DFJ/NE)

3

Contour Venture Partners

3

Carmel Ventures

3

Constellation Ventures

3

Charles River Ventures

3

Amazon.com

2

Ventech

2

Venrock Associates

2

Velocity Interactive Group (FKA: ComVentures)

2

Valhalla Partners

2

Updata Partners

2

Tudor Ventures

2

Trilogy Equity Partners

2

Time Warner Investments (FKA: AOL Time Warner Ventures)

2

SVM STAR Ventures Management

2

Azure Capital Partners

2

Sony Corporation

2

Sevin Rosen Funds (AKA: Sevin Rosen Management Co.)

2

Scale Venture Partners (FKA: BA Venture Partners)

2

Advantage Capital Partners

2

Redpoint Ventures

2

Prism VentureWorks (FKA:Prism Venture Partners)

2

Polaris Venture Partners

2

Pennell Venture Partners

2

Paladin Capital Management

2

NewSpring Capital

2

New York Times Company

2

Apropos IT Ventures

2

Meritech Capital Partners

2

DN Capital

2

Battelle Ventures

2

Ackerley Partners

2

L Capital Partners

2

Inter-Atlantic Group

2

Hudson Venture Partners

2

Highland Capital Partners LLC

2

Easton Hunt Capital Partners

2

High Peaks Venture Partners

2

BRM Capital

2

Ascend Venture Group LLC

2

Goldman Sachs

2

Gold Hill Capital Management

2

Founders Fund

2

ETF Venture Funds

2

Allen & Company

2

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Venture Capital & Technology, nextNY Charlie O'Donnell Venture Capital & Technology, nextNY Charlie O'Donnell

Why don't more tech recruiters participate in the NY tech community?

Don't be shy.  We know you're out there reading, even though you just lurk.

Almost everyday, a recruiter calls our office number, even though we ask people not to on our site.  I'll let you all in on a secret--that number is not a real phone that rings.  It goes straight to PhoneTag and dumps into my e-mail in a transcription, so you're actually better off just e-mailing me.

The truth of the matter is, you all just kind of seem the same to us startup folk. 

You're selling us people...and we're a pretty hyperconnected group.  You'd be hard pressed to convince me that you can find anyone that I couldn't find on my own by just putting in some hours on LinkedIn or e-mailing various usergroups.  When I look up a recruiters name and they have 123 LinkedIn connections and I have 982, I think "What are the chances of them finding someone in NYC before I will?"

You're not selling screening--well, at least most of you seem like you're not, because the profiles I've been sent from recruiters so far are never really that good of a fit--and my CTO will still have to screen them thoroughly anyway.  Plus, so much of screening is about personality and fit, especially for an early stage company, and since the recruiters I talk to don't seem to have much interest in getting to know me as a person, I'm not sure how they could match me with a co-worker personality-wise.

But you know what... I could be totally wrong... and some of you are, in fact, really good at what you do.  The trouble is, I hear from all of you in the same way, leaving random messages on voicemail, or responding to my job posts, so you seem like a dime a dozen.  Where are you actively differentiating yourselves through branding?  Marketing?  Perhaps a little transparency in the process so that I could actually see why I could never accomplish what you could would go a long way--because this Web 2.0 world is all about transparency and we don't trust black boxes.

Good startups try and differentiate themselves by blogging--getting their name attached to good thoughtwork and getting into conversations around ideas.  Where are the really good NYC technical recruiting blogs?  Heck, if a NYC-area recruiter started a blog about hiring in this market, I think we'd all flock to it--and if you were really that good, we'd realize that recruiting is a helluva lot harder than we thought.  You could even post candidate profiles.  Give us your best tips on finding people, because, at the end of the day, most of your clients simply don't have the time or savvy to do what you do anyway, so you wouldn't be losing business by blogging, you'd be gaining it.

Not only that, why aren't you participating more in the community? 

I've met lots of random folks from the nextNY list and the range of people that actively participate here is pretty wide--from venture people to developers, business people, marketers, lawyers, etc...  but I can't think of a tech recruiter actively contributing here.   I don't mean self-marketing... I mean participating in the dialog.  That's partly why entrepreneurs really don't think highly of a lot of recruiters.  You act more like outsiders and salespeople, and less like one of us.

Are their NYC area tech recruiters on Twitter?  (And not just twittering their open positions or people for hire...)  Feel free to follow me at @ceonyc and send me a note!

This community needs strong recruiters, though...   not just recruiting people out of banks, but from out of state. 

Recruiters can be great evangelists for the NYC tech scene--I just don't really see them participating much in it.  
If you're a recruiter, and you're really interested in participating more in the tech community here, maybe this could help elevate your name from the noise in my voicemail.  nextNY will have a special event which I'll announce as soon as I sign the paperwork on it that needs some sponsorship.  E-mail me at charlie dot odonnell at gmail for details.

Given that you could probably cover the cost of sponsorship a couple of times over with just a single hire, and that there will be 200-300 tech folks at this event, I'd think the math would work out for you to take part, no?   I think it would be a really great opportunity to differentiate yourself and to open up a discussion about what you can do for startups, live and in person, not on phonemail.

You all really need to clear your calendars for 9/16 from 6-8PM.  Trust me.  :)  Details soon.

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Random Stuff, Venture Capital & Technology Charlie O'Donnell Random Stuff, Venture Capital & Technology Charlie O'Donnell

A Tech Blogger Daydream

What if I wrote a blog post... 

I've been reading all the right ones, following all the memes.  I've been thinking...about data portability, Facebook, the iPhone, monetization, being an entrepreneur, platforms, VCs, the Loch Ness monster and the theory of Atlantis. 

I have a good theory... err... Top 10 List... that ties them all together.  It's funny, too--even has some lolcats in it.  Yup...  Everyone will be talking about "meme platforms", because that's the new Web 2.0 catch phrase I created for this post.

I'll write it from my blog publishing software, and use Zemanta to suggest links, tags, metatags, keywords, related videos, suggested articles, other books you might want to buy, people you may know, lovers you have had before, fantasy baseball free agents on the upswing, and an appropriate chardonnay to go with this post.  I will not, however, check spelling.

I won't linkbait, but I can't help but quote smart folks like Robert Scoble, Fred Wilson, Om Malik, Henry Blodget, and MacRumors.

But first, I need to tell everyone I know about it--and right away.  This is too important to wait for them to read it in their Google Reader.  I'll post it to Twitter, and Hacker News, because... well..  I'm sure there are some people I know there, too.  I suppose while I'm at it, I'll tag it in del.icio.us, Digg it, StumbleUpon it, Sphere it, Reddit... it... (allow myself to introduce... myself), Newsvine it, Share it from Google Reader, since I of course read my own feed in my feedreader, you know... just to see what the feed looks like and that it's still working, Mixx it, Furl it, Ma.gnolia it, Slap it, Flip it, Rub it down, oh no!! 

And for a few close personal friends, I may IM it to them, too, just in case they didn't get my public DiggBeg.

And then...   I'll wait.

I'll wait for the inbound links and the traffic and all the blog love... and the haters, too.  That's ok.  I'm sure some troll will comment on my Friendfeed about how I have no idea what I'm talking about.  Flame war!  Everyone will start talking about it...  The Disqus comment notification e-mails start pouring in.  I respond and respond... and sometimes I respond to my own responses, creating a small tear in the space-time continuum.  I like words that have two u's in them in a row.  Am I talking in a vacuum? 

All of the sudden... BAM.  There it is... barely perceptible in small font all the way at the bottom, but it's definitely there. 

I'm on Techmeme.

Do I post a call for more links to push it up the list?  Naa... that would be pushing it.  I can't watch.  It's too much.   I need to go do something else.  I'll go monitor the del.cio.us/popular list.  OMG I'm already #3! 

Dammit...  

Stuck behind "100 CSS Hacks for people who still can't get shit to work in IE" and "50 incredible photos of children getting struck by lightning".

I'll never get past those.  Oh well...  3's pretty good I guess.

The real question is how many more RSS readers am I going to tack on?  I need to get to that next psychologically satisfying number...  the big 3000.   Of course, it's really just 1000 people who have inserted my feed into three different readers at one time or another but still... it's a nice looking number, no? 

Hmm... that gives me another idea.  Yes, that's it!  Tomorrow's post!

"Monetizing Meme Platforms...  ...in Second Life!"

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Path 101, Venture Capital & Technology Charlie O'Donnell Path 101, Venture Capital & Technology Charlie O'Donnell

Key to Entrepreneurial Success #234: Find a Crazy Partner

Alex and I were talking about our recruiting strategy over the weekend, which obviously will only happen if we raise our next round of financing.  He sent me these two e-mails...

"I'm thinking longer term though, we're going to raise this money, it's not an option or a question, this company is too good to not continue, I will do whatever it fucking takes."

Then...

"heh, got a little worked up there. ahem. I am prepared to assist, sir, to ensure that this company remains viable, by whatever means necessary, as I believe in it strongly  ;) "

This is why I think it's a bit silly when people post on message boards looking for a partner without much information at all.  You gotta get someone totally psyched about what you're up to, and to me, that means a lot of transparency.  Without insight into why what you're doing is so special, how is anyone going to get this crazy psyched about the company?

In Alex's case, he's psyched because not only is the company just as much mine financially as it is his, but so's the product.  I didn't come to him after all the wireframes were done and say, "Here, build this."  He joined when all I knew I wanted to do was help people figure out what they wanted to do--to solve one of the biggest problems people have in life.  We whiteboarded and explored and built the feature set together, collaboratively. 

Don't expect someone else to get really psyched about building your product.

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Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

Facebook's platform head-fake and the ball that LinkedIn dropped

The other day I signed up for the Web 2.0 Expo Conference Social Network (I'll be speaking at one of the workshops). It was powered by Crowdvine. I found it mildly annoying to have to retype my professional information when that already existed somewhere else on the web--namely LinkedIn. I tweeted that Crowdvine should integrate LinkedIn import, since I'd seen a few places hack it, and then very quickly got this response via Crowdvine's Twitter account:

 

  "@ceonyc We're just waiting for LinkedIn to release their API. So far they've just released the PR announcements."


It was true. It's been over a year since LinkedIn talked about releasing some kind of a platform and API's and we've seen very little. There were a few throwaway integrations into mainstream web publisher content, but little else.

Their initial move towards the platform and API talk came soon after Facebook grabbed the spotlight with its platform. After the buzz, particularly around the initial applications, died down though, it was obvious that the Facebook platform, in that incarnation, didn't live up to the hype. The quality of applications was really low, and everyday new measures needed to be put in to decrease friend spam. These measures, and the eventual redesign that pushed applications off to another page in your profile, left applications handcuffed and unable to spread as virally as they had in the past.

Initially, that made it seem like LinkedIn's wait and see approach might have paid off. Instead of opening up a platform, they focused on a redesign that made LinkedIn more user friendly.  They also focused on driving revenues, expected to be $100 million.  Facebook, meanwhile, went back to the platform drawing board, stubbing its toe on Beacon, but eventually coming out with Facebook Connect.  Crowdvine uses Facebook connect for me to see which of my Facebook friends are going to the Web 2.0 Expo in New York. 

Facebook Connect allows me to bring my social graph to any application. I can see which of my Facebook friends are already using something and invite more. This gives keeping my "real network" on Facebook a direct benefit. Even Google recognizes that just because someone is in your Gmail contacts doesn't make them your friend, which is why they recently updated their address book functionality.  I think Facebook Connect is just the beginning of a second, potentially much more successful push at powering various applications by Facebook.  Lessons learned from F8 and Beacon will pay off.

In the meantime, LinkedIn remains a pretty closed place where data goes in and rarely comes out. The odd thing about Facebook's charge at being the defacto social graph for all applications is that they don't really monetize data and people--they monetize pageviews. LinkedIn is supposed to be the one that monetizes people, whether they use the site extensively or not. Recruiters pay to access LinkedIn's network of professionals.

You'd think that a site where huge revenues come from directly monetizing the presence (not even the participation) of users would be doing more to get people on it.

Facebook's value proposition to users is pretty clear: All your friends are there. Whatever functionality and applications you want to think about on top of that is gravy. You want, and dare I say at this point, need to be there because everyone else is there.

Don't get me wrong. I use LinkedIn nearly everyday, have nearly 1000 contacts, and I get a lot of value out of it. I'm in the minority, though. Most of the people I know are only on there because they got invited and do little more than accept invitations. That might bode well for the experience of being on there--most people don't get spammed--but at some point, that fails to create additional value. If you're selling people and you don't even have a quarter of the people your competitor does, you better know those people cold--and that has to come from active usage. The more I do on a site and the more that site plugs into other places that I'm active, the more data that site is going to build up on me.

That's why we're bucking the "do one thing" Web 2.0 trend at Path 101. We think that giving users a number of complimentary things to do around discovering their career interests, the better the picture of them as a potential candidate we'll be able to create--and the more people we'll capture through diverse methods.

Facebook may not have figured out how to monetize me yet, but they know me better than any other site--the data's either all there or well within reach. Perhaps Lotame, with its interesting ad platform built specifically to be powered by social network data, will be the answer.  The East Coast company, which just raised $13 million, uses user data to "target the most influential members of social networks and measure a campaign’s success as indicated by user generated content related to the brand."

I think at the end of the day, if you have a platform made of people, you've got to open up so that you can gather a much deeper understanding of who you have.  Just allowing people to connect and throwing a rather remidial free text search on top of superficial profiles has worked mostly because the alternatives--the noisey firehose of Monster and Jobs 1.0--was so bad, and the need to hire great people is so high.  Side note: What other market besides recruiting is the pain point and business criticalness of a task so high and the solution sets so bad?  To get to the next level, I believe LinkedIn will need to fully commit to a very comprehensive and even risky platform strategy--and iterate on it like Facebook has. 

Unfortunately, they might already be making too much money to bother, leaving most of it's potential on the table.

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Random Stuff, Venture Capital & Technology Charlie O'Donnell Random Stuff, Venture Capital & Technology Charlie O'Donnell

Kind of tech partied out

Back in February of 2006, when nextNY started, there weren't a lot of social events going on in the NY Tech scene.  Now, it seems like there's a party going on every other day--and not parties for specific user groups or industries, where the chances of you making a connection to someone relevant are pretty good--just these big generalized "tech community" parties with sponsors no one really cares about. 

It's fun if most of your friends are tech and digital media folks, but mine aren't.  I grew up here in NYC and was a finance guy long before I was a tech guy--not that all my friends are finance people either.  My best friends work in publishing, law, and television production.

That's not to say I haven't made really good friends in the tech community.  I have, but I don't only see them at "industry" events.  I try to see the people in the tech community that I'm actually friends with in smaller settings like at the Shake Shack or for 1:1 lunches.  I play on sports teams with them and invite them to go out with me and my non-tech friends. 

So when I bounce from these bigger, generalized, noisy parties early, it's often because there's someone I know for years, maybe since junior high, waiting somewhere for coffee--or I just have a ton of work to do and can't go out every night if I ever expect to see my parents and other family. 

I think because I don't necessarily take part in the "scene" as much as others, I get a little bit of a reputation of being standoffish, or not sociable.  In actuality, I'm very social--just not necessarily with 300 random strangers who also have websites. 

Sometimes, I think that people think this is what is meant by "participation" when entrepreneurs out looking for money or deals for their startups attend these parties.  I don't know about you, but I never quite feel like these big things are my community and I always wind up hanging out with the same people anyway.

I think entrepreneurs are better off spending as much 1:1 time with people who's opinions they respect and admire, who actually know their space a bit, and also creating communities around them.  No matter what the industry or interest, there's a smaller community of people that you should be gathering together to leverage and exchange ideas.

Hey, if you wanna drink on someone else's tab, these big parties are great... but don't mistake them for or let them replace the more authentic, true relationship (and dare I say friendship) building that needs to be part of your networking.

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Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

What entrepreneurs need to Start: A conference recap

Last Thursday, I attended Jeff Veen and Bryan Mason's Start Conference.  First off, I want to thank them for all their hard work--it was a refreshing event with a sincere approach.  Right off the bat, priced at $200, you knew that these guys were more out to actually lend entrepreneurs a hand than make a quick buck off them, so I appreciated that.

As I sat through the morning interviews they had set up, I realized that successful people have trouble attributing success to specific actions taken.  There were a few spots in the conversations where key points were glossed over with things like, "And soon after we launched, the product took off..."

Whoa!  Back up the truck!

How?  Why?  What caused success and did you plan for it?

I mean, you know, besides the fact that you created a great product and all, because I definitely took that note down.  "Create great product... check."

Failures are often easier to figure out.  Usually, when shit hits the fan, you know exactly what you did wrong, whether or not you're willing to admit it, but success--crossing that chasm is often something that people can debate for years.

I think someone ought to create a conference just about failure--that all the speakers can do is talk about stuff that went wrong.  We'll call it FailureCon or something.  That's one of my favorite things about having so many entrepreneurs as angels--if I could just manage to avoid half the mistakes they tell me they made, Path 101 will turn out ok. 

Still, attempting to get a list of likely success causes and best practices would be a good start.  I would have liked to see more structured conversations.  George Oates did a fantastic job up on the stage monitoring the audience feedback--perhaps another person could have an expanded role in recording specific takeaways and lessons.

That's another cool thing about the conference--George's presence was an indication of their willingness to experiment to create the best outcome possible for all those involved. 

How about a "what worked/what didn't work" ledger, with each speaker needing to add at least one or two things to both?

Or some kind of lesson voting system for the crowd... where the conference recorder person could add lessons learned to a publicly displayed voting site, the audience could add their own, and at the end of the conference, you'd have 10 solid takeaways. 

One other thing I'd like to hear more discussion of is product.  Making a great product always seems to be what being successful is all about, and everyone usually feels like they have one, but obviously that's not the case.  I'd love to see more product folks go in detail on what makes a great product, how to reposition things when they're not going well, and now to go back to the drawing board.  I'm happy to toss my "7 Product features you should add right now" talk from BarCampNYC.

One other idea...   It seemed like Jeff and Bryan, not surprisingly, attracted a great crowd.  The only problem was, I had no idea who was there and what they were up to, so I really didn't know who to meet.  Perhaps a Ning or Crowdvine site setup beforehand would have done the trick?

All in all, though, I'm glad I went.  Getting to pitch in front of the conference was awesome and I got great feedback (more focused deck coming soon!).  One thing I was a bit surprised at was that other than David Hornik and Rob Hayes, who were both involved with the conference, I didn't spot very many VCs.  You'd think this is the kind of thing investors would show up to.  I guess there's not enough mindless hype about Start yet.  Perhaps that's why I'm inclined to show up again.  :)

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Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

Free Business Plan: Ask Smart People to Blog (inspired by kortina.net)

I can't agree more with Andrew Kortina:

"I find my self asking many of my friends these days to start blogging or at least posting commentary on interesting web content. My motivations are partly selfish and partly altruistic.  The thought process:

I like to befriend smart people.  They have good ideas. Conversations about good ideas lead to better ideas. Geographic constraints should not prevent good ideation."

I do the same thing, with varying amounts of success.  Not every smart person in my life is going to agree to start and maintain a constant blog.  What I'd really like is a post by post blog invitation service.  If I could just ping people with questions by e-mail, and their responses could automatically wind up on a blog, that would be awesome. 

Sure I could do a lot of cutting and pasting, but it would be a lot more seemless just to have a page to send questions out to people, and have the responses automatically show up on the blog, like Disqus does with comment notifications.  Plus, you could even e-mail back the creator with a link for editing, ping them with comment notifications when people respond, etc.

The quality of such a blog would depend on the owner's ability to ask great questions to smart and interesting people.

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Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

Printing web to PDF

So I was just thinking to myself that I'd love a way to make web pages available offline for airplane and other types of offline reading.

Then I remembered Universal Document Converter.  I'm sure there's some free, open source thing I missed, but a while back I had to convert something to a TIF file or something random like that, because it turns out the copy of Powerpoint I had wasn't exactly kosher.  So I wound up paying for the Universal Document Converter and it's been a really easy way to print documents automatically to PDF.  I don't own a printer and try not to keep any paper files, so this has been a great way for me to organize my digital documents storage.

So I just realized I can easily print web pages to PDF and keep them for later.  There's a bunch of stuff I'd like to read on my plane ride back to NYC and now I have a bunch of PDFs in a folder.  Nice!

Still, it would be cool if something could run in the background pulling in my del.icio.us links that are tagged PDF and automatically do this for me.

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Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

How do you manage the professional digital you?

I blog and I twitter.  It might seem to some like I'm sharing everything and totally out there, but I'm not.  For example, you don't know who I'm dating.  That's mostly to protect the innocent, but also because it doesn't involve you.  Plus, I believe, unlike some people, that certain personal things don't need to be shared, lest we all appear like train wrecks to the world.  We all know that there are many moments in our private lives that are momentarily or multi-momentarily train-wrecky that don't impact our ability to just get stuff done.

However, everyone's line is different, and so is how we manage ourselves between those lines.  Take Facebook, for example.  I think it's bizarre that people I only know professionally want to be Facebook friends with me.  I deny them not for any other reason than it makes my own experience of Facebook noisy.  Just because we met at a business development meeting doesn't mean I need to see the photos you uploaded of your kids, or when you add a Little Green Patch. 

What this means is that I don't wield the same size sphere of influence as someone like Jason Calacanis, but you know what?  I don't want to.  To me, there's something to be said for authenticity.  I may have 950 LinkedIn contacts, but I actually know them.  And my Facebook friends?  They're actually friends, for the most part.  Yet, I'm still, in my opinion, able to maintain a very extensive and very fruitful online presence. 

Certainly people have different approaches and that's what I'd like to explore at my SXSW talk with Alana Taylor.  Alana is an NYU student who is a great social networker, but in my opinion, also stays on the right side of the authenticity balance.  I'm sure she'll have a lot to say as a college student about her professional world colliding with her personal digital spaces.

So if you'd like to join us in exploring "Blurry Networks: Friends, Contacts, Followers and Professional Me", please vote for our panel.  Thanks!

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Random Stuff, Venture Capital & Technology Charlie O'Donnell Random Stuff, Venture Capital & Technology Charlie O'Donnell

Weirdest random Plugoo exchange ever

[SABYA] I WANT SOME WIDGET           2:09 PM
[SABYA] ARE YOU THERE

ceonyc                                                2:09 PM
What kind of widget?

myplugoo                                             2:09 PM
[SABYA] FLASH CONTET

ceonyc                                                 2:10 PM
Ok... I get you flash widget.   How much you pay?

myplugoo                                               2:10 PM
[INFO] Visitor [SABYA] has left the conversation.

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Nobody here but us low horses

A friend of mine's dad runs a large landscaping business with over one hundred employees.  While the business has been in the family since 1939, when he took it over in the early 70's, he really took it to the next level.  That often happens when the reigns of a business finally pass on to the next generation.

Anyway, what we're doing at Path 101 doesn't even hold a tea candle (yet!) to what he's accomplished.  This is a real business that sells real stuff with revenues, EBITDA, 100+ employees, trucks, etc!  It would be easy for someone with so much success to dismiss a small angel funded web startup in Alpha, but instead, he took a lot of interest  in what we were up to.  He even brought me up to a neighbor as another guy running a business who knows what it's like to work hardest for yourself.  I really appreciated getting that kind of respect towards our humble beginnings--especially from a friend's parent who might naturally be prone to a more unbalanced power dynamic.  Instead, it felt like two entrepreneurs shooting the breeze and it was pretty cool.

And yesterday, I got a nice note from Marc Cenedella checking in to see how things were going with Path 101 and an invite to come chat about the recruiting market and startup stuff.  I'm sure I'll learn a lot more than I can contribute to the conversation, but similar to my friend's dad, he asked some questions in our exchange about what the sweet spot is for when in a person's life Path 101 is useful. 

I really appreciate when successful folks like this can take a second to think about somebody else's business--but more so than that to take it seriously despite the vast distance between our respective progress.  It's a stark contrast to a recent situation where someone told me how they'd do things completely differently and never really acknowledged the progress we had made or my vision for the company.

At the end of the day, I just don't sweat situations like that.  You can't impress everyone and not everyone is going to care what you're up to.  You've got limited time and resources in a startup, and you just need to work with the people who believe in you and not worry about everyone else.  I guess relationships are kind of like that, too.  Some people are going to accept you and be excited to be with you.  If you spend more time building strong relationships with these people, and less with those who aren't interested, your life will turn out just fine.

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Path 101, Venture Capital & Technology Charlie O'Donnell Path 101, Venture Capital & Technology Charlie O'Donnell

Are prospective investors killing your vision or fueling your fire?

Yesterday, I had an amazing call with a guy with thirty years experience in the recruiting market.  For years, he had a vision of a service doing exactly the kind of things we plan to do with Path 101--not necessarily on the helping people figure out what they want to do side, but on the data-centric, getting to know candidates better side.  We saw completely eye to eye on how badly this market needs to do more than figure out eighty different ways to smash a resume and a job post together, or mindlessly connect people without adding intelligence to the process.  What he also believed in, which we do strongly, was that it needed to be a service people opt-in to--something that provides value to the user every step of the way, encouraging them to participate more and submit more information about themselves. 

What was amazing was that this guy went the distance in terms of describing the power of the vision--referring to it as "one of those four or five big stories..."--while at the same time, he realized that we needed to take small steps to get there, but that directionally we were in the right place.  At one point, the grokking was so intense, we had to pull back and say, "Hey, we need to pull back and let this sink in... let's talk next week." 

While I absolutely believe Path 101 can be one of those companies, there's never been a purpose to describe it as such to anyone like that, particularly investors.  In fact, going through the fundraising process actually forces you into quite the opposite mode of thinking.  Your grand vision starts slowly dying a death by a thousand cuts.  They start nitpicking on features they dislike, or question how long it will take before you drive revenues, or they want to know how are you going to get people to come to the site.  (Which is the most ridiculous question of all time, because every single company has the same answer--SEO, social media tools, PR, or some kind of partnership...and maybe some traffic purchasing... what other traffic is there?  Doesn't everyone say the same thing?)   

Eventually, you find yourself thinking smaller--that if you can't find anyone to believe your big world-changing vision, you try to convince people of small things--how you just want to get to the next product step, how you can pull down some low hanging fruit revenue, etc.  God forbid you should look out further than your next financing in your plan--well don't bother because who's going to believe you, right?

Meanwhile, I was at a panel discussion with four VC's and some of them were talking about "Web 2.0" deals and how they need to do extra diligence on the mindset of the entrepreneur because they need to make sure they're in it to build a big company and don't want the quick flip.  Well, how many game changing companies out there had a clear path to the world changing vision at the point of their angel round? 

Perhaps the reason why so many Web 2.0 companies are small ideas and quick flips is because we've never had so much transparency into the VC mindset as we have now, and what entrepreneurs are hearing isn't "Think big", but "What can you show me now?"  Well, big takes time, and small can be built on Ruby-on-Rails this weekend... and don't expect small to resist a $30 million sale to a media company.   Thus far, no new potential investor has flat out asked me how Path 101 changes the world, and only one has even come close to turning the conversation into how big this gets. 

del.icio.us, for example, was a company where lots of people scratched their heads and said, "Bookmarking?  I don't get it," while at the same time, others, like those of us at Union Square Ventures, thought that people-powered search and discovery was a potential game changer and maybe even a Google-killer.

The key is finding that one person who believes in that vision like you do--even if you haven't previously been #2 at Paypal or built Skype or whatever.  It's hard to do that as part of this process.  I told this guy yesterday that while I totally believed in this vision, as CEO, I also had to deal with the harsh reality that the well runs dry in January, and so no one's changing any worlds without some more cash.  Walking in the door and saying, "I know we're in Alpha and rolling out our product at the moment, but here's how this changes the world", unfortunately, isn't usually the path to solving that immediate need.

I wonder if your expected value increases if you grab your pick ax and go find that one person who believes in the big vision, versus thinking small and incremental and showing what you can do tomorrow so someone will fund you today.  Companies would certainly behave very differently depending on what kind of feedback they get from their supporters, and so I wonder how much the early exit/flip Web 2.0 small idea mentality is a product not of entrepreneurs but of the investment community itself.

UPDATE:

Of course, I really don't want to just come off like I'm complaining.  If you know me, you know I always look for actionable next steps anytime I see an issue.  For me, what this whole experience has me doing is thinking about ways I can better convey the vision and end goal to the folks who need to see what that first step on the path looks like.   Sometimes, though, its just nice to get unbridled support on the vision rather than just spend 99% of your time defending the product plan.

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Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

Why trying to Out-Google Google is a search for FAIL (and how to actually do it)

When there's an 800 pound gorilla in your space, trying to steal bananas isn't exactly the smartest approach.  You figure out what he's not eating, and you start nibbling.  Before you know it, you're eating just as much as he is and wouldn't you know it, one bad banana crop and he's toast. 

So when I hear that someone wants to build a better search engine than Google, while I don't think it's impossible, I question along what lines they're trying to do it.  Can you really do it by indexing more pages than Google?  I find that hard to believe, because an infrastructure arms race with Google seems like a bad idea--no matter how efficiently you think you can manage your crawling costs.

Smarter algorithms?  Maybe, but isn't algorithm quality a function of sheer brain power of your search team?  Again, this isn't where I want to take Google on head to head.

No, where I think you can beat Google, or at least make some headway on them, is with people.

At the end of the day, computer interpretation of human behavior and desires is what drives Google.  You could attempt building a bigger or faster computer, but no one computer is really going to be able to interpret people better than, well, people.

That's why del.icio.us had so much potential.  Google could never figure out what was funny or interesting, but del.icio.us could. 

To me, it's also the reason why Firefox gained so much ground against Internet Explorer.  It wasn't that smarter people work on Firefox--it's that more people worked on only the things they cared about, solving problems for themselves.  The best ideas floated to the top and became part of the codebase.  Things got addressed that weren't a priority for the IE team, but that more engaged users had keen insight into the value of.  The more you directly involve people--at scale, which isn't easy--into the process, the better your product is, because your product is made for people.

So, right now, Cuil and a number of other startups have teams of a handful of people who are supposed to know better than all the Google people what users want out of their search and how to search better.  Why not, instead, open up the process to something more open source--more Firefox-like?

Here's what a more collaborative approach to building a better search engine might look like:

Backend:

Outsource just the basic crawl to Amazon, because they've probably got the best shot at competing cost effectively, but enable outsiders a chance to add elements to the crawl.  So, if you have a way of categorizing pages, like Cuil says they do, add that ability to the Amazon powered crawl, and your special taxonomy and tags will be available for anyone to access, work on and improve. 

Let others use your infrastructure to target specific pages with a different type of crawl and contribute to the results.  In other words, let Indeed and others run their crawlers on your infrastructure, so that the barrier to create new attempts at search isn't set artificially high.  This will make a lot more sense when we talk about Plugins.

Plugins

There are lots of different types of search that Google just doesn't do well, like jobs and events.  This has given rise to some opportunities in the vertical search market   Let's take that Indeed example.  Right now, Indeed searches jobs much better than Google does, so why not enable Indeed, Simply Hired or anyone else crawling jobs to outline what represent job keywords and searches, and automatically provide results for them.  You could even randomly rotate which job search engine plugin powers your job search and let them duke it out for highest clickthrough rates, or allow the user to set a default. 

Basically, a "plugin" would be a hosted version of the third party crawler that gets sent queries based on their structure, keywords, etc., and gets to send back all the results they can, as well as gets the opportunity to advertise against them.   So, in our "open source" search engine, when I type in "marketing jobs, new york, NY", instead of getting a page of links to search engines for their marketing jobs queries--i.e. an "extra click"--I'd actually get jobs as my results, and Indeed powered job ads.

The same could go for movies.  How many times do you type a movie name into Google, knowing full well that IMDB is going to be the first result?  Why not allow IMDB to be the movie plugin?  They could directly provide structured results for all the actor and movie queries and be allowed to advertise against them.  This way, you eliminate the Google middle man when all you were really trying to do was reach IMDB in the first place.  All you'd need are some standardized display templates for results, which could also allow some interface flexibility for different types of queries, like videos or location searches on local maps.

People could build other types of plugins, like one that would automatically display RSS results when blogs came up high in your ranking.  I get Google results for "Charlie O'Donnell's blog"...  let Newsgator build that plugin and power it with all of the clickthrough data on what my interesting most recent posts were.

The system of sending queries to the right search tool would be a kind of AdWords platform, but a level up the chain.  Instead of a marketplace for advertising next to one kind of search result, you'd have a marketplace of search results, each coming with their own ads in tow (or using a default ad platform that anyone could use.)  You could attempt to "buy" certain keywords to put your search results next to them, but you'd have to get good clickthrough performance to keep appearing.

Personalization

You'd definitely allow users to add their own scripts and plugins, as well as have them contribute other types of data.  Let me pump in my blog, my del.icio.us tags, twitter feed, etc. in an effort to teach the search engine all about what I like.  Let me remove results, follow my clicks... learn about me (and my friends) as I go along.

 

The company that should really get into this is Yahoo!  They couldn't out-Google Google on search or monetization, so they should just crack open the whole thing and let the community and other companies have a shot at it.  They could be the default ad network for searches that weren't powered by plugins...   and they could strike deals with plugin providers to take a smaller cut than Google would have had on ad clickthoughs. 

If not, I still think it would make for a pretty viable community project.  Hell, maybe Mozilla should be the one to work on it, or are they getting paid too much by Google for Firefox default search to rock the boat there?

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Path 101, Venture Capital & Technology Charlie O'Donnell Path 101, Venture Capital & Technology Charlie O'Donnell

Real apps for real people with real problems

"So we are thrilled to be an investor in a company that has been organized since its inception around the key insight that we believe will drive the next several years of innovation on the web – the need to solve real problems in the real world for real people."   - Brad Burnham on USV's Investment in Meetup

 

If only there were other companies solving real problems for real people.

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Venture Capital & Technology Charlie O'Donnell Venture Capital & Technology Charlie O'Donnell

Free Business Plan: Grease this post

Have you ever written something you really thought had a chance to go viral.  Maybe it wasn't even linkbait--it was just something you thought was really original and thoughtprovoking, and if only the right handful of people, or a critical mass of your friends caught onto it, it would take off.

So what do you do?

You bite the bullet and you start asking for people to Digg it.  Ugh.  There's nothing worse than being a social media panhandler.  It makes you feel stripped of your authenticity.  You might as well be pushing Rolexes.

So, what if, instead of blowing so much social capital on Diggbegging, you could easly throw a few bucks towards it to get it in front of the right bloggers.

Feedburner had something a little bit like that--where you could figure out what the CPMs were on your blog and advertise your feed in the feeds of other people in order to try to get more users. 

For businesses, easy tools like Clickable are really lowering the overhead it takes to have your own SEM strategy.  What individual contributors need is a kind of mini-Clickable right at the point of creation.  How great would it be if, right next to the publish button, there was another button that said, "Do you want to invest $10 in driving relevant traffic to this post?"  The money could be used to not only do search placement, but sponsored placement as "Suggested sponsored links" in front of bloggers talking about the same things.  They wouldn't get paid to reblog, so it wouldn't be like PayPerPost--you'd just be paying to get in front of people who are likely to reblog the idea.  

Another aspect of this is a better way to actually get your friends to reblog, Digg, tweet, etc. on your behalf.  What if I could sent one link around that gives people a menu with the minimum number of clicks necessary to spread it.  They could have their blog id/password, twitter password, digg, etc. already saved, so all it would take are some checkmarks and some additional optional descriptive copy in a few places and press "spread".  There are lots of times I would reblog something relevant that my friends send me, but I just don't have a lot of time to crack open the blog editor, do the appropriate cutting and pasting, etc.  This would come in especially handy when people send me jobs to repost.  I'd repost most of the jobs that people send my way, but it's kind of a pain in the ass.  If I could create a trusted list of friends that are allowed to repost their job ads to my blog, and maybe even aggregate them, I'd pre-approve people to do it.

Because who really wants to be a social media panhandler?

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