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

The other side of Paul Graham's Coin: Ideas on the kind of VC we'd like to get funded by

Paul Graham just posted some ideas on what kind of startups he'd like to fund on the YCombinator blog.  I suppose if you're already working in these areas, that's great news for you, but to be honest, if you're not passionate about one of these things already, I never believed in the idea of just methodically picking picking a sector to start something in.  Fabrice seems to be doing a bangup job at it, though, so I could be totally wrong (although his passion seems to be the methodology and the process itself, though).

Anyway,this isn't the first time one of these lists has popped up before--and I'm sure it sends a lot of entrepreneurs scrambling.  In order to provide balance in The Force, I thought it might be better to tell all the VCs some ideas about what kind of partner I'd like to fund Path 101.  Let the VC's scramble around!

So here goes:

1) We're looking for a partner who is really passionate about helping people find their callings--someone who is looked at by others as a great mentor and actively contributes their career wisdom to others.  If we're talking about our career advice tool and you have to ask, "Why would anyone answer someone else's career questions?" that means you don't actually provide that advice yourself when you get random e-mails from your school's alumni or people from your blog, etc.  We want someone who knows what it was like to not know what you wanted to do and feels like we can really make a big impact by helping people with their career.

2) We want someone who really believes in backing people.  Our product will take many public iterations before it ever feels "complete" and there are still many unanswered questions left that we will only be able to address over time.  That means, at the end of the day, you've got a team and a market.  We're sure the market of "people who aren't sure what to do with their careers" is pretty huge, so that leaves you with team as the real bet--and so we need to feel like our team has the confidence and support of our investors.

3) Someone with access to domain knowledge in our market.  It will be some time before we build the recruiting inroads to our userbase, but it would be extraordinarily useful to be able to regularly pick the brain of someone who knows the space or can open up the right doors here.  That's true for any startup--having a resource to go to in order to help grease the biz dev or acquisition wheels is seriously value add.

4) We want a user--someone who participates in the social web to the point where we say, "and this is how it plugs into people's blogs" they'll get it because they blog or know how they work, not just because "blog" is a buzzword. 

5) Someone fun!  I need to be able to pick on you via Twitter.  If we can't laugh about something, hit up a ballgame, or just kick back and genuinely enjoy each other's company, it's going to make things a heck of a lot harder.  We have a fun team (in a geeky sort of way) and we get along with each other really well.  Our backers are going to be joining that team and need to be able to get along with us.

6) A partner who can get their whole firm on board.  Obviously some level of this has to be attained to get a deal done, but sometimes partners change and other times, different partners or junior folks have something to contribute.  I'd like to be able to walk into my VC's office and have just about anyone there be interested in talking to me--and not have to feel like I'm waiting for just one person.

7) Someone principled and ethical.  We're in this because we want to make an impact on people's lives--because the difference in your life between hating what you do and really finding where you fit is huge.  We also think it can be successful, but that's not going to be from taking advantage of others or squeezing every last dime.  I want to feel like we're in good hands with a trustworthy partner and that's what I think I can offer in return.

In return, a VC will get a team that is extremely dedicated and passionate about solving a big mainstream problem with creative, appropriate solutions, that works really hard, and that they can trust in return.

Anything else I should be looking for?

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

Love and Startups

I want to find someone who not only loves me, but lets themselves experience love and doesn't worry about the chances of things actually working out. 

Relationships are like startups.  If you join one because you think it will be successful, versus just joining one because its interesting, worthwhile, and its something you're passionate about--regardless of its ultimate chance of success--then you shouldn't be in one.  Most relationships, like most startups, don't last forever.  They're also completely unpredictable, so you just find good people, communicate well, and do your best.

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

New goal: Meet everyone on the SA 100 List

The other day I was thinking about the NYC tech community and how most of the events I've been to lately are about up and comers, which is great, but I feel like I still have a lot to learn from those who are a lot more experienced.

So, I'm going to try to make a concerted effort to meet up with more folks that have had prior successes and try to learn from them.  Hopefully, they'll get something out of meeting me as well. 

Seems I've met about a third of the list already...  I don't know if I'll get to all of these folks (how likely is it that Barry Diller will grab a Jamba Juice with me, right?), but given the aggregate wisdom of these folks, I think it's a worthwhile pursuit.

Here's where I'm starting from:

 

The 2007 Silicon Alley 100 1. Michael Bloomberg - Been to Internet Week kickoff at Gracie Mansion: NEVER MET 2. Barry Diller: NEVER MET 3. Fred Wilson - Worked for 4. Alan Patricof - Met at USV while he was out gathering feedback on starting Greycroft 5. Scott Heiferman - Who hasn't met Scott? 6. Tim Armstrong - NEVER MET 7. Nick Denton - NEVER MET 8. Quincy Smith - NEVER MET 9. Esther Dyson - Met through NY Angels meetings, del.icio.us angel meetings 10. Bob Pittman - NEVER MET 11. Randy Falco - NEVER MET 12. Ken Lerer - NEVER MET 13. Alan Meckler - NEVER MET 14. David Liu - I really want to meet David, b/c I make comparisons between Path 101 and TheKnot all the time. - NEVER MET 15. David Rosenblatt - NEVER MET 16. David J. Moore - NEVER MET 17. Dave Morgan - Awesome guy, met through USV 18. Mike Walrath - NEVER MET 19. Jim Cramer - NEVER MET 20. Martin Nisenholtz - Met at first USV Sessions... shook hands, didn't chat long, but close enough. 21. Marc Cenedella - Met at Laurel Touby's networking breakfasts 22. Ken Bronfin - NEVER MET 23. Andrew Ross Sorkin - NEVER MET 24. George Kliavkoff - NEVER MET 25. Jeff Jarvis - Met at breakfasts, meetups, airports, SXSW, Twitter, and he's a Path 101 angel 26. Tom Clarke - NEVER MET 27. Brad Burnham - Worked for 28. Beth Comstock - NEVER MET 29. Saul Hansell - NEVER MET 30. Mel Karmazin - NEVER MET 31. Bob Bowman - NEVER MET 32. Stephen Rattner - NEVER MET 33. Lockhart Steele - NEVER MET 34. Herb Allen III - NEVER MET 35. Tom Glocer - NEVER MET 36. John Borthwick - Met at Betaworks lunches 37. Strauss Zelnick - Was supposed to meet him when a placement agent was showing his fund around and I was at GM, but NEVER MET. 38. Wenda Harris Millard - NEVER MET 39. Jason Hirschhorn - NEVER MET 40. Jacob Weisberg - NEVER MET 41. Peter Rojas - Seen him around USV and conferences and stuff, but never actually talked to.  I'll count that as NEVER MET, b/c he seems like a cool guy. 42. Sarah Chubb - NEVER MET 43. Mitch Davis - NEVER MET 44. Seth Godin - Met lots of times at USV 45. Eric Hippeau - NEVER MET 46. Jed Katz, Ross Goldstein - Met Jed at a breakfast, haven't met Ross - SPLIT MET 47. Doug Lebda - NEVER MET 48. Mika Salmi - NEVER MET 49. Sal Iannuzzi - NEVER MET (but obviously should :)  ) 50. Robert Kalin - Met lots of times through USV's investment in Etsy 51. Are Traasdahl - NEVER MET 52. New York Post Business Team - NEVER MET 53. Jeffery Boyd - NEVER MET 54. David Kenny - NEVER MET 55. David Kidder - Met a few times, but we're supposed to do lunch... Let's get that up on the cal, David! 56. Michael Yavonditte - NEVER MET 57. Jonathan Shapiro - NEVER MET 58. David Card - NEVER MET 59. Fabrice Grinda - Met lots of times, though USV, various meetups, breakfasts, etc. 60. Dany Levy - NEVER MET 61. Howard Lindzon - Howard's a cool dude... met. 62. Randall Rothenberg - NEVER MET 63. Robert LoCascio - NEVER MET 64. Jonathan Miller - Saw him speak once, but NEVER MET 65. Ralph Bartel - NEVER MET 66. Jeffrey Citron - NEVER MET 67. Laurel Touby - Laurel's great... she never remembers me when I see her, but she never remembers anyone.  68. Danny Stein - NEVER MET 69. Sascha Lewis - E-mailed, talked on the phone, never met in person, but that will happen I'm sure sometime. 70. Connected Ventures Team Met them. 71. Charlie O'Donnell - I hear this guy's pretty cool. 72. Stephen Messer - NEVER MET 73. Adam Benjamin, Roger Jehenson - NEVER MET 74. Jason Rapp - I actually think I have met Jason, but I'm not 100% sure.  Push.  75. Anthony Noto - NEVER MET 76. Jason Calacanis - Met before I knew who he was, at a Tae Kwan Do tourney...and then met several other times at tech things. 77. Steven Johnson - Met at USV annual dinner, and he took me to lunch once while I was getting feedback on Path 101.  Awesome guy. 78. Jen Chung, Jake Dobkin NEVER MET 79. Jim Spanfeller NEVER MET 80. Dina Kaplan, Joel Smernoff Who doesn't know them? 81. Daniel Klaus NEVER MET 82. David Jackson - NEVER MET 83. Howard Morgan, Josh Kopelman - Met at NY Angels meetings and on the other side of the table from Josh. 84. Bernard Gershon - NEVER MET 85. R. Michael Leo Met at a breakfast and some other tech events 86. Ben Lerer - NEVER MET 87. Sanford Dickert Another "who doesn't know..." guy. 88. Graham Hill - Met at Laurel's breakfast 89. Lindsay Campbell - Interviewed by Lindsay for WallStrip... accidentally, but still counts. 90. Roger Ehrenberg - Path 101 angel 91. Daphne Kwon - Met at USV 92. Simon Assaad, David Carson - NEVER MET 93. Robert Levitan - NEVER MET 94. Kenny Rosenblatt - NEVER MET 95. Herb Scannell NEVER MET 96. Andrew Rasiej - Met at various tech events 97. Allen Stern - Met at meetups and nextNY events 98. Richard Fernandes - NEVER MET 99. Scott Kurnit - NEVER MET 100. Amol Sarva - NEVER MET

 

Bonus: The Newcomers list

Ariane de Bonvoisin, First 30 Days - Met her at Laurel's breakfasts, but she's lovely.  I'd meet her again in a heartbeat.
Jonathan Butler, Brownstoner - NEVER MET
Court Cunningham, Yodle - NEVER MET
Rich Greenfield, Pali Capital NEVER MET
Darren Herman, The Media Kitchen - Played dodgeball with and against him, and he's a Path 101 angel
Mike Hudack, Blip.tv - Met lots of times - cool guy
Alex Iskold, AdaptiveBlue - Met several times, part of the USV fam
Michael Jackson, IAC - Never met
David Karp, Tumblr - Met...  Meeting David at the W should be on everyone's NYC tech scene todo list.
Alexis Maybank, Gilt Groupe - NEVER MET
Caroline McCarthy, CNET - She needs to play dodgeball with us... obviously met.
Douglas McIntyre, 24/7 Wall St. - NEVER MET
Scott Meyer, About.com - NEVER MET
Betsy Morgan, Huffington Post - Just met at Laurel's breakfast
Chris O’Brien, Motionbox - Met several times
Anand Subramanian, ContextWeb - NEVER MET
Andrew Weinreich, MeetMoi - Met at USV
Nate Westheimer, RoseTech - Duh
Bryan Wiener, 360i - NEVER MET
Benjamin Wolin, Waterfront Media - NEVER MET
Jeffrey Zeldman, Happy Cog Studios - NEVER MET

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

Sign us up, VC Mike: The Burn/Risk Ratio

Mike Hirshland nails how I feel about the timing of Path 101 (except for the market part--there are more people trying to figure out what to do with their careers than you can shake a stick at):

"For the immediate future, what makes sense is to iterate and experiment. During this phase, product, market and adoption risk remains high. The idea is to learn as much as possible about all three of these, and remove a big chunk of these risks, but to burn as little capital as possible during this phase. In the experimentation phase, we want to learn a ton but spend a little.

Once we think we have learned what product will get adoption in the market, and how we will make money from this product/market match (which nearly always takes a few more iteration cycles than originally thought), we then should kick into execution mode, in order to get real live proof points that the model actually works in practice. This is the time to staff up with the team necessary to go to market.

But until then, no need for the bus dev and sales guys that had been in the plan."

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

Smart thinking about alumni social networks

"Telling alumni what tools to use, and how to use them is old school, and they won't care one way or the other that we have certain information on our web sites...We must let alumni build their own online activities, using a framework we provide for the purpose of enabling that process."

- Andrew Shaindlin - Alumni Futures

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

What do the right investors do for you? Summize vs. Tweetscan

There's often a bit of anti-VC sentiment among the entrepreneurial community.  You hear how VCs just want to smash you down, force you out, control your company.

So when the news was officially confirmed that Twitter bought Summize, I got to thinking about Tweetscan.

Tweetscan came out with their Twitter search earlier than Summize--who changed their product model.   However, it was Summize that went out and took some funding ($750k) from Betaworks

Tweetscan seems to have remained a one man show--built by David Sterry, who remarked recently that "Running a search engine is a very hardware intensive task and it's a challenge to keep it fast while providing the results people want."  Tweetscan seemed more like a really interesting side project than an attempt at company building.  Maybe David wasn't looking for anything more.  That's fine.  It was a great project, but clearly now that Summize IS Twitter Search, it will likely become the default.  By the looks of the traffic, it already had:

 

 

Not only was Summize able to build a team, but they got some really thoughtful, well connected investors on board.  Their investors and advisors helped them with the decision to focus on Twitter search--which was a reapplication of their technology away from generalized web sentiment.  Of course, not to mention the fact that John Borthwick says specifically:

"The deal started with a conversation with Fred Wilson about how conversational search can evolve into navigation, about how important navigation becomes for UGC as you go mainstream — it concluded with the deal that was announced this morning. Betaworks is now a twitter shareholder, and excited to be one."

So, when your investor is having this kind of smart conversation with an investor in one of your likely acquirers, you're at a HUGE advantage.  This isn't someone pitching your company to get flipped--this was some pretty high level thinking (and outside the valley thinking, I might add).

So while you're protecting all your equity from those big bad investors, ask yourself the question of who's having these types of conversations with key decision makers and thinkers about your company.  "Who's a lot more experienced than I am that thinks intelligently about my company's strategy--and cares about it?"  

THAT's the kind of investor that makes the rest of your equity worth multiples of what it is the moment they take their 20-30%.

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

Fun with data: Personality Test Dropout Rate

One of my favorite things about actually having a live site up at Path 101 is having user data to play with.

Since we started broadcasting the availability of our personality test, we now have some neat data and feedback on it--like the fact that some people think it's too long.  That begs the question of wanting better data or more completed users... and whether or not there are some people who just won't do anything longer than a minute anyway.   I'm sure we could shave a few questions here and there, and provide some better motivation to strike a balance, but here's what we've got so far:

 

So basically, if we can get someone to the midpoint of the test, they're going to finish.  I don't now if that's normal for these kinds of tests, but that's about what I would expect.  At the end, about 52% percent of the people who started on Page 1 actually finish it.  That's pretty good for a 90 question, 25 minute test.

One thought might be to move some of the "filling buckets" to the front of the test.  People seem to really like those and mixing up the questions better might break up the monotony of the test.

Perhaps some teasers, too... like telling them we've found some industry matches for them, but they have to finish to see them or something. 

Any other ideas?

What about letting people save it midway?  Will you lose people who would have otherwise finished it?  Will people really come back?   Certainly that might drive registrations.  Time for testing!!

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My Path 101 Personality Test Results

There are certainly a lot of places out on the web where you can take a personality test, but for the more serious ones (not the Superhero test), comparing results to others isn't always easy.

That's going to be our next update to the test... the ability to compare your results with other people.

For now, though, people have been sending me screenshots of their Path 101 personality test results and asking me what I got on mine, so I figured I'd share:

Interesting that I'm empathetic, but kind of emotionless.  "I understand your problems, but I just don't care about them."  :)

What did you get on your test?

Haven't taken it yet?  What are you waiting for?  A Beta?  :)

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

Twitter buys Summize

MediaEater said so, but he got scooped by some dude with 3 readers.

 

I suppose it was just easier to buy it out than to distract themselves with their attempts to fix their scaling issues by building something new.

Plus, I imagine it came pretty reasonably, because at the end of the day, they could just decide to shut off the API for Summize and then where would the company be? 

Updated thought:   Who the hell is Josh "3 readers" Chandler and how'd he get this scoop?

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

An experiment: Who's really out there and how do you measure influence?

Fred brought up the issue of deceptive statistics today--RSS readers, Facebook app installs, Twitter or Friendfeed followers, etc.  I'll add one to the mix.  Registered users.  You name the social network and chances are I'm a registered user on it.  Check to see what I've actually logged in to in the last month--very very different numbers there.

So what are we really talking about?  People who are concerned with such numbers are usually trying to figure out and compare influence and perhaps maybe engagement.  If the people reading aren't doing anything, either passing your message on or responding, what's the point of having readers?

That made me think about my readership.  What do all the numbers mean?  Do I really have 2600 readers?  How many of them are really paying attention?  What about twitter followers?  LinkedIn, AIM, etc?  How big an impact could one really make?

So, I've decided to make this post an experiment.  I'm asking you to please link to this post, digg it, tag it in del.icio.us, Tweet it, retweet it, triple tweet it, Stumble on it....whatever.   And please comment the hell out of it, too.  Blog about the idea on your own blog...  blog about the concept of influence... just make sure you post a link.

In fact, if you read this post, please leave a comment on it and tell me how you found it.  Were you reading anyway or did you see it somewhere else?  Where?  If you're new here, did you know how I was or am I new to you?

What I want to do is see where people wind up coming from, how many links in I can get to it, and where the engagement (if any) comes from.  I'll post as much as I can learn from all the linking and traffic after a couple of days--like who drove the most traffic (with links back, of course), what service drove the most traffic, etc.

Can I just will myself up to the top of Techmeme?   (Or will you to get me there, rather?)   del.icio.us popular?  Digg popular?  How much does it take?

Ok, ready, go...  Swarm!  Swarm!

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

Why there will never be "One Ring to Rule Them All" in web services for groups

I'm involved in more groups than you can shake a stick at--in a leadership capacity in most of them.  Being a web guy, I've always been struck with how poor the offerings are for managing groups--particularly within other social networks.  LinkedIn, MySpace and Facebook groups do little to encourage engagement within the application beyond the join.  Most are pretty inactive--a lot of missed potential if you ask me. 

Why, though?  Why is it that no one's been able to come out with really great group software?

Thinking about the groups I'm in gives me an answer. 

Let's start with nextNY.  For one, we wanted a strong brand identity, which meant the ability to control look and feel, and live at our own domain.  That's pretty much why we didn't go with a Meetup group.  On top of that, when we first started, we also wanted both a website and a listserv, and no site actually offered that functionality.  Now, Meetup does, which is great.  Still, Meetup doesn't offer the ability to post blogs from the group, which nextNY didn't even want at first.  Then we realized what we really wanted wasn't just a blog, but a way to aggregate the blog posts of our members that were already being posted.  Perhaps its better that Meetup didn't offer that, because offering a full fledged blogging platform when others exists seems like a waste of resources--especially to a bunch of geeks who were bent on using Wordpress anyway.  Perhaps that would make more sense for a Grandmothers Meetup group in Des Moines.

We thought we wanted several types of aggregation--to aggregate events, Flickr photos, Twitter messages, links, etc.  Then, we realized that the group had gotten so big that some of those things weren't as relevant.  Just because someone is in the group of 1700+, doesn't necessarily mean I want their del.icio.us links or to see their Tweets.  What if they're a hardcore C++ programmer?  That's not so interesting to me.  Well, so maybe we don't want that much aggregation.

You seeing a pattern yet?  Different groups want different things.

The group of Downtown Boathouse volunteers I belong to does not want or need a discussion listserv.  Most of the members already belong to paddling listservs elsewhere--no need to reinvent the wheel. 

At the same time, my sports teams--also groups--need some really kick ass scheduling tools, with smart RSVPs to tell everyone when a critical mass of people has not been achieved for a game.

My group at work uses Chatterous.  We love it.  It's a really simple way of doing group chat where each person can have their own input mechanism.  I can text from my phone or e-mail while others use Jabber--kind of like how Twitter works, but closed for a group.  Does my ZogSports softball team need that, not at all?

There's a company called Wild Apricot that has a cool web service for associations and professional societies--and yet even with a targeted audience, the entrepreneur behind it told me that they have a feature request list as long as your arm.

The point is, every group is different, so the idea of one particular group software solving everyone's problem is never going to work.  However, I do think there are a few things that most groups would want out of a web service:

  1. A customizable site to call their own, even if it just has information as to what the group does and how to sign up.
  2. A way to communicate internally, via a one-way or two-way listserv, depending on the group.
  3. A way to do RSVPs for events.

Right now, only Meetup has all those features for general kinds of groups.  Sportsvite has that for sports teams.  However, I'll tell you that most groups do just fine by using Eventbrite to do RSVPs and a combo of a blog or site for their group and a Google Groups or Yahoo Groups listserv for communication.  It's not that hard, and besides, it's the web.  Your users are going to use lots of different tools for lots of different tasks--you can't solve all of their problems, nor should you attempt to.

Still, it is sort of bewildering that functionality in Facebook, MySpace, and LinkedIn groups is so lacking.  If any one of those companies improved their group tools, I think that could be very powerful, because they already have the networks built in.

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

Friendfeed replacing Twitter? Yeah, and sometimes when I want an apple, I eat fish instead.

"Perhaps my lack of enthusiasm for Friendfeed has to do with my goal to reduce the amount of digital noise..."

Mark Evans nails exactly how I feel about FriendFeed in his post: "The Digerati’s Love Affair With Friendfeed".

He points out how Haterington says people are just moving from Twitter to Friendfeed, because of Twitter's scaling issues.

For the 99% of us on Twitter who don't follow 8,000 people, that makes no sense at all.  I get a big chunk of my tweets on my phone, because I like knowing, in short, real time snippets, what my actual friends are up to.  That's what I think of Twitter as.  Do I need to know, on my phone, in real time, when they all post photos, blog posts, favorite music, comment on other people's blogs, etc... Yeah, not so much.

To me, they're two totally different apps...not even close.  Friendfeed is basically an RSS reader for the social actions of a critical mass of people--all of their social actions.  It's built to be a firehose--a completely out of context firehose of all sorts of different content.  Twitter, on the other hand, is built off of short messages in real time.  How this is supposed to be a replacement for Twitter I have no idea. 

How exactly does FriendFeed help me meet up with people at the Shake Shack...like now? 

I think some of the digerati need to understand that they don't use these applications like most of the rest of us who are using them do, and that even just being in the groups that do mean we're a small segment of the population.

Call me old fashioned, but there's a group I want to see Flickr photos from, a group I want to share music with, some people I want to see the tweets of, and so on... and these groups hardly overlap at all.  Not only that, I want a relevant set of features in each context..."loving" certain songs, sending certain blog posts to del.icio.us and labeling certain photos with funny notes. 

FriendFeed seems to cater to the same kind of crowd that treats content consumption and audience creation like some kind of contest that involves belt unbuckling and rulers. 

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

Buried in your own startup? Who's going to get buried in yours?

When's the last time you offered help to another startup?  Even if it's just sitting down and listening to someone's pitch for them, or giving product advice, spending a few minutes with someone else's big idea can reap tons of benefits, and not just for them.

First off all, being selfless generates goodwill.  Any time you spend on someone else's project will be more than reciprocated when you need something in return.  So when you're looking for people to invite their friends and spread the word about your app, don't be surprised when your strongest supporters are the guys you went to lunch with last week to be an elevator pitch sounding board.  I think too many people bury themselves in their own work, and then when it comes down to needing a supportive community to grow their service, they find a lot of tumbleweed blowing through their social graph.  Don't expect to disappear on your friends and fellow entrepreneurs for months on and and then expect the cavalry to arrive when you need a Digg.

Secondly, pulling your head out of the sand once in a while can inspire you.  I make it a point to spend time with entrepreneurs who work in other verticals, because you never know when an idea that works somewhere else can be reapplied in a novel way.  I don't spend all of my time in the job space because it contains a lot of the kind of stagnant thinking I want to disrupt with Path 101.  Some of my best ideas have come from startups and just other professionals in completely different industries. 

A lot of people cling to startups who seem to be on the rise, but fail to be there for others when things aren't going so well.  Helping someone who is down and out in a difficult time is not only severely needed, because the ups and downs of the startup world can be difficult, but can also put you in the right place at the right time when companies start scuttling themselves.  You might be able to take over a cheap lease, hire your superstar coding buddy who tried to go out on his own but it didn't work, or grab an unwanted server (or two). 

Community participation is also important.  By sharing your successes and failures with others, not only can that raise your own profile, but contributing to a strong local tech community can have longer term benefits.  Maybe it will be easier to hire your next developer down the line because more people will know what you're up to, or the community will just attract more people.  I never thought of any of this stuff when I started nextNY, but I can clearly see a positive ROI to my participation.  If it wasn't for nextNY, I never would have found my partner Alex, because I caught up with him at a couple of community events right after he left his last job.

I don't know if this makes me sound insincere or not--I'm just trying to point out to those who wouldn't normally take their eyes off their own work that there can be a positive ROI to being a bit selfless.  Not everyone is naturally this way, and so sometimes people need to see incentives, which, to me, is fine as long as the help is authentic.

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

Free Business Plan: Coffee Shop WiFi Social Network

In your local coffee shop, there are probably tons of interesting people around you--all using the free (or not so free) wifi. 

Some of those people may be consultants for hire.  Other people might be doing really cool startups.  The guy next to you may be your best friend's new roommate.  The girl across from you might be your soul mate.

How would you know?

How about an opt-in social network that you login to when you get sent to those Terms of Service pages for logging in to the free wifi.   You could agree to show your profile--which could be a new profile or maybe just an aggregation of your Facebook, LinkedIn, etc profiles anytime you login to that wifi node.

Personally, I'd love to know who's around me when I'm sitting down at a coffee show and I'd be more than happy to display what I'm up to as well.  Plus, I like the idea of making the coffee shop experience offline a lot more social, because you could start a conversation with someone in person based on mutual interests. 

The data about where I tend to login to free wifi could also be used in a MyBlogLog kind of way...  where if I login three times, I automatically get added to that shop's community.  At that point, it would benefit the shop to provide free wifi and encourage participation on the network, because seeing where interesting people or your friends go to hangout would encourage you to show up as well. 

Of course, this means you have to have feet on the ground to get into the firmware/software setup of all these routers in all these random coffee shops.  There's no easy way to get viral adoption here.  It's curious to me why Starbucks never setup the "Your Starbucks" social network, because people have such strong affinities to the one that they go to and often see the same people all the time. 

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

I know what Plinky is going to be: Awesome. That's all I can say.

Alex and I had the pleasure of chatting with Jason Shellen a couple of months ago on the phone--Smart guy and pretty funny, too.  He slipped us some info on what Plinky was about and I think it's very cool.  I can't wait to see it.

Interesting that Polaris funded the seed round.

With a guy like Jason, there's little risk of execution or that the technology won't work.  Plus, getting adoption is part of an iterative process--the crowd rarely loves you on your first pass--so why not fund this early?  If you like the entrepreneur and their vision, I don't think a couple of months of traction with bootstrapped or angel resources really proves much of anything.

Good luck Jason!  Send an alpha invite our way!

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

Pay to Listen: Is the Sermo model the answer for monetizing communities like Twitter, Get Satisfaction, and Tumblr?

For those of you that don't know, Sermo is a social network for doctors to share information, insights, and advice with each other.  You would think, given such a high quality demographic profile, that driving advertising revenue would be like shooting fish in a barrel.  What pharmaceutical company wouldn't want to get their ads in front of doctors talking to each other about medicine?

Of course, what doctor really wants to join a social network full of pharmaceutical ads--not to mention how likely are they to click a banner ad about drugs?  (Although they might be able to sell a list of the doctors with the highest clickthroughs to patients, so I know who NOT to go to in an emergency.)

Unfortunately, given current ad formats, monetization through advertising directly flies in the face of the quality of interaction in the community.  It degrades the user experience, creating a problem for startups.

Instead, Sermo is making the user experience a priority, ridding their site of ads, and instead, allowing financial investors, government agencies, and yes, the pharma companies, an opportunity to observe the interactions and pull useful insights out of the community.  Instead of taking their customers out of their natural environment to do surveys and research, they're making the whole community into a huge research panel.

The value to the institutions that live and die with drug approvals, potential recalls, new patent uses, etc. is unquestionable.  In fact, Sermo should become profitable this year, after securing almost $40 million in investment.

Does it really take that much money to build a social network?  No, but these types of information creating communities are requiring a second phase of build--tools to secure and to harvest the data, as well as a more robust infrastructure to scale the community and insure it's continued growth.

This is an interesting potential path for communities like Twitter, Get Satisfaction, and Tumblr.  On their face, it might not be obvious to folks how they'll ever drive revenue, especially since these aren't necessarily places people want to be sold to. 

The information coming out of Twitter is a gold mine--whether it's about brands, stocks, events, music, etc.  I'm a bit surprised that Twitter hasn't done more along the lines of search and trend tracking, but I suppose their amazing growth has given them more immediate fish to fry.  Anyone who's ever tracked a consumer brand on Twitter knows that a marketer or brand manager would pay through the nose for this kind of insight into customers in the wild.

Get Satisfaction--the community powered customer feedback portal--is creating a place where people can tap into their userbase and understand issues, problems, opportunities, etc.  Since the Kryptonite lock incident, companies have realized that social media engagement isn't a choice--it's a business necessity, and yet great tools for engagement and participation haven't really been built until GetSatisfaction.

I love the fact that customers can create pages for the companies they love or hate even before the company joins the network.  Not surprisingly, many companies will be the last ones to the party, but what this model also does is to give the company a great pipeline for who to sell to next.

Tumblr may wind up with a similar model, especially if it continues to be a place where cool people share cool things on the web.  I don't know of they can continue to maintain this atmosphere and scale at the same time, but if they can, there's surely a lot of interesting trend data that can bubble up from Tumblr. 

In a lot of ways, this model is just like the way Google monetized search.  You built a place where people could get something done or solve a problem for free--try not to interrupt their experience, and then try to harvest the data their participation created. 

There are, of course, several challenges with this model.  First is that the visionary community person who created the community may not be the same person tasked with building the application that packages the data and the participation tools for the entity that ultimately pays for the service.  Of course, it's integral for the visionary community folks to be a part of this process to protect the interests of the consumers, but ultimately, you need an industry person to really understand and service the needs of the pharma companies, Comcast, or the brand marketer, whoever it may be. 

Second, investors may have to make a kind of leap of faith about the value of the data and the ability for the team to build a product that gleans valuable insights from it.  Whereas now they don't have to make much of a leap of faith as to whether or not there's user value in these free applications, the chasm has shifted to betting on whether or not the business information seekers will buy in.

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

Call for Topics for Startup Workshop at Web 2.0 Expo in NYC

Albert Wenger and I will be moderating a three hour startup workshop at NYC Web 2.0 Expo in September. There is a lot we could talk about from getting started to hiring to fundraising. But rather than just pick the topics ourselves based on what we think might be interesting, we figured we should find out ahead of time what folks really want to hear about. So please use the comments to suggest questions, topics and even guest speakers (three hours is a long time and we will vary the format including break out sessions).

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

5 things you need to do to turn a napkin into a company

Growing a startup isn't easy, but at least once you're up and running, you're more likely to get outside feedback and suggestions. When all you have is an idea, it's often hard to figure out where to begin. Here are five things I tell napkin stage entrepreneurs all the time:

 

1) Have great relationships with the people who know you already.  If the people who have either worked for you or that you've worked for won't vouch for you, who will?  Investors, employees, and partners are all going to look for this.  So, before you spend the next 6 months trying to pound the pavement trying to drum up new relationships, how about spending half that time with the successful people who know you already?


2) Join the conversations already going on in your space--read blogs, start a blog, join groups, listservs, attend meetups. There are a bunch of reasons for this. First off, unless you're actively engaging with thoughtful people in your industry on a daily basis, it's going to be extremely difficult to be as current as possible on the trends that affect your idea. Plus, engagement in conversation, both online and offline, will attract likeminded thinkers, which you're going to need when you get your idea off the ground.


3) Use every single even mildly related service you possibly can--and not just once. You need to have a really thorough knowledge of what else is out there--not to defend your idea and explain why it's different, but to learn from (copy, improve upon) the best ideas the market already has, and understand what isn't working about the ones that fail. I can't tell you how many times I mention a related company to a startup and they've never even heard of it. I shouldn't know more about the startups and existing services in your space than you do.


4) Identify the 30 most knowledgeable people in your space--analysts, investors, executives, even competitors--and try to meet with them about your idea. Look, all you have is an idea. Chances are, all of these people have thought about or heard of your idea before, and they have existing day jobs, so they're not likely to just jump in and steal what you're doing. When anyone can copy your idea in a matter of weeks, it's a matter of execution anyway--and that requires all the best thinking you can muster. Plus, chances are that some of these people will put you in touch with people who could help build your idea, through collaboration, investment, or even literally code it up.


5) Be a leader of startups in your space. All startups need some basic help with the nuts and bolts of running a business. Gathering a critical mass of other startups doing similar things allows you all to learn from each other and focus on the parts of your business that creates value, not stumble on the basics. Also, putting together events for new companies in your space can attract potential clients, who may want to checkout a bunch of startups all at once. A good example of a group of new startups in a single industry coming together to help each other and learn is the new Fashion 2.0 Meetup group here in NYC. They're sure to attract more industry speakers, investors, etc. as a group than any one of them would have been able to individually. Competition? Sure, some of them may be competitive with each other, but better to know and have a dialogue with the enemy than not.

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

Donna Bogatin, what's your glitch? Startup Hater's personal vendetta against Fred Wilson is bewildering

Oh...  I mean... Chatter.

In my old apartment, I had a huge desk up against a wall that, I admit, I never really moved.  When I finally went back there to sweep, I found some fuzz and bones that, at one time, was a mouse who chewed right into an extension cord and zapped himself.  Had I never swept up back there, I never would have noticed him.

In the same way, I'd never notice Donna Bogatin's blog, "Startup Chatter" either, except that she constantly links to TechMeme stories, making her one really angry pilot fish who never generates her own insights.  That's the only way I know that she's still blogging, and still, for some bizzare reason, hating on Fred Wilson and every Union Square Ventures portfolio company.

Her latest target is Daniel Ha and Disqus, which just launched at the end of last October.  She rips on both the company and Fred, who backed it, because of a "spoon-fed puff piece" that appeared about the company on Louis Gray's blog.  She attacks Fred for being "consistently, disingenuously mum regarding meaningful insights about achieving what really matters to the investors in all of his portfolio companies: A BIG PROFIT ON THEIR INVESTMENTS".

This is what bothers me.  The Brooklyn boy in me gets pretty pissed of when she calls Fred Wilson "disingenuous."  Fred's been a mentor, friend, teacher, and supportive angel investor, and it just irks me to see her talk trash about a really great guy--and a great investor.  After taking her to lunch a while back to try to open up a dialogue, and then promptly getting ripped on again the next day, Fred doesn't bother with her, but I can't let this go. 

Why?   

Because Fred Wilson and Union Square Ventures (along with David Hornick's VentureBlog) opened up the world of venture capital investing to entrepreneurs in a way that no one had ever done before--not with PR speak, but with an honest and sincere day to day account of the behind the scenes thinking that goes into running a venture fund.  Plus, he's consistantly one of the most insightful bloggers out there and, unlike Donna, full of original and useful ideas. 

Donna's big gripe about Union Square Ventures is that she thinks they're not focused enough on building real companies with real revenues.   Has she even looked at their portfolio?  Of the 19 investments that they've made, at least 6 of them (FeedBurner, Etsy, Indeed, Oddcast, Tacoda, and Instant Information) were generating multiple millions of dollars in annual revenues.   Of the other 13, del.icio.us was sold 9 months after USV invested, which was the choice of the founder and majority owner, but could have been built up into a people powered search engine (which, last I checked, is a real revenue model), 4 are recent investments, and the rest are in various stages of building up scale--a necessary requirement for significant revenue generation for some of the plans of these companies.  (Google had to get to signficant scale before they had enough
search traffic to monetize against.)

And the silliest thing about her comments is how she speaks on behalf of the USV investors about what really matters to them.  Nearly all of the USV investors reupped in the firm's next fund.  With exits in Tacoda, Feedburner, del.icio.us, and nearly guaranteed (b/c of significant revenue traction) big exits in Indeed and Etsy, not to mention the potential of their other portfolio companise, USV's doing just fine in terms of creating revenue generating businesses and ones with successful exits.

So, basically, she has no idea what she's talking about. 

Actually, that's not the silliest thing about her comments.  The silliest thing about her comments is that she's now trying to make a business helping NYC startups as an advisor.  How wise do you think it is for someone advising startups and offering to make introductions to VCs here in NYC to constantly rip on the #1 VC firm in the city?  If that's the kind of advising she gives herself, I'd hate to hear what she has to tell startup companies. 

That's part of the reason why I feel the need to respond to her comments as well.  Ever since I started nextNY, I feel very protective of the NYC startup community and I've been really wary of self-proclaimed experts looking to profit off of newbie startups--especially when you can get these services for free.

If you're a NYC startup and you want feedback on your pitch, biz plan... anything...  You can join the nextNY list and just ask for a small group of folks to meet up with you about it.  What you'll get is an experienced group of current entrepreneurs, investors, developers, etc. who are part of the over 1700 folks involved in nextNY.  They'll be happy to sit around a table with you and give you excellent feedback on your idea--better feedback than I'm sure you'll get from the crazy cat lady of the NYC tech blogging community. 

I can't wait until she rips on Path 101--that will surely generate tons of unintentional humor. 

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It's My Life, Venture Capital & Technology Charlie O'Donnell It's My Life, Venture Capital & Technology Charlie O'Donnell

Just added a Twitter counter to my blog? Are you following me?

Right now, I have 2653 RSS subscribers and 890 Twitter followers.

Assuming not every one of my Twitter followers follow my blog via RSS, I'm going to say that puts Twitter penetration in my blog audience at about 25%. 

If you're not on it, check it out, particularly if you just don't get it.

 

What's the point of it?  It's a short form conversation that's going on between blog posts.  Think if it this way:  It's the "hallway track" at a conference--when the best conversations are the ones had spontaneously over on the side, away from the main exhibit room.

So before you think about whether you want to publish when you brush your teeth to the world, think about it from the listening perspective.  You spend the time to read my blog, where the posts are often entirely too long--why not find out about what I'm thinking and who I'm talking to when I'm not blogging?

It's time to listen in on the hallway track.  I'm here on Twitter:  http://www.twitter.com/ceonyc

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