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

Wannabes vs. Thinktheyares

I'm a wannabe.

I wannabe a successful entrepreneur.  My definition of success is making a big positive impact on a lot of people's lives.  If I accomplish that, I'm sure the money will come, but in the words of Zuck, "I'm not really focused on that right now."

I wannabe a better person tomorrow than I was yesterday.

I wannabe someone that inspires others to go after what they really want.

Being called a wannabe isn't that bad.

However, I heard the term used to describe a local outspoken entrepreneur in a less than endearing way and I didn't quite see it as accurate.  The reason why this person rubbed others the wrong way wasn't because they were a wannabe--because that's not so bad.

It was because they were a "thinktheyare". 

There are definitely too many of those around for my taste.  The last thing in the world I think anyone could accuse me of is being a thinktheyare, because it's so incredibly important to give credit to the people around me and I feel like I'm incredibly fortunate to have such great people around me.  Anytime anyone tries to throw credit my way for something, I try hard to figure out who else helped get me somewhere, because I don't think I'm much more than someone who has a great circle around them.

When word of mouth is faster and cheaper than it ever has been before, the self-marketers really come out in full force.  Sometimes, it's tough to really figure out who's legit and who's just blowing smoke. 

But it's pretty clear to me who is a "thinktheyare" and I'll tell you that there's usually a strong correlation between being a thinktheyare and a smoke blower.  

Here are some easy ways to spoke a thinktheyare:

  1. They like to tout the fact that they are the "only" or "first" person to do something.
  2. It's never clear exactly what they did and where they did it.  You've often never heard of the companies they've worked with, or they namedrop with companies, but the exact role and what they accomplished is often unclear.
  3. Thinktheyares are often attracted to or try to create artificial scarcity.  If they see something as being exclusive, even if it seems pointless as to the advantages of exclusivity in that situation, they're on it. 
  4. They need to get their name attached to everything and they try to make everything "bigger". 
  5. They speak at a lot of events, but when you ask startup pros who they'd want to do a particular job, the thinktheyare is never at the top of anyone's list for whatever their supposed expertise is.
  6. They have a lot of "associations" with people... but as for strong two-way connections, the jury is out.
  7. Thinktheyare's often feign help.  They tell you they'll hook you up with something, but it either never quite comes through or seems to come with some kind of unforseen string attached.
So, you should strive to be a wannabe.  Everyone should wannabe something and hopefully, actually be in the process of being that...   but just don't be a thinkyouare, because, well, you just aren't, whatever it is.
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It's My Life, Venture Capital & Technology Charlie O'Donnell It's My Life, Venture Capital & Technology Charlie O'Donnell

We all have stuff

For the last few days, I've been thinking about a professional acquaintence turned new friend... They have a family member with a serious health issue, which happens to everyone at some point or another.

I was struck because, when I spoke to this person, she was more concerned with letting me get back to my business than what was going on in her life. I couldn't do it. I couldn't say, "Hey, um, yeah... sorry about your sick uncle...I gotta go return some important e-mail."

E-mail! "F" e-mail.

If it's important, they'll call. People don't call anymore. You know why? It's never important...not as important as a friend with a really serious problem.

I have another friend who recently busted a wheel on her car swirving out of the way of a pothole. It was raining and late at night. Rather than call anyone for help, she slept in the car in a parking lot until morning and then called a tow truck.

Have we gotten so low in our expectations of people? Have we gotten so self absorbed that we give off the impression that we can't be bothered with any kind of personal inconvenience?

At the end of the day, I want to deal with people who not only think I can make money for or with them but who care about me as a person. Our monthly board meetings include a few minutes for "How are you guys doing?" To me, that's almost the most important part of the meeting, because we're building applications for people, leveraging people, empowering people...if our own people aren't doing so well, it is highly unlikely our people centric application will amount to much.

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What do Tom Glavine and Sarah Lacy have in common?

When Tom Glavine joined the Mets, he was a career Atlanta Brave.  The team had been a playoff mainstay for a decade and he had won a championship with them. 

Instead of continuing to help his team, he opted to take a few million a year more on what would have been a $10 million a year offer with the Braves.  Another factor was the Met's option for a 4th year, which gave him a better shot at 300 wins.  Basically, it was a completely selfish decision.

Mets fans knew he didn't really want to be in New York from the start.  So, not surprisingly, when you prove yourself to be selfish and looking out for #1, then your audience is going to have very little tolerance for anything but perfection.  If you're shooting for millions and a personal milestone, you have to deal with the downside as well as the upside.

He had a pretty mediocre Met career, but Glavine's fail came at the end of the 2007 season.  The Mets were on the brink of one of the worst collapses in sports history, but all they had to do was to win a single game down the stretch to force a playoff... and two to get in.  Glavine's last two performances were abysmal.  Against the hapless Washington Nationals on September 25th, with the Mets still up 2 games, he gave up 6 runs in 5 innings, getting outduled by Justin Bergmann.  Fail.

Nuclear fail came on the last day of the season, when the 300 game winner could only record a single out.  He faced nine batters.  Five got hits.  Two were walked, including a plunking of Dontrelle Willis, the opposing pitcher.  Seven scored.  Thirty six of the worst pitchers he had ever thrown in his life--only 17 of them for strikes.

But the worst part about the whole thing was his response after the game.  He said he wasn't "devasted" and that was a word he reserved for life and death situations.  What Glavine didn't get was that many fans feel like it is life and death when they watch a team... it's certainly bigger than just a game to them.  Regardless of what he felt like on the inside, as a $13 million a year entertainer, it shouldn't be too much trouble to feign a little devastation for the fans sake.

In fact, he never showed much emotion at all, and that was the worst part of it.  It wasn't just that he failed... he never really seemed to acknowledge it.

Similarly, when Sarah Lacy got to interview Mark Zuckerberg at the SXSW keynote--conveniently close to the timing of her book about the company--she put herself in the spotlight.  It was a huge opportunity to step up.  A fantastic interview could have meant some great wind at her back for book sales and certainly a nice notch in her journalist belt.  It reminded me of when Kara Swisher had an opportunity to get inside AOL during the late 90's on the way up her great journalistic career.  Sarah Lacy could have been the next Kara Swisher.  Instead, we sat there wishing it was Kara Swisher doing the interview with Mark.

She failed to bring an already uncomfortable young founder out of his shell.  She failed to pick up on what the audience wanted out of the interview.  She patronized and then even seemed to flirt with Zuckerberg during the interview.  I sat there in person... it was like watching a car accident.  Arrington thinks people are being sexist, but girl or guy, flirting is flirting.  If Robert Scoble did the interview and started twirling his hair at the mention that Mark is the youngest billionaire, everyone would have said, "WTF...  Is Scoble flirting?"  It didn't have a place no matter who was interviewing.

Even my friend Ariel, who is most definitely a woman, said it live on Twitter:

"Can't tell if Sarah Lacey wants to flirt with Zuckerberg or interview him the leg bouncing and hair twirling enough!"

Eventually, I was so uncomfortable that I had to leave...  I'm sorry I missed the end when she attacked the audience, but her video comments afterwards were as equally obnoxious as the interview.  She said that she made the mistake of coming to a "developer's conference".

I'm not a developer.  I didn't want to hear about the specifics of API's either... but "You don't believe Facebook is really worth 15 billion, do you?"

What kind of question is that?  What's the expected answer?

And, "Beacon, WTF?"

I'd like to just to interviews like that...   Maybe I'll get to interview GW and I'll just say, "Iraq, WTF?"

Eliot Spitzer interview, "Hookers, WTF?"

Certainly more efficient.  Why waste words?

And let's keep in kind that this is someone who, just a week ago, "asked for the ball" in the big game.  She made a big deal about not getting into TED.  So, she got to step up to the keynote interview at SXSW and she blew it...   hey, you know, it happens, but she's got to own up to it, just the same way she would have owned up to the upside of great book sales, big stories, etc.

Instead, she blamed everyone else but herself.  She blamed the people in the room for possibly preventing any big name people from ever attending again.  Her now famous "screw you all" twitter...  it's Glavine's "this is not devastating" all over again.

She needs to admit that she was poorly prepared for the interview and apologize...   save some face and take some of the hit she's tried unsuccessfully to dodge so far.

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

The Secret Life of Angels: Raising an Angel Round for Your Startup

A lot of people come my way when they start thinking about raising money--either because I used to work for a venture capital fund or because my company, Path 101 just completed our 350,000 angel round.

Without fail, the first question is usually, "Who should I go to?" Many people feel that, especially in NYC, angels willing to invest in early stage deals are hard to find. The entrepreneurs attend "exclusive" networking events to meet angels only to discover that few investors actually attend these events and those that do are often not looking at things in your stage or area.

These are the last places you should look, as far as I'm concerned.

It's the same thing as trying to meet someone great in a bar...   Sure, it happens, but the odds are against you.  They don't know you, you don't know them.   You don't have any idea what the other person is looking for, what they value, or whether they're even really in the market at that moment.  Maybe they're just getting out of a bad relationship, or in an angel's case, just lost some money in a bad deal--in your niche, too.  Plus, in general, there are way more potential angels NOT going to angel events than actually going.  Similarly, the number of single people far outpaces the number of people who hangout in the hottest singles bars and clubs.

There are a few keys to improving your odds with angels, and this advice, not surprisingly, works with dating, too--the big difference is that one of these activities makes you money and the other is likely to burn a hole in your pocket.  :)

First, you want to start a lot "closer to home".  Who knows you the best?  Who trusts you?  Remember that the requirement for an angel investor is that they be accredited investors.  These are basically either insitutions, or if they're individuals, they need to make over 200k a year (300k for couples) or have a million bucks of net worth.  What they don't need is a shingle on their door or business card that says "angel investor".  An angel investor might be the person in the neighborhood you grew up in who owned the biggest house--someone who knew you and your family from a religious organization perhaps.  They could be your previous or current employer, or their boss--just generally someone who knows you well enough to think that you can be trusted, that you'll give it your all, and that you have the skills to succeed.  These should be the easiest people to convince that you're worth backing--and other angels are going to want to see this.

Should that mean family?  Eh...  I don't know about that.  I think you're going to need your family for support, emotional strength...   You're going to need someone to turn to do say, "Wow, things are going really bad, I'm really worried." and I don't think you want to eliminate the possibility of being able to say that to your family, because they've got their retirement funds in your startup.

Depending on your industry (this of course might be tough if you're a social worker), I've often said that if you don't have enough industry experience and enough of a network to have at least $150k of relationships on your own, I'm not entirely sure how successful you're going to be in starting a company.  Even in the early going, it's really obvious how much success hinges on the company you keep.  There's just too much to do, too much to know...  I don't know how any entrepreneur who doesn't know at least a handful of more successful people than them can do this job, frankly.   You need to know people in the space who are willing to go to bat for you--those are the people likely to fund you.

On top of that, I can't overstate the value of industry expertise.  If a startup has literally zero connections to money, that probably means that they don't necessarily have a lot of experience in their particular industry. Otherwise, they would have known SOMEONE who made money in it.   In my mind, that's a problem.  Even the most disruptive business models require at least a little bit of industry know-how...  of nothing else than to know exactly how to be disruptive and deliver the deathblow to the old school companies in your space.  You need to know the landscape, how money flows, how value is created... 

And you get this experience not just by having any job in your space, but by actively being a leader in it--taking on responsibility, leading people like you with similar interests...  Again, also like dating.  Instead of always looking for dates, if you're just getting out there, being active in your social life and hobbies, you're more likely going to come off as the kind of person people want to spend time with--and in the angel situation, who people want to spend money with.  If you weren't a "entrepreneurial" before you started your company, whether in your hobbies, volunteer activities, student groups, professional orgs, what are the chances that you'll be successful in this startup--your first real leadership challenge?

So, ideally, you've got some connections to successful people in your own industry.  Your target angel list should include the top 30 most successful people you can find in your space--not that you want to include all of them in your deal, but you need to talk to a lot of people because you're going to get a lot of no's.  The biggest reason why you want these people in your deal is because they can vet your idea.  If you've got an idea for a retail concept, and the founder of Jamba Juice invests in your company, clearly that means a lot and that you're probably onto something.  You still could fail, but at least and "insider" has deemed your idea not to be completely stupid.  If you can't convince any of the 30 most successful people in your industry to back you or you can't even network your way to them, I'd say that's a big issue.

When you actually get in front of these folks, don't discount what they can offer besides just a check.  We got a ton of value from meeting with successful entrepreneurs before our round.  It was great when people inquired about the potential for investment, but even when they didn't, we learned lessons that were just as valuable. 

Someone asked me the other day how to ask?  Do you just come out and say it?  What do you ask for?  A certain amount? 

We tried to avoid asking as much as we could.  If people are interested, they're going to bring it up.  We just basically said, "Here's what we're doing... here's how much money we're raising...  We'd love to get any feedback you have." 

We meant that, too... can't overstate that.  It was great when people volunteered to write checks but you can't expect it..  Even though these were folks that obviously had the money, it's still a lot to ask for and angel investing is pretty risky.  We did, of course, nudge a few people when we really wanted them in and they didn't bring it up on their own.

As for size of the round, terms, etc...  we did find a couple of more sophisticated folks to guide us on things like the security, the price, and then we sollicated lots of feedback from others.  You don't want to have a 8 way (or in our case, a 20 way) negotiation on the docs, so if you can find a couple of folks to commit early, and anchor a fair round, that will make your life a lot easier. 

Number is a big question people have, too.  We had more than anyone else I know...20 people.  I wouldn't necessarily recommend it, but outside of all the paper shuffling, I'm so excited that we've got all these great people involved and helping us out.  Actually, the bigger question was how small an investment were we willing to take.  For what it's worth, we took a few 5's and 10's under the following conditions:  Did they add some kind of unique experience for value?  Or,  were they just nice people wouldn't cause us a lot of headaches to manage?  No reason not to take 5's otherwise, because they day may come when you're down to your last few grand and you'll be glad you took it.

Anyway... that's what we learned...  I'd love to hear lessons from others....

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

What is BricaBox anyway? The elevator pitch you've been waiting for.

Anyone who's ever chatted with Nate about BricaBox often has the same response: confusion.

Nate's a good friend, but he's a typical visionary founder in that he's hesitant to succumb to others' bastardized Web 2.0 analogies of what the product actually does.  Many entrepreneurs cringe at being called the "Wikipedia for this" or "Flickr for that" or "del.icio.us but with blogging".  It goes against the vision--the bigger picture.  They seem to think it cheapens their accomplishment, but I disagree.  People need to compare new things to things they already understand.  It helps them process new ideas.

So, since Nate doesn't have an elevator pitch, I've decided to create one for him.  BricaBox is pretty simple actually.  It is...

"A wiki with depth."

Wikis are pretty flat.  You find a webpage, you click into it and add text.  You can add links, but links just enable you to travel sideways in a flat world. 

BricaBox enables outsiders to add structured content to a page--content that has all sorts of other attributions, like restaurants that not only have locations, but menu items as well.

So... who cares?

Well, any publisher who cares about interactivity, engagement, and pageviews should care. 

There are some brilliant sites out there on the web that are what I call "rotating cubes".  Most sites are essentially databases, but these sites, through their structure, expose all the various data elements to users as separate pages.  Some of my favorites are IMDB, Last.fm, and Baseball Reference.  Every element in their database is a new page, semantically connected to all of the other various datapoints associated with it.  On IMDB, actors are in movies and movies have directors who've done other movies.  You can click sideways and up and down this side forever--and these types of sites often gets lots of pageviews.   IMDB gets 8 pageviews a visit.  Last.fm gets 6.  Baseball Reference gets almost 5.  By contrast, the NY Times gets 3 and Citysearch gets 2.5.   Those are pretty flat sites.

What structured, open content like a BricaBox does is bring your database out into the open, making it crawlable, clickable, and easily navigated.   It's something that any publisher with a structured database should think about implementing, lest all their good data stay below the surface of their web, never to be discovered by users, crawlers, or anything else that floats by.

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Businessperson with an idea for a web startup? Looking to get a tech partner? Read this first!

On the nextNY listserv, there are a lot of businesspeople who think they're just a developer away from a great web startup.  It's certainly possible, but I often find that they haven't really fleshed out their product idea too much.

I'd very very strongly suggest that, before you start paying someone to build anything, you do some extensive product spec work...   talking to as many people as possible about what you're building. 

Hold a few feedback sessions, too...   ask a few knowledgeable people to sit in a room to hear your idea and give feedback on its current state and where it might go.  Be open to their suggestions...and give them pizza!

Here's a checklist of things I would do before paying dollar one to start building:

1) Narrow down your market vertical...   Weddings or adventure sports?  Feature creep is a killer at an early stage and companies often try to do too much.  Your end product, if it comes to market, will be so much smaller than you imagine.

2) Outline 2-3 things you things you want to focus on within that niche..   You'll prob narrow down to one, but keep an open mind about possibilities, because feedback is going to make you alter your idea.

3) Find 5 sites that do at least some aspects of what your site does and use them extensively... like everyday for a week or two at least (ideally longer!)... know all the ins and outs of the service.   Group all their features into a) things they do well b) things I can do better/different c) things we can work together on and d) make a list of things you wish they did.

4) Take all the features and rank them in terms of importance...     This way, you'll realize whether you're building a new mousetrap, because all your top features are category D or a better mousetrap, b/c they're all category B or C) more of a mashup.

5) Take your list and imagine what ties this all together in one site if you can do 1 feature, 3 features, 10 features, etc...  Where are the natural grouping points... and what is the minimum amount of things that gives you a viable site.

6) Talk to 5 high level people in the industry about the smallest versions of your idea and get feedback.   After their feedback, go through this whole process over again.

6a) (Optional)  Blog this whole process openly and solicit even more feedback.

7) Then, MAYBE I'd talk to a contract developer... but only then....    Of course, if you can get someone more technical working on this process with you at no cost.... just to help shape the idea.. that's ideal.


In addition to this, you need to create a plan to be executed everyday that makes you exactly the right person to do this idea.  It will be incredibly difficult to get backing and support for your project unless people feel like you are THE person to do this startup, you understand those industries much more than almost anyone, and have publicly associated your name with those industries.  Starting out by blogging about those industries, maybe running some learning annex courses, a meetup group, etc. is a good start.... because it will sharpen your thinking on the space and attract others with similar or better yet, contrary ideas.

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

nextNY MSM News Coverage Blackout... why?hh

The other night, well over a hundred people packed Antarctica Bar to celebrate the 2 year anniversary of nextNY.  In two years, our ranks have grown to 1500 people, with probably close to 1000 different people attending our events at one time or another. And the group is a neat story in itself.  Anyone can start an event.  There are no titles, everyone is a participant.  The listserv buzzes with questions, comments, recommendations, from a wide spectrum of tech and digital media folks in NYC...  entrepreneurs, investors, designers, developers. And yet, no NYC based reporter has ever written about it. I just read this Investors Business Daily article about how networking groups in L.A. are helping to put that city on the map as a tech center.  We'd love something like that. Besides Caroline McCarthy, we never even see tech reporters at our events...  yet I always get calls from people asking me for intros to cool companies and wanting to know the latest buzz. What gives?    

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

Come hangout with nextNY tonight at our 2 Year Anniversary

Tonight, at Antarctica Bar, is nextNY's 2 Year Anniversary.  Yup, that's the place we first got together back in February of 2006.

Come and catch up with people you haven't seen in a while, people you've never met, or people you'll be hanging out with for the 4th time this week because of all the other tech parties going on in NYC this week.

Antarctica is located on Hudson Street, between Dominic and Spring.   The closest subway is the Spring St. C, E.   We'll start showing around 7PM.

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

What do you name your servers after?

I found out the other day that Alex has started naming our servers after famous chefs.  It made me wonder what other naming conventions people might use, so I Twittered a message asking for people's responses. 

So far, here's what I got:

Rick Stratton
writes, "We always had super heros... Batman, robin, superman... Got down to grn lantern."

Mark Ghuneim writes, "our naming convention for boxes uses people who got away with murder : shug, oj, philspector etc..."

Zelnox added, "We name ours after energy drinks, like redbull and guru. ^_^"

Jason Baptiste chimed in as well.  "famous spaceships. ie- apollo, voyager,etc."

C.C. Chapman names his after, "characters from Shakespeare."


What about you?  What's your hardware nomenclature?

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

Open Letter to Recruiters, Real Estate Agents, Insurance Agents, Accountants, etc...

Dear assorted financial and professional services salespeople who have been contacted me since I announced the incorporation of Path 101,

    No matter how much you try, you all seem the same to me... and the same to every other entrepreneur and new business.  You're selling something and we don't have a lot of money to buy stuff.
    Our initial inclination is that what you're selling we can somehow get on our own--besides which, other than computers, most of us have never made purchases the size of your average bill...  particularly not for services that we imagine the web will outsource, open source, crowdsource, steal, hack, borrow, remix or simply disrupt.

    Let me tell you the story of how one business differentiated themselves in a world where everyone seemed the same, the prices were high, and entrepreneurs didn't quite understand what they were getting...

     When I started with Union Square Ventures, Fred and I were blogging on our personal blogs, and our website was some professionally designed but utterly useless brochureware.  We initially wanted to address the issue of how we prevent our personal blogs from being seen as the faces of the firm and so I made the suggestion that we just use a blog as our corporate home page. 

    It wasn't long before we fundamentally changed the nature of the relationship between venture capital firms and entrepreneurs.  We opened up our process, our thinking, and most of all, we wanted, and got, lots of feedback.  People thought of us differently than every venture firm out there who just had a form or info@ e-mail inbox to dump business plans in.  It became, and remains, a real sustainable advantage.  While other VCs have created their own blogs, to my knowledge, there aren't any firms that have gone the full monty and changed their official corporate presence into something so interactive and open.  It reflects the fact that while there are many individual VCs who think differently about VC relationships, there are few firms who make openness and communication part of the very core of their principles.

     Frankly, it was inspired by the very companies we want to interact with.  Nearly every single startup maintains and gets value out of a corporate blog.  It's how we do our PR, our marketing, our community feedback, and sometimes business development. 

     So, financial and professional services salespeople, why then do you insist on e-mailing us mailing list form letters, or sending us PDF attachments to propriety market research?   I can't reblog a PDF and all your form letters sent from Salesforce look the same.

     I'm busy right now.  Really busy.  I'm running a company that's trying to get product out the door.  You want me to make time for you, but what have you done for me?  Clearly, you're reading blogs enough to notice when people raise money, but you're not actually reading them for content.  You seem to have missed the new business model: provide as much value as possible and demand less.

    What do I mean by that?  How about, for starters, creating a company blog for your firm.  If you're a recruiting firm, start writing about how to negotiate offers.  Start releasing all the data you can on salaries you're seeing the market.  Weigh in on the "finding developers in NYC" debate.   Talk to us how we talk to our community... in an open and interactive way.  And how about throwing me a freebie?  What's the lifetime value of a recruiting client that runs a successful business?  What's your margins?  I'm surprised that recruiters don't ever offer heavily discounted or free referrals because if they found someone good for me, I'd be convinced of their value and probably use them again and again later on... and probably also make lots of referrals.  Right now, I'm still convinced I can find people on my own, so show me someone I would have never ever found.

     Real estate salespeople?   Tell us what the going rates are.  Tell us the pros and cons of sharing real estate with other companies.  Blog your best deals. 

     Insurance agents?  Well, insurance seems kind of important, but we don't really know.  What do we actually need?  What's a ripoff? You could get a lot of buzz by releasing some really good articles about what things to consider in the lifetime of a startup.

     I have a meeting with a young recruiter next week who's been really persistent and has engaged me in conversation about the market, but after that, I'm not making time for any salespeople who don't provide me and the rest of the community value first.  I want a link to your blog...  not a form letter.  Send me a "Hey check out our firm's article on the current state of the NYC real estate market."  That's all I need.   It's how we communicate with our market and its how you should, too.

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

Top 5 reasons why canned Yahoo! employees should come talk to me

More than 1000 of you got fired today.  You should all come talk to me...   Why?

Well, certainly anyone already in or willing to work in NYC...  because:

  1. I started a group of over 1400 up and coming NYC area tech and digital media folks called nextNY.  We're having our 2 year anniversary party.  Come and mingle, network, drink your sorrows away, etc.  In any case, because of my visibility in the group, people tend to come to be a lot looking for positions to fill, running their startup ideas by me, etc. 
  2. I started a company called Path 101 that helps people figure out what they want to do with their careers.  I've been running mentoring and internship programs for years and always seem to be the unofficial career counselor to everyone around me.  I suppose I can be somewhat thoughtful about career stuff so I'm just happy to chat and help out.
  3. Did I mention that I started a company called Path 101 that helps people figure out what they want to do with their careers.  We just raised some angel money from a top tier group of people and we're looking to hire.  So, if you're a developer, designer, or even someone in business development, come chat.
  4. My blog has 2400+ subscribers... so if I talk to you, we can't use you, and I post your resume, a fair number of people are going to see it.
  5. I'm just a nice, friendly, approachable guy.
My e-mail is charlie (dot) odonnell (at) gmail (dot) com.

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

Getting off Exchange update:GMail IMAP fixed

A couple of months ago, I broke out of using Outlook on my desktop and killed off MS Exchange and I've been loving the results. I use a combo of GMail on the backend, Thunderbird+Lightning+Provider on my desktop, Plaxo (including Win Mobile software) for syncing contacts and GooSync for syncing calendars to my phone. It's all been working pretty well, except that GMail IMAP was losing message bodies left and right on my phone. It was a posted bug and now they seem to have fixed it. So, that leaves the fact that Lightning doesn't do offline calandering as the only buggy part of my experience. I didn't notice it for a while, because I'm pretty rarely offline, but its a real issue. It's also a slight performance issue, as it's always pulling calendars live... should def be caching for that reason if nothing else. If you switch windows, unplug, and then go back to Lightning, your calander will appear empty.

I'm sure that will get done soon enough, but all in all I've been really happy with my experience and have just cancelled my Exchange host.

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

7 Product Features you should add right now

I had a long conversation the other night with an entrepreneur about her product.  While sitting at a bar near the NY Tech Meetup, we brainstormed a slew of new features.

I confessed, though, that none of the ideas I gave her were original. I see as many new ideas and try as many sites as anyone and I'm really good at pattern matching. I can reappropriate useful tools from other sites for relevant situations pretty quickly, making me quite the snappy little regurgitator.

So, if you ever meet with me to talk product, this is what I'm going to suggest you build in: (I think they can almost universally apply to any site.)

1) Rotating cube landing pages - I've written about this before, but Baseball Reference is the most brilliant site on the web, right up there with IMDb.

It's a simple concept:

- Built up a database.

- Structure a limited amout of link dense template pages

- Make it all public.

On BR, you find a baseball player, all the teams he's played on, the rosters for those teams, more players, more stats and teams... player, team, player, year, team, player... click click click... You can go sideways around that site forever. Same with IMDb... movie, actor, movie, director... click click click. So what does your database have? How few templates could you build to expose the whole thing? Sportsvite for example, helps you manage rec sports teams. They have fields, games, teams, players, sports. A public exposure of those templates could get them a lot of traffic, especially with fields. Ever try to Google for directions to a softball field? It's a nightmare. A Sportsvite page with that field, directions, schedule of games, teams that have played there, photos from games, and some hooks to sign up for Sportsvite would quickly rank pretty high. You could then click through to the sports played, the teams, even the localities.


2) The selfish data sucking helper tool
- Hubspot created a brilliant lead gen tool for themselves and others with its Website Grader. You submit your website, it grades you on various SEO stats and requirements, and then gives you the option to save a report by giving your e-mail. Not only is it a pretty useful tool, but its going to be great leadgen for their sales team.

The key here is that if you want data, you need to provide something useful first...and for your first user if you're a social site, it's not going to be intros to relevent other users. That's why del.icio.us and Flickr worked so well. They both worked just fine as tools for yourself, so you didn't mind that you were also contributing tag data. So what kind of stats and info could you give to your first user that gets them to handover valuable data to you?  User #1 has to have something useful to do, and calculation/discovery tools that ask for a user's data are a great way to fill your empty database while still providing value.


3) Kiss the ring management tools for groups - Angelsoft is software that helps angel groups manage their deal flow.  The company could have just as easily published an open website whereby companies post their own financing needs and angels just go searching.  That would have eliminated the need for angel groups, many of which survive through paid membership. 

Why not do that? 

Well, first of all, creating direct to consumer businesses on the web are hard.  It's hard to generate traffic.  Plus, you'd piss off a lot of angel groups who would badmouth you by trying to get in on their gig.  But, if you can build something useful for existing powerholders in your space, people who already have traffic, it may be better off than going out on your own and everyone wins.  The key is if you can piggyback off groups like this and still somehow leverage your own business to be disruptive. 

I'm experiencing that in Path 101,  where rather than compete with career planning offices in colleges, we'll most likely build some tools for them to use to make their lives easier.  This way, they're more likely than not to promote us as well.  Still, I'm not depending on them either.

4) Crawled data - If you can find a way to gather data that's already out there to pre-populate your website, it's a highly cost-efficient way to build your business.  Otherwise, you often wind up building big empty databases. Google does it with local reviews.  I don't think very many people would care to put reviews into a Google database, but there's nothing stopping Google from just crawling reviews it finds on Citysearch and other similar sites 

This way, again, you have something to show user #1, instead of 100% relying on your users to build your business for you

5) Revolving e-mail door for data - Creating user generated content sites depends on the ease of being able to get content into the system.  One of my favorite ways of doing this is to rely on e-mail.  Contrary to narrowminded belief, e-mail is not dead. 

In fact, more and more people are getting smartphones so they can be connected to their e-mail 24/7.  Sites that take advantage of easy ways to add content via e-mail will benefit from this trend. Disqus, for example, now allows me to respond to comments posted on my blog, and post them up on the web, 100% over e-mail.  They've gotten past the need to force everyone to visit their posting page, because they realize that the value is in the data.  The more people comment the more useful the service gets for everyone, so allowing comments to get responded to more easily by just letting me post by e-mail is brilliant. 

6) People like me - People like me can be a simple feature or a hard one... it all depends on how many PhD you want working on it.  I'd be very interested in seeing people like me across many of the sites I visit, and I think last.fm does it best.  (Amazon shows me what people like me bought, but not who those people are.) 

I have friends on last.fm, but I don't get much value out of them because they don't listen to the same music that I do.  However, my "neighbors" are awesome.  It's a totally passive feature and I didn't have to do anything to get a list of people with similar music tastes for me to explore, friend if I want to... that's what social should be about. 

I want that on Twitter.  Do some text analysis.  Who twits about the same stuff that I do?   How about on Newsgator?  Who reads what I do?  Anytime you have a lot of data, you can instantly make a site more social, without all the fuss of "friending" by showing me people like me.

7) Temporary accounts - Path 101 had a great meeting with David from Tumblr about integration.  It was pretty obvious that he's had this in his mind for a while--how can he make his site friendly for partnering?   

People who have intense registration processes often find it difficult to create partnerships.  Who owns this data?  Will you pass it to me?  Is a partner account a real account?  Whose logo will they see?  It's completely stupid because no one really "owns" the user anyway.  You want to own data, not users. 

As long as you get data back, you should do all the white label partnerships you can (unless perhaps you're building a network tool that just would splinter an audience and degrade a product).  In order to do that, you need to develop a way for your system to work without a full registration. 

What's the least amount of data you need to run an account for someone?  Answer: a single unique identifier and a way for a partner to authenticate their sign-in.  That's it... no name, age, birthday, zip, etc...    If you can get those from a partner, great... if not, now you have more users and more behavioral data (plus all the content) and you should be able to monetize that.    

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

Overheard at money:tech

Entrepreneur 2's company got bought by a big Bay Area tech company a few years ago:

Entrepreneur 1: So, how long you in for?
Entrepreneur 2: Two years, two months, three days...
Entrepreneur 1: Ummm... I meant in New York...at the conferece. How long are you here in New York for?
Entrepreneur 2: Oh...leaving Sunday.

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

Two (Hundred) startups enter, one developer leaves? How to decide what startup to work with if you're a highly sought after developer...

If you can code your way out of a hat, you have a job right now.  You're also probably getting lots of offers from completely random startups and people you've never heard of--people just randomly searching LinkedIn for "PHP", "AJAX", or "ninja".

Some are offering just equity.

Some are willing to pay a little.

Some are willing to pay a lot.

Some are offering their sister who is "number four prostitute in all of Kazakhstan".  Very nice!

Clearly, you've got your pick.  So how do you choose?  I mean, you're not an idiot.  You know that the advertising sponsored lolcat CRM Facebook app doesn't have legs, but there are a couple of things that sound like they could work. Still, you're not a marketing expert or finance major, so, even if you just cut the list down to "interesting technical challenges and things I'd like to work on", you've still got a bunch left.  How are you supposed to figure out what might still be around in a year?

I get sent business plans and ideas left and right--sometimes to evaluate because I worked at a venture capital firm, other times because people hope I'll send it on to said venture capital firm.  I also had to to evaluate a lot of companies when I left my last job, before I started Path 101, because I had a lot of great offers.  So, I came up with a short list of criteria for choosing my next company that I think would be helpful to developers who have their choice of startup opportunity.

First, is this a viable concern?  In other words, is this company going to be around in a year?  As cool an idea as something may seem, if there isn't some kind of money coming into this business, how long are they going to stay alive?

"Build and raise money" right?

Raising money isn't easy.  VCs and even angels see thousands of deals a year.  The chances of getting a company funded are very slim, and just because an investor says "they're interested" that doesn't mean anything.  In fact, I'd be willing to make the argument that since it's relatively easy to get a demo product out, that a REALLY interested investor who believes in the team should be willing to fund a company even before the alpha version of the product is out.  It's going to change over time anyway and you need to bet on the team's ability to iterate, so if there isn't SOME money in the company, either from the founders or angels or somebody, I'd steer clear.

What are they willing to give you?  One of my BIGGEST pet peeves are businesspeople who overestimate their value to a company.  Look, I had the idea for Path 101.  We raised 350k basically based off my relationships.  I'm the one with the experience in our niche.  And what are we worth without Alex, the CTO?

Jack Squat. 

That's why we're equal partners.  So if you've got a team of four businesspeople who are hogging up all the equity and they want to give you only a crumb, steer clear.  You're building the site...  creating the experience.  Where would they be without you?

ON THE OTHER HAND, don't underestimate the value of relevant experience either.  I see a lot of two developer teams that have zero industry experience whatsoever.  That's great if you want to flip to a big competitor for beer money, but if you want to be a part of a company that makes a huge dent in a market and changes the way people conduct business, then you need someone with experience and connections to make it happen.  How are you getting into your best business development relationships?  LinkedIn or are you actually getting real recommendations from people who know the team well?  It's too easy to just build something and think you have a business.  A business fits in within an industry--it isn't just technology.  It creates value for stakeholders--enough value for the right stakeholders.  Take the music industry.  Just because you can do something nifty with MP3 playlists doesn't necessarily mean you have a viable business, especially since big lables can be a minefield.  Step too far to the left and, as John Madden says, "Boom!"

Is the market big enough?  Do you have to bet on lots of people doing things they've never done before for this to be successful?  Do you know anyone without a computer science degree that would even understand this thing?  Go ask 10 of your non-tech friends and see what they think of it.

And finally... how dedicated is the team to this idea?   Do they live it?  Is this just a neat idea they came up with while they were bored one day or has everything they've done in their career and their life led up to this moment of creating a business?  Do they embody this business?  This might sound like overkill and a little hokey, but trust me, when you're still months away from a big turning point, and you're out of money, and its going to take some sleeping on couches and dipping into 401k plans to keeps something alive, you better hope that the founding team thinks its more than just a good idea...

....it better be THE idea.

Any other tests for programmers to find the right startup?

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

Twitter needs to level with us and open up about their problems

@jack, @biz I'm not going anywhere... at least not for a long time.  So, don't consider this a threat to go over to Pownce or anything. 

In fact, anyone who threatens to move isn't really thinking properly, because if we all moved to a different service at once, I'm sure we'd experience the same issues. 

But, posting blog posts titled "Happy Happy Joyant" when you've had so many outages lately and your user base has little confidence that you're going to scale for the Superbowl and no confidence that you'll make it through SXSW without a hitch...  its just not the right sentiment.

You guys built a fantastic service and we all love it, but we've all seen how scale problems can take down a business.  (Friendster) And while the service is popular, it's not THAT popular.  Most of your userbase is still pretty technical and it wouldn't really take much more of this before people started leaving en masse.  It's exactly because they're pretty tech savvy that you have a unique opportunity to open up a discussion about your recent problems and engage your userbase.

Let's start a discussion about whether Ruby scales or how you diligence a host.  Is it a matter of just throwing more hardware at the problem or are database and architecture redesigns in order.  If I were Lee Mighdoll, I'd make it a point to blog almost everyday, even a short one, about the problems I'm facing and steps I'm taking to address the issues, so at least people feel like something's getting done.

Take a cue from Six Apart, who experienced serious uptime issues in the past and seems to have gotten over them.  If nothing else, their tone during and immediately after their problems was the right way to go.

"We are truly sorry for the frustration and inconvenience that you’ve experienced, and will provide as much additional information as possible as soon as we have it."

The Twitter blog hardly ever provides any information and there's yet to be a discussion of what the scaling issues are or timely accoutns of them.

Here's another post where they Six Apart recapped exactly what happened with one of their outages:


"Before we get into the details, we want to reiterate just how sorry we are for the inconvenience this has caused. We know our customers rely on us to provide superior service and performance, and that on Friday we let you down. The fact that Friday's outage came on the heels of our performance issues in October is obviously frustrating, both for you and for us."

Then they go into a pretty lengthy blow by blow account of what was going on.  People want to know that because they want to feel like something's being done. 

You guys should know that from dealing with your cable or phone companies as a regular consumer.  Waiting in silence for somebody to fix something sucks.  And it sucks even more when the service doesn't level with you about the fact that their are issues. 

"Happy Happy Joyant" just feels like mocking, to be honest, and doesn't inspire a lot of confidence. 

Here's your opportunity to be an "us" company or a "them" company with regards to this issue.  It's a critical point in the life of your young company. 

I'm rooting for you guys to approach it the right way.    

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

Etsy Raises $27 mil... Accel and Jim Breyer comes in. Score one for NYC

Nice work folks.  I like the fact that this can only serve to make Rob Kalin more confident, because sometimes, I think that can be an issue with him.   :)

And if you believe that, I have a bridge to sell you.

Seriously, though, put $27mil. on the venture funding in Brooklyn toteboard.  No sleep 'til...   

Congrats!

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