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

Can there ever be a successful calendaring startup?

So Kiko got sold off, and Skobee slips silently beneath the sea DiCaprio style...   but we still hold out hope in the face of tractionless attempts at fixing what we perceive to be a real problem.   Calendaring and invitations, obviously going hand in hand, seem to work far from efficiently GigaLiz puts it perfectly...

"Every time we have to click through an Evite, we cringe. We can’t say we use Skobee, Renkoo, or even aggregator sites like EVDB’s Eventful, Zvents, and Upcoming on a regular basis — that would require a mass migration by the people we do stuff with. But we do hope that someone makes it easier and more efficient to make social plans online."

Web 2.0 purists feel like Evite sucks, but you know what...  most mainstream tech users I know  have one of two opinions of Evite...   

It does the job...

... or they just don't like public RSVPs. 

I've never heard anyone on my softball team tell me that its unfortunate that Evite doesn't have more functionality.  In fact, the only thing I use that seems to work even better than Evite is a numbered list on the nextNY wiki...  which has even less functionality.   

The problem isn't client side...  in the invitation interaction itself, its server side and its on multiple levels.  Google Calendar didn't kill Kiko.  I don't know anyone that actively uses it.  In fact, I hardly know anyone who uses any calendar other than one their job forced them to... and less than half of the Outlook users I know put personal items on their work calendar.

Here are the nearly insurmountable hurdles anyone in this space needs to get over:

1)  Most importantly, most people just don't want a calendar.  It makes them feel too structured, under pressure, etc.  All these attempts in the "scheduling" space come from people like me who live by their calendar and whose life would be so much easier if everyone else did, too.  We keep thinking that, if there was only a good enough tool out there, we could get everyone using a calander, and that's just unrealistic.

2) Events drive calendar use, and only a minority of events are formatted to work with a calendar.  Think of the average family...  the biggest drivers of the family schedule--the kids' school and after school activities--are not in iCal, hCal, vCal, or any kind of call.  They're on a paper flyer or on a printed e-mail on the fridge.... or maybe written onto the fridge calendar.  Until schools get into Microformats, don't expect mainstream users to either.

3) You never know if the person you're inviting uses a calendar.  The beauty of Evite is that even if the other people never check the Evite again, it works for you when they click yes.  Try doing that to 100 people with an Outlook invite.  Half of the e-mail programs that open the message won't know what to do with it.  It was like when text messaging first took off here.  You didn't just randomly text everyone...  b/c you didn't know if they could get texts.  It took a critical mass of texting enabled phones for people to really get into texting here in the US, and reaching that critical mass took a long time. 

4) People don't want to let you know what they're doing.  What would really drive a lot of calendar usage is if you could negotiate for people's time based on levels of trust, open times in their calendar, etc.  For example, when I schedule a game of pool with my friend Brian, he's pretty much always going to accept an invite as long as he's free.  I should be "ok'd" to book a certain amount of pool in the empty spots in his schedule.  But, how can he expose his schedule to me w/o exposing it to the world, but also not come off like a complete loser if he doesn't happen to have anything booked yet for his Saturday night?   People share bits...  music, videos.. they don't like sharing information about how they spend their time...  b/c it makes them feel committed, locked in.

In the face of this behavior, what kind of scheduling service could ever be successful?

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

The Lost Art of Answering the Phone

So, Adi Sideman, the CEO of Oddcast, just came into the office as he usually does late Sunday mornings and something he did just reminded me something interesting about the culture here.

He picked up the phone.

Not his phone number... the main line.

"Good morning, Oddcast".

We often talk about the "no touch" style of Google AdSense and other self-serve applications, but something I noticed from the first day I walked into Oddcast always strikes me.  Our phone number is on the website, and people here always pickup that main line.  If the CFO is at my desk and she hears the main line go off, she grabs the nearest phone possible to answer.

Its usually someone who needs a password reset or something silly, particularly if its on the weekend... and I'll bet few of the people who call release they're getting the CEO of the CFO of the company.

A personal touch is something that's really important to the people here and its sort of refreshing.  Admittedly, I don't rush to grab that line if I'm here by myself, but maybe I'll start.

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It's My Life Charlie O'Donnell It's My Life Charlie O'Donnell

My Work Style

In the last... hmm...   ten years, my work environments have never been stable and its been difficult to optimize for best results, but I've learned a little something along the way.

In high school, I used to hole up in my room after coming home from play practice (little known fact in the blog world, I did four musicals in high school...).   Doing work in your bedroom is probably the most distracting thing you'll ever do.  I was unlucky enough to have my own phone line, too (well, the other extension on that line was my dad's fax machine), so that didn't help.   Still, I only had a few hours a night to work and so time pressure helped.  I work much better under time pressure.

Also in high school, I took an architecture course.  Anyone who is building anything, be it a still life water color or a web serivce, will tell you that doing creative work is the most time consuming thing you'll ever do--because you can always put more time into it.  I spent every single moment of free time I had (and in senior year of high school, that was a lot) in the art room.  I had picked out the best drafting table.  It was tucked away in a corner behind a dividing wall and I had my back against very high windows... great light.  Most of the time, the room wasn't being used, so I had dead silence.   I got a lot done.

In freshmen year of college, I have to be honest...  after coming out of Regis, the work seemed sort of easy, so I didn't have a lot of time pressure.  I mean, I had class three times a day, no commute...  gobs of free time.  Again, I went with an enclosed space.  In my room, I built a "cubby".  I took the bookshelf from my the back of my desk and attached it to the end of my bed over in the corner of the room.  The cubby was great... I could go in there and people wouldn't even know I was in the room even if the door was open.  I miss the cubby.  I need some walls.

Sophomore year, I was in a huge room, but with three other guys.  The TV was always on, so doing any work whatsoever in my room was just a no go.  So, everyday in the first semester, I spent some amount of time at a cubby-like library desk with my laptop.  (That was 1998... first time I ever had broadband.)   I also used to go into the lounges in the dorm to work at random hours.   That was when I really started to learn how to wake up early.  I would wake up at 6AM and get two solid hours of work done before most people on campus even woke up.  That's one thing about the way I work...    I don't fare well on a normal daytime work hour schedule.  My best times are 6AM-9AM and 3PM to 8PM.   If I could basically work those hours, I'd be very happy.  All this forced quiet time let to my only 4.0 semester...  that was an abberation, but it was fun while it lasted.

Junior year was a disaster, relatively speaking.  I was an RA (stupidest thing I ever did) and so I had my own room.  I should have learned from high school that I can't work productively in my own room.   Lots of wasted effort there.... too many distractions.  I should have went to the library.

Senior year, I had mostly finance classes, so the amount of work I actually needed to do, after interning for a corporate pension fund for four years, was pretty minimal.

When I was at GM, I learned about my afternoon boost.  At about 3PM, I used to kick myself for not being as productive as I could be...  partly b/c of my own lack of concentration and partly because of all the co-worker interruptions I'd get in a day.   So I started pounding stuff out like a mad man for four hours or so and would leave at 7 or 8.  Funny how I can't get my mind to work exactly when I want it to.   

At USV, the work was really just so different.   When you're networking, researching, trying things out, its hard to figure out exactly where your work ends and just your overall interest in the area begins.  So, I'd sort of work a little bit 18 hours a day...  continuous partial attention.  If I was IMing some guy who worked at another venture firm about what verticals could benefit from aggregation, was that productive work?  I think so, but it sure felt different from writing 12 page papers in high school.  I don't remember networking much in high school.

So, here at Oddcast, I've been here a little over a month...    I'm a couple of weeks away from finishing all the design work that will go into our consumer product, and I'll tell you, its been like herding cats to get my brain working correctly.  Like, this morning, I woke up at 6AM, drove into the office to get work done, and was going very well for a few hours before this blog post.  Now, why I couldn't manage that on Friday morning, I have no idea.   I was going to go kayaking, but its raining again, so hopefully, I can get another spurt like that.   

One thing that is very helpful.... unplug once in a while.  Turn off your IM and e-mail while you're working.  I'm going to do that right after I click publish...

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

Searchnology.com Reveals New Site Search Technology

Here's a thought...   to what extent should you count on a GP to catch organizational issues and involve themselves in the day to day issues of a business?  Is this different in a venture company vs. a buyout?  Is failure to execute a problem of management or a problem of oversight of management?  When things go wrong at a company, how does a GP know before its too late?

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Charlie O'Donnell Charlie O'Donnell

Dreary day


Dreary day, originally uploaded by ceonyc.

Eh...looks like its going to rain... I'm going to get out of here soon.

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

Is MySpace a fad?

Darren asks this question in response to the recent article in Wired.

He says it compares very closely to the hot, then not, NY club scene, but I think there's a big difference.  Clubs have a pervasive atmosphere to them... a culture.  Certain clubs appeal to certain types of people at certain times.  They trend younger, older, hipster or homeboy, and among these groups you want to have the best of the bunch there.  When younger people "invade" a more mature club, or older, less cool, people invade hotspots for young people, the strength of the club's identity and therefore the brand declines.

MySpace, however, isn't the same club to everyone.  Its flexibility allows groups to form on their own.  Its what danah refers to as "glocalization"...   bringing together your world, not the whole world.  I can discover other Mets fans, other Lacuna Coil fans, people in Bay Ridge, or other Italians.   No club can do that in real life, and so the idea that "whatever you want" might go out of style is something I disagree with.

However, that doesn't mean that MySpace can't fail.  The site is very slow and buggy and has serious scaling issues, like Friendster before it.  It is full of a lot of spam, and as a development platform, its like the Wild West.   Plus, its still pretty closed.  Are these fixable problems?  Definitely.   

Here's what I'd love to see MySpace do to secure its future at the top and avoid some social network pitfalls:

  1. Fix the spam problem or at least open up and let someone else fix it.  I'd sign up for any service that blocked any new female with only one picture and no profile bling and mostly male friends to invite me or message me.  Its a very easy algorithm to detect fake profiles.
  2. Innovate around your core strength: Upgrade music.  Music is the backbone of the network and the functionality of the player hasn't changed at all.  I'd love to see a MySpace/Pandora or MySpace/Last.fm integration.... anything that enables more radio station like functionality.  Discovering songs one click at a time is not as fun as being able to let it play for an hour or two.  Plus, why can't I break the player off the page and play it on my blog?
  3. Scaling issues.  Hopefully, Google will lend MySpace a few PhDs to help the "MySpace Technical Group" which gets a bug report every ten seconds I use the site when a page doesn't load right away.  No reason why they can't get enough servers and bandwidth and fix the code to make the site run smoothly.  I mean, the "check my address book for contacts" thing has never worked! 
  4. MySpace Developers Network or Whitelist:  If they keep approching widgets with this cat and mouse game, we'll never see integration with other services reach its fullest potential.  Innovation is what will keep people on the site, and creating a healthy platform for trusted developers to work with will benefit everyone.
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Random Stuff Charlie O'Donnell Random Stuff Charlie O'Donnell

Small is the new big? Tell that to Pluto

And then there were eight

Everything I learned in elementary school science seems to be a lie.   

Did you know there were more than three states of matter?   At first I learned about Plasma, making it four, but now it turns out there are a whole bunch of 'em.  That probably explains why if you leave ice cubes in the freezer long enough, they completely disappear.

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Friends and Outings Charlie O'Donnell Friends and Outings Charlie O'Donnell

New Blog: Blogger working with special needs individuals

My friend Vanessa just started blogging to help facilitate conversations with other people working with people with special needs.  This field is really important to her... as her dad was diagnosed with MS over 25 years ago.   If anyone has any tips for other bloggers in this field she should connect with or how to approach this kind of a blog, please leave a comment on her site.   Good luck, Vanessa!  Its obviously a very worthwhile endeavor.

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MeVertising Charlie O'Donnell MeVertising Charlie O'Donnell

My nana doesn't subscribe to RSS, but she's not exactly an "influencer"

AdAge left out a key criteria in their overview of mainstream vs. cutting edge advertising...

"While marketing prognosticators and technophiles rush into the future, raving about the next big content delivery system or ad model, the fact is most Americans -- notably adults with steady incomes -- still get their content the old-fashioned way."

I agree, but how many of the key influencers are still doing this, but the bleeding edgers, trendwatchers, trendsetters, etc. habits are changing...  you can't argue that.  You don't have to reach everyone on the first try.. .you have to reach the right people... the people that other people want to be like.  These are the people that are always trying stuff first and get social capital for that.  There was a time horse and buggy sales were still strong, too, you know.  If you're not adopting to new technologies, you're going to find yourself far behind very soon.

I mean, seriously, who would you rather market to, my 88 year old Nana, or her 27 year old RSS enabled grandson who she knows is cool and wants to be associated with.  :)

SANY0046

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Kayaking Charlie O'Donnell Kayaking Charlie O'Donnell

More lost electronics... Camera in the Hudson

Last year, I broke two Treo 650's, and got my camera stolen.  Today, I sunk to a level of idiocy I am capable of, thankfully, ever so rarely.  We opened up at Pier 40 today and it got pretty choppy in the afternoon.  I had my Fisher C-1 in my pocket and decided to go out for a paddle.  I was on a high sit on top boat that kept me pretty dry.  However, I decided it would be a good idea to try and actually land the boat on the dock by catching a wave. 

Not smart.

I got about 3 feet up on the dock and just hung there for a moment before it capsized.  I immediately realized my camera was in the water and pulled it up and out as soon as I could, ignoring the boat, which got swept under Pier 40.  The camera was fried and the boat lost in the depths beneath the pier.  Not all was lost though.  I was able to scoot underneath the pier and retrieve the boat with a tow rope.

Also, more importantly to me, the Flash card was ok, too, so I didn't lose the pics I had taken.

SANY0059 SANY0050 SANY0054

So, anyone have any suggestions as to what camera I should buy?   I guess I want 6+ MP, small, very good video and I'm somewhat price sensitive.  If anyone has links to pics they took with a specific camera, and videos, please post them and the name of the camera.  Thanks!

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It's My Life Charlie O'Donnell It's My Life Charlie O'Donnell

Wholesale Inflation Barely Rises in July

So DTUT has become a “they” company.   

They’ve killed the wireless internet after 7PM.  I asked the guy behind the counter what the reason was, and he said that it “ruined business”, because the laptop freeloaders would order the minimum amount or nothing at all.  I looked around.   I’ve never seen the place so empty on a Friday night.  I wanted to just reach across the counter and explain to him all about incremental profits and overhead, but, I realized that it would probably be to no avail.  Counter Guy doesn’t care.  Now, perhaps it’s true that the people using the wifi do order less, but the point is, they order something, and, there is incrementally no cost to keeping the wifi on all the time.  The only legitimate financial argument you could make is that, somehow, the overabundance of laptop freeloaders drives away higher paying customers—that the place is already at capacity and it ruins the mix.  Of course, that’s not the case.  People rarely walk out of the place because it’s too crowded.  I mean, sometimes its packed, but like right now, its pretty empty.  (I’m typing this on Word because I already bought my green tea without realizing the wifi deal.)  Do I usually only order a green tea while I’m here?  Sure.  But…  so what?  What’s the margin on a $2.25 green tea?  90%?   In other words, at eight visits a month, I pay for half the wifi myself.  Do I take up the space of an otherwise higher paying customer?  No, definitely not.  In fact, the wifi is really the only reason why I come here in the first place.   And, in fact, one thing they fail to take into consideration is that because I’m here all the time freeloading off the wifi, it becomes my central hangout place and I’m used to coming here.  So, when I’m looking for a place to go to with friends, this is also my number one stop.  Now, however, I’m annoyed, and their ridiculous retraction of the free wifi has created ill will.  I’m less likely to come here the next time.  In fact, I’m less likely to come here at all.  I have a feeling this won’t last.  Although, perhaps it will, because the downtown location of DTUT just closed, so perhaps they’ll run this place into the ground before they have a chance to change the policy.

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It's My Life Charlie O'Donnell It's My Life Charlie O'Donnell

Good Play Not Enough For Mercury

This afternoon, I finally closed on my new co-op apartment...  and only nine days after I moved out of my old apartment.  :\ 

Thanks to Joy for letting me crash in her empty pad while she was away.

Apartment and neighborhood tour to come soon, but for now, I'm just glad to be in my own place.  So, over the next few weeks, I'll be getting another couch, a bedroom set, and some office furniture.  I may sit in reception at work, but in my own place, I have an office!!  Woooo.  I'll be painting, too.  I'd say it will be ready for a housewarming party by the end of the month. 

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Kayaking Charlie O'Donnell Kayaking Charlie O'Donnell

The Downtown Boathouse Returns to Downtown....sort of

When we moved from Pier 26 due to the renovation (total destruction) project that leveled the Downtown Boathouse, we moved most of our stuff up to the shiny new boathouse at Pier 96 at 56th Street.  We didn't move everything there, though, and we still wanted to maintain a downtown presence if we could.  So, we rented some space at the south end of Pier 40 (at Houston St.), but it took almost all summer to get the right permits to put a dock in.

Finally, this Saturday morning, the Downtown Boathouse will open up the Pier 40 location and make its triumphant, if not a little disorganized, return to downtown.  You have to walk down the pier a little ways on the south side to see us.  We don't have as many boats there as we used to at Pier 26, and all of our trips will still run out of Pier 96.  But if you're used to dropping by on us at Pier 26 because it was close by, come see us on Saturday to see what we're up to.  Even better, come help out!  I'll be there from 9-5:30, but the closer you come to either end, the more you risk that we'll either be just getting organized or closing early because no one showed.  :(     Hope to see you there!

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