Elevator pitches, weddings and babies

At OpenPlans, we’re busy signing up new clients for our products & services, and we’re also spending a lot of time fundraising (from individual donors, foundations, etc.).  As such, I’ve been thinking about how we pitch our organization, and have recently spent some time over the past few days reading some of the great stuff over at VentureHacks. Their book, Pitching Hacks covers the fundamentals, from what matter to investors (traction), to how to get introductions, to how to structure your pitches (whether high-concept, elevator, or slide deck).

Then, this morning while reading Hacker News (or more specifically Nirmal J. Patel’s full-content RSS of Hacker News), I came across this posting which caught my eye:

Technical co-founder wanted for disrupting the wedding industry.

Hi, my name is Tracy. The wedding industry is huge, overpriced, and with insane profit margins. I’m looking to disrupt it with WeddingType.

In wedding invitations alone, there are two options: spend hundreds of dollars for custom designed invitations (expensive but pretty), or do-it-yourself (cheap but ugly). I want to build a web application catering to the price sensitive couples who have an aversion to Comic Sans.

A do-it-yourself wedding invitation kit costs $45, while professional wedding invitations are hundreds or thousands of dollars. With WeddingType, the service will guide the user through a constrained flow of inputs which will populate a set of pre-designed templates with professional typography that they can print out and get hitched. The completely automated service will charge $25 and send the user a PDF by email.

My goal is to get this out really fast and start making revenue from the start, then see how big we can grow it. From here, there are multiple ways of increasing value and revenue — licensing to wedding invitation template manufacturers, selling custom design solutions, offering templates through the site, etc. Large scale, could sell templates through the site, printing and mailing like Moo.com.

I freelanced and worked at a startup for five years as the primary designer/jack-of-all-trades for everything relating to their web properties, including analytics, usability, design, HTML/CSS, and multivariate/AB testing. I need a technical partner who is enthusiastic about the business and a web programming whiz. Preferably in the Bay Area, and if everything goes right, we’ll apply to Y Combinator for the next Winter session.

Intrigued? I’d love to meet you, perhaps work on a small project together.

This is not a perfect pitch, by my or VentureHacks’ standards — in fact, I am not fully convinced by it after the first paragraph. However, I think the title and first line are good, and they are what drew me in.

Speaking from recent experience of getting married (in 2005) and having a baby (last year), I can say with absolute certainty that these are both huge markets where there’s an opportunity to be smart and offer products that will serve people well, save them money, and be profitable.  In this pitch, it was the problem/opportunity statement (“The wedding industry is huge, overpriced, and with insane profit margins”) that got me.  I certainly agree with that part.  Wedding invitations are one piece, and there are many others.  My wife has a million ideas for businesses in this space.  If I were an investor in XX Combinator, I’d definitely start here.

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Jul 28, 2010

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Markets, Pitching

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Missed Connections

In her bathroom, a friend of mine has some really beautiful illustrations of posts from the Craigslist Missed Connections section.  If you’ve never looked at missed connections, you should — there are some really wonderful notes in there (also some sketchy ones).  Here’s a beautiful one from today:

7 train glances on monday – w4m – 20 (7 train Queensbound)

We were sitting opposite each other on the train. We caught eyes early in the ride, but you nodded off through most of it, but looked up as I was getting off. As the train moved you kept looking at me walking to the stairs.

All I want to tell you is that you have the most beautiful clear blue grey eyes.

What’s striking is how many of the missed connections take place in the subway.  I’ve said before that transit is a uniter not a divider; these posts confirm that, and are a really nice view into that slice of NYC life.

The “ad hoc groupings” that take place on the subway also really resonate with the ideas in Dave Weinberger’s Small Pieces Loosely Joined, which I’m reading right now.  Dave talks about how on the web, groups take on a new meaning — they form and unform quickly, and can be formed by very loose connections (such as commenters on a blog post).  The city is the same way — the people I’m standing with on the subway are an ad-hoc group that unforms just as fast as it forms.  But there’s definitely a connection. Typically, it takes an event of some kind, like a man talking into a banana phone or two people having a loud argument, to draw more outward communications among riders.  But underneath it all, there’s a hidden set of communications going on, and it’s really beautiful to see it unearthed through Missed Connections.

It turns out the posters are by a Brooklyn-based artist named Sophie Blackall, who has a whole poster series + a blog on Missed Connections.  Really nice.

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Jul 21, 2010

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Art, transit

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Wanted: Aggregated Group Playlist

I love music, but I am really bad about keeping up with new stuff.  My iTunes library is only so-so, so I spend most of my time listening to playlists on 8tracks.  This is good for variety, and great for finding the right background music for a BBQ or party, but there’s something missing: my friends.

I have a few friends who have great taste in music, and who are totally on top of what’s new and good.  As it works now, every once in a while I’ll get a recommendation from one of them, I’ll buy the album on Amazon, and then I’ll listen to it non-stop for a few weeks.  It’s great when it happens, but it doesn’t happen that often.  I want something more automated and frequent.

A few of these friends publish their music on the web (see Piecemaker and My Brooklyn is Better).  Problem is, they each use different platforms to publish, and as far as I can tell, there’s not a great way to combine these into one stream.  Piecemaker uses WordPress and outputs a standard podcast feed, and My Brooklyn is Better uses Tumblr, which embeds a flash player and forbids linking directly to the audio file.  I’m sure I have other friends who are publishing on platforms (Last.fm, 8tracks, Facebook?) that I don’t know about yet).

So, what I want is a way to take these streams, regardless of platform or format, and create a mixed feed or webpage.  I don’t care about actually downloading the music; I just want to be able to listen on the web, keep track of the ones I like, and have the option to buy the albums later.

I’m sure this is possible using some combination of tools that are already out there.  For starters, I’m playing around with Yahoo Pipes to see if I can mash something up to my liking, with an eye towards playing it on the web using StreamPad.  We’ll see if that works.  But is there something out there that I’m missing that already does this in a more straightforward way?  Seems like there must be, but I haven’t found it yet.

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Jul 17, 2010

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LifeHacking, Music

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Unplugging (sort of)

This week, we’re on vacation in Cape Cod with my wife’s family.  They’ve been renting the same tiny cabin by the beach for the past 35 years, and coming here is pretty much the highlight of our summer each year.  Last summer, we brought Theo here when he was just three weeks old.  This morning, he and I took a walk along the harbor in Provincetown at low tide — he thinks of each beached boat as a giant bucket, just waiting to be filled with sand.

The problem is, whenever we’re on vacation, I have a hard time finding the right balance between “unplugging” and staying engaged with the real world.  One the one hand, I want to remain connected with work and friends, on the other, I just want to tune out, relax, and be with the people I’m with.  Inevitably, I end up fighting the struggle each day, carving out some time for the important stuff at work, and forcing myself (with limited success) not to stress about it too much the rest of the time.  It’s tough, and to some extent I feel like I achieve the worst of both worlds: neither able to fully enjoy my break, nor be fully present for important happenings at the office.

This has become more of an issue as technology has evolved.  Here at the cabin there’s never been any phone or TV.  Then there were cell phones.  Next, internet down the road at the town library. Then, iPhone and blackberries.  Now, this year we have a mobile broadband connection for our laptops, so we’re as connected as we can be.  For certain things, it’s great: we watched the World Cup final online last weekend, and yesterday my father-in-law did an interview via Skype, which saved him a day-long trip up to Maine.  But, work email and things to do are now within arms reach at all times.

I suppose the vacation case is just a microcosm of the larger question of how to balance real-world face time with online time.  Fred Wilson, one of my favorite bloggers, covers this topic frequently, and I’m really amazed the extent to which he’s able to stay engaged with the networked world without driving his family crazy.  In our case, the family is only semi-digitally integrated; it’s just not part of our culture to always be connected.  Maybe getting an iPad would push that culture change in a good way.

Lastly, I think it also comes back to information fitness — using online (all?) time to do the most important and productive things, and not just consume endlessly as you might in a less online constrained environment.  And of course, one of these days I’ll be able to plan ahead enough so that everything is under control at the office and I don’t have to worry about anything.  But I’m sure if I did that, I’d find reasons to plug back in…

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Jul 14, 2010

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Constraints, LifeHacking

The optimism of the traveler

This morning, I drove from Boston to Cape Cod, alone with my thoughts except for Theo sleeping in the back seat.  Once we were out of the city and smoothly on the highway, I got to thinking about work, and things really started clicking.  I found myself reaching for my iPhone to record voice memos about once every minute.  I may have even cracked an important nut; we’ll see.

I can’t remember where, but I once heard the phrase the optimism of the traveler, and the idea has really stuck with me.  For me, this manifests itself in the fit of ideastorming I usually find myself in whenever I’m on a plane or train (and sometimes when I’m in a car).  Some of my most creative and productive times have been in these situations.  And it’s not just about volume of ideas — there’s a different sort of excitement and hopefulness that happens during these times.

So, what is it about traveling that produces such excitement?

Is it being away from the internet, and therefore being forced to digest some ideas and not just consume at will?  Or maybe it’s less about attention, and more about being in that middle place between destinations, where anything is possible? Whatever it is, it’s really great.  Of course, the hard part is putting those ideas into motion once you’re feet are back on the ground…

// Photo by Tjeerd on Flickr

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Jul 11, 2010

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Vision

Fitness

I’ve been thinking a lot about fitness lately, mostly spurred on by the great stuff coming out of Clay Johnson’s new blog, InfoVegan. Clay has been drawing a parallel between physical obesity and information obesity, and has been diving deep on what it means to have a “healthy information diet.”  It’s inspiring stuff, and definitely worth keeping up on.

The takeaway for me is that fitness (of any type) is largely about producing, not just consuming.  You need to write to properly digest what you’ve read, and you need to exercise to properly digest what you’ve eaten.  My favorite characterization of this is David Eaves’ “if writing is a muscle, this is my gym” tagline on his blog.

So in the spirit of fitness, yesterday I went for a run and today I wrote this post :)

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Jul 9, 2010

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LifeHacking

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LifePruning

I spend a fair amount of time thinking about LifeHacking.  Getting my inbox filters just right so I can get to “inbox double-zero,” syncing my iPhone and my Google Calendar, setting up ssh keys in all the right places, etc.

But something I’m still not that good at is “LifePruning,” that is, the continual process of getting rid of all the old / no longer relevant shit in my life, the stuff that, if left untended, will crowd out all the good stuff.  It’s kind of hard for me, as I have natural hoarding tendencies, but I’m trying to live by a new code: prune first, ask questions later.

This weekend, with an impending move from NYC -> Boston, I’ve been doing some pruning, and boy does it feel good.  Huge bang for the buck.  I’m going to try and make this more of a regular routine.

Here’s the quick rundown of the LifePruning I’ve done, this week alone:

  • Cleaned out my clothes closet and donated all the things I never wear anymore / don’t fit.  Amazingly, getting rid of those uncovered some real gems that I had forgotten about.
  • Got a new computer and transferred my data and applications.  Not all of them, mind you; just the ones I really need.  The result is a leaner, meaner, faster machine.  (Note: getting a new computer is not required to do this, but it helps)
  • Went through my Google Reader and deleted all the feeds I no longer read, or are just less into these days.  That means less distraction from the awesome ones I want to make sure I actually read every day.

I know that good things will come of this pruning, and I’ll try and keep track as they do.  For example, I’m sure I’ll read a great post I would have otherwise missed thanks to my RSS pruning, and I’ll look sweet at the office in that shirt I found in my closet (not sure of the practical usefulness of that), and so on.

This is just a start.  I’m going to keep an eye out for more LifePruning opportunities, and I’ll post them here as I do.  If you have a good life pruning suggestion, let me know.

Update: SVN has a post today on this topic: The Art of Taking Things Away.

// Pruning grahpic via Agriculture Guide

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May 15, 2010

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LifeHacking, LifePruning

Talking transit tech @ the MTAdev conf

Next Wednesday, I’ll be on a panel at the MTA Developers Unconference.  I’m very much looking forward to the event, because among other things, one of my fellow panelists will be the new MTA Chief, Jay Walder.  Here, I’ll give an overview of what I’m hoping to discuss on the panel; any feedback would  be greatly appreciated.

Before I get to that, though, I should note that it’s been an interesting journey working with MTA on its open data and developer relations policies over the past year.  In a nutshell, it’s gone from a highly contentious situation, to an atmosphere of open collaboration.

Almost exactly one year ago, here at OpenPlans we were beginning to experiment with the problem of tracking buses through the city.  That led us to dip our toes in the world of transit data — since you need to know the routes and schedules to do tracking and predicting — and introduced us to some of the challenges in getting accurate and up-to-date NYC bus schedule data.  Over the next 9 months, we engaged with the NYC transit developer community and the MTA to help work through the issues standing in the way of open MTA data.  We were very pleased when they announced in January that they’d be launching a developer outreach and open data program.

We believe that most of the credit for making this dramatic change happen goes to Chairman Walder and his conviction that open data would lead to innovation and ultimately better service for riders.  In his words at the time of the MTA dev center launch: “We need to get out of our own way and instead get out in front of the data sharing revolution” (via Second Avenue Sagas).

But I’d also like to personally thank Nick Bergson-Shilcock, David Turner, and the rest of the transit team here at OpenPlans for their hard and important work in helping to organize the NYC transit developer community, and in helping to identify and work through the sticking points regarding open data policy with the MTA.  Back in August 2009, I got an email from Nick to the effect of “This is going to be really big, and we need to step up and get involved.”  That prompted us to start the NY Transit Data Meetup, and develop a more serious and structured conversation about open data with the MTA and the developer community.  Thanks Nick; you were right (as usual), and I’m really happy that I listened to you (as usual).

Fast forward to today.  MTA has open data, a growing developer community, and is iterating.  From our perspective, they seem to be heading in the right direction.  So, that begs the question, what should they focus on next?  Here are a few things that I’ll be interested in hearing about & talking about on Wednesday:

  • Within MTA, which datasets would be the next easiest to expose? Of those, which would be the most interesting to developers?
  • What can we do to increase data sharing among other regional transit agencies? Last I checked, NJ Transit was the largest agency without open data according to City-Go-Round.
  • Let’s think beyond just transit data to transportation data. When it comes to planning trips, modes should be abstracted out of search.  What other datasets (outside of the ones in the MTA’s control) would be required to make some really interesting things possible?  (I’m thinking DOT for traffic, TLC for taxi data, paratransit, etc.)
  • Real-time. MTA has been piloting real-time bus location data on 34th street.  Would love to see the L train and 6 train in future pilots.
  • (Imaginary readers out there…) If you could ask Chairman Walder one question, what would it be?

That’s it.  Have a great weekend, and here’s to smart transportation and open, interoperable cities…

// Heart shaped subway map by ZEROPERZERO

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Apr 30, 2010

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Cities, transit

Introducing OpenPlans, and the evolution of a brand

After many moons of plotting and scheming, yesterday we announced our organizational rebranding: The organization formerly known as The Open Planning Project (or TOPP) is now OpenPlans.  I am excited, and I think this is a welcome development.

For years, there has been mass confusion (chaos! pandemonium!) around our name.  Our emails were @openplans.org, our website was topp.openplans.org (until 2009), and our name was the Open Planning Project.  To top it off, for several years, we ran a separate web service called OpenPlans (now under new management as CoActivate).  As I’ve mentioned before, I’ve never been comfortable with these conflicting brands and identities, and I’m psyched that we’ve finally made the leap.

Here’s a quick look into where we ended up, and how we got there.

First, we’ve updated our logo.  Designed by the spectacularly fabulous Andy Cochran, it’s similar to our old logo, but with cleaner lines and more meaning.  It probably goes without saying, but we’ve got the “O” and the “P” in there, and the shape is a broken circle, evoking open processes:

For comparison, here’s the logo that we’d been using for the past year or so.  In order to minimize confusion between OpenPlans (the service) and The Open Planning Project the organization, we spent most of 2009 using our organizational nickname, TOPP, more prominently in our identity.  While “TOPP” is easy to say and remember, as with most acronyms, it’s pretty meaningless on its own.  I’m sure it will take us a while to erase TOPP from our vocabularies, but I think it’s the right move.

To round out the logo history, here’s the one that was in service through 2008.  I like it, however for the twenty- and thirty-somethings in the room, “OPP” means something a bit different (can you say “harm me with harmony”?).

Of course, to go along with the rebrand, we’ve updated the OpenPlans website, attempting to streamline our messaging along with our logo & brand.

We’ve been struggling with a meaningful, succinct tagline for quite some time, and for now have settled on “We make cities work better.”  A while back, I wrote about the idea of “making cities easier to use” — since then, we’ve taken that idea and adapted it a bit.  Making cities work better is a better representation of our intentions, as it’s multi-directional (i.e., we’re not just “using” cities), and it hints at the digital infrastructure that we’re building.

Also, for the first time, I think we’ve successfully articulated how our software development, technology strategy and journalism activities are connected, as part of what we’re calling “the new civic infrastructure.”

Lastly, a major goal of the redesign was to make it more clear what we do and how people can work with us.  I guess now we just sit back and wait for the contracts to roll in…

Here’s what the website looks like today:

And for another trip on the Wayback Machine, here’s a look at 2009:

2008:

and 2007:

That’s it.  Hello, OpenPlans.  Nice to meet you.

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Apr 21, 2010

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Design

Interview on the Engadget Show is live

A few months ago, I did a short interview for the Engadget Show on the state of real-time bus information here in NYC.  The interview was for a video segment which led into a live interview with the reporter I worked with, Rick Karr.  The whole episode is now available online.  Before our section is an interview with Nicholas Negroponte, talking about OLPC and visions for the future.

35 min into the show is our part.  We’re standing right outside of Penn Station, checking out the real-time bus information that’s available now on 34th Street via dynamic signage.  We talk a bit about the current state of real-time on NYC buses and the challenges that the MTA has faced getting real-time implemented thus far.  In the live interview, Rick mentioned some of the work we’ve been doing at The Open Planning Project, including the iPhone-based OpenBusTracker experiment we did last summer, and our general belief that real-time can be implemented for less than you’d expect using commodity hardware and open source software.

Of course, it’s tough to watch yourself on video, and it’s even tougher to hear your own edited answers.  Note to self: work on snappier soundbites!  But it was really fun doing the interview, and great to get the real-time transit discussion out there to a wider audience.

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Mar 26, 2010

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Cities, Open Source, transit

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