I feel a certain kinship towards the founders of Blippy. Not because I know them well (I’ve met Philip Kaplan aka Pud only once) but because they’re pushing the limits of what people are willing to share about themselves online. While we at Plancast are encouraging folks to be more open about their future whereabouts, the team behind Blippy is hoping that people are ready to share their purchases with the world.

Both of our services are also very new, and as to be expected with new web services, there’s still lots of work to be done on both. In the spirit of tech camaraderie, I thought I’d offer up a few (unsolicited) suggestions for Blippy.

1. Give us digests. The current user experience is primary centered around a mostly reverse chronological, FriendFeed-like stream of purchases. This is okay but I’d prefer to check Blippy as often as I check Mint (which is to say, once a month). And when I do, I’d like to see an overview of sorts that breaks my friends’ spending habits down. Tell me what their biggest and smallest purchases were; their strangest purchases; their spending habits (have they been splurging on clothes? buying a lot of airline tickets); and overlap in their spending (who’s buying the same things? what are the trends among my friends?). Pretty graphs might help. Maybe incorporate some maps so I see where about town people are spending their money. Who knows, I might visit once a day if the data updates constantly with new trends.
2. Provide more info about the purchases. Right now each purchased item is displayed in tiny blue type. Blow that up if it’s available and give me context (a URL to where I can buy/view more info), an image, and a description. Show me who else I care about has also bought it.
3. Let us condense/hide comments. I realize that much of the interaction onsite right now is around the comments people make on purchases. But I’d personally rather locate an interesting purchase then choose to view the comments around it.
4. Add a “Want” button. The “like” button is a step in the right direction, but perhaps a “I Want This” button would be more valuable. It signals a higher level of interest in the purchase, leaving simple “oh that’s cool” expressions for the comments. You could have profiles list not only purchases users have made but the items of their friends they want. Analyze this data in aggregate to see who starts purchasing trends (fashion being an obvious area).

My 2 cents.

I’m happy to announce that the site I’ve been working on for the past half year or so - Plancast - is now available in public beta. If you haven’t tried it out yet, please give it a whirl and send us your thoughts. I suggest you get started by posting a few plans that may be tucked away in your personal calendar. Share them on Plancast and you’ll be surprised by how positively other people respond after hearing about them.

What does Plancast do, you ask? It helps you share your upcoming plans with friends and learn about what others will be doing in the future. Imagine how awesome it would be if we all had a better idea of what everyone was up to in the next few hours, days, weeks, or months. Thinking about grabbing drinks with friends tonight? Going to a concert tomorrow? Heading to a conference next week? Taking a trip next month? Great, it takes just seconds to share each of these plans. Your plans will reach not only your subscribers on Plancast, but your friends on Twitter and Facebook as well, if you so desire. The service a great way to spread the word about the informal social activities you do every week, whether or not you’re looking for people to join you.

It’s been an amazingly fruitful journey getting to this point, and things are especially exciting now that the site is finally live and in such good shape. I launched an “alpha” version at the beginning of September, but since it was so rudimentary, I only sent it to a handful of people for testing. With this more functional beta version (released just this past weekend), I’m encouraging everyone to check it out and invite some friends along. We’re already seeing a broad range of people take a liking to it.

I’m also happy to announce that I’ve brought aboard Jay Marcyes as a co-founder. Jay is a programming beast, not to mention a thoroughly nice guy, who was previously working full-time on another consumer internet app called Noopsi. I’m truly lucky to have him, and I encourage you to get acquainted on Twitter. For ongoing updates about Plancast in general, you can follow the official Twitter account as well.

When users want to find their friends online, they think of Facebook first. For many users, “Facebook” is nearly synonymous with “social networking”. They wouldn’t think of using any other “social” service because, after all, their friends are all on Facebook. As far as the social networking industry is concerned, this dedication constitutes a massive customer lock-in, because no matter how much better you can make a social application, you’ll start off not only without the preestablished connections enjoyed by Facebook; you’ll also be fighting against the reluctance of Facebook users to try an application outside of the Facebook ecosystem in uncharted territory where most of their friends do not exist.

The Facebook developer platform (which includes the ability to write widget-like applications for placement on Facebook.com, as well as the ability to extract data about users for integration into applications on other domains) narrows this gap only slightly. For all of Facebook’s talk about wanting to open up, its platforms APIs and policies empower third-party developers with only so much data and user access. Compared to the power that Facebook wields as chief overseer of its data and users, outside developers can query just a sliver of its social graph. And of that sliver, they can only store certain data in certain ways for certain periods of time. The restrictions add up so that Facebook integration delivers but minor, complementary benefits to most third-party sites.

To break things down a bit, the platform can be divided into push and pull components. Many of the APIs are designed to let you pull data about Facebook’s users and leverage that data in your applications. Others are designed to let you push data from your application back to Facebook, usually for sharing user activity with friends there. These push mechanisms are the most critical for most third-party developers, because users want to retain contact with their Facebook friends and share activity with them. The data you pull from Facebook about users is generally less interesting, if only because it’s pretty generic. Unfortunately, the push mechanisms are pretty weak since they don’t let you reliably send data to individual friends of users, whether through Facebook’s proprietary messaging system or email notifications. Your best bet is to rather bluntly dump something into the homepage stream and pray that it catches enough friends’ eyes to make an impact.

All of this is to say that Facebook still has a huge competitive advantage over other social networking companies (whether on-platform or off) because it controls a valuable social graph — and particularly the email addresses that come along with it. However, the social graph is not a divinely produced thing. And it’s not a permanent, exclusive good. On the contrary, I believe the social graph is rotting on Facebook and starting to be reproduced elsewhere in better form.

The main problem is that people’s real-world social graphs change often and automatically, while their virtual representations on Facebook change mostly uni-directionally and manually. In other words, friends come and go in real life; but on Facebook, they usually just come. Friend lists tend to get bloated over time because users have a harder time defriending each other virtually than in real life. And even if they are going to defriend each other virtually, it has to be a deliberative effort, unlike in real-life when you just stop seeing certain people.

This problem is particularly acute for Facebook, because its earliest adopters were college students or high school students who have undergone significant changes in their lives over the last few years. They no longer see many of the people who they once friended in school. And they aren’t inclined to remove these friendships from Facebook because they’re lazy, fatigued or simply too polite.

The ill effects of this discrepancy would have been tempered had Facebook stuck to its original value proposition of static profiles. However, Facebook has undergone a major shift from a static directory to a dynamic communication channel. This shift is embodied by its decision to remake its homepage into a Twitter-like stream of directly published content. When you open up Facebook these days, you’re bombarded with little bits of information about your Facebook friends’ lives. It’s no longer primarily a place to browse people’s profiles (and associated photos) like Wikipedia pages.

Don’t get me wrong, I love the “real-time web” as spawned by Twitter and advanced by FriendFeed. But Facebook has hoisted this dynamic paradigm onto a user base that didn’t expect it, didn’t ask for it, didn’t prepare for it, and perhaps doesn’t want it.

I’ve already discussed why this last factor is such an issue. But assuming the idea of micro-sharing does grow on Facebook users, they haven’t established the right audiences for it. Friendships haven’t been made on the basis of content consumption; they were made first to simply acknowledge your friends and later to gain access to their profiles (once Facebook opened up for non-students and became a less trusting environment). Sure, the news feed was introduced rather early on and aggregated information about those who users decided to friend. But the inability to post content directly and immediately to all of your friends’ news feeds created an important sense of distance between you and them — and made it easier to coexist on the site with those friends who weren’t really your friends anymore, or those who you didn’t ever care to hear from much.

As a content producer, my predefined social graph on Facebook makes me reluctant to publish there, because I don’t feel as though my friends have indicated an interest to see my constant updates. The problem I have as a content consumer is just the flip-side: when I load up Facebook, I see content produced by people who I don’t particularly want to hear about or from.

Facebook has provided various ways to sort friends into lists and hide individuals from your stream, but these tools are daunting and perhaps ultimately futile. I spent 20 minutes alone last night organizing just my friends with first names that start with letters A-C. With almost 800 friends, I’m reluctant to keep going. And I imagine that most Facebook users don’t even have the wherewithal to try in the first place.

Facebook may try to address this content audience problem by introducing a Twitter-like follower model. The site already asks you when friending someone new whether you want to see that person’s updates in your home stream. But users won’t be doing this retroactively, and it adds complexity to an already complex site. Privacy and distribution controls simply aren’t going to solve the problems of an over-encompassing social graph.

What does this all mean? Well, Facebook’s golden goose (the social graph) may not be so golden after all. It changes as users change. And it’s not really even a singular thing. People have multiple social graphs; Facebook just tries to roughly represent them all by clumping them together. When it comes to profile access, you may want to leverage a different set of connections than when it comes to status message streams. Facebook may have to make a decision as to which particular social graph it wants to represent for its (constantly growing and diversifying) user base. It may not work for the company to be all things social for all people.

It also means that there’s a massive opportunity for other social sites to give Facebook users a fresh start with fresh new social connections. I’m biased here, of course, since I’m working on social software. But this opportunity is seen in the rise of Twitter, which can attribute much of its success to the mere fact that it’s not Facebook. When you sign up for Twitter, you can determine anew who you care about - whether that’s your new friends or coworkers, or celebrities, businesses and media outlets. Facebook will no doubt remain a dominant social network for quite sometime, but it’s dominance does not preclude the rise of other, independent social applications and services.

I’m happy to announce some exciting news regarding my startup. I’ve officially incorporated as Worldly Developments (yay for Delaware). Just a teaser of a website currently, but something I can print on my new business cards.

The reason for incorporation? I’ve raised some (micro-)seed funding from fbFund. Since that requires a legit corporate bank account and the filing of other important paperwork, my mom has also assumed the role of Chief Financial Officer (employee #1! thanks Mom).

FbFund isn’t just an investment vehicle; starting this summer, it’s also an incubation program in Palo Alto. So while I planned on moving to San Francisco earlier this month, that’s been put off until the end of summer so I can enjoy the office space they’ve provided for us just off University Ave. It’s one of the old Facebook offices, and all of the participating startups (~20) started moving their stuff in there just a few days ago.

From now until mid-August I’ll be participating in the fbFund program, which basically means hacking away at my application as I would anyway, except with additional support/mentorship/resources provided by Facebook and others. I’ve already met a fair number of the participants and organizers, and I must say, it’s a refreshing change of pace to work around like-minded people again instead of coding solo in my bedroom or at the cafe.

I also just got back from a quick trip to Japan and China as part of GeeksOnAPlane. Thanks to Dave McClure for bringing me along as a media partner of sorts (I relayed what we learned as a return guest writer for TechCrunch; see these posts in particular). The people in the traveling group were amazing, both personally and professionally, as were the people we met along the way. If you haven’t visited East Asia, I highly encourage you to do so.

I’ve been thinking a bit about the Apple App Store recently, perhaps because I’m starting to think more about developing a mobile application that will complement my site.

One of the amazing things about the App Store — perhaps the most amazing thing — is how easy Apple makes it for users to pay for apps with small amounts of money (micro-transactions, if you will). Are you a developer that wants to sell an application for just $.99 a pop? Easy. Just create your app, submit it to the store, and start earning money. You don’t even have to worry about going the advertising route. The strategy instead is primarily about providing a free version of your app that then gets users warmed up for your paid version.

Apps in the App Store aren’t that different from web apps. They are both internet-enabled at their core and provide rich communication and data retrieval services for their users. Sure iPhone apps run in Objective C instead of Javascript, etc. But that doesn’t matter to the regular user who decides to pay for an app on their iPhone. Both are apps either based, or quickly retrieved, from the cloud.

One of the problems that most internet startups face is the looming question of “how the hell am I going to make money on my site even if it becomes successful?” The internet industry is often mocked because it doesn’t readily provide dependable answers, at least not ones that are not easily undermined by general economic factors.

No web developer wants to deface their sites with Adsense or banner ads. Online advertising is (with few exceptions) anti-consumer and difficult to do “right” (as in, design to really capture users’ attention and generate modest rates of return). Wouldn’t it be great if we could just design sites that sell like iPhone apps?

Imagine visiting a site’s landing page, getting a description and some screenshots, and then seeing a button that says “$1.99 for full access”. If, as a user, you could click on that button, enter a password, and then immediately have lifelong access to the site — I bet you’d do it. $1.99 is a price lots of people are willing to pay, even if there’s a risk involved with trying out the site and then finding out you don’t like it.

I don’t know nearly enough to understand why this hasn’t happened, even though I’ve read a fair amount about how online micropayments for sites have been heralded for years but have never materialized. Apple has made things happen on the iPhone because they’ve created a closed system that makes it really easy for end users and developers alike. As a user, you give your credit card information to Apple once and they only charge it when it makes sense (since charging every micropayment individually would drive up transaction fees).

Why can’t someone do this for the web? It seems to me we just need a company that a) people trust with their credit card information and transactions, and b) knows how to build the right distributed technology that will get adopted by developers. Google comes to mind since it’s tight with developers and very trusted among users. Maybe browsers like Mozilla are better situated, however, since they control the “device” within which users browse the internet (just as Apple controls the iPhone). Then again, Google has its own shiny new browser (Chrome) so they’d have that going for them as well.

Such a payment system could revolutionize how websites are monetized - and consequently, how they are made. Businesses and their users would both stand to benefit greatly. Here’s to hoping this happens as the web matures.

• It’s hard to communicate the immediate value to users, especially ones that join the site before any of their friends
• It’s extremely difficult to predict what kind of service users are going to respond to, and which features in particular are necessary. Better to release something straightforward, see how users like it, and evolve by coupling user feedback with theory
• When there’s only one developer (me), it can feel overwhelming to build out a complicated system all at once. After awhile, there’s a strong desire to launch something so it feels like you’re making tangible progress. Milestones are key when you’re the only one laying out your priorities
• Once you’ve released something - even if it’s only a smaller part of your broader vision - it’s easier to explain to other people what you’re building. It’s no longer just about pie in the sky ideas - you can send them a link, have them see what it does, and then explain where you plan to take it.
• There’s an intrinsic value to building something simple. Users don’t want to think too hard about how to use applications, and if your application only does one thing - and it does it well - they’re more likely to come back.
• When you release a web app these days, you need to market it effectively, otherwise you’ll get drowned out by all the other options people have online. One effective way to market is to make your site compatible with the places people already visit, namely social networks like Twitter and Facebook (at least in my case). It’s easiest to piggyback off of these sites if you create something particular that enhances them; then you can go from there and develop something more sophisticated that stands on its own.

Last week I launched the narrowed site into private beta, inviting only a dozen or so people. I’ve already received a laundry list of features/change requests, and I’ll start opening the site up more broadly when I feel as though I’ve addressed them adequately.

I’m also happy to report that I’ve been chosen as a finalist for fbFund, which affords me some money to advertise on Facebook. More details and a list of the other finalists here.

The “scent” coincided with a certain epiphany concerning the design of my service. If you read my last post, you can get an idea of what that epiphany might have been all about (I’ll let you read between the lines on that one - it shouldn’t be too hard). The original value proposition of my service remains the same but I think I now have a much better idea of how to create that value.

I’ll leave it at that, partly because I’m getting more protective of my ideas as they mature and partly because I’m much more interested in getting version 1.0 ready than talking about it. I’ve talked a bit of talk, and now I need to walk a bit of walk.

More to come later.

The immense amount of attention lavished on Twitter these days signals two main things. First, that web innovation in general is going through a transformative period, one in which we don’t see a lot of breakout technologies because the industry is struggling to redefine itself in the wake of economic collapse and the exhaustion of innovation. Twitter stands out because it’s a counter example to this trend, a company that’s going mainstream and perplexing people all at the same time. It’s a paradigm changer; people are simultaneously obsessed with it and confused by it.

Both the confusion and the obsession will pass in time, just as it did for Facebook, the last internet rockstar to emerge before Twitter. Facebook is no longer the buzz maker it was about two years ago and Twitter will no longer intrigue us two years from now. And like Facebook today, it’s primary mark on the web landscape will have been made, even though it will remain a powerful force on the web and continue to innovate.

The making of this mark is the second reason why there’s so much attention lavished on Twitter right now, especially by technology pundits who pay constant attention to the effects of breakout services on their peers and descendants. The mark is both simple and profound, and it consists of demonstrating the potency of so-called “microblogging” for the distribution of social information.

Facebook may be credited with popularizing the “news feed” - a continually updated stream of information about people you care about - but Twitter boiled the news feed down to its essence. On Twitter, the news feed doesn’t extract changes from secondary profiles and associated applications. It’s not deducing news about your friends by passively monitoring their activity elsewhere, as the Facebook news feed did almost exclusively until very recently.

No, on Twitter, the users contribute directly into the news feed itself. The news feed is the main feature, not a method of surfacing the most contemporary information in a system. And the content that users add is very basic: simple strings of text no longer than 140-characters in length. Sure, Twitter could have allowed users to post images, movies and other types of data into the feed. But it’s creators - partly restricted by the desire for all tweets to be SMS-compatible, and partly influenced by the legacy of blogging - kept things stripped down to their basics.

Twitter remains a stunningly simple application. That’s its strength, but the simplicity also creates an opportunity for other services to apply Twitter’s model to other ends. Facebook most notably just appropriated Twitter’s user experience with the redesign of its homepage. Apparently, Facebook thinks that the Twitter model (combined with the related FriendFeed model) is the best way for friends to exchange information of all types - not only status updates but links, images, videos, and more. And months prior to that, Yammer did something similar for the workplace by releasing an enterprise microblogging service.

This is just the start. Over the next few years, we are going to see social services across the spectrum appropriate and expand upon the basic functionality of Twitter, because there are needs that Twitter doesn’t (and can’t) fulfill, either onsite or through its API. Since all software is becoming social, expect the Twitterification of software in general.

Why is the Twitter way of communicating so powerful - and consequently, why will others borrow from it? Microblogging is passive, it’s distributed, and it’s easy. In other words, people can digest and respond to tweets as they please. There’s no technological or sociological pressure for them to consume or act on information in ways that are disproportionate to their interest level. When you post a tweet, it gets blasted out to many recipients all at once, unlike email which is architecturally designed for a limited audience. And each tweet demands very little from its users - just a simple thought or observation.

So, Twitter has set the standard. It’s currently proving that its model can appeal to mainstream audiences, who actually appear capable of grokking its utility (which was not always a given). But this is just the beginning - just as “social networking” features pervade services of all kinds these days, microblogging will also become ubiquitous - and it will assume different forms depending on the various needs at hand.

Today marks the completion of my first week working on my first startup. So, I thought it would be a good time to share some of the things I’ve learned already about what it’s like to build your own web service from the ground up and as a full-time job.

I’m going to try to provide this type of update on a regular basis for two main reasons: 1) so others can get a sense of what it’s like to start a dot com these days, especially if they are thinking about doing it themselves; and 2) so I have a record to look back on later to see just where I’ve been and how my thoughts may have changed along the way.

When I decided to strike out on my own, I expected that the hardest thing would be to keep up morale, both for myself and for anyone who joined me. It seems as though a lot of startups wither away because their founders give up hope on their ambitions. The threat of demoralization appears the greatest for startups that are trying to do something really new and innovative, something for which the market can’t even indicate demand yet. Even with less radical ideas, there are always naysaying thoughts nagging away at the back of the entrepreneur’s mind; for example, “if this was such a good idea, why isn’t someone else already doing it?”, “if this were even possible, wouldn’t others be already doing it?”, “hasn’t X and Y companies already kind of tried this?”, and “couldn’t company Z easily move into this space and wipe out the market opportunity for my fledgling startup?”.

Even though it’s only been a week, these are thoughts that I have had to handle carefully. On the one hand, it’s necessary to constantly question the core value proposition of your startup. If you don’t, then you’re bound to build something that people don’t need or want. Whether I’m in the shower or walking down the street, I’m frequently turning ideas over in my head, looking for weaknesses in them, and trying to expose poorly made assumptions that could turn into Achilles’ heels.

On the other hand, a startup founder needs to be stubbornly optimistic, lest he or she succumb to the overwhelming number of (legitimate and illegitimate) doubts that may arise. As the debate from this week over Zuckerberg’s decision to look beyond user feedback brings into focus, its important for a founder to say “yes” even when (many) others say “no”. If the man on the street dictated product design, we’d all be driving Volvos. Great ideas (perhaps by definition if not just in general) shouldn’t be easily appreciated until they’ve been executed, and sometimes not even in the short-run after they’ve been executed. An entrepreneur needs to internalize this belief and learn how to endure resistance and skepticism from those who don’t readily share it.

Currently, I have a user base of just one, so I don’t have to defy millions of faithful users when making product decisions. Mostly doubts arise when I’ve shared my ideas with friends, family and basically anyone willing to listen. Some of the time people get the value proposition instantly and it clearly resonates with them. It’s immensely satisfying (despite what I just said above) when people respond with “wow cool, that sounds exactly like something I would use.”

Other times, people scratch their heads and almost reflexively assume the role of devil’s advocate: “so this is kind of like a cross between X and Y websites…right?” or “shouldn’t this just be a facebook app?” (the modern day equivalent of calling someone’s website idea a gizmo). It’s important to listen to those who still need convincing, because there will be a lot more of them and their concerns usually inform your concerns. But it’s equally important not to let their skepticism deflate your enthusiasm for the project. I’ve found that the best way to reassure myself in these situations is to think about what it might have been like for the founders of Google, Facebook, or Twitter to sit down at the beginning of their projects and get feedback from friends (”why do we need another search engine?”, “why would I want to put my personal information online and then tell a site who my friends are?”, and “who cares if I’m brushing my teeth or watching the basketball game?”)

Keeping up morale is particularly important when you’re flying solo, because you don’t have a cofounder who will constantly reassure you of your decision to follow a path to no certain end. Also, when you’re at a regular job, you may not know if the company will succeed but you can be fairly certain that you will succeed in your delegated role. Your projects are usually well-defined and limited in scope, and as long as you get them done well, you have something to put on your resume and feel good about when you head home at night.

But when you’re starting a company, the goals are not defined for you and you’re wrapped up in the success or failure of the enterprise as a whole. If you spend two years working on a startup that ultimately falls through, I imagine it’s a much greater personal burden than spending two years working at someone else’s company that goes belly up.

So far, morale has been good for me. I’ve already experienced a bit of the “rollercoaster” effect that I’ve heard others describe, where emotions swing from high to low, and back to high — sometimes on an hourly basis. But my project is getting increasingly more exciting as it develops, even though the first weeks are all about baby steps (drawing mockups, conducting general research, checking out developer documentation, hacking together the first pieces of code, etc.)

There are also definite benefits to working for yourself - and from home, as I currently am. There’s none of that (often unnecessary) pressure to please anyone but yourself, and I suffer less from unhealthy stress. Sometimes it feels a bit like I’m on vacation, but then I remember that I’m actually working longer and on weekends now. It just feels like vacation because the work is thoroughly pleasurable, at least so far. I also don’t have to deal with the formalities of a normal job, like going into an office or taking breaks only when it makes sense for the organization as a whole. When you work for yourself, you can roll out of bed and immediately start getting stuff done. And if you feel like 2:30pm is the perfect time to take a break and hit the gym, you can do it without feeling like anyone’s judging you for leaving in the middle of the day.

So that, in a rather large nutshell, is what I’ve experience so far. The prototype (codenamed “Magellan” - thanks Jason) is coming together, and I hope to have the first version ready to share with friends and family by sometime in June. I also plan to start inviting people off the waiting list before soon after that.

For related reading from someone with much more experience than me, check out Paul Graham’s essays, especially this one.

As Erick Schonfeld was kind enough to announce in a post on TechCrunch last week, I’ve left my position at TechCrunch to build and run my own startup.

In many ways, this is what I intended to do all along, at least ever since I graduated from college almost two years ago. After joining TechCrunch in 2007 (as an intern anticipating that I’d only be there for a couple of months), I quickly realized that it would be a great place to lay the groundwork for my own venture. Working there keeps you in constant connection with the consumer internet technology scene, since you’re always reading news and analysis (especially as a writer) and meeting people from all parts of the industry (PR, management, investment, development, etc.). Of course, it doesn’t hurt to work for a brand that has great name recognition in the Valley, especially when you’re returning from four years in Maine - basically Siberia, as far as people around here are concerned.

I learned a lot about new media, internet technology, the culture around internet technology, and the inner workings of a startup during my time at TechCrunch - lessons that perhaps I’ll explore in a later post. But now my sights are set on building a viable web service (and later, a profitable business) in a down economy…something that with any luck won’t fall to the wayside like so many of the startups I witnessed at TechCrunch. It’s not going to be easy; in fact, I’m sure it’s going to be one of the toughest things I ever try to pull off. The reassurance is that even if I fail, I will have learned and experienced much along the way.

Ok, so enough sappy reflection and introspection. What am I actually trying to build? Or as my friends and family keep asking, “What’s your website about?”

Let me start to answer that question with a description of how the idea for my startup came about. When I moved back to the Bay Area after living in a tightly knit community at Bowdoin, I had a new set of needs - most of them social. And like many needs, they could only be fulfilled by gathering information, not just once but on a continual basis. For example, I wanted to know:

• Which of my friends now live in the Bay Area, and where exactly do they live and work? Do any of them live together?
• Who do my friends know in the area that I might like to know? Do they live near me, and what kind of people are they looking to meet?
• Where do my friends and their friends like to hang out on the weekends? Where do they go out to eat, and where do they do other things like going to the gym or perhaps volunteering in their free time?
• What kind of plans do my friends and their friends have coming up in the near future? Are they thinking about going somewhere fun in San Francisco, or do any of them plan to go running around Palo Alto?
• Are any of my friends actively involved in particular interest groups? Maybe a few get together with others to, say, play tennis or hit up the farmers market every weekend?

Questions like these are just begging to be answered by web services - especially by the type of those we’ve seen sprouting up in the past few years - because they all call for social information. Unfortunately, no web service adequately answered them in 2007, and still none does today. Sure, we have a plethora of sites intended to help you figure out what to do and where to go in your area. But those with the most data are not personal enough (i.e. they don’t help you see the world through your existing connections), and those that are personal lack data, and the proper architecture for that data.

So, on a high level, I’ve set out to build a service that will answer the questions above and many others, a service that will help you engage more actively in your community. Call it a city or location-based social network if you want, but hopefully you’ll see that those terms tend to misrepresent what I have in mind. I’m not looking to set up a site where you simply post a profile for others around you to view and write things on. I’m looking to set up a site that makes it easy for you to share information about who and what you know, and what you do, around the area in which you live. And conversely, a site that makes it uber-easy to digest useful local information shared by others.

No service does this to my satisfaction yet, but there are many related sites out there. After all, the desire to meet people and learn about what’s going on around you isn’t new. Here’s a list of the names currently scribbled on my whiteboard:

• Loopt, Brightkite, et al. - Services that detect your current location via a mobile device and then broadcast that location to your friends are all the rage right now. Perhaps we’ll encroach more on each other’s territory down the line, but I don’t really care about helping users find out that their buddy is in the bar next door. I care more about providing you with social information from and about the area in which you live.
• Yelp, Goodrec, Citysearch - Local review sites are great since they have a ton of information. But unfortunately, the information comes mainly from the public at large. Goodrec is a step towards personalization and simplification, but reviews and recommendations need to be even more socially focused (Whrrl had the right idea but didn’t execute successfully).
• Facebook, MySpace, TheScene - “Traditional” social networks, no matter how innovative, define themselves broadly. They aren’t interested, for the most part, in local discovery. Look at how Facebook abandoned network pages. And new sites like TheScene ostensibly help you go local but simply aren’t innovating much in how people publish and share information (for this, just look at the ripples that a deceptively simple service like Twitter has made).
• Match.com, Okcupid, Mixtt, Engage, etc. - Dating sites are still holding down the fort when it comes to local discovery services. One problem - they suck, and they only serve one particular need (ok ok, it’s a good need to serve, but even that need can be served better). It’s great to see sites like Engage and Mixtt try to innovate by making things more social, but so far their efforts haven’t worked out all that well.
• MeetUp, Upcoming - Sites that help you meet up with interest groups and attend local events. Good. But who are all these strangers?
• Outside.in and other local news sites - Local news is also good, but if there’s anything that’s easy to find online, it’s news. And local news is often far more boring than national news, so it’s an uphill battle to build a service that just revolves around this.
• Craigslist - Amazingly great and amazingly bad at the same time. I’d like to think that this site isn’t a testament to how the last 10+ years of web technology advancements don’t matter when it comes to local classifieds.

Those are the services on my mind as I start the process of creating something new and improved. What did I miss?