If you haven’t used the product, it’s a pretty simple proposition. You download the Highlight app from the iTunes store, connect it to your Facebook account, and then you let it run in the background. Periodically, the app will send you a push notification telling you that someone you know or a friend-of-a-Facebook-friend is nearby. The UI gives you some sense for the strength of connection (based on share connection). Here’s a screenshot of what it looks like:

Other than the occasional push notification, you don’t hear much from Highlight. It doesn’t prompt you to check in or do anything else. At the end of the day, you can also scroll through your log and see all of the people with whom you’ve crossed paths in the last day or two.

But this is not the first service I’ve contemplated using that offers passive location tracking. Google Latitude has offered passive or background location sharing on mobile devices for some time. I never turned it on because it just didn’t feel like a service I wanted to test. So either the market has changed, I’ve changed in terms of what I’m willing to share, or Highlight has gotten a few things right. As much as I think I (and others) have gotten comfortable sharing more info in general, I think Highlight has gotten a few of the design constraints for the service right and that has a lot to do with why it doesn’t feel creepy in the way other services do:

There is no granular check-in – Unlike some other products, you don’t have to take an active action to tell the service where you are. That takes a lot of the friction out of location sharing and also makes it feel like less of a stalker app than other things I’ve seen. Also, the push notifications tend to tell you “Person X is nearby” not “Person X is at Location Y right now” – it’s a subtle but important difference.

The target broadcast radius can be segmented to friends and friends-of-friends – One other thing that I think makes the service interesting is that the broadcast network is your Facebook friends (people you presumably like) and some of their friends. It’s not something designed to have anyone in the world be able to figure out where you are or to allow anyone to follow your movements. I think an asymmetric follow model here would be kind of creepy – not sure I would want just anyone who knows my username to be able to peer into my location stream. For the record, I did hit the privacy toggle to turn it on for friends-of-friends only as opposed to everyone.

Because it runs in the background, it’s not in your face reminding you that it’s keeping track of where you are – Last but not least, the service sends me enough push notifications to remind me that it’s running and to alert me that there are potentially interesting people around but not so many that my phone is constantly buzzing and not so few that I forget about the app entirely.

The one big challenge I have with Highlight is I’m trying to figure out the service interaction model and etiquette. Knowing that someone is nearby is an interesting piece of information. But I don’t yet have enough context to know whether I should reach out to him or her, whether he / she is just passing through the neighborhood, or even what action I should take given that I know someone is in the area. So for now, I’ve just been observing how others use the service and how people reach out to me. I’ll be curious to see how the interaction model evolves.

Overall, this is one of the more interesting location-sharing apps I’ve seen in awhile. Very curious to see how this one unfolds.

Many seed stage companies that raise money on convertible notes do not have outside BOD members or regular BOD meetings. The “nice” thing about regular BOD meetings is that they are an opportunity to talk about the most important issues facing your company and get feedback from your investors.

In the absence of formal BOD meetings, I think it’s a good practice to keep your investors up to speed on what’s happening with your company. There are four things I try to include in my monthly update to investors and that I find helpful to get from our portfolio companies:

1. Are you going to run out of cash in the very near term?
This one is the most important one, in my opinion and should always be an above-the-fold item in the summary. Giving investors a sense for how the company has performed in the past 90 days helps smooth out monthly variations and gives investors a sense for how burn is trending. One simple thing to do is to just show a very high level P&L for the last three months including revenue (if applicable), expenses, net burn, and closing month’s cash.

The reason that three months helps is that it gives you a sense of trend. With those three data points, an investor can look at how your net burn is trending and figure out when you’re like to run out of money and when you’re likely to need to raise money. This is super helpful because investors and entrepreneurs don’t always have the same sense for a) how low closing cash should be allowed to go before taking action (raising money, cutting burn, etc) and b) how long it will take to raise new money and under what terms. You can avoid surprises over your cash position and cash needs by doing something along the lines of what I’ve suggested above.

2. Have you decided to make any major changes to strategy or approach based on what you’re learning about your target market?
Of only slightly less importance than cash position is whether you as a company have made or are considering making any major strategy changes. This can be anything along the lines of slight pivot from the original idea to a total pivot in a new direction. One thing worth considering, though, is whether the magnitude of the change is something that should be communicated in a monthly status update or discussed with your investors in person or on the phone. Shifting 10-20 degrees in terms of product and focus? Going to be a bit late on your launch? Probably not a huge deal. Planning to pivot and address an entirely new market? Doing something else drastic? In many cases, a monthly status update is not the ideal way to deliver that information unless the change has been in the works for some time.

3. Are there any important issues related to the team or internal workings of the company that are worth discussing?
This one is usually pretty straightforward. Have you made any key hires? Have any key team members left? Any other issues on the team side worth bringing up? Again, if there are sensitive issues (co-founder planning to depart, HR issues, etc), a monthly email update might not be the best way to address them.

4. How are you tracking against your core KPIs?
Even pre-revenue startups have some key performance indicators (KPIs) that they track regularly. It could be monthly active users, registered users, funnel conversion metrics, etc. What are those metrics for your business and how are you tracking against them.

This list is by no means everything you could include. Important product updates, press mentions, asks for help and assistance, fundraising plans, and a host of other things are all worthy of inclusion. But I think the four points above are the bare minimum to include.

Whenever I try out a new product, I always try to ask myself what question the designer was trying to answer by building it. When I first started using Path, the core question behind it seemed clear to me:

What kind of information would you share if you could keep it within a network of people you really trust and like?

I think the answer is simple – you’d probably be willing to share a lot, including location, what you’re thinking, the people with whom you’re hanging out, and whether you’re asleep or awake. In my last weeks using the new Path, I think they’ve succeeded in creating something that feels useful and interesting of your Facebook graph has become too big and spans too many parts of your life. A few quick thoughts.

Features that feel creepy in a large social network like Facebook don’t feel creepy on Path. When I saw the first, “Person X visited your Path” message in the tray, I was a bit taken aback. It seemed weird to have that kind of insight. But once I realized the people visiting my Path were close friends, it didn’t feel so weird. I kinda liked it, actually.

Choosing which friends to include on Path is hard. Because Path feels like the product is geared around feeling comfortable sharing with a tight trusted group, it really matters who you include. I’ve been sitting on a bunch of Path requests because I’m not yet sure which people to invite.

Many people I know have Facebook graphs that span work colleagues, casual acquaintances, school friends, close friends, and others. Having an amalgamated graph with different contexts generally leads to people thinking harder about what to share on Facebook. I know that my sharing habits have changed as my graph has grown – I share less and the things I share are (I hope) interesting to a large chunk of my Facebook friends. I’ve already seen my small group of friends sharing things on Path that they weren’t sharing on Facebook. It will be interesting to see whether people with large social graphs opt for something like Path or go back and curate their existing friendships on Facebook to facilitate context-appropriate sharing.

As always, comments are open or you can message me on Twitter @chudson if you prefer.

Yelp has succeeded by becoming the de facto place to review restaurants and places of interest. You don’t need “friends” on Yelp to get value from the system as it depends on a combination of crowd feedback and good SEO to show up when you’re trying to get a read on places to go. Yelp has done really well in proving out the business value in creating an advertising and editorial relationship with local businesses. They’ve done such a good job, in fact, that they’re filing for a sizable IPO. But Yelp is becoming difficult to use for me for two reasons. One, the reviews are becoming too wordy – there are too many 500 word preambles about everything that happened prior to visiting the place before you get to the meat of the review. That’s too much reading for too little value. Second, reviews (over time) seem to converge on 4 stars. That’s not a problem with Yelp, it’s more a consequence of a 5-star review system – maintaining 5 stars is virtually impossible and who wants to go to a place that can’t at least hold 3 stars? That being said, Yelp is still useful for many and continues to grow.

While foursquare is valuable to me, I am not willing to open up my real-time foursquare checkin activity to the world and the service has been pretty uninteresting if you don’t have friends on it (until today). I would have to say that foursquare is one of my favorite social networks. The downside of being a double opt-in / symmetric friend network is that the service is really only fun if you have other friends on it. They don’t have a real “follower” model – the data you get as an active user is a function of what your friends choose to do. But foursquare is gathering a lot of data. Ask a lot of location-based services companies whose places graph is the best and many of them will tell you that it’s foursquare. So they are doing a really good job of activating and engaging the community of people who like the product. But most of this data and insights is locked up in the service and accessible to those who are active participants. I believe that the non logged in user homepage is the first step toward making the service more useful to a wide range of users. It will expose (and make useful) a lot of the data they’ve collected.

The other step I see foursquare making is the level-based badging system. This provides them with a really unique opportunity. It could (potentially) mean a lot more to me to see the top-rated or reviewed sushi restaurants from people with the high-level “Bento” badge on foursquare because at least I have some sense that person has visited a number of sushi restaurants and should have a point of view. That’s not something that’s easy to get from Yelp today.

So, for what it’s worth, I think Yelp and foursquare are on a long-term collision course around being the authoritative source for local recommendations and reviews. If you have thoughts or comments, feel free to leave them below or message me on twitter @chudson

The key to understanding why this is the case is to put yourself in the shoes of your buyer, the event organizer. Putting on a large conference or event is like throwing a dinner party for a few hundred people – you want it to go as smoothly as possible without any major issues. As such, always remember the following:

Putting on events can be really stressful. So many things can go wrong, from food, to Wi-Fi, to speaker no-shows on the day of the event. Adding in a brand new technology product to the mix has the potential to do more harm than good for the organizer.

This applies particularly to technologies that will be deployed and used on the day-of the event. Tools that can be used in advance or following the event are different.

That is, at the core, why a lot of the pitches I see fail to meet the usage test. As an event organizer, there are a few questions you have to ask yourself before you deploy something else:

- If this is a new product, how do I know it will work? Am I the guinea pig?
- If I deploy it at my event and have problems, who will fix them?
- Will this actually add value to the experience for a large slice of my attendees?

Imagine yourself as an event organizer. You deploy some slick tool to your attendees and it fails on the day of the event. You have to get it fixed. And now. If it sounds like a lot of event organizers are conservative or risk-averse, it’s because many are.

The other area where I see real issues is with the business model for a lot of these products. A handful of products have approached me with one of two business models. One is to charge on a per-attendee basis for the product or service. This one can be challenging when I, as the event organizer, have no idea how many (if any) attendees will want to use the product. The other piece of the puzzle is to have a flat fee model. The flat fee model usually ends up being expensive for the event organizer and frankly often isn’t better for the event organizer in most cases.

By and large, event organizers have limited ability to pass on the cost of tech products and services that enhance the experience to the attendee. So any money spent on tech and tools comes right out of the event organizer’s net revenue.

There are two approaches that I think will work for those looking to sell tech products and I’ll summarize them below:

#1 – Wait for the world to catch up and have attendees demand the service is provided
This is clearly not helpful for startups. But in the past few years, there are two technologies that I think used to be considered luxuries that have risen to the level of customer expectation. Those two technologies are free Wi-Fi for conference attendees (and working the whole time no matter how many devices are on the network, I might add) and livestreaming or video recordings of the event sessions. Attendee expectations do eventually push event organizers to start offering new tools and services as part of the cost of doing business.

#2 – Build something attendees can adopt and use without having the event organizer involved
For most companies looking to sell into the events space, I would recommend thinking about how you can go direct to attendees without having to sell directly to the event organizer at first. Looking to build a tool to help attendees network and connect at an event? Try to go direct and find some attendees (via social media, via interest groups, etc) and see if they’d be interested in using the product. Find some way to build momentum among those planning to attend the event and then go back to the organizer and pitch him or her on using the solution. Taking the risk out of the solution and deployment plan can go a long way to making the sale seem less risky.

If you’ve had experience trying to sell products and services to event organizers, feel free to leave a comment here or send me a message @chudson on Twitter.

While my Facebook usage waxes and wanes, my overall time spent on social services has increased. Simply put, my time spent on Facebook is being replaced with time spent on purpose-specific social networks and services. I find that Facebook is just getting to be too wide of a jumble of people that I know in a wide variety of contexts. So the things that I share tend to be those that appeal to the wide variety of people who are my friends on Facebook. And I have no interest in trying to create groups / lists on Facebook to microtarget the audiences who might find a given piece of information relevant. I didn’t create my Facebook social graph with groups and grouping in mind. And, being in technology, I have a wide mix of friends, business associates, classmates, and others in my Facebook network. And I’ve found once you open up the gates and starting accepting a wide spectrum of requests, it’s hard to shut that off.

I’ve noticed that I’ve mentally sorted social networks into four buckets and my activity and energy is gravitating in a very specific way (namely “above the line” in the graphic below, with the notable exception of Twitter):

Increasingly, I find myself using more social services with the asymmetric follower model built for a specific purpose. More and more, my social tool usage is beginning to mirror how I used search during the rise of vertical search engines early last decade. I have one “core” service (Facebook) but am increasingly turning to other services for more specialized content – they just do it better.

In the same way that there was a set of categories where general search failed to provide relevant results (jobs, dating, travel, etc) there is an increasing set of circumstances where a purpose-specific network with an asymmetric follow model just works better for me. Quora is great for Q&A. Instagram is great for sharing photos. LinkedIn works well for professional connections. And I love foursquare for sharing location with a small set of friends. The only broad-based network where I find my time investment increasing is Twitter – and that’s largely because I like to share news articles and it’s very low friction.

When I first started using Twitter, I thought the asymmetric follow model might dominate simply because it’s easier to manage – you don’t have to take action on friend requests or curate who sees what. The more I use asymmetric follower services, the more nuanced I think the success criteria are:

Simple asymmetry is not good enough – you still need relevant people on the service. I’ve tried a few products in the social space that use an asymmetric follower model and they just didn’t have the right set of people on the service. There weren’t enough people on those services who could produce or point me toward interesting content. The low-friction approach wasn’t enough in and of itself.

Asymmetric follow allows me to follow topics or people, not just people. This is actually a big deal for me. There are some services where what I really want to follow is a topic, thread, concept, or idea. You can’t be “friends” with a topic or an idea – that’s a follower model for sure. Being “friends” with a topic is sort of like the early attempts to become “friends” with a brand on Facebook. The model just doesn’t work.

There are some categories where it’s hard to imagine an asymmetric alternative. I’ve been trying to think about what an asymmetric follower version of LinkedIn would look like. Part of what makes LinkedIn work is that you and the person have both opted in and agreed that you want to be connections, whatever that means to each of you. I struggle to think about how you could have an asymmetric follower version of a professional network. But I would have said the same thing about an asymmetric version of status updates and sharing until I saw Twitter.

And that’s why I really like asymmetric social services. I don’t have to make friend acceptance decisions. And it feels task appropriate to filter which people I choose to follow based on the context of the service. And that’s how I use foursquare. I have a relatively small set of friends on foursquare and the value of that service does not depend on raw social graph expansion and increasing friend counts. I follow the people I really want to follow and the fact that location is private males it easy for people to curate the network of people they want to know where they are. And it’s one of my favorite apps.

The core Facebook UI is burdened with having to do a lot. It has to be able to show me what my friends are doing and accommodate the myriad sources of information publishing into the system – news articles, status updates, photos, Connect-enabled websites, and (soon) all of the Open Graph activity. As the amount of information streaming into the feed continues to grow, this will not get easier.

Using the core Facebook app on mobile is becoming time-consuming. While I am fairly click tolerant on my laptop, I am impatient when I’m on my mobile devices. It takes too many clicks and too much interaction with navigation elements to get to where I want to be in the core Facebook mobile app. And there are too many distractions – if I want to send messages, I want to get to messaging as quickly as possible. Same with photos. Or games (once they’re available). I don’t actually want to browse my feed, events, etc in that case.

That’s why it took me a while to grasp why Facebook broke Facebook Messenger out as a separate product. I find myself using Messenger a lot more than the core Facbook mobile application. Using Messenger is simply more convenient than navigating through the core app when I just want to send messages. And I find myself using FB messages more and more these days as a way to communicate with people. Having the ability to get in and out of the app quickly is a real plus. I suspect I’ll feel the same way about photos once that app is available too.

Originally, I had suspected that Facebook broke out messenger as a separate product to blunt the growth of the free text messaging products (TextPlus, Pinger, etc.) and mobile group messaging products (Kik, GroupMe, Fast Society, etc). The more I use Messenger, though, the more I believe it’s less reactive and more proactive. I’ll be curious to see how they continue to roll out other discrete apps and how it changes my own usage patterns.

As always, you can leave a comment below or respond on Twitter @chudson.

The “gaming graph” on Android is very fragmented, with lot of gaming graphs and player networks competing for developer attention. There are a handful of “gaming graphs”, or networks of game players that span multiple developers / publishers and have some level of social connectivity. Some of the leaders are OpenFeint, Mobage (from ng:moco / DeNA), Papaya Mobile, Heyzap, and others. Each of the solutions above has its pros and cons, but they’re not interoperable – they are individual networks with varying degrees of scale. As a developer, choosing which of these to integrate can be challenging. And there is always the option of simply building something for your own use.

Without a platform-wide offering from Google, the individual providers will have to continue to battle it out for domination. Hopefully, eventually one (or possibly two) will win and everyone will use that service for social connectivity. But until then, I think things will be messy.

A centralized place where game developers could publish game activity and where consumers could see what the people they care about are playing could help address the “discovery” problem on Android. In a previous blog post, I shared my thoughts on the discovery problem – you can read it here if you’re interested. Despite Facebook’s recent announcement around HTML5 games, I continue to believe that people who like games are more interested in playing games with other game players, regardless of whether they’re friends on some existing social network. People want to connect around games and game content. So having a centralized place where gamers can share what they’re playing, find new games to play, and connect with others interested in games should help everyone in the ecosystem.

In fact, most of the folks who are providing 3rd party social graphs can make the claim that their networks and offerings, at scale, will deliver exactly what’s described above. With enough players and usage, they can deliver on the value proposition above. But unless one of the existing players gets near complete penetration, it will pale in comparison to what could be achieved by having a platform-wide solution.

Two last questions I’ve been thinking about when considering whether Google could really drive this:

1. Would Google’s many Android partners support and help distribute the system? As we’ve seen in a few cases, not all of Google’s partners are on board with every feature or decision they make around Android. Amazon is going to do there own thing with the Kindle Fire, handset partners are adding their own UI elements to standard Android, and carriers are experimenting with their own app stores for distribution. Even if Google could create an awesome product here, I wonder if their partners across the ecosystem would embrace and support it.

2. Relative to all of the things Google wants to do with Android, where does this rank in terms of opportunities? There are a lot of things that Google has already shared about the future of Android. And there are likely tons of things that are under consideration but have not yet launched. Building a Game Center tool is valuable to one specific set of developers with a specific set of needs.

As always, comments are open. If you liked this post, you can follow me on twitter @chudson for more things like this.

The Samsung Chromebook is not a reasonable substitute to a traditional laptop for the majority of people out there. But it is still a great computer if you already love the cloud and have near-constant Internet access.

If you want a more detailed writeup of this transition from someone who has thought about this issue in greater depth than I have, I encourage you to read Louis Gray’s post. Despite this computer having some shortcomings for the average user, I’ve been pleasantly surprised by how usable it is for everyday uses if you have already moved most of your life to the cloud:

There are two real reasons why I don’t think the Chromebook is a true laptop replacement for the average user today:

1. The Samsung Chromebook requires an Internet connection to have value. While I generally work on my MacBook Air with a reliable Internet connection, I am able to interact with a number of my favorite applications without an Internet connection. The key use cases are working on Word, Powerpoint, or Excel documents when I’m not connected to the Internet, editing or creating notes in Evernote, or working on offline email.

The hardest thing to which to adapt is the fact that I basically cannot use the Chromebook without an Internet connection. It’s basically a browser on top of an OS that boots really quickly. We do not yet live in a world of ubiquitous, always-on (and always available) connectivity. As such, I still need my primary computer to be one that works when I don’t have an Internet connection. The base “free” package of 100MB that comes with this Samsung Chromebook is not large enough for me to use this as my only computer in the absence of Wi-Fi.

2.There are good web-native equivalents to the desktop programs that many users use, but not everyone is ready to make that switch.

The biggest surprise I had in using the Samsung Chromebook was how less dependent I have become on desktop applications than I had realized. I thought about all of the core applications that I use and I realized that there are good web-accessible alternatives that have already become core parts of my life:

-Music: Spotify or Rdio for cloud music vs iTunes client music experience
-Video – Netflix, Hulu, or Amazon for video streaming vs iTunes client experience
-Productivity – Google Docs vs Microsoft Office
-Email – Gmail vs Mac Mail, or Outlook or Sparrow
-Instant Messaging – Meebo or Google Talk vs Skype or other desktop IM client

When I first got the device, I thought the lack of desktop applications would be the biggest thing I missed. To be honest, I never really missed the lack of native desktop applications except for in a few specific situations. For example, the process of trying to mark up an agreement on the Chromebook is hard – Google Docs doesn’t support track changes in the same way that desktop versions of Microsoft Word does. And I have a few other gripes about dealing with spreadsheets. But that’s really it. In the grand scheme of things, that’s a pretty narrow set of complaints.

Ironically, the thing I’m finding most vexing about the device is that it’s hard to work with both Google Apps and a standard Gmail account in the same browser instance. That’s a real need for me and it was kind of frustrating to have to switch back and forth.

You can follow me on Twitter @chudson or leave a comment below.

Like a lot of people, I think the daily deals business is fascinating. But I’ve always wondered when we’d start to see location-based deals for both perishable inventory (empty dinner tables, unsold sports tickets, etc) and more traditional deals inventory that we typically see on the top services. I think it makes a ton of sense for Groupon and Living Social to get into “instant” deals that location-based and / or time sensitive. The business of sending out deals once per day by email or tweet puts a ceiling on growth – opening up the channel to location-based deals allows the deal companies to have much more inventory available at any point in time and to have a more persistent relationship with customers.

There’s one problem with realtime deals, though. In order for them to be effective, you need to have access to or be application that people open several times per day. In my opinion, there are likely very few applications that can clear that hurdle.

Right now there is a short list of applications that I believe are both location-aware and opened several times daily by a meaningful number of users. This is not a complete list (I’d welcome additions), but here are the ones that come to mind:

-Google Maps (no question in my mind this one qualifies)
-Twitter (for those who have location-enabled their tweets)
-Facebook (they report tens of millions of DAU for their smartphone apps)
-foursquare (not on the same scale as the applications above, but I suspect they have a meaningful number of DAU)

There must be others, but I can’t think of them at the moment. Maybe some of the news / content apps are location-aware and get a lot of usage, but I’m not sure that they would be ideal for what I’ll describe below. Ditto on the location-aware photo sharing apps. I think the list of apps that fit this funnel is small but I hope others can point to others that fit the bill.

If you’re a daily deals provider interested in an instant deals experience, you have one core question – how do you get people to open your application several times per day? You could obviously try to make your core application more engaging on a daily basis. And, anecdotally, I hear that people redeem a fair number of daily deal coupons using the mobile applications provided by those vendors. But that is a redemption experience, not an engagement experience. I don’t actually think it’s really easy to create an application that people enjoy so much that they want to open it every day and use it as a way to share their location.

As an aside, the reason the several-times-per day application open rate is necessary is that you need to a) have several opportunities to refresh the user’s location and b) you need to have several times to present location or time sensitive deals. The more opens and location shares per day, the more opportunities you have to reach that customer.

So, for anyone looking to experiment with real-time deals, you need a high activity platform. I can imagine it would be hard to partner with Facebook as they have a deals offering of their own. Ditto on Google with Google offers. Hence the opportunity for foursquare – they have have a good audience and are not working (at least as far as I know) on a daily deals platform of their own. So I think they’ll be successful as a key enabler of real-time deals / offers. And they don’t have to sign up / onboard every single local merchant to make this strategy work as they have the scarce commodity of frequent usage among those who use the application.

Thoughts? Leave a comment below. You can also follow me on Twitter on @chudson.