This seems really odd to me. The iPod Touch is kind of like a gateway drug for the iOS experience. Because the Touch doesn’t require a voice or data plan, it’s a device that’s accessible to teens, kids, or anyone else who wants a good iPhone-like experience without the cost of becoming a mobile subscriber. And I believe that those people who own iPod Touch devices are learning about the iOS experience and it’s shaping their expectations for touch-enabled phone experiences an it’s making those people trained in how iOS works. And the Touch allows developers on the iOS platform to reach an even larger pool of users.

If you have any insights into why there isn’t a popular PMP / iPod Touch competitor built on Android and marketed in the US, I’d love to her your thoughts.

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.

If you are going to do a product-oriented tech startup, it really helps to have at least 12 months of financial runway to cover your expenses and some investment in your ideas before you get started.

I have found it odd that of the many startup articles I’ve read, very few seem to hit on this point. It’s kind of an awkward thing to say – it’s not as if you can’t do a startup without 12 months of runway. And to be clear, there are a number of ways to have at least 12 months of runway, including some of the following:

-Savings and liquid investments
-Family wealthy
-Proceeds from previous successful ventures
-A spouse or a partner with a stable job that covers your expenses as a couple
-A low-cost, low-burn lifestyle
-You’re in school and someone else is paying your overhead and expenses

I had to hear the point about 12 months of runway from a few folks before I believed it. I think that I, like many others, had the same core reaction when presented with that piece of advice:

1. My ideas are good – it won’t take me 12 months to find a high quality idea to pursue. I found it hard to believe that it would take 12 months to find a good idea. After all, most people who decide to start companies tend to believe that a) they are above average and b) have the ability to spot really good opportunities. How could it take a whole year to find a good idea? Well, you have to think about the process. I can almost guarantee that your first idea will not be what you end up pursuing. I was told this by numerous folks, didn’t believe it, and it turned out to be true. More importantly, you’ll have many ideas that die at different points. Some will get killed at the concept stage. Some will only get abandoned after you prototype them. Others will make it all of the way to public launch before you decide they’re not worth pursuing. The point is that failure takes time and some of the things you ultimately abandon have to get pretty darned close to being live before you realize they won’t work or you’re not that into them. Even if you can get to a working, interesting product in less than 12 months, budgeting for a year gives you plenty of time to get there.

2. The idea of saving or otherwise acquiring 12 months of personal burn is kind of daunting. When you sit down and budget what you need for a year, the number can be daunting. How do you come up with that kind of cash if you don’t have it? It’s hard. But going through the exercise is really useful. It might turn out that you can only scrape together 6 months of cash. Knowing that is useful – it helps you understand how far you can go and the types of ideas you can pursue before you raise money or seek other types of financing. Whether you need 6, 12, or 18 months of financing, the process of going through a budgeting exercise is really useful and helps sharpen the mind around what you can achieve.

So why does all of this matter? Well, raising money provides you with funds to grow but also comes with a ton of expectations about what you will achieve. A lot of starting up is thrashing about and trying to figure out what it is that you want to build and how you’ll spend money to achieve that goal. Money spent prior to figuring out some sense of product market fit, market size, and growth plan comes at a very high price in normal markets. To the degree that you can figure out the basics on your own (and your co-founders) dime(s), the better the odds that you’ll be able to raise money at a time when you’ve figured out what it is that you’re trying to do and how you’ll spend the money.

I know Yelp is continuing to expand globally, and it couldn’t happen fast enough for my tastes. When I saw TripAdvisor release their Instant Personalization, I thought it might be cool. But it doesn’t solve my problem. Some time you need to see someone else’s solution to really figure out what it is that you’re looking for. I’ve heard some of my friends who travel say that they don’t trust TripAdvisor rankings because they might be written by employees of the places being reviewed, by people who’ve never been to the place in question, or generally don’t feel “real” (whatever that means). I don’t care so much about the trustworthiness of the reviews and reviewers – I care more about relevance and utility. If someone astroturfs a review but it turns out that it’s a place I like, that’s not as bad as a genuine review whose conclusions strike me as odd.

Whenever I’m planning a trip to a new place, I always ask myself the same simple question:

For someone with my tastes and interests, where should I eat and where should I stay when I’m in a new town?

There are a number of reasons why I think the TripAdvisor status quo is ripe for some disruption. I’ll try to summarize them below:

1. My perception of TripAdvisor’s search results is that they are self-reinforcing
On my last trip, I sat next to a couple who described TripAdvisor as “their bible” – they only go to places that are highly rated. So I went to a number of the highest-rated places and they were largely filled with out of town people, many of whom were either clutching guidebooks, printouts of TripAdvisor reviews, or made comments that led me to believe that their decision to show up was influenced by something like TripAdvisor (if not the service itself). I’m sure some of those people will go back home and dutifully review those places. Which will add more reviews to the top places. And thus the cycle continues. I don’t know much about the TripAdvisor ranking algorithm or how it works, but I think most people tend to look for the highest-rated places and start there. If for some reason those places don’t seem interesting or appeal to them, they move on.

There’s nothing wrong with this approach – taking into account the density of reviews and the ratings seems like a rational way to do things. But it does have the overall effect of driving many casual visitors to the same set of places and concentrating reviews in a set of locations that already have lots of reviews.

One small hack I’ve been using to get around this is to just skip most everything on page 1. Those places are probably good, but there are so many other places that could be great, will probably have fewer tourists, and might be more my style. I usually start hunting on page 3 of the results, where the review density is generally lower and then I ask the concierge or some local people if the places that look interesting to me are any good.

One of the things I’ve always really liked about Yelp reviews is that I can generally get a lot of context about the reviewer. Is the person from San Francisco? Have they reviewed other places I like? Do they reference other restaurants in their reviews? Those things are what help me figure out the reviewer’s context, bias, etc for reviews.

2. I can’t make heads or tails of most TripAdvisor reviews once a place has been reviewed about 20-30 times
If you read the reviews of the top places in any given city, you often end up with the same pattern:
1. A bunch of really positive reviews about the place
2. A few people who had wildly different experiences and call the place overrated, terrible, or not worth a visit
3. A bunch of reviews in between that are very measured in tone

That’s simply not useful to me. Yes, you could read through 10-15 reviews to try to get a complete picture of the restaurant or place in question. That’s time consuming. And at the end of the day, you don’t know anything about the people behind those reviews. You don’t know where they like to stay, what their standards are, what they’re accustomed to in terms of service, and what their idiosyncracies are. I bet there’s probably a review buried in there written by someone like you – I challenge you to find it.

There’s another, more subtle problem that I often find with reviews. Many times, people make comments about the quality and price of the food, especially at restaurants. I think it’s fair to say that not everyone has the same idea of what constitues “cheap” or “expensive” or “best meal we had in town” – this can make it extremely difficult to figure out what to expect. Sometimes people will give you clues in their reviews – they’ll say things that tip their hand about what they consider to be fair prices or other places they’ve been that rank highly to them. This drives me nuts. Even services that include some kind of rough price expectation, the actual bill can vary wildly depending on what you order. I have another hack for this. I often tend to look for reviews written by people who travel without children and as a couple, which is a rough proxy for how I often travel. But that takes some detective work on my end to figure that out. It should be easier.

3. Using my social graph is not good enough – I want people with my tastes, not people I know.
While I do put a lot of stock in personal recommendations and referrals when I’m traveling, there’s no guarantee that my friends will have the same travel or lodging tastes that I will. Some are into ultra-deluxe. Others are really into hostels and low-budget accommodations. Ditto on food. Like most people, I’m generally able to filter the appropriateness of a recommendation based on the source.

But that doesn’t work at web scale. There are probably many other people out there with my tastes in dining and lodging who are not inside my social graph. Those are the people who’s opinions and thoughts I’d like to read. As I mentioned above, one of the hardest things to figure out about TripAdvisor is who the person is behind the review. I don’t mean whether they’re a shill or a real person – I mean you don’t know what they consider good, bad, or other.

I haven’t used Hunch, but maybe that’s something that Hunch or a similar service can help deliver.

3. There’s lots of other really good sources of data out there that could be used to help me find similar people.

The reason I’m so excited about this problem is that we now have more data sources that could be used to address this problem. For example, I have almost 2,000 foursquare checkins and a decent number of Facebook checkins too. That tells you a lot about the places I like to go and the intensity with which I like to visit them. Why not use that data (as the corpus grows) as a key input for restaurant or travel recommendations? Look, you know where I like to go and you can find other people who like to go to those places too. It seems like a critical, and previously-unavailable, data source that could be an important foundation for a next-generation service here. I have to believe this is on the roadmaps for foursquare and Facebook

Okay, that’s a lot of stuff to post. Hope you enjoyed it. As always, feel free to leave some comments.

I hope to see you there – it’s our last event of the year.

Social Gaming Summit New York City
Wednesday, December 1, 2010
The New Yorker Hotel, New York, NY
Website: http://chudson.me/SocialGamingNYC (save 15% by using the code CHUDSON)

Jessica Rovello, Arkadium
Manny Anekal, Zynga
Robert Tomkinson, Playfish
Katharine Lewis, Fremantle Media
Davin Miyoshi, GSN
Peter Wexler, TrialPay
Alexey Kostarev, iJet
Varvara Zolotova, Progrestar
Geoff Cook, MyYearbook
Paul Chen, Papaya Mobile
Dan Porter, OMGPOP
Brian Balfour, Viximo
Dennis Ryan, PopCap
Arjun Sethi, LOLapps
Albert Lai, Kontagent
Nima Pourshasb, Live Gamer
Trip Hawkins, Digital Chocolate
Peter Farago, Flurry

-Keynote talk from Kristian Segerstrale, Co-Founder of Playfish
-Keynote talk from Gareth Davis of Facebook
-On-stage interview with Peter Vesterbacka of Rovio, maker or the hit game Angry Birds
-Panel discussion with four of the largest independent social games companies on the future of life for independent developers
-Keynote presentation by Cary Rosenzweig of IMVU
-Presentation by Dennis Ryan of PopCap Games on making the transition from casual to social games

If you’re planning to come, you can save 15% by registering with the code CHUDSON at checkout. More details below – I hope to see you there!

Social Gaming Summit and Virtual Goods Summit Europe
November 11-12, 2010
Chelsea Football Club, London
Register and see the program at http://chudson.me/VirtualGoodsUK

I have lots of problems with scheduling myself. Things have been much better since I got a virtual assistant and had her manage my calendar using a set of rules I’ve come up with that help keep me sane. But for some reason, I’ve had some experiences with Tungle-like services that just feel socially awkward – it’s not really the service’s fault but rather the way in which it’s been presented to me that make me feel, well, weird.

I’ve had a few instances where I was trying to schedule with people and they just pointed me immediately to their Tungle calendars. I could see free / busy and other info, but I didn’t have any context as to the times that would work best, preferred location, or any of the other things you would normally get from dealing with a human assistant or an email back and forth. The net result was (for me) that it didn’t save any time – it took awhile for the person to give me more guidance on their availability and the location of their other meetings. In the end, the “just look at my Tungle and pick a time” approach didn’t save any time.

The other thing that I find kind of socially awkward (and maybe it’s just me) is that there’s something that still feels weird for me to have someone just point me to their calendar and tell me to pick a time. I’m accustomed to being referred to someone’s assistant who can let me know when / where the person can meet. That’s a workflow that feels comfortable. But without any guidance about when and where the person would like to meet, being told to just “look for a time on Tungle” can sort of feel like a brush off.

I do have one friend who I think uses Tungle well. He regularly refers people to check his Tungle, but he always includes some notes to help, such as “if you want to meet in SF, these days are generally good” or “just pick a few times that would work for you and I’ll make one of them work” – it doesn’t make you feel brushed off and it gives you some sense for what to suggest in terms of time.

Overall, I think products like Tungle are great. I still think we are all learning how to use them and introduce them to people in ways that feel comfortable.

Do you have thoughts on what it’s like to set up a meeting with someone without a human really being in the loop? Think I’m being too sensitive? Feel free to share your thoughts in the comments.

Just wanted to do a quick post encouraging those of you who are interested in smartphone games to attend this year’s Smartphone Games Summit on September 24th in San Francisco. We’ve put together an all-star lineup of excellent speakers and panelists who will share their thoughts on what’s happening in the market today.

This year’s event will address a lot of the most interesting questions in the market today, including the rise of Android and what it means for games developers, the future of mobile social networks with the launch of Apple’s GameCenter, and interesting developments in the global market for smartphone games. We have a great list of confirmed speakers, which you can see below.

You can also save 15% by using the code CHUDSON when you register.

* Jason Oberfest, ngmoco
* Chris Williams, Playfirst
* Brian Morrisroe, Booyah
* Andrew Stein, PopCap
* Marc Gumpinger, Scoreloop
* Tracy Chan, ngmoco
* Jason Citron, Aurora Feint
* Si Shen, Papaya Mobile
* Stewart Putney, Moblyng
* Jim Greer, Kongregate
* David Helgason, Unity 3D
* Charles Ju, Playmesh
* Michael Chow, Newtoy
* Tomoko Namba, DeNa
* Akira Abe, Mixi
* David DC Collier, Pikkle
* Andrew Lacy, Tapulous
* Lee Linden, Tapjoy
* Hill Ferguson, Zong
* Ron Hirson, BOKU
* Michael Chang, Greystripe
* Aunkur Arya, Google