Charles Hudson's Weblog

I received a free Samsung Chromebook after attending Google I/O this year and I’ve been trying to use it as my primary weekend computer for the past few weeks. I have a handful of observations about my experience. I’ll sum my thoughts up in a simple sentence:

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.

Disclosure: Through my work at SoftTech VC we have a small position in Groupon, I have friends involved with LivingSocial, and friends at foursquare (and I am an active user). This post is based on my views alone and doesn’t include anything other than idle speculation or reasoning on my part.

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.

I’ve been really curious about TaskRabbit ever since I heard about the service. While it has always sounded interesting in practice, I’ve struggled to find a good personal use case for the service. Like a lot of people, I’m busy and have a lot to do. But the idea of trusting tasks I need to do strangers makes me nervous. I try to think about the tasks I need to get done along three dimensions:

1. Is this something that has to get done?
2. Do I need to do it myself or would I trust a stranger to do it for me?
3. Would I be willing to pay someone else to do it for me?

The reason I’ve struggled to get my head around TaskRabbit is that I’ve been searching for a task that sits at the intersection of those three circles. I need something that needs to get done, where I would trust a stranger to do it for me, and where I’m willing to pay. I’ve considered a bunch of tasks, all of which have failed in the past. Below are a few examples

1. Pick up the dry cleaning (or other thing) – While this has to be done and I’d be willing to pay a nominal fee to have someone do it for me, I’m not sure I’d want a stranger picking up my dry cleaning even if it’s someone who has been verified by a 3rd party. Maybe that’s just me, but it’s how I feeel.

2. Wash my car – Definitely willing to pay to have the car washed and would be happy to have someone do it for me. But the person would have to come to my place and wash it for me – no way I’m handing over my car keys to a stranger to have them wash it and trust it. Perhaps that irrational – I have had parking attendants park the car for me without a second thought. But in those cases there is some company standing behind the individual who will make me whole if the valet runs off with my car.

3. Water my plants or fold my laundry – I have a class of household tasks I’d like done and would be willing to pay to have done, but they don’t pass the stranger-in-my-house test either.

As you have probably noticed, my big issue with TaskRabbit and similar services has always been my reluctance to trust personal tasks to strangers who are, from my point of view, independent contractors about whom I know very little and who are not backstopped by a trusted brand or service. While I’m happy to trade money for time in some circumstances, I need to know that there is someone standing behind the service who will make me whole if this “trusted stranger” doesn’t do right by me.

Well, I finally had a good task worth doing. I moved into a new place in San Francisco and had some IKEA furniture that required assembly. My guess is that it would have taken me about 5 hours to do it myself. I called the independent contractor that IKEA recommended and got a quote. They gave me a price of X and told me it would take about a week before they could come out to do the work. I posted the task on TaskRabbit and I received a price quote of about 75% of what the IKEA-referred contractor had offered and the gentleman was able to come over the next day. The whole thing was set up in less than an hour after I posted.

When it was time to do the work, they showed up on time (I was late). I let them into my place and just told them to call me when they were done. I got over my trust issue because it was a new place and there really wasn’t anything in the place – just some unassembled furniture. The team assembled my furniture, cleaned up well, and locked the door. And I was able to pay by credit card when the work was done. Overall, it was a really clean and simple experience and it has made me think more broadly about what tasks I could have done by the service.

In the end, I was really impressed with my first experience using TaskRabbit from booking to completion. And it’s clear to me that building a strong brand around the trustworthiness of their independent contractors is going to be key to their growth with customers like me who are slightly cautious. That’s going to take time, but it’s a big prize if they can win it.

After reading a few blog posts, like this one on GigaOm about how difficult the Amazon Appstore has been for developers who have paid applications, I wanted to share a few thoughts I had about why Amazon could eventually become a big distribution source for freemium Android games. In the name of full disclosure, Bionic Panda Games (where I work) did launch on the Amazon Appstore and did encounter a few of the vexing issues that were identified in the article. It’s not perfect yet, but I do see a pretty clear path toward relevance.

I think you need three things to really succeed as an app store, based on what we’ve seen from Apple and Google. And to be clear, success means that you as the app store make money and can drive enough distribution to developers that they too can build a big business on the back of your audience.

Payment-enabled customers + device footprint + well-merchandised store experience = Potential to Win as an App Store

1. Payment-Enabled Customers
One of the (many) things that makes the Apple iOS ecosystem so powerful is that Apple has 200 million hard-won credit cards on file. Having had iTunes prior to the app ecosystem meant that they were able to tap into a large audience of users for whom purchasing apps and in-game items is as simple as a single click.

Perhaps the only company more synonymous with one-click purchase experiences than Apple is Amazon – they did for the web what Apple has done for the iOS ecosystem when it comes to ease of transaction. And Amazon has tens of millions of payment-enabled customers by their own admission. I’m not sure why they haven’t gone through the process of making it easier for freemium game developers to integrate some variant of Amazon Flexible Payments Services as a way to charge for in-app purchases. That seems like a no-brainer way to enable freemium game developers to make real revenue through the Amazon Appstore.

2. Amazon’s Distribution Strategy for the Amazon Appstore
I think Amazon has a pretty clear strategy for how they will get their own Appstore deployed to tens of millions of consumers. This is all my speculation – but I think it makes sense:

Phase I: Give away top-tier games that are usually paid for free in order to get consumers to download and install the Amazon Appstore. This is just a simple quid pro quo. The goal is to give customers something of value (a free or greatly reduced install of a game they covet) in exchange for downloading and using the Amazon Appstore on their Android device. Provided Amazon can continue to find developers who want the exposure for their content, this strategy should help seed things.

Phase 2: Work with carriers to get preload deals so that the Amazon Appstore is on many more devices. Doing preload deals is nothing new. If you have relationships with carriers and can afford the economics required to make those deals interesting to them, that’s one way to get the Amazon Appstore in front of more consumers. This might prove to be trickier than it sounds, given that many carriers and handset makers themselves also have designs of building their own app stores. But this is still a strategy worth pursuing.

Phase 3: Launch an Amazon tablet, powered by Android, with the Amazon Appstore front and center as the primary application discovery method. The last thing Amazon can and should do (and is doing) is to build and sell its own Android tablets. This has less to do with games and more to do with the Kindle business. It’s a good hedge in the whole e-reader vs table debate and should allow Amazon to have a larger footprint for its cloud music and cloud video services. I would fully expect that Amazon will integrate its own Android market front-and-center on that product and will put its considerable marketing muscle behind promoting its table to both Kindle users and people who have yet to have settled on a tablet device.

3. Well-merchandised store
No need to belabor this one. Amazon is one of the world’s premier merchandisers when it comes to selling things online. I’d like to think they could bring some creative muscle to app discovery and recommendation.

It’s clear to me that Amazon is still in the early stages of building out their Amazon Appstore and that to count them out based on their current progress seems premature.

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In my dual roles as a Venture Partner at SoftTech VC and Co-Founder of Bionic Panda Games, I’ve met with a bunch of companies and teams who are focusing on trying to solve the problem of mobile application discovery. Simply put, the problem (as articulated by people trying to solve it) is that there are many more interesting applications out there than the typical consumer can find on his or her own. If you look at the number of apps in the Apple or Android markets, that’s probably true – no consumer can be fully aware of everything out there that could be of interest.

By and large, the teams I’ve met are incredibly smart, clever teams of people who I think will impact the world of mobile applications in positive ways. But after having met with a handful of really great folks working in this space, I’m becoming convinced that application discovery is a bigger problem for those applications looking to get discovered than it is for consumers looking for useful or entertaining applications. Three things I’d like to throw out there for discussion:

1. There is a lot of mobile application discovery that happens face-to-face in the real world and will probably never show up in your application analytics system. If you’ve gone out in a major city lately, I’m sure you’ve seen this happen. Someone pulls out a phone and shows off an application. Someone else at the table says, “Wow, that’s a cool application – I’m going to get it right now.” And that person starts downloading the application. That’s the beauty of the the combination of app stores, smartphones, and reasonably good data connections – if you find a new application you want, you can get it nearly instantly. No more waiting until you get home to have a friend invite you or send you an email. Just grab the app in context and grow. I’m not sure that there’s an opportunity for an app to help facilitate that face-to-face communication.

To most analytics systems, these installs will look largely organic (someone just installed your app and it didn’t come from a trackable link of any sort) even though they aren’t. And, as a developer, it’s kind of hard to know how often this is happening for any given application. It should go without saying, but I’ll say it anyway – lots of people will instantly install applications that their friends are using when this discovery happens face-to-face as your friend can often tell you (in his or her own words) why he or she likes the application and how he or she uses it. That counts for a lot for most people.

2. Most consumers are not actively looking for new applications to download, but will download them in order to get something else or based on the recommendation of a friend. I just don’t think most people sit around thinking about applications to discover. Most people are busy doing other things – reading, playing with the applications they already have, chatting with friends, etc. However, as I mentioned above, I do think that there is value in knowing what applications your social graph is using. For example, if you’re trying to make a decision on installing an app with strong network effects (any social networking or communications application, for example), knowing what your friends use has real value. For example, if most of your friends have standardized on using a particular location-sharing, photo-sharing, social networking, or other social application, knowing that can and probably should influence your choice of application to use.

The other use case is the incentivized install use case. If people are using an application and can get a reward in that application for downloading or installing someone else’s application, it shouldn’t be surprising that they are willing to do so – installing an application doesn’t really cost most users anything (other than the space on the device and the time required to install it) and the act of installing an application is a known behavior.

3. Open question – will consumers fire up an application to help them find other applications? One question I have is around how application discovery is delivered as a product. A number of the products in the space today involve opening or installing an application in order to discover additional applications to use. I am not sure this is the model that consumers want, but it’s still too early to tell.

Despite everything I’ve said above, application discovery is a problem for application developers. It’s really just a subset of the marketing challenge we all face in standing out in a sea of tens of thousands of applications that exist in app stores – being discovered is a good way to grow an application and absolutely essential in the growth plans of many companies.

As always, comments are welcome. And if you like this you can always follow me on Twitter.

I’ve been tracking the progress of Google’s In-App Purchases for awhile. It’s not just academic to me – we’re building Android games over at Bionic Panda Games and the development of that product is pretty important to us. Previously, I worked on the Facebook Platform, which went through its own process in launching Facebook Credits. In watching how Apple, Facebook, and now Google roll out payments on their own platforms, I have a few thoughts and observations to share. In watching these platforms all roll out their own solutions, there are three things I’ve noticed.

Before I jump into the three observations, I think most developers want the same thing from any payment provider. First, you want payment enabled customers – you need to have people who have the capacity and ability to pay. Apple solves that – they have nearly 200 million credit cards on file. Facebook is working to solve that by nudging customers to sign up for Facebook Credits. Mobile providers like Zong, Boku, and BillToMobile solve this by enabling anyone with a mobile phone to use that as a billable identity. PayPal has a ton of payment enabled accounts as well – you get the idea. Second, developers really want to either have a standard, low friction UI (a la iTunes) or the ability to control the payments flow and UI themselves to optimize for conversion. It’s a pretty simple formula – payment enabled customers + low friction UI generally leads to good monetization opportunities.

Now, on to the observations about what happens with platform payments:

1. If you are on a platform provider’s network and they offer a payments, you should assume you will (eventually) have to use their solution. Most payments business require scale to work – it’s generally all about taking a small portion of a large amount of money flowing through the system. And most networks or platforms can only support a small (often) one payments solution at the scale required to make it an interesting business. Whether the payment provider wants to actually be the payment solution or control the payments / wallet experience, it’s generally safe to assume that most platform providers will ultimately want to plug into the money flowing through their platforms.

2. Platforms that let alternative monetization providers on their platform early lose the opportunity to set the rules of the road early. Platforms that attract developers or court them need to have a story on monetization early. In the event that platform providers don’t have a solution, most developers will end up doing something in order to generate revenue. Those publisher / developer chosen solutions might not be in line with what the platform owner would like to see happen. But in the absence of a platform-approved solution, most developers will find some way to make money because they need to do so to stay in business. Convincing (as opposed to requiring) developers to take out things that are making them money can be hard – once those solutions are in they’re sticky.

3. Allowing other payment solutions providers on your platform creates a reference point for developers – this matters when the platform provider’s payment solution comes out. Related to the point above, one of the challenges with launching platform payments after you’ve allowed “rogue” solutions on your platform is that developers already have some sense for how well they are doing with their own solution in terms of total revenue, conversion ratio, and fees paid to their payment provider. This generally changes the nature of the conversation. The conversation inevitably comes down to a conversation about whether the platform’s payment solution will be as good, as cheap, and as effective as what developers are already doing. And that can be an awkward conversation.

At the end of the day, platform owners can do whatever they want with their platforms when it comes to payments. They can mandate or bar usage of certain payment types. They can set their own rates and terms. But I think the cases of Apple and Facebook are interesting as it relates to Google:

Apple – I give Apple a lot of credit for being pretty smart with in-app purchases on iOS. They gave developers a fair warning that they wouldn’t really tolerate alternatives, announced that in-app purchases were coming in 3.x, and then they actually delivered the solution shortly after. That seems pretty fair to me – give developers a working and workable solution on a fairly fast timeline. Having 100-200 million credit cards on file and a super simple UI / UX is a strong offering for developers. That’s part of the reason why it’s working.

Facebook – Facebook took a pretty different approach. They let a lot of other payment options onto the Facebook platform from day one. Gradually they started restricting how developers could monetize with both payments and advertising solutions, culminating in the announcement that Facebook Credits would be mandatory in June 2011. Given the 30% take for Facebook, not all of the developers on the platform are happy about moving to Credits. But for Facebook, it was okay to wait – developers were clearly making money on virtual goods and Facebook had established itself as the only major social network with the scale opportunity of interest to developers interested in building large businesses. So complain as they might, there aren’t a lot of obvious viable alternatives for developers looking to build social games on top of existing graphs. As Facebook Credits roll out and are adopted more broadly by both consumers and developers, reluctant developers might have a change of heart and really both embrace Facebook Credits and see some real benefits from making the switch.

I think it will be really interesting to see how Google progresses. On the one hand, it’s early enough in the life of the Android market that they could move more like Apple and clamp down and stamp out anyone who’s attempting to use anything other than their own in-app billing system. That would be easy to do if there is a good enough UI / UX experience and enough credit cards / payment-enabled users on the Checkout system to make it a seamless experience for the average user. But I’m not sure that’s the current state of the market. Kim-Mai Cutler at Inside Network did have an interesting piece on the current state of affairs – read it here if you haven’t already. At the same time, the risk of waiting and taking the Facebook approach is that the payments ecosystem on Android could get out of hand and it will be hard to get the genie back in the bottle. Unlike Facebook, Google does face a very strong competitor in Apple – if developers are unhappy with Android, developing for iOS is a financially viable alternative.

As always, comments are welcome.

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I have been trying to wrap my head around the New York Times new digital subscriber plans. I have been happily paying for the NYT on my Kindle as well as reading it for free from time to time on my iPad(s) and mobile phones. I just don’t get their new pricing scheme. It’s not my place to say what the New York Times should charge – they should figure out what the market will bear. And I am already perfectly willing to pay for their content as I enjoy reading it. The thing I don’t understand is why they want to charge such an aggressive price for me to add a third screen. A few observations and questions:

1. What percentage of people who have iPads / tablets and want to read the New York Times on those devices also own smartphones? My guess is that there is significant overlap between iPad / tablet owners and smartphone owners. Why penalize that audience to the tune of $180 per year for the right to consume the content on two additional devices? It basically doubles the price of the annual subscription on a single device.

2. While I’m willing to pay a bit extra to be able to read the NYT on the tablet and a second device, I’m not willing to pay over $400 a year to read it on my tablet and my iPhone / Android device. That just seems outrageous. If the price increment were on the order of $5 per month, I’d probably opt for the full plan that includes tablet and smartphone access. Paying a small amount for an incremental device makes sense. Paying almost double does not.

The thing is, I don’t actually object to being charged more to read the NYT on multiple screens. But I think of the world in a really simple way – there’s my computer (my Macbook Air) and then there are my smart mobile devices (iPad, Android phone, and iPhone). It feels to me like splitting the tablet and smartphone experiences into two different plans doesn’t match my usage patters. I’m either on my computer or I’m on the go – I’m happy to pay for convenience, but this plan doesn’t nail it for me.

I hope the New York Times reconsiders and drops the price on the “all-in” plan – I’d happily pay for the peace of mind knowing that I can consume everything across all the devices I use for a price I can swallow. Until then, I’m sticking with the iPad plan and I’ll have to just make do on my smartphones.

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I spend a large chunk of my day on my phone and away from my computer, running to and from meetings or pacing around the office. I also travel a lot, so I try to make sure I have a set of mobile communications tools I can use to stay on top of everything. Aside from email on my smartphone, there are three major tools I use today and I’ve been trying to get a handle on how I might want to use Beluga. Kim-Mai Cutler from Inside Mobile Apps has a great summary post on Beluga and it’s recent growth.

I think the Beluga app is beautiful and well done, but I can’t seem to figure out where it fits into my mobile needs. Below are the core mobile tools that I use – if you’re a Beluga user and have some good use cases, do let me know:

Mobile IM (Meebo) – I use Meebo for mobile IM. Mobile IM fills an important gap in my communications life – it gives me the flexibility to extend a service I already use heavily (desktop IM) while on the go and makes use of the buddy lists I’ve already created. And it works on Android and iOS, which is key for me.

Text Messaging – Text is my mobile-only channel of choice. It comes right to my phone. It’s fast. And it’s high-quality signal as I only hear from people who have my phone number. Pretty clear and strong use case for being able to message on the go with text messaging.

Situational Group Texting (GroupMe, Fast Society) – I also get the use case for GroupMe and Fast Society. I travel a decent amount and also have groups of people with with whom I want to communicate for brief periods of time. For example, I’m planning to use one of these services when I’m down in Austin for SXSW to keep up with a group of guys I know. I’ve also used both services for weekend trips with friends where everyone wants to keep in touch and allow everyone to see the what’s going on. These aren’t services that I need to use every day, but they do serve an important purpose.

Overall, I feel like my mobile messaging needs are being pretty well met. I’m not sure where Beluga should fit in my mobile messaging needs, but I also didn’t see how GroupMe and Fast Society would fit either until I had that ah-ha moment.

I’ve been chatting with a lot of people who are working on mobile games with a strong location component. Almost all of them are trying to do some mashup of a game plus check-in data to do something interesting. At its core, the concept sounds intriguing. To date, I don’t think anyone has really cracked the market for true games with a strong location component. I am explicitly excluding foursquare from this analysis as I think they’ve de-emphasized the game elements of the service of late and focused more on the community elements (out with leaderboards and an emphasis on points, in with comments and photos – that’s a subject for a post of its own).

If you stop and think about it, building a mobile game that is heavily reliant on people checking in is a tough challenge. I don’t have access to anyone’s proprietary data, but my hypothesis is that there are millions of people ACTIVELY checking in on a regular basis and tens of millions of people playing games on mobile devices. Games that focus on check-ins as a core activity are up against a core challenge in that there are 10x (roughly) as many people playing games as there are checking in.

I want to be really clear about what I mean by ACTIVELY checking in. People who ACTIVELY check-in are those who do check-ins of their own on at least a monthly basis. The one thing I want to make sure I highlight is that I am certain Facebook Places has many more people who have checked-in than foursquare simply because 1 person on Facebook can check-in multiple people. So it’s entirely possible that there are people who have been checked in on Facebook Places who are not themselves active users of check-in products. So I think you need to apply some discount to the FB Places check-ins if you’re trying to figure out how large the active audience of checking-in people is.

Whenever I look at this stylized image, it’s clear to me that trying to get location-based games to work for a large audience, relying on check-ins won’t work today. There simply aren’t enough people engaging in check-ins today to build a game based solely on that mechanic as you’ll only get the overlap of people who like games and actively check-in.

What will work? I have no idea. There are lots of smart people working on this. But I am a bit skeptical as to whether or not a check-in centric location based game can get really big today. Check-ins are the future, but location based game developers need a solution today.