dangerouslyawesome

This is not fatblogging, I swear.

The last 3 years have been good to me in a lot of ways, but I have’t been good at taking care of myself. Among my 2010 promises that I made (not so much a resolution, but really a promise) was to take some time to refocus on me.

So far, 2010 has been the year that I wanted it to be. Indy Hall has continued to grow, but also mature. As such, I’ve been able to focus on some other ventures that are fulfilling in many new ways.  I’m focused on products again, building both technologies and businesses. I’ve focused on teaching. I’ve focused on writing.

I’ve focused on my mental health. Learned what I cared about. Who I cared about.

I’ve taken time for myself.

I’m relatively healthy considering my aversion towards doctors. I only really get sick once, maybe twice a year.

But my body health – my physical fitness – has deteriorated. Recently, I dared to step onto a scale, to find that I weighed nearly 20 lbs more than the last time I was unhappy with my weight. So with 5 months left in 2010, I’ve committed to getting back under 200 lbs.

Last Monday was the “Geek Fitness” edition of Refresh Philly. I hadn’t been to a Refresh in some time, and this seemed like a topic I should pay some attention to.

I left Refresh with some new perspective on how – and why – I could make this happen. Here’s what I’m up to one week later:

Lose It or Lose It

I don’t think I’ve ever shouted from the hilltops how awesome Randy Schmidt is, which is a damn shame. I’ve actually known Randy since college, though we didn’t really get to know each other until the early Indy Hall days. Apart from being one of Indy Hall’s longest standing members (Randy’s participation and support dates back to the “Cream Cheese Sessions” of 2007), but he’s also one of my favorite success stories of complete career reorientation within the Indy Hall community.

But that story’s for another day.

Randy’s a problem solver. Lose It or Lose It was his solution to his own problem – his inability to stay motivated through losing weight. He found a pretty fascinating combination of reminders and the association of money to goals that’s not purely incentive based. Quickly, here’s how it works.

1. You choose a 10 week plan – 1, 2, or 3 lbs per week
2. You pony up an uncomfortable amount of your own money
3. Lose It or Lose It combines accountability friends, daily SMS or email reminders to you and your accountability friends), and weekly required weigh-ins to keep you on track
4. Each week you’re required to weigh in on the same day. Each time you miss your weigh in for any reason, you lose 10% of the money you put up at the beginning. If you weigh in but miss your weight goal, you lose 5%. If you weigh in successfully, you lose nothing!
5. At the end of 10 weeks, any money not lost in the weekly weigh-ins is returned, in full, including the paypal transaction fees.

There’s some neat things working here:

A set schedule with an attainable goal

When I business coach, one of the most common lessons I teach is to set realistic goals. There’s more value in setting goals that you can achieve than just achieving them, there’s also the emotional momentum of successfully achieving a goal. LIOLI gives you a reasonable schedule with a fixed end point, along with a realistic goal – just a couple of pounds per week – to set help you up for successive wins and keep you motivated.

Accountability

Randy’s Refresh presentation was actually more about how LIOLI takes on the human accountability factor that normally undermines diet partners. Unlike the person you’ve asked to keep you on track, the website is relentless and uncaring. Mostly because it, itself, isn’t trying to lose weight. But rather than remove the human element COMPLETELY, it stacks the automated (but friendly and often funny) reminders up against those human accountability friends as well…in fact it urges them to keep you on track. That’s right, your friend gets reminders to remind you to keep working at your goal.

Meta.

Money

I waited a long time to sign up for LIOLI because I had basically convinced myself that I’m not motivated by money. Then, after hearing Randy talk about it, I realized that LIOLI doesn’t motivate you with money, it helps you use your own money as a bargaining chip. That is, when you’re bargaining with yourself.

The trick to LIOLI is to put up an uncomfortable amount of money. Not an amount of money that risks you losing your home, or putting your life at risk. But an amount that you’d certainly prefer not to part with. And what you really need to consider is that the total amount isn’t the important part – but instead, the 5-10% amounts you risk to lose each week.

Basically, each week becomes it’s own mini-game. The amount at risk each week needs to be enough to force you to think, “is this decision, which is likely to hurt my chances of weighing in at my goal, worth $x?”

So I put up $1000 to lose 2lbs per week, or 20 lbs. That made each week worth $100, and each time I slipped on my weigh in target, I had $50 at stake. That’s enough to make me think “that burger’s not worth $50″. Or “I don’t need to spend $50 to have another beer”. Or “I could skip my run/ride, but that could cost me $50″.

I’m lucky to be at a point in my life and career where $50 isn’t going to break me, but its still enough money to make me associate my decisions with a value. If the outcome of decision doesn’t match the value, it’s an easy decision to make.

I’m not winning $1000 at the end of my 10 weeks. I’m using money as a bargaining tool with myself to help me make better decisions. It was my money to begin with, after all.

So, does it work?

Well, over 1000 lbs have been lost by LIOLI users. Almost 70 of those lbs were Randy’s. And by years end, I’m hoping that at least 40 more will be mine. I’m already ahead of schedule, but they say the first few weeks are the easiest.

Eating Better

I’m stating the obvious, but it’s not really something I’ve ever made a conscious effort to do. Luckily, it is an easy change, because based on the fact that I eat out almost every meal, all I needed to do was remove a few things completely from my eating options and add a few new ones.

I’m using an iPhone app called Lose It to enter my exercise and estimate my calorie intake. Not knowing how poorly I ate before makes measuring the differential tough, but simply paying attention to what I’m eating is already making a huge difference. If something I’m thinking about eating is worse for me than I realized, I go into the self-negotiating mode for LIOLI. That’s not to say I can’t eat anything I want, but I know what the outcome could be based on my decision.

A trip to the farmers market on Sunday to pick up some fruit for snacks, and another trip to Whole Foods for some easy-prep meals that aren’t full of crap means I can still eat well without sacrificing too much convenience, simply by knowing that my options are better than the ones I was giving myself before.

Much like LIOLI’s weekly required checkpoints, using Lose It on my iPhone is helping me learn my eating patterns so I can make smarter decisions about what and where I eat.

Exercise

Honestly, I’ve never been one to exercise. It’s never appealed to me. Getting sweaty, grunting, being in pain? Lame. I’m also not motivated by team sports, so I’ve never been much of an athlete. So something had to change.

Knowing full well that diet changes alone weren’t going to lose me 2 lbs a week, I picked a few variations to compile an exercise routine that I could manage to keep up with.

C25k

I was honestly motivated by the Refresh talks about running, so much that I convinced myself that I could do it too! Unfortunately I was quickly reminded how hard it is on my flat feet, and that it probably wasn’t the most sustainable way for me to maintain a daily workout schedule. That said, I found the Couch to 5k program approachable, and something I’m still going to try to work through.

I’m not really interested in actually running the 5k, but I like the program from the perspective that it assumes that I’ve never run before, and starts there. The first weeks runs are actually over 50% walking. But I’m still out for 30+ minutes, sweating, and “feeling the burn”. The part that sucks is later in the day when my ankles are wobbly and sore. If I can’t recover by the next time I’m planning on running, I’ve undermined my whole plan.

There’s a sweet C25k iPhone app, though, that gives you audio cues when to switch your running and walking, and it even lets you play iTunes or Pandora in the background. If you ARE a runner and want to train up to a 5k (or a 10k), there’s an app for that (10k version).

15 miles to 30 Rock

Since running isn’t a daily option (and I decided to start this whole routine in August of one of the hottest summers in Philadelphia’s recorded history), I’ve decided that going to the gym and using some cardio equipment is completely acceptable.

Treadmills give me the same problems as running outside, except it’s boring. So I took a spin on one of the stationary bikes. A few things I really like about the bike:

1. I’m not on my feet. My arches thank me.
2. Milage motivation – being able to ride 15 miles in the same amount of time I can barely run 2 miles is just more motivating to me.
3. I don’t feel the need to stop. Unlike running, where I need to stop because my ankles hurt, I can power through a consistent 40 minute ride even up the virtual “hills” the training program provides.
4. I can watch 30 Rock

That last one’s a little weird, but I was reading about workout routines and saw someone who stopped letting themselves watch certain shows except for when they were working out. Earlier this summer I decided to catch up on 30 Rock, which I’d never seen but heard was really funny. Season 1 had me hooked.

Before I could buy Season 2, Hulu sent me an invite for Hulu Plus. This gave me full access to their catalogue (which happens to include all seasons of 30 rock), but it also lets me watch them on my iPhone/iPad.

So I promised myself that I’d get through 30 rock, 2 episodes at a time, but ONLY while I’m on an exercise bike.

Those 40 minutes whiz by. It’s like taking a 10-15 mile bike ride with Tina Fey and Alec Baldwin every morning. It’s awesome.

And when I’m done with 30 Rock, I can pick another series I’ve been meaning to catch up on…I can even up the ante to 30 minute shows, and documentaries. Who said exercise equipment had to be boring!!

P.S. The music they play at my Gym is so bad. SO bad.

Daily Mile

A social network for working out. Not only did it seem counter-intuitive (social networks are places to sink time sitting on your duff, not being active), but it sounded awful. I imagined a virtual locker room full of athletes, slapping each others’ asses and shouting lame motivational chants at each other.

But Daily Mile turned out to be something else altogether. In fact, its kinda like having workout buddies without having to smell them. You can pick up tips (and even exercise routes) from other people that live near you. The amazing part to me was how many people I knew who were already on it. People I knew from Indy Hall, or just the general geek scene in Philly. I was welcomed warmly as I began to log my workout progress. In just a week, seeing miles rack up from runs and rides is pretty cool. I’ve embedded a Daily Mile widget in my blog sidebar too, more for tracking those miles than anything else.

Other relative stats, like “donuts burned” and “times around the world” are pretty exciting…while the numbers are low now they are the ones I’m kinda excited to see climb.

I won’t be consistently blogging about my progress, though I will be keeping all of my records public on Lose It or Lose It and Daily Mile, etc.

Thanks to all of my friends, especially Roz Duffy and Randy Schmidt, for the encouragement, support, and inspiration to cap off my year of refocusing on me in a really important and positive way.

One of the guys I work with, Jon, just bought his dad an iPad. His dad isn’t tech savvy, to the point that he didn’t use his home computer much any more, so when he asked for an iPad his son was perplexed but excited.

Jon shared an email with me that his dad sent him after spending about 20 minutes with the iPad. I was amazed at some of the comments enough that I had to jot them down, and some of the ideas and questions they raised.

Dadquote #1: I assume APPS, means applications.   Never seen it explained anywhere.

The concept of “Apps” seems very easily adopted. I wonder why that is?

Dadquote #2: Did not see where you get into the web

The mail app is called “Mail”. The Photo app is called “Photos”. The Calendar app is called “Calendar”. Etc.

In comparison, “Safari” is only relatively obvious to a Mac user as a web browser, or “The Internet” as my mom calls it. Why wouldn’t Apple call their internet app “Internet”?

Dadquote #3: as not sure how to shut it off…just turn it off with the same button at the top that I used to turn it on…wasn’t sure if there was a certain procedure to get out of things so I don’t lock things up.

Ah, the mark of a PC user. “I have to turn this thing off a certain way or else it breaks” is something that I don’t miss from my days of building and repairing PCs. I thought it was particularly interesting that he actually intuited the correct answer, and then based on past experiences, thought to himself, “no, there must be a harder procedure I have to go through to do it right”.

Dadquote #4: Once I have it in front of me other things may come to me.

He’s already committed to exploring the product more, one of the greatest achievements that I think any product designer can aspire to. The difference between that and the alternative approach to new technology – being afraid or intimidated, or worse, frustrated – is remarkable.

If the thing you’re making is ever meant to be used by anybody but you, there are some great lessons in these dadquotes that I’d encourage you to consider.

I’m a heavy Gmail user, with 6 (soon to be 7) separate Gmail and Google Apps accounts. On my Macbook, I actually IMAP in to all of the business accounts using Mail.app for one reason: cross-account search. For my personal account, though, I’m extremely reliant on Gmail’s web interface. I’ve used Mailplane in the past, and really loved it…with the exception of the inability to do cross-domain search. I use that daily.

On the mobile, there’s no option for cross-account searching. Mobile Mail.app gives me some native functionality and speed, but without cross-account searching, I’d much prefer to use Gmail’s mobile web app. HTML5 support in recent releases has made it faster, easier to use, and hands down one of the best mobile apps on the internet. I used Mobile Mail to connect to my Gmail accounts over IMAP because having multiple bookmarks was clunky no matter how I configured it, but I was always looking for something better.

In all cases I use IMAP because it keeps accounts in sync; changes made on the computer, the web, and the iPhone are all synchronized via IMAP.

I never used Push for my email because, well, I get a lot of it. I rely on Push for contact and calendar updates, but for email…if I haven’t checked my mail in 10 minutes, I can be sure that there’s something new in there.

Worse are unread counts. I’m compulsive about unread accounts. Mail, RSS feeds, Campfire, whatever it is…I hate having things unread. It’s a bad behavior, because I treat unread counts like to-dos, and in all of the scenarios where unread counts keep me on my toes, they are essentially to-do lists that OTHER people can put things on to. I’m already busy, I don’t need someone else to put more things on my to-do list.

The biggest loss in using Mobile Mail.app is tags, something that I do use pretty extensively. I’ve learned to get around it in Mail.app, which has better drag and drop support for moving things into folders that represent tags over IMAP. Mobile Mail.app was just clunky, and I resolved to not do that interaction on the go unless I had to.

I know I’m not describing everyone, but I am describing a lot of people. And as more corporations move their mail infrastructures away from Exchange and into Hosted Google Apps accounts, the group with this set of needs grows more and more.

A few weeks back, Dave Martorana (of MultiFirefox, Multiplex, and Two Guys on Beer fame) slung me a prototype of an app he’d been working on at IndyHall. It was called “MultiG”, and was basically an app that did fast account switching between Gmail and Google Apps Gmail accounts. It was rudimentary, but instantly useful for me. He quickly added an “unread” count to the accounts dashboard, but then did something I had never seen in an email client. He added a secondary badge that showed how many messages were actually new. I mean, how many of your unread messages weren’t there the last time you looked.

Think about that for a second. The anxiety of unread counts has finally found its Prozac.  All I care about is how many messages are new! In casual conversation, I dubbed this feature “TrueNew”, something that I hope other developers build into their app notifications.

At this point, I was hooked. But Dave wasn’t done.

He’d also whipped up integration with the iPhone’s native address book. I haven’t gone through the process of moving my address book into Google, and again, I have multiple accounts so where would I sync my address book to? Not all of them.

Dave added a button to the chrome of the Gmail browser window in his app that let me pull up my iPhone address book and insert email addresses right into the “To:” field. Sneakily, if I turned on CC or BCC, the exact same feature gave me the choice of which field to put the address in to. Simple, sleek, lovely.

Since emails tend to include attachments and links, Dave also put in a handler that made sure that they opened without leaving the app, much like our favorite iPhone Twitter client, Tweetie.

This feature set changed the way I interacted with mail on my iPhone. It made my life better. It made one of the most painful parts of my day, dealing with email, less painful.

We realized that “MultiG” was a lousy name, and Johnny Bilotta (the other Guy on Beer) proposed “Mailroom”.

Sold.

He whipped up a sexy icon, and we were off to the races.

Dave got the app in the hands of a few other testers, worked out some kinks, processed some feedback, and with the hand of myself and co-conspirator Amy Hoy pushing him to “ship as early as possible”, got it into the App Store.

Initial feedback was mixed. People who were like me in terms of email use loved it. People who had different email workflows weren’t as convinced, and many people saw it simply as a “wrapper for Gmail”.

Technically they were right, but they were missing the progressive enhancements because they didn’t augment their workflow. The app wasn’t for everybody, and we knew that. We’d still struck a chord with a good number of our initial users, and got some great feature requests.

2 weeks later, Dave pushed out a significant release to Mailroom. We’d prioritized feedback against our desired feature set, and introduced some new ideas of our own. At the root of the new release was a settings screen.

Badge Icons were a huge part of our 1.0 release feedback. We’d been hesitant to include them by default because, without Push (which I’ll get to in a minute), the counts were largely inaccurate most of the time.

Since we wanted to encourage people to start using TrueNew, we made that the default badge icon if enabled, but gave the user the ability to turn on unread counts instead.

Another major improvement was both workflow and performance related. If you only had one account and used Mailroom, launching the app to the dashboard was wasteful. If you left Mailroom on a given account screen to go to another app, launching put you back at the dashboard again, which was undesirable. We gave users the opportunity to remember the last account used, meaning that as soon as they launched the app they were where they left off last. This immediately made my email experience more efficient.

And as a bonus, Dave gave the user the option to lock screen orientation. Not something I was particularly needy for, but a nice touch nonetheless.

And then there’s that last setting. Cache management. What’s that, you ask?

Well that brings us to the biggest quiet improvement to Mailroom 1.1. The app is now taking advantage of Gmail’s HTML5 offline storage. What does this mean?

It means that every time you visit an account, the entire interface is cached locally and a HTML5 database is created/updated with the email on your screen. Kill your connection (because ATT sucks, because you’re on an airplane, or because you’re in a meeting) and Mailroom is still useful. In fact, you can not only read messages, but you can reply to messages and even COMPOSE NEW MESSAGES without a data connection. As soon as you reconnect, your cached messages are sent while retrieving new mail.

He even made the multi-account dashboard smart, only allowing you to enter accounts that had offline caches from a previous visit.

Yesterday, all of these 1.1 features hit the iPhone App store, and already a large percentage of our users have upgraded. One of them left us a review in the app store that commended us not only on the app and how great its icon is, but on Dave’s responsiveness to feature requests. Big win for us, that’s exactly what we wanted.

We’ve already talked about feature roadmap for 1.2 and 1.3 releases, and it’s very much in the works. The plan is to continue with iterative releases, process feedback, and continue to grow the user base all at once.

Two “issues” continue to arise: the lack of Push badge updates, and the $2.99 price point of the app.

First, push isn’t as “simple” as some of our reviewers seem to think it is. Among the scaling concerns we have about people who move a lot of email. I ran some averages and my smallest inbox gets well over 24,000 emails a year. Those numbers aren’t staggering, but across the customer base we’re targeting, that becomes a LOT of notifications to deliver.

The real technical challenge is more complicated though. In order to accurately update badge icons over push, we’d need to store email addresses and passwords on a server somewhere, and that’s a HUGE security risk that we can’t figure out how to justify. I know I wouldn’t want that info out there, and I have to imagine that our users wouldn’t like it either.

So until we come up with a more elegant way to support push, Dave has built in an app-specific URL handler. Calling mailroom://username@domain.com from another iPhone app or even from a mobile web page launches Mailroom, and even jumps straight to the account if there’s one in mailroom that matches the email address in the URL. We’re hoping that other push services like Boxcar and  Prowl can build in support for our app. We know it’s not the best solution, but given the infrastructure for Push provided by Apple, we’re pretty limited in what we can do. We don’t want to deliver a half-assed experience, so until we figure this out, Mailroom will not support push. If anyone has suggestions for how to overcome this hurdle, our ears are WIDE open, so please, sound off in the comments or via email.

And about that price point. Some customers seem to think that $2.99 is too much for an app that’s “just a webkit wrapper”. I won’t do more than touch on the fact that it’s not just a webkit wrapper for the right users and workflows since I’ve already explained here. But why $2.99? First, we’re targeting business users and we know it. They’re more comfortable spending more money on apps because in most cases, businesses equate cost with quality. But more importantly than that is the fact that this is, in most cases, a high-touch app.

99 cents for an app that you’re most likely going to touch at LEAST once an hour, if not several more times in a given day, feels undervalued. Like Tweetie, which I launch several times a day, I feel like I get an immense value for the $2.99 I spent on it.

Fact is, our first release might not have been worth $2.99 for everyone and you could say they got pegged with an “early adopter” tax. But since we’re not charging for the updates, and plan to roll them out often, we don’t think its really a tax at all. It just means that you will continually get more value from the app you already paid for.

We’re confident that future releases in our roadmap will continue to win people over the price point and even the “it’s just a webkit wrapper” theme. Mostly because, we’re listening. We hear what people like, don’t like, and how they are using the app. The more people feed back, the more they help to shape the future of Mailroom.

If you haven’t already, please consider heading to the App store and picking up a copy of Mailroom for your iPhone or iPod Touch. We’d love your feedback, and absolutely appreciate you supporting independent software development. You can also follow us on Twitter for app updates, or send us ideas and feedback there as well.

This week I’m included in Technically Philly’s sponsorship thank yous as their first “philanthropist level” sponsorship. It’s no secret that I’ve been a long time supporter of what Brian, Chris, and Sean do, and that’s not because they’ve written about me and IndyHall a bunch of times. I think they’ve identified a real need for covering the emerging technology community in Philadelphia with an honest, authentic, and approachable candor that is still backed by true journalistic ethics and execution.

I’ve got a lot of thoughts about their announcement of NewsInkubator, their Knight News Foundation grant application, that I’m still tuning and molding, but I think that it’s important that Technically Philly is able to sustain itself without the NEED for those grant resources.

They have a phenomenal community of readers, and an increasing number of those readers fall into the category of “we like what you do and want to do something about it”. My decision to sponsor is not to get a link or attribution every week…quite frankly I’d be just as happy without it. The reason I decided to sponsor TechnicallyPhilly was to lead with my actions rather than just my words.

I attended their first Technically Philly Happy Hour earlier this week and the ~30 people who also attended came from all corners of the technology scene in Philadelphia. My favorite part about the people who I met was that it was my first time seeing many of them. The fact that Technically Philly is able to act as a hub, as a connector, between disparate but related industries in Philadelphia is something that they recognize as valuable, and I’m thrilled that they’re able to find ways to execute with that connectedness.

Things like this, among many others, inspired me to put my money where my mouth is. $50/month isn’t nominal, and there’s of course a tradeoff. Think about $50:

It’s 3 dinners cooked at home instead of out at a restaurant (average $20). Homecooked food is better for you anyway.

It’s 5 walks (or even buses) across town instead of jumping in a taxi (average $10 from old city to 30th st). That walk will not only make you feel better, but you’ll see the city from the sidewalk instead of the street.

It’s 3 CDs or DVDs you wait to add to your collection (average $20). What’s the last good thing Hollywood put out anyway? Except IronMan and its impending sequel. I want to be Tony Stark when I grow up.

It’s 13 coffees brewed yourself instead of going to Starbucks and getting a $4 latte.

It’s 8 cheesesteaks (average $7). Ok, I hope you’re not eating 8 cheesesteaks a month. That’d be absurd.  http://thisiswhyyourefat.com/. ‘Nuff said.

And speaking of fat…you’re not even using that gym membership but you pay $40+/month for it. If you’re gonna toss that money at something, why not something that actually has value?

You get my point.

$50/month isn’t a subscription to Technically Philly, and I don’t think it should be thought of that way. It’s a way of supporting something that I hope becomes an institution in Philadelphia, and continues to grow with this community.

I’ve spent a lot of time on this blog talking about different marketing techniques and for the most part, those essays or rants usually amount to “try doing this” or “please, stop doing that”. Today, I want to document something a little bit different.

Selling software commercially is something that prior to the last 2 years, I had almost no exposure to. I had worked in retail where we sold other peoples’ titles, shelving boxes of discs for anywhere from $0.99 jewel box bargains to hundreds of dollars for operating systems.

It was always interesting to me that people would walk into a store and buy a physical piece of merchandise in order to put it on their computers. Obviously, before bandwidth got fast and cheap, there wasn’t really the option of distributing yourself, but even still…LOTS of software gets sold on the shelves. Even funnier, there are now online places where you can buy boxes of software, have them MAILED to you, and then you can install them. 

Let’s pause and think about how silly that is. That’s right. Pretty silly.

The other exposure to selling software I had was as a service provider: writing code to spec, and then someone else reaped the benefits of that ongoing.

These days, working with the crew at IndyHall Labs, I’ve gotten exposure to something completely different: independent software development and distribution.

Much like the music industry is experiencing, the tools are cheaper and the resources are more readily available for individuals to create, market, sell, and distribute their product, be it a 12 track rock -n- roll album or a useful piece of software, without the overhead of “mastering”, the complication of customers losing license cards, the struggle of controlling your shelf price, and more.

This week, the Multiplex team and I are experiencing something new and exciting for us, and that’s the inclusion in a software bundle being promoted and sold through MacUpdate.com‘s promo property, MUPromo.com [ref link]. In short, 11 apps are sold over a 2 week period with buckets of blitz marketing, and each of the software developers get a small cut of the sales of each bundle. The remainder goes into covering MacUpdate’s expenses, and the rest is profit for them. 

Bundles like these are increasingly common, and some other notable ones besides MacUpdate include MacHeist and MacZot. “Bundleware” is an old concept, a technique was often used to move old inventory. I’ve often used the lewd (but accurate) “Porno 3-pack” model to describe how it worked in the past: the vendor puts two “dud” flicks alongside a headline title, with a total price reduced to less than the total value of all 3 movies. Even if you don’t end up watching the duds, they got sold for more than zero dollars in revenue for the vendor.

What’s interesting is how MacUpdate and the others have successfully turned the bundleware model on its head. Most importantly, the new dynamic here that’s important to recognize is that the cost-per-copy of software trends to zero, since the software production costs are already sunk into the design and coding of the app. Since no copies need to be “mastered”, the cost to “produce” additional copies for sale isn’t zero (web host costs, for example), but it’s getting there. The largest cost that increases based on an increased customer base is customer support, which usually scales slower relative to the app’s sales.

So, with no “inventory” to worry about, bundle-dynamics leap ahead into something new, different, and pretty exciting. I want to talk about 4 key functions that I think have made this bundle work, and why we decided to be a part of it.

Dynamic #1: The Headliner Not totally unlike the “Porno 3-pack” I mentioned before, most bundles end up with at least one headliner app. Many times, that headliner’s retail value is greater than the bundle cost itself, making the deal a no-brainer for most potential customers. What’s neat, though, is that the volume of high-quality independently produced apps available to bundle-designers means that there are often MULTIPLE headliners, where nearly every app has the chance to be a headliner for someone… allowing the bundle to cater to a wider audience.

In the case of MacUpdate, there was more than one headliner depending on who you are, what your interests are, and how you as a consumer perceive value. 

Working down the promo page, headliner #1 was the “two bonus apps” for early purchasers… initially the first 15,000 bundle customers, and then later the limit was bumped to the first 20,000. There’s been some discussion on the bundle forum that maybe MU shouldn’t have moved that threshold, as some early-adopter customers feel that it “cheapened” the bundle for them. While economically the bundle value didn’t change, the value perception did and that’s important for someone who’s motivated by bargains, early adoption, and exclusivity. In this case, the cost to MacUpdate for providing those apps to an additional 5000 customers was zero.

Note: I’m not aware of the details of the deal between MacUpdate and the two “early bird special” apps, Jets n Guns Gold and CuteClips. It’s entirely possible that those titles only received a revenue share on bundles that included them, so they MAY have gained additional revenue with MacUpdate’s decision to move the bar. That’s pure and wild speculation, and a curiosity of my own.

The second headliner, that I believe many bought the bundle for, was the inclusion of two apps whose values individually exceed that of the bundle cost: Parallels and TechTool Pro are well known commercial use applications with extremely wide customer bases to begin with. Why would they lower their price-per-copy for this bundle?

As I mentioned before, all software being sold online has a near-to-zero per-copy “cost”, this becomes a marketing and customer acquisition play for the manufacturers of the software. It’s blitz revenue and TONS of visibility. While that visibility may not be causing people to learn about their software for the first time, it IS reminding potential customers that they still exist, and that’s a marketing expense worth measuring against the cost sunk into selling copies for a fraction of the retail price. Beyond the financial capital gained, I think there’s also some social capital gained by the larger software manufacturers since the smaller shops, like ours, appreciate the fact that their headliner title is helping us make some money. Software development culture is funny in the fact that many development shops make it a point to get out there, chum around with other dev shops at conferences, meetups, and other social gatherings. Big dogs like Parallels coming to hang around and help by pulling some weight, at least in my mind, is a gesture that doesn’t go unrecognized by the independent producers.

The third type of headliner is the “special interest” headliner. There were a couple of “categories” of apps in the MacUpdate bundle, and based on your own interests, those bundles might be the headliner for you.

Our app, Multiplex, was paired up with RipIt (also developed at IndyHall) and DVDRemasterPro as a trifecta of great tools for managing your movie collection with your Mac computer. Having been witness to the success of RipIt so far (and, we hope, the success to come for Multiplex), we know that there’s an audience of DVD collectors out there who want to do exactly the thing our apps were designed for: catalog their offline collection of DVDs, make it easy to recall and play on their media centers, as well as other devices they own that play video.

Given that Multiplex and RipIt alone are normally worth a total $53.99, that’s enough to make the bundle worth it. Toss in DVDRemasterPro, a $49.99 app, and you’ve got over a hundred dollars worth of software to help you with your DVD collection for half the price…and a bunch of other goodies as a bonus.

The point I’ve been trying to illustrate is that because all of these titles have a cost-per-copy approaching zero, there’s an incredible amount of flexibility in creating reasons for people to buy a bundle based on their own motivations. The bundle appears well rounded, but for enough people (over 20,000 at the time I’m writing this), there’s enough value generated for that person to justify the expense.

Dynamic #2: Urgency The MacUpdate bundle runs for 2 weeks. While not an extraordinarily short period of time, there are constraints. “While supplies last” is a fallacy, because again, it costs next to nothing to generate more supplies. In order to keep demand high, new constraints besides inventory need to be placed on the bundle sales.

2 weeks is a time constraint that, while artificial, informs the customer that “after these 2 weeks, the apps go back up to their normal price…so get ‘em now while you still can!”.

The early bird special does this too, suggesting that if you’re one of the first batch of people to buy the bundle, you get extra stuff.

The MacUpdate bundle page does a good job of highlighting the number of bundles sold, and how long you have left to buy.

Regardless of how high the bundles sold number climbs, I think that there is something about competitiveness built in human nature that makes us want to “beat the timer”, and get our purchase in before the other guy. It’s a counter-intuitive dynamic, but one that helps make bundle sales successful.

The other component to the “urgency” aspect is the timeframe in which us, as developers, make money. The important thing to remember is that we calculate success not just on the number of copies sold, but by the amount of cash in the bank.

Think of it this way. There are two paths to a million dollars: you can sell an app once for a million bucks, or you can sell it a million times for a dollar. Whichever has the shortest and most sustainable path to your million is the road you should take.

Dynamic #3: Self Promotion

Probably one of the most important components to bundle success is each individual bundle contributers’ own self interests: I’ve dropped the price of my app to the floor, so I want to promote the CRAP out of myself for doing so and get as many sales as possible, while also gaining brand recognition for when the bundle is over.

With 11 apps’ developers working that angle simultaneously, MacUpdate gains a massive sales team, but so does each individual developer! My own self interests benefit the other bundle contributors. Their self interests benefit me.

Furthermore, MacUpdate provides affiliate opportunities for developers and non-developers alike. This post, you may have noticed, is sprinkled with links to MUPromo.com that include our referral code. That’s because we make a couple extra bucks on each bundle sale that we actually refer. If you’ve found this article interesting and were considering buying the bundle anyway, please consider buying with our referral code and help some indie software developers make a buck.

See what I did there? That opportunity isn’t just available to me as a bundle contributor, but to the properties helping promote the bundle as well (like MacRumors, Smoking Apples, TUAW, and more).

And remember, at the end of the day, this is a promotional opportunity for MacUpdate. They not only make money on the bundles, but on ad-sales during the promo when more people are hammering MacUpdate.com to read more about the apps, their reviews, get their license keys, etc. 

Which brings me to my final point, and the real reason I wanted to put together this piece

Dynamic #4: Developer Relations In retail, there’s no usually relationship between the person selling to the customer, and the producer of the thing that the salesperson is hocking. At most, that sales person might get a kickback for selling one brand over another, but the sales person’s own brand loyalty and experience in what makes customers happy is usually what’s driving their sales suggestions.  

Bundles have gotten a bad wrap. Most notably, MacHeist.

I’m not going to get into the gory details of their indiscretions, but the record shows that they’ve had their shit called more than once for abusing the “value” they provide for their customers to line their own pockets instead of managing positive relationships with the developers that are giving them the opportunity to run the bundle in the first place. As long as 3 years ago, John Gruber was outlining the issues with how this “great deal” for consumers was selfishly benefiting the organizers while giving bundle app contributors a raw deal. It’s also worth noting that in december of 2006, MacHeist sold ~14,000 bundles and our (well, MacUpdate’s) bundle exceeded that quota within it’s first 48 hours. This most recent Holiday MacHeist bundle sold over 80,000 copies, but also took to some “extreme viral” (read: spammy) techniques for getting bundle purchasers to send links to their friends.

We pride ourselves in quality products, quality customer service, and both of those lead to quality relationships with our customers.

This is where I want to highlight the great job that’s being done by the team at MacUpdate, and why we decided to participate in this bundle.

I spent most of the bundle-prep time working with Nate Houle, who manages the MUPromo.com site. Nate was easygoing, straightforward with their interest and offer, and most importantly, I didn’t feel like I was being sold a line like I did when I spoke with other bundles’ representatives.

Nate was clearly interested in working with us instead of simply swapping licenses for a cut of the revenue. At some point in our IM conversations (yes, the entire MUPromo deal was done over IM), Nate said something that made me extremely confident in the success of this promotion:

  …we don’t bite the hands that feed us, without the indy developers none of us would have jobs…  

That kind of attitude goes a long way, and I think that genuine appreciation for the developers that support your bundle says a lot about Nate and his team.

Even when the initial bundle sales load crashed our licensing servers for the better part of the day, MacUpdate’s COO, Misha Sakellaropoulo, and their Lead Developer Chad Harrison were extremely calm, helpful, and supportive. I was on IM at various parts of the day during the first two days of the bundle running talking to Nate and Misha, and at each turn, they were as excited for us as we were. That “togetherness” is more ethereal than some of the other benefits of the bundle, but an important one for us, since it’s such a core value of how our apps get built in the first place.

One of the things on my to-do list for the next week is to continue the developer relations plan and reach out to the other developers who are participating in the bundle, introduce ourselves, and congratulate them as well. I hope that the other developers are planning on taking that time as well, as this is a great opportunity for us to celebrate the fun of being an indy mac developer together.

An honest and hearty “thank you” to the MacUpdate team for showing us that bundles don’t have to be evil, and helping me get my accelerated masters in “Bundle Dynamics”.

Final Shameless Self-Promo

Yes, we’re extremely excited about being a part of this bundle and it’s success so far. There’s still 12 and a half days to buy, so if you do, please consider using our referral link. If you could help even more by spreading the word and using the same link [http://tr.im/IHLabsMUPromo] or [http://mupromo.com/?ref=6602], we’d really really appreciate it.

A verbatim conversation, copied right out of Adium, with Jesse about making it easy to sign up for a website.

Jesse: You know, I really love the simplicity of Posterous.  I may start using it. Alex: its sllick Jesse: Yeah.  The no signup is the best non-feature around. Jesse: Oh and they allow custom domains.  Didn’t even realize that. Alex: mmm nice Alex: ive got a devils advocate argument about the “no signup necessary” workflow Alex: it plays into low-impact workflows, too, like openid/facebook logins Alex: clearly, you and i benefit Alex: but from a business standpoint, the ratio of dead accounts goes through the roof Alex: so you can report users as an astronomically high number Alex: but active users as a comparison looks bad, and on a business model, thats bothersome. Alex: not insurmountable Jesse: That’s very true.  I do like how it gives me instant gratification but then allows me to come sign up.

discuss.

How far we have come.

There was a time where I was stepping out into the world and despite the quality of the industry connections I did have, I felt very alone. I longed for a scene. Not the San Francisco tech scene. Not the New York tech scene. I longed for a scene that embraced everything that was already great about Philadelphia. The pieces were there, but they were fragmented.

2 years later, I’ve never been more sure that we’ve succeeded in catalyzing that thing that I, and many others, so disparately wanted. How we got here is a whole other story. But I wanted to share my latest excitement.

Geeks who Give is a post-Barcamp Philly brainstorm. The principle is simple, and very close to my heart:

Everyone has something to contribute. Long term goals include idea, goods & services, and resource banks from which we can draw as well as coordinating volunteer opportunities on an individual basis and organizing large scale volunteer efforts for continued organization-based support. The vision is for this to happen organically, for those things which resonate to surface, and those which don’t to naturally recede. Everyone in the community is invited to participate at whatever level they feel most comfortable — from planning & organizing outreach to attending events — to blogging, promoting and evangelizing the cause. We are more than the sum of our parts, and together, we are capable of anything.

Geeks who Give has organized their first event for this upcoming Tuesday, December 9th at National Mechanics. They will be hosting a Food Drive & Tweetup to benefit Philabundance. The event will take place at National Mechanics in Old City from 6 to 9pm.  At 7pm, local food podcasters Fork You will be giving a cooking demo with non-perishable food items. The event will be followed with everyone’s favorite, TechKaraoke at 9pm.

Admission is a minimum of 5 non-perishable food items. The food items must be packaged in boxes, cans or plastic bottles, and should not have to be refrigerated. In addition to drink specials, guests will receive 1 raffle ticket for the first 5 food items, and more tickets for additional food items. The current list of raffle prizes includes:

• Dinner with the City Paper food critic, David Snyder, PhilaFoodie,
• Dinner for Two at Fork in Philadelphia,
• A Gift Certificate and T-shirt from Tattooed Mom’s,
• Treats courtesy of Open Source Cupcakes,
• A $75 gift certificate to the Wine School of Philadelphia.

And more prizes are being added every day.

I encourage everyone to join us for this event, bring your dontations, and help out an incredibly important cause in our city.

I just had my first post go live on mashable.com, to the tune of “how to know if you should fire your social media consultant“.

I was a little nervous posting this, not because I wasn’t sure of the contents, but because I wasn’t sure who would take it personally, if anyone. So far, so good, though.

Thanks

Thanks to everyone for the kind words, and the comments. And most of all, thanks to Mashable for the shot at writing for them. Hoping this becomes a regular thing!

What’s Next

Now, on to the counter-post. It’s not my style to walk into a room, punch everyone in the face, and walk out. This first post was just that: a first post. I have a lot more ideas that I’m really stoked to put out there, here on dangerouslyawesome.com as well as on Mashable.

So the counter post that people seem to be interested in is, “how do you hire a social media consultant”? I’ve got some thoughts already, and have been kicking it around with some of my friends and mentors. But I’m curious what you have to say.

So I’m turning it into a contest. That’s right.

How to get cool stuff and save companies from themselves at the same time.

You see, a few weeks back, Samsung sent me and a few of other bloggers I know this T220 22″ monitor to give away any way we like. Ill be honest, I thought it was a scam. I asked what the strings attached were, and he said “We like your blog because it’s both tech-y, business-y, and personal.  And on a personal note, I think you’re a great writer. ” You had me at “we like your blog”, Greg! Greg went on to assure me everything was cool, and low and behold, a slim box containing a very sexy-looking screen showed up behind my desk while I was on the road this month. I haven’t opened it to try it out, but that’s because I want to give it to you.

And by you, I mean the person who gives the best 5 tips for hiring a social media consultant in the comments of my blog. 5 tips, any way you want to serve them up. Text, video, whatever! I’ll sort through them with the same friends and mentors that reacted to my post, and pick what we think are the best. Not only do you then get the monitor, but I’ll credit you in a follow up post that I’ll be writing.

I’ll keep the comments open for up to 2 weeks, and then we’ll rock out.

How d’you like them apples?

What’s up, friends of the “no-collar generation”.

Many of you know that I’ve been working with the CEO of ChoiceShirts, Matt Cohen, on a number of initiatives for quite a while. Our most recent partnership has produced something that I’ve talked about doing “right” for quite a while, making a really easy way to put the contents of tweet on a t-shirt.

Why on earth would we do that? Well, a few reasons:

• Matt and I, like many of you, really love Twitter. Like, really love Twitter. I <3 you Twitter.
• Matt and I, like many of you, really love t-shirts. Just last week, Allen Stern of CenterNetworks said to me at DreamIT’s funding day, “I don’t think I’ve ever seen you NOT wearing a t-shirt”. It was an off day, what can I say.
• Twitter is a really great channel for collecting funny, inspirational, or memorable one-liners. More and more often, we heard from others or thought ourselves, “that tweet would make a great shirt”.
• We wanted to try out some new tools in the ChoiceShirts design studio toolkit, as well as make a case for how we can build out new ones. ChoiceTweets is one of what we hope are many prototypes to showcase new and fun ways to get your content onto a t-shirt. A new vehicle for your content so YOU can make money. That’s what we’re really excited about.

Neato! So how does it work?

The whole thing is powered by a bookmarklet. You can read more about how that works on our how-to page. Not sure what tweets you might want to put on a shirt? Take a look at some of the one’s we’ve done, as well as any tweets that other users are turning into tweeshirts.

Also, don’t miss the Merlin Mann collection! Merlin’s tweets are often angry, but humorous. As other prolific tweeters have large numbers of shirts generated from their tweets, we’ll add new featured collections. Maybe yours?

Developer support baked in

For the time being, the feature set is small but that won’t last long! In the mean time, if you have created a Twitter client (web or desktop) and want to include “ChoiceTweets support”, all you need to do is add an icon that links to the same URL as the Tweet’s permalink, and change the Base URL from http://twitter.com to http://choicetweets.com. More on that on our Developers page.

GO! Check it out!

This is the first iteration of the idea, and we’re excited to see how people use it and add new features and learn lessons for the next site that we build. That’s why we’re using UserVoice to collect feature requests! Be sure to add your ideas there after you’ve made your first Tweeshirt.

Big thumbs up to Erik Kastner, who took on some fun challenges with generating the images necessary to make this concept work. I always enjoy working with Erik, and look forward to having him continue to lend his development expertise and problemsolving prowess as this project matures.

And of course, I always appreciate Matt’s support and interest in taking new ideas like this for a spin.

So head over to ChoiceTweets.com, and grab the bookmarklet. And let me know what you think!

Note: my buddy Zach Inglis pointed out that some of his coworkers prototyped something similar in the past. We certainly knew that this had been done before, but thought there was LOTS of room for improvement! So thanks to those who inspired our creation, and we’re excited to continue to improve on the idea based on everyone’s feedback!

WARNING: This post contains extreme abuse of twitter lingo like “@replies and DMs”. Generally speaking, I’m opposed to this sort of language, however…the service is cool and I wanted to share it.

Back when the ‘track via SMS’ feature was still enabled on Twitter, I honestly did not use it…I didn’t find myself with a burning desire to keep an eye on any particular keywords. Since then, my use of twitter has increased, and my reliance on it for communication has changed. I won’t say it’s gone up or down, but the way I use it is certainly different.

I find myself checking Summize/Twitter Search much more often for ‘@replies’ to my username and IndyHall. The biggest reason that I rely more on replies via Search is because I don’t follow everyone who follows me. Not because I’m a hater (far from it) but because Twitter is completely USELESS to me with that many people in my timeline. But I’m increasingly disappointed when I miss replies from people who can’t direct message me since I’m not following them back, especially when I’m away from my computer.

So, with Summize being acquired and energy going into the development of the Twitter Search API, I was stoked to see a really great project announced on the Twitter developer list: TweetTrak.

Functional and still low to the ground, TweetTrak uses the Direct Message -> SMS capabilities of Twitter + the search API to return tracking-style information via SMS, with a simple toggle command to turn it on and off.

The new features that are mapped out for the next iteration are smart, too: user ignore, and a control panel to set up your tracking terms (I imagine this will act a lot like Google Alerts, which I also love and use).

So while this entire system still relies on a system that occasionally lags (Twitter’s SMS and the recently acquired Summize), this is the best stop-gap we’ve had since Summize itself, and I welcome it with open arms, especially with all of the conference going I have lined up.

Check it out, and be gentile! And this should probably go without saying: make sure you have unlimited SMS if you’re doing ANYTHING with Twitter via SMS. Don’t be an idiot.