It seems that there are only two ways you can go about defining a pricing model for your web app these days. Either you blatantly copy your competitors (or 37Signals if you don’t have any direct competition), or you juggle through different permutations until you get to something that “feels right.”

While thinking through a pricing model for BrainTrust, after numerous failed attempts (including the one shown on the site right now), I decided to write out some principles first.

1. There should be a free plan to give the casual user a taste of what we are about. Anything given for free should only give a taste, at a clearly limited scale. Not all features should be given out in the free version.

2. There should be a “recommended” plan. This plan should cost what we need the majority of our user base to be paying. It should also have the appropriate features to give the BEST OVERALL EXPERIENCE our product has to offer.

3. There should be a “cheap” plan for the skeptics, that includes all of the essential features but at a limited scale. Remember, we’re only giving a few limited features in the free plan, skeptics can upgrade to the chapo plan to get a feel for all the features. However, the cheapo plan still doesn’t provide the “best experience” — thereby giving the customer an incentive to upgrade to the recommended plan once their concerns have been alleviated.

4. Finally, there should be a “hail mary” plan. This is the fully equipped, no expenses spared version of your product at a triple digit price, to test out the upper limits of our market and our overall pricing assumptions.

5. Our customers should be able to take any of the paid experiences for a trial run. The trial run should be long enough for the custimer to run through all the important use cases the product supports.

6. There can be “filler plans” that give our customers a healthy gradation to pricier plans — so that our customers can slow upgrade to larger scales without having to jump straight to the “hail mary” plan.

I hope this helps. I’ll be sharing how our new pricing strategy works out for BrainTrust once we go live.

In the mean time, comments, thoughts. debates are all welcome.

I attended a panel last month ULS about PR and what they do for startups. To be honest, I went mainly for the networking and pitching opportunities, but the panel discussion itself turned out to be eye opening. Here’s why:

My perception of PR was completely wrong. In my own naiive way, I bucketed PR, Marketing, Advertising, Branding into one big bucket of “community building.”

The recipe was simple (albeit hard), pick your target audience, make your messaging consistent to target them, put out great content they care about, and they will come and sign up for your product!

In my own naiviete, I constantly focused on the customers. I didn’t think that in addition to my community of target customers, there is a separate but equally important community of people that I also need to connect and cultivate relationships with: the people that my target customers look to for advice… The press!

So if you’re working on your new venture, think about who your customers look to for advice, and make sure you try to include them into your community as well.

I was making myself a latte today on our little cuban espresso machine. As I was frothing the milk, I noticed that there was just not enough foaming action.

I thought for a bit… Should I keep going? Should I hit that big ugly red STOP button? Am I calling it too early? Will it begin frothing in another 10 seconds?

And then I stopped myself.

I realized that I was asking the wrong questions. The real question was, am I on the right trajectory? If I keep going, will I end up achieving the goal (a nice frothy latte)?

At this point, the answer became simple. At this rate, I wasn’t going to make it. And surprisingly through this lens, the STOP button didn’t look so ugly and scary anymore… Pushing it, pulling over and reevaluating became the obvious thing to do.

I realized that its the same thing in business. Getting stuck on specific bad outcomes and thinking about ways to compensate for each is a common pitfall startups make. They avoid pushing the STOP button and rethinking everything because that would mean admitting defeat.

BUT, if you focus on the trajectory, it forces you to visualize the bigger picture. Chances are, you’ll see your impending defeat, and at that point the STOP button won’t seem so scary. Instead, you’ll save a ton of time and pain, and get to success through course correction a lot faster.

As for my latte, after stopping, cleaning and restarting, I ended up with the perfect frothy latte.

The blogosphere, media, and the rest of us are all focusing on the wrong set of Facebook problems. The fact that Zuck thinks society is becoming more public (which it isn’t) isn’t the real problem.

The real problem is that social networks (such as Facebook, MySpace, Tagged, etc) are all failing to achieve the most fundamental goal that should be justifying their existence. They are miserably failing to answer the THREE most important questions any member of society tries to answer in the real world:

• Who should I start a company with?
• Who should I hang out with?
• Who should I make babies with?

All Facebook (and most other social networks) are today is a free service that wants me to brain dump as much information as possible, so that they can pimp it to Google and any other Ad-agency willing to pay for it.

We need to solve the actual problem

All is not lost. Facebook has done a great thing by building a social graph. It’s up to us (internet entrepreneurs) to utilize that and solve real problems — because it just doesn’t seem Facebook’s values are aligned to make any real impact at this point.

Not to jump to any solutions on how to solve my problem, but here’s just a few off the top of my head:

• Dating sites: tap into the social graph. tell me which friends of friends I should be dating (this is obviously theoretical, I’m married).

• Inc magazine: tap into the social graph, tell me which friends, or friends of friends, tend to like the same type of articles, or work in the same type of industry — if this person is a friend of a friend, its more likely that my values will be aligned with his.

• Foursquare: tell me which friends, or friends of friends tend to hang out at the same spots in my town. If a certain person also loves to get work done at the cafe, and is also friends with a random array of my close friends, chances are I should be hanging out with this person too.

• Ask My BrainTrust: they’re thinking hard about this already; they want to help people have private and meaningful conversations, only with the people that matter.

Somehow, I came across this video in my YouTube favorite’s list.

I’m not sure who first recommended it to me, but I find it amazing how it perfectly describes what an Entrepreneur goes through from starting on an initial idea to finishing with a successful business.

I watched it this morning, and I seriously got an emotional reaction from it. It was a reaction that I think only a small fraction of the 1.5 million people that have seen this video will truly understand.

Here’s how I would break it down:

The first 18 seconds
This is the part where you’ve come up with your idea. You don’t know if it will stick, or if it will be successful. You just know that it excites you, and that it makes you feel good, so you dance with it.

About a minute into the video
You’re still doing what feels good. It gets a bit tougher. You’ve got a handful of friends and family that are jiving with you and are there to support you, but they’re a little unsure, which makes you a little unsure. You wonder to yourself: Will this idea fly? You keep going, because it still feels good and you’ve gone this far, why not go all the way? You forge ahead with your idea.

The next 30 seconds
All of a sudden, things start to speed up. You see strange new faces, smiling, jiving with your idea. They feel good, you feel good. It’s all good.

From about a minute and 45 seconds onwards
This is where I almost cried. Seriously.
This is the point that every entrepreneur lives for. The part where you’ve got people that truly believe in your idea, and they’ve let go of any reservations and are just swarming at you, because they want to be part of your movement.

At the end of the video
You take a step back, and look at how you’ve changed the world. And you say, Yes, I pulled it off. And now, it’s not your idea anymore, it is bigger than that. Time to move on.

This is what every entrepreneur lives for. There are a lot of alternate paths that this video doesn’t show. However, I truly believe that if you stick to your idea and execute relentlessly with dedication, this is the one true path to entitlement.

Tonight, I decided to invest in the full 1h20m and watch the Google Wave demo video on YouTube. I tend to analyze and think about things at the meta-level, and at that level, overall, nothing in the demo was all too surprising. Here are my thoughts.

The Wave UI

Google is largely an engineering driven company. I think if it wasn’t for the hip Product Managers running around trying to keep up with the PhDs, their UIs would be composed of mainly command line interfaces with maybe some SOAP calls if you wanted to get fancy.

With that said, I thought the UI they pulled together for the demo, albeit a little clunky in certain parts, was by and large quite impressive. The first thought that came into my mind when I saw the UI was “holy shit, that’s what Rikk and that other crazy guy was trying to pull for Plaxo 3.0“

At the time, we just couldn’t make the damn thing fast enough, nor intuitive enough, and here it was, in all of it’s glory, with the strech and contract, working perfectly.

Was it that we had sucky engineers? Has the web really matured that much that they can finally managed to make this UI fly (and fast)? Is it just demo magic?

I think Google pulled it off because the Web has really matured… I’ll tell you why, but it connects more with the next section, the Wave’s architecture.

The Wave Architecture

I think the Wave is one of the first cases on the Internet where we are truly changing the trajectory in how we develop our systems and their architecture.
To put it in context with a maturity graph that we are familiar with, it’s like we’re finally moving away from coding our applications procedurally to a paradigm that is closer to object oriented. Furthermore, we’re finally moving away from the concept of a Request -> Reply, or a Ping -> Pong, or even a Poll -> Resulset, to a truly event driven system where each aspect of a page is operating semi-autonomously.

Congratulations Internet, in some twisted backwards yet forward way, you’ve finally caught up with best-practices of Enterprise Architecture.

I think the federated model that Google is proposing, and the architecture and framework that they are bringing to the table is truly exciting and will hopefully take us in a new direction in not only increasing developer productivity but also improving in our ability to develop truly rich and scalable internet applications that do no rely on sucky inaccessible frameworks (i.e. Flex or Flash).

Waves, the concept

The second part of the demo moved beyond the UI, and the architecture, and more to some theories around the application of this technology.

Now, I don’t know about you, but co-editing a document sounds like a utter disaster to me and beyond being amazing demo-candy, I can think of very few real world uses for it.

But even beyond that, I couldn’t help but think of that “3rd window” showing the content of the wave as being just one giant fucking iFrame throughout the whole demo. Here’s why:

When you look at technology over the past 10 years, especially internet technology and technology for solving real world problems and actually making people’s lives easier, us, as an industry, have pretty much failed!

I think with stuff like microformats and other such semantic markup, we were finally moving toward making data more accessible, open and meaningful. But with Waves, with this munging of all kinds of data, with free-form typing, just with this whole WAVE, I’m starting to fear that we’re once again regressing in our goal of making people’s lives better through technology instead of more complicated.

It is clear that with Google making APIs available and their encouragement to build widgets and integrations, the onus is on us to create meaningful technology. Let’s just say we’ll have to keep a close eye on things… are we truly improving our lives with “more” or just complicating it even more? Creating more jobs for low-end data workers to deal with shitty technology solutions munged together for the lack of a proper technology solution that reduces human involvement rather than increase it.

Still an amazing achievement

In case I haven’t made it clear, I think the Wave team, after about a year and change of work has produced something extraordinary and potentially game changing.

Lastly, as another meta-level thought, I wonder if Apple’s technology supporting the iPhone, iTunes and even their Web Offerings are just as fancy and forward thinking. Apple’s presentations always focus on the end-user experience, whereas Google focused much more on the infrastructure-level stuff. Just a thought, Apple, are you there? Want to provide something game changing to the developer community (through a federated model perhaps?)

In case I didn’t make it clear in my previous post on Omaha and BIGOmaha, it was an absolutely amazing time! My original plan was to write a follow-up post on BIGOmaha itself, and my take on each of the keynotes. But..as Jason Fried says, “inspiration is perishable.” I don’t want to write about that anymore.

Instead, I think there is a lot to be said about why BIGOmaha turned out to be so awesome, beyond just the content of the keynotes. Furthermore, I think anyone can follow some of the tactics Dusty and Jeff used to host their own regional conference and make it awesome. Here’s what you have to do:

Keep it intimate

When all the Ruby developers in NYC get together, or the new-media types congregate for SXSW Interactive, you get a crowd of hundreds if not thousands. With BIGOmaha, albeit not by design but more because they’re just starting out, they sold out to their capacity of ~300. This meant a crowd of locals (and a handful from far away), that got together at the conference and first felt a feeling of serendipity (“oh my..you’re in Omaha and you love Ruby too?!”) followed by a feeling of intimacy since as this small crowd of cool people all went through the journey that was BIGOmaha.

Make it a journey

BIGOmaha was more of a journey than just a conference. It started with an opening wine show along with a live band. Breakfast was served in the morning, we all travelled across the street for lunch, had a post-conference wine party and then had a closing party at a lounge come art gallery.

As we walked from event to event, ate food, drank, listened, talked and shared, it all become much more than just going into a conference; it became an experience and a journey. Strange unknown faces or what once was just a twitter username you followed became familiar faces and even friends. Sweet.

Think User Experience

To go from Keynote #1 to Keynote #2 for SXSW, I once had to take two escalators, and elevator and then jump into the staircase only to realize I was on the “wrong part of the building.” The wrong fucking part of the building?! With BIGOmaha, even the bathroom signs had more thought given to it in terms of User Experience.

Here was the awesome, awesome, Blogger’s Lounge…awesome!

Be a gracious host

Dusty and Jeff didn’t look at their jobs as just throwing a conference together with hot speakers, I think they looked at it as hosting a party in their own home town. I felt like I was invited to their own living room, where they gave us a tour of their house, made sure I was comfortable, and took me to all the hot places in town to make sure I have a good time.

This not only made BIGOmaha great, but also gave it a humanistic feel, where it made a New Yorker travelling to Nebraska feel like I was visiting an old friend…rather than a strange city for some random conference.

With all that said.. I think Dusty and Jeff came across an incredibly awesome formula for throwing a conference. It wouldn’t have been as awesome as it was without their hardwork, but I think there is lots to learn from these two. With their techniques, I’d love to see a BIGNewYork, BIGAustin or even a BIGIowa.

I had the most amazing time at BIG Omaha this past week. I remember the first time I heard about it, when I loaded up the site from some random tweet related to SXSW. The site read:

We’re bringing
forward-thinking,
creatives,
entrepreneurs,
and innovators
to Omaha.

Something about that just clicked. I had gotten bored of SXSW after going for two years, which left a void in me from getting my web-conference fix. I promptly booked my tickets and was psyched!

Although I immediately had extremely high hopes about BIGOmaha, I expected very little from Omaha itself. “Why’re you going to Nebraska?!” asked family and friends when I told them about my plans.

To my utter surprise, while BIGOmaha itself far exceeded my already high expectations, something magical happened: I fell in love with Omaha itself…and here’s why.

I did not take these pictures, which is why I am linking to the original photographer’s flickr page, feel free to compliment them for wonderfully capturing Omaha’s beauty

The thing that I loved the most about Omaha was it’s pure authencitity. Not just the place itself, but the people, the things, and even the concepts.

Maybe it was all the brick buildings, sure, they were old, but they showed their age with class, with character, almost like a broken in leather jacket instead of the crumpled faux leather most other small cities exhibit ….so authentic.

The restaurants weren’t your standard Chinese place, Italian place and Steak house, it was a plethora of restaurants, with distinct styles, outdoor seating, people buzzing, even some random kid playing the violin on the street corner.

And as for the concepts adding to it’s authenticity, take for example this two-screen theater only playing classics and indy films, started by a young entrepreneur that has never done anything like this before.

Or even these converted warehouse come lofts, all part of a revitalization project running over the past decade through Omaha’s downtown.

Sure BIGOmaha was great, but I think an even greater success was for Dusty and JS to show all of us a place where creatives and entrepreneurs are gathering and making things happen. BIGOmaha wasn’t just a conference to me, it was a wakeup call that you don’t necessarily have to be in San Francisco to drink tea, tweet and create the next web innovation that impacts the world. Omaha has a community of like-minded thinkers waiting to welcome you.

Typography. What a beautiful thing. I’ve always been attracted to the design and aesthetics of products. Until I started working on AMBT, I never realized what a huge role typography plays in making something look good.

I am simply amazed at how much “aesthetic” you can add to a design simply by using a concoction of elegant typefaces.

The web happens to have a ton of great resources if you want to learn more:

• 8 Simple Ways to Improve Typography In Your Designs

• Five simple steps to better typography

• The Elements of Typographic Style Applied to the Web