Almost Famous: Ben Zotto of Cocoa Box Design

This week, we coffee’d at Coupa Cafe on the Stanford University campus to interview Ben Zotto. He’s the mind behind Cocoa Box Design, the app company responsible for Penultimate, a sleeper hit at the iPad App Store.

Who: Ben Zotto, lead everything (it’s a one-man shop).

Ben was at Microsoft and worked for Xoopit, the email-enhancement start-up acquired by Yahoo (YHOO).

What: Ben’s Penultimate brings a Moleskine notebook-style user interface to the iPad. He just released an update that allows you to rest your palm on the screen while writing, the same way you might with a pad and paper.

Why: It has been in the top tier of the Apple (AAPL) App Store for weeks.

Where: (Web site); @cocoabox (Twitter); San Francisco (analog place)

Who Else: Apps like PaperDesk and Idea Boards use the pen-and-surface interface. Penultimate does drawing a little differently, though. Ben says it’s about the ink.

Five Stats You Won’t Find in His Facebook Profile:

Worst Job: I’ve been pretty privileged. I was a short-term photocopy runner for the Junior World Ice Hockey Championships in Geneva when I was in my teens. It wasn’t bad, but I don’t suppose it played to all of my strengths.

School Days: I grew up in Boston, but we moved to Switzerland during my high school days. I left eighth grade in Massachusetts, maybe never before having left the state. And within a month of arriving in Geneva, we were on a history class trip to Florence. It was awesome.

Geek Crush: There are a lot of guys from my Microsoft (MSFT) days who are my programming heroes. Guys like Tracy Sharpe and Dinarte Morais. I’m also a big fan of Wil Shipley.

It’s something about his combination of making beautiful and functional software and being fiercely independent–you know, a coffee shop denizen–that I’m attracted to. I actually found the designer I worked with on Penultimate through him.

Gadget Freak: I don’t carry a lot of gadgets. I am pretty picky about my work set-up, though. I use an Apple extended keyboard from the 1980s with the heavy-duty key switches that I rescued off eBay (EBAY) and the Microsoft optical IntelliMouse, which is, for my money, the best mouse developed so far.

Early Internet Memory: Right after I moved to Switzerland, I had a friend back in Boston who would email me. It was probably 1992, so it wasn’t really email. He found some dial-up number at MIT that had an open gateway.

It wasn’t obvious then how you would send an email to an internal address where my dad worked. It was one of those early u-u gateway/bang-this/bang-that things. He finally figured out how to get it to work, and my dad’s secretary would print out these letters from my friend Micah back in Boston.

That was how I heard the news from Massachusetts for a little while. Micah is a recent recipient of a Ph.D in computer science from UPenn. Not a fool.

Bio in 140 Characters

Ben had an international childhood. He has worked at Microsoft, Xoopit and Yahoo. He writes software that he hopes is beautiful and useful.

The Five Questions

How long have you been developing Penultimate? Why is it a killer app when so many others don’t seem to be?

Originally, I developed an app called Handwriting for the iPhone. There was potential there, with the touchscreen, to give a personal touch to messages through handwriting that wasn’t there before. For that reason, I spent a lot of time working on the graphics math for the ink.

I wanted the input to really resemble the handwriting of the user. It turns out that getting digital ink to look real is a really subtle thing. I spent a lot of time getting it to move right, getting it to feel smooth and whatnot. I finally got it where I was happy with it.

I released the app and basically, nobody bought it.

People responded well, but I realized that anyone who used the app would only use the surface that they could see within the bounds of the iPhone screen, even though I made it so that you could scroll around easily to get a bigger surface for writing.

Size was clearly an issue.

The iPad coming out meant that all of a sudden something that was just more of a single tool like handwriting could be scaled up into an app with real uses, and all it took was more screen real estate.

Steve Jobs, in his iPad release presentation, said that if they’d added a stylus, they’d have gotten it wrong. Does the success of your app fly in the face of that vision?

It’s funny, I’d never heard that until now. I didn’t watch that speech.

When the iPad came out, I got this vision of doctors walking around making notes, and it looked like there would be lots of use cases where a keyboard just wasn’t ideal.

People would need to input info standing up, while moving and in portrait mode. From the pictures, it wasn’t clear the keyboard would be great for that.

I developed Handwriting and Penultimate to be used with your finger, and that’s how I use them most. And I think Apple has good reasons for not pushing that. They could have developed handwriting recognition, but for them, that draws away from what they are really trying to sell.

Handwriting recognition is really hard, and as soon as you do that and say you are going to do it with a finger, you have people saying, “Why doesn’t this thing recognize my handwriting better?”–instead of marveling at all the amazing things you can do with the platform.

Have you faced issues from Apple, developing a popular app that goes a little against the grain?

I’ve heard complaints about the App Store, but I’ve had a pretty good experience so far. It usually takes them about 48 hours to approve updates for my stuff. That said, there are some hardware things I’ve run into.

A big one is trying to get palm rejection in my app so that you can place your hand on the screen to write and not have it register as a touch.

On the iPad, Apple doesn’t expose those drivers to developers. On the MacBook, for instance, you can hook in the driver and get all the data–the width of the touch, rotation, everything.

All that is closed off for the iPad, so getting the natural handwriting position has been really challenging. I’m playing with that right now because it’s been one of the loudest requests.

You are embracing this use case that Apple seems to wish wasn’t there. What other requests are you getting from users who want to be able to write on their iPads?

I think form-filling is a big one. There are apps that do that, but their ink technology isn’t as good as mine, which is why I think I get those requests even though there are other apps in the field.

I got this great email from the head of a police department, who said that out in the field there are all these forms he has to fill, and he wants to take them with him and not have to bring paper.

There are all kinds. I got mail from a roofing contractor who wants to be able to snap his drawn lines to a grid to draw quick plans.

I’ve got friends who are doctors who think it’s a great idea, but say they could never use it because of HIPAA.

There seems to really be a lot of uses for being able to write by hand and make notes in this very natural way.

You worked in regular software before you did this. What is fundamentally different about developing for this platform? What are people missing about that?

I think a big difference today is that people expect updates much faster than before. It’s fundamentally different than shrink-wrapped software world, where you would spend lots of time making and refining a product, packaging it and shipping it out.

Today, people expect to see some kind of update or fix every couple of weeks and they expect them to be free. If you don’t issue an update for a while, people might begin to think you are dead.

Because the mobile platform apps are these single-use things, there is a perception that they are smaller or more simple and that therefore there is an entitlement to future updates. It’s great for users but really hard for developers.

There’s this ever-present question: “How much software is ‘three dollars worth’?”

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