MacStories Interviews: Alex Payne

[MacStories Interviews is a new series of email interviews and conversations with with well-known developers, bloggers, journalists, geeks.]

Please welcome Alex Payne, cofounder and CTO of BankSimple. You can follow him on Twitter as @al3x. The interview was conducted from October 11th to November 15th.

- Tell me a little about yourself: who are you, what do you do, etc…?

My name is Alex Payne. I’m 27, and I’m the CTO and cofounder of BankSimple, a startup combining modern technology with extraordinary customer service to enable a seamless, worry-free banking experience. Before joining BankSimple in May of this year, I was one of the first engineers at Twitter, where I worked for 3.5 years. Last year I coauthored “Programming Scala” for O’Reilly with Dean Wampler. I’m deeply interested in programming language design and implementation, minimalist art, cocktails and spirits, and all sorts of other things. My wife and I just moved to Portland, Oregon a few months ago, and just recently moved into our first house.

- What’s your current setup?

As far as my setup goes, my only machine right now is a 2.66 GHz MacBook Pro that I bought this past summer. I’ve put 8GB of RAM in it, and I added an aftermarket 100GB Patriot Inferno SSD hard drive that I’ve been pretty happy with. I usually have a 30” Apple Cinema Display and Bose QC3 headphones plugged into it. I carry a black iPhone 4 all the time, and I have a 64GB iPad in a DODOcase that usually hangs out on the coffee table, but also comes with me on trips. I like to work standing, so I have a Steelcase AirTouch at home, and my coworking space was nice enough to get a couple of GeekDesks that we built with custom tops.

- I see you’re using a SSD on your MacBook Pro. I’m considering an upgrade by the end of next month - is it really worth it? Have you experienced noticeable differences when switching from a regular hard drive?

It’s absolutely been worth it. My previous machine had an SSD, and I got used to it. When I got my current machine without an SSD, it felt slow, even though it has a faster processor. It didn’t really feel fast until I did the upgrade.

- The funny thing is after reading your reply I couldn’t wait and bought a SSD. I just couldn’t wait any longer.

Back to the devices you own, the iPad. How does it fit in your workflow? Have you managed to get anything done with it, or does it simply “hang out on the coffee table” for usual morning reads?

The iPad is, more than anything, a travel machine for me. When on the road I use it for reading books, catching up on what’s in my Instapaper, watching movies, sending email, keeping up with Twitter, and so much more. The fact that the battery lasts forever and it’s lightweight make it perfect for demanding trips.

The rest of the time, it’s mostly a consumption device for me. At home, I use it mostly for books (iBooks, Kindle), feed reading (Reeder), and news (NY Times, BBC, etc.). I’ll use it to control the Mac mini that serves as our TV via Rowmote Pro. As far as more productive apps go, I do really like OmniFocus for iPad; its review mode is far superior than what’s available on the desktop version.

- Why both iBooks and Kindle?

And if I may ask, how long have you been using OmniFocus? I’ve been a loyal user for almost a year now and I don’t want to go back to anything else.

I use both iBooks and Kindle because the two stores have different selections. I also had a bunch of books that I purchased for a physical Kindle that I got rid of once the iPad was released.

I used an early beta version of OmniFocus ages ago and found it too complicated. Since then, though, my life has gotten more complicated and their interface has improved, so it all worked out! This time around, I’ve only been using OmniFocus for several weeks. So far so good. I have to resist the temptation to play with other “productivity” tools because I find that category of software interesting, but I’m not drawn to other apps because I feel OmniFocus is lacking in any way. It’s extremely flexible.

- Exactly. Flexibility is the real advantage of OF over its competitors, especially when it comes to playing with bookmarklets, shortcuts, integration with Basecamp. Yes, I’ve done that, too.

Speaking of productivity: how are Apple devices and apps fitting in your daily job at Banksimple? What’s your take on the improved Enterprise features for iPhone on iOS 4?

Well, I’ve worked on a Mac for years. Most of my colleagues are on Macs, too, including a couple of converts from Linux and Windows who are at least trying out Macs as their primary or secondary work machines. Part of that is the appeal of apps like iWork, but more generally it’s for the “it just works” factor. The ease with which the Mac handles new computing environments (hooking up to random projectors, connecting to strange wi-fi networks, etc.) is a big selling point. Once my non-Mac colleagues saw some of those features, they were sold.

We’re running the Propane Campfire client most of the day, as well as Dropbox. Other than that, the different folks at BankSimple all have their own particular favorites. We’re definitely not big enough to have a common “base image” for our systems, nor have we really looked at any of the enterprise features of iOS 4. It’s nice to know that stuff is there, though, for when we grow into it.

- Speaking of Mac applications, a few days ago Yojimbo 3 came out and with it came a companion iPad app as well. So I went through some old reviews and articles I had saved for future reference, and I stumbled upon this post of yours, once again:

Computers work best with structured data. Everything Buckets discourage the use of structured data by providing a convenient place to commingle “structureless” data like RTF and PDF documents. Rather than forcing the user to figure out the rhyme and reason of their data (for example, by putting receipts in a financial management application and addresses in an address book), Everything Buckets cry: “throw it all in here! Search it! Maybe I’ll corrupt my proprietary database, but maybe I won’t and you’ll have the joy of sifting through a mire of RTF documents. Doesn’t that sound great?”

This proposition should not sound great. If you think you’re going to save time in the long run by throwing your data into a big bucket now, then sifting through it later, you are mistaken. There are better ways.

I’m a DEVONthink user myself, and I’m looking forward to the mobile app DEVONTechnologies is about to release. Almost 2 years after that article and with the iPad selling like hotcakes, do you still think structured data is a better approach? Even if Apple is slowly moving to a database system, and hundreds of 3rd party developers with them? Don’t you think the “everything bucket” model will eventually take over the Finder?

I still think structured data is a better idea for most computing tasks, yes. For example, while I appreciate the simplicity of something like Taskpaper, I’m using OmniFocus because its structured approach does more on my behalf. Because OmniFocus knows when and in what context and even where, geographically, my tasks are due, it can help me figure out what I should do at a particular moment in time and space. That’s cool.

I remain baffled by Yojimbo. I’ve had most of its functionality for a while by keeping the majority of my files in Dropbox. If I need a file on the go, I fire up the Dropbox iOS app. If I need to take a plaintext note, I do it in Simplenote, which now stores any and all revisions to my notes.

I don’t think an “everything bucket” model will take over the Finder so much as that files will live within apps dedicated to dealing with particular tasks. Not one app for everything, but one app for each thing, if that makes sense. As the Mac converges with iOS and ever more apps are tied to cloud storage, this model seems inevitable.

- Cloud storage is what intrigues me the most these days, especially when it comes to Apple rumors and speculations about “iTunes in the cloud”. Do you think the next version of OS X, Lion, will come with extended cloud-based capabilities?

I have no idea what Lion will bring. I can’t imagine that Apple is building that giant data center for nothing, but I think their approach to the cloud will be a bit different.

MobileMe never clicked for me. By the time I had need of it, Dropbox came along, and now I can’t imagine shelling out for the handful of features beyond iDisk that MobileMe brings to the table. I’d like to see Apple re-imagine MobileMe and iTunes sync into a unified, completely cloud-oriented solution.

- So you’re talking about a system that goes beyond music - something focused on making the entire experience (music, movies, apps, databases, files) accessible through the cloud?

Yes. That seems inevitable, doesn’t it? Ending the distinction of what data is where and simply focusing on the application experience, even across devices.

- And what do you think about the current state of web apps, compared to native applications? For example - are you guys at Banksimple planning on deploying native apps for mobile access, or focusing on better integrating the web experience with mobile devices?

I think web apps are always improving, but honestly, I’m not a big fan of the web as a rich application development platform. Just because you can doesn’t mean you should. I think a high-quality native app wins every time. We looked at the web options for a mobile app for BankSimple, but we’re doing native apps for iOS and Android.

- Now that you mention it: thoughts on Android?

I really wanted Android to be something special. I’ve tried several times now to switch, but each time I’ve been struck by a general lack of quality on the Android platform. The devices feel cheap. The software is ugly and buggy. Android hadn’t cultivated the same cult of design that encourages iOS developers to make their apps attractive and usable. Generally, Android feels like the Windows of the mobile world: it gets the job done, but that’s about all you can say for it.

- And what do you think of all these iPad competitors running Android coming out in the next months? Honestly, I’m just excited by whatever Palm is working on. I like webOS.

I think the Android iPad ripoffs have about as much chance as Tablet PCs did. Crappy hardware plus mediocre software does not equal a desirable product. I see a lot of people getting these cheap devices for Christmas and being pretty disappointed that they didn’t get a “real” iPad.

I’m excited by webOS too, but I’m not holding my breath for HP to do something smart with it. I worry that webOS had its moment to capture developer hearts and minds, and that moment is passed.

- If you were to develop an app from scratch, now — something you need but no one ever developed — what would that app be?

Well, BankSimple is that app in most respects, and that’s why I’m working on it. No one ever developed an easy, modern way to bank. I like to think of it as “banking as an app” – you install it, you put your money it, and it just works. That’s the goal, anyway.

If I had infinite free time, I’d probably work on a new text editor. It’s an idea I kick around with some friends every now and again. There just isn’t a good text editor that isn’t either crazy (Vim, Emacs) or abandoned and limited (TextMate). I use all three of those, and even sometimes try out various IDEs, but they all drive me crazy. Of course, I’d have to be crazy to actually write a text editor, because it needs to be free and open and developing it would be a huge time commitment.

- So I assume BankSimple is coming out both on the iPhone and iPad — or just iPhone?

We plan on iPhone, iPad, and Android as our initial suite of mobile apps.

- Before starting BankSimple, did you use any other financial webapps or native applications for, say, the Mac? BankSimple is, of course, a bigger project than a rather simple software to keep track of expenses, but I’m interested in your previous setups nonetheless.

Yes, I’ve tried a handful of financial apps. There are some quite nice ones for the Mac, but they can only do as much as the banks allow them to do, which isn’t much right now. I’m hoping we can offer a rich API that allows developers to get a bit more creative.

- Which are the Mac apps you use on a daily basis?

At the moment, I’ve got Google Chrome, Propane, and OmniFocus running all the time, along with utilities like Dropbox, ClipMenu, iStat Menus, SizeUp, and CoverSutra. I’m usually also running either Emacs or TextMate, Mailplane, Terminal, and iChat. Echofon, GitX, Skype, and Notational Velocity all get used at least once a day, usually. If I’m at home, I’ve probably got iTunes running. If I’m elsewhere, I rely on PandoraJam or a Fluid app for MOG for streaming music.

I try not to mess with my setup too much, but I do like trying out new apps and ways of working. I’m also always looking for apps that I can throw away. I fire up TrashMe pretty frequently and try to slim down my Applications folder. It’s hard to find the right balance between using apps that do one thing well and doing as much as you can with just a few apps.

- Have you ever felt “overwhelmed” by apps, on Mac and iOS?

Oh, absolutely. I think the iOS App Store does a pretty terrible job of exposing the best apps. If I need an app for something, I have to depend on my social network to recommend one for me. And, of course, I’m quick to return the favor when someone is searching for an app that I’m confident in.

One of the weird things about computing right now is the mix between desktop, mobile, and web apps. If you consider “pad” apps as distinct from mobile, it’s even more confusing. Should I use a desktop app to do this thing I need to do? Should I break out my iPad? Is there a web app for it, and is that going to be better? Will it still be around in six months? Will I get my data out? Does it have a mobile app that I can use on the go? It’s all completely overwhelming.

- How would you reorganize the App Store navigation if you could?

It’s no so much the navigation as the search quality. Developers are still able to game the results, and the results for obvious searches aren’t particularly useful. For a long time, when you searched the App Store for “Twitter” you got odd little applications that had some minor Twitter integration, rather than, say, the most popular dedicated Twitter clients in order of popularity and last update. The results for that query still aren’t great.