1. Most of the work I did at Facebook that actually launched publicly in some form was on Timeline, although other designers deserve much of the credit for the final product. As for the second part of the question, I think it's hard to understand the dynamics of larger organizations from the outside. There are obviously a lot of really talented designers who have done and still are doing great work inside of Facebook, but the nature of the product is such that it doesn't translate into New Shiny all the time. For a product that reaches more than a billion people, it's still amazing to me that one designer or engineer is able to have the kind of impact they're still able to have working on Facebook. But there's a high cost to change for a product like that, it's a highly interconnected system where even tiny changes have cascading impacts. A lot of the work you do as a designer in a large team supporting a mature product system doesn't see the light of day. That's just the nature of the work. It's not for everyone, and it's certainly not the easiest way to get a lot of individual glory in the broader design community, but it's possible to have a really big impact, and it can be really fulfilling.
2. I love it. I still use Rdio every day and I don't know what I would do without it. The initial launch of the "all-white" version of Rdio on the desktop was a big surprise to me, partly because they did all that work in a very short period of time after I left, so I hadn't seen any of it. It was a bold move, and there were some rough edges, but they've made a lot of refinements since then, and the design language has really matured as they've spread it to more platforms. I think it's great how closely they managed to anticipate where Apple ended up with iOS 7.
3. I never interacted with Steve directly, but there wasn't a single project I worked on at Apple where his feedback and direction was not immediately and directly felt. Phil Schiller did sit down next to me and take over my mouse once, though.

Yes, they were very different experiences. Going into all the various reasons why that's the case would probably take all week. I worked on a marketing team at Apple (the design of apple.com is part of the global marketing design team) and I worked on a product design team at Facebook, so it's a little bit apples to oranges anyway. Both companies value design as an integral part of the company's direction from the top, but obviously each product and company has their own goals and priorities. Sorry for the unsatisfying response, but there are at least 100 different ways to say "it's different because it's different." :)

I worked on EveryBlock from San Francisco for three years while the rest of the team was in Chicago. For me personally, it worked really well while we were building the first versions of the product, and I was the only designer. We were able to keep up a good rhythm of discussing things together and me being able to work things out on my own. I think it gets a lot harder when you're collaborating with other designers, or if you don't have a certain level of trust and basic patterns of communication built up with the people you're working with. I've never been able to work as effectively remotely when I need to collaborate directly with other people. In larger companies, when it's easy to get swamped with meetings and conversations from all sides, it's great to have the ability to take a day a week to work outside the office and get shit done, but I think it's pretty tough to do it all the time. It works for a lot of people, but it takes effort to do it right and avoid the pitfalls.

Sure, absolutely. Both places gave me an opportunity to work closely with a lot of incredibly smart and talented people all working at a very high level. I've learned more from the people I've worked with over the years than any class or book or conference.

As far as hiring, I think there are people who can be really successful in large organizations that don't do as well in other environments, so I don't think I'd be biased specifically towards that. There's a certain sense of rubber-stamp validation that if somebody made it through the gatekeepers at Fancy Company X, they must be good, but that doesn't always mean they will be a good fit for something else.

(At 6'5" I'm easy to spot, but I'm very wily.)

I don't know yet, ask again in a year. :)

I think the books that have influenced the way I design most aren't really design books. So much of the value created by designers is about making connections, and I think some of the best insights come from outside the scope of our field or the problems we face directly.

Seeing Is Forgetting The Name of the Thing One Sees, a series of conversations by Lawrence Weschler with the artist Robert Irwin, is one of the best books I've read on any kind of creative effort. Irwin is so articulate in retrospect about the way he has approached questions in his art over the years. http://www.amazon.com/Seeing-Forgetting-Name-Thing-Sees/dp/0520256093

Christopher Alexander's books about architecture, especially The Timeless Way of Building have been really influential on the way I think about design. A lot of the principles around pattern languages in interaction design are based on his ideas, but his whole line of thinking about architecture and how humans apply order to our world is fascinating, and directly relevant to digital product design.

Yes, Simmy always looks good. His hair is always perfect.

That's a relevant question at the moment, because we're structuring this new company to be able to work on many things over time. As we're starting out, there are lots of possibilities, but it can be tricky to develop a pattern of: what are the characteristics of a project we want to tackle? What are problems that are worth solving that we are especially suited to solve?

Jim Coudal has shared a list of questions he asks when they're considering a new project:

1. Will we be able to do good work?
2. Will we be able to make money?
3. Will we be able to learn a little something new along the way?

I think that's a good framing for thinking about new projects whether it's for a company or in an individual career. If you ask one or two of those questions and not the others, in my experience, it doesn't work out so well in the end.

I'm most comfortable in HTML and CSS, and I've written a lot of the front-end and template code for different web-focused projects I've worked on. Lately, I'm trying to find ways to learn enough about native mobile to build better prototypes, and think through native UI systems and flows in a way that takes the materials and how it's built into account better.

It has varied a lot over the years, at different companies and on different projects. In the beginning at Rdio, I was building a lot of the front-end templates, by the end of my time there, I was spending most of my time managing the design team and giving design feedback and direction. I tend to try to take a lot of things on on my own and work out all the details myself, so I've had to learn ways to work against that and be a better collaborator.

I don't think there are any shortcuts to having someone who is a designer in a position to make or meaningfully contribute to fundamental decisions about the company. On it's own, it's not a magic recipe for success, but it's the right start.

Thanks! Please let us know (help@insandoutsapp.com) if you have any feedback or suggestions.

Take something that you think is good and try to figure out why it's good. Copying things just for the sake of copying them doesn't really get you anywhere. But you can learn a lot from taking things apart and trying to reverse engineer the component decisions and the process that got them there. Eventually you will start to build up a vocabulary of common patterns and elements that go into things you think are good, and you start to be able to understand your own taste enough to create something yourself that falls in the same category.

Is that battery meter on fire?