Hmm I wish I had a good answer for this :) One positive of having a wide mix of products is that if we hit a wall with something we're working on or if we’re not feeling creative on a particular problem, there's plenty of other tasks we can move over to until inspiration hits.

In general, for me, I also find it useful to mix up the opinions I surround my self with. I find if I'm following the same set of people on Twitter for a long period of time then all I see are the same group of opinions and that can be pretty dangerous. I unfollow and mute without mercy and try to mix up the group of people I follow every few months just to get a diversity of perspectives in my feed.

That’s a tough one. I’ve always dabbled between both worlds, mostly out of necessity. I’m an impatient person, so waiting on someone to help me develop or design something hasn’t ever been attractive. When you’re on a small team like we are, you don’t always have the benefit of a dedicated team of developers or designers to work alongside, so you’re forced to adapt and learn new skills in order to get things done. With that said, it’s always helpful to be surrounded by people you can bounce a question off of or get their opinion when you hit a wall.

Regarding staying fresh and adept: I think deliberate practice through side projects and experiments help a lot with this. For me, most of my day-to-day work is on large monolithic code bases where what you can do is dictated by decisions made a year or so ago, like your build system, framework, or style guide. This isn’t always the easiest environment to try cutting edge stuff, because that stuff wasn’t around when the big decisions were made a year ago. I usually have a ton of ideas for side projects and use those as an opportunity to take a first crack at trying a new library (like React), app (like Sketch), or service (like AWS Lambda). Eventually I can apply those lessons when we work on a new version of a project, refactor, or start something from scratch.

Would I recommend it? Definitely, if that’s something you’re interested in. To use some buzzwords: It’s great career capital and widens the adjacent (1) possible (2).

Re. #5 for me:

I’m obsessed with usesthis.com — it’s super interesting to me to see what other software developers are using in their practice, but also what scientists, chefs, and musicans are using. The site even has an API.

I also have to mention Kevin Kelly’s new book, “The Inevitable”. You gotta read it.

Re. #4: We really focused on building a CMS that developers would love to build for and that everyone would love to use.

So some things developers will love is:

• Full compatibility with Jekyll — it’s open source, you can run it offline, and it’s the same thing GitHub Pages uses to power over half a million sites.
• GitHub Sync, which keeps your source files locally, in GitHub, and in Siteleaf all in sync. When you make an edit in Siteleaf or push a local change to GitHub, everything syncs which gives you a time machine for your content.
• A full API that developers can use to manage their content. Hell, you could create your own CMS using just our API. (The Siteleaf Admin uses the same API endpoints). I’m using the API personally to export my Kindle and iBooks highlights online.

From the client or content manager side: I’m a bit biased but I think we’ve built and designed a pretty kickass admin interface for you to manage your site in.

Adding onto this: We've also been fortunate to find clients who enjoy working with us enough that they keep a monthly retainer with us to do ongoing work (new features, bug fixes, etc). Having a few of these makes life much easier to work on our own things, since it saves us from searching for new consulting gigs and cuts way down on the number of meetings taking up our time.

Re. #1: Good question :) The day-to-day is pretty relaxed. Skylar and I meet every Monday morning to catch up on the latest stuff: what we’re working on, what client work is in the pipeline, and what needs done to get to where we want to be—whether that’s launching a new feature or something a bit more long-term. Outside of the Monday morning catch up, we don’t really have any other meetings unless we’re meeting with a client. Most of the back-and-forth between the team is through Slack, and we have a channel for each product and client to keep things organized. Most of the stuff we know we need to do is a GitHub issue in the corresponding project’s repo and we try to use GitHub’s Milestone feature to group the issues by priority. This setup isn't perfect but it works okay for a small team like ours.

One thing that we do with Dropmark that pushes us to keep things moving forward is a monthly email that we send out. This was partially inspired by something Nathan Kontny wrote about doing when he took over Highrise from 37Signals:

On day one, I established a train schedule – we'd make major announcements on a regular basis. If something isn't ready, it misses the train. But an announcement is going out; something better be on it.

We started doing a similar thing at the beginning of the year, and at the end of every month we send out an email — most months we’ve had a new feature or improvement that we’ve been able to announce.

We'll take all the feedback we can get!

Thanks Toby! The new plans are per site and each site is billed individually. If you have a legacy plan, check the answer in the FAQ on the Plans page :)

The two "Pocket" books are epubs I curated:

2012: http://sawyerhollenshead.com/downloads/pocket-2012/ 2013: http://sawyerhollenshead.com/downloads/pocket-ii/

Haven't gotten around to integrating with the Instapaper or Pocket API's yet.