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My Core Productivity Suite

I launched a startup in 2007-2008 for which the essential idea was to have a centralized place to store content from around the web, then access it from any device. It doesn’t sound very innovative today, but at the time it was (more on that experience in a subsequent post).

I was then, and remain today, passionate about the idea that all my content should be easily accessible via any device. IMAP for email was an early, successful implementation of the concept, and I believed the same approach should be applied to most, if not all, other content. For productivity, I was an early subscriber to The Omni Group’s OmniSync solution to keep my OmniFocus content up-to-date on both my Mac and iPhone. Today, centralized storage and syncing of email, notes, to dos, calendar items, and other productivity solutions is requirement number 1. More and more, support for inner app compatibility is also becoming table stakes.

I remain an unabashed user of Apple products, and my current productivity choices are a direct reflection of my bias. I’ll review each product in more detail later, but here’s what I use and why:

  • Spark for Email on macOS and iOS. Honestly, I preferred Astro, but they were purchased by Slack last year, and ended support for Astro as a standalone email client (it also handled calendars and Slack messages). I use Spark because it features all the basics (support for wide variety of email service providers, multi-device syncing, swipe actions for quick processing, etc.) in an aesthetically pleasing but highly functional user interface. I have recently started using their Quick Reply feature more often, which is like using Emoji to respond to an SMS message, but the feature appears slow.
  • Things 3 for Task Management on macOS and iOS. Believe me, I’ve tried them all (OmniFocus, ToDoist, Wunderlist, Remember the Milk, Reminders, and many more). Things 3 is my current favorite. The UI is really polished and easy to grok. It supports several working styles, from Getting Things Done, to daily list making, to obsessive, plan every task, every day, in perpetuity. Two of my favorite features, used in tandem, are the ability to specify when I should start focusing on something and when it’s due as separate dates. For example, I can specify that I want to start working on something at the beginning of next month, but its not due until the end. The task will be hidden from view until the start date, and my due date is clearly visible.
  • Bear for Notes on macOS and iOS: Bear is my favorite new-ish app. I don’t use dark mode on my Mac, but I do in Bear. I love Bear’s Markdown support, and very simple user interface, and it’s tagging feature for keeping up with Notes as my library grows. Bear is full-featured, but just the features I need, which I suspect is true for many people. I can’t say a ton about it. It just works, and it’s right for me.

I still using Apple’s built-in calendars, mostly because I personally can’t justify the cost of Fantastical on multiple devices. And I still use Reminders and Notes for certain use cases (like asking Siri on my Apple Watch to remind me of something, or to scan files using Notes’ very capable scanning feature). But these three solutions from independent software developers are my go-to apps for now.

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It’s Time to Blow Up iTunes

Editor’s Note: I wrote the original draft of this post in December 2018 and never published it. With the launch of Catalina, I thought it was worth posting.

When I wrote recently about some redesign ideas for Apple Music on iOS, I naturally also took a look at the current state of iTunes on Mac OS X. And were I to deliver a state-of-the-union address for the iTunes nation, I’d have to conclude that it is dire.

Keep in mind that I’m talking about the latest version of iTunes (12.4), according to the dialog I see when I check for updates. It features the return of the sidebar when viewing “my” media (My Music, My Movies, My TV Shows); the sidebar doesn’t exist for any other sub-media options like For You, Unwatched or Store.

To be fair, this version is an improvement. There’s a really consistent design pattern at work: choose a media type from the dropdown menu in the upper left corner of the screen, access my content from the left sidebar, and access other content, like the stores, from sub-menus for each media. If I’m viewing My Music and switch from Music to Movies, I see My Movies. If I’m viewing the iTunes Store under Movies and switch to TV Shows, I see the iTunes Store filtered for TV Shows instead of Movies. In some ways, this is a very smooth, elegant and consistent user experience.

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Apple Should Buy Peloton

Note: I drafted most of this post a year ago. And it sat here as a draft all that time. I’ve made a few edits, but this is largely what I wrote then.

Despite have a massive cash hoarde and very competitive markets, Apple makes relatively few acquisitions. Most of those are small companies that have talent or technology that Apple wants to integrate into its existing and future products. Siri is a great example. The notable exception, of course, is Beats, which built a strong consumer brand and came with a hefty price. Still, you can make an argument that the Beats acquisition was as much about talent as anything, with Apple landing Jimmy Iovine, Dr. Dre, and a talented pool of entertainment executives.

I’m not one of those who thinks Apple should make acquisitions for the sake of making acquisitions. I’ve read many analysts who seem to think so. But I do think it makes sense to use some of the billions in cash they’ve amassed over the last several years to make acquisitions that make strategic sense. And I think Peloton is one of those. There are a few, key strategic reasons an Apple acquisition of Peloton makes sense to me. Here they are in no particular order.

  • Peloton has, in just a few short years, built a passionate, growing base of customers in the United States who exhibit the same kind of fervor over Peloton that Apple’s customers have for new iPhones, iPads and Mac computers. They serve as product evangelists, helping to recruit other customers, and are highly likely to continue paying the $39/month fee and upgrade to new equipment when there is a big enough leap forward (though not as often as customers of Apple devices do today). They are largely an affluent bunch. Such a solid core can be an important to any company looking to build long-term sustainability that can withstand the natural cycles of the marketplace.
  • The build quality and design of the Peloton equipment is excellent. They have prided themselves on creating an indoor bike trainer that is second-to-none it its fit and finish. Like Apple, they display a remarkable ability to combine aesthetic design with industrial design to create a highly functional product that is also beautiful to look at. Neither company looks to drive down price at the cost of product quality or the resulting customer experience.
  • The Peloton model fits Apple’s new emphasis on services to a T. The bike is expensive — $2,000 — but it may be sold at break-even or possibly a loss. The key to Peloton’s model is the $39 monthly household subscription fee that customers pay to access live spin classes streamed from Peloton’s New York Studio, or recording of those classes and scenic rides on demand. The $39 scales brilliantly around the world. It’s the equivalent of Apple’s family subscription services, like Apple Music.
  • Both companies are adept at pairing high quality hardware with solid digital content experiences. Peloton even created the equivalent of the popular “unboxing” drama of receiving a new Apple device, partnering with logistics companies to schedule delivery and having setup and testing handled before the delivery reps leave your house (though its not always perfect).
  • Apple’s Watch has evolved to be more narrowly focused on notifications and fitness tracking. Apple has Health, its default health-data tracking app, and HealthKit, an SDK for developers of health apps. And it
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iPhone 6S and Apple Watch

I’m really tempted to buy into AT&T Next or Apple’s pay-over-time program (likely the latter) to keep up my annual tradition of getting a new iPhone, repurposing my existing one for my wife, and selling hers on eBay for several hundred dollars. Neither my wife nor I are eligible for an upgrade just yet, but using Apple’s new purchase option means we’ll be off contract next year and can always choose carriers. I really want 3D Touch on my phone. It’s hard to wait…

It’s not so hard to wait on the Apple Watch. Don’t get me wrong. I really want one (with one or more bands). But I don’t love how it is so reliant on the iPhone, especially when it comes to fitness. I want to be able to run or workout with the watch on and tracking activity, and playing music to a set of wireless headphones. It seems to be to be totally against the fitness use case to need to carry your phone and headphones as well as the watch.

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The Collaboration Conundrum

There are lots of challenges in launching a startup. Raising money, hiring and leading a team, closing sales to grow revenue, having time to focus on the product you love… it’s not easy.

But finding the right collaboration tools for your team is essential, particularly if you’re dealing with a distributed workforce. And it may be among the toughest of challenges that entrepreneurs face. Why? There are so many damn options it becomes hard to choose. Some are great conceptually, not so much in execution. Some try to do to much, others not enough. Some are more creative solutions than others, but may be hard for some employees to grok.

My current startup is using Google for Email, Calendar, and (occasionally) Docs/Drive, but we mostly rely on Box.com for shared files. And we’re using Podio and GoToMeeting, both owned by Citrix, for team collaboration, web meetings and group video chat. We’ve created custom apps on Podio for sales/CRM, marketing, and product development, as well as for each client we have. Polio is integrated with GTM for video meetings, with Box for attaching files to conversations, and with Gmail and Calendar to turn emails into tasks and show tasks on the calendar. And the list of integrations goes on and on. In theory, it seems like a good solution. In theory.

The reality is that we deal with hassles all the time. GTM has pushed several updates this year, and there have been enough bugs to cause some real inconveniences. Plus they don’t seem to handle low-bandwidth situations for audio and video as well as they once did. Podio has some great features, but it’s core task functionality is flawed in how it relates to custom apps and their fields. While I love Gmail, some team members come from a corporate background and struggle with Gmail’s user interface, pining for Outlook. And Box Sync for Mac is incredibly slow, even for some of the smallest of files.

We’ve looked at changing things up before we start to accelerate our growth. I’d really like a goal-driven collaboration platform like Workboard, but just haven’t seen enough value to pull the trigger. We’ll need a true CRM before too long, and I’ve toyed with migrating from Gmail to hosted Exchange, but Outlook for Mac 2016 has been really buggy in my limited trial. We haven’t yet integrated expense management like Expensify, or HR management like Benefits, so we’re just scratching the surface. In any case, we’re likely to need multiple solutions, which means multiple logins, learning curves and invoices.

I would love for someone to solve this problem, so I can focus on growing my company.

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Welcome to Essential Cog

Essential Cog is produced by Patrick Hunt, a software company CEO, and is focused on startup life, technology, and Apple.

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