Gus Mueller outlines some excellent benchmarks for when we’ll know Apple has taken the next serious step with iCloud:

WWDC 2013 is fast approaching, and chances are good that we’ll get some sort of preview and song and dance about how iCloud sync is even better than ever for developers. Honestly, would you expect Apple to say anything else?

But how are we going to know Apple has finally fixed iCloud syncing for developers and is really serious this time?

I still believe that many of Apple’s most exciting and ambitious plans for the future are centered around iCloud and Siri.

No doubt we’ll get a preview and song and dance about new functionality in Siri as well. But how will we know Apple has moved Siri beyond a way for hands-free texting and event creation and into something iPhone owners have just got to have?

I think of three significant benchmarks that will signal a more serious move for Apple regarding the future of Siri:

• The first is a public API so 3rd-party apps can tie into Siri just like the calendar and text messaging apps already do. For example: imagine asking Siri to create a new OmniFocus task and setting the project, context, start, and due dates without ever being launched into OmniFocus?

• Second, tying in the credit card we have associated with our Apple ID and using that to purchase things like movie tickets, plane tickets, and more. Looking up movie times is neat, but then being sent to the Fandango app to actually purchase them is less than magical.

• Lastly, bring Siri to the Mac. Show that it’s not just for hands-free text messaging anymore.

As Kyle Baxter wrote last year:

If you want to know whether Apple’s going to continue its remarkable growth in the next five or more years, there’s two things you need to look at: Siri and iCloud.

iCloud is the glue that ties all our devices together. Siri is Apple’s 4th interface. But so far, these massively significant services are still mostly hanging out quietly in the background.

Igloo has some funny new Sandwich videos to lighten your day (and maybe convince your boss and/or IT to upgrade your intranet to something more human). Check them out:

• Intranet
• Updates
• Versions

(You can also get a free 30-day trial and bring back Cake Fridays here.)

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My thanks to Igloo Software for again sponsoring the site this week. Sponsorship by The Syndicate.

Andrew Sullivan on the current state of The Dish fundraising:

I’ve even decided not to take a salary this year at all in order to invest in the Dish itself and keep it afloat. We’re still chugging along steadily in revenue, and we are brainstorming about new sources of income (stay tuned), but it remains unlikely that we will reach our target of $900,000 by the end of the year, even though we have already brought in gross revenue of around $680,000 – three-quarters of the way there.

Sullivan taking The Dish to a completely reader-supported business model created a huge wave of attention from other media outlets, as well as hope from other publishers (both indies and bigger media sites). In many of the shows I’ve listened to and articles I’ve read over the past few months that discuss the future of publishing, Sullivan’s leap with The Dish has been one of the central examples. If he can’t make it then that stinks.

We’re still in the beginning of this era where content creators and artists have a genuine fighting chance to be wholly fan-supported. And while it’s easier than ever, it’s still not easy.

When Ben Brooks eschewed all his ads and went wholly reader-supported, he ended up taking a hit in his site’s overall revenue — dropping from $2,100/month in ad revenue to $1,000/month in member support.

When I took this site full time two years ago, my business model was (and still is) to have the membership exist alongside the advertising revenue — I need both streams to make it work.

And it looks like The Dish also needs to find other revenue streams in addition to their subscription paywall in order to meet their goal of $900,000/year.

Coming back to the aforelilnked On The Media podcast: “There is no silver bullet. There is only experimentation, determination, and a whole lot of blind hope.”

I’m almost as nerdy and fussy about grilling and smoking as I am about making coffee. I’m just not as vocal about it. Well, until now…

This Tools & Toys guide was written by yours truly, and it’s a doozy. As I say in the article, one of my great joys of summer is getting up early while the air is still crisp, brewing a cup of coffee, walking into the backyard, and starting up a chimney full of charcoal for a day of slow-cooking some smoked BBQ.

I especially enjoyed this week’s episode of On The Media if only because it hit very close to home. The show was dedicated to “the incredible volume of media available to consumers, and the incredible difficulty of making money for creators.”

The six different segments cover streaming services, subscription business models, ads and ad blockers, and direct support from readers. The business examples were all with big-name media networks and websites, but the struggles they’re facing are no different than what guys like you and me are facing: how do we keep the lights on so we can keep making awesome stuff for our best fans?

For me, it’s a conglomerate of all sorts of things. The largest and most-significant slice being the monthly membership to this site, but the rest of the pie is a combination of advertising and affiliate links.

At the end of the show, Bob Garfield concludes with this line:

There is no silver bullet. […] All there is is experimentation, determination, and a whole lot of blind hope.

Which parallels something Merlin Mann said in his interview on CMD+SPACE a while back: “As long as you keep putting out interesting stuff, you’ll keep discovering interesting stuff to put out. It’s an iterative and ugly process.

As an indie writer, I’ve always put a lot of emphasis on the determination aspect — show up every day — but very little emphasis on the experimentation aspect. For me, my daily podcast ended up being an excellent members-only perk for when I took the site full time, and as I look at the shows I’ve done over the past 2 years and the feedback I’ve received from listeners, I mean it when I say the show has become one of my favorite things where I see a lot of my best work manifesting.

I can think of two other excellent examples of experimentation that made a way for revenue: John Gruber’s wild idea of an RSS ad sponsorship, and Marco’s wild idea of a very simple, very classy digital magazine.

At the end of the day we all just want to pay our bills, feed our families, put our kids through college, and keep the office lights on so we can keep on making things.

Though I wasn’t there when Marco decided to make The Magazine, nor when Gruber decided to start selling RSS sponsorships instead of a membership, nor when so many other folks took a leap to try something new. But I imagine the internal dialog was something along the lines of: “Maybe this will work, maybe it won’t. I guess we’ll find out…”

Mad Mimi is a design-oriented email newsletter service founded in 2008. Developed to provide a mobile-app-like feel, and with a drag-and-drop email composer, Mad Mimi offers a simple, elegant user experience that helps customers create, send, and track beautiful html email campaigns.

Mad Mimi also offers robust APIs, integrations, and add-on features. This makes it a perfect fit for today’s visionaries, artists, and entrepreneurs, including great digital brands like Fancy and StumbleUpon, who use Mad Mimi to communicate with their customers.

Best yet, Mad Mimi is free for up to 2,500 contacts. We hope you’ll give us a try or email us with questions.

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My thanks to Mad Mimi for sponsoring the RSS feed this week. Sponsorship by The Syndicate.

Federico Viticci’s got a killer list of ideas and wishes.

Fraser Speirs on some of the frustration points getting in the way of making our iPhones and iPads a bit more “power-user friendly”. As someone who uses his iPad as his “laptop”, I too encounter many of these frustrations on a regular basis. Particularly the issue of moving data and documents between apps and how there isn’t really a good way to send or open a file in one app to another. In part, I think this friction point is one of the reasons writers seem to be among the forerunning professionals who are using the iPad as a legitimate work device. Because the files we deal with are often no more than text. And so “moving a file” from one app to another can be as easy as selecting all, copy, paste. Not everyone who wishes to do more work on their iPad has it so easy.

Here’s your daily dose of nerdery.

Harrison Weber:

Adobe is abandoning its Creative Suite entirely to focus efforts on Creative Cloud.

CS6 will still be available for sale, but otherwise if you want the newest software it’ll only be available through subscription. $50/month for the whole suite or $20/month for single apps.

I’m still using CS3 (Photoshop and InDesign mostly), and as long as they still still work on my Mac then I have no motivation to upgrade. Heck, I’d probably still be on CS1 if I hadn’t been forced to update after the switch to Intel.

Dropzone is a pretty rad Mac utility that lets you upload files to your FTP server, Amazon S3, Flickr account, and other places via drag-and-drop targets.

Per Stephen Hackett’s recommendation, I gave the app a trial a while back but never stuck with it because my most-used upload location is my Amazon S3 Bucket where I use a folder hierarchy for my different websites and podcast. At the time Dropzone only supported uploading to an S3 Bucket’s root, which meant I couldn’t upload to my different folders. But with Dropzone 2.6 that just came out, that is no longer the case.

The advantage of using Dropzone over Transmit Droplets is that Dropzone doesn’t require the launching and then quitting of Transmit to upload a single file. Also, after uploading a file through Dropzone the file’s URL is copied to your clipboard. With Transmit Droplets, the app closes as soon as the file is uploaded and you’re left without knowing what the URL is.

For the nerdy readers, you could build your own version of Dropzone using Hazel and Gabe’s Python scripts for Amazon and FTP. That’s what I did to automate my Shawn Today uploads, but I’m not going to pretend I didn’t have a heck of a time getting it to work. Dropzone is much easier to set up for the non nerdy, and it has some handy interface elements that make it easy to use for non-automated purposes.

Dropzone is $10 on the Mac App Store, or you can download a free trial version from the website.

PDFpenPro is the advanced version of PDFpen. PDFpenPro does everything that PDFpen does, such as add signatures, edit text and images, perform OCR on scanned documents and export Microsoft Word documents. It also has the ability to create a PDF form, build a table of contents, and convert HTML files to PDF.

The new PDFpenPro 6 adds document permission settings. When you share a PDF, you can restrict printing, copying, and editing of your PDFs. You can also use the new automatic form field creation tool to convert a non-interactive form into an interactive PDF form with text fields and checkboxes automatically added.

PDFpenPro 6 is available on the Smile Store and the Mac App Store for $100. A free demo can be downloaded on the Smile site. Find out why Macworld calls PDFpenPro “the crème de la crème of PDF editing and annotating applications.”

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My thanks to Smile Software for sponsoring the RSS feed this week. I personally use PDFpenPro whenever I need to annotate, fill in, edit, or redact something in a PDF.

Sponsorship by The Syndicate.

Right in line with some of this week’s aforelinked articles on simplifying is this fantastic TEDx talk by Chris Sauvé. I love the Gustave Flaubert quote he kicks off his talk with: “Be boring and orderly in your life, so that you may be violent and original in your work.”