Use Apple Mail + Gmail? You’re about to lose emails.

30 days after you start using Apple’s Mail app version 7 on Mavericks with your Gmail account you’re going to start losing emails.

Let me explain.

Google’s recommended IMAP client settings tell Apple Mail users to leave unchecked the “Move deleted messages to the Trash mailbox” option (in Preferences > Accounts > Mailbox Behaviors). Why? Gmail users expect “deleted” messages to be archived, not deleted. Emails marked as Trash, however, are deleted by Gmail after 30 days.

Prior to Apple Mail 7—the one that comes with Mavericks—it was possible to follow Google’s recommend client settings to make everything work as a Gmail user would expect.

The problem is, with Apple Mail 7, it seems to be impossible to uncheck to the “Move deleted messages to the Trash folder” option in Mail > Preferences > Accounts > Mailbox Behaviors.

Mailbox Behaviors

As a result, when you delete a message, Apple Mail gives it the Trash label and Gmail deletes it 30 days later. Note that the “Permanently erase deleted messages when” option applies to Apple Mail’s behavior, not Gmail’s behavior.

What’s alarming is this: I had my IMAP settings correctly configured according to Google’s recommendations with the previous version of Apple Mail and upgrading to Mavericks silently changed the settings.

Without warning, Apple Mail started marking my deleted messages as Trash, setting them up to be reaped by Gmail after 30 days!

Fortunately for me, an entirely unrelated and repeatable data-loss bug in Apple Mail 7 forced me to go digging into my Gmail account via the Gmail web interface this evening. That’s when I discovered things in the trash that I didn’t expect to be there. Since I’ve been less than 30 days on Mavericks, I didn’t lose any email and was able to remove the Trash label. I got lucky. (The unrelated data-loss bug, while horrendous, is something that most people are unlikely to stumble upon so I’m not raising the alarm on it. I have reported it to Apple.)

Long story short, if you use the new Apple Mail + Gmail then the clock is ticking on emails that you’d never expect to be permanently deleted.

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Don’t Hurry. Focus on Now.

In human affairs of danger and delicacy successful completion is sharply limited by hurry. So often men trip by being in a rush. If one were properly to perform a difficult and subtle act, he should first inspect the end to be achieved and then, once he had accepted the end as desirable, he should forget it completely and concentrate solely on the means. By this method he would not be moved to false action by anxiety or hurry or fear. Very few people learn this.

– John Steinbeck (East of Eden. ch. 21, para. 1)

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Be Your Customer’s Tour Guide.

Your job is to be your customer’s tour guide through the unforgiving terrain of the information technology world. You will make your customers comfortable while guiding them through an unfamiliar place. You will show them the sights and take them where they want to go while avoiding the seedy parts of town that you’ve encountered in the past.

– Chad Fowler, The Passionate Programmer, 2nd Edition, pp. 136-137.

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Boulder Rocks

Back in 2011, Jen and I decided to move to Boulder to start a new company. We did. And then, even though we resisted it until the last minute, we got into TechStars. Things got busy from there. Thanks for your patience.

Over the past year I’ve been collecting a pile of things I’d like to blog about. More soon.

Right now I’m going to do some coding at The Cup before this morning’s meditation at Dojo4. Yes, we sometimes meditate before work here in Boulder. We also sometimes work our assess off doing things like TechStars.  And it snowing something beautiful right now.

Rock on.

The Cup. Boulder, CO.

The Cup. Boulder, CO.

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Notes on the Innovator’s Patent Agreement

I asked a patent attorney friend of mine (who asked to remain anonymous) to read over the Innovator’s Patent Agreement and comment on it. It’s obviously a moving target, but here are his initial thoughts on the draft that was circulating yesterday:

It sounds like an idea worth exploring.  I’m not so wild about some of the language though.

For example, section 2 defines what “defensive” uses of the patent are.  Section 2(b) considers enforcing a patent “defensive” if it is asserted against anyone who has “filed, maintained, or voluntarily participated in lawsuit against another in the past ten years,” unless that lawsuit itself was defensive.  There’s a leak there:  it lets in any defendant in a patent litigation.

In other words, suppose Twitter is sued by a patent troll, defends itself, and wins.  It arguably “voluntarily participated in a lawsuit against another,” albeit as a defendant.  So under the agreement, Twitter is a fair target for any patent under this license.

Also, the “in the past ten years” language of section 2(b) isn’t clear whether “past” is measured as of the execution of the agreement, or as of the time of filing the lawsuit.

There’s at least arguably another technical problem with the clause: “If Assignee needs to assert any of the Patent claims against any entity for other than a Defensive Purpose, Assignees must obtain prior written permission from all of the Inventors without additional consideration or threat.” 

Continuing on, section 2(c) allows an assignee to use a patent to:

“(c) otherwise to deter a patent litigation threat against Assignee or Assignee’s users, affiliates, customers, suppliers, or distributors.”

That can potentially be pretty broad.  For example, I’m a mid-sized Twitter licensee.  I’m approached by a small company, and they show me their awesome new patent that I might infringe… or at least one day I might infringe it, as soon as I launch my in-the-works product that the small company doesn’t know about.  The small company wants to partner up with me and develop a product a lot like our in-the-works product.  I offer to buy their patent, which they reject.  Lo and behold, the small company also arguably (!) infringes one of my Twitter-licensed patents, so I decide to apply some pressure in the negotiations by starting a lawsuit under that patent.

The idea behind that lawsuit is to “deter a patent litigation”:  if I launch my product, they might come after me with their patent.  But I can’t afford their patent as it is, so I need to acquire it.  A great way to do that is to crush them in litigation.

Of course, I get the idea that they’re trying to go after in paragraph (c) there.  But their words are a little too permissive, I think.

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Common Themes on AngelList

Back in June of this year, in a galaxy far far away (OK.. we were in Phoenix, AZ at the time… but compared to Boulder, CO…) — Jen reviewed all of the companies on AngelList to get a feel for what was going on out there.

Here are the common themes that she found across many of those companies:


  • No additional infrastructure or IT platforms needed (e.g., paying retail with smart phone, consolidating rewards programs, invoicing early at deeply discounted rates, etc.)
  • Phones becoming something else (e.g., microscope; a cyclist’s tool (map, odometer, etc.))
  • Companies describing themselves in relation to other companies (e.g., it’s like Etsy or Uber but for food, or Netflix for underwear) 
  • Making things sound exclusive
  • Companies offering ways to better understand & harness social media
  • Photo sharing apps and websites abound
  • Many point of sale innovations, making purchasing easier/quicker
  • LOTS of companies harnessing social media to drive sales
  • Many companies focused on location based deals and social networking 
  • Many e-commerce sites (for fashion primarily) 


My two cents: While those all may be fine things, the only one of those things that sounds interesting to me is “phones becoming something else.” 


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Boulder, we’ll be back. Soon.

Long story short, Jen and I are moving to Boulder, immediately — just as soon as we can find an apartment. And we’re looking every day (via  PadMapper, Trulia, etc.)

Highlights from our recent visit:

  • Attended both nights of NewTech (Boulder Denver) TechStars presentations. Thanks to everyone who presented — you rock!
  • Attended a Boulder Open Coffee Club meetup — un-f’ing-believably great energy in that room. Seriously, if you ever get a chance, drop in and feel the power.
  • Co-worked at Trada CodeSpace for a few hours (thanks to @angilly whom I met at the BOCC and who pointed me to CodeSpace).
  • Visited every startup-friendly coffee house mentioned on Quora — worked in the ones where we could get a seat.
  • Met new friends. Had dinner with new friends. Reconnected with old friends. Enjoyed some fantastic beer.

Also took drives West into the mountains / wilderness / national parks. Also took a drive south through the mountains to Evergreen.

I don’t have the words to describe how beautiful some of the mountain areas in Colorado are. But here’s a photo — and keep in mind, the only thing I know about photos is point-my-iPhone-and-shoot.


Stay tuned! Have fun!

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