Dropbox: Sharing files and folders

by Jesse Lahey on May 17, 2012

DropboxThis is a Man-Cave Certified productivity app. Geeky, yes, but it saves me at least an hour every week, so I can use the time to focus on my priorities.

This resource is free for 5 GB (recently increased from 2GB in response to Google Drive!). Each time you refer a friend, they give you even more free space. I was able to refer so many friends, that I quickly climbed up to 5 GB in free space. However, Aspendale Communications’ team members liked it so much that I ended up paying for a team subscription so that we now share 1TB.

This service “just works,” especially when you use its desktop syncing software. Here is what I like about it:

  • When I want to share a file, I just drag it to the appropriate folder or sub-folder.
  • I can assign exactly which people should have access to any given folder.
  • Even when my Internet connection spotty or somewhat slow, the files upload and download fairly quickly.
  • If I make a minor change to a file, or change the filename or location, it doesn’t waste time and bandwidth uploading the entire file … it only syncs the new/changed data.
  • It works on both Mac and Windows.
  • The iPhone and iPad apps rock, providing instant access to all my files.
  • Doubles as off-site backup of my files. In addition to an external hard drive that I use in combination with Time Machine for hourly onsite backups, I used to create a DVD backup once a quarter so that I could keep an off-site backup in the event of some catastrophe at my office. With DropBox, I now have a constantly updated off-site backup. (I used Carbonite for a couple of years, but it was buggy and periodically required re-installs. DropBox has been trouble-free and offers much more functionality than just backup.)
  • You can provide someone with a “shareable link” so they can download a file, even if they don’t have a Dropbox account. (However, for frequent sharing, it’s simpler if both people have Dropbox accounts because you can both add files to shared folders.)
  • In Finder or Windows, I can use aliases to integrate the Dropbox folders into my natural filing system. (For example, see the screen capture of my 2012 Projects folder.)


I’ve tried others, such as Box (formerly known as and iCloud. Box had lots of great features and boasted a higher level of security, but the syncing feature for Mac was not a fully mature offering when I tried it — it was noticeably slower than Dropbox. And I just don’t understand iCloud … it’s not a true file-syncing service like Dropbox; it seems like an overly complicated way to keep Apple-based devices synced with each other.

DropBox “just works” — it’s easy, it’s intuitive, it makes for easy sharing on a team, and it allows you to create a link to share any file with others (including people without DropBox).


Here is a comment on an earlier draft of this post, provided by the Podcast Answerman, Cliff Ravenscraft:

I could not agree more, Jesse!  Because of the number of people I referred, I had grown to 11.6GB in my free account.  I went ahead and upgraded to a 50GB account which means I now have 61.8GB of space.

DropBox has transformed my computing experience.  Because I have the same software on my MacBook Air that I have on my desktop, I can leave my studio and work form anywhere in the world and have access to “almost” everything.



ShoeBoxed: Receipt/document scanning and filing

by Jesse Lahey on May 5, 2012

This is a Man-Cave Certified productivity app. Geeky, yes, but it probably saves me an hour per week, so I can use the time to focus on my priorities.

ShoeBoxed is so easy … it’s like Netflix + Google for your receipts, paper documents, and business cards. It has saved me a lot of time, frustration, and storage space.

Before ShoeBoxed

Before ShoeBoxed, I had to meticulously file away all my receipts into specific folders … and even then, when I needed an old receipt, there was only a 50% chance that I’d actually find it. (I repeatedly complained to my wife about batting only .500 every time we needed to find an old receipt.) It took at least five minutes, and often 15-30 minutes, to find old receipts.

Also, at the end of every year, I had a huge accordion file that needed to be stored away.

After ShoeBoxed

Now, I spend no work filing … I simply throw my receipts into the blue, postage-paid “Magic Envelope.” About twice a month, I drop the full envelope in the mail. In about 10 days, the scanned receipts are available online (note this is NOT as fast as they promise, but it’s OK with me). Now, I can find about 97% of my receipts (the other 3% probably get lost before I make it home).

I always find them within 5 minutes (usually much less), using my desktop computer or my iPhone.

Now, I only store away a slim accordion file of certain receipts and statements that for whatever reason I haven’t chosen to send to ShoeBoxed. I keep seven years worth of hard-copy receipts, so after two years with ShoeBoxed, I have already freed up a medium-size shelf. For the first year, I was nervous about ShoeBoxed, so I chose the option of having them send all my hard-copy receipts back to me after scanning. Now, I let them shred the hard copies so I can be virtually paper-free.

ShoeBoxed also offers the ability to export into QuickBooks and Freshbooks, which are software that we use for Aspendale Communications, but that has never seemed important to me. Perhaps smaller businesses would find it useful, for example if ALL of their expenses were run through ShoeBoxed, but we have so many other transactions that we prefer to just import transactions from our credit union.

Searching and Archiving

For the first year or two that I used ShoeBox, their search functionality wasn’t great, so I periodically exported my receipts from ShoeBoxed into Evernote.

However, ShoeBoxed has recently improved their search engine, and now it rocks! I don’t even bother with tagging receipts. Similar to using Google, I just enter the store name or any other word that was on the receipt, and ShoeBox pulls up all the matching receipts. It’s amazing to me that their scanning software automatically picks up words like the name of the store/business and products/services.

I think I will continue export them into Evernote, as an archive in case something happens to ShoeBoxed. But their new search engine has been sure-fire in getting me to the right receipt very quickly.


Check out their plans and pricing. I started out with the Lite plan (currently about $10/month), but with all my business receipts and documents, I eventually settled in with the Classic plan (currently about $30/month).

I compared the cost with NeatDesk, but that hardware is expensive enough that it wasn’t worth the time saved by letting ShoeBoxed do the scanning and tagging.

The receipt-scanning alone is worth it, but I also take advantage of the business-card scanning and the document-scanning (no extra cost).


Have you used ShoeBoxed, NeatDesk, or anything similar? If so, what’s been your experience?