GMAIL, Facebook, Twitter and Lastpass have all had serious hacks in the past couple of years. I think the in vogue status symbol in the next couple of years will be to create your own cloud service in your closet and back it up to the cloud encrypted.
There might be a cool startup there: home cloud systems that leverage redundant broadband connections (dsl + cable + fios) in your home that are harder to hack. They would be harder to hack because they are not part of the tareted BigCos right?
anyway, just an idea... "google docs server for home"
Not neccessarily. A lot of totally unknown installs get hacked all the time (cf. random WP blogs) by script kiddies who scan thousands of adresses trying to find a few to get into. They don't care you're not a BigCo and that your server is in your basement.
And if you're taking care of that server yourself (and assuming you do have other things to do in your life), you're likely to miss some security upgrade, and might leave a hole open just enough for someone to accidentially stumble into.
I presume having the server only accessible through a VPN, and configuring all your devices (laptops, tablets, phones) might do the trick, but that's a bit pushing it.
Correct but the issue to me is not "what can the neighborhood general store do themselves". It's wcfwd - what could Fred Wilson do. Fred doesn't have to fly coach (although he does fly coach apparently).
I agree with the other comments that you are less of a target in general also depending on where your docs are located (or where your server is colocated even if it's your house).
Fred is going for the low hanging fruit solution to a problem. Not necessarily the best solution.