This reasoning reminds me a bit of Umesh Vazirani -- "If you’ve never missed a flight, you’re spending too much time in airports."

If your stuff has never been stolen, you're spending too much time/effort/money guarding it.

So if I'm in a coffee shop with a laptop, and I think I'll have to hunt around for a seat if I give mine up, I'll ask someone to watch my laptop. It's way less than $5k in value, but it's also both easier to steal and more obviously worth stealing.