It’s like a vanity license plate for your website. Normally I glance over short-links without thinking nothing of them, but I came across a tweet by @destroytoday with the url dstry.it and BOOM the brand was burned into my head. Although having a bad ass business name helps too. I also like that a personalized short-link gives the user a bit of confidence it’s safe to click. The hardest part to setting up a custom link system is registering a relevant domain. Two characters is almost impossible and not allowed by some top-level domains. If you’re lucky you can find a clever three or four character domain that bleeds into the TLD so it’s easy to remember and recognize.
The easiest part is setting up the domain with bitly. While there are some free products like yourls that allow you to host your own service, they take a little more work to setup.
Finally, if you use WordPress there a lot of nice plugins to make the process even easier. My personal favorite is bit.ly shortlink by Yoast.