When you use Venmo, you're not actually sending money from your bank or credit card to your friend. In a normal Venmo transaction, the money is removed from your bank but remains in their Venmo account until they manually move it over into their bank or onto a credit card.
This means for those who forget to move the money over, it's as if that person never received the money at all. You have to manually remember to transfer your Venmo funds to your bank.
This is especially problematic for people like me, who only use the app occasionally, and might not check their Venmo balance for weeks at a time. For example, when I opened my Venmo app in preparation for writing this story, I found that I had $68.18 sitting in my account, built up from various outings with friends.
I'll admit the experience of finding unexpected money was nice, but not having any kind of direction or reminder from Venmo to transfer my money, and having it just sit there for weeks, is far from ideal.