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Yes I have. Venmo charges 3% fee on the transactions. That said it is a great way to manufacture some spend for sign-up bonuses on Chase. I am currently paying rent with SW Cards because I opened both at the same time and need $5k spend for 110k total miles and free companion pass for wife.
It is worth it for signup bonuses and convenience, but otherwise the costs outweigh benefits.
Unless you have Alliant Cashback visa in which costs are equal to venefits
^D1 - How did you get two SW cards at a time?
@P1, you can open a business card as well as a personal card simultaneously. Business card can be registered to sole proprietorship (your name), and you can connect signup rewards from both cards to accumulate in the same rapid rewards account to take advantage of both. Business card rewards 60k points after minimum spend of $3k, personal card is 50k points after same requirement for total of 110k points, which is the requirement to receive SW companion pass.
It’s interesting you ask, because yesterday they changed the policy and strictly prohibited new customers from opening more than one personal credit card. This does not apply to business cards + credit cards.
I do it for the convenience. It's one less thing for me to worry about, literally the only check I write (I use Plastiq). I put it on my Delta Reserve to work toward annual 30k spend for 15k MQM bonus and depending on the year, platinum MQD waiver (not needed this year). Can do the same with a Delta Platinum card too but I'll take whatever advantage I can get for upgrades.