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Pioneer Blog

Best Ways to Send Money to your Family and Friends

Posted on May 30, 2019

Back in the day, there were only two ways you could send money to your family and friends, cash and writing a check. Thanks to our rapidly changing world, and the digital state of currency, there are a whole host of new ways you can move money around. Whether you need to pay a debt to a friend, pay your share of your family plan cell phone bill, or get your child at college some money quick, here are the best ways to send money.

You Can Always Send a Check

man writing with a pen at a deskSometimes, a classic solution is one of the easiest. Sending a check in the mail is easy to do and is fairly secure. If your check doesn’t arrive at its destination, you cancel it. If it does, then you’re all good!

The biggest downside though is that sending a check takes time, and you need to make sure to keep enough money in your checking account to cover it until it clears. That could mean worrying about it for a few days to even a few weeks, depending on how long it takes the recipient to receive and deposit the check.

Utilizing Bill Pay for One Time or Recurring Payments

Maybe you’re on a family cell phone plan or split a streaming subscription with a friend and need to make regular payments to them. Pioneer’s bill pay is a great resource to make sure that money gets sent every single month so you don’t have to have an awkward conversation about forgetting to pay later. You can even use it if it’s just a one-time payment or if you need to adjust the amount month-to-month.

By setting up bill pay, you can schedule out payments ahead of time and identify recurring payments to go out every month. Plus, it’s completely free for Pioneer members! Your recipient will get a check in the mail after a day or two and you’re all finished.

Sending Money Through PayPal

young woman listening to music with earbuds and smiling at her smart phoneOne of the largest online money systems, PayPal has been helping people make purchases and transfer money securely since the late 90’s. Because it has been around so long, most people know about PayPal and feel secure in using it.

The upsides to PayPal include a quick money transfer experience and is relatively easy to do. All you have to do is enter the recipient's mobile phone number or email address and how much money you are sending, and you are done! Plus, if you have your bank information attached to your PayPal, it’s free to transfer money for non-business reasons.

The downsides of PayPal mostly happen if you don’t have your bank attached to your PayPal. If you use a debit or credit card to send money through PayPal, you’ll be charged a 2.9 percent fee for the transfer.

Using a 3rd Party Service

There are a wide variety of services that let you send money to others. Each has their own pros and cons, so we’ve compiled a few of the most popular ones for you.

Square Cash

five people of different backgrounds all looking at their smartphonesSquare Cash is a free and easy to use service for sending money to peers. All you have to do is ask for the person’s “Cashtag” URL and then visit their page to transfer the money. Even if you don’t have a Square Cash account, you can still visit the Cashtag URL and make a payment through other means, including debit and credit cards.

The only downside to Square Cash is there is a $250 per day limit on transfers unless you verify your identity, in which case increases the limit to $2,500 per day in most states.


Venmo is an app and website transfer service owned by PayPal. Similarly to PayPal, it’s free to transfer money if the money is funded through your bank or from money you’ve received from others, but will charge you a fee if you fund the money from a credit card. Venmo also a weekly limit, $299.99 a week for unverified users, and $4,999.99 for verified users. That limit includes both sending and receiving money.

Facebook Messenger

It’s not just useful for sending messages and articles to your friends, you can also transfer money with it too! It’s free and all you have to do is open up a chat, click the dollar sign symbol and put in your debit card information. Then, the receiver needs to accept the transfer by putting their debit card info in, and you’re done.

The only downside is the security of your Facebook account itself. Once you’ve put a debit card on Facebook, it stores it for you. You can (and should) add a pin to your Messenger to stop unauthorized money transactions in case your account does get hacked.


Pioneer members can send money using Popmoney by either logging into myPioneer and registering there, or by signing up on the Popmoney website/app. If you sign up through your Pioneer account, sending and receiving money is free, though requesting money from others might result in a small fee.

If you want to register for Popmoney, sign into your myPioneer account, click on Move Money, select the Pay Other People (Popmoney) option and follow the directions there!

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