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Payment Challenges and Fixes for Today's Entrepreneurs Next time, the client says "The check is in the mail," don't be so complacent.

By Tina Hsiao Edited by Frances Dodds

Opinions expressed by Entrepreneur contributors are their own.


You've delivered that big new client project. Hooray! Yet before you can pronounce the project truly done, you need to get paid. And the client that had been corresponding with you with great urgency is now saying that the invoice needs to work its way through Accounting.

Related: Why Payment Processors Suspend Their Legitimate-but-High Risk Merchants

What's more, the approver is on vacation and won't be back next week. So, the check will be "in the mail." So, while that will likely happen . . . for now, you need to wait.

Painful. And common, according to new national research highlighting the challenges many entrepreneurs know well when it comes to managing cash and getting paid for their work. The WePay SMB & Money Survey shows that 41 percent of U.S. small businesses surveyed reported having experienced cash-flow challenges, and 16 percent had experienced payment fraud -- just in the past year.

What's more, many entrepreneurs say they've dealt with multiple instances of customer payment fraud, with 8 percent of those affected reporting 10 or more instances, and more than half saying their first brush with payment fraud came within two years of starting their business.

More survey findings of note:

  • 25 percent had experienced a chargeback (a fraudulent or disputed transaction that resulted in a financial institution requiring the business to make good on the loss) in the last year
  • 33 percent said they usually get paid immediately (often for goods sold in-person), while the majority said they were left playing a delicate waiting and reminding game to get paid
  • 10 percent had had to chase down a customer payment for 181 days or longer

Related: How to Get Clients to Pay You Upfront

What's an entrepreneur to do when they're passionate about what they do and yet don't want to let payments challenges dull that passion or take a huge amount of time ongoing? Here are five lessons we've learned at our company after helping millions of merchants process payments on more than 1,000 online platforms:

1. Align expectations up-front.

When you take on a new client or project, it pays (pun intended) to invest the time getting clear on details of the deliverable's timing, and payment timing. Going one step further, capture it in an estimate or invoice. The extra effort will go a long way in ensuring there's no disputed charge later, nor any surprise, like your expecting to be paid immediately upon service delivery while your client is planning to pay later.

2. Dispute unexpected charges.

We've come to see many entrepreneurs take the hit and move on. And we appreciate that this may be the path of least resistance on smaller transactions. Yet you can fight and win a chargeback claim. Step one should be to engage your customer directly to clear up any confusion. It may help to remind this person of your return policy, restocking fees and/or terms of service. You can also dispute through the bank, presenting documentation that includes signed contracts or receipts, relevant emails and screenshots of shipment tracking.

3. Open yourself up to additional payment methods.

Many entrepreneurs refuse to accept credit cards or even ACH, given the fees. None of us like added cost. Yet holistically, we've come to find that allowing customers to pay with their preferred payment method increases customer conversion.

And if you can help them to pay you immediately, better still. Also, if you assign value to not having to chase down and wait on payments, added fees can very well be ROI positive.

4. Use a platform with integrated payments.

WePay's survey found that those SMBs that process all of their customer payments inside their go-to management software platform or app -- like a Shopify, Zoho or BuilderTREND -- report a 15 percent lower incidence of cash flow management issues. This finding fits with our broader experience that software with integrated payments can make it much easier for clients to pay you immediately… and it's inside something you're already using. Some of the best platforms offer extensive risk and fraud protections. They can additionally give you access to new customer-friendly payment options like Apple Pay or Android Pay.

Related: 5 Ways to Avoid Cash-Flow Log Jams

5. Be skeptical when it's too good to be true.

Because entrepreneurs do more business online, they're increasingly falling victim to fraud that only becomes apparent at the time of payment. Don't be scared -- be prepared: Seek more information and assurance if you see warning signs like a high value rush order from a new client, a person overseas wanting to work with your local business from afar or someone suggesting you pay their subcontractor from a lump sum they will pay you.

Tina Hsiao

Vice President of Risk Chargeback Operations, WePay

Tina Hsiao is vice president of Risk and Chargeback Operations at WePay, company that helps online platforms provide integrated-payments processing without friction or fraud. She is also a Harvard Business School MBA who spent more than 10 years in Intuit’s small business division.

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