“The Points Mom,” From Westchester, Says For Free Travel, Avoid CC Rewards Errors

Cindy Greenstein, with husband Robert in Laguna Beach, California

By the time most families step off planes for vacations, they’ve spent thousands of dollars getting to their destinations—but not Cindy Greenstein.


As The Points Mom, the Chappaqua-based mother of three has turned her dexterity with credit card reward programs into a small business advising neighbors and small business owners on how to reap the biggest rewards using the right cards. At the same time, she has earned hundreds of thousands of dollars in free travel for her family.


“Every month, I counsel credit card users who missed out on significant free travel and benefits because they made simple, avoidable errors,” said Greenstein, who began The Points Mom consulting four years ago. “These errors fall into several categories, and they are easily avoidable with a bit of planning and awareness.”


One of the most common errors Greenstein sees is a failure to hit a minimum charge amount within a given period, say $6,000 within the first three months of sign-up. Failing to hit that minimum spend means a credit card can cancel a 50,000-point sign-up bonus, which negates the reason for applying for that card.


“Credit card users might think the card’s annual fee counts towards the minimum spend—it doesn’t. If you charged $500 on a new coat and then return it for a refund, then that $500 doesn’t count either,” said Greenstein, whose free, five-figure family trips include Aspen, Greece and London.


Another mistake is redeeming points on Amazon. “It looks appealing, but you’re not getting one cent per point, often you’re getting 0.7 cents and we want at least one cent per point or mile redemption,” said Greenstein, whose favorite cards are the Chase Sapphire Preferred, Capital One Venture X and Amex Gold Card.


Making a reservation without comparing ticket-redemption costs is a mistake. For example, a $500 ticket on Delta might cost 50,000 American Express points, but on the Delta rewards site it may cost 40,000 miles. Instead of redeeming the points on American Express, Greenstein advises transferring 40,000 of those points to the Delta rewards program.


This error seems counter intuitive: Airlines’ frequent flyer credit cards are not always best for free plane tickets.


“Even if you live in Atlanta—Delta’s hub—you’ll do much better with an Amex flexible rewards card. You might earn four Amex points for every dollar spent, which can be better than Delta’s card,” said Greenstein, who has joined every airline’s frequent flier program to maximize her points-transfer and redemption options.