September 24, 2023

Chappaqua’s Points Mom offers insight on credit card reward programs

Cindy Greenstein of The Points Mom. Contributed photo. Navigating through the world of credit card…

Chappaqua’s Points Mom offers insight on credit card reward programs
Cindy Greenstein of The Points Mom. Contributed photo.

Navigating through the world of credit card rewards programs and juggling multiple cards to achieve desired points and miles can be a daunting task. And that’s where Cindy Greenstein enters the picture.

A former public accountant, the Chappaqua resident had been giving free advice on her website The Points Mom since 2014 before making the decision in 2018 to operate it as a consulting company that offers one-on-one guidance and speaking engagements on the best ways to reap the most in rewards, points and benefits from credit cards.

Greenstein’s first brush with points expertise came around when she was an accountant fresh out of college, avidly traveling and accumulating points.

“I kind of got addicted at that point, just earning points and miles by flying and staying at hotels,” she recalled. “This was before any of the big banks had credit cards attached to the loyalty programs.”

Today, The Points Mom seeks to guide clients through the ever-shifting landscape of rewards cards and loyalty programs, subject to constant change by banks and companies, with both positive and negative impacts on existing cards.

“This game does not work if you apply for card, and you end up paying interest or fees. It totally negates any rewards you would ever earn,” she said.

Many of Greenstein’s clients are on the wealthier side yet still wish to visit exotic locations without the immense spending.

“We all love to travel, and there are so many cards out there that will get you to free travel if you use them correctly and apply for them at the right time,” Greenstein said, adding that one client will be travelling to Hawaii during the Christmas holiday thanks to her input.

Greenstein herself has gone on numerous vacations over the years with her family to popular destinations like New Orleans, London and Paris. However, Greenstein has found that the clients who get the most out of their cards are small business owners because of the large expenses that happen when running a business.

“If you have a small-business, you can have personal cards and you can have business cards, and those cards can kind of earn the same rewards that all flow to the same bucket,” Greenstein said. “It’s a lot easier to earn and get free travel.”

Greenstein drew attention to three cards of interest to those looking to earn the most points. The first is the American Express Gold Card, a card which earns the same points as other American Express cards people might already own, such as a Platinum Card. Gold Card holders earn four times the points per dollar for dining and groceries. The annual fee is $250, though Greenstein noted that diligent usage of the card’s monthly benefits allows one to bump this down to $10.

Greenstein also recommended Capital One Venture X, which gives two miles for every dollar spent, regardless of what is purchased. A mile earned can be redeemed for one cent and is not tied to Capital One’s website. Additionally, Capital One offers $300 travel credit (albeit usable only through and also gives holders 10,000 bonus miles every one-year anniversary, meaning holders can more than cover the card’s $395 annual fee.

Yet another card Greenstein praised is the Chase Sapphire Preferred Card, which she suggested especially to those entering the world of points and miles for the first time. Holders can earn three points per dollar spent on dining or streaming services or two points for travel. But what is most appealing about the card, Greenstein said, is that one point can be redeemed at $0.125. However, she cautioned that “you are limited if you’re going to use them as money to go through the Chase travel website.”

Regardless which card is utilized, Greenstein stressed that loyalty programs are to be avoided.

“One mistake I think people make is that they use a credit card tied to a loyalty program for their everyday spending. And what I recommend is using a card that earns flexible miles or points for your everyday spending, where you can use those points as money or you can transfer them to partners,” Greenstein advised.

The rewards and points industry managed the effects of the pandemic well enough due to companies’ efforts to retain and attract customers in response to decreased travel.

“Most of the companies gave amazing incentives that we’ve never seen before, and we will probably never see again,” Greenstein said, noting this resulted in companies greatly reducing the number of points needed to reach top-tier status, which comes with additional rewards and bonus points. JetBlue is one such company, having reduced the number of points needed to reach its Mosaic status from 50,000 points down to 15,000.

The waning severity of Covid-19 in the public’s eye as of late has, according to Greenstein, resulted in an increased urge to travel among her clientele.

“I just think people want to travel, and they’re maybe willing to spend a little bit more,” Greenstein said. “Maybe it wouldn’t be like this had Covid not happened, and maybe people wouldn’t be wanting to spend that little extra amount on a hotel or a flight.”

Though Covid-19 has not had a massive negative impact on her business, Greenstein put forth her desire to improve the one-woman operation, namely in how advice is transmitted.

“While I’m going to continue to do my consultations, I am trying to grow my social media, and try to do more speaking engagements,” she said, citing her one-on-one consultations while hoping to build up to group sessions with around 10 or more clients.