Why points and miles are too valuable for business owners to ignore

If you own a business, there are incredible opportunities to earn a valuable currency for the spending your business is already committed to. And yet, many business owners are stepping over dollars to pick up pennies when it comes to paying their bills.

I’ve been a business owner for almost three decades, and when I talk to fellow entrepreneurs about points and miles, I usually get the same responses:

• “I need reporting and expense tracking.”
• “Cash back is simpler.”
• “I’m focusing on running a business. Who has time to play around with points and miles?”

The truth? It’s a lot easier than you think.

Why leave free currency on the table?

Flexible rewards like Chase Ultimate Rewards points, American Express Membership Rewards points, Bilt Rewards Points and Capital One miles aren’t just perks — they’re strategic currencies that, when used wisely, can lower costs, boost employee satisfaction and unlock once-in-a-lifetime experiences.

Gone are the days when using credit cards made it harder to track expenses or pay bills. Today, major card issuers integrate with popular expense platforms, and spending is easily monitored across each card-holding employee.

A lucrative hobby for problem-solvers

Successful small-business owners are entrepreneurs at heart who see the world differently. Running a business means solving puzzles daily — and entrepreneurs excel at that.

By finding better ways to sell their product or serve their customers, they boost their chances of success. Applying that same mindset to payment methods can unlock substantial returns — especially on recurring expenses, which form the backbone of many businesses.

Simple adjustments for big returns

I’ve been in the hospitality business my entire life, spending much of the past two decades building and operating Five Guys restaurants. About 10 years ago, I had a conversation with our national Coca-Cola rep, who was brainstorming ways to encourage franchisees to pay their bills more regularly.

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He explained they accepted checks, wires and even credit cards — with no added fees. I paused and asked, “Coke will accept credit cards?” When he confirmed, I resisted the urge to immediately call our bookkeeper to switch payment methods.

Since that day, we’ve earned big rewards on all our soda purchases — at no extra cost. Even if we were just earning 2% cash back, that’s a strong tail wind on one of our largest recurring expenses. And all it took was a little work up front for a return that’s compounded over many years.

A guilt-free way to treat yourself (or your employees) 

Many business owners I’ve spoken with feel a sense of guilt for collecting points and miles instead of taking cash back. They believe they should “put it all back in the business” to be as profitable as possible.

But points and miles don’t have to be for personal gain. You can use them to offset employee travel — or, better yet, create meaningful “surprise and delight” moments.

Fostering great culture is harder than ever. One way we make our team feel valued is by gifting travel through rewards. Over the years, I’ve used credit card points to send employees to the Caribbean, Hawaii, Europe, Asia — even Disneyland and Disney World (yes, including theme park tickets). We’ve flown team members to be with sick family and, sadly, to attend funerals. The response I hear most often is: “I’ve never had a company do this for me.”

It’s a cinch to master, once you get started

When the light bulb goes on for entrepreneurs, they can apply all the tools that make them a great business owner to maximize rewards and quickly get through any learning curve.

One of my favorite success stories involves a close friend and fellow business owner, Bill. Bill likes to take his father all over the world on ski trips, and would end up paying way more than he should for not only his flights but also costly upgrades to extra-legroom seats that barely improved their comfort level on long-haul flights.

A few years ago, he called to ask if spending nearly 3 million Capital One miles was a good way to fly him and his 80-year-old father to Milan in business class. Spoiler alert: It wasn’t — and I’m glad I stopped him.

Instead, we searched Emirates, a Capital One transfer partner that flies between New York and Milan. We ended up transferring just over 300,000 Capital One miles to cover two round-trip business-class tickets.

Since that Emirates trip, not a month goes by that I don’t hear from Bill that his dad wants him to call “that guy who knows about the miles stuff” to figure out how to get them to some far-flung destination using Bill’s miles.

But Bill’s a fast learner, and with a little guidance from a points pro, he’s quickly become a master. Here’s another example:

Bill usually flies American Airlines for work due to its schedule from his home airport. Before we talked points, he’d never earned beyond Gold status. He was stunned when I told him I reached Executive Platinum status without even once flying American — I just use the right credit card for my business spending.

Following suit, he started using an American Airlines credit card for recurring charges that didn’t earn bonuses elsewhere. Those payments pushed him over the threshold for Executive Platinum just before the status year ended.

A few months later, I texted Bill a screenshot of my AAdvantage account to see which of us was further along in earning elite status for the following year. He was very happy to gloat that he’d already requalified for Executive Platinum, while I was still only halfway there.

Bottom line

Credit card rewards are just another puzzle smart entrepreneurs can solve to get the greatest return on money you’re already spending. With a little bit of guidance, strategizing and hustling, they can be powerful business tools.