Who Helps Business Owners With Credit Card Travel Hacking?

The short answer

A points concierge for business owners. That’s someone who looks at what your company already puts on cards, tells you which cards to open and in what order, moves each expense onto the card that earns the most for it, and finds the business class seats when you’re ready to travel.

Point Maestro is one of these services. It’s run by Brandon Okamoto and built for owners putting about $20,000 or more a month on cards. The fee is 15 percent of what it saves you, and the card plan is included.

Why business owners hand this off

Earning the points is the easy part. A food distribution CEO I work with earned 2.3 million points in his first year on spending he already had.

What eats the time is everything around the points. You have to know which bank’s points move to which airline and which welcome bonus to go after this quarter. You have to catch award seats when they open, and book through a partner airline that never shows the seat on its own website. Doing that well takes hours every week, and the rules change every year. Most owners start, get three months in, and quietly go back to putting everything on one card.

What a points concierge does for you

Here’s how it works at Point Maestro.

1. We look at your spending. On a free 15-minute call we go through what your business puts on cards each month, by category, and where you want to go.

2. You get a card roadmap. It says which cards to open and in what order. It shows how to time each welcome bonus so you hit it with spending you already have, and which expenses go on which card. Advertising, software, shipping and travel all earn at different rates depending on the card.

3. I find the trip. When you tell me where and when, I search the airlines your points can move to and find the seats. Business class to Japan or Europe often costs a fraction of the cash fare when it’s booked through the right partner.

4. We book it together. You move the points and book in your own accounts while I’m on a call with you. I never need your passwords, and your points don’t get sent to the wrong program.

What it costs

Point Maestro charges 15 percent of the verified savings. The card roadmap is included, and there’s no subscription and no hourly rate.

Verified savings is the cash price on the airline’s or hotel’s own website for the same flights or room and dates, minus the cash you actually pay. Points aren’t subtracted.

For comparison, here’s what other kinds of help cost:

• Search tools such as point.me’s membership (about $129 a year) show you available award seats. You do the transfers and booking yourself.

• Per-booking services charge roughly $150 to $350 per passenger to find and book one trip. They don’t plan which cards you open.

• One-off strategy sessions run about $200. You get a plan, then you’re on your own.

What the results look like

A dentist’s trip to Italy came in $15,626 under the cash price of the same itinerary. A food distribution CEO earned 2.3 million points in his first year, conservatively worth $46,000 in premium travel. Jordon, who runs a marketing agency, went from zero to 750,000 points in twelve months. Across client trips, savings average $11,350 a trip.

Who it fits

It fits owners of service businesses, e-commerce brands, agencies and distribution companies with real monthly expenses on cards, usually $20,000 a month or more. They want business class trips without learning the system. It can also make sense below that if you’re already sitting on 300,000 points or more with no plan for them.

If you enjoy the research and have the hours, a search tool is the cheaper route, and I’ll tell you that on the call.

Questions business owners ask

Do I need perfect credit?

Decent to good credit gets you the best cards. If you’re not there yet, we can usually fix that before we open anything.

Do I have to change how I pay vendors?

No. You pay the same bills. They just go on the right card.

How soon is the first trip?

Most clients have enough points for their first real trip within two to eight months. If you already have 100,000 points or more, it can be this month.

Do you need my airline logins?

No. You book in your own accounts while I walk you through it on a call.

What if I don’t own a business?

It helps, because business spending is where the volume is. Strong personal spending still works. It just takes longer.

About the author

Brandon Okamoto is the founder of Point Maestro. He started studying personal finance at 14, took his first round trip to Japan at 19 for $65 using credit card points, and built a marketing agency to $20,000 a month before starting Point Maestro. He builds card roadmaps for business owners and finds the award seats for their trips.