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September 14, 2026 | View Online
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I don’t think you’ll understand how impressive I was this week.
It took me just five days from creating a group chat to coercing sixteen men into paying deposits, accommodation costs, and flights to Phuket in November for a football tournament and lads trip.
Two of them have asked me to organize their weddings.
Oddly, their fiances are not as into it.
Let’s get to the points:
Cheers,
Steven
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| AUTO INSURANCE
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When Did You Last Compare Car Insurance?
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Car insurance rates can change more often than you might expect, which means your current policy may no longer be your best deal.
Taking a few minutes to compare quotes could help you find the same coverage at a lower price.
Money.com's free comparison tool lets you review rates from providers in your area—all by answering a few simple questions. See if you could save today.
Compare rates.
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| WHAT'S THE POINT?
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Is Buying Points Ever a Good Idea?
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One of the most asked questions I get from readers revolves around buying points. In short, is it ever worth it?
In general, the answer is no. Let me show you why.
Air Canada’s Aeroplan is currently offering up to a 100% bonus when buying points (they only offered me up to 85% for some reason, but hey ho). This seems brilliant, but consider the difference between earning points and buying points.
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When earning points, you’re getting points on spend that you’d make regardless of whether you’re looking for them. They’re a pleasant add-on a card issuer is gifting you in exchange for using their product. As long as you’re not spending just to earn points, it’s true value. If i redeem those points for 1 cent each, I get $1,000 in value after spending 100,000 points.
But if I buy points directly from an airline or hotel, I’m not earning them. It’s a direct transaction. You pay them money, and you get points back. And that’s where it gets hairy.
Look at the Air Canada options — I’ve converted the Canadian dollars to USD, if you get confused).
About $80 gets me 4,050 points — and that’s including a 35% bonus. That means I just paid around 1.9 cents per point.
Even further up the chart, earning an 85% bonus by spending $1,351 to get 92,500 points only gets me 1.45 cents per point. It’s better but still not great.
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To make this worth it, I’d need to guarantee that any flights I redeemed them for got me well over that valuation. But there’s the issue. I need to work much harder to ensure I came out ahead.
If I had redeemed 2 of these flights from Lisbon to New York for 80,000 points plus $230, I’d have got around 1.93 cents per point. If that was from traditional earnings, that would have been great. But I had to buy those points for around $1,300.
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The good news here is that I still came out on top, saving around $474 compared to paying cash. If I had bought those points without the 85% bonus, I’d have dropped around $2,162 for enough points to redeem two $887 tickets. In short, I’d have been down $388.
In short, are there times when buying points can make sense? Yes. You can save money for sure if you have a specific redemption in mind, but it’s likely to be when a bonus is running. It’s also possible if you’re a few thousand short on a huge redemption, but again, always check the math on it.
In most other circumstances, you’re going to need to pull off some magic to make sure you get your money’s worth.
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| ONE MINUTE UPGRADE
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One Thing You Can In The Next Minute To Work Your Points Better
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Delete your debit card from Uber Eats.
Seriously. Do it now.
If you're going to spend $34 getting a $17 burger delivered because you can't be arsed putting trousers on, the absolute least you can do is earn some points on it.
A lot of us have old debit cards attached to apps that have been around for a while. Food delivery, ride hailing, or subscriptions – seriously, I didn’t realize my debit card had been on my netflix for almost a decade. Use a better card.
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