Why Insurance is Never a Good Deal

And 4 Times When You Should Pay for It Anyway

When you purchase a computer, should you buy insurance in case it breaks? Or should you purchase travel insurance for a trip? What about car insurance, health insurance, homeowner’s insurance, or life insurance? You can save a lot of money over a lifetime by answering these difficult questions well.

Building destroyed by Hurricane Irma on St. Maarten island

Properly understood, insurance is always a bad deal. But there are 4 times when you should get it anyway. Let me explain. (more…)

How to Get 23 Months of Free Flights with the Southwest Companion Pass

Act by 10/4 (ideally *on* 10/3) to Maximize the Best Deal in Travel, Worth More than $1,800

The Southwest Companion Pass is arguably the best deal in travel. It allows a companion to fly for free with you on any Southwest flights you book. The pass is good from the time you earn it until the end of the following calendar year. The opportunity has arisen to enable a companion to fly for free with you for 23 months: most of 2018 and all of 2019. But you have to act by October 4, 2017 (and, ideally, on 10/3) to take advantage of this opportunity.

The Southwest Companion Pass works on all Southwest flights.

Following is more about the Companion Pass and exactly what you need to do by October 4th in order to score 23 months of free flights for your companion (and a lot of free flights for you as well): (more…)

How to Decide Which New iPhone to Get

And is the iPhone X worth $1,000 -- $300 more than the iPhone 8?

Last week, Apple announced three new iPhone models: the iPhone 8, the iPhone 8 Plus, and the iPhone X. (The “X” is pronounced “Ten,” in commemoration of the iPhone’s 10-year anniversary, but probably only “I in X” people will pronounce it correctly.) My first reaction to the X was this well-thought-out response: “I want.” I still do. But I’ve stopped drooling long enough to ask myself the question: is the iPhone X worth its $1,000 price tag? More specifically, is it worth $300 more than the also brand new iPhone 8? At least one person on Twitter thinks maybe not:

Funny picture suggests the iPhone X will cost one human life

In this post I’ll compare the three new iPhone models. My aim is to help any of you looking to get one of them to decide how best to spend your money. (more…)

How to Blow $4,000 on a $56 Vacation

It’s All Too Easy to Do

When people go on vacation, they often pay face value. According to Forbes, the average vacation costs $1,145 per person or $4,580 for a family of four. I love family vacations because I like going on an adventure with my wife and kids. But I would never consider paying over $4,000 for a vacation. And I don’t want you to, either.

The three kids and I on the beach during our vacation to San Diego

On my last two family vacations combined, I spent less than $100 total on hotels and flights. Earlier this year, we took a $5,000+ vacation to Cabo San Lucas for $42. Last week, we took a short (2 night) vacation to San Diego for $56. Had we paid face value, the hotel and flights would have cost $4,012.

If vacations are part of your life—or if you’d like them to be—you should seriously consider a total paradigm shift in terms of how much you think they need to cost.

In this post I’ll share how we spent so little on a great vacation. And I’ll show how you can do similarly. (more…)

How to Save Money on Rental Car Insurance

Car Rental Insurance is Confusing and Expensive. But Should You Get It?

You just landed at the airport, ready to start your beach vacation. You can’t wait to change your sweaty clothes for a swimsuit. So you head to the car rental agency to grab your car and be on your way. But first, you must make a series of important decisions that you feel completely ill-equipped to make. Do you want collision coverage on the car? What about liability insurance? Seems expensive. But the agent swears you’d be crazy not to purchase the coverage he’s selling.

Long lines at rental car agencies as renters contemplate what rental car insurance to purchase

Your eyes begin to glaze over. You quickly initial here, here, and there. Depending on your decision, you either just forked over a bunch of cash or waived coverage. Either way, one thing is likely: you don’t have good reasons for the decision you made.

I know, because I’m right there with you. Or at least I was until last week.

Over the past week, I’ve done a bunch of research to try to answer the question: When renting a car, should I buy rental car insurance?

Following is the fruit of my research. It will shape whether I accept or decline rental car insurance moving forward. (more…)

AutoSlash: How to Get the Lowest Price on a Rental Car

And Do So with the Least Amount of Effort

When renting a car, I want to get the cheapest rate possible with the least amount of effort. You, too? If so, you need to use a free site called AutoSlash. I’ve used AutoSlash dozens of times since 2011. On one occasion, AutoSlash saved me a whopping $2,178 (74%) on a 27-day SUV rental. On at least 10 separate occasions, AutoSlash saved me more than 31% off the lowest rate I could find. Due to its considerable savings and ease of use, I highly recommend using AutoSlash every time you book a rental car.

Woman in rental car holding car keys

In this post I’ll explain what AutoSlash is and show you how to use it to quickly save a ton when renting a car.

(more…)

1 Big Reason to Shop at Bed, Bath, & Beyond

And the Top 4 Stories that Illustrate their Amazing Return Policy

What if you could buy a product, use it until it wears down or breaks, and then return it—even years later—for a full refund or exchange? Sounds like wishful thinking, right? Amazingly, that is precisely how returns work at Bed, Bath, & Beyond. In this post, I’ll explain how to make the most of their generous return policy. But first, I want to share four quick stories that illustrate just how absurdly generous the policy is. You won’t believe what they are willing to let you return.

The front of a Bed, Bath, & Beyond store

Top 4 Stories of Returns to Bed, Bath, & Beyond

The following four stories illustrate the absurdly generous return policy of Bed, Bath, & Beyond:

#4. My Return of a Patio Umbrella

(more…)

4 Ways to Save Money on Groceries Quickly

How to Save Money on Groceries, Part 2 of 2

In my last post I argued that you can save substantially on groceries—perhaps 19% or $760 per year—by having them delivered to you rather than going grocery shopping. Doing so saves a lot of time, too. But I also acknowledged that sometimes it makes more sense to shop for groceries in store. When shopping in store, there are still ways to quickly save money on groceries.

Woman in grocery store, contemplating which groceries to buy

Following are 4 efficient ways to save money when shopping for groceries in the store: (more…)

How to Save $760 on Groceries in No Time

How to Save Money on Groceries, Part 1 of 2

The average American household spends over $4,000 per year on groceries. As a result, saving even a small percent on groceries can add up. That said, many cost-savings tactics—like clipping coupons—often aren’t worth the time. The question is: how can one save the most money on groceries in the least amount of time?

Man delivering groceries to a woman at her home

In this two-part series of posts, I’ll share 5 ways to quickly save on groceries. Today I want to share my #1 recommendation: (more…)

SeatGuru: How to Get the Best Seat on the Plane

Plus a Special Bonus Trick that I Love

Whether flying in economy, business, or first class, you want the best seat for the money you spend. Some seats—such as those near the bathrooms—you know to avoid choosing. But how can you know in advance which seats don’t recline or which have misaligned windows? On the other hand, how can you know which have extra leg room or AC power so that you can charge your device in flight? The answer is SeatGuru.

Exit row seats

I’ve used SeatGuru for many years to help me get the best seat for the money. In this post I will explain how SeatGuru works and show you how to use it to get a great seat on the plane. (more…)