✈️ March Madness (Daily Drop edition)

✈️ March Madness (Daily Drop edition)

Estimated read time: 4 minutes and 11 seconds

The odds of getting a perfect March Madness bracket are 1 in 9,223,372,036,854,775,808… wrap your mind around that for a sec… 🤯

Good morning and welcome back to another week of Daily Drop travel hacking fun times. Boy, is it going to be an exciting week for you… *hint hint*

Let’s start off with the first day of exciting stuff:

  • ✈️ FINAL DAY to get your Southwest Companion Pass

  • 🏀 We’re hosting our own version of March Madness

  • 💸 Reminder: Maximize points on your taxes

✈️ TODAY: Last chance to get your Southwest Companion Pass

You all probably know this by now since we’ve beaten the subject to death with a spikey baseball bat like Negan from The Walking Dead, but today is the last day to earn a Southwest Companion Pass for an entire year just for signing up for a credit card.

I’ve said it once or twice (or more) and I’ll say it again; this is probably the best travel hack we’ll see in a very long time, and can easily help you save thousands of dollars per year in airfare if you play it right.

So if you’ve been on the fence about this or you’re hearing about it for the first time, check out our article and see if this might be a worthwhile strategy for you:

🏀 We’re hosting a travel tournament of champions this month

If you’re like me, you know a TON about sports. That’s why when March Madness started this year, I knew exactly what was going on.

Of course, I didn’t really know what was going on.

Thankfully, we have staff here at Daily Drop who actually know how this sport works and explained to me in-depth what March Madness is.

I won’t go into the details of what it is… because I still don’t totally understand it.


We have decided to host a Travel Tournament here at Daily Drop, modeled after this exciting sports tournament thing that people apparently love.

Here is how it’s going to work:

Over the next few weeks, we’re going to put some of our favorite travel airlines, destinations, points programs, and perks head-to-head and have YOU readers vote to determine the winner.

After a few rounds of competition, we’ll arrive at the final winner: the champion of champions.

The tournament will consist of 64 competitors, broken into the four following groups:

  1. Airlines

  2. Bucket List Destinations

  3. Points/Loyalty Programs

  4. Travel Perks

Tomorrow, we’ll put a few polls in the newsletter. You’ll vote on your favorite option, then we’ll use the results to determine winners from pre-selected head-to-head pairs.

It’s going to be VERY cool, so don’t miss it.

💸 Maximize points on your taxes

Springtime is always a season full of sunshine, hope, and splendor.

That is, until you get your fat tax bill and have to shell out your hard-earned dollar bills to the government. Since we’re right around the corner from the tax deadline, I wanted to give you a refresher on the topic from a points and miles perspective.

As someone who has owned a business and done lots of freelance self-employment work, I know the pain of having to pay big quarterly or annual tax bills, even when you plan for it accordingly.

You may not know that there are ways to profit massively off your tax payment and even turn it into a luxurious business class flight... 😮

Allow me to explain:

You may be aware that you can pay taxes using a credit card, usually with a pretty sub-optimal fee attached.

For example, the IRS website gives you multiple options for different payment processors, along with the various rates they each charge for different payment methods.

All of them will charge you just shy of 2% in fees to pay with a credit card. For the sake of this example, let's conservatively call it 2%.

Let's say you rack up a $10,000 tax bill. This is not unreasonable for freelancers, small business owners, and others with supplemental income.

The 2% fee would mean you would have to pay an additional $200 just to use a credit card. In most cases, paying more money to earn more points is rarely worthwhile. 

But if paying that $200 helps you to hit the minimum spend on one or two credit cards, it could actually be a great opportunity to rack up points that will far outweigh that $200 in value.

For example, this card has a huge welcome bonus and tons of great perks but requires you to spend $6,000 to get the bonus.

Some people may struggle to spend that much and might even spend money they otherwise wouldn't just for the sake of the bonus. This is bad, and we don't want to do this.

But if you have a $10,000 tax bill, you'd eliminate that spending requirement in one swoop. Is not having to worry about reaching the bonus over a 6-month period worth the $200 processor fee? For some people, it just might be.

If you want to take this to the next level, you could open this ad-Venture-ous card (see what I did there?) AND this middle-tier card, both amazing options. Since they each require you to spend $4,000, you'd earn both signup bonuses and earn nearly 150,000 points, enough to book an entire trip somewhere! 

Is a free trip abroad without stressing or waiting to earn points worth $200? For most of you, I'd guess the answer is yes.

That’s all for today, friends… Keep an eye out for tomorrow’s newsletter where you’ll get the chance to vote on the first round of the travel competition… It’s going to be epic.

By the way - while this March Madness stuff is exciting, it’s not even the most exciting announcement we have for you this week… 😏

Are you a sports fan? Who’s your favorite to win March Madness? If you aren’t a sports fan, what is your favorite… uhhhh… flavor of ice cream, maybe? Let me know by replying to this email or reaching out on social media.

See you tomorrow,

Mike Dodge
Head Writer, Daily Drop

35.6762° N, 139.6503° E

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