Can you get business class flights for free?

Michael Wu, long-time travel hacker, Stanford alum, and ex-Stripe software engineer, shows us how he gets the craziest deals using credit cards and travel rewards.

Today in 10 minutes or less, you’ll learn:

• 🇯🇵 How Michael Moved from the US to Japan as a Software Engineer

• 🤑 Cheap Long-Haul Flights, Plus Resources & Tools He Recommends

• 💳️ Credit Card, Airline, and Hotel Rewards; Status Hacking Tips

• 💁‍♂️ Michael’s Craziest Deals, Travel Hacking Tips, and Advice for Japan Expats

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✈️ Travel Hacking 101 | Michael Wu

Michael is a software engineer and founder with experience in Silicon Valley as well as Japan. He’s currently splitting my time between Tokyo and Taipei, as well as traveling all over the world. He’s also a travel enthusiast, foodie, angel investor, and blogger who loves helping people travel better.

🛣️ Tell us about your career journey going from the US to Japan as a software engineer.

I moved back to the Bay Area after doing my undergraduate degree at Princeton, and completed a master’s in Electrical Engineering at Stanford.

Then I joined some Stanford friends as a Founding Engineer at Pixelapse, which was acquired by Dropbox in 2015. I worked for 4 years at Dropbox culminating in their IPO.

Why I wanted to move to Japan: I started studying Japanese in college and had many Japanese friends from hosting them as exchange students. I would frequently visit and fell in love with the lifestyle there.

After spending 10 years in the Bay Area, I decided to finally move to Japan. Unfortunately, I was unable to transfer through Dropbox.

It took a while to find a job that would allow me to move to Japan, but fortunately I eventually landed an offer with Stripe, and moved in February 2020 right before Japan closed their borders due to the pandemic.

I was at Stripe for almost 3 years, until the end of 2022. Now I'm working on my own projects!

For those interested, here’s a post on how I navigated my software job search in Japan.

🤑 You’ve frequently traveling around Asia and rest of the world. How have you managed to snag cheap flights? What tools and steps do you take?

1/ I subscribe to cheap flight deal newsletters:

• The Flight Deal and Going

• Watch RSS feeds for FlyerTalk Deal forum 

• Premium Flights

• Premium Cabin Deals

2/ Long haul international flights - I usually redeem points on business class or first class. I will also jump on paid business class deals:

• Learn the in and outs of a few major airline programs, as well as patterns in award availability. For example, award flights are usually available when the schedule releases a year ahead of time (actual days depends on program), as well as last minute close to your trip.

• You can use points search engines like PointsYeah, Roame, Points.Me to find award availability and compare costs. They don’t always cover all options, so it’s good to also know how to use specific airline websites to search award avaiability as well.

• Straight to the Points is a service that alerts you to large drops of airline award availability.

• I’m often flying back and forth between Asia and the US, or Asia and Europe so am usually redeeming points on Korean Air, JAL, ANA, EVA, China Airlines, etc. Unfortunately it’s become not as worthwhile to redeem Singapore Air miles.

For example:

• One of my craziest deals was a $500 Business Class flight on LATAM from Mexico City to Cape Town, South Africa.

• The original itinerary was cancelled, but LATAM let me rebook from a 3 stop itinerary to a full fare business class flight with 1 stop in Frankfurt on Lufthansa.

3/ For flights within a region, like Asia or Europe, they are often not outrageously priced and I just watch price trends and buy when there's a deal.

There are a couple of programs, such as with the Chase Sapphire Reserve and Amex Points Rebate where you can pay for travel with points and get 1.5 USD cents per point value or better.

Sometimes I book through credit card portals as they offer increased points earning - the CapitalOne Portal also does price matches as well as price drop protection. There are a handful of point redemptions for regional that can be worth it though, so check the award flight search tools.

💳️ What credit card and travel rewards programs do you use or recommend?