🐧 Travel hacking 101 | Michael Wu

Cheap Long-Haul Flights, Airline & Hotel Rewards, Japan Expat Life, Status Hacking
November 19, 2023

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

FROM OUR LABS

🧠 Join my beta program to launch a $1k/month remote side hustle

Tacos are incredible. This course is even MORE incredible than tacos. 🌮

We’re launching an exclusive Beta Program for our upcoming course, Remote Side Hustle Profits. (title TBD)

After generating over $30k in remote side hustle revenue, I’ve received an overwhelming amount of questions from readers about how to earn an extra $1,000/month on the side.

Why join the Beta Program?

  • ⌛️ Early Access: Be the first to experience the Remote Side Hustle Profits curriculum, get personalized Q&As, and co-create the course with me.
  • 🧠 Shape the Course: I will be starting from scratch and creating course videos on a weekly cadence based on your feedback over a 4-week course creation sprint (95% async).
  • 🌎️ Intimate Community: Connect with like-minded professionals from diverse sectors, including tech and finance who are also part of the beta program.
  • 🔥 Exclusive Price: In exchange for your help, I’m offering a 75% discount ($222 value). Plus, if you complete the beta tester feedback form, then I'll rebate 100% of your fee.
  • 🏇 Limited Spots Available: Act fast! We're accepting 25 beta testers.

Interested?

👉️ Apply via this 5-minute form, then we’ll get in touch about next steps if there’s a good fit!

✈️ 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:

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?

Credit cards:

  • Chase, CapitalOne, Amex, Citi, Bilt. These are flexible to transfer to partners and generally don't expire as long as you hold an account. However, these are really only accessible to US citizens or residents.
  • Amex and Citi also have credit card points programs in other countries but tend to not be as lucrative as the US, but sometimes you can find sweet spots.

Airlines:

Airlines are split into the 3 major alliances, Star Alliance, oneworld, and SkyTeam, and then independent airlines (Emirates and Etihad being notable in their partnership networks) and LCCs (Low Cost Carriers).

Each airline and loyalty program has their unique points, and I recommend focusing your efforts on a few that are useful to you:

  • Asiana is easy to earn Star Alliance status on, and you can keep it for up to 4 years.
  • Aeroplan (Buy Miles promo until Nov 29th) and Avianca LifeMiles are on Star Alliance as well and cheap to buy points for with good redemptions.
  • For SkyTeam, Air France / KLM's program FlyingBlue can have good redemptions, and Delta occasionally is useful as well.
  • For oneworld - American and Alaska can have good redemption values but hard to access if you can't get US credit cards. You can buy Alaska miles at good value.

Hotels:

Check your global and local loyalty programs, sometimes there are sweet spots. You're looking for ways to get outsized value:

  • My all time favorite is Hyatt for the benefits and service, but footprint is limited. You can transfer Chase points to Hyatt, and it is one of the few hotel partners worth transferring to as you can frequently get better than 2 cents USD value per point.
  • IHG Hotels have a wide footprint and have recently improved their loyalty program. (Buy IHG promo until Dec 30th)
  • Marriott has decent status recognition and you can often get good deals. Marriott has credit cards in many countries aside from the US that help you earn status faster.

Gaining status faster

If you travel a lot, you start to appreciate the benefits of loyalty program status to improve your travel experience.

But obtaining status normally requires flying, staying, or using the service in question a number of times first without status, which can be challenging.

You can also shortcut the normal process and get status earlier. Here’s a few ways to do this:

  • Membership programs like FoundersCard or certain higher end credit cards comes with status in various loyalty programs. For airlines and hotels, it is usually low or mid-level status, and for rental cars, it is top tier status.
  • For statuses not available through membership programs, you can often do Status Matches or Challenges. A match gives you the status outright just by providing the required credentials or proof of status in another program. A status challenge requires you to use the service a certain amount before giving you the desired status.
  • Find current offers and success reports at at Status Matcher as well as travel blogs like One Mile At a Time, View From the Wing, etc. to see opportunities as they pop up.

🫶 Can you share an example of how you find outsized value in your local loyalty programs?

I find having mid-level airline status useful for Priority check-in, boarding, lounge-access, extra luggage allowance, etc.

But maintaining airline status is difficult, especially if you are redeeming points for long-haul flights.

How to get indefinite status

With the two major Japanese airlines, you only have to obtain status one time, and then you can keep the status indefinitely without flying:

  • For ANA - all you need to do is sign up for a special credit card and pay the annual fee each year, though this requires living in Japan. More details here
  • For JAL - you can either sign up for a special credit card and pay the annual fee, or pay 5000 JAL miles each year to maintain your status.

Side notes:

  • Asiana is great too as you can earn status over 2 years, and keep it for 2 more years, meaning if you timing things right, you can get Star Alliance Gold Status for 4 years! But there’s an impeding merger with Korean Air which might make this go away.
  • Even though US credit cards still have the best rewards and sign up offers, sometimes there are attractive local credit cards. I’ve found that American Express still offers fairly high signup bonuses in non-US markets, though their annual fees tend to be higher.
Dinner at the underwater restaurant at the Conrad Maldives

🎌 You’ve been living in Japan since 2020. What’s one money hack you can share for expats looking to settle in Japan?

  • Find a bank with good customer service and low fees for things like ATM withdrawals and transferring money. I'm a fan of Shinsei and Sony Bank.
  • Figure out a good setup to transfer money to and from Japan conveniently and with minimal fees. Wise for smaller transaction (Revolut is even cheaper under 750000 yen out each month, but that’s minor
  • Pay your taxes with credit card and earn points. Learn about the hometown tax donation scheme for free goods.

💁‍♂️ What non-obvious advice would you give to fellow world travelers looking to save on travel spend?

  • Buying points strategically when they are on sale. Ones that are typically worth it: Air Canada Aeroplan, Avianca LifeMiles, IHG, Hilton. For Avianca and Aeroplan, aim for 1.35 US cents or less. For IHG and Hilton, they frequently go as low as 0.5 US cents a point. You can follow the travel hacking blogs like One Mile At A Time to know when they go on sale. You don't need to be US based or have access to US credit cards for these!
  • Add your loyalty number when visiting hotel restaurants or bars to earn points and get a discount. One time we were dining at the underwater restaurant at the Conrad Maldives with a $6000 USD bill. I calculated that I would earn 120,000 Hilton points on the bill, but they wouldn’t let us credit it unless we were staying the night. It was only 95,000 Hilton points for an award night, so I booked one on the spot, we got to hang out a nice overwater villa, and I earned 35,000 net points on top of that!
  • You can pay your local taxes with a credit card to earn points or meet credit card signup bonuses. For example, I’m able to pay taxes in Japan for a 1.1% fee via credit card. In another case, when paying US taxes, credit card processing fees are between 1.85-1.98%, which can make sense if you are trying to meet a signup bonus or you can earn points or cashback worth more than the fee.
  • Hit spending bonuses by loading up on Amazon gift cards if you are going to use them anyways.
  • You can buy travel gift cards when they are on sale and either use them or resell them to earn credit card points. I’ve seen Marriott, Uber, Alaska, and Southwest Gift Cards frequently on sale.
  • RocketMiles is useful too for earning extra miles for staying in hotels

🏡 Where can we go to learn more about you?

🌐 Beyond your borders

 🇺🇳 The UN World Tourism Organization (UNWTO) reports that over 50% of countries offer a digital nomad visa now (link)

🏖️ Hampton releases a Wealth Allocation Survey similar to Tiger21 (link)

🤓 When it comes to Retirement Plans, how safe is an 8% withdrawal rate? (link)

🇸🇬 Expats in Singapore: How To Choose The Right Travel Insurance (link)*

*this is a sponsored link

📆 How I can help

That’s all for today!

Whenever you’re ready, here’s how I can help you:

  1. Work with me 1:1 - Book a coaching session for your next career transition.
  2. Work with my tax team - Get personalized US expat tax help.
  3. Join my side hustle course - Learn to build a remote side hustle that earns you $1,000/month on the side (limited slots available!)

For daily insights, follow me on X (@dexteryz) or Linkedin.


If you liked this post, you'll LOVE my newsletter

Every week, get a free actionable strategy to help you build wealth overseas:

Dexter Zhuang

Dexter is the founder of Money Abroad, a website focused on financial independence for professionals abroad. He has 10+ years of experience building products and teams at companies like Dropbox, Xendit, and startups. He's lived and worked across the US, Asia Pacific, and Latin America. His work has been featured in global publications like Business Insider, CBS, US News & World Report, and Tech in Asia. He graduated from Dartmouth College.

Continue reading

🐧 Ultimate Guide to Semi-Retirement
Financial Planning

🐧 Ultimate Guide to Semi-Retirement

Why 2020's are Different, My Money Journey, Why Semi-Retirement, How to Calculate Your Semi-FIRE Number, Downsides
🐧 The Fear Compass: 4 lessons on fear in decision-making
Personal Development

🐧 The Fear Compass: 4 lessons on fear in decision-making

My Journey, Truth, Friendship, Courage, and Margin of Safety
🐧 Fractional job search | Taylor Crane
Career

🐧 Fractional job search | Taylor Crane

INSIDE: Poker Player to Fractional Head of Product, Fractional Job Search Mistakes and Tips

Search

Enter keywords and click search.