What's in My Wallet? May 2019 Edition + 100,000 Subscriber Celebration Giveaway

The cards in my wallet rotate each month depending on if I open a new card or what my spending habits will be. Before we dive into what’s in my wallet, we want to say a huge THANK YOU for 100,000+ subscribers on YouTube!

We were initially waiting for the silver play button to arrive to unbox and host a giveaway, but it seems like that might take a few months.

Ask Sebby 100,000+ Celebration Giveaway!

5 lucky winners will be selected at random to win a super limited edition Ask Sebby luggage tag.

Luggage Tag Design

The luggage tag design was inspired by YOU. It’s something you can take along everywhere you go and fasten it to a backpack, carry-on, or keep it on your desk.

  • Established 2016 stamp: Ask Sebby’s first upload was in December 2016

  • 100,000: 100k YouTube subscribers milestone

  • Your Mileage May Vary: with everything in life, YMMV depending on what your goals are and how you choose to achieve them

  • World Map (back design): for wherever your adventures may take you

ask sebby luggage tag.jpg


  1. Must be 18 or older to enter.

  2. Must have a U.S. mailing address. Any winners picked that do not have a U.S. mailing address will be disqualified.

  3. Sweepstakes Period: Entries will be accepted online starting on May 20, 2019, and ending June 3, 2019. All online entries must be received by June 3, 2019 11:59 PM PST.

  4. Winners will be notified via email. Winners have 7 days to respond; if no response, we’ll pick another winner.

What’s In My Wallet?

Alaska Airlines Visa® Business credit card

One of my goals is to fly Emirates First Class, and Alaska miles are one of the best ways to achieve that.

  • Annual fee: $75 annual fee ($50 for company and $25 per card)

  • Intro bonus: 40,000 miles

  • Earn 3x on Alaska Airline purchases

  • Earn 1x on everything else

For my situation, here’s the cost breakdown of adding the Alaska card:


  • 1 inquiry (not getting a mortgage anytime soon)

  • $75 annual fee ($50 for company and $25 per card)

  • $50 Plastiq/rent fee ($2,000 * 2.5% = $50)

  • = $125 + 1 inquiry

The benefits outweigh the costs since there are various ways in which I can come out ahead. If you need help meeting minimum spend, learn more about Plastiq in this post.


  • 40k of 70k = 57% of JAL F (Japan Airlines First Class)

  • Retail = $9,036 one-way ($18,071 RT / 2)

  • I would happily pay $1,000 for one-way

  • For comparison: RT economy is ~$550 to $600 during sales from SFO to Tokyo.

Another good use case for Alaska miles is to fly Cathay Pacific First Class. Check out the video below to learn more.

The Business Platinum® Card from American Express

I’ve received the intro offer for the Business Platinum Card in the past, so the reason for adding the card again is for the WeWork benefit. The card grants you global access to WeWorks worldwide during regular office hours.

Even without the intro bonus, I’m getting positive expected value from the airline and Dell statement credits.

Cost: $450 (I applied before the $595 change)


  • $200 = 2019 airline incidental credit

  • $200 = 2020 airline incidental credit

  • $100 = 2019 (Jan to June) Dell credit

  • $100 = 2019 (July to Dec) Dell credit

  • $100 = 2020 (Jan to June) Dell credit

Benefit = $700 credits + WeWork (1 year)

Chase Freedom

The Chase Freedom is my go-to for grocery shopping since I’m trying to accumulate more Ultimate Rewards points.

For Q2 2019:

  • Earn 5x on grocery stores, NOT including Target and Walmart

  • Earn 5x on home improvement stores

Earn 5x on up to $1,500 in combined category purchases each quarter you activate.

The Gold Card is in my wallet for all my dining purchases. There’s also the $10 Grubhub statement credit that I still need to use this month.

See if the Gold Card is worth it for you using this calculator.

Editorial Note: Opinions expressed here are the author's alone, not those of any bank, credit card issuer, airlines or hotel chain, vendors or companies, and have not been reviewed, approved, or otherwise endorsed by any of these entities. 

UGC disclosure: These responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.