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My Interview with Seth and Osa (A Husband /Wife Team of Points Enthusiasts)

This interview is a bit unusual because both spouses are participating. How cool is that? One of these days I plan to interview my husband and ask him how he feels about this hobby. That will be one super short post.

Anyway, I’ve “met” Seth (the husband) about a year ago. In his emails he came across as an extremely nice guy, very much a family man. So, it shouldn’t have come as a surprise to me when  he asked if his wife could participate in the interview. Of course! On my blog we have one rule: “There are no rules.”


1) What motivated you to research miles and points hobby?

Seth: We started collecting miles in the late 90’s from occasional vacations and various promotions. My favorite was earning five to ten thousand miles for switching landline telephone providers – which you could do every 6 months. This was my personal version of “churning”.

Osa: Seth simply wanted to accrue large account balances, but never gave any thought to redeeming until I suggested it.

Seth: Osa was right. In retrospect, I don’t know what I was thinking.

Our first big redemption was a trip to New Zealand, which sparked our love affair with the country.

2) What are the biggest challenges you face trying to navigate miles and points hobby?

Seth: Our biggest challenge is needing 4 seats – often during peak travel seasons and school breaks. This has forced us to be resourceful and creative, and to learn the ins and outs of many programs.

We’ve been prepared to split up on different flights due to limited availability, but it’s almost never come to that because of schedule changes, success with HUCA (Hang Up and Call Again), and “my favorite rule” – unlimited free changes on AA as more award availability comes into the system.

Osa: 11 months of daily entertainment for Seth (since we book far in advance)! I’m reminded that when I was pregnant, Seth would always tell me this is going to be our “last trip”, that we won’t be able to sustain this life with children, we won’t be able to accrue enough miles, find additional award seats, etc. I never believed him!

 A funny/embarrassing Seth story comes to mind. When I was pregnant with our first daughter, my due date was around Thanksgiving. Seth “joked” that he wanted me to deliver after the holidays so we could book a Thanksgiving trip 2 years later while our daughter was still a free “lap infant”.

It didn’t quite work out that way, but we found a loophole on AA that when your child is under 2 years old for the outbound, you can get the return for free – even if your child is already two years old.

Seth: Of course I was joking, dear…

3) What’s your favorite trip that was made possible solely due to miles and points?

Osa: There’s no way to answer this without sounding entitled and gluttonous. We’ve been playing the game for a number of years, so there are quite a few favorites. At the top of the list is New Zealand (we’ve made a bunch of trips and still haven’t come close to seeing/doing everything), Palau (where we snorkeled with jellyfish), and Hawaii (where we got married).

Seth: There’s a misconception that international travel is prohibitively expensive, but it really doesn’t have to be if your flights are free.

4) How often do you think about miles and points?

Seth: We love to travel, so points are often on our minds – due to the sheer volume you need when you have to multiply by 4.

Osa: It’s a creative process and an opportunity to bond. It helps that our children also love travel, and are thankfully good flyers.

5) What is the craziest thing you’ve ever done to earn miles or points?

Seth: We spent our most recent wedding anniversary at a Chase branch the day the Chase Sapphire Reserve launched, hoping for a quick approval – but were denied.

Osa: How romantic! But after that we spent the night at a Hyatt without our kids thanks to an annual free night certificate.

Seth: We don’t really do anything too crazy, like manufacturing spend. We earn our points through a moderate number of credit card sign-ups, Bank Direct (which offers AA miles for having an account), mileage mall shopping, and regular spend (with a focus on maximizing bonus categories).

Osa: Correction! Rigorous focus!

Seth: We once earned 10K Delta miles for getting a financial plan – which we actually needed.

Osa: It’s all worth it when I walk off the plane in Hawaii and feel the stress melt away, soak in a thermal pool in a lava field in Iceland, watch rafts of penguins come ashore in New Zealand, zip-line alongside monkeys in Costa Rica, etc.

Enjoying Kauai with the little ones.

6) How does your family feel about this hobby?

Osa: Everyone in our family embraces the hobby. Our kids have now been to over 20 countries.

Seth: When our oldest was 3 years old, she once got off a New York to Los Angeles flight and complained that it was too short. We were in American coach, not Emirates first.

Osa: One time we were fortunate enough to be upgraded on the way to Puerto Rico due to a ticketing glitch. Our 3 year old was so excited that she started to scream “Upgrade! Upgrade!” – only to be shushed by the gate agent because people on the upgrade list would have been upset.

7) Do you ever wish you never found out about miles and points? Why/why not?

Osa: No, our day to day lives are busy. Travel is a fun escape that wouldn’t be possible to the same extent without miles. Miles and travel are also fun topics of conversation.

Seth: True, but sometimes we keep our travels a secret because people can’t understand or tend to judge you. Plus it helps to avoid questions like:

How can you afford to take so many international trips with your whole family?

Is it legal?

Where could you go for such a short time?



8)  If you could give one piece of advice to someone who is just starting out, what would it be?

Seth:  It’s not rocket science – you can do it too!  Figure out your goals, start small, and stay within your comfort zone. Also, it really helps if you can get the Chase Sapphire Reserve.

Osa: It’s obvious, but my #1 tip is to put all your spend on a credit card that earns points. I shared this advice with a novice for whom it made a big difference.

Thanks to Seth and Osa for taking the time to answer my questions!

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Author: Leana

Leana is the owner and founder of Miles For Family. She enjoys beach vacations and visiting her family in Europe. Originally from Belarus, Leana resides in central Florida with her husband and two children.

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4 thoughts on “My Interview with Seth and Osa (A Husband /Wife Team of Points Enthusiasts)

  1. Wow. You guys are inspiring. We’ve stuck with the Western Hemisphere just to keep things from feeling like too much work, and my wife is more of an instruction follower than an equal partner is executing the hobby. It’s nice because it keeps one of us a bit more normal — her obviously. So to have both spouses working on this, and to have such far flung places you prioritize sounds like a ton of work!

    I have a question. I think leana is trying to get at this with two of her questions. Looking back, what has been the opportunity cost of your focus on churning, earning points, and frequent travel? Is your yard a mess? Are you not making it to the gym as often as you’d like? Are the dishes piled up, the laundry always a bit behind? While you haven’t paid any interest, would you say you’re maybe s bit more behind on college savings or retirement than you’d like to be? There’s a cost to what we do. I’m curious to hear more about this, especially from a family as invested in this as you guys.

  2. @ Cheapblackdad

    We’re definitely partners. I too feel like I give a lot of instructions, and Osa indulges me the best she can.

    Osa tends to be more interested in the destinations, accommodations, and activities, while my angle is getting the points and booking.

    I see how it could seem like a lot of work, but we’re in a little bit of a “repeat phase” with our trips – there are a few areas we particularly like (New Zealand, Italy, Hawaii) and we’re happy to go back. It’s not like we’re backpacking in the Himalayas with small children.

    I get your question about the opportunity cost, but we execute the hobby within the flow of our regular lives and consumerism, so I don’t think it’s taken a toll at all. Perhaps the opposite….we get a little out of sorts if too much time elapses between our escapes. Our travels really help to reconnect our family in a way that’s not possible in the day-to-day grind of our busy lives.

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