An Interview with My Reader CheapBlackDad (the Juice Is Worth the Squeeze!)

Most of my readers are familiar with CheapBlackDad, a colorful (no pun intended) commenter and hobbyist extraordinaire. So, I figured it was time to put together an interview so we can all get to know him better. Spoiler alert! He really is black.

This interview was so much fun, even my husband enjoyed reading it. And he hates anything miles and points related, so that should tell you something. Oh, he said that he was looking for a proper moniker to use in Apple discussion boards, and the light bulb went off: Fancy White Dad. Because, Apple, duh!

Anyway, back to the subject of my interview. I actually sent a set of questions to CheapBlackDad (CBD for short), but he added a bunch more. He said I could delete whatever I didn’t like, but how could I? It would be like picking a favorite child. This is a long read, but a good one. Definitely worth your time! At one point, he even addresses me as “son.” Hmm, maybe he was simultaneously putting together a set of answers for an interview on another blog?

Without further ado:

1) First things first. Is Cheap Black Dad your real name? If not, how did you come up with this moniker?

While it’s not my real name, I am a real, live, cheap, black dad. To explain the 3 parts of my nickname: I inherited the cheapness from my Father and Mother, who would make Dave Ramsey cry in shame at his inability to keep up with their cheapness. I also inherited my Blackness from them. And the Dad part my wife helped me with.

2)  When did you realize you were cheaper than everyone else?

College.  That was the first time I got a sense of how other adults managed their finances.  I spent $150 in one semester on food while other students spent that in 2 weeks.  I ate turkey hot dogs wrapped in corn tortillas, and ate free ketchup packets from restaurants if I got hungry in between meals.

 I worked three jobs at once, I bought my clothes from the Salvation Army and rummage sales, and never saw a name brand item in a home I lived in until I had roommates.

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

My wife and I went to Mexico for our 5-year anniversary, and later that year we splurged on a trip to Disney World with our kids. Over the course of that year I also started travelling for work monthly. I caught the travel bug hard.  I began chatting with some of the grizzled vets of work travel while on planes and started to piece together a way to keep travelling to places like Mexico and Disney.

I Googled the mess out of this idea and realized there was a whole community of people who had already thought of this before I had. I think my first blog was Milevalue. I read his beginner’s guide, the Frugal Travel Guy blog, and I realized I had finally found people who thought just like me.  I was hooked.

4) First card (s) in the hobby?

Delta, Arrival and Marriott. Delta was such a noob move.

5) Favorite card?

Chase Sapphire Preferred/Freedom Combo. Haters’ gonna hate, but deep down, you all know it’s the best.

6) Favorite Airline program?

Son, I roll 4 deep when I travel (translation: Good sir or madam, I have a wife and 2 kids and I require the booking of 4 seats as close to one another as possible when I travel). Southwest is a family “go to.” Cheapest redemption options, family-friendly destinations, and they don’t limit the availability of award seats. I am flying them for work a lot more now as well.

7) Favorite Hotel program?

No shame in my game: it’s Marriott. Lots of options for booking, quality across categories, and probably the biggest reason is: I just got started early with them when I was traveling a lot for work. I think Hyatt may supplant them as I start focusing on their program more.

8) Hotel you’ve been to that every family should book on points?

The JW Marriott Orange Lake in Orlando, FL. Best lazy river/pool area at a chain hotel I have ever experienced. Small rooms though.

9) There’s a fight in the parking lot between all the loyalty programs and you have to pick a side and join in. Which do you pick?

Chase Ultimate Rewards. Everyone is screaming SPG: what good is a point if you can’t earn it? This brawl would probably just turn into everyone making fun of the Hilton HHonors program anyways and then realizing parking lot fights are silly and going their separate ways. Shame on you, Leana, for encouraging such behavior.

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10) Program you haven’t dabbled in but want to?

Alaska Airlines. I hear good things, and I’d likely use it for a Hawaii trip. Also, I have managed to do nothing with United, but probably won’t given Chase’s 5/24.

11) Favorite sources of news on the hobby?

Milesforfamily (this blog), Doctorofcredit, Reddit, Frequent Miler.

12) How has this hobby benefited your family so far?

It forces my wife and I to maintain beach bodies for the entire year. Nothing gets me to the gym every day like the thought of people I’ll never meet again seeing me without my shirt on in a tropical environment. 

Can I admit something? I want my children to have this strangely persistent belief that their Mom and Dad are cool. I want them to have this nagging sensation that their parents are awesome when other kids are convinced their parents are lame.  I want to be the one to introduce them to their most memorable moments.

And, selfishly, I want to experience the world in a way I didn’t get the chance to as I grew up. We’ve made so many deposits in the “Good Memories” investment account that I think we can live off  the interest for a few years.

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

I lived apart from my wife and kids for 6 months as I moved to a new job. I used the 4,500 Avios route between Chicago and Cincinnati to visit them regularly. I think I’m the reason they shut that down.  Runner-up is the 2-week family trip we did to Puerto Vallarta, Cancun, and Disney World to celebrate my wife graduating from college after 11 years and 2 kids. The 2nd runner-up is the Disney annual pass we bought with points.                              

14) How often do you think about miles and points? Be honest. 

Every day, but the real question is how often I research the Hobby and potential trips. That’s at 5 days per week.

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

 Relative to other Hobbyists, I am not a risk taker. I don’t do crazy. But I did sign up for the AA Executive offer of $10k/100k miles while trying to meet the minimum spend on 2 other cards. I will never incentivize our family to spend $12k in 3 months on credit cards again.

We did it, and it has allowed us to leverage American/Avios extensively over the past 2-3 years for our strategy, but it taught me that one of the pitfalls of this hobby is how it incentivizes spending and discourages saving.  

16) Did your wife ever threaten you with divorce if you made her switch yet another card?

My greatest fear is that I screw something up and mess up my wife’s credit. She’s placed a lot of trust in me, and she is a huge proponent of what I do.

17) Do you ever wish you’ve never found miles and points hobby? Why/why not?

I have saved 10s of thousands of dollars on our trips. But I also spent money I would not have otherwise spent. Sometimes I think I focus more on what I’ve saved than what I’ve spent. That’s dangerous. I do wonder what our net worth would be if I took that money I spent on trips and instead put it towards investments or paying down student loan debt.

18) What’s your dream trip?

Hawaii or Bora Bora.

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

Pick your spots. Literally and figuratively. Some people apply for 30 cards in three years, and do shameful things for points. Figure out your risk tolerance, travel goals and work/school calendar, and determine what type of churner and traveler you are.

I see so many great trip reports on Europe, Oceania, Africa, Australia, Asia, and I can’t wait to go there some day. But for us? North America, the Caribbean and Hawaii are all we do. We don’t need as many points that way, and those seem to be the safest places on earth for this decade or so.

Bottom line

Well, I hope you all enjoyed it as much as I did. In fact, I’m thinking about doing this type of interview with other readers  now and again. If you want to participate, shoot me an email,  and I will be happy to feature you in a post. I think it’s neat to get to know other families and ways this hobby is benefiting their lives.

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Author: Leana

Leana is the 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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21 thoughts on “An Interview with My Reader CheapBlackDad (the Juice Is Worth the Squeeze!)

  1. That was awesome. Loved it. The point about incentivizing spending was spot on. I didn’t realize it until I read it. Well I did but y’know, kinda ignored it. You must be very disciplined not to spend extra because “I get 5X points tho so it’s cool”. ?

    • Everyone is born with a superpower, and mine is an effortless ability to spend as little as possible. But this hobby strips me of that ability. It’s like kryptonite. We haven’t done anything stupid or dangerous, but I’ve learned that in personal finance just fine is the enemy of great. I’m definitely slowing things down a bit to focus more on the fundamentals of our finances, which are just fine, but not great. So, instead of 4 trips, just 2 a year ;).

  2. Cheapblackdad, I think I got you beat on your cheapness during your college days. I was determined to survive on my tiny monthly scholarship (and I do mean tiny). So, I bought fat instead of meat and fried it to go with cheap pasta. It was truly disgusting!
    Anyway, when all the kids got help from home, I actually once brought free food via train to give to my family. There was a student food program which no one took advantage of because it appeared too complicated.
    People don’t like to jump through hoops, so… I looked into it and found a way to (legitimately) load up on tons of almost free groceries through University cafeteria. I was a food hacker back in my younger years!

    • Yes. You win. And this is definitely a contest I am happy to take runner up in! My turkey hot dogs were quite tasty.

      I think I read on Mr. Money Mustache or some other personal finance blog that what you did is the cheapest way to do food. I think specifically he or she mentioned lard. Pure caloric intake and fat for satiation at rock bottom prices. I haven’t resorted to that, but I’m impressed to meet someone who has.

    • We bought a 5 day pass with an Arrival + at and then added on the annual pass portion at guest services and put that amount on the Cap one card. Free entrance for a year to WDW. Good times. I may write up a post on doing Disney on cash, and another on post if I feel I have something different to add relative to what you can already find out there.

  3. But still such a Newb. There is no favorite programs, there are no favorite credit cards. There is only long term strategy. And Caribbean as a safe place…a long long way ahead of you.

    • …and there is no spoon.

      Agreed tho. I feel like a complete newb even after 3 years of doing this. A lot to learn.

      I do think this speaks to a key difference between how I do this and how a lot of others approach the hobby. I toss issuers a bone. I try to keep open at least one card with each issuers to ensure when they check my report or history they see some value and history in my relationship with them. Not sure it’s helped, tbh, but it’s part of the long term strategy.

  4. Great interview! I especially loved “We’ve made so many deposits in the “Good Memories” investment account that I think we can live off the interest for a few years.”. That’s exactly the reason we do it! Thanks, Leana!

  5. Good interview, could be a nice series! #17 is a good point. I have mostly looked at miles/points as a discount mechanism, enabling me to visit far off places and re-allocate what I would normally spend on a vacation in a different way. For example, it’s rare that I would take a trip to Europe and have 100% of my hotel and airfare covered by miles/points. It’s usually one or the other, probably airfare more often than not. Part of this is due to the places that I visit or the fact that we are traveling as a family of 4, which consumes a lot more miles/points. In the past as a couple, we had more trips where the air + hotel were completely covered for free. When one part of the vacation is covered gratis, I’m probably spending more on the memory-making part – that could be something like a more luxurious hotel or an activity, attraction, or nice restaurant. I totally identify with the “Good Memories” investment mindset.

    • @Erik If you are interested, I would love to interview you as well. Let me know, and I’ll send you a set of similar questions (minus the “cheap black dad” nickname inquiry :))

    • I budget any spending we do on a trip as incremental. As in, I would likely not have done this without the assistance of points. You can see how that really makes this hobby look expensive in our household budget as opposed to your discounts approach.

      I think that should probably change now that we are comfortably ensconced in the middle class and vacations are a way of life. I should likely adjust my budget to reflect some amount per month towards a vacation fund. Having very little money early in life leaves a lasting impression on one that is hard to shake, and I think it has led to some ineffective financial tactics as we’ve moved up the economic rungs. It’s probably time we adjust our thinking.

  6. Great interview! I can especially relate to this: “I have saved 10s of thousands of dollars on our trips. But I also spent money I would not have otherwise spent.” I struggle with this all the time! I get so excited to book a “free” trip but then I still spend more money each year than we should on vacation food, airport parking, pet sitting and touring around.

    The only thing missing from this interview is a family picture! 🙂 Maybe next time.

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