Thanks for reading Finesssing Finance. Your support is recognized for fueling my journey to help people with free, accessible personal finance content. This week, I had the opportunity to interview Jonathan Jacobs and gather his thoughts on his many travel adventures plus how he maximized the value of his trips.
Introduce yourself (Name, Age, Occupation, Hobbies)
Hi there! My name is Jonathan Jacobs, and I split my time between Florida and California. The most important fact about me is that I’m a Delta Air Lines Million Miler and Diamond Medallion, but it’s also probably helpful to know I’m 31 and work in marketing. For a decade I co-ran my own agency before selling that and taking some time off, which I’m now currently enjoying. For the purposes of this interview though, having my own company was certainly a key reason I was able to build the travel resume and knowledge base I have today. When I’m not in the skies, I fill my time cooking, reading, writing, playing golf, and spending time with my friends and my dog, Luna.
How did you get started with traveling and using Credit Card points? Tell us about your most recent trip.
I grew up with incredible privilege, which meant that flying has always been a part of my life. We didn’t fly private or first class on the regular or anything, but we were lucky enough to take a few family trips each year. All that to say I’m not sure exactly when the switch flipped in me from recreational traveler to hobbyist. Certainly starting my company and beginning my career played a role in that, but I think I really got into this hobby around 2014-2015. That’s when I really started to expand my knowledge base about personal finance and credit cards. By 2016 I was mileage running, churning, and going to international conferences about credit cards, points, and miles. I’ll punt on the second part of this question because it’s my answer to the next one!
What’s been your biggest trip and how did you use your points?
I'm lucky to have taken some really exciting trips in my time (like flying Lufthansa First Class and the Singapore Suites), but I think one of the most special was the trip I just took this summer to the UK, Tanzania, and Jordan. An odd trio for sure, but the UK was my gateway city, I was heading to Tanzania to visit an old friend, and Jordan has always been #1 on my bucket list. The trip was everything I could have hoped for, and took me from sailing around Zanzibar to the red sand of Wadi Rum. Before I even left Jordan I was dreaming about going back! (Learn more about the trip on my TikTok)
Points were integral to my trip. I used them for almost all of my airfare and many of my hotels. For example:
To fly Turkish Airlines Business Class from Amman to London, I redeemed a points balance I had with Bilt Rewards (you can earn points when paying rent with this no-fee card) by transferring them to Turkish Miles&Smiles.
To fly Emirates First Class from Paris to Dar Es Salaam, I transferred a points balance I had been saving up with AMEX to Emirates Skywards. Still had to pay $900 in taxes and fees, but this airfare would normally be $3,500+!
To fly Qatar Airways from Dar Es Salaam to Amman (economy class). I redeemed some points from my American Airlines AAdvantage account.
To Stay at the St. Regis in Amman, I used Membership Rewards points and booked via the AMEX portal. Because I have the Platinum Card, I also got perks when doing so because the St. Regis is a part of AMEX's Fine Hotels and Rewards network.
Are there any travel credit cards you recommend?
I'll do my best to answer this question, but I do have to say one thing first. Not every card is for every person. We all have different travel goals + dreams, spending patterns, and resources to commit to this hobby. So I'm going to tell you my three favorite cards right now based on what fits my needs as a traveler. Again, these cards might not make sense for you!
Capital One VentureX: This is, hands down, my favorite card on the market right now. It offers a baseline 2x on all transactions, which is superb. Yes, you can find that with a few other personal cards, but those tend to focus on cashback rewards and not transferrable points earning, which Capital One miles are. On top of that, you get 10x on hotel and rental car bookings through Capital One, and 5x on flights. There's also a $300 annual travel credit, Priority Pass membership, 10,000 miles gift on your renewal date annually, TSA/Global Entry credit, and more...all for a $395 annual fee. It's the most competitive premium card on the market. If someone is going to get just ONE card, I really think it's worth considering this one.
American Express Blue Business Plus: If you're an AMEX loyalist, this card is a must-add to your portfolio. It offers 2x on everything up to 50K$/year with NO annual fee.
Chase Freedom Unlimited: A notable product from Chase which offers 1.5% on everything. But for no annual fee, you'll also earn 5% on travel booked through their portal, as well as 3% on dining and delivery, and drugstores. While I tend to use my American Express Business Gold for dining (I earn 4x there), I tend to make frequent drugstore purchases, so this is a nice little bonus category for me to have. And since I can hang onto this card for no annual fee, it's a no-brainer!
Honorable Mention: The American Express Platinum Card. I have to include it, right? It's a great card, just not for spending. I hold this card for the perks and benefits, not my everyday spend. Centurion Lounge access, SkyClub access, and the Fine Hotels & Rewards program see a lot of use from me.
What tips do you recommend for someone looking to travel on points?
Never assume the best deal is the published one! There are lots of different offers for a credit card active at a time. There might be a published deal, a targeted one, and a referral/affiliate one. Before applying, always check the offer you can find via search (browse BOTH in public and private mode), see if a friend has a referral link, and use a tool like Cardmatch.
Build up your balances in transferable point programs! More on that below.
Have an objective from the get-go. We've all heard the phrase "start with the end in mind," right? This hobby is no different. Don't amass points for the sake of doing so. Do it so you can go see the world, your family, your friends, etc.!
What are some things to avoid when booking a trip and using points?
First and foremost, never move points out of a program until you are ready to book and confirmed availability. For instance, if you were looking to book a flight with United Airlines by transferring Chase Ultimate Reward Points to United’s loyalty program, don’t do so until you have gone to the United site and confirmed the space is available! Once you move points out of Chase (or AMEX, or Citi, or Capital One), they can’t be sent back. You’ll have to keep them there until you can find a use!
Secondly, and this might be controversial, but I discourage you from building up your points balance in airline and hotel specific program (like Delta SkyMiles or Marriott Bonvoy). These programs are currencies run and manipulated entirely by these corporations. The value of a point or a mile is completely up to them. Round trips flights to London from JFK might be 50,000 miles on Tuesday, but an overnight adjustment means they’re suddenly 100,000 on Wednesday, and now the “value” of the balance you’ve built up is half of what it was the day before. Instead, building up your balance in a transferable points program means you have the flexibility to move your points around to find the best deal.
Do you have any noteworthy travel destination experiences?
I'll give you my top 3, omitting my recent Tanzania/Jordan trip and Emirates flight since I already mentioned those:
The Lufthansa First Class Terminal in Frankfurt. First Class passengers don't just have their own lounge, they have an ENTIRE terminal to themselves, with dedicated security, shopping + more. The food options are superb, and there's even a dedicated whiskey and cigar bar. When it's time to board, they drive you over to your plane.
Visiting Taiwan and Taroko National Park. This was my first time to a cloud forest, and it was such a unique experience, filled with peace, serenity, and nature. My travel buddy and I also met some great people while we were there, who we continue to keep in touch with.
Visiting Iceland in 2015 for a road trip. We were on WOW Air's inaugural flight from the US to Reykjavik and we felt like we got to be among the first in this wave of American tourists to visit the country. We spent about ten days exploring everything Iceland had to offer, and I was awed by the sheer diversity of the topography there, and the kindness of everyone we met.
Which airlines do you personally recommend and why?
If you follow me on TikTok or Twitter, then you probably know that I am a Delta Air Lines loyalist. I'd say 90% of my flights each year are on Delta, so much so that I'm both a Million Miler and a Diamond Medallion. For business travelers I always recommend Delta, as I think they treat their elites the best of any airline, and have a reliable product with some of the best people in the business. But I'll be honest, if you don't travel for work and only travel a few times a year, chase trips not airlines. Go with the most affordable, comfortable and convenient options.
But if you're asking what airlines I think everyone should experience at some point, I'd single out Emirates, Etihad and Singapore.
Do you plan on continuing to travel throughout 2023? What are the best times of the year to travel? How have you secured great travel prices in the past?
Absolutely! I’ve already got trips booked to Mexico City, Tahiti, and a few domestic trips for weddings.
I’d say there really are no best times of year, or even day, to travel anymore. The past two years have already re-written the few “rules” that may have existed. For instance, whenever possible, I would try to fly “off-peak” in the past. Think Tuesday instead of Monday, or early mornings instead of afternoon and evening. Doing so was a way to increase the odds you might get an upgrade as an elite member as the loads were usually lighter on these flights (fewer business travelers as they have a pretty standard schedule). But now there are fewer flights and more elites, so that logic has gone out the window. And as far as time of year, any time is a good time to travel. All that matters is being attuned to what that time of year means for the destination you’re visiting. Is it monsoon season in Sri Lanka? Will they be observing Ramadan in Jordan? Is it winter or summer in Australia? You just need to be dialed in to what type of trip you’re looking to have, and if this is the right time of year for that based on local factors.
What are your final takeaways from being a travel points expert?
Hm. I think there are two messages I'd love to leave people with.
Remember that this is a hobby. Generating points and earning free travel isn't something done with just a few credit card swipes. Like any other hobby (knitting, golf, basketball, cooking), your results are a function of the time you invest. What am I trying to say here? Don't expect to fly First Class around the globe just because you opened a Chase Sapphire Reserve card. Understand that if you're not willing to commit the time and/or resources to this hobby, you can't expect the same results as someone who does (me).
Unless you're a regular business traveler, I would encourage you to move away from a quest for elite status. Airlines are making it harder and harder (or at least more expensive) to pursue top tier elite status, putting it out of reach for many everyday travelers. Striving for elite status might require a lot more investment of time and capital than you're ready to do, for benefits that are often not worth the cost.
Thanks for reading Jonathan’s words this week.
See you in the skies,
Jordan