As freelancers, many of us crave the freedom to explore new places without the financial burden that travel can bring.
But what if you could fly in luxury without spending a fortune? That’s where points travel comes in, and today’s guest is a true expert in this game.
Spencer Howard, the mastermind behind Straight to the Points, has helped countless people book premium travel with points instead of cash—making dreams of business and first-class travel a reality.
In this episode, Spencer shares his journey from a political career to building a freelance writing business to becoming a full-time freelancer in the world of points and miles. He dives deep into the strategies freelancers can use to leverage credit card rewards and optimize points for travel, breaking down complex topics like transferable points and airline-specific credit cards.
And he explains how to do this without getting into debt or paying credit card fees that don’t make sense.
I learned a lot from this conversation. I realized that many of my hang ups about points travel were unfounded. And I discovered that I’m actually making some pretty big mistakes with a strategy I assumed was getting me huge travel perks (but it’s really not a great value!).
If you love to travel, you’re going to find several actionable tips on how to maximize your points, avoid common pitfalls and plan your next dream trip—all without breaking the bank or getting into debt.
Enjoy!
The notes that follow are a very basic, unedited summary of the show. There’s a lot more detail in the audio version. You can listen to the show using the audio player below. Or you can subscribe on Apple Podcasts, Spotify, Stitcher, Google Podcasts, Amazon Music or wherever you listen to podcasts.
Key Topics and Bullets:
- Effective strategies within the points and miles
- Key rules: avoiding debt, timely payments, and annual fee
- Dispelling myths about negative credit score
- Simple strategy with a few cards for bonus
- “Hub and supplement” with several
- Maximalist approach with many sign-up
- Keeping oldest cards active for credit score
- Rapid point accumulation through sign-up
- Prioritizing flights over hotels for point
- Using points for hotels selectively and paying cash for car
- Emphasizing credit card spending as a primary earning
- Shift from flying-based to spending-based rewards
- Reassurance about reliability of award ticket
- Tools for managing travel plan
Timestamp Overview:
00:00 Ed– I am very intrigued by today’s topic, and it’s something that I’ve definitely taken advantage of. You know, this idea of rewards travel, we’re gonna kind of get into the weeds with this. But before we do that, why don’t you tell us a little bit about yourself, what you do? And I’m curious to learn how you got here. You know, what’s what’s the
Spencer– So my website is called Straight to the Points. I send out basically flight deals, but instead of cash deals, I send deals you can book with points for premium cabin business and first class on international routes. And I just kind of break down the options for booking, give you the dates, and kind of really dive into the weeds on, like, why you would use one set of points versus another set of points since we have so many options here in the US. That’s the gist of what I do now. It was the evolution of writing about loyalty programs and points and miles for several years before I started my own business. I was a freelancer, writing for lots of websites, and that was after about 10 years working in politics.
05:30 Ed– Let’s talk a little bit about maybe the categories of opportunity. So we’ll start with broad strokes, and then we can kinda drill down and get in the weeds. But what are some of the biggest opportunities in terms of using or leveraging credit cards to get rewarded with travel?
You know, whether it’s airfare, upgrades, experiences. So kinda let’s Yep. Give us a lay of the land.
Spencer– Sure. I think sometimes there’s this idea of like, oh, can I just use points for anything? And banks and airlines will try to give you lots of opportunities to use points. A lot of it’s just understanding what the best ways are. And, typically, it’s like if you have airline miles, booking flights is the best way. If you have hotel points, booking hotels is the best way. There are the rare exceptions, but a general rule, that’s just kind of where I start from. Similarly with banks, if you have points that can be transferred to different airlines, that’s generally better than, like, cashing them out for gift cards or cashback. And it’s just that’s what they’re really meant for.
08:18 Ed– Well, since we’re talking about credit cards and banks, maybe we can start there. So there’s obviously bank credit cards, and then they are partners with different airlines that you can choose from. And there are also airline specific credit cards. Can you maybe give us the pros and cons of each type?
Spencer– Yeah. Sure. I’m a huge fan of transferable points, which is a bank’s own program, just because it gives you flexibility to use a variety of airline programs. When you think about award space, it’s different than a cash ticket. Like, an airline’s just if you wanna pay cash, great. Buy a seat. If you wanna use your points to get a ticket, generally speaking, they’re releasing a couple, a few, maybe none at all depending on the day. And so it’s not as straightforward.
11:41 Ed– With my particular credit card, I get lounge access. And all it took was for me to go to the lounge one time, I was sold. Like, this is so much better than waiting at the gate. Upgrades, you know, I frequently get upgraded to the next level, whether it’s comfort plus or to 1st class.
And, so for me, it really makes sense. I don’t travel that much. You know, maybe maybe once or twice a quarter. So it’s, but, you know, somebody else who may not live in a huge hub like Atlanta for an airline may need a little bit more flexibility. That’s not as valuable for me. Yeah. So, yeah, I get it. It makes sense.
Spencer– If let me let me give you some context for Delta. And this is why I I often joke that Delta’s never gonna work with me because I say things. But if you wanna book, like, let’s just say you wanna go to Europe, and you wanna book a one way business class award ticket, and you let’s say it’s on Air France from Atlanta to Paris. It’s 50,000 flying blue miles plus about $250 in taxes and fees. If you were to book that same ticket with Delta SkyMiles, you’d be around 305,000 SkyMiles plus about $5.60. So to save $250 basically, you’re using an additional 250,000 points, which is worth way more. Wow. Like, like, it’s just it’s staggering.
15:09 Ed– Deals are coming up. I want to ask about other misconceptions, common misconceptions you hear when it comes to reward travel.
Spencer– Yeah. I think the biggest one is that airlines brand themselves as having frequent flier programs. That those days are kind of over. Like, sure. You can earn points by flying. You can earn a lot. But the real game is now with credit cards. It’s where you spend.You can get sign up bonuses. You can use bonus categories of credit cards. Excuse me. And it’s just it’s more I always call them airline programs. It’s less about flying a lot. It’s more about just using any products that can allow you to earn points. You can use shopping portals. You can link dining programs or extra points.
17:40 Ed– There are other fees, not just interest. So 20 credit cards. Most credit cards these days have an annual fee. Yep. Tell me about that because you could end up paying a ton of money in annual fees, which I’m sure is not the case. Talk to us about that.
Spencer– So I will also say that you don’t have to be like me. I’m obsessed. Like, if you have friends who play golf, some go to the driving range, and they go to putting green, and they’re practicing, and then they play with you on the weekend, and you basically drink a beer and see what happens. I’m the person who practices, and not everybody has to be like that, but we can all have fun and figure out, you know, what we wanna get from this game. So for me, yes, I pay more annual fees than most people, but I’ve spent the last 7 years traveling 3 months of the year, 3 plus months. So I get value out of all these cards. Every year that I have an annual fee come up, I just run kind of a cost benefit analysis. Like, is this annual fee giving me more than it’s worth or more than the annual fee in value? And sometimes it is, but it’s too close.
20:35 Ed– Well, let’s work with that a little bit. I there’s there’s a limited amount of money you’re gonna run through 1 or all of your credit How can you, generally speaking, maximize the value and the bonuses when you’re gonna only gonna spend a certain amount every year? Like you said, we’re not gonna overextend ourselves. Yeah. And and if you abandon one to now kinda take care of the other so you can really get the value from it, you know, are you not cheating yourself out of the bonuses or the potential value of the one you abandoned?
Spencer– Yeah. So you’ll never earn points faster than when you get a sign up bonus is the general concept. So a lot of these cards, it’s like, you know, earn 75,000 points if you spend $4,000 in 3 months. So if you just repeat that process every 3 months, you’re earning 75,000 plus whatever you earn on the actual spend of that $4,000. So you’re at bare minimum coming out with 79, 80,000 points every 4 months, or 3 months. Excuse me. If you were to not get another new credit card and you just kept spending on the card you had, you’re gonna be earning anywhere from 1 to, say, 4 dot points per dollar, which is great, but it’s not the ratio.
Like, if you do 7 if you think about 75,000 points for $4,000 in spend, you’re earning significantly more that way, which is why people like sign up bonuses. So if you’re somebody who’s, like, good at keeping a spreadsheet or there’s some apps that’ll help you keep track of things, you can just kind of work your way through. I think a lot of people, what they end up doing, some people get excited and go for a bunch of cards at the beginning, and then they come back to as they find keepers, the cards that make sense for their spend and travel habits. Like, you have lounge access with your card.
22:47 Ed– Tell me about the impact to your credit, not in terms of having multiple cards, but if you’re going to follow a similar strategy where every 3 to 6 months you’re applying for a new one for the sign up bonuses, you get ding for a credit inquiry. Is a ding not big enough that it’s a kind of something to take into account?
Spencer– That’s generally what I’ve noticed in the last, you know, 8 years that I’ve been doing this is, like, you’re gonna get a small hit when you do the application. And then within a few months, it just it comes back and bounces back. And then a lot of times people find that especially when they’re newer to credit, as they get more credit line, their credit score actually improves, because their utilization rate drops. More credit available, but you’re still spending the same amount of money, and so the percentage of your credit being used is lower, which is you find that which is good. Yeah. They like that. I don’t make the rules. I think sometimes I think the way that scores are calculated is kind of silly, but, it’s just again, I don’t make the rules.
28:21 Ed– Like, because it wasn’t just wear on the plane, but it was also the level of economy and what that included. It just became really, really overwhelming fast.
Spencer– I think airlines and Delta’s actually done this as well where they just, like, they break out fares. So it just used to be economy. Now it’s basic economy, main cabin, comfort plus, and, like Yes. And that’s all within economy. And so it’s I think not every airline, I guess, but a lot of airlines have gone that direction where they have unbundled things. So it’s like, do you get a check bag or don’t you get a check bag? Do you get a seat? Do you get to select your seat or don’t you get to select your seat? And that’s become pretty standard, and I think you’ll see similar things across airlines. Generally, they’re pretty good about breaking out, like, what is included. I will say that I’ve run into things where, like, actually, Air France actually listed what’s included incorrectly, and it was just kind of a known glitch, which is so and it was like, you don’t get a seat selection.
29:41 Spencer– It’s all new for them, But it’s, again, it’s not as bad as I think people fear. It’s more just knowing how to go through the steps knowing that you know, if you’re canceled and you have the, say, you have your delta, you on the app, you can just rebook your flight on the app. You don’t have to go to somebody necessarily. If the app doesn’t show your flight that you wanna be moved on to, of course, you can. You can go talk to somebody, but, generally, they’re pretty good about it. So it’s just it’s more about learning to use the tools that you have in front of you. Are a lot of… most airlines I can’t even think of an airline that doesn’t have an app right now, but especially that you’re gonna fly with points? So, yeah, I get the anxiety. I think the differences between the carriers aren’t big enough to, like, or just to make you not, book something.
33:49 Ed– What are for somebody who’s really interested in doing that, what are some really good options for that?
Spencer– Yeah. Travel freely is a great app. There you can enter the as you’re getting cards, you can enter them into the app, and it would and you can set, like, when you opened it, and they’ll remind you when you have an annual fee coming due. You can see, you know, like yeah. It’s just it’s a good way to track. And, yeah, that’s just how I do it. Actually, I don’t use travel freely myself that much because I just seem to remember things, but I know for most people, it’s a lot of information. So I think travel freely is good.
38:53 Ed– Well, we haven’t really talked about this, but I guess if you could, I don’t think we have. Resorts, hotel stays, you know, car rentals, and all that. Do you generally advise people to use award points for that, or is that typically better, funded through cash?
Spencer– So I would say there are some circumstances in which hotels make sense. Car rentals, not as much. With hotels like Hyatt has a good program where they have what I consider reasonable redemption rates, and you can transfer points from, like, Chase ultimate rewards or built rewards, and those are really easy ways. Again, you’re able to earn transferable points and then move them over to Hyatt. Hyatt or excuse me. Hilton, IHG, Marriott, there are some banks that transfer there, but the number of points that you need to book typically makes them a pretty bad deal for transferable points. If you just happen to have IHG, you know, Hilton Marriott, like, go for it. Use your points.
40:28 Spencer– So there’s, like, Amex and Chase both have Marriott cards. Chase has Hyatt cards. Chase has IHG cards. Amex has Hilton cards. So there’s a lot of that. I just generally don’t suggest people prioritize that, over, like, transferable points. I I think the vast majority of people benefit from starting with transferable points and then kind of expanding as needed. But, again, it’s just how deep into it do you feel like going. If you’re gonna keep it really simple, like, do transferable points with cards that will help you earn the most points based on where you spend, and then just roll with that. There will be cash involved in traveling. I always tell people that you’re not gonna, like, travel for free. The goal to me, the goal is the experience. The point of points isn’t to say that you did something for free. You can stay home and get a book from the library if you’d like free activities. It’s a great option.
42:59 Ed– Any parting thoughts before we sign off? Anything that we didn’t talk about that you feel is important and people know?
Spencer– I think just have fun with it. I realized that I like, you know, I’m a little extreme with points. I’m obsessed. I get that. But it’s fun, and you find your kind of sweet spot. You and I think everybody over time figures out kind of where they fit in this points world. It’s kinda open to a a lot of us. I’m not gonna say anybody can do it.
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