Unlocking Luxury Travel with Credit Card Points: A Conversation with Spencer Howard

Unlocking Luxury Travel with Credit Card Points: A Conversation with Spencer Howard

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Welcome back to The Daily Mastermind. George Wright III here with your daily dose of inspiration, motivation, and education, and I'm joined by a great topic. This is going to be really fun.

I'm joined by Spencer Howard, and I'm going to give you a quick background on him. He's a credit card loyalty and travel reward expert. He's the founder of a company called Straight to the Points, and he teaches strategies behind how to use your business card to create a luxury travel lifestyle.

But he's been a travel writer and editor for over a decade, featured on podcasts and outlets. What I loved about when I saw his background is he travels three months per year to 60-plus countries. So welcome to the podcast, Spencer. How are you?

Thanks so much for having me. I'm doing well.

Yeah, this is great. This is a good topic because, as people know me, they know I'm all about mindset and business and money, but lifestyle is the whole point of it.

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Spencer Howard's Background and Journey

So tell us a little bit about your story. I'm curious about your background, but more importantly, what settled you into this niche of luxury travel?

Yeah, for sure. I actually used to work in politics, everybody's favorite industry. It’s crazy, but towards the end of that, I picked up reading a blog about points. I was like, “Oh, points? What are points?” I dove into it, and the guy was like, “Oh, I fly business class with points.”

I thought, “I’m six-three. I’d love to lie down.” I think I had just booked a flight to Japan in economy, and my knees were going to be in the back of the seat in front of me. I needed to do this better. That was the jumping-off point for me.

Had you been traveling already? Your whole life? Or not really?

Not a ton, but it was something I always wanted to do. When you work in politics, you don’t really get a lot of time off. It’s all on the work side, not a lot of lifestyle. Towards the end of my time in politics, I started having a little more time to travel, and I just made figuring out the best ways to do it a priority.

I spent four hours a night for six months learning everything you could never want to know about airline programs and credit card fine print. Now I basically just say, “You don’t need to do that. I’ll do it for you.”

That’s awesome. And this is credit card travel, but you’ve been blogging and writing. Was that writing and blogging in this particular topic that you were learning, studying, and growing on?

Yeah, about nine months after I got really into this, I started writing part-time, just freelancing. I picked up enough writing to leave my previous job and start a new career path. It was all educational writing. I’d say I’m not very good at clickbait, but I’m really good at breaking down complex topics and making them understandable. That’s been my focus, and it’s what I still do now with my email newsletter.

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Turning Passion into a Business

At what point did this turn from an interest to a business for you? What made you decide, “I like this. I want to make this a business”? Because at the end of the day, I’m sure a lot of people are like, “There’s a lot of things I’d like to do; I’m going to study them, really get into them, maybe even write—but how do I monetize it?” So, at what point did it turn into a business, and did you see initially that there was an opportunity with it? Or was it just, “I think I can do this, and I want to focus my time on it”?

At first, it was freelance writing. I just had contracts with different sites to write for them, and that was easy enough. I guess about two years after I started writing, I started my email newsletter as a hobby.

I think I was looking for a flight and noticed something rare—an opportunity to use points for a business class flight. I mentioned it to a friend of mine. I said, “I do all this research for the articles I’m writing. I should just send emails out when I find something worth booking.” He was like, “Do it right now. I’ll sign up. Do it.”

I started an email list the next day.

That’s great. And it’s really funny you say that because I think a lot of people dabble. I’ve got this interest; I do some things. But I’m going to make an interesting point to the listeners: four hours a night for six months. You really studied it. You got to know it. You went deep, right? I think most people dabble when they should go deep.

And then, a couple of years of freelance writing, you decided to do a newsletter. Why did you choose a newsletter? Just because you were already a writer and thought, “That’s a great way for me to kick out my ideas”?

Yeah, it’s funny because I remember in 2018 hearing people say, “Oh, email newsletters are dead.” I thought, “Okay, that’s fine. I like blogging.” This felt a bit more curated. I’m only going to talk to people who are interested in what I’m interested in.

You’re not signing up for my newsletter if you don’t care about flying business or first class, or traveling abroad. It was a way to ensure I was reaching people who had committed to me. It gave them an advantage over others who weren’t aware of these opportunities.

I think that’s great. And it’s really interesting because I always love interviews like this. It shows that success is pretty consistent, and principles are consistent. You found something you were passionate about, worked on it, went deep, and focused your time. You also drilled down into a niche.

When it comes to luxury travel, was that because you saw the opportunity, or because it was what you were focused on personally, so you decided to stay in that vein?

Yeah, for me, it started because I love flying. If I can make the journey fun, that seemed like an awesome way to do it. This is just what I cared about and what I was interested in doing.

I would still be supportive of someone who wants to use points to fly economy around the world. That’s great, have at it! But for me, I like flying. I thought it would be fun to have champagne while flying, to lie down, nap, have a better meal, and go to a nice airport lounge.

That’s what mattered to me. Not everyone cares about that, and that’s great, but this is my little circle.

And you and I talked a little bit about this. Not everybody believes they can do it. I think many don’t believe they could ever afford it or have enough money on their credit card to make it happen. Plus, I don’t think they know where to start or even if it’s possible. Have you run into that? What do you say to someone who doesn’t think it’s possible?

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Strategies for Maximizing Credit Card Points

Yeah, I think, especially with points and credit cards, people often see credit cards as dangerous. I’ll readily admit they can be, but only if you’re not in a good financial position or not responsible with your finances.

I always say this is an extra to enhance your life—it’s not the key to your life. If you don’t have a 700+ credit score, maybe even 720+, if you don’t pay your credit cards on time every time, or if you feel tempted to overspend because you have available credit, this isn’t the world for you.

That’s fine. I just don’t want anyone to experience financial hardship because they decided to play a game. In the end, this is a game. It’s fun.

But after that, it’s about piecing together a strategy. It’s like a puzzle: Which credit cards work best for you based on your spending habits? Many cards have bonus categories that earn two, three, or four points per dollar instead of one. It’s just about finding a strategy that fits your interests, time, and energy.

I love that. That’s the case in point for so much in life: intentionality. I also agree—this isn’t about encouraging people to use credit cards irresponsibly. It’s about leveraging a strategy. You said something interesting: This is a game, but it’s a strategic game. It sounds like you’ve really hacked the model to fit for people.

It’s not a game for winging it. You can be spontaneous with it—book a last-minute trip when you find a ticket you can book with points. That’s fun. I’ve booked a flight six hours before departure and gone to Europe.

But to get there, spreadsheets have been involved. I’m really good at tracking things, and a lot of people in this space are. We’re very aware of where we’re spending, how much our annual fees are, and whether we’re getting more value from a credit card than its annual fee. We’re constantly thinking 10 moves ahead.

That makes sense. For someone thinking about getting into luxury travel with credit card points, are there certain spending levels that make it feasible? Or is it more about applying a strategy, regardless of spending levels?

If you’re spending around $1,000 to $1,500 a month, you can probably do something meaningful. But it all comes down to your level of interest.

I usually say there are three strategies with credit cards. First, there’s the “set it and forget it” approach. You get one to three cards with bonus categories that earn the most points on your spending. A lot of business owners do this.

Then, there’s the “add-on” approach, where you start with four to six credit cards and supplement with a new one every few months.

Finally, there’s the maximalist approach, where you repeatedly get new credit cards. It’s the most work, but you’ll earn the most points. Each new card comes with a sign-up bonus—for example, spend $4,000 in three months, and earn 75,000 points. That’s the fastest way to accumulate points.

Got it. Is this about the credit cards themselves or the companies you’re transferring points to, like airlines and hotels? What’s more important?

My main focus is on transferable or flexible points. Banks like Chase, Amex, Citi, Capital One, and Bilt have programs where you can transfer points to partner airlines or hotels.

Got it. So transferable points open up more options and flexibility compared to sticking with just one airline or hotel chain? That makes sense. Explain a little more about why transferable points are such a great strategy.

Exactly. Transferable points give you access to more flights, more airlines, and better opportunities. For example, if you only have American Airlines miles, you’re limited to flying American Airlines or their OneWorld partners. Similarly, if you only have United miles, you’re limited to their Star Alliance partners.

But with transferable points—say, Chase Ultimate Rewards—you can transfer your points to British Airways, which is a OneWorld partner like American. Or you could transfer them to Air Canada’s Aeroplan program, which is a Star Alliance member, or to Air France/KLM’s Flying Blue program, which is part of SkyTeam.

So with one hub of points, you have access to almost every major airline in the world. This opens up tons of opportunities.

That’s huge because most people don’t realize how limiting single-airline loyalty programs can be. So with transferable points, you’re essentially leveraging arbitrage between programs?

Exactly! And here’s another example to illustrate the value of transferable points. Let’s say you’re booking a one-way business-class ticket to Europe. If you use Flying Blue (Air France/KLM’s program), it might cost you 50,000 miles and a couple of hundred dollars in taxes and fees.

If you tried booking the same flight with Delta SkyMiles, it could cost you 150,000 to 300,000 miles for the same route, even though Delta partners with Air France/KLM. That’s why it’s so important to compare programs.

By using transferable points, you can pick the program that gives you the best value for the flight you want.

That’s a game-changer. I’ve definitely run into the frustration of limited award space with certain airlines, so having options is critical. How do you help clients avoid that frustration?

Award space is always going to be a bit of a challenge because airlines only release a certain number of seats for points bookings. But when you have transferable points, you can search across multiple programs to find availability.

For example, let’s say I’m flying from DC to Europe. If there’s no award space on United or its Star Alliance partners, I could check Air France/KLM through Flying Blue or even British Airways.

Having options is key. That’s why I focus on helping people understand which programs work best for different destinations.

And you mentioned earlier that some people might think this is a lot of work. What do you say to those who feel overwhelmed by the process?

It can feel overwhelming at first, but that’s why I focus on simplifying it. I have a quick-start guide on my website to help people understand the basics. Once you know the foundational principles—like which airlines partner with which programs—it becomes much easier.

I also send out a newsletter where I highlight specific award space opportunities. For example, I’ll send the exact dates when you can book business-class flights with points and break down which programs give you the best value.

Having someone curate this information for you saves a ton of time and energy.

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Making Travel Simple and Accessible

I love that. So it’s about creating a system that simplifies the process and makes it easier for people to take advantage of these opportunities. What are some common myths or misconceptions people have about using credit card points for luxury travel?

One of the biggest misconceptions is that having multiple credit cards will ruin your credit score. In reality, if you’re managing your cards responsibly—paying your balances in full and on time—it can actually improve your credit score.

Another misconception is that luxury travel is out of reach. People think they could never afford to fly business class or stay in five-star hotels, but with points, it’s absolutely possible.

The key is to change your mindset. Instead of thinking, “I can’t afford this,” think, “How can I make this work?”

That’s such a good point. It’s all about mindset and strategy. I love that you make this accessible for people, whether they’re casual travelers or hardcore points enthusiasts. What’s one piece of advice you’d give to someone just starting out?

Start with transferable points. Get a good credit card that earns points you can transfer to multiple programs. That’s the easiest way to give yourself flexibility and options.

And don’t feel like you have to master everything overnight. Just focus on understanding the basics, and as you gain experience, you’ll start to see how everything fits together.

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Conclusion and Resources

This has been such an eye-opening conversation. I know our listeners are going to get so much value out of this. Before we wrap up, can you remind everyone where they can connect with you and get your resources?

Absolutely! The best place to start is my website, StraightToThePoints.co. You’ll find the quick-start guide there, as well as information about my newsletter.

If you’re interested in more hands-on help, I also offer a paid newsletter where I send out curated award space opportunities and tips for maximizing your points.

Perfect. I’ll make sure to include all those links in the show notes so our listeners can easily find you. Thanks again, Spencer. This has been an amazing conversation, and I can’t wait to share it with everyone.

Thanks so much for having me! It’s been a pleasure.

All right, everyone. Don’t forget to share this episode with someone who might benefit from it. And as always, remember—it’s never too late to start building the life you’re meant to live. Thanks for listening, and I’ll see you on the next episode.

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About Spencer Howard

Spencer has been a guest speaker in multiple shows on YouTube touching on maximizing points – Geobreeze, Waller’s Wallet, Every Passport Stamp, and Miles Talk. In addition, Spencer has been on multiple podcasts such as Beyond The Lens podcast, Miles to Memories, and Saverocity Observation Deck where Spencer discussed airline cancellation policies, award trends, and more. He runs Straight to the Points, an award-seat alert platform.

Spencer graduated from the University of Notre Dame with a degree in political science and now works in Washington, D.C.

When he’s not searching for fun award redemptions, you can find him playing softball on the National Mall, watching Notre Dame football, or enjoying a fine bourbon.

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Guest Resources:

Website: https://straighttothepoints.co/

Instagram: https://www.instagram.com/straighttothepoints

Linkedin: https://www.linkedin.com/in/spencer-howard-82072710

X: https://x.com/spencerformiles

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About George Wright III:

George Wright is a Proven, Successful Entrepreneur- and he knows how to inspire entrepreneurs, companies, and individuals to achieve Massive Results. With more than 20 years of Executive Management experience and 25 years of Direct Marketing and Sales experience, George is responsible for starting and building several successful multimillion-dollar companies. He started at a very young age to network and build his experience and knowledge of what it takes to become a driven and well-known entrepreneur. George built a multi-million-dollar seminar business, promoting some of the biggest stars and brands in the world. He has accelerated the success and cash flow in each of his ventures through his network of resources and results driven strategies. George is now dedicated to teaching and sharing his Prosperity Principles and Strategies to every Driven and Passionate Entrepreneur he meets. His mission is to Empower Entrepreneurs Globally to create Massive Change and LIVE their Ultimate Destiny.

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