What if every bill you’re already paying could be getting you closer to a free flight?
Today I’m talking to Shakeemah “Keem” Smith — founder of Bills to Boarding Passes, solo travel educator, and the woman her family literally nicknamed The Passport Abuser — to talk about how she’s traveled to nearly 100 countries without paying out of pocket for a single flight in three years. And no, you don’t need a high-limit credit card or a six-figure salary to do this. Keem breaks down her Bills to Boarding Passes method, the airline partnerships most people have never heard of, why solo travel might be the most powerful thing you do for yourself this year, and the exact first steps to take this week, no matter your income, your debt situation, or your starting point. You’re gonna want to share this episode with a friend!
Key takeaways:
Your everyday bills are already boarding passes, you’re just not collecting
You don’t need to spend more money to earn airline miles. You need to make the money you’re already spending work harder. Gas, electricity, groceries, dining out, your pharmacy run — all of it is connected to airline loyalty programs that most people have never even heard of. American Airlines partners with Shell gas stations to give you three miles per gallon. NRG Energy partners with American, United, and Southwest to give you two miles per dollar on your gas and electric bill. American Airlines partners with CVS to give you three miles per dollar on everything from toothpaste to tampons. The miles are already there. You’re just not claiming them.
You don’t need a credit card to travel for free
One of the biggest misconceptions about travel hacking is that it requires a premium credit card with a hefty annual fee. Keem is clear: that’s just not true. Airlines have debit cards with no credit check and no annual fee that earn you miles on every swipe. United’s airline debit card gives you one mile per $2 spent, including on rent paid through a management portal. Southwest has one too. If you’re a single mom, if you’re paying off debt, if you’re building your credit, this is your on-ramp. You can start stacking miles today with the account you already have.
The “two out of three” rule is how you make every dollar do more
Keem has a personal rule: before she opens her wallet, she needs to be getting at least two out of three — credit card points, airline miles, and hotel points. If a retailer can only give her one, she goes somewhere else. American Airlines gives three miles per dollar at Best Buy but only one at Apple? She’s buying her MacBook at Best Buy. It sounds extreme, but this is what separates people who travel for $6 and people who don’t. You don’t need more money. You need to be more intentional about where you’re already spending it.
Solo travel isn’t about being fearless. It’s about learning to trust yourself
Keem’s pivot to solo travel didn’t come from confidence. It came from being left in Amsterdam on her birthday by a friend she’d trusted for years. She wrote out every single fear she had about traveling alone in a yellow notebook and confronted them one by one. The real revelation wasn’t about safety or logistics. It was that at 30 years old, she didn’t know how to enjoy her own company, and that was the thing that needed fixing. Solo travel was the solution, but the growth was the point. If you’ve been waiting for someone to come with you, this episode is your sign to stop waiting.
Being a Black woman traveling solo requires a different level of research, not a different budget
This is a conversation a lot of travel content skips entirely, and Keem addresses it directly and honestly. Traveling as a Black woman has never cost her more financially, but it has required her to be more intentional about research. Googling safety and cultural competence for every destination, staying more aware of her surroundings, noticing when she’s being treated differently. The cost is time and awareness, not dollars. And her perspective is ultimately one of possibility, not fear: nearly 100 countries, one bad experience, and a philosophy that life is too short and too precious to leave the world unseen.
One decision can change everything
Keem didn’t set out to build a business. She was 15 years into a job, fully vested in her pension, a homeowner. She just wanted to take a solo trip. That one choice led to 12,000 students, a multimillion-dollar business, and a life she built entirely on her own terms in Antigua and Barbuda. She’s not telling you to quit your job. She’s telling you that who you are on the other side of one brave decision is someone you can’t even imagine yet. The $6 flight to Japan, the first solo dinner, the first trip abroad — it all starts with deciding you’re worth the attempt.
Notable quotes
“I treat retailers like I treat men — you’re gonna have to work a little harder.”
“If I was born alone and I may die alone, why am I so afraid to live alone?”
“I don’t want to die with dreams because then it means it never happened. I want to actually have the memories.”
Episode at-a-glance
00:00 Intro
01:36 Your Bills Are Your Boarding Passes
04:07 Airline Miles vs. Credit Card Points: What’s the Difference?
07:05 How Airlines Make Money When You’re Not Flying
09:32 Earning Miles on Your Utility Bills (NRG Partnership)
11:03 How Keem Got to Her First 20 Countries for Under $100
13:55 How to Travel for Free Without a Credit Card
16:22 What Started Solo Travel: A Friendship Betrayal in Amsterdam
19:10 Learning to Enjoy Your Own Company at 30
21:29 Traveling as a Black Woman — Safety, Research & Real Talk
28:24 Actionable Steps for the Woman Who Thinks She Can’t Afford to Travel
31:44 Japan for $6 — Three Times (and Other Receipt-Worthy Receipts)
35:19 Treating Retailers Like You Treat Men: The 2-Out-of-3 Rule
38:44 Country That Surprised Me Most: Kuwait
39:31 The One Thing I Always Pack: A Carbon Monoxide Detector
41:27 Worst Travel Disaster: Saint Kitts Airport Scam
44:45 Best Flight Deal: $5 Flights as a Lifestyle
45:42 Most Underrated Solo Destination: Antigua and Barbuda
47:20 Final Message to the Woman Who Thinks Travel Isn’t for Her
Thanks to Rocket Money for sponsoring this episode!
Ready to turn your everyday bills into FREE flights? Sign up for our free Bills to Boarding Passes workshop with Keem & Tori: https://herfirst100k.com/ffpod.
Compare the cheapest flights from all major airlines at Skyscanner.com
Visit https://herfirst100k.com/ffpod to find our credit card recommendations and any other resources mentioned on our show!
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Meet Keem
Shakeemah “Keem” Smith is a solo traveler who has visited nearly 100 countries, a former child protective investigator from East Orange, New Jersey, and the founder of Bills to Boarding Passes — an education platform that has taught over 12,000 people how to turn their everyday bills into free flights and ace their first solo trip. Her book, “Ace Your First Solo Trip,” debuted at #2 on the Amazon Best Seller list in Travel. She holds a Master’s in Public Policy from Montclair State University and now lives in Antigua and Barbuda as an expat. Featured in CNN, Forbes, CBS National News, Essence, CNBC, USA Today, The Washington Post, Newsweek, and Business Insider. Her family gave her the name “The Passport Abuser” because she spent more time around the world than at home.
Transcript:
Tori Dunlap:
Today’s guest has been teaching me how to travel for free for over four years, and she has taken multiple international trips from Japan to South Africa to Paris for less than $10. We’re talking travel hacking today, but not just credit cards. Today is one of the most actionable travel episodes we’ve ever done. So if you see all of the posts, whether it’s from me or somebody else, talking about how to travel for free, this is the episode you need. Today’s guest has traveled to nearly 100 countries for less than a cup of coffee. Yes, really. Shakeemah Keem Smith is a solo traveler who has taught over 12,000 people how to turn their everyday bills into free flights and how to ace their first solo trip. Her family gave her the name The Passport Abuser because she spent more time around the world than at home.
And she is here to not only give us actionable resources to earn more miles, to be able to take cheaper, more luxurious trips, but also to show our community that this is possible for you. There’s so many misconceptions about travel hacking and credit card points, but you don’t even have to have a credit card to learn from Keem about how to travel for free. I met Keem in 2022. We were at a small business entrepreneur mastermind of people who are making more than seven figures in their businesses. And I was not only so impressed by her, but also was like, “Oh, you’re teaching me stuff that I don’t even know.” And that’s why I’ve invited her into our community to teach our first ever travel workshop. So after you listen to this episode, go to herfirst100k.com/ffpod to sign up for free. Let’s get into it.
But first, a word from our sponsors. So Keem, you’ve been to nearly 100 countries. You haven’t paid out of pocket for a flight in three years, and you started all of this while working a nine to five job. You were putting flights on layaway and you were packing your own lunch. So I want to start with the woman listening right now who just heard all of that and thought, “Okay, but what’s the catch?”
Shakeemah Smith:
Yeah, so most people think that you have to spend a fortune in order to travel, but actually your bills are your boarding passes, girl.
Tori Dunlap:
So when we talk about that concept, I mean, we’ve talked about it on our pages as well on social of using things like credit card points to travel, but you’re making this even more basic of saying that we can quite literally use the spend we already have to earn credit card points. Tell me a bit about that.
Shakeemah Smith:
Yeah. So in 2015, I was purchasing a home and here I was with this over 750 credit score, but I could not access any of the credit cards that I had currently had in order to travel. So I said, “You know what? How can I turn the things that I am already doing into flights?” So for me, it wasn’t an issue of I can’t get a credit card. It was an issue of I am purchasing a home, I cannot increase my debt to income ratio, I would still like to travel. I’m purchasing my first home. I don’t want the bank to look at my bank statements and see that I’m spending all of this money on travel. How can I travel, not spend any money and still have the best time of my life? And ultimately, Bills to Boarding Passes was born and it doesn’t require a credit card with a high annual fee, although I am a Chase girly. I love my Chase. Okay? But it’s all about recycling the money that you are already spending on your daily needs and flipping that into a boarding pass.
Tori Dunlap:
There’s this misconception, I think. I even talk about it with my own parents that, “Oh, it’s because you travel for work.” Or “I couldn’t do that because I don’t make six figures in income.” But you grew up in East Orange, New Jersey. You were the oldest of six kids. Your family didn’t travel. You didn’t leave the country until you were 25. So what was your starting point with travel financially?
Shakeemah Smith:
Yeah. So initially I started putting flights on layaway because I wasn’t familiar with the airline miles. And just for the viewers out there, for all the girls, airline miles are completely different from credit card points. Credit card points are what you earn when you spend your money and the credit card issuer gives you points that you can pretty much do whatever you want with, whether it’s buy a gift card, cash it out for cash, or use it for airline miles, right? But airline miles are miles that you specifically get from the airline directly. And most people don’t know that airlines actually make money even when you’re not traveling. They’re making money off of your behaviors so many different ways. So that’s how Bills to Boarding Passes was born, just me looking at all of the everyday items that I need, all of the bills that I already have to spend, and how can I earn airline miles.
And for the girls who do have credit cards, I love Chase. I have Chase, I love Chase, I love Amex, but if you could earn airline miles in addition to credit card points, now we’re getting somewhere. And even if you didn’t have one of those big fancy credit cards, you can still earn airline miles just by doing the things that you’re already doing. No overspending to get to that trip to Bali or anything like that. Just a straight line from your bills to the boarding pass.
Tori Dunlap:
Yeah. Well, and this is one of the reasons that I was so excited to invite you into our community to teach because you’re teaching me things that I don’t even know. And I think I’m pretty good at this. So if you’re really lost, imagine if she could come teach you and also she’s teaching me something. So we’re doing a free workshop. You can go to herfirst100k.com/ffpod and we’re doing all of this teaching about how do we take our bills to boarding passes. So if you want to sign up, that’s herfirst100k.com/ffpod. Okay. You said something that I thought was really, really interesting that I didn’t think about. You just said that the airlines are earning money even when we’re not traveling. Tell me more about what you mean by that.
Shakeemah Smith:
Honestly, girl, I was so intrigued when I started going down this rabbit hole many years ago. So most of us think that in order to earn airline miles, that we either have to be flying with the airline and after we fly, they just add the miles to our frequent flyer account.
Tori Dunlap:
Right.
Shakeemah Smith:
But airlines are making money even when you don’t have your but in that seat. Okay, girl. So for instance, one of the things that we do every single day is we probably get gas, fuel for our car to get to work, to get the kids to school, or you’re probably taking a rideshare app if you live in like a metropolitan city like New York. But most people don’t know that American Airlines actually has a partnership with Shell gas station. So if the listeners decide to just get up on Google and put in American Airlines, Shell, Fuel Rewards, then you’ll see that American Airlines gives you three miles per gallon of gas that you get for your car without ever having to have a credit card.
And the wonderful thing is if you do have a credit card like me, right, you got that Chase, you got that Amex, then American Airlines is giving you that three miles per gallon plus Chase or Amex is giving you dollar for dollar because that’s the card that you presented when you got to the Shell gas station. So these airlines, they have their hands in your wallet even when you’re not at the airport or on an airplane. They’re making money off of all of your other behaviors.
Tori Dunlap:
That tip in and of itself, like I didn’t know that. Right. I didn’t even know that. And this is the kind of thing where as life is getting more expensive, right? I’m recording this while gas in Seattle is at best 5.50 a gallon and I need gas, I have to drive. We may as well be making that really expensive purchase work as hard as it can for us. So not just with credit cards, which I talk about a lot, but I love this hack of making sure that you have your American Airlines mileage plan hooked up to the Shell stations, right, and that they can kind of talk to each other so that you’re getting, you said three points or three miles for every single gallon spent. That’s massive. That’s huge.
Shakeemah Smith:
Yeah. And that’s just one of many things, right? Most people think, “Okay, well, do I have to overspend or?” Most people think, “Well, I don’t spend enough to earn credit card points or airline miles to travel.”
Tori Dunlap:
Yeah.
Shakeemah Smith:
But if you guys think about everything that you’re doing on a daily basis, I know you’re talking about, we were just talking about fuel and you were telling me how expensive gas is in Seattle, right? But a lot of people are also complaining about their energy bills lately. People are saying like, “Hey, my electricity bill, my gas bill went up.” But there is this energy company, it’s called NRG and NRG has a partnership with American Airlines, United Airlines, and Southwest Airlines, and you earn two miles per dollar that you spend on the supply portion of your gas and your electric bill. Now, this is just another bills to boarding passes, right, because we need gas anyway.
Tori Dunlap:
Right.
Shakeemah Smith:
We’re not going to walk, right? We need electricity in our house. Even if you have solar, then you still need gas for cooking. And again, American, United, and Southwest all partner with NRG so the listeners can Google this. So if you think about, I have been paying an electricity bill since I was like 19 when I first moved out of my parents’ home, right? So think about how many vacations we’ve missed out on just by not having that one piece of information.
Tori Dunlap:
Well, and then it’s shameless plugged for the workshop, but this is what we’re covering.
Shakeemah Smith:
Yeah.
Tori Dunlap:
This is this kind of stuff that, like you have so many of these hacks that, again, I didn’t even know. So herfirst100k.com/ffpod. Okay. You got to your first 20 countries for under $100 a flight. You were working full time.
Shakeemah Smith:
Yep.
Tori Dunlap:
That is crazy.
Shakeemah Smith:
Yep.
Tori Dunlap:
So what do under $100 international flights actually look like? Where are you finding those? How are you able to do this?
Shakeemah Smith:
Yeah. So back in the days, around like 2017, skyscanner.com had this feature where when you go on Skyscanner, you can select everywhere.
Tori Dunlap:
Everywhere. The everywhere feature. Yeah.
Shakeemah Smith:
Yeah. And then back then it had another feature that said cheapest month. So it would literally tell you the cheapest month to get to anywhere on our beautiful, wonderful globe. And I would only look up countries that were under $100. And that was how I got to my first 20 countries for under $100 because I selected everywhere and then cheapest month. And in 2022, they took it away. My heart was broken. I had to find another way to travel. And I thought, why don’t I just start earning airline miles? No credit card points because I’m getting my master’s degree and I have to pay for it, right? And so I’m like, all right, I don’t want to have too much stuff going on like on my credit. Let me just figure out how I can earn airline miles with the airlines directly.
And I just love my cards. I love my cards, but I’ve been seeing so much in the news lately about the current administration wanting to stop Americans from having any type of credit cards, which means that we’ll be traveling, but we’ll be needing those airline miles from the airline directly if we don’t have credit card points anymore. So having airline miles has always been like a really good safety net for me because I actually never really have to use the Chase and the Amex points because I always can go directly to my airline miles first. So I’m a girl who does both. So if you are a listener and you have the credit cards, great. Now let’s get you some airline miles too.
Tori Dunlap:
Yeah. When you say that, because again, I talk about the importance of credit cards. I am all in that world. I love it. I’m literally taking the trip to Hawaii next month with my partner and the hotel, which is a $1,000 a night hotel is entirely free with credit card points. And that’s the kind of stuff we’re talking about. But you can also do this without credit cards. And I think that’s a big distinction from a lot of the travel centered guests we’ve had on the show previously, or even the content I create. So what do you say to those people who assume that it’s really, really complicated?
Shakeemah Smith:
I’d say definitely get in the proximity of people who know otherwise. That’s the first thing. Second thing, open your mind, right? Because if you’re in the mindset where you’re like, “I don’t believe that I can really do this,” then we’re not going to really get too far from Kansas. Right. So for the person who believes I have to have a credit card in order to earn airline miles, totally false. So here’s what you can do. You can open up an airline debit card. Most people don’t know this, but airlines have debit cards and you can earn two miles per dollar every time you swipe your debit card. So if like my little sister, my little sister has always been my case study because she’s a single mom with three kids, right? So I’m like, okay, she’s the perfect person that I can work with because I’m able to expand, right, because her resources are a little bit more tighter than mine.
I’m single with zero children, right? I only have to fend for myself. So first thing is, I would say get an airline debit card. Airlines actually have debit cards. So if the listeners Google United Airlines debit card, you’ll see that if you pay your rent online through a management portal, then that United Airlines debit card is going to give you one mile per $2 that you spend. There’s no credit check required. Its FDIC insured and again, there’s no annual fee.
So if you think about the money that you’re just spending on food with your debit card to go to lunch during your lunch hour, and then you put gas in your car, and then you’re paying your rent, you’re paying the kids’ daycare, you’re buying groceries. If you were to switch out your regular, I don’t know, TD Bank debit card for an airline debit card, United has one, Southwest has one, then now you’re earning miles just as the person who actually swipes a Chase or an Amex. If you want to get started with earning airline miles so you can travel the world for free, it’s definitely more within reach than what you think.
Tori Dunlap:
When you and I met, this was 2022, we were at a entrepreneur mastermind and first of all, I was so impressed by you and I was literally like, “First of all, teach me everything that you know about all of this,” because I think that that was one of the tipping points for me, getting more into learning how to travel for free, learning how to travel for cheap. You were that impetus point. And I think one of the other powerful things that I learned in that couple days we spent together is you love traveling solo as much as I do. So when was that moment that you decided to pursue solo travel, even though at a societal level, right, we’re told that solo travel’s either scary or intimidating, there’s a million reasons not to do it, right? What was the moment for you where you were like, “No, I’m going to do this?”
Shakeemah Smith:
Girl, it’s tea. It’s tea, girl, but I’ll be honest with you because you and I were like that. So to be honest, T, I went on a girls trip and it was a really bad girls trip. I had a friend and we had been friends for years. This was not someone that I had just known for a short amount of time. And I expressed to her, I said, “Hey, I don’t want to get in your business, but I think this guy might be using you financially and I just want you to know that. If you love this guy and he loves you, that’s great, but when he sends you emails while we’re on vacation saying, ‘Buy me rims if you want to get back together, I want to ticket to Egypt.’ your wallet in your heart, like you don’t have to buy love.” “And if he dumped you and told you to leave his house with two dogs in the middle of the night, why do you have to buy him a ticket to Egypt and rims for his BMW in order to reconcile? I just want to tell you that.”
And she left me on my birthday and didn’t even tell me. I just woke up and she was gone and I called her the next morning and I said, “Where are you?” And she said, “Oh, I left. Derek loves me and you’re going to see.” And that was like the end of it. And for like the longest time, like my heart was so broken, but I started reaching out to other friends like, “Hey, I want to go somewhere, but I just want somebody to travel with me.” And everybody was like, “Okay, I don’t got the money, so if I’m going to go with you, can you help me with my ticket, but I can come with you?” And I’m like, “No.” And then other people that I was asking didn’t have an issue with money, but they were like, “Oh, my man said that I can’t go.” Or “I don’t have a babysitter.”
So one day I just wrote out an ugly yellow five subject notebook, I wrote out every single fear that I had of going somewhere by myself and I thought to myself, “Girl, you are from East Orange, New Jersey. You are from, by all intents and purposes, like you’re from the ghetto, okay? So what could be worse than where you already are? Can you trust yourself?” And I’m the oldest of six kids, T. So you know, girl, I’m used to it being a gang of us everywhere I go.
So the tipping point for me was not just me being left on my birthday in Amsterdam without even a goodbye text. The tipping point was realizing that at 30 years old, I don’t know how to enjoy my own company. And that was the blow to my chest, girl, that I was like, “Okay, you got to get out of this because you have to look in the mirror and say, look, I’m one of six kids. I’ve never been alone.” So subconsciously, I think that I need other people with me to have a good time or I think that if I go alone, I’ll be bored or.
And so I had to really examine my fears and like really look in the mirror as a 30-year-old and be like, “Keem, look at yourself. You are so scared of even enjoying your own company. You’ve never even been to dinner alone.” And so I think that what happened in Amsterdam the night before my birthday was a catalyst, but me examining my truth and the symptoms of, I don’t know how to be alone or I feel like I can’t be alone, that was the bigger elephant in the room that needed to be addressed. And I was like, “You know what? I’m doing this.” And my mom said like, “Oh, courage is just fear that said it’s prayer. Have some courage.” It’s the same thing. It’s just the bow is different and girl, I just went for it.
Tori Dunlap:
There is a woman out there listening who feels so, so seen by what you just said. Absolutely. And I think it is that self-trust piece. There are very real reasons that solo travel can be risky and also as someone who has also traveled alone, I can count on two fingers the times where I’ve had even like a slight incident. It’s truly, I think it’s all in our heads and it’s more about the fact that we might not have been alone for our entire life. Exactly what you said, we might not be comfortable with our own thoughts, with our own company. So we’ve talked about this before with Joe Franco on this show, but what does safety actually look like when you’re a black woman traveling solo? Do you find it more expensive to be safe? Are you spending more on accommodations or is that a financial conversation people aren’t having?
Shakeemah Smith:
So for me, being a black woman has never really impacted my travels financially, but it does require a different level of research that I would say. So like-
Tori Dunlap:
Okay.
Shakeemah Smith:
I would find myself Googling, if I go to this country, are they racist towards black women? I would find-
Tori Dunlap:
Right. Right.
Shakeemah Smith:
Myself Googling things like that. But honestly, as a solo traveler, I always kind of look up a little bit of information about the country just so I can understand cultural competence or societal norms or just small things. Like when I took my first solo trip, I was like looking at all of these things on the internet about how to be solo in Paris. And it said, “Put your menu down, don’t signal over to the waiter, but put your menu down. And that’s the signal that you’re ready to order because you stop looking at the menu.” So although I can’t say that I feel that my trips are more expensive because I’m black versus like my girlfriends who are not black, I will say that I do a little bit of level of research.
Also, I am more keen, like my senses are more aware. So when I’m traveling, I will look around and be like, “Hey, did they give them their room before me? But I’ve been here since 11:00 AM sitting in this lobby.” So there are things that I look out for, but I’ve never had to pay a different price. Or it’s never really been a difference in finances with my girlfriends who are not black.
Tori Dunlap:
Yeah. I think about even as a woman, not a woman of color, making sure that I am in situations or staying in places, especially when I’m traveling solo that feel really safe or that somebody’s looking out for me. And one of the easiest things I do is like before I leave the hotel, I will literally let them know like, “Hi, I expect to be back by this time. If I’m not back by this time, here’s my number, call me.” And I think that that’s just a really nice way of checking in. I would normally do it with my family, but I might have a time difference. So that’s a great way of making sure that somebody’s looking out for you while you’re traveling. But again, I have never had an incident and I think that your perspective is so important because I imagine you sometimes do get treated differently as a black woman and I want to prove to women though that there’s still great reasons to travel and still great reasons to travel solo.
And I love that you made that list because the thing that occurred to me in my mid-20s was very similar to you. People didn’t have the same flexible schedule I did, or people had children, or people just had commitments and I found myself sitting on my hands and I was like, “Okay, guess I’ll wait.” And at that time I was single as well. So I was like, “Okay, I don’t really have anybody to travel with.” And it just occurred to me, I was like, “Are we going to wait forever? Am I going to spend my entire life waiting for somebody to come along that I can travel with or for the absolute perfect opportunity?” And I’m like, “No, if I want to go, I’m going to go and I’ll figure it out.”
Shakeemah Smith:
Yeah. I decided a long time ago that when I was born, no one was there. I had no control over when I was born and who was there. When I die, I will have no control over what day, when that happens, and who’s there. So if I was born alone and I may possibly die alone, why am I so afraid to live alone?
Tori Dunlap:
Yeah. Yeah.
Shakeemah Smith:
So I just decided when I die, I don’t want to die with dreams because then it means like it never happened. I want to actually have the memories. When I’m in heaven, I want to look down and be like, “Yeah, I did that too. Yeah. Haha.”
Tori Dunlap:
Yeah.
Shakeemah Smith:
I don’t want to feel like this one gift. It’s so precious. Life is so precious and it’s so fragile. I want to leave a legacy. And the one thing that I love about you, and I said this, I was talking to my mom about you actually, and my mom was looking you up. And my mom said, “What I love about the work that she’s doing is that the women that she’s helping financially, as long as they continue to say her name and then they teach their children Tori’s literacy, she can never die because her legacy lives on.” Right. And so my mom was like, “She’s creating a legacy that is going to continue to live on because what she is doing, people will pass it down and pass it down.” And I just kind of thought about myself and I’m like, “I want to be the person in my bloodline that decided to take every chance. I don’t want to leave anything on the table.” So I’d say, “Live your life, ladies.”
Tori Dunlap:
Keem, there’s a joke on this show of how quickly I cry in an episode and your mama got me. That’s really, really kind. And that’s how I feel about you. That’s why I wanted to partner with you to bring your work to our community. Why we’re doing this workshop, why I’m having you on this show is because again, you’ve taught me things that I didn’t even know. And two, we make this out to be so complicated and it’s no different than any other concept we’ve talked about on this show. Women go, “Oh, I can’t pay off my debt because it’s too complicated. I can’t invest in the stock market because it’s too complicated. I can’t actually get my budget together because it’s too complicated.” And to that, I always say, “Okay, who taught you that? Who taught you it’s too complicated?” A system that wants to keep you broke, a system that wants to keep you miserable, a system that is committed to making sure that you live a very small life.
I want you to be growing your wealth. I want you to be paying off your debt. I want you to be traveling in a very luxurious, frequent way without having to spend tens of thousands of dollars to do it. And that’s what you’ve shown me. That’s what you show your hundreds of thousands of people. So when I think about a woman listening, there’s a woman listening in her car right now. She makes 55K a year. She has student loans. Maybe she’s never even left the country. What are the first three things that that woman does this week?
Shakeemah Smith:
So the first thing that I’d say do this week is you are eating probably like every day, right? So if you Google-
Tori Dunlap:
Hopefully. Hopefully you’re eating every day.
Shakeemah Smith:
Right, right, right. You’re eating every day. And the reason why I take it down to the basics is because people still can’t wrap their heads around, you mean to tell me something simple as feeding myself, something that I have to do to survive the airlines owe me airline miles every time I go to eat?
Tori Dunlap:
Yeah.
Shakeemah Smith:
Yes, yes, they do. It’s just that it’s not front page news, but they do. So the first thing that I would say do this week, you’re eating every day. That’s something that you cannot miss out on. If you Google airline dining program, okay, every time you go out to eat, I want you to pick from a restaurant on the airline dining portal with your favorite airline. So if your favorite airline is Delta, I want you to Google Delta Air Lines dining program. And the beautiful thing about this is you do not need any type of airline card in order to get miles for taking your kids out to eat because they got a good report card or taking the kids out to eat after church.
Or even if you and your girls want to go out because it’s Sunday fun day and you all want to have a little boozy brunch, that should be airline miles, regardless of whether you are paying with a regular debit card from a Wells Fargo or even if you were paying with a credit card, regardless of the fact, you’re supposed to be getting airline miles. So first thing that I want you to do is just think about the things that you’re doing every day. You brush your teeth, you have to use toothpaste, you need tampons, you need shampoo. These are all the things that women actually need, but American Airlines has a partnership with CVS where they will give you three miles per dollar that you spend at CVS. So for all of the things that you need for basic hygiene, from the minute that you wake up, that is supposed to be airline miles.
When you turn on your light in your house, when you come in from work at night, that’s airline miles. There’s this company called Reliant Energy, and they are specifically in the state of Texas. So for all of the Texas girlies that are tuning in to our show today, Reliant has a partnership with Southwest Airlines where they will give you 27,000 rapid rewards points when you get an energy plan through Reliant. So every single thing that you’re doing as you go throughout your day is probably airline miles. Make sure that if you are listening and you don’t have a credit card or you can’t get a credit card, make sure you get an airline debit card. We spend so much time scrolling. Right. Airlines actually have surveys that they’re going to give you airline miles. So it’s like, I can’t say enough about what to do, but what I will say is there is a way.
And if you are a person like me who you have a Citi, a Amex, and a Chase, well, girl, pull up a chair because now I’m about to show you how to double dip and triple dip all of that. Okay? This three-day challenge is going to be so impactful because there are so many airline miles that you’re missing out on, even if you had credit card points. And I can’t wait to show that with everyone.
Tori Dunlap:
Yeah. I mean, this is why I wanted you on. The specificity of anybody in Texas, here’s another way you can get airline miles, anybody shopping at CVS. And this is why I love your advice, is it’s not just super broad or it’s just like, yeah, just, I don’t know, figure out a way to travel for free. It’s very specific. It’s like, here are the strategies. Here’s what we’re going to do.
So a lot of women out there feel guilty spending money on travel when they have debt or some other financial goal. What is the conversation you have with a woman who says, “I can’t justify a vacation. I have $30,000 of credit card debt or $30,000 student loans.”
Shakeemah Smith:
Yeah. So I’ve traveled to Japan for $6. Aruba for $15.
Tori Dunlap:
Hold on. Hold on. Keem, I just, I have to stop you. You traveled to Japan, presumably from Jersey? Yes?
Shakeemah Smith:
Yes.
Tori Dunlap:
For $6.
Shakeemah Smith:
Three times.
Tori Dunlap:
Three.
Shakeemah Smith:
And I have the receipts to prove it.
Tori Dunlap:
And I’ve seen the receipts.
Shakeemah Smith:
Clock it.
Tori Dunlap:
I’ve seen the receipts. $6. Everybody has $6. I spent $6 on a coffee yesterday. $6.
Shakeemah Smith:
Yep. Yep.
Tori Dunlap:
Okay. And you were going to say other cities too. I just had to stop you. Japan three times for $6. Okay. Where else?
Shakeemah Smith:
Japan three times for $6. I went to Athens, Greece for $6. I purchased a flight to Johannesburg for $6. And guys, these were all… I cannot wait to the three-day challenge because I’m a receipt queen. If I say anything, I have receipts. Okay? And the beautiful thing is when you see my receipts, they’re actually not from Chase Travel portal or Amex Travel portal. They’re actually all directly from the airlines themselves because all of your bills and your everyday purchases and your mandatory living expenses are airline miles completely outside of credit card points. But if you have the credit card points, we going stack it, stack it, stack it, girl. You know what that song says, “From the windows to the walls,” you know what I mean? Where we going to stack them credit card points with the airline miles and with hotel points, right?
Because in the three-day challenge, I’m also going to be showing people how they can get free hotels as well. Right. I went to Dubai for the weekend, three days, me and my sister. Our hotel was $12, so. And I have the receipts directly from Marriott Bonvoy. So I want to show people like, “Hey, when it’s time for you to take those kids to Orlando, or if you’re a single person like me with no kids and it’s time for you to go visit your family in North Carolina for a family reunion, all of this should be free.” When you want to go to Johannesburg or Bali or Paris, that should be a $5 vacation every single time. And it’s not going to put you in debt. You just have to know how to flip those bills and the things that you’re already spending money on. You just have to know how to convert it into airline miles and hotel points.
Tori Dunlap:
Yeah. And I say this with all due respect, Keem. This woman is a black woman from Jersey, right? You don’t have a degree that somebody else listening doesn’t have. I don’t have a degree somebody listening doesn’t have in this. It’s just because you have knowledge that somebody else doesn’t, and that’s why you’re teaching this. So I think I can already hear somebody going, “$6, it’s crazy. She had to yeah, take out a bunch of credit cards. Or she had to spend hours and hours and hours hacking the system.” And no, she doesn’t know anything that you don’t, especially after this three-day challenge because she’s teaching you everything. So the DM I get all the time is just like, “Well, you’re a financial educator.” And I’m like, “I learn the same way as you’re going to learn. I learn from Keem. I learn from other people to teach me step by step how to do this.” There’s not some, I don’t know, yeah, secret degree you can get or secret skill the or I don’t know, DNA trait that you and I have that somebody listening doesn’t. The $6 flights can be yours too.
Shakeemah Smith:
Absolutely. Absolutely. I can’t wait to blow everybody away because ever since COVID, girl, everything is just so expensive. And I’m like, you know what?
Tori Dunlap:
It’s so expensive.
Shakeemah Smith:
I don’t mean to be vulgar on the show, but I consider-
Tori Dunlap:
We don’t care.
Shakeemah Smith:
Opening my wallet the same way I would consider opening my legs, right? And so, girl I’m just-
Tori Dunlap:
No, I mean, I get it.
Shakeemah Smith:
Girl.
Tori Dunlap:
It’s expensive out here. It’s expensive out here.
Shakeemah Smith:
It’s expensive. So just the way you would think twice before you open your legs like, “Oh, is this what I want?” I literally think twice before opening my wallet. I have my three prongs, credit card points, airline miles, hotel points. I need at least two out of three to open up the wallet. If I’m not getting at least two out of three, you ain’t getting my money. These corporations already have millions and billions of dollars. Okay? If I know that I’m supposed to get airline miles when I go to Sephora or when I go to Lululemon, I’m supposed to get three miles per dollar from American Airlines, plus I’m getting my Chase points. So now that I live this lifestyle, it’s not even good enough for me to just have Chase points anymore. You need to get me two out of three or you don’t get me.
I used to consider myself energetically bougie where I’m like, “Uh-uh, no. If a man’s energy doesn’t match me, no, I’m energetically bougie,” whatever. But I’m also financially savvy and empowered. If this retailer doesn’t find a way to get me some airline miles, I’ll go to the next person. So let’s say I’m shopping at Walmart. If American Airlines, United Airlines, or Delta Air Lines says, “We don’t have any reward for Walmart,” we don’t go to Walmart. Instead, we go to Walgreens or CVS, right? Or if I’m looking on American Airlines website and I see, okay, they’re going to give me one mile per dollar if I shop at Apple, but at Best Buy is three miles per dollar. I think I’m going to go ahead and go to Best Buy and get that MacBook because that’s how I’m getting… So literally, I just made it a point to where you want my money, you’re going to have to work for it.
Tori Dunlap:
I think that’s so, so wise. Again, all of this spending that feels so expensive right now, it almost just lessens the blow a little bit. And I think about this too, when I have to spend money anywhere is it’s like, okay, at least I earn credit card points and that’s going to my free Hawaiian vacation. That’s going to lie down flat seats to Paris for 30 bucks. And that’s something that, again, doesn’t completely dull the pain of an expensive situation, but it at least makes it better. You’re like, “Okay, I’m already spending this money. I may as well get a little bit of money for it.” And also, these companies need to work for my dollar because you’re exactly right. These are multi-billion, if not trillion-dollar companies, the least thing that they can do is work a little bit.
Shakeemah Smith:
Absolutely. Absolutely. So I treat retailers like I treat men like, “You’re going to have to work a little harder if you want…” I have to be like that with my money. And because I’ve been so stern, I’ve been so disciplined with myself like, “Oh, okay, if I’m going to order Uber Eats, I better be getting some Marriott Bonvoy points.” I’ve been so stern with how I live my life, it has to give me two out of the three.
Tori Dunlap:
I think that’s really smart. Okay. Keem, we’re going to do a rapid fire. Are you ready?
Shakeemah Smith:
Yes.
Tori Dunlap:
Okay. Country that surprised you the most?
Shakeemah Smith:
Kuwait.
Tori Dunlap:
Tell me, I’m screwing up the rapid fire, but tell me why.
Shakeemah Smith:
So many people told me, “Don’t go to Kuwait, Desert Storm, don’t go there. It’s so unsafe.” I met these two girls in Italy and they told me that they were from Kuwait and I said, “Oh, is it safe to go to Kuwait because it’s so close to Iraq?” And they were like, “No, Desert Storm was 1995, honey. Read a book, come out to Kuwait.” And three weeks later, I was in Kuwait and I had the most beautiful time in Kuwait ever and I felt so safe. I felt so safe. And I was like, “Wow, this is just definitely one of those underrated countries.”
Tori Dunlap:
Yeah. The one thing you always pack.
Shakeemah Smith:
A carbon monoxide detector in my luggage because there have been so many times… Girl, girl, there have been so many times where I go onto Google, click travel and just look at the news articles that pop up. And it seems like every few months, it’s like three Belize tourists died in hotel due to carbon monoxide poisoning. Two couples-
Tori Dunlap:
Wow.
Shakeemah Smith:
Died the same weekend at a Sandals resort in the Bahamas. Sandals is expensive. I treated my mom and dad to Sandals before my dad died. It was like their 35th wedding anniversary. And it cost me like, I would say, I think it was like $6,000. And this was back in 2019 or 2020-
Tori Dunlap:
Yeah, so it’s more expensive now.
Shakeemah Smith:
Very expensive back then. And I really wanted to do this with them because my parents, they had never been anywhere. They had six… They just never been anywhere. So I was like, “I’m doing this for them.” And even with as expensive as Sandals are, if the listeners just Google carbon monoxide detector deaths at Sandals in the Bahamas, like just put it up on Google and they’ll see it. And if you just go onto Google and put tourists died on vacation, carbon monoxide, you’ll see a bunch of different articles that pop up, Costa Rica, Belize, Mexico, Bahamas, whatever. And so I said, “You know what? As a female solo traveler, I have to realize that safety isn’t always a physical, imminent threat that I can see. It might be this odorless thing going around that I don’t even know about.” And so-
Tori Dunlap:
Wow.
Shakeemah Smith:
I always pack a carbon monoxide detector and a door jammer just in case somebody gets the wrong key, whatever. But rapid fire, I would say carbon monoxide detector.
Tori Dunlap:
That’s insane. And you’ve given me another thing to be anxious about. Thank you. Wow. Okay. I’m making a Google after this. Okay. Worst travel disaster.
Shakeemah Smith:
Worst travel disaster ever was in Saint Kitts. And out of all 93 countries-
Tori Dunlap:
Okay.
Shakeemah Smith:
That I’ve been to solo, I’ve only had one bad experience out of 93 countries. I guess my grandmother’s prayers and the blood of Jesus is working because I just never had any problems 100 countries in. It was country 63 for me.
Tori Dunlap:
Okay.
Shakeemah Smith:
And I got to Saint Kitts. At the airport, the guy said, “Give me 10 US dollars for a Ziploc bag or we’re throwing everything away.” And this is country 63 for me. And I said, “Well, everything is under 3.4 ounces. And it says it all at the bottom of the jar. So I’m not really sure why I have to give you…”
Tori Dunlap:
Why.
Shakeemah Smith:
It seems scammish. Why do I have to give you $10 for a Ziploc bag when all of my stuff is under 3.4 ounces? And he said, “Listen, if you don’t give me the $10 for a Ziploc bag, I’m throwing everything in here away.” I said, “Well, you still haven’t explained to me why if it’s under the 3.4 ounces, do I actually need the Ziploc bag?” And he just took all of my makeup and threw it away right in front of me. PCA serum is like $150 a bottle and I had three different bottles because one is for the under eye cream, one is for the hyaluronic acid, whatever. He just threw everything away right there on the spot and he was like, “Now move.”
Tori Dunlap:
Cool.
Shakeemah Smith:
His words to me were literally like, “And go.” And I was like, “I am never ever coming back to Saint Kitts.” And I posted about my experience on Instagram and I literally had 128 women reach out to me. I saved all of their comments to a Google Drive doc and I sent it to the tourism authority in Saint Kitts and I said, “Hey, I went forward with my story online and here is 128 other people who responded to me and said that they had the exact same experience. And so it wasn’t just me. This is something that you guys just do.” I saved it as a highlight on my Instagram so that way everybody could see how they do.
And I got an email from them apologizing, but I would never, ever, ever step foot back in Saint Kitts. And I know that some people say you cannot blame the whole country for the people at the airport, right? And that’s true, but let’s also consider people who work at the airport live there, right? It’s not like these people are flying in from another country to work. If this is the interaction that you’re getting at the airport, don’t these same people live here?
Tori Dunlap:
It just leaves a bad taste in your mouth. That’s such a bummer. And it is such a reflection of like, I think about all the time if somebody’s visiting Seattle, how do I show them the best time possible? Because I want them to go home and go, “Everybody in Seattle’s so nice,” just because they met one nice person. And it’s the same thing on the flip side with you, you meet one not so nice person and you’re like, “Well, this ruined my trip.” So I have such empathy for that. And I also love that you were a petty bitch because I would’ve done the same thing. Okay. Best flight deal you’ve ever found?
Shakeemah Smith:
Well, I get credit card, like do you mean like…
Tori Dunlap:
I mean, maybe it’s the $6 to Japan.
Shakeemah Smith:
Yeah, I’m like-
Tori Dunlap:
But give me your best stats.
Shakeemah Smith:
I get this all the time. Yeah. So I’m able to fly out all the time for no more than $5, so that’s like an everyday occurrence for me. So if a friend says, “Hey, do you want to have lunch in Paris this week?” And I’m like, “Yeah, I’ll get a $5 flight there. I can be there this weekend. No problem.” So this is a lifestyle for me. And that’s the thing, right? I want to show women around the world like, “Hey, listen, girl, you don’t have to dip in your back pocket or have even a travel budget where you’re putting $100 in from every paycheck to travel and go to all of your bucket list destinations. This is just a matter of making a few lifestyle changes.”
Tori Dunlap:
Yeah, that’s huge. Most underrated destination for a solo trip, a first solo trip.
Shakeemah Smith:
Antigua and Barbuda.
Tori Dunlap:
I mean, you live there now, right?
Shakeemah Smith:
I live there now. Yeah. I’m in Jersey now because I’m with my mom more now that my dad has passed, but in 2020, I moved to Antigua and Barbuda. I didn’t know a soul there, didn’t have any friends there. I went there and I got off the plane and something in my body just said, “Welcome home.” And I had never felt like that ever, like ever. And so I was like, “You know what? I love this place.” I stayed for a week and I just, something inside of me felt like I was home. I don’t know what it was. I can’t explain it. It was just a feeling. And from there, I went home, I paid off all my credit cards and I quit my job and I moved back to Antigua and I signed my lease and I have been there up until September of 2025.
My mom reached out to me and she said, “Hey, I think your dad is going to go. And he stopped talking and he stopped eating, so I think it’s going to happen. I want you to come back home.” And so I’ve been here in New Jersey since September of 2025. But yeah, I’ve been living in Antigua and Barbuda full time and absolutely love it. It’s so safe. You’ll be so fine. I absolutely love it. I definitely recommend for a first solo trip.
Tori Dunlap:
That’s fantastic. That’s a place I haven’t been, so I’m adding it to my list.
Shakeemah Smith:
Okay. So now you got to come. You got to come. I’m going to pick you up from the airport.
Tori Dunlap:
Incredible. You got to show me around.
Shakeemah Smith:
And I’m going to show you around.
Tori Dunlap:
So my last question for you. There is a woman listening right now who wants to travel so deeply. Maybe she’s traveled a bit, maybe she’s never traveled at all, but she’s convinced that it’s not for her because I’m in a financial situation where I can’t travel. She thinks she needs to pay off her debt first. She thinks she needs to save first. She thinks she needs to get her life together first. What do you want to say to her?
Shakeemah Smith:
Well, the beautiful thing is there’s not much guilt associated if the flight is $5, right? And so you don’t have to worry about travel is so expensive for me because the things that you’re already doing equal travel. And that’s what we’re going to talk about in the three-day challenge.
Tori Dunlap:
And I will add to that of truly all the cliches are true. Why not you? Why not you? There are so many opportunities for you. Even if it’s just traveling inside the US or inside North America, there are so many incredible experiences that you can have that are not going to break the bank, that are not going to put you in debt, that are not going to add more stress to your life. In fact, this thing, this travel experience, this trip might be literally the thing that actually changes your life, that eases your stress, that brings you back to yourself and also shows you that you can do this thing that you think is complicated. You can learn how to travel for under $10. You can learn how to be comfortable in your own skin if you want to travel alone. So I’m just so excited to host this with you.
We’ve never done anything like this. And it’s because, again, since I met you in 2022, I was like, “Oh, I want to learn from her.” So I imagine our millions of people and our audience want to learn from you too. So I will shamelessly plug. If you go to herfirst100k.com/ffpod, we have all of the resources there. I expect to see every single one of you listening are watching there. But Keem, anything else you want to plug?
Shakeemah Smith:
Yeah. So first thing, I want people to go back and not only listen to this podcast over and over again, but make sure you share this episode with everybody because I am a person who I don’t do fluff. Give me actionable steps to see if this can work for me. I’m that girl, right? I’m like, “Cut the fat from the meat and just give it right to me. Give it to me straight.” And one of the things that I will say is, if you go back and listen to this podcast, I have dropped like name-drop things that you can actually head over to Google and say, “Oh, you know what? This is legit.” So if you’ve been listening to this podcast and you go back and replay it and you see like, “Oh wow, there is a way that my bills are actually attached to my favorite airline,” then you definitely want to purchase a ticket to the VIP challenge for the three-day challenge.
That’s the first thing. Second thing, because I want to touch on something that you just mentioned, who you are on the other side of one piece of action can totally transform your life. I never thought that I would be a multimillionaire. I never thought that I would be teaching people how to flip their bills into boarding passes. I never thought that I would have 12,000 women that I’ve helped ace their first solo trip and learn how to travel for free. And all of that started with one choice, one choice. I’m going to take my first solo trip. So even though I couldn’t see that I would have a bunch of clients someday and I would learn how to flip my bills into boarding, all of that was way down the line, right? But it all started with one trip. And so when I consider how far I’ve come, this wasn’t supposed to be a business.
I was working for my job for 15 years, right? So why would I leave my job? I’m into my pension. Life is good. I own my house. This was just supposed to be something fun, that I wanted to take a solo trip. Then from there, so many women reached out to me and boom, here comes all of these wonderful things, but it started with just one decision. So definitely consider who you are on the other side of just making this one decision to take one hour out of your day for three days to come to this Bills to Boarding Passes challenge.
Tori Dunlap:
I couldn’t have said it better. I’m so excited for you, so excited for us to pour into everybody that’s going to show up. And thank you for being here. Thank you for your work.
Shakeemah Smith:
Thank you.
Tori Dunlap:
Thank you for listening to Financial Feminists, produced by Her First $100K. If you love the show and want to keep supporting feminist media, please subscribe or follow us on your preferred podcasting platform or on YouTube. Your support helps us continue to bring this content to you for free. If you’re looking for resources, tools, and education, including all of the resources mentioned in this episode, head to http://herfirst100k.com/ffpod.
Financial Feminist is hosted by me, Tori Dunlap. Produced by Kristen Fields and Tamisha Grant. Research by Sarah Sciortino. Audio and video engineering by Alyssa Midcalf. Marketing and Operations by Karina Patel and Amanda Leffew. Special thanks to our team at Her First 100K, Kailyn Sprinkle, Masha Bakhmetyeva, Sasha Bonar, Rae Wong, Elizabeth McCumber, Daryl Ann Ingman, Shelby Duclos, Meghan Walker, and Jess Hawks. Promotional graphics by Mary Stratton, photography by Sarah Wolfe, and theme music by Jonah Cohen Sound. A huge thanks to the entire Her First 100K community for supporting our show.
Tori Dunlap
Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over five million women negotiate salaries, pay off debt, build savings, and invest.
Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.
With a dedicated following of over 2.1 million on Instagram and 2.4 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”
An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.
