245. Money Hacks That Actually Work: Side Hustles, Savings, and Free Travel with Chris Hutchins

July 21, 2025

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If you thought “hacking” your money meant clipping coupons or extreme budgeting, today’s episode is going to blow you away.

I sat down with Chris Hutchins, of the All the Hacks podcast, to talk about how to maximize value in every area: spending, saving, earning, and traveling. Chris breaks down real, actionable hacks that go way beyond clipping coupons—including side hustles that don’t require starting a business, ways to “game the system” to cut costs on everything from groceries to luxury hotels, and how to rack up credit card points without going into debt. If you want to stop overspending, learn to travel smarter, or create extra income on the side, pull up a chair!

Key takeaways:

Redefining side hustles: savings as income

Chris expands the definition of side hustles to include anything that saves you significant money—even if it’s not traditional income. From stacking meal kit promotions to flipping iPhones from carrier deals, he reframes cost-cutting as profit. Saving $100 is the same as earning $100—except you don’t pay taxes on it.

Time vs. money: the “value of your time” equation

Chris warns against getting sucked into hacks that only save pennies but cost hours. Instead, he recommends assessing each potential savings opportunity by asking: How long will this take? Is it worth my time? Do I enjoy it? He calls it the “time box” method—only engage with hacks when the return is genuinely worthwhile.

Credit card points are more than just free flights

Chris shares how he started planning friends’ trips just to rack up rewards, why welcome bonuses offer the biggest bang for your buck, and how browser extensions like Points Path and tools like Point.me make redemptions easier than ever.

Flexibility is the ultimate hack in travel

The key to getting outsized value from points isn’t just collecting them—it’s being flexible with your destination, departure airport, or travel dates. Chris and Tori share how they score luxury stays and business class flights at a fraction of the cost by letting the deals dictate where and when they travel.

Negotiating & asking for more

Chris and Tori both emphasize the power of simply asking. From emailing hotels in advance (or pretending you have an assistant-ha!) to negotiating Airbnb prices or asking for free upgrades, these low-effort tactics often lead to high-value perks.

Creative, risk-free ways to explore entrepreneurship

Chris suggests that the best side hustles often come from how you already like to spend your free time. Instead of trying to “pick” a hustle, observe what naturally draws your attention—and explore ways to monetize that interest gradually, without pressure.

Notable quotes

“Spend within your means—but if you’re already spending money, ask: is there a smarter way to do it?”

“There’s these two approaches: I can’t afford this, so I’m going to not do it—or I can’t afford this, let’s get creative so that I can.”

“Book directly with the hotel, email them ahead of time, and let them surprise you. You don’t even have to ask for an upgrade.”

Episode-at-a-glance

≫ 07:01 Side Hustles and Creative Money-Saving Strategies

≫ 20:03 Travel Hacking and Credit Card Points

≫ 24:59 Advanced Travel Hacking Tips

≫ 43:14 Negotiating Airbnb and Hotel Upgrades

≫ 46:58 Finding Unclaimed Money

≫ 55:51 Credit Card Application Strategies

≫ 01:00:16 Teaching Kids About Money

≫ 01:09:23 Bora Bora Travel Deals

≫ 01:12:36 Non-Money Related Life Hacks

Chris’s Links:

Website: https://allthehacks.com/ 

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Meet Chris

Chris Hutchins is creator and host of the All the Hacks podcast. Previously he was Head of New Product Strategy at Wealthfront, co-founder and CEO of Grove (acquired by Wealthfront), co-founder of Milk (acquired by Google) and a Partner at GV, where he focused on seed and early stage investments. He is also the founder of LaidOffCamp, a movement to help the unemployed learn new skills for the evolving job market.

Transcript:

Tori Dunlap:

This is probably the most valuable conversation we’ve ever shared about how to save money on literally anything. From travel to groceries, we are getting all of the hacks.

Chris Hutchins is the creator and host of All the Hacks podcast, a podcast that helps you upgrade your life, money and travel. And boy oh boy, did he bring the heat. We could have talked for three hours.

Chris Hutchins:

I find that the best ideas and the best things come from how you want to spend your free time, and you don’t know their businesses.

Tori Dunlap:

In this episode, Chris completely rewires the way you think about saving money and time. I can almost guarantee that you’ll never look at money or your spending or even your time the same way after listening to this episode.

Chris Hutchins:

That’s where I think it can get dangerous to think about how much value your time is because that space isn’t a profitable time up front. Leaving a day a week or leaving four-hour blocks of time to think and to just mess around on the internet or go for a walk and just get creative, you don’t monetize that time up front, but it’s so valuable in the long run.

Tori Dunlap:

We start the episode by talking about some general hacks, talking about side hustles that could work for you, how you can take advantage from companies to save money on things like coffee, groceries, and so much more.

Chris Hutchins:

See where your passion is. I would say if you could give yourself the space, say, “Oh, I’m going to take a three months sabbatical,” and instead of going in day one, I’m going to start a company. Day one, just be like, “How do I spend my time?” And let it evolve.

Tori Dunlap:

Then we get into the really juicy stuff. This is the episode so many of you have been asking for if you’re trying to play the credit card 201 game, and how to really start getting strategic when you’re thinking about saving money in a way that’s actually worth your while. I’m so grateful to Chris for joining us. You’re going to learn so much from this episode, so let’s get into it.

But first, a word from our sponsors.

You have a show called All the Hacks. Do you have a story that sort of personifies how and when you became obsessed with finding hacks and getting a good deal?

Chris Hutchins:

I think the story that probably… I don’t know if this is the origin story, but I went to boarding school, and most kids who go to boarding school’s, parents give them all the money. They have their credit parents’ credit card. I did not have that. My parents were like, “Here’s a little money,” but I couldn’t afford to buy pizza every night, like all my friends. I was like, “But I want pizza.” The origin story is I wanted pizza. I couldn’t have the pizza, and so I thought, what could I do?

So I started ordering multiple pizzas at night and selling pizza by the slice, not because I thought of it as a business. My thing is how do I do what everyone else is doing? How do I live that life without having to spend the money? So I would buy the pizza, sell the slices and eat my profit, because I wanted pizza and I didn’t have the money to buy it. And so, I think there’s these two approaches of I can’t afford this, so I’m going to not do it. Or I can’t afford this, let’s get creative so that I can. And that’s been the mantra ever since.

Tori Dunlap:

I think for me, in my experience, it’s very similar to yours, where as soon as you find something like that, it almost becomes like a drug. You’re like, how can I do this again? I’ve told the story I think only once before on the show, but my dad would go play golf at the country club he was a member of, and I’m not going to say which one. We would purposely have him tee off at 8:30 at night in the summer because I would carry a backpack and he would get in the lake and we would fish golf balls out of the lake and then go clean them at home and sell the Titleist Pro V1 balls for $25 or something for a couple balls. And so, it’s like once you start doing some crazy shit, you’re like, “Oh, this is kind of fun.”

Chris Hutchins:

And then everywhere you’re walking you’re like, “Ooh, that’s a way to make money. Ooh, that’s a way to do something cool for free. Oh, why is nobody doing that?”

Tori Dunlap:

Okay, so before we get into a lot of the ones that work, can you share some of the stories of the money hacks that you tried that absolutely did not work?

Chris Hutchins:

I think that it’s less about not working and more about realizing you spent, I don’t know, five hours and then you’re like-

Tori Dunlap:

Way too much time.

Chris Hutchins:

I saved 37 cents. I clipped all these coupons, I did all these things and I didn’t actually get any return or I did, and then when I think about the value of my time, it’s just not worth it. So every time I’m buying something online, I used to go and say, “Oh, is there a promo code?” Let’s go search and search and search and search. And I spent an hour and I’m like, “Yes, I got one. It took 10% off my $8 order.”

So I think the majority of the errors are spending too much time. And now I think the process is time box the time, focus on specific things, wait till it’s worth a lot. But there are plenty of times where I’ll use points and book a flight, decide I want to cancel it, but actually forget to cancel it and then boom, lost them all. I make mistakes all the time. I don’t think you can get good at anything without learning the hard way, which is to make mistakes, and I just try to brush it off and cost it up to the cost of education.

Tori Dunlap:

Well, let’s talk about that for a second, because that is my biggest issue with the hacks or the frugality is that I think a lot of people lose sight of the time and effort it’s just going to take to save a couple dollars. So before you decide, “Okay, this is something I want to spend time,” what is the time versus benefit analysis that you do? Even if it’s just like, “Okay, I asked this question of myself before I decide, yeah, I’m going to spend and invest time here.”

Chris Hutchins:

And it evolves. If I go back to high school me, I don’t know what a slice of pizza was, we probably a couple dollars. I was willing to go through extreme lengths for $2. Over time, that number goes up and maybe for me, I’d probably tell you that it’s in the hundreds of dollars, but if I see an opportunity to save $50, realistically, I’ll probably still try to do it, but I’d like to think that it’s crossed over the $100 mark. But I just think, how long is this going to take? What enjoyment do I get out of it?

Sometimes I’ll do things because it’s almost a sport more than it is just a practical way to save money. But I like to look at a purchase and if I’m spending less than $100, I’m not going out of my way to save money on that purchase. If I’m spending $1,000, I’m absolutely going to do it. And if I’m going undergo a massive car home purchase, I’m definitely thinking, what are the angles here? How can I save more? Is there something?

And there might not be, but it’s at least worth exploring. And honestly, we live in this great age where normally you do all this research yourself. Now there’s both content of people talking about it and there’s these AI tools where you could probably go to ChatGPT and say, “Hey, I’m thinking of doing this. What are 25 ways I could save money?” And you could fast track it. I don’t think it’s going to know all of them, but there are better tools now to fast track the process.

Tori Dunlap:

Yeah. So let’s talk about side hustle hacks first. You had a great episode with my friend and yours, Paula Pant, where she brought up the idea that she thinks of side hustles in two ways, gigs and then businesses. Can you talk more about that?

Chris Hutchins:

I’m going to say there’s a third way, but… Yeah. I traditionally have always thought of side hustles as how can I go make money for my time, but in a way that I’m not getting a job? And so is that I’m going to make something and sell it on Etsy or am I going to go drive for Uber or am I going to go be a TaskRabbit and go put together Ikea furniture? That’s always been what’s in my mind for side hustles. And I met this guy and at the time, I mean actually now he still just goes by Kai. He doesn’t share his last name and he has this podcast called The Daily Churn.

And I was listening, and Kai was just, he did the financial independence retire early thing, but he was able to do it early because every time he saw a deal, he was like, “I’m going to dial in and turn that deal into profit.”

And I was like, it blew my mind. He’d look at meal kits and he’d be like, “Hmm, what if I stack all the meal kit promos to replace my grocery cost?” And he was like, “Look, there’s like 10 or 12 companies that do meal kit deals where the first meal’s free.” And he is like, “You know what’s really crazy? You could just cycle through them over 12 weeks and then if you have a spouse, they could cycle through them over 12 weeks.” And then you cancel. And about 12 weeks later they’re like, “Hey, can we re-engage you, do you want another week?”

He basically cut his grocery cost out. Now, maybe that’s not a thing for someone listening, maybe it’s exactly what they want to do, but for him, spending a few hours a week finding these deals allowed him to cut his grocery costs down. And old me never would’ve called that a side hustle because you’re not actually generating income. But if you could find seven different ways to cut all of your expenses in your life out, well, guess what? That’s just as good as income, if not more. Because if you make $10, you’re going to pay taxes on it. If you save $10, you’re not. So this class of side hustle, which I’ll effectively call finding online deals, finding different discounts and ways to monetize your time by saving is arguably just as interesting. Though, I don’t think everyone profitably or confidently thinks of it that way or consistently thinks of it that way at least.

Tori Dunlap:

So we would define gigs as the Taskrabbit, businesses, as what Her First 100K was before I took it full time, of okay, I have to have a business license and I’m maybe a freelancer on the side. And then this third option, which is how can I save money as a way of almost earning money? Is that right?

Chris Hutchins:

Yes. Or even it could be earning. Every year when the iPhone comes out, all these cell phone carriers have these crazy deals where they’re like, “Switch to our cell phone carrier and we’ll give you $1,000 off an iPhone.” And so, one of the things this guy did was he’s like, “Well, I’ll just open up a bunch of phone lines and cancel them after a month, but I end up saving so much money on the cell phone deal and then I just flip the phones and if these carriers are going to give me such a good deal, why not?”

And now, not every carrier is going to let you cancel the line after a certain period of time. And there’s some rules and nuance. So you’re going to the school of hard knocks, learning how to do it is reading the fine print of T-Mobile’s promotion, but that’s definitely something you could do.

And there are people out there, the US happens to sell iPhones for a lot less than they do abroad. And so, there’s these companies called buying groups where you can go buy iPhones in the US and sell them to them. And sometimes you might make no profit on the sale. Sometimes you might make $100, but you also can put the purchase on your credit card and earn those points. And so, this other friend of mine, I think he bought somewhere on the order of 500 iPhones or something on iPhone release day and then just flipped them to people who would pay more than street price because they could resell them overseas.

It’s like to me old V is like, “That’s not a side hustle.” I’m not starting a reselling business where I’m going to go get a little booth at the mall and try to convince people to buy my phones. But it just seems like it’s never been easier to say, “Wow, there’s a deal here. I’m going to turn that deal into profit or savings.” And that version of side hustles is super interesting. So I think I ended up titling that episode How to Make an Easy $3,000 a Month with Online Deals. And we walked through an actual, here are all the kinds of things you can do, and who doesn’t want an extra 30 grand a year?

Tori Dunlap:

I have a very specific example of this. So you know how if you order enough at Starbucks, you get a free drink?And so, I don’t drink a ton of coffee. I’m not a daily coffee drinker. I had one this morning, so I was just like, “I want something fancy in my life.” But you can get, when you get enough points to get a free drink, it can be the biggest drink. I will order a cold venti drink and then drink half of it, and then save the half for the next day. And it’s one of those very specific things that’s like, “Okay, it’s free. I’m going to get the most of the free thing I can get and then parse it out over time.”

Chris Hutchins:

And look, that cost is maybe on the order of magnitude of $4 to $5, but god, it feels good. It feels so good when you get something for free. And when you don’t overpay for something, that feeling is a rush of endorphins that can sometimes exceed the dollar saved. And I don’t know, you don’t get those that often in life. Life sucks sometimes. And so, if you could get a huge win by getting the two coffees for the price of one, awesome.

Another fun Starbucks one is there are a couple credit cards that give you credits when you spend money at Hilton, like the Amex business Platinum, some of the Hilton cards, they have Hilton credits. Well, it turns out that a lot of Starbucks are in Hiltons, and so if you don’t want to have to go stay at a hotel to get this credit, you could go pick up Starbucks at a Hilton and get your credit that way. And I was at a nerdy conference for people that are obsessed with points and miles and it was like, “Let’s all walk three blocks to get our coffees at this Hilton because everyone’s coffee’s going to be free because we all have a card that’s going to give you some credits for spending money at Hilton.”

Tori Dunlap:

That’s funny.

Chris Hutchins:

So finding those little things to just feel like you’re pulling one over the system, I love it.

Tori Dunlap:

So we have a lot of listeners who want to start side hustles or businesses, but they feel stuck on what that side hustle should be. How do you guide someone through figuring that out?

Chris Hutchins:

So my principle, I think I probably started, I don’t know, lots of companies that haven’t worked and two companies that took three years to realize didn’t work. I find that the best ideas and the best things come from how you want to spend your free time and you don’t know their businesses. I find that it’s really hard to just think, what do I want to do and just find it. But if you give yourself the free time to see, “Oh, I have 10 hours a week, how do I spend it?” And then you slowly evolve to realize, “Oh, this thing I love doing actually could be valuable to other people.” And maybe you love knitting. And it’s like, well, do you want to keep knitting and sell what you make? Do you want to start a knitting blog? Do you like talking about knitting? Do you like showing people on video how to knit? Do you like finding the best knitters and reselling their amazing stuff? Do you want to create a marketplace?

See where your passion is, and instead of just doing the academic exercise of thinking about it, I would say if you could give yourself the space, say, “Oh, I’m going to take a three month sabbatical,” and instead of going in day one, “I’m going to start a company,” day one, just be like, “How do I spend my time and let it evolve?” Because my full-time job and my wife’s full-time job is to run a podcast and a newsletter. But when I started the podcast, I was working a day job at a company called Wealthfront, like a FinTech company, and I actually started working there and I asked if they wanted to own it. I was like, “Would you guys be up for giving me like 25% of my time to work on this and you guys can own the podcast?”

And I couldn’t appreciate the fact that they said no more than anything in the world right now. But at the time, that’s how little of an ambition I had to turn it into a thing. I was just doing it because I really wanted to do it. And I wish I had a friend at the time who was like, “No, no, no, don’t even offer.” Fortunately I was lucky, but it came out of how do I want to spend my free time? And so, look at how you spend your free time, talk to your friends about what you’re best at. I love calling a friend and be like, “Why are you my friend? What is it about me? What do you tell stories about me? What am I the best in the world at?” And just go down that rabbit hole and explore it. But you need space for that.

And that’s where I think it can get dangerous to think about how much value your time is, because that space isn’t a profitable time up front. Leaving a day a week or leaving four hour blocks of time to think and to just mess around on the internet or go for a walk and just get creative. You don’t monetize that time up front, but it’s so valuable in the long run.

Tori Dunlap:

Yeah, I have a formula that I talk about in my book to determine your side hustle and I call it the three T’s. So it’s time, talent, treasure. exactly what you were saying. How much time do you have and how much time do you want to spend? Talent, what are the talents you already have or do you need to cultivate a new one if there’s a certain side hustle you want to do? And then treasure is like how much money do you want to be making and are you okay if it doesn’t make money for a while? Her First 100K, I had lofty ambitions for the company, so I was okay if it wasn’t profitable for a while, while I built it up. But for some people they’re like, “No, I just need money right now.” So that’s going to be a different thing that you choose versus something that might take a little bit of runway to get started.

Chris Hutchins:

Yeah, one book that I really enjoyed was called, I think it’s Burn the Boat-

Tori Dunlap:

Burn the Boats? Yeah.

Chris Hutchins:

Matt Higgins. And I had him on. We had this discussion about psychologically when you create a plan B, it can actually hold you back. So one thing I’d encourage everyone to do, read that book, listen to an interview with him, it’s like don’t worry about if it’s not going to work, that is going to make it harder for it to work. So it’s not just like a waste of time, but it actually has a psychological impact on the success of the thing. And when I see the most successful entrepreneurs, they are just so all in, pot committed to everything they can do to make this thing work.

And when you ask them, “Well, I don’t know, what about this other company that’s doing something?” They’re like, “I don’t care. We’re going to win.” And that mindset is great for massive companies, but if your goal isn’t to go build the next billion dollar thing, maybe it’s prudent to understand what your competitors are doing. It’s like you said, treasure. It needs to scale with what you want it to become. And I have two young kids, I’m not interested in empire building at this stage in my life because I know the time commitment that goes into that and I’m not willing to make that trade off, which means this business isn’t going to 10 x next year, and that’s okay. But maybe those kids go off to college one day and I’m stuck with lots of free time. Maybe that’s the time I want to go build an empire and that’s okay.

Tori Dunlap:

Well, and it’s also dependent on the life stage. I think we hear from a lot of people who do not have the time to think about, and I always say on this show, side hustle is just a glorification of the word second job. Side hustle for some people is absolutely necessary in order to get by and live their life. And so, I think what you were talking about before of are there small ways that you can, quote-unquote, game the system that don’t involve a ton of extra labor, don’t involve you commuting somewhere, don’t involve you having to put a bunch of upfront costs and are just like, okay, can I do these small things that maybe save me a little bit of money, put more money back in my pocket?

Chris Hutchins:

Yeah. And I’d encourage you, anytime you find something that you think is a deal, you as a child, you’re like, “Wow, all these golf balls are free.” It’s one thing to say, “Now I have 10,000 golf balls,” but you might not have even golfed. Look at anytime you see something that you think might be a deal and push yourself to think, “Is there any way that the fact that I found or know about this deal that I could turn that into income for other people who want to deal?”

And so, young you said, “Here are all these golf balls, I found them for free. Other people buy them, I can sell them.” And so, whether that’s a sale at the grocery store, sometimes that might be the deal. I know people that buy grocery store gift cards at Kroger and resell the gift cards when they go on sale, but they keep all the Kroger fuel points so they can fill up their car for free. There is always an angle anytime you find something that feels like a good deal. So if you’ve become a good deal seeker, it doesn’t have to just be to save you money, it can also be to make you money.

Tori Dunlap:

When we come back, we’re getting into the most in-depth conversation we’ve ever had about credit card points, from travel to points and everything in between. I’ve been doing this for years and even I learned some mind-blowing information. Stay tuned.

So the one hack that I think is such a valuable spend of your time and research and energy is the credit card point ecosystem. And we have talked a lot, especially this year, we had Brian Kelly on, we had my friend Janelle Onajet on, and I’ve talked a lot about it on the show too, of ways you can use your credit card in a smart way. So how did you start travel hacking in the first place? Let’s walk through those early years of you travel hacking.

Chris Hutchins:

I mean, the early years were so unoptimal, was I just went on some flights, I accumulated some miles, I didn’t really know what they were. I needed a credit card. I was living in Colorado, because I went to school there. So I opened a United card.

Tori Dunlap:

That’s most people. Most people open a card that somebody is like their dad is like, “This is card’s a good one maybe,” and then that’s most people.

Chris Hutchins:

And then I remember a very distinct moment where some kids that were maybe one or two years older than me that I’ve become friends with, they were like, “We’re all going to rent a house in Mexico.” I think it was in Puerto Vallarta or Cabo, I can’t even remember at this point. And I was like, “I want to go.” And then I looked and I was like, “Oh, that flight’s like $400, I guess I’m not going.” And I was like, “Oh, I have all these miles. I wonder if I could use them.” And then I was like, “Oh my god, I can go to Mexico,” and I paid, I don’t know, 10, $20 of taxes and fees. Was it the best deal for those miles? I don’t care. Because it was the most amazing thing. It was the difference between going and not going to Mexico.

And so, I will say when you learn how the game works, sometimes it can be debilitating because you’re like, wow, I know I can get incredible value if I do this other thing, but I want to encourage people to realize that if you don’t get the best value in the world, but you get to go on a trip that you couldn’t have otherwise gone on, that’s an amazing value. And so, that’s where it started, was I went on one trip that I could never have gone on. And then I was like, “these points are incredible.” And I was like, “why don’t I open up these two American Airlines credit cards? Why don’t I start doing whatever I can to accumulate points?” And I would say, I’m sure you’ve talked about, “oh, these welcome bonuses can be lucrative. Open up a card, someone’s going to give you 75, 100, 150,000 points.”

One of the things I did earlier in my career, because I just wasn’t spending a lot of money. Sure, if I had a business that was putting a million dollars a year on a credit card, I’d be racking up points, but I didn’t. But every time a new trip came up in the future where friends were like, “Let’s go here or let’s do a bachelor party,” I said, “Okay, great. Can I plan it? I will plan the bachelor party.” And everyone’s like, “Really? You want to do all that work? And I was like, absolutely. We need to book six hotel rooms. I’ll book all of them. I’ll put them all on my credit card. We need to book eight flights to Vegas. Great. I’ll buy all eight flights.” And so, I made sure I had a card that earned a lot of points on travel and hotels and flights and I was everyone’s travel agent. And then I’d be like, “Hey, if you want to pay me, send me some Venmo,” send me some whatever the app of the day was and I’d probably-

Tori Dunlap:

[inaudible 00:23:22] check.

Chris Hutchins:

Some of it was like a check.

Tori Dunlap:

Yeah, write me a check.

Chris Hutchins:

But I was able to spend so much more than I actually spent. And that was the early way in which I was starting to accumulate points faster than just opening up lots of cards. Because earlier in your journey I will say you could open up 10 cards and you’d be surprised that your credit score will probably go up. It’s a counterintuitive thing. And there’s somebody that posted this thing about he and his wife opened up, I think it was like 26 cards over 18 months, and both their credit scores went up. They accumulated 2 million points and they went on a bunch of trips.

So I wouldn’t be turned off by the credit score thing, but I would also look creatively at is there a way that I could be spending more without spending more? Just to be clear, I’m not suggesting you just ramp up your spending. I absolutely am not suggesting you don’t pay off your balances. Spend within your means. But if you work at a company and they’re like, “Hey, you don’t have to file expense reports if you use your corporate card,” but you could use your personal card and maybe if you’re going out for a coffee, it’s not worth the hassle. But if you need to buy an international flight, maybe that time it’s worth using your personal card and going through the hassle of the expense report so that you can keep the points.

Tori Dunlap:

For all of the basics of what we’re talking about here, I’m going to send everybody to episode 213. That’s the one we did with Brian Kelly because I really want to double click on all of the crazier shit. So if you want the sign-on bonuses, if you just want to understand generally how credit card points work and how to redeem them, that’s a good episode to start with. But let’s talk about the walk four blocks to get Hilton. What is the crazy shit? I’ve seen people with the binders of 70 cards. What is the next level unhinged for people who are ready? Oh, is that… Oh my god, you’re one of them. How many you got in there?

Chris Hutchins:

Probably at least 50.

Tori Dunlap:

Holy shit.

Chris Hutchins:

Between me and my wife. Some old debit cards. Costco cards.

Tori Dunlap:

Yeah. Wow. See, I’m not even this bad. I talk a lot about I got this trip for free or I got this hotel stay, but I have eight cards, seven cards, and just the average person, that’s a lot.

Chris Hutchins:

That’s crazy.

Tori Dunlap:

I use only two or three on a semi-regular basis.

Chris Hutchins:

I built a model where I put in every credit card that could be good. I put in both Bureau of Labor statistics spending data and my own spending data. And I was like, where is the optimal point on the curve? Is it to have 27 cards? If you had every card under the sun and you used it optimally, you would earn more points than if you only had one or two.

But I will tell you, the return going from one to two is massive and the return after two really, really diminishes unless you spend a tremendous amount of money for work or personal in specific areas. So when it comes to what cards do you spend on, I think everyone should get a card that has elevated return on whatever they spend the most on. Travel, dining, groceries, whatever. And then everyone should have an everything else card. I think the Bureau of Labor Statistics best too would be the Amex Gold because you get 4x on dining and groceries and something like the Capital One Venture card where you get 2x on everything else, that would be the staple. I just want to make sure people see a binder full of cards and they don’t think, “Wow, in order to do this optimally, I need all these cards.”

Tori Dunlap:

No

Chris Hutchins:

My general framework is you really only need two or three cards for all of your spending. And then if someone’s like, “Hey, this week we’re going to give you 100,000 points,” okay, I’ll take the bait and I’ll make sure that I use all the perks that come with it so that if there’s an annual fee, I’ve netted it out. And then at the end of the year, if I’m still going to be paying an annual fee and I can’t get my value, I’ll reach out and say, “Hey, is there any bonus if I stick around for a year?” “No.” “Great. Can I just change this to another card that has no annual fee?” “No.” Okay, I’ll cancel it. And some cards, like these Hilton cards, the Hilton Aspire card gives you a free annual night every year. And so, me and my wife have a couple of them and we’ve been able to stay at properties that cost, I don’t know, more than $1,000 a night for a card with an annual fee of $500.

And I probably am at the stage in my life where maybe not a $2,000 a night hotel room, but I would spend more than $500 a night on that hotel room. So why not keep that card open? Am I spending money on it all the time? No. So it doesn’t hurt you to keep the card open if there’s no fee or if you’re getting value out of it, but I’m not spending money on all of these cards. The reason they’re in this binder is because I leave it at home. I don’t need to carry it.

But when it comes to some of the, I don’t know, ninja crazy stuff, let’s think about it. I mean, the welcome bonuses, I ran this analysis… If you can’t tell, I really like making spreadsheets. And I took, at some point, I think it was late last year, I was like, what are the top 20 bonuses cards will offer you to open up the card? And the average return, meaning if a card said, “We’ll give you $1,000 for spending $1,000 on the card,” that would be 100% return. They’re going to give you your entire money back. The average return was 17% or somewhere on that order, it’s like 16.7 or 17.3. You and I both know there is no credit card that offers you 17% cash back. Maybe in a perfect world you’ll find a card that earns 5% on one category up to maybe a cap per year.

Tori Dunlap:

That revolves every three months too. That 5% category is only there for a quarter. Yeah.

Chris Hutchins:

Yes. So if you’re saying what’s a baseline? Maybe Robinhood has a 3% card, doesn’t work well for Business. Bank of America, if you put some money on deposit, it’s like a 2.6% cash back card. So 17 is incredible. So hands down, your best value is to always be spending on whichever card is going to give you the best return on a welcome bonus. That is the optimal way to spend. But if you don’t want to open up 15 cards a year or even five or six, I could say just pick one or two and focus on that. But those welcome bonuses, I would argue are the place to focus. And if you have a partner that you’re playing this game with, it’s not a one plus one equals two, because you could open one card, then you can refer your partner to it, get some kind of referral bonus, then they could open up a card and now you get the same bonus twice plus a referral bonus.

So that is where it starts to get really fun. And I have a friend who every time there’s a big welcome bonus, he not only signs up for it, but he refers his mom, his dad, his sister and his partner. So he’s getting four welcome bonuses for them, four referral bonuses and one welcome bonus for him. And he is just printing points at this point. And that is where it starts to get really fun, is starting to figure out how you can help the whole family and take big fun family vacations. But that’s all on the earning side. I think that a lot of people listening have probably been doing that to some extent. They probably opened up a card, they probably earned tens of thousands, hundreds of thousands, maybe a few people crossed the million mark. And they’re like, “But what? It’s just so hard to use these points.”

I feel like I wonder if people give up, and I’m sure Brian talked about it, so I don’t want to go too deep. But the one thing I’ll say is it’s never been easier to find out if your points can get outsized value, because there’ve been all these tools that have launched recently. One that I don’t know if you talked about is called Points Path. It’s a browser extension that layers on top of Google Flights and it only works for the major US airlines, but it’s like I’m searching for a flight on Google Flights and it’s like, “Hey, on United, if you use your United Points, it’s a better deal with points.” You don’t even have to use another tool. I mean, technically you’re using a tool because it’s a browser extension, but you’re not going to some miles and points tool or paying a subscription. It just sits where you live. And so, that’s one where I think it can easily help you optimize without even having to think about it. There are others, there’s PointsYeah, and AwardTool

Tori Dunlap:

For those who are listening on audio, I now have another tab open and I am signing up as we speak. Point.me is a partner of ours. That’s the other one I love of seeing, yeah, I want to go this place at this time, or you can be more general than that to see what my points are going to get me to.

Chris Hutchins:

Yes. I would say find a tool that you like for when you’re searching for a flight and take a few minutes, not hours to say, “Hey, I’m looking to go from here to here. Is there a better deal with my points? No? Great. Let’s save them for the next trip.” I find that the more flexibility you have, the easier it is to get really, really outsized value. And so, flexibility doesn’t mean dates. It could mean where you go. It could mean how far in advance you plan it. Sometimes my wife and I’ll say, “You know what? We really want to take a vacation and we don’t have any flexibility. It’s spring break. We are going this week, but we’re really flexible where we go. And you know what? If we don’t decide until a month before we’re okay.”

And so, some of these tools have alerts and so you can basically say, “Hey, I’m looking to go to Europe.” You search, I can’t remember Point.me has this yet or not. I use Point.me a lot because I think they have one of the best sets of all partners.

There’s another tool called Point, yeah, an award tool. And I’ll say, “Hey, San Francisco to Europe, set an alert for the date I want.” And I might set it six months in advance and maybe three months later I get a ping that’s like, “Hey, San Francisco to Paris. 50,000 points in business class,” which had I redeemed those points for, I don’t know, Amazon, I probably would’ve gotten like $300 or something. And so, now I’m here, I am going to business class for something that is way less than that, all the way to Europe. So don’t be afraid to think about flexibility outside of just dates. It could be where you go. It could be when you go, whether you change planes.

And then think about trying to get places not necessarily from where you live, which might sound crazy, but a lot of the things these search tools do now is, “Give me a flight from the west coast to Asia,” and you’re like, “I want to go to Japan, or I want to go to Hong Kong. I’m willing to fly to L.A before I get…” Because it sounds crazy, but sometimes I’ll find flights where it’s the hard leg to get to Europe, isn’t L.A. to Paris, it’s San Francisco to L.A. But you can buy a San Francisco to L.A flight for 60 bucks sometimes. So don’t lock yourself into only leaving from or going to a specific place.

And then I’m going to throw a curveball here. I recently came across this perspective shift, and when I say All the Hacks, when I talk about my show, it doesn’t have to be a little trick. It could just be something that opens your eyes to a different way of thinking. So we were planning this summer trip and we found this hotel on the island of Majorca in Spain. And if anyone ever gets a chance to stay there, it’s called Cap Rocat. It is unbelievable. It’s built into a fortress. It’s the pinnacle of luxury. It’s amazing. And I think when we were looking to go last summer, it was like $2,800 a night. That is past the threshold of what I will spend on a vacation.

But the reason we found it was because I was using this tool called Rooms.aero, and I just went to Hilton, Small Luxury Hotels of the world and I was like, “What is available anywhere in the world in the month we want to go for four nights?”

And it was like, “Cap Rocat is available.” And I was like, “Great.” It was 120,000 Hilton points a night. Now, I happened to have that many Hilton points or free night certificates. But here was the crazy thing on that day, just for fun, as I was going to book it, Hilton said, “Hey, we’re having a sale on our points.” On the Hilton website that day, you could buy 120,000 points for half a cent each, which made it $600 per night. So let’s pretend you’re listening to this and you’re like, “This points and miles shenanigans, it’s not for me. I’m a cash person. I love cash back.”

Great. But if you’re going to the Hilton site and you’re about to book this thing, that’s $2,000 a night and you could just buy the points to book the exact same thing for $600, I don’t know, seems like a great opportunity, and points and miles go on sale all the time. And so, you can use these tools to say, “Is there a great points and miles deal to get to Japan, to get to Paris,” to get wherever you’re going? Even if you don’t have the points, one of the airlines that you can use to book that flight. Because one of the things to know is a flight on United is bookable by United, but it might also be bookable by Air Canada or Avianca Life Miles these other carriers.

And Avianca as an example, a Central American carrier, their points and miles go on sale all the time. And there are times where you’ll be like, “Wow, I don’t have 100 thousand points to get to Europe, but boy, do I wish I would because I could fly business class.” And oh, it turns out Avianca is selling these points for 1 point something cents. And so, you could just buy it there and book it. Now, I would encourage you to make sure it’s available, get to the checkout screen before you buy the points because if you don’t, you’re stuck with a bunch Avianca points.

But I don’t know, it’s this mindset shift where I was always all in on points. Now that I realize there’s the opportunity to buy them and use them, it just made me wonder, are there times where cashback might be better? I earn all this cashback, I invest it, it grows, and then when I’m ready to go on a trip, more often than not, I might be able to just use those points or use those dollars to buy the points and go on that same trip, get that crazy outsized value without having to even play the points game.

The answer is for me, no, I’m still doing it. But for someone who doesn’t want the overhead of points and miles, you can still benefit from points and miles by buying those points on sale.

Tori Dunlap:

Everybody listening, you need to go back about 15 minutes and you need to listen to all of that again. No, it’s so good. I know I just said it, but I mean it. Go back and re-listen to all of that. Take notes. This is probably the most thorough conversation we’ve ever had about travel credit cards and traveling for free or at major discounts. When we come back, we’re getting really granular about what this process looks like from step one all the way through checking into your hotel. We’ll see you back here shortly.

The thing we keep coming back to in all of these episodes is you can be as crazy about this as you want. It can just be, “You know what? I don’t want to spend a lot of time on this.” Or you can spend a million years on this and you can hack it all you want. The thing you said about being really flexible is something that single-handedly changed my travel experience. I would go on what we called Friend Moon with my friend. We would go on a trip every year, but we would let the deals determine where we went because we were super flexible of like, “Oh, okay, there’s a deal to New Zealand. I’ve always wanted to go to New Zealand. Great.” We wanted to go to Morocco, but there were no deals from Seattle to Morocco was extremely expensive, but guess what? Seattle to London was a deal and then a Ryanair flight from London to Morocco.

So you can start to think about ways to be more flexible with your travel that are both just the deals, but then also the credit card points, to your point of, okay, I want to potentially go at this time or even just this area, get me close. This is what I just did. My partner’s family, somebody was getting married in Italy. If I tried to go Seattle to Italy, it was a specific time last year, it was going to be so much money. But I found us a deal from Seattle to Frankfurt, Germany, and then hopped on a Ryanair flight from Frankfurt to the Amalfi coast. That’s what we’re talking about here.

Chris Hutchins:

And it’s always funny that you’re probably sitting here, you get off this business glass flight in Europe and you’re like, “All right, where’s the economy check-in counter for Ryanair?”

Tori Dunlap:

Chris. That is the funny thing, and I’ve been meaning to do a post about this the year before we went to Paris, lie down flat seats. It was my first ever business class flight. The first time I ever turned left on a plane and it was thrilling. It’s like five course meal in the sky. All you can drink champagne, full lie flat seat with a bed. We got off, we took the bus to get to our hotel or our Airbnb. It wasn’t even a hotel, it was the Airbnb and that I found that was nice and clean, but pretty cheap. And then we got on a Ryanair flight from Paris to Scotland, where we actually wanted to go. And then I checked us in at the Balmoral, which is a literal castle and is a $900 a night hotel that I did with credit card points.

And again, we took a bus from the airport to get to there. So it’s like you get to choose where you want to spend your money or spend your points. And I think that the incredible thing about all of these hacks, especially around travel, is you and I are not spending $2,500 on a hotel room. We probably could. I refuse. That is an obscene amount of money and for the average person listening, that is way outside your budget. But you get to have these once in a lifetime experience. You get to stay at the five star hotel where they say your name when you walk in the door. You get to have the experiences that you could not afford otherwise because you’ve done a little bit of due diligence, trying to figure out how to use these miles effectively.

Chris Hutchins:

Yes, I got two quick things. One, there’s this thing called the Dunning-Kruger effect, and it’s like this cognitive bias theory. The way this works is when you have really low competence on something, you’re actually way less concerned with being optimal. And you could use your Amex points for Amazon and feel good.

And then you go through this… I just did this episode, but this woman, Devon Gimble who has really thought deeply through this, it’s like once you learn… So for some people that will be this moment. You have this moment where you’re like, “I’ve been doing it all wrong.” And now you don’t understand how to do it, but you know that what you’ve been doing is wrong. Or not wrong. Wrong is the wrong word, but it’s not as good as it could be. And I want to encourage you to not feel… This is a not fun place to be.

You are not yet an expert, but you have just enough knowledge that you’re doing it wrong and it feels bad. And I just want to let you know, the more you think about it, learn about it, experiment with it, you’ll climb back out of that valley of despair if you will, and it’ll be amazing. And so, we had this episode where we talked about you start at the top, then you’re like, “Oh my gosh, my entire life could be so much better off, but I don’t actually know how to do it,” and you feel awful. And if that’s you, there is hope. We have all been there. And then the other side of that valley is amazing. I want to flag that.

I also want to say on the Airbnb front, because some of these optimal hacks, tips, tricks don’t have to be points and miles. I met a host of an Airbnb, and I don’t know how it came up, but the idea of negotiating your Airbnb came up and they were like, “Yeah, about 50% of my guests negotiate the price with me.” And I was like, “What?” I am a deal seeker and I didn’t know that you could negotiate Airbnbs. Turns out you can, and I’ve used it and it works. So it sounds like you have done this also.

Tori Dunlap:

Yep, absolutely. I negotiate every Airbnb, especially if I’m a return guest. So if I went to an Airbnb and I really liked it and they knew I was nice and clean and didn’t throw a rager and I’m going back, I’m like, “Hey, I was lovely to work with last time. I will be lovely to work with again.” Or especially if I solo travel or I’m just with one other person and we’re renting a place that has multiple rooms. This is actually what my friend and I did in New Zealand. There was multiple bedrooms that we weren’t going to use, but it was in a killer location and it was a little outside of our budget. And I said, “Hey, if you can give us…” I don’t remember what I asked for, like 20% off or something like that, “We’re not going to use that bedroom, so you’re not going to have to clean it. And it’s just me and my friend traveling. We’re two women. We will book right now.” And they gave it to us.

And again, the recurring theme, one of the recurring things of this show is, why not ask? Yeah, you might hear no, but you might hear yes. And that’s fantastic. Even negotiating, I mean, I always ask for a room upgrade at a hotel. Always. And they don’t know who I am. They don’t know. I have millions of followers. They don’t know I’m an influencer. They don’t know who I am. But I just go, “Hey, do you have any complimentary upgrades you could offer me?” And let’s call it 30, 40% of the time, they’re like, “No, I’m sorry, we don’t.” “Okay, no worries.” And some of the time they do, and I get a really nice room out of it for free just because I asked.

Chris Hutchins:

And you can ask without asking. So one of my favorite things to tell people to do if you hotel, book it directly with the hotel.

Tori Dunlap:

Absolutely.

Chris Hutchins:

You book on Travelocity, Expedia-

Tori Dunlap:

Booking.com. Yeah.

Chris Hutchins:

It’s not that there’s a flag on yourself, but book it directly with the hotel. Find an email address, call and ask for one, and send them an email in advance and say, “Hey, I just booked this thing for three nights. Here are my dates and my confirmation. I’m really excited to stay with you. We’re celebrating my husband’s birthday,” whatever it is. And you don’t have to ask in that moment because hotels love hospitality. And I guarantee that some percentage of the time that’s probably close to or above 50%, you will show up at the hotel and something will happen. Whether it’s champagne, whether it’s free drinks at the bar, an upgrade, a better view, sending an email to the hotel in advance is one of my all time favorite tips because it costs you nothing.

You’re not even asking. For people who are uncomfortable, you don’t even have to say, “Can you upgrade my room?” Just let them do the thing that hospitality companies like doing, but book directly with them so that they know you actually are interested in building a relationship with them. Because if you just book on the internet with TripAdvisor, they might not even have your reservation until the day before you check in because of the way this whole system’s work. So book direct.

Tori Dunlap:

And if something goes wrong, you are working through Booking.com or Expedia’s customer service, you are not working with the hotel. So if you have to cancel or something goes wrong, yeah. Chris, I’m going to add a hack to your hack.

Chris Hutchins:

Love it.

Tori Dunlap:

If you are emailing them, which I highly recommend doing as well. Email is your fake assistant.

Chris Hutchins:

I love it.

Tori Dunlap:

They don’t need to know you don’t have an assistant. I literally have an assistant, but I don’t make her do this, because she’s got better shit to do. I have made up an assistant. And by the way, it’s a dude because dudes get usually more respect, unfortunately. Scott emails all this time. Scott is the hard ass. Scott will come in and be like, “Ms. Dunlap is coming at this time.” Make up an assistant. Again, you don’t have to be an influencer, you don’t have to have a podcast. Make up your assistant because you’ll get so much new shit. It’s so fun. It’s so great.

Chris Hutchins:

It works. These things work. Because you don’t have to-

Tori Dunlap:

They work.

Chris Hutchins:

There are hacks that take a lot of time, but one of my favorite ways to find a little extra income that for 10% of my audience, we did a poll, resulted in hundreds of dollars of money. And maybe you’ve talked about this before. But whatever state you live in, go to the state’s unclaimed money database and search for yourself. And yes, some of you will be like, “I found nothing.” Some of you’ll be like, I found that I’m owed $3, but it’s going to take me an hour to figure out how to get it back.

I would encourage you to do that anyways because if you don’t, someone can probably find your address. It’s a good way to reverse engineer what is someone’s address. But some of you will find hundreds of dollars, a few of you will find thousands of dollars. So it’s a great way to just check if there’s any free money out there for you. I like using it as my dinner party thing, because you know someone’s address, because they’re going to dinner at their house, I’ll just search it up and come over and be like, “Hey, we brought you a bottle of wine, but did you know that Verizon owes you $400?”

Tori Dunlap:

That’s so good. I’m like, “I’m making you money, and I haven’t even stepped foot in your house yet.”

Chris Hutchins:

Yeah, father’s days around the corner. I couldn’t figure out whether to get you tie or socks, but I did find out that Aetna owes you $1,300 from seven years ago. Dad’s going to be stoked.

Tori Dunlap:

So you’re welcome. Yeah. That’s so fun. Okay, so we were talking about travel hacks, and again, this is the thing I could talk about forever. So can we start at the beginning of booking the trip? So the flight, what are the hacks? Obviously points, we’re checking. I love that tip about can you buy miles. Not just like Hilton points, but you can buy Alaska Airline miles or Delta miles. So what other hacks around the flight as we’re planning the trip, can we be thinking about?

Chris Hutchins:

Okay, I think there is a lot here. So when I’m thinking about booking a flight, there’s probably… I did this episode with this guy, Zach Resnick, and I can’t remember what number episode it was, but we went through a checklist of 25 things you can do.

So checking if it’s available for points. We talked about that. Buying points, if you can. Looking for gift cards. Sometimes airlines have gift cards on sale. So right now, at least in the Bay Area, you could buy Alaska gift cards for 10% off. Very often, Southwest sells their gift cards at Sam’s Club and Costco for 10% off, I think, or maybe sometimes 14% off. So that’s one.

Tori Dunlap:

Chris, can I pause you for a second?

Chris Hutchins:

Yeah.

Tori Dunlap:

Can I just… We have to talk about Costco. That’s a hack in and of itself is I… Everybody knows this because I’m from the Pacific Northwest Costco. If they reached out and they’re like, “Tori, we need a kidney,” I’d be like, “Which one?” I love Costco so much, but they do a lot of you can go in and buy the cards and then you exchange them for the stuff at the register. But right now they’re doing a three-day park hopper pass to Disneyland, and I’m a huge Disneyland addict, for way less. I think it’s like 75% off and it includes a meal ticket or something. But Costco’s your secret weapon both for Costco travel, renting a car, getting gift cards. I love Costco just as a hack for things beyond the rotisserie chicken. So you mentioned Costco. I can’t not talk about it.

Chris Hutchins:

I mean, we haven’t talked about it, but I have two Costco things on my desk. One is a Costco membership. The other is a rack, which you might not know what this is, but it’s from Pamp, which is a Swiss company that makes gold, and I asked for an extra one. It’s one of the racks that Costco puts gold on in their storeroom.

Tori Dunlap:

Oh yeah.

Chris Hutchins:

Because I probably bought hundreds of thousands of dollars of gold at Costco in the last six months, and I’ve started a gold reselling side hustle that is quite lucrative. So Costco is amazing. We can come back to that, but I want to hit on all the flight things.

Tori Dunlap:

Yeah, sorry, I just got excited. You had said Costco and I was like-

Chris Hutchins:

No, no, I love. Look, believe me. Two weekends ago, I think we went to Costco five times, more because the limitations on gold purchases and the number of Costco is in the area, but a few other things. So there are rare cases where a travel agent is going to get you a deal for a flight. I would say if you are flying internationally, especially if it’s one-way, there might be some obscure options. I will say if you’re booking a one-way flight international, you are going to be faced with an outrageous price. And if you just simply change it to a return, a round trip, even if you don’t need the return, the price will go down.

And so, I had a friend who has way more money than I do and he was like, “I’m looking to go to Europe. It’s just a one-way ticket. It’s like $9,000.” And we added a return in economy and the entire ticket went from 9,000 to 4,000. He saved $5,000 by adding an extra flight. The same thing is sometimes true. There’s this website Skiplagged, which basically does what’s called hidden city ticketing, where it’s like, well, flying from San Francisco to New York is $500, but flying from San Francisco connecting to New York and going to Boston is $300. You could if you weren’t checking bags, get off in New York and miss your flight to Boston.

The airlines don’t love this, so I wouldn’t do it a ton, at least not if you have your frequent flyer number on the account. But if you’re doing a one-time trip to Asia, and I don’t know, Japan Airlines is $1,000 if you fly through Japan to Taiwan, and it’s $4,000 dollars just to Japan, I don’t know, that’d be a case where if I’m not checking bags, I’d be willing to take the $3,000 savings on a one-off case.

If you’re flying a ridiculous amount, I would say do everything you can to become friends with someone that works at the airline and encourage them to make you their buddy. There’s a gray market for brokering these buddy passes, but I would say it’s very gray. But if you found the right airline… We talked about this in this episode where it’s like how do you go about getting those things? I think it’s episode 156, and there is a way to do it. I was like, “Should I just be reaching out to people on LinkedIn?” I don’t travel enough and I have a family so it’s not worth it. But if I were single, traveling a ton and maybe taking a sabbatical, I would do everything I can to find out if I know anyone that works at an airline that might be able to make me one of their partners.

If you do have a company, most companies can enroll in the business program of the airline and it might only be 3, 4 or 5% off, but I don’t know… My principle is every time I’m buying something, whether it’s a new toilet at Lowe’s or it’s a flight, it’s like what’s my checklist of all the ways to save money? Can I buy a gift card? Is there a shopping portal where I could use Rakuten to layer on some extra points? Is there a coupon or a promo code? Am I using the card that gets the most points? Like all of the things every time. I don’t know, I think that’s the most of it on travel portals.

I will say you and I have a similar belief that booking on Expedia for a hotel can leave you in a frustrating situation if you need to change things. So I rarely will do that. You also might not, if you had status with Hyatt, you might not get any elite nights. You might not get treated well because they’re not always required to do any of those things for third-party bookings.

On the airline side, things are evolving, and so keep an eye on this evolution. There’s this thing called NDC, which sounds like it could be a cool thing. It stands for new distribution capability. It’s like the dumbest moniker, but it allows these travel portals to book flights with airlines as if they were booked directly with the airline. You can still manage them with the airlines, you can still change things. As these travel portals adopt these platforms, you won’t have that problem with flights.

And so, Capital One, the VentureX card gets you 5x points on flights if you book in their travel portal. I may be questioning whether I want to do that depending right now on whether my flight will change, but in the future if that travel portal adopts this, which honestly I don’t know how you would know if it did yet, but they’ll probably do some marketing around it. I’ll certainly be talking about it on my show and newsletter. Then I’m down to go book in a travel portal to get more points.

Tori Dunlap:

Oh, that was so good. When we come back from a word with our sponsors, we’re wrapping up our conversation with Chris by talking more about credit card points and other ways for you to hack your everyday life, including how Chris is teaching his kids about getting better with money. We also talk about how to know when a deal is actually worth your time versus a waste of your time. Stay tuned.

Something you’ve brought up in one of your episodes on your show that we haven’t talked about on ours is the 5/24 rule. I don’t even know what this is. Tell me what it is.

Chris Hutchins:

So almost every credit card issuer, meaning bank has rules that they typically use to decide if you’re eligible for a new card. Chase is notorious for this 5/24 rule, which is if you’ve been approved for five credit cards in the last 24 months that show up on your credit report, and I’ll come back to that, they’re almost always not going to approve you for a new card.

Now, I say that show up on your credit report because business credit cards don’t always show up on your credit report. Most of them don’t. A lot of other issuers have similar rules. Amex, it’s like you can’t apply… I can’t remember all of them. It’s like you can’t apply for the same card within 90 days, and if you go search card approval rules by bank, there’s a blog post that the Frequent Myler team wrote where it’s like a list of every single one of those rules.

Obviously, if you’re going to be applying for a card, make sure you don’t break those rules. Some issuers are like, “We’ll only approve one card within six days.” Well, then don’t apply for two cards back to back. It’s just not going to work. That one’s the most notorious. What that means is if you saw two great sign up bonuses, maybe apply for the one at the bank that cares less about those kind of rules second, and the one that cares about those rules first.

So if you’d opened four cards in the last 24 months and you’re really eyeing two cards with big welcome bonuses, get the Chase one first because you might not get approved for the Chase one second. I would say high level, Capital One is like if you’ve opened a lot of credit cards, they get skittish. Chase has more rules, they’re less skittish than that, and then Amex is probably the least skittish. And then obviously they’re not the only three issuers, but high level those are three of the biggest.

But sequencing what order you apply for a card in makes sense. And if you want to hit the game hard where you’re opening I guess more than five personal cards over 24 months, then that rule’s going to matter. But we talked about business cards, and I think one thing that’s important to clarify is I know a lot of people who think, “Well, I can’t have a business card, I don’t own a corporation.” And I will say there’s a wide definition of what a business is. If you have an Instagram account and maybe one day you might want to monetize that, well, every time you post, you’re laying the foundation for a future influencer business. You don’t need to go get your EIN from the IRS, though that is a very, very simple process. Like fill out a form online and get it immediately by email.

But if you have anything that could one day make money, that could be a business and you could do that business as a sole proprietor. I know a lot of people who are like, “Oh, well I’ve done a little consulting.” I’m like, “You have a business.” “Oh, sometimes I buy things and sell them on eBay.” Well, you have a business. I would imagine that almost every single person here listening is doing something in their life that would legitimately classify as a business, even if it doesn’t have revenue yet, even if it’s not filed with the state.

Tori Dunlap:

I teach piano lessons, all of these things. This is one thing actually, Chris, this is perfect to talk about, because I’ve been meaning to talk about this. I almost want, beg of people to just start a business, even if it’s not really a business, to get all of the additional perks of business owners. The write-offs, the points and miles, especially if you pool your business points and miles with your personal points and miles. There’s so many opportunities for you, to your point, to come up with what the business is and immediately start saving a shit-ton of money on the things that you’re already spending money on or thinking about on a day-to-day basis.

Chris Hutchins:

I can’t remember. I think it maybe is like the hobby rule or something, but the IRS doesn’t look too great at people who have a business that has a bunch of expenses and no income forever.

Tori Dunlap:

No, totally. Yes. There’s a massive asterisks on that. Thank you.

Chris Hutchins:

So I say if you don’t have any revenue, those write offs might not be as lucrative as you think, but again, you would be surprised at how many things might generate enough revenue that it’s a business. I buy a lot of gold at Costco. I sell that gold. I have a business, even though I might not think of it that way.

If anyone has a credit card, which I imagine most people do, and you log into your issuer and there’s all these deals like a card linked deal where it’s like, “Oh, if you spend $200 at Lowe’s, we’ll give you $50 off. If you go spend $50 at Chewy, we’ll give you $15 back.” Well, every time I see one of those I think, “Is there a way to make money?”

And so, this is a fun exercise with my daughter and we had this Lowe’s offer for $5 off $200, and I don’t need anything at Lowe’s right now. There’s nothing that I need at Lowe’s, but I use this app called Card Pointers and it added that offer to seven of my Amex cards. So we go to Lowe’s and then I look at the gift card rack at Lowe’s and I look for whichever gift card has the highest resale value, which was I think at the time it was Apple or Dick’s Sporting Goods. I think it was Dick’s Sporting Good. They were all sold out of Apple gift cards, that what I wanted.

And so, for $200 I buy a $200 Dick’s Sporting Goods gift card, which I could sell for like 89 cents on the dollar. So I lost 11%, but I was getting 50 of the $200 back, so I was getting 25% off. So I get 25% off and I can sell it for an 11% loss. I made 14%. So we went to the self checkout, $200 gift card, one Amex. $200 gift card, next Amex.

We’re just buying these gift cards, taking advantage of this offer, reselling the gift cards. And I think that day we made 200 bucks. Now, was it worth my time to go through this hassle, drive to Lowe’s, spend an hour buying these gift cards? You could argue no, but do you want to know how excited my five-year-old daughter was when I put $200 into her little bank account and we started talking about what she could do with $200, and that afternoon we went for ice cream and she’s like, “Can I buy mommy and daddy ice cream?” She bought me ice cream.

Tori Dunlap:

Yeah. Oh yeah.

Chris Hutchins:

So now that we have children, when I see these little plays if you will, where I’m like, it maybe isn’t worth my time, I’m like, but could I teach my daughter a lesson in this process? And I don’t know what that lesson’s worth, but it’s worth a whole lot more than the dollars we saved. So I don’t know, you can see I just could go down all these rabbit holes on this. You take this where we want to go, but I feel like every time I see a deal, it’s like how could I make money on this deal?

Tori Dunlap:

You and my father would be best friends. I don’t know if you know this about me. I started my first business when I was nine years old because my dad bought a candy vending machine, like a gumball machine and brought it home and said, “Do you want to start a business?” And I owned 15 of these vending machines by the time I graduated high school. And all the profits went to my college fund. And this was the thing that my dad and I would do once a month on a Saturday, is we would go out and we would service the machines.

And I didn’t invent anything. I didn’t go on Shark Tank, but I learned how to run a business. I learned how to manage money. I was writing checks as a ten-year-old. I was writing checks at Costco to be able to buy my chocolate-covered raisins to go in my vending machine. And I learned so much from that. And I also have so many memories with my dad. It wasn’t really about the money. We barely made any money. It was about spending quality time with my dad, learning something new. I 100% believe that a lot of the skills I learned throughout my childhood of running this business, I use every single day in running this business now. And so, those kinds of things, yeah, it might not be worth your time, but wow, it becomes an activity and an activity. I didn’t have to take her to the fair to spend a bunch of money or to a movie. We didn’t spend any money. We actually made money. I love that.

Chris Hutchins:

I love it. I’m looking at this can and one of the things we do is we take all the aluminum cans and we go recycle them for the cash.

Tori Dunlap:

Oh, same shit I did too. Absolutely.

Chris Hutchins:

I’m like, so if you live in California or Michigan or Maine, Vermont, Massachusetts, New York, Hawaii or Iowa, at least on this can, we just collect all the cans. We go cash them in. The place is grimy. And my daughter’s like, “I don’t really like this place.” I’m like, “But,” at the end somebody hands her like $4 and 85 cents and she’s like, “This is so cool. I made money.”

Tori Dunlap:

So that leads me to something that is really important. We talked about it briefly at the beginning, but in my head usually because I think when you get to the point where either you’re a busy person or a business owner or honestly, my mindset switched as I started to make more money, I realized, okay, there’s a certain cost benefit analysis that I need to do of can I be using my time to make more money than again, trying to find out all of these hacks.

So you had briefly talked about it, but I just want to return to when do we determine what’s worth it for us versus what isn’t? Because some of these are 100% worth it. I can spend two hours researching business class flights and get them for super cheap, amazing. Some of these other hacks, I’m not sure. So how do we determine that and how do we determine that for each of us as individuals specifically?

Chris Hutchins:

I’ll give you an answer and then a caution. So you could do it as simply as saying, “Okay, what is my hourly rate?” And that can be tough when you’re an entrepreneur, because the three hours that you spend thinking about your business could come up with an idea that makes you an unlimited amount of money or could be completely useless.

And so, I like to think of it not as an hourly rate, though maybe it’s backed into it, but I just set it more than trying to calculate my income divided by my hours. It’s like what is my threshold for when an amount of money moves the needle? And for me, I have one when I’m with my kids and one when I’m not, assuming that the thing is a teachable lesson. For 50 bucks, I might take my kids to do something to teach them, but if it’s during the 9:00 to 5:00 workday and they’re in school, I’m not going to do it.

So I would say everyone has to come up with that dollar amount. It’s going to be relative to how much you currently earn, how much you save, how much savings you have. If you’ve saved a ton of money, maybe you’re not interested in spending more time to save more. It’s going to be relative to what else you would do. If you don’t have a business idea, then that’s probably different than if you have an active business you’re running and you’re taking time away from it. I would not encourage anyone with an active business to be spending the weekend going to flip gift cards from Costco when they could be building a company if that’s their main thing. I try to think of a dollar amount and then I say, “Wait, wait, wait, pause. Is this thing going to cross that threshold? Is going to Costco to flip this gift card going to make me enough money that I want to do it?”

But I would encourage you to maybe choose the hours by which you do this, because for me, I’ve probably set that thing at hundreds of dollars an hour somewhere. But I don’t want to think about it on the nights and weekends, because the last thing I want to do is my daughter’s like, “Hey, do you want to play a game?” And I’m like, “Well, the game’s going to take an hour. I got to pay $400 to play a game with you? Sorry, kid.” So for me, when I have work hours, I try to value my time. When I’m not during work hours, I try not to value my time and I set a much higher bar.

And so, when I was talking about Costco gold, the bar for weekend time with the kids is like $1,000 an hour. And it just happened that last weekend. There was this, any trip to Costco, we’d make $1,000 and we were like, “Kids, we’re going to Costco again.” But if it was $300, I might do that during the work day when it’s just my time. But on the weekend I set a way higher bar, and I’m not really thinking. It’s more like opportunistic than trying to track every hour and value each one.

So I would say earlier in my career, it might’ve been $20. Went up to 100, maybe now as a few hundred. And during times when life is busy or family’s involved, it might cross 1,000. And so, you don’t need just one number. It can be relative to the situation and relative to your time. But I can’t overstate how important free time is when you’re running a company because you’re just so caught up in all the day-to-day that it’s always so hard to think, what should we do?

And so, for us, I really wanted to go to Iceland and we ended up starting a tours business where we found a guy that knows more than anyone in the world about Iceland. We did an episode about just Iceland and then we said, “Hey, we’re going to go on this trip. Does anyone want to come?” And we took a group of people to Iceland last year and now we’re taking two groups of people to Iceland this year. That didn’t just pop in my head until I was ruminating on Iceland and it came there. So leave time for that. It is valuable. It’s just hard to put a specific dollar amount on it.

Tori Dunlap:

Yeah. I just realized we didn’t talk about Costco. So let’s touch on Costco really quick and then I have one last question for you after Costco. Okay. So yeah, so the 4.99 rotisserie chickens, absolutely incredible. But the one that I found that literally everybody in my life knows I was trying to bully anybody and everybody into taking this on with me. They had a Costco travel deal. Did you see the Four Seasons Bora Bora situation at the beginning, I think of this year? Did you see this deal?

Chris Hutchins:

I was saying at the St. Regis Bora Bora on points and every couple we met we were like, “How did you decide to come here?” And they’re like, “Costco.”

Tori Dunlap:

Costco,

Chris Hutchins:

Costco.

Tori Dunlap:

So it was round trip economy from LA to Bora Bora. And as anybody who’s tried to get to Bora Bora knows that flights are so god-damn expensive. I think it was round trip flights and then it was like you get free breakfast, you get all of that. But it was four nights, I think at Four Seasons, Bora Bora, which normally costs like $2,500 and I think all in the whole trip was like 4,000, 5,000. It was so cheap and I didn’t end up pulling the trigger, but everybody heard about it. It was so good.

Chris Hutchins:

I don’t know when this will come out, but right now for whatever reason, Hilton has a ton of open inventory at the Conrad Bora Bora for 120 to 140,000 points a night, which again, Hilton points go on sale all the time. We’ve been to the Conrad Bora Bora twice. Economy flights ever since French B, which is like a discount French carrier came. Economy flights have gotten very cheap. So from San Francisco I’ve seen Bora Bora for like 6, 700 bucks round trip.

So if you have Hilton points, if you want to buy Hilton points, a trip to Bora Bora can be in your future. I don’t know why Bora Bora doesn’t get as much love as the Maldives, because if you live on the coast, it’s like an eight hour flight. It’s not that farther than Miami and New York and you went on this trip. It’s amazing. If you are an active person that wants to have a thousand places to drive and do, it’s not a trip for you. If you’re someone who wants to just relax at a hotel and have everything catered to you, it’s fantastic.

And if you open up one of those Amex Hilton cards or at least the Aspire card, you get diamond status on Hilton. So at least when we went, free breakfast, which these breakfast buffets are just unbelievable. I actually did an episode that I filmed from the Conrad Bora Bora talking explicitly about how the price mechanics of that deal. It was a little windy, the audio quality isn’t as good as others, but Bora Bora on points specifically looking at it today in June 2025, I was blown away at the availability to go during the summer, which we’ve been in the summer, is a great time. It’s a little warm, but not like Desert Valley warm. It was great. So I would encourage anyone with Hilton points or a desire to buy them, to check out the Conrad and Bora Bora. Highly recommend. Or check out the Costco travel deals.

Tori Dunlap:

Yeah. Guys, I have I think seven tabs open just from you and I talking again. You think I’m good? Chris is next level. Okay. My last question for you, your show, All the Hacks, which is literally going to be my next 12 hours of listening. You talk generally about upgrading your life or optimizing. So what are some of the best non-money related hacks that changed your life for the better? I’m thinking especially about that episode you did on sleep.

Chris Hutchins:

Yes. I mean sleep, it’s so funny that in our world, especially with the people on Instagram, everyone’s like, “Do you use an infrared or do you use a dry heat sauna?” It’s like you can optimize so many things in your health. If you’re not dialing in your sleep, I would say on the order of important things, it’s like sleep, exercise and nutrition. All the other little tiny things you can do to tweak your health don’t really matter. I always laugh when I see someone ask me, because we have a sauna and I love the sauna. And they’re like, “Do you think I should get a sauna?” And I’m like, “How often do you exercise?” For longevity purposes, they’re like, “I want to live longer. Saunas are known to do that. Should I get a sauna?”

I’m like, “How often do you work out?” They’re not really working out right now. I’m like, “You know what’s going to move the needle on longevity a lot more than a sauna? Exercise.” So I think that definitely sleep is important. Definitely nutrition is important. Definitely exercise is important. All those things. Some fun health things that I love. This is a very simple hack.

I am really bad when it comes to saying no to eating unhealthy food. You put a plate of cookies in my house, I will eat a lot more cookies than a normal person. So what I’ve started doing is I don’t try to say no, don’t say no to the cookie. Say no to the cookie for five minutes, give yourself permission to have the cookie, just in five minutes. And for my brain and the way my psychology works, it is so much easier than saying no. But in those five minutes, I get distracted and all of a sudden I’m onto some other thing and I forgot about the cookie, and then maybe I come up to the kitchen an hour later, I let myself eat a cookie and then I say five more minutes till the next one.

But old me would’ve eaten 13 cookies before I even left the kitchen. And so, that is a very simple thing that has actually changed how much unhealthy food I consume in my own house. I also think that if I’m going out to restaurant, I sometimes look at the menu in advance, usually right after lunch, and I just decide what I’m going to order for dinner, because I make a much better decision when I’m not hungry at home than when I’m sitting at the restaurant. And if I go to the restaurant, I’m like, “That burger looks good.” If I’m at home, I’m like, “I don’t know, that salad looks good.” And so, I just pre-commit to what I’m going to order. It’s not like I’m calling the restaurant saying, “When Chris shows up tonight, do not let him order anything.” It’s like little mental ways to change my perspective in my mind and it helps so much.

Tori Dunlap:

Yeah. I’ll share two with you that you may have talked about on the show.

Chris Hutchins:

I love it.

Tori Dunlap:

One blew my mind a couple months ago and it’s so fucking simple. If you want eight hours of sleep, you need to be in bed for nine hours. It’s so easy. But all of us are like, “Okay, we’re doing the math of like, okay, if I wake up at seven, I got to go to bed at 11, blah blah.” And it’s like, no, you’re going to take 20 minutes to fall asleep. You’re going to have to get up and use the bathroom. You’re going to toss and turn a little bit. You will not get eight hours of sleep, so you need to spend nine hours in bed. And that single handed, I was just like, okay, I need to stop doing the mental calculations for eight hours and I need to do the mental calculations for nine, and I need to get my in bed with nine hours to spare. So that’s the first one that was so simple.

The second is I have a history of diabetes in my family and the order in which you eat your food matters so much. Do you know about this, Chris?

Chris Hutchins:

So much. I am guessing you’ve worn a continuous glucose monitor to even [inaudible 01:16:28]

Tori Dunlap:

I’m not quite that crazy yet. No, I listen. Glucose Goddess is the one I listen to. Do you know this woman?

Chris Hutchins:

I know, but I have not do not know.

Tori Dunlap:

Basically it’s like the order in which you eat your food matters so much for our blood sugar and our energy. And even if you are not diabetic. It’s like basically you don’t want to put carbs in first, and you definitely don’t want to have a sweet breakfast,

Chris Hutchins:

Protein first.

Tori Dunlap:

Protein first with fiber. bread often is the first thing that comes out. And same thing with your cookie example. I am never going to turn down bread, but the bread sits on my plate until the salad comes out. Then I eat the salad and then I eat the bread. So I eat the salad first and then I eat the bread. Just even that has changed my energy level so much. Same thing, I don’t drink a lot of coffee. I had a coffee this morning. I know if I drink that coffee on an empty stomach, I am going to be a fucking crazy person all day. I wait, the coffee sits there. I do not even take a sip. I eat the food and then I get to have a sip. But it’s not deprivation, it’s just doing things in a different order and it’s single-handedly changed so much of my life.

Chris Hutchins:

You have more self-control. My version would be to tell the waiter or the waitress, I’d be like, “Could you just bring the bread later?” I see it on other tables.

Tori Dunlap:

Yeah, I mean, sometimes it doesn’t happen. I will be 100% honest if I’m ravenous, sorry, I’m eating that bread. But in general, I try to say, okay, I’m at least going to have two bites of salad, three bites of salad. Because the way she describes it, and I think most dieticians and nutritionists describe it the same way, as it’s like your body is a sink, and what you’re shoving down the sink first is the thing that sits there. So you need to think about, okay, I’m going to put veggies and I’m going to wait to put the fats or the sweets until the rest of it. So that’s been super helpful for me.

Chris Hutchins:

Totally. Now, I would say I’ve done a lot of health testing and to anyone that’s interested now, I believe you can get continuous glucose monitors over the counter.

Tori Dunlap:

You can. You can.

Chris Hutchins:

And it’s wild because I wore one for a week and there are a few things that people say are like for some people if you put cinnamon with your carbs, the spike is lower.

Tori Dunlap:

Oh, apple cider vinegar is the one I’ve heard. Apple cider vinegar. Yeah.

Chris Hutchins:

I’m not even kidding. Would just, my wife and I had some fun experiments. We were like, what happens if we eat 30 Swedish fish? And it’s like your blood glucose is literally so high off the charts, it’s insane. But when I would eat cinnamon rolls versus bread, the cinnamon rolls did not spike me as much as bread because I guess my body, cinnamon. But when you actually see the data working, you’re like, oh wow, eating my protein before I eat my carbs. You can see that it has an impact and you can try different foods all week.

And I would encourage you, the first time I did this, I did not do it. Write things down, because it’s so interesting in the moment. And then three months later you’re like, wait, what was the thing that spiked my blood glucose I totally forgot? Or even just take photos and then you could figure it out later. At this point, you could probably export your data, take a photo of every meal. The photo has a timestamp in the data, put it all in, ChatGPT and say, “Here’s all the food I ate this month. Here’s my data. Just tell me what I should and shouldn’t eat.

Tori Dunlap:

Probably.

Chris Hutchins:

If you’re not leveraging AI for almost everything you’re doing, it’s like having an army of interns for free. And that’s just one great hack. But it was so fascinating to see the data that comes off of a glucose monitor. Then I was like, now I’m changing this thing. And it wasn’t just because someone told me, it’s because I actually saw it work in my body.

Tori Dunlap:

Yeah, Chris, you should follow Glucose Goddess, because she literally does charts of cookie, cookie with milk. Toast, toast with avocado. I love it. And you can see the different spikes. It would just tickle your brain. Okay, I could talk to you for hours. We have to wrap up. Chris, tell me everything about the podcast and newsletter. Where can people find more about you?

Chris Hutchins:

Everything’s at allthehacks.com or chrishutchins.com. They’re the same place. You can search my name. If you’re listening to a podcast, just search for it. I would say similar to what we were just talking about, I try not to focus on just points and miles. I feel like if you had a podcast that was all about that, a lot of people like me and you, we might just be like, “It’s too much.” So we actually just did an episode on gut health. I’m looking at this board. We’ve done an episode on happiness, medical tourism.

I like to dive into upgrading your life, your money and your travel. There’s a special place in my heart for points and miles, but my goal is every episode, no fluff. Let’s just get to the tactics, let’s get to the playbooks and let’s figure out how to dial one area of your life in. And I hope that every single time, someone leaves with one thing that will change their life and make them happier, make them healthier, make them feel better, and that is the goal. And so, it might be a lot. I’m not just sitting there shooting the shit. It’s like I want you to learn and then get back to your busy life. And so, you can find it wherever you listen to podcasts. I’m always open to people reaching out. You can contact us on the website, links to everything are there. Yeah, that’s where I am.

Tori Dunlap:

Amazing. Chris, thank you. This was so valuable.

Chris Hutchins:

Thank you so much. This is a lot of fun.

Tori Dunlap:

Thank you so much to Chris for joining us. All the Hacks is available wherever you’re listening right now. I know I subscribed immediately after interviewing him for this conversation, and it’s such a great show, especially if you love Financial Feminist.

Thank you for being here. Thank you for listening. This is a great episode. To share with loved ones, with your partner, with your family, especially if you’re trying to save extra money right now or trying to get creative with ways to save money that you may not have heard or seen elsewhere. We appreciate you sharing the show. We appreciate you supporting feminist media. We’ll talk to you soon. Bye.

Thank you for listening to Financial Feminist a Her First 100K podcast. For more information about Financial Feminist, Her First 100K, our guests and episode show notes, visit financialfeministpodcast.com. If you’re confused about your personal finances and you’re wondering where to start, go to herfirst100k.com/quiz for a free personalized money plan.

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.

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