Hello there, my friend.

I’ve spent years telling anyone who’ll listen that 80%+ of people who ask for a lower interest rate on their credit card get one, but far too few people ask. I can’t tell you how many times I’ve said this on a podcast or some other interview and gotten the same stunned reaction:

WHAT? Why doesn’t anybody know this?

Knowing is only a part of the problem, though. Maybe the most frustrating part of all of this is when people know they can ask but they still don’t.

The question that explains a lot

While I was researching my book, I asked financial therapist Amanda Clayman about this, and she answered with a question of her own: “Are you from an asker culture or a guesser culture?”

In a guesser culture, Clayman said, you’re taught that putting someone in a position where they might have to say no is rude. So instead of asking directly for what you need, you hint. You say, “Gosh, I’m starving,” and wait for someone to offer you food, rather than just asking for a sandwich. The whole point is protecting the other person from an awkward moment, even if it means you don’t get what you want.

In an asker culture, none of that applies, Clayman said. You just say what you need. If the answer is no, fine. You asked, you move on. Nobody’s feelings are hanging in the balance.

Clayman is from the Midwest, which she described as a classic guesser culture. She married a New Yorker, and living with him rewired how she saw her own family.

“I constantly felt like, ‘Oh, my God, he’s saying all the quiet parts out loud,’” Clayman told me. Now he’s the one who calls customer service in their house because he can push through a phone tree and negotiate without the discomfort that would send her, in her words, “to bed like a Victorian woman.”

Companies know we’re guessers, and they like it that way

Most of us are guessers, Clayman said. However, while many of us don’t recognize it, many businesses do, and they use it to their advantage.

“It’s not an accident that people don’t do it,” she said. “That’s a feature, not a bug.”

Companies do not build systems that make it easy for you to ask for a better rate, a fee waiver or a discount, Clayman said. She said they build systems designed for askers, because askers are rare and expensive to accommodate, and guessers just quietly keep paying full price. The awkwardness you feel before you call your cable company isn’t a personal failing, she said. It’s working exactly as designed.

So what should guessers do?

If you’re a guesser, Clayman said you don’t have to rewire your whole personality. You just need to be able to act like an asker for five minutes at a time a few times a year.

Pick your battles wisely. You don’t have to negotiate everything. Pick three or four items to focus on — your credit card APR, cellphone bill, gym membership and a medical bill, for example — and then spread them out over the course of the year. They don’t all have to be big wins, either. Getting a small, easy victory to start with can be incredibly motivating, and that really matters.

Write down exactly what you want to say, and read it out loud before you call. Most of us stink without a script. That’s why every request I address in my book comes with a word-for-word script to help you know what to say. It makes a real difference. (And why I offer all new subscribers three free scripts when they sign up.) You don’t have to write a novel, nor do you have to anticipate every possible twist in the conversation, but just starting with a scripted sentence or two can really help. And once you’ve written it down, read it out loud. Sometimes what looks good on a page doesn’t sound as good when spoken.

If you have no idea what to say, start here:

“I reviewed my account and noticed I’m paying more than I expected. Who on your team can I speak with to see if there’s a way to lower my bill?”

It won’t apply to every negotiation, but it works in many cases. Plus, with a few small tweaks, it could work in plenty more.

Give yourself permission to feel weird about it. Your hands may get clammy, and your heart might race. These aren’t signs that something’s wrong. It’s just your body reacting to something unfamiliar. It happens whether the call goes well or badly. Feeling it isn’t the problem. Letting it stop you is.

Your homework for this week

Try it on one bill this week. Maybe it is the one that has bugged you the longest. Maybe it is the one that you think will be easiest to ask for. Maybe it is the biggest bill. It doesn’t matter.

Make the call. Let your hands be clammy the whole time if they need to be.

Then, once you’ve done it, come back and tell us about it in the comments.

Next week… I’m off to NYC

I love my New York media tours, and I’m back at it next week. Going to be a very busy one, but it’ll be a lot of fun. I’ll share pictures here soon.

Also, if you have any good restaurant recommendations for me, let me know. Ideally, they’d be places that aren’t so expensive that I get in trouble when I file my expense report.

Until next time!
Matt

Hi, my friend.

My friends Alison and Scott were staying at a resort in the Maldives, in one of those overwater huts like the one in the above picture. They hadn’t paid a dime for the room. They’d cobbled together every point they had between two credit cards just to cover it.

Early in their visit, they ended up making small talk with the property manager a few times. There was nothing strategic about it. Alison and Scott are just both social people, and they genuinely liked the guy, so they told him so.

Later in the trip, the manager showed up at their door and said he had bad news.

“He said, ‘I have bad news, I have to move you.’ And we’re like, ‘Oh, but we love this room.’ He goes, ‘Just trust me,’” Alison told me. “He said, ‘I double booked. We’re short on the type of rooms you have. These other people are giving me a really hard time. They’re being assholes, and you and your husband are really nice. So go enjoy three nights in the presidential suite on us. Thanks for being cool.’”

That’s the whole story.

The presidential suite. Four bedrooms. On the water. The kind of room that normally runs somewhere north of $10,000 a night. They didn’t ask for an upgrade. They didn’t complain their way into it. They just weren’t a pain to deal with, and when the hotel needed someone to offer its best inventory to, that mattered more than what they’d paid to be there.

Alison told me this in an interview I did with her for my book, back when I was gathering stories about the everyday power of just asking. While much of what we cover here is relatively small stuff — a $30 waived late fee here, a $45 food voucher there —this one is anything but.

It is also proof that sometimes you don’t even have to ask directly to get a break. Sometimes it is just about not being a jerk.

The pattern held in London too

It wasn’t a one-off either. A few months later she was in London with her mom for a milestone birthday, checking into a hotel that runs well north of a thousand dollars a night for its basic rooms. They’d booked the cheapest room available.

When they arrived, they mentioned at check-in that they were there celebrating her mom’s big day. The person at the desk told them their room wasn’t ready yet. When it was ready, they got a very big surprise.

“I just said, ‘We’re here for my mother’s 70th birthday, and she’s never been to London,’” she said. “We were sure to mention it was a special occasion, and when they came back to get us for the room, they upgraded us to a suite.”

This type of success isn’t super-common. Hotels aren’t just handing out suite upgrades to everyone who says they’re celebrating a birthday. However, the bigger lesson here is clear… It is almost always worth mentioning these sorts of things when you check in to a hotel or go to a restaurant.

You may just get a congratulations or a happy birthday greeting. Other times, however, you might get a free slice of cheesecake or $10 off an entree. Or one time you might even get a free upgrade to a $1,000 suite.

Either way, you won’t know if you don’t say anything.

The playbook

Obviously, these are two very high-end examples, but the truth is that your approach should be largely the same whether you’re staying at a five-star luxury resort or at a run-of-the-mill chain hotel off the interstate.

Here’s what Alison and Scott actually do every time they travel:

• They dress as if they belong there. You don’t have to dress like you’re off to the Met Gala, but you probably shouldn’t look like you just rolled out of bed either.

• If there’s an occasion, they mention it. They don’t mention it as a bid for a freebie, just as a fact. Whether you’re celebrating an anniversary, a birthday, a first trip somewhere or something else special, people who work in hospitality generally like being part of that moment. Plus, hotels know that if they treat you really well in an important moment, you’re a whole lot more likely to return.

• When they want more than what they booked, they ask for it the easy way. They ask something like, “Any upgrades or extra perks available?” They’re not being pushy or obnoxious. They’re not acting entitled or haughty. They’re just asking nicely and politely to see what happens. And if they’re told no, they let go. There will be other days.

“They’re not gonna upgrade the jerk“

Niceness can unlock doors.

It sounds ridiculously simple. It may even sound a little outdated in a time when so many people are focused more on being an “alpha” than on being kind. However, it is true.

This certainly doesn’t mean niceness is a foolproof cheat code for getting free suite upgrades. Nor does it mean that there isn’t a time to be tough and stand up for yourself. Rather, it means that when a hotel does have something extra to give away, and they often do, they’re going to give it to the guest who was easy to deal with over the guest who made their day harder.

Alison said it best:

“If they’re gonna upgrade someone, they’re not gonna upgrade the jerk. They’re gonna upgrade the nice person 9 times out of 10.”

That’s worth remembering the next time you’re standing at a check-in desk deciding how much attitude to bring with you.

Ever gotten a great upgrade?

I love this story my friend Christine Burke shared about using her late father’s technique for getting upgrades. It’s such a simple and kinda goofy thing, but it certainly has worked for her, and it can probably do the same for you.

Got a great upgrade story? Share it in the comments below!

In other news… We’ve got a Dynamite weekend ahead!

This weekend, we’re taking my almost-80-year-old mom to see BTS — her favorite musical artist — for the first time. She’s going to absolutely go crazy.

It’ll be my first time seeing them as well. In fact, among my wife, son, sister and mom, I’m the only one who has never been to any K-Pop show before. I’m fascinated to see what it’ll be like.

But honestly, this is about my mom finally being able to see in person the group that has meant so much to her and helped her move forward after my dad passed away six years ago.

I wrote about it in the story below. If you’ve been an Ask, Save, Earn subscriber for a while, you might’ve read the story, but I always love sharing it.

Until next time!
Matt

I generally don’t consider myself old-fashioned, and I don’t think those who know me well would describe me that way either.

However, there is at least one thing that I believe in strongly that is decidedly old-school.

It is one of the most powerful financial tools you have access to, and most people don’t use it nearly enough.

I’m talking about a phone call.

We love our phones, but hate making calls

Yeah, I know. You probably rolled your eyes or let out a heavy sigh reading that last sentence.

Ooooookkkkkaaaayyyy, grandpa. Thanks for that.

We’re perpetually attached to our phones, but we hate making phone calls, and I totally get it. Assuming that you can even find a number to call, which can seem impossible today and is likely to only get harder in the future, it feels like you’re as likely to find yourself in a never-ending loop of a phone tree as you are to actually get a living, breathing person on the other end of the line. Then, if you do get to speak with someone, it can be hard to know what to say, especially when you’re exasperated after sitting on hold for the better part of an hour. It can all just add up to a real mess that people don’t want to deal with.

Plus, chatbots, social-media-based support, apps and other tools can be incredibly efficient and effective in solving problems. There are absolutely times during which you’d be foolish not to use them today.

Still, in many cases, a phone call can give you an advantage that none of these can: a real, person-to-person connection that few other communication tools can match.

That matters, especially when money is at stake.

“There’s nothing quite like hearing someone’s voice”

To be clear, I’m not saying that people can’t make meaningful connections with text, chat and other tools where you don’t hear someone’s voice or see their face in real-time. I’m a writer. Believe me, I get the power of the written word. I’m also the father of a college-aged kid, so I know that text communications can be amazing and meaningful, too.

But there’s nothing quite like hearing someone’s voice.

I wrote about it in the prologue of “Ask Questions, Save Money, Make More: How To Take Control Of Your Financial Life”:

It seems downright old-fashioned, but this book preaches the power of phone calls. Hearing another voice can bind people together in ways that text-based communication can’t. Your voice makes you more real. It humanizes you, which means that it can make it harder for someone to tell you, “No.” It’s one thing to type that word onto a screen but something else entirely to say it to someone whose voice is trembling with nerves, with kids playing and a dog barking in the background. Social media proves this truth every day. Millions of people around the world post cruel, hurtful comments about others that never in a million years would they say over the phone.

But phone calls don’t always feel easy. It can seem almost impossible to get to a real person on the other end of the line. Once a human is listening, the conversation can involve a greater level of vulnerability than a text message or online chat does. That’s why most people tend to shy away from them. But again, nerves are normal. You can work through them, and once you do, you can use the power of phone calls to your advantage.

Put a face with that voice and the connection can deepen. Of course, I’m not saying you need to FaceTime with your credit card issuer’s customer service representative. However, in certain situations, such as negotiating down a rent increase or trying to get your gym to waive an initiation fee, making your case face-to-smiling-face might make it more likely to get your way.

As always, there are no guarantees that this will help, but if you think it will make you less likely to hear a “no,” what do you have to lose?

Making the call a little easier

Negotiating with someone can be challenging regardless of the medium. Here are a few tips that might make it a little easier for you:

Write out a script. Most of us aren’t the best at thinking on the fly, especially when there’s money on the line, so taking the time to think through what you want to say is crucial. Don’t stress too much. You’re not going to think of everything, but even just putting some thoughts down on paper to get started can matter. I’m a firm believer in the power of the script. That’s why there are word-for-word scripts included with every chapter of my book, and why I offer three ready-to-use scripts to new subscribers to Ask, Save, Earn.

Subscribe now

Practice before you call. As silly as it may seem, having a friend or relative role-play the conversation can be really helpful. I’d suggest running through it three times or more — one that goes perfectly smoothly, another where your partner pushes back a bit, and a third where they really let you have it. Chances are the real conversation won’t go quite like any of your dry runs. Plus, you’ll likely end up wanting to rewrite your script afterwards, but just having the experience will probably make you feel more at ease.

Skip the phone. Talk in person instead. Sure, this isn’t always going to be possible, but if it is, and you are someone who feels more comfortable chatting in person than over the phone, consider that option. I’m thinking about a medical provider, a bank with a brick-and-mortar option near you, a gym or a contractor, for example.

Breathe. We have to give ourselves permission to suck at things in order to improve. I’m not saying that you’ll be terrible the first time you try to negotiate over the phone, but I am saying that it is totally OK if you are. Everyone you can think of who is amazing at something wasn’t when they started.

Until next time!
Matt

Hello there, my friend.

I can’t even tell you how much I love it when readers reach out to tell me how they saved themselves money or made some money just by asking.

That happens more often these days, and I hope it only becomes more frequent as the Ask, Save, Earn community grows.

The latest example came from Christine, a coordinator at a large entertainment company in Los Angeles. Longtime Ask, Save, Earn readers might recognize her from this story from September 2025.

Saving that much money just by asking a few questions makes Christine nothing short of a superstar around these parts, so I was excited when she reached out again to share her latest success.

Here’s what she sent me…

“I had to pop in for some quick dental work, and when I received the original quote, I asked if the office had any promotions, specials, potential discounts I could be considered for, and they responded by knocking my out-of-pocket cost down by over 50%! A 5-minute email chain saved a few hundred dollars!”

When I read that, I reached back out in a hurry to ask if she’d be willing to share the email she sent so people could learn from it. She was nice enough to say yes.

Note: To protect Christine’s privacy, I removed names and other details that weren’t really pertinent to this discussion. They’re replaced by “xxxx” in the text below.

The email

Thanks so much, xxxx! I really appreciate you sending this over.

One thing - I recall the office offering some specials/discounts earlier this year. Might there be any current promotions, discounts, or other options available that could help lower my out-of-pocket cost?

Thank you again for all of your help!

Best,
xxxx

Simple, right?

She expresses gratitude, gets to the point quickly but without being pushy, and then thanks the person again.

The dentist office’s response

Hi xxxx!

Great question! Since your insurance will pay our usual and customary rate, I can pass any savings on to your out-of-pocket cost.

I can offer an additional discount for the xxxx if you decide to move forward with all of Dr. xxxx’s recommendations, bringing your out-of-pocket cost down to $180 for the xxxx. That, in addition to the xxxx for $100, would bring your total to $280.

Let me know if this works well for your budget!

Smiles,

xxxx

That’s it! There was one string attached — she had to move forward with all of the doctor’s recommendations — but Christine agreed to do so. As a result, she knocked the original quoted out-of-pocket cost of $570 down to just $280. That’s a savings of $290 or slightly more than half of the original bill.

I’d say that was worth her time.

More success stories

Christine is a rock star when it comes to these requests, no question, but much of her success comes from simply being willing to ask. Nothing she did at the dentist office — or when she saved $3,500 as described in the previous post — was anything that most anyone else could not do. But you have to do them.

Of course, there’s never any guarantee that you’ll even save a penny when you ask these questions, but you’ll never know if you don’t try. Plus, even if you strike out most of the time, you still come out ahead. And who couldn’t benefit from that right now?

Here are a couple more posts about reader success stories …

Here’s one of my own. Like Christine’s story, a simple email made a major difference for me …

And there are plenty more to be found in my book, “Ask Questions, Save Money, Make More: How To Take Control Of Your Financial Life,” which includes word-for-word scripts for how to make these requests.

Share your success story!

I’d love nothing more than to add your success story to the list above. If you have one — or know someone who does — and would like to share, just reply to this email or leave me a message in the comments.

In other news… The Fed did nothing, and it was something!

I have a weird job sometimes, like yesterday.

Yesterday, the Federal Reserve — which affects, to varying degrees, the interest rates people pay for everything from mortgages and auto loans to credit cards and personal loans — announced that they weren’t going to raise or lower interest rates.

When most entities do nothing, it generally isn’t news, especially if you know with a high degree of certainty that it is going to do nothing. However, the Fed is not most entities. Whether it raises rates, lowers them or just leaves them alone, as they did yesterday, it makes major headlines.

That means I had to talk about what all this nothing meant.

The truth, however, is that all this nothing really does mean something. It is great news for savers because CDs and high-yield savings accounts will continue to offer really strong returns. However, it is a total bummer for people struggling with credit card debt or who are in the market for an auto loan or personal loan. (It impacts mortgage rates, too, but less directly than some other loans.)

I spoke about all of this with the New York Times, CNBC, Marketwatch and others. Click on any of these links to learn more about why it all matters so much.

Until next time!
Matt

Hi there, my friend.

I’m taking the day off from work today, but not to do anything fun, unfortunately.

Nope, I’m going to spend the day taking an online defensive driving course.

Don’t act like you’re not jealous.

Yeah, I was driving home after moving my son out of his college dorm room and got pulled over for going a little faster than I should have. Nothing crazy or outrageous, but just fast enough to catch the police’s attention on an open stretch of Texas highway.

Now I get to spend six hours online taking a course to learn how to be a safer driver. I’m definitely not looking forward to it, but it beats the heck out of having my car insurance increase. My family’s premiums are already steep enough, given that we have a college-aged driver. The last thing we need is something else to push them higher.

Cars are a hot topic these days

I’ve been talking a lot about cars lately, and not just because of defensive driving. LendingTree recently released a report revealing that 10% of Americans with an auto loan have a $1,000 monthly payment on one of those loans.

One thousand dollars a month for a car payment!!

Per LendingTree, that $1,000 equals 14% of Americans’ median monthly household incomes. And that’s just for the loan payment. That doesn’t include insurance, gas (which has been a little pricey lately, as you might have noticed), regular maintenance or any other costs associated with owning a car.

In my home state of Texas, where people love their big ol’ trucks, cars and SUVs, 15% of all auto loans have monthly payments of $1,000 or more.

I get that everyone has their thing that they love to spend money on and that vehicles are that thing for many, many Americans. I also hate to yuck other people’s yum, but, man, locking yourself into a $1,000 monthly payment on a vehicle for years just feels like a recipe for disaster.

My wife and I tend to pay cash for our vehicles. We’re able to do that, in large part, because we’ve never owned a car for less than a decade since we graduated from college, we tend to buy less car than we can afford and we consistently put savings into a car fund so when we do end up needing (or just wanting) a new car, we have substantial savings built up to pay for it.

Of course, with most financial questions, there’s no one-size-fits-all perfect answer, and this is certainly one of those cases. For some people, that giant monthly payment is perfectly manageable. If you have a high income, save consistently for retirement, have a substantial emergency fund, are not carrying high-interest debt, and are genuinely passionate about cars, that payment may fit just fine into your financial life. Also, if you’re a realtor or a salesperson or work in some other role where a really nice car can enhance your brand or your business prospects, it can make sense, too.

The problem is when that payment starts crowding out the things that matter more.

The question to ask yourself about your monthly car payment

If writing that check every month means you’re putting off retirement savings, carrying a credit card balance, skipping your emergency fund, or constantly feeling like you’re one unexpected expense away from trouble, the issue isn’t really the car payment. It’s the tradeoffs the payment is forcing you to make.

That’s why I think focusing on the dollar amount alone misses the point. A $1,000 payment can be perfectly reasonable for one household and a financial disaster for another. The more useful question isn’t, “How much is the payment?” It is instead “What will I have to give up to make it?”

If the answer is “not much,” you’re probably fine. If the answer is “my financial flexibility, my savings goals, and my peace of mind,” it’s a sign that the vehicle just isn’t right for you, no matter how sexy it may look in the driveway.

In case you missed them…

I’m not a car guy, but they’re one of the biggest purchases we ever make, so we talk about them from time to time here at Ask, Save, Earn.

Here’s a post with some wisdom from the savviest car expert I know…

And here are a couple about managing high gas prices…

I wish I could be confident that the affordability crisis around cars and gas would end soon, but the truth is there’s very little reason to believe it will, at least in the short term. That’s why it is important not only to be a smart, informed shopper when you’re looking for a vehicle to buy but also a diligent owner once you’ve taken the vehicle home. Taking good care of the car, including keeping up with your regular recommended maintenance, can make it last longer and allow you to keep it well after it is already paid for.

That should really be the goal. After all, the longer you can go without having to make a car payment, the better.

By the way, it is the same thing with defensive driving. The longer you can avoid having to take it, the better. Trust me on this one.

Until next time!

Matt

Putting my book out into the world has taught me a lot, but perhaps my favorite part has been hearing what readers actually do with it. After all, advice can sound smart in print, but it is something else entirely once someone is on the phone trying it out, when the stakes are real.

I recently talked with one reader named Sara about how she has put what she learned to use, and I wanted to share some of what she told me because it seemed so relatable.

Yes, asking works a lot of the time, maybe even more than you’d expect. However, it doesn’t work every time. Sara’s experience wasn’t a straight line of wins. It was hesitation, trial and error, a couple of real successes, and one case where she did everything right and her attempt at negotiation still fell frustratingly short.

Changing her perspective

Sara works in a role where negotiating on behalf of others is part of the job. She’s comfortable advocating in her job when it is expected and clearly defined. When it comes to advocating for herself, though, it hasn’t always been that simple.

She described herself as a bit of a people pleaser, the kind of person who might hold back rather than risk being seen as “the squeaky wheel.” That instinct is common — I know I can certainly relate to it — and it’s one of the biggest reasons people don’t take advantage of opportunities to save money.

It’s not usually a knowledge problem. It’s a willingness-to-ask problem.

After reading my book, that started to shift. She began to see asking differently. Instead of viewing it as a confrontation, she reframed it as a curiosity. It became more about exploring what was going on and, in some cases, correcting something that might not actually be right.

That change in perspective led to a bigger epiphany:

“I realized how fallible and subjective many different things that I took as objective can be, including price.”

Before that, she approached bills the way most of us do. You get a number, assume someone has a good reason for charging that price, and move on. Afterward, that assumption started to break down.

Putting the new mindset into practice

Once that mindset shifts, the next step is trying it out. That can be a little messy, as Sara discovered.

One of the first times she put it into practice, she was dealing with a set of car repairs. When the shop called with the estimate, she asked if there was any flexibility in the pricing. The answer was a quick no. She didn’t follow up, and that was the end of it.

Looking back, she realized the issue was how she asked. Her approach had been too open-ended.

She said, “I just posed the question, ‘Can we do any better?’ and they were like, ‘No.’”

If she were to do it again, she said she’d get more specific with her request. She’d come prepared with a clearer sense of what the parts should cost and where there might be room to adjust.

That distinction matters. Asking if something can be done often leads to a yes-or-no answer. Suggesting what should be done creates space for a conversation.

Not long after that, she ran into a situation where things played out very differently.

She needed an MRI, and when she arrived for the appointment, the price didn’t look right. In the past, that might have been enough to sign and move on. This time, she paused and asked questions, then called her insurance company on the spot and put them on the phone with the receptionist.

“I actually just called my insurance right then and put them on the phone with the receptionist,” she said. “Having them liaise together did bring down the cost.”

Her decision to get the two sides to talk directly led to a correction and savings of about $300. That’s a big deal.

It all happened because she didn’t assume the number on that bill was final.

Of course, it doesn’t always work out that way.

It is about trusting the process, not about perfection

She also shared a medical billing reimbursement issue where she had done everything right. She had records of whom she spoke to, when the conversations happened, and what she had been told about her insurance’s reimbursement policies. She made a decision based on the information she had been given. Unfortunately, however, what she had been told was inaccurate.

As a result, she got a higher bill than she expected, prompting her to make a series of calls in hopes of reducing what she owed. Ultimately, she was only partly successful. She got a slightly higher reimbursement, but well below what she was aiming for.

That’s frustrating, but it’s part of the process. You’re not going to win every time. It’s about avoiding the default outcome of never asking and always paying what’s presented.

What changed most over time wasn’t just the outcomes, but the approach.

It started with building the habit of asking, getting comfortable raising the question even when it felt a little awkward. From there, she became more precise, doing more homework in advance and making clearer, more targeted requests.

She also started keeping better records, noting names, dates and what was said. That kind of documentation can be surprisingly useful, especially when you need to follow up or push back later.

And she became more intentional in how she approached conversations. Instead of treating them like a confrontation, she focused on creating a sense that she and the other person were working toward the same goal. That shift tends to make interactions more productive and a lot less stressful.

None of this required a personality overhaul. She didn’t have to become more aggressive or more confrontational. She simply started questioning assumptions, asking more often, and refining her approach over time.

That’s where the real advantage comes from.

A few things to keep in mind

• Treat prices as starting points, not fixed outcomes. If there’s a number attached to something, there’s often room to question it. Doesn’t mean you’ll always get your way, but it usually can’t hurt to ask.

• Don’t worry about getting it perfect right away. Building the habit of asking matters more than how polished the first attempt is. Get your reps in, including role-playing. It may seem kind of goofy, but it can help. Eventually, you’ll get to feel more comfortable and confident.

• Be specific when you can. A clear, informed request tends to go further than a vague one. Doing some legwork in advance can make a real difference in helping you frame the conversation. For example, if you can find an offer from a competitor, you can start the conversation there.

• Keep track of your conversations. Names, dates, and notes can give you leverage if you need it later. You don’t need to write down every single word everyone says, but keeping some notes of some key details can help immensely.

Until next time!

Matt

I’m taking a little bit of a different approach this week. Most weeks, I tend to focus Ask, Save, Earn on one major topic, but this week is much more of a grab bag.

However, what hasn’t changed (and won’t change) is the promise behind Ask, Save, Earn: Every edition of this newsletter will have some takeaway that you can use and apply to your own financial life.

Let’s get started.

I got a shoutout from The Purse

My friends, and , run The Purse, one of the smartest, best money sites on the planet. A week ago today, they posted a mid-year financial check-in roundup, and I was honored to be included.

Mine was about culling subscriptions, something I’ve written about here before after I found $432 in charges I’d forgotten I was even paying for.

There are nine other smart suggestions, too. One of my favorites came from Heather Boneparth, author of The Joint Account newsletter…

“Make sure your autopays are processing correctly; credit cards linked to recurring bills haven’t expired; your logins for all important accounts are still active (many have switched to 2FA); and your beneficiaries and trusted contacts are up to date. All of this will probably take you less than an hour, and it’s one of the easiest ways to prevent headaches down the road.”

Important stuff, but stuff that can be pretty easy to let fall through the cracks.

It’s also a good reminder of something that we talk a lot about here at Ask, Save, Earn: You can often do an awful lot of good in a very short time if you’re willing to put in the work.

I appeared on The Today Show!

Late last month, I did an interview with NBC News’ Emilie Ikeda that aired on The Today Show. I talked about “funflation,” or the fact that the cost of summer fun — think concerts, amusement parks, vacations, and pretty much everything else — keeps climbing faster and faster.

Here’s the segment, which includes some helpful tips for how to manage these higher prices:

I’m only in it briefly, and I’ve been on the show before, but it is always a big deal to me whenever it happens. (And maybe one day I’ll get to do an actual live segment in-studio. I can dream, right?)

Car payments just hit a record high

Holy moley! According to Experian data cited by LendingTree, the average new car payment in the first quarter of 2026 was a record $770 a month, up from $748 in Q1 2025. For used vehicles, the average is $531 a month. That’s a whole lot better than what new-car buyers face, but it is still a huge amount of money.

Before you go shopping for a new or used vehicle, I urge you to crunch the numbers to make sure you understand what you can really afford. I know that it is so easy to fall in love with that new car, truck or SUV and tell yourself, “I’m going to treat myself! I can afford it.” The person at the dealership's financing desk will probably tell you that you can afford it, too. However, unless you take the time to look at the numbers with an affordability calculator like this one from LendingTree, you just don’t know.

Buying a car is one of the most expensive things we do. It is important not to be done lightly or carelessly. If you do, you may end up regretting it for years.

Want to be the first to see some new features?

I’ve been building a couple of new features behind the scenes. I’m not going to say much about them yet because I’m just not quite ready.

However, what I will say is I need real people to test them, break them, and tell me what’s confusing or what’s missing. I’d love for you to be part of this — and maybe other tests in the future.

If you want in, reply to this email. Once the tools are ready to be looked at in the next few weeks, I’ll make sure to get you access before anyone else sees it.

Until next time!
Matt

I wanted to start this week with a sincere thank you for being part of the Ask, Save, Earn community. Whether this is the first post you’ve ever read here or you’ve been with me for years, I’m honored that you’re here.

And the community is growing! The list of free subscribers has grown 34% so far in 2026 and has more than doubled since June 1, 2025. That means the world to me, and I promise to keep bringing you meaningful content that can have a real impact on your financial life.

If you’re reading this and haven’t yet subscribed, enter your email below to do so. If you subscribe, you’ll get our free guide, “3 scripts to lower your bills today,” just for signing up.

Or if you are a subscriber and know anyone who could benefit from being part of the community, click the Share button below to share this post with them. The more, the merrier!

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Collecting incredible stories

Part of the beauty of a growing community is having more and more people’s wisdom to learn from. That includes you!

Little in my work inspires me more than talking to interesting people about cool things they did and then sharing what others can learn from their experience.

With that in mind, I’m working on a long-term project to collect stories from people who have learned something worth sharing.

I’m interested in the lessons people learned about money, work, risk, happiness, reinvention, relationships, resilience, and everything in between.

If you know someone whose story deserves to be told, I’d love an introduction.

And of course, if you have a story to share yourself, please reach out via this email, the Substack app or even in the comments below.

We all have far more wisdom than we realize. Help me share some of yours with others!

One of the most important pieces of wisdom from my book

My book, “Ask Questions, Save Money, Make More: How To Take Control Of Your Financial Life,” touches on everything from mortgages and credit cards to garage sales and wedding parties. It is about helping people pay less, earn more and keep more of their hard-earned money by asking the right questions in various everyday situations.

Nowhere is that more important than at the doctor’s office, and that’s the subject of one of my very favorite quotes from the book.

“Never, ever think that it’s not OK to negotiate a medical bill in the United States.”

Those are the wise words of the great Virgie Ellington, MD, the author of “What Your Doctor Wants You To Know To Crush Medical Debt.”

Read it again. Commit it to memory. Tell your friends about it, too.

It is that important.

Medical debt can be enormous, pervasive and can, in no uncertain terms, wreck people’s financial lives.

And here’s one more quote from Dr. Ellington:

“We assume that whatever bill we get is accurate, and nothing could be further from the truth.”

Don’t believe it? Consider this stat…

An estimated 80% of medical bills have errors. That’s a staggering number. It is absolute proof that you should never pay your first medical bill.

Mistakes aren’t always obvious

I did more than 110 interviews for my book, including plenty about medical billing. I heard multiple success stories about people negotiating their bills and saving significant money.

One of my favorite stories in the book came from my friend Kathryn Tuggle...

Tuggle, an award-winning journalist and cofounder and chief content officer of HerMoney Media, has danced for most of her life, resulting in chronic plantar fasciitis, which can cause excruciating pain. In 2019, she carefully selected a podiatrist in-network with her health insurance, meaning that the visit shouldn’t have cost more than a small co-pay. But she received a bill for $1,680. “So of course, I freak out,” she says, “thinking that maybe I got it wrong” She reviewed the bill, which indicated an out-of-network visit but no other specifics. She called the doctor’s office to request an itemized bill. “Everything the doctor had done was accurate on the itemized bill, so I’m sitting there thinking, Maybe I am going to have to pay this.*

Then she spotted the problem. The very bottom of the bill listed a different doctor than the one Tuggle had seen. Some podiatrists in that group accepted Tuggle’s insurance, but others didn’t, making them out-of-network — a common and often costly problem in hospitals and medical practices. She quickly contacted the practice to inform them of the clerical error, and after about two weeks of pushback the practice finally corrected the bill, leaving her owing nothing.

Tuggle understands why people sometimes hesitate to push back when they suspect billing mistakes. Correcting them can take a lot of time and prove frustrating. Ultimately, however, it’s well worth your time. “I probably spent four hours dealing with this problem to save close to $1,700. That’s a darn good hourly rate.”

I would say so.

What she did right

Tuggle did a lot of smart things in that situation, but the best thing she did was simply to not give up. Medical providers know full well that many people who try to lower their medical bills or to correct inaccurate bills will throw in the towel before the battle is won.

It is taking forever. It isn’t going to work. This is a waste of my time.

Medical providers are betting on you feeling that way. They’re playing the long game, doing everything they can to drag stuff out so you get so frustrated that you eventually give up.

Don’t do it.

“[People] throw their hands up because they assume there's nothing they can do, and the system seems so complicated. It seems like such a battle between David and Goliath, and they just don't realize that David can win."

The late journalist Marshall Allen, author of “Never Pay The First Bill (And Other Ways To Fight The Healthcare System And Win),” told me that in interviews for my book. Tuggle is further proof that he’s right.

Another of the most important things Tuggle did right was to ask for an itemized bill. Oftentimes, the first bill you receive will lack important details. It is crucial — whether you’re trying to negotiate a lower cost or just ensure that you’re getting charged for what you actually had done — to ask for an itemized bill with CPT codes.

CPT codes are standardized numeric or alphanumeric codes used by the healthcare industry to document and bill for medical, surgical, and diagnostic services. The first bill you get may not include them. If it doesn’t, you should ask.

When you get the bill, find the codes for the services you had done, then Google them to make sure you were billed for what you had done. If you were, then you can start thinking about negotiating that bill down. If you weren’t, contact the provider’s billing department to get it corrected, especially if you were billed for a more expensive service than you actually got.

For Tuggle, the issue was even simpler than that, though. They listed the wrong doctor on her bill, and that changed everything. But even then, with an obvious, provable mistake, it still took time to actually get it fixed. Tuggle was persistent, however, because she knew that it was worth her time.

She was right, and her efforts paid off in a big way. The next time you question a medical bill, something similar could happen to you, but only if you’re willing to put in the work.

More on medical debt

I’ll never stop talking about this topic because it's just that important.

Here’s more on Allen and his mission…

And here’s a previous story I wrote about managing medical debt…

There’s so much money involved, and people have so much more power than they realize. I’m on a mission to help them wield it, and I’m happy to have you along with me.

Until next time!
Matt

Hi there, my friend.

More than a third of Americans say they don’t plan to travel for leisure this summer, according to a new LendingTree survey.

The biggest reason?

It is just too expensive.

Unfortunately, that’s not likely to change anytime soon. Sure, gas prices have fallen significantly in the past month, but increased demand around the July 4th holiday could send them higher, as could a re-escalation of the war in Iran. However, Delta Airlines CEO Ed Bastian told Fox Business that gas prices aren’t even the biggest driver of higher prices.

“People ask me all the time – what’s happening with prices?” Bastian told FOX Business’ Maria Bartiromo in an exclusive interview on Tuesday. “Prices will come down when we can fly more, when there’s more supply, it’s a supply and demand. Right now we’re kind of logjammed.”

“There’s not a lot of supply we can bring in because the air traffic control system is congested. As you open up the skies, and you bring more flow, that’s going to help bring pricing down and enable us to bring more people to more places,” he said.

That’s not great news. The shortage of air traffic controllers is not a new problem, has caused issues at major airports in the U.S. in recent weeks, and probably isn’t getting resolved anytime soon.

So what is a traveler supposed to do?

My best advice for managing travel costs

As I always say, you have more power over your money than you think you do, and the travel space is no exception. No, you can’t open up the Strait of Hormuz or immediately hire, train and put to work thousands of new air traffic controllers, but there are plenty of things that you can control.

My best advice is really simple: Be flexible.

Generally speaking, the more fixed your plans are, the more you’ll often pay. Flexibility gives you options, and options often save money.

Of course, you can’t always be flexible. For example, you’re probably not taking your school-age kids out of school for a week in October to take advantage of those amazing airfares for a family European vacation. Nor are you going to be super eager to have your elderly parents change planes multiple times with long layovers in between just to get a cheaper airfare.

The good news, however, is that there are plenty of ways that you can be flexible to potentially help reduce your travel costs:

• Fly a day or two earlier or later. Moving your trip by even 24 hours can sometimes save hundreds of dollars.

• Be flexible on airports. Flying into or out of a nearby airport can dramatically cut airfare. That doesn’t mean you need to drive for hours to save a few bucks, but if you’re open to looking at multiple airport options, you can sometimes find real savings.

• Travel at off-peak times. Early-morning flights and off-season trips are often cheaper and less crowded. That 4 am wakeup may not be fun, but it can help you save.

• Choose the destination after finding the deal. Instead of deciding where to go first, see where the bargains are and build from there.

• Take the route with a layover. If you’re willing to put up with it, a longer travel day can sometimes mean a much lower fare.

• Mix and match airlines. Booking separate outbound and return flights can sometimes be cheaper than a traditional round-trip ticket.

• Use public transit when practical. A train or bus from the airport can be far cheaper, and sometimes even faster, than a taxi, rental car or rideshare.

• Be willing to walk or ride a bit. Staying outside the main tourist area often costs less without being overly inconvenient, especially in a city with great public transit.

• Consider a vacation rental home or apartment. Having a kitchen can save a surprising amount on meals. My family has done this many, many times. A quick trip to the grocery store at the start of the trip can really keep costs down.

• Leave some room in the itinerary. Overplanning can lead to expensive bookings and missed opportunities. A little flexibility lets you take advantage of better deals and unexpected discoveries.

• Pack light. Traveling with only a carry-on gives you more flight options and helps you avoid baggage fees.

• Rent the car from somewhere other than the airport. Taking a short shuttle, train, or rideshare ride can help you avoid hefty airport surcharges. In my book, I mention a Nerdwallet report that says you can save about 25 percent by renting away from the airport.

That’s a lot, right? And it is far from an exhaustive list.

Perhaps above all, remember this: You don’t have to treat your original plan as sacred. Weather changes, attractions close, flights get delayed, and new opportunities pop up. Travelers who adapt tend to spend less time frustrated and more time enjoying themselves. Those changes might even lead to savings, and who couldn’t use more of those these days?

Ask yourself these questions

Every traveler is different. One person’s no-brainer compromise is another person’s line they’d never cross.

So how do you decide what you’re willing to do for lower travel costs? Ask yourself some of these questions…

• What parts of this trip do I care about most, and where am I willing to compromise? A travel budget and itinerary should be a reflection of what matters most to you. If you ruthlessly prioritize what matters and slash spending on stuff you don’t care much about, it can open up a lot of possibilities. Just make sure to communicate your thoughts with the other people you’re traveling with. Otherwise, feelings can get hurt and tensions can rise.

• How much uncertainty am I comfortable with? Some travelers love booking things at the last minute. Others sleep better with everything locked in months ahead.

• Would I rather spend more money or more time? This question comes up constantly with flights, transportation, accommodations, and activities. There’s no wrong answer to this question, but it is important to consider.

Again, this is far from an exhaustive list, but it can at least help you start a conversation with yourself and those you’re traveling with. That communication is crucial, especially when you’re traveling with a group. It may not be easy, but talking through what people want and expect from a trip well before you ever leave can help avoid headaches once you arrive at your destination.

Got any travel tips to share?

Let us know in the comments below.

Until next time!
Matt

Hi there, my friend.

One year ago tomorrow, I posted this…

Spoiler alert: The big news was that Ask, Save, Earn was becoming a weekly publication. A year later, it is still going strong, despite life lifing so hard several times during that period.

The first weekly piece I did, posted the same day as the announcement, was this Q&A with author about procrastination.

If you missed it or are newer to Ask, Save, Earn, give it a read. The piece is full of practical advice and thoughtful insights, including this:

“The best way to beat the procrastination monkey is to be crystal clear and honest with yourself about your goals but also your demons, so that you know where resistance is coming from. Once you have full clarity, accountability is only between you and the person in the mirror.”

In retrospect, I love that this was the first weekly post because it touches on a fundamental theme that Ask, Save, Earn keeps coming back to:

Asking can be really hard and really scary, even if you know it works, but you can do it, and we’re here to help you.

Getting past the fear

A couple months later, I posted one of my favorite pieces of the year…

First of all, it is one of my favorite headlines of the year. But more importantly, provided real practical advice on how to get over the hump when it comes to speaking up. Not only is her book required reading at Stanford Business School — I hear that place is pretty good — but she has actually done these things herself, including getting a refund for something that she forgot to cancel.

One of my favorite quotes from Abby:

“The decision is just step one. Taking action is what actually moves the needle. My best tip? Treat yourself to some ice cream with the money you saved. That way, the victory is extra sweet (literally).”

Bribing yourself with a sweet treat? That’s something I can get behind.

You’re not alone in struggling with this

I talk to people for a living. I’ve done literally thousands of interviews with the biggest media outlets on the planet.

I still get nervous when I need to speak up. I’m still often really uncomfortable with raising my hand in a roomful of people. I shared my struggles here…

But I’m far from the only public figure who struggles with speaking up. I spoke with Chris Browning, whose Popcorn Finance podcast has been downloaded more than 2 million times, about his battles to overcome his fear of negotiating…

His primary advice:

“You have to do whatever you can to try to ground the situation and make it something less scary than your mind sometimes wants to make it be.”

That can be easier said than done, of course. However, in our Q&A, Browning lays out four tips that helped him and just might help you, too.

I won’t stop talking about this

My mission is to show everyone that they have more power over their money than they realize — and to help them wield it.

That last part is so important. Even if people know that they’ll probably get their way, they still need help knowing how to make the request.

That’s why I’m going to keep posting stories like the ones mentioned above. And I need your help to help the most people.

I always want to hear about what keeps you from taking action and what you’ve done to overcome those fears. We’re a community here at Ask, Save, Earn, and communities help each other.

I’ve said it many times…

Helping others succeed can feel every bit as good as succeeding yourself.

Here’s to another year of helping people succeed, and thank you for being a part of it.

Until next time!

Matt

Hi there, my friend.

My favorite report for LendingTree, which I put out every year, came out last week, and it has some much-needed good news for people struggling with high prices.

84% of credit cardholders who asked for a lower interest rate on one of their credit cards in the past year got one, and the average reduction was 6.3 percentage points.

That’s the highest success rate in the six years in which we’ve asked, which is saying something, given that the success rate has been lower than 76% just once — in 2022, when it was a still-sky-high 70%. It is further proof that it isn’t just people with 800 credit scores, long track records and a friend who works at the bank who get their way. Regular people who really need the help do, too.

It isn’t just interest rates that are getting lowered. Banks are waiving or reducing balance transfer fees, late fees and foreign transaction fees more often, too.

A pleasant surprise, though not all the news is good

I must confess that every year we do the survey, I get a little nervous that the success rate is going to fall off a cliff. This year was certainly no different.

Oh, man, is this the year that this stops working? There’s so much uncertainty around, well, most everything. Maybe banks will be a little less giving this year.

Nothing could be further from the truth. Banks are becoming even more willing to give a break to those who reach out, according to our data. Unfortunately, however, slightly fewer people are taking that step. Just 23% of cardholders asked, down from 25% last year.

To be clear, we’ll never have 100% of cardholders ask. About half of cardholders never carry a balance, so their interest rate doesn’t matter. (Typically, only those who carry a balance from month to month are ever charged interest, though there are some exceptions.) Many who do carry a balance don’t carry a big enough one to make it worth sweating over a few points on an interest rate. Still others don’t know they can make the call, don’t think they’ll be successful or just don’t want to try.

All that said, however, there is no question that there’s room to improve those numbers. Part of my mission is to ensure that happens.

Why this is such a big deal

My central message is that you have more power over your money than you realize, and that you can pay less, earn more and keep more of your hard-earned money by asking the right questions in various everyday situations. It is what Ask, Save, Earn is all about. It is what my book, “Ask Questions, Save Money, Make More: How To Take Control Of Your Financial Life” is all about. It is what my mission is all about.

There are few stronger examples of that power than asking for a lower interest rate on a credit card. That’s because the success rate is crazy-high, and the impact can be really significant.

Here’s what I wrote in the LendingTree post:

If you’re successful, it can save you $1,000 or more, depending on how much you owe.

Here’s how:

• The average APR reduction was 6.3 points. That’s like moving from 25.00% to less than 19.00%.

• If you have $7,000 in credit card debt, an APR of 25.00% and you pay $250 a month, you’ll pay $3,615 in interest and take 42 months to pay it off, according to LendingTree’s credit card interest calculator.

• Reduce that APR by 6.3 points to 18.7% while keeping everything else the same, and you’ll pay $2,269 in interest and take 37 months to pay it off.

That’s a savings of $1,346 from a single request — all from simply asking.

That’s a whole lot of money for a phone call. If $1,300 isn’t enough to get you to make a phone call, you’re living in a way-different tax bracket than I am.

How to do it

Not all requests you make of your credit card issuer are created equal. For example, if you want a late fee waived — and our survey showed that a record percentage of those requests were granted last year, too — chances are that all you need to do is call an 800 number and ask nicely. Sometimes it is even easier than that.

Getting an interest rate lowered may take a little bit of extra legwork, however. My book goes into great detail about what to say, including word-for-word scripts. (You can get a sample of those scripts in the free guide, “3 scripts to lower your bills today,” which goes out to all new Ask, Save, Earn subscribers.)

I also went into more detail about how to ask in the post I wrote about last year’s edition of this survey.

• It’s all about information. Got a credit card offer with a good interest rate in your email or snail mail lately? Remember it. Noticed when you look at your card issuer’s website that you aren’t getting the best rate that they’re offering? Make a note. (Here’s an example of a page where a giant bank lists all of their cards and the possible interest rates associated with those cards. Other banks and credit unions typically have something similar.) Know that your credit score has gone up recently but you haven’t told the bank? Change that. All of these things can help you frame the conversation.

  • “Hi, I have a card with a 25% interest rate, but I saw on your website that some people are being offered a rate as low as 18%. Who on your team can I talk to about getting my rate lowered?”

• Script it out. My book includes word-for-word scripts on how to ask for so many breaks from your credit card issuer, as well as other financial moves. However, if you haven’t gotten your copy yet, you can still write down what you’d like to say. Don’t worry about anticipating every single thing that could possibly happen, though. Thinking through how you’ll start the conversation, what personal details to add and how you might handle a few possible questions from the rep can go a long way to helping your confidence. You can even consider role-playing with a trusted friend to take that practice to the next level.

• Don’t be a jerk. People want to help people they like. It often really is as simple as that, so be nice. That doesn’t mean that you should be a pushover, but it does mean that you’re probably better off skipping the alpha-male BS bluster.

• Don’t be afraid to try again. The first answer isn’t always final. Sometimes you catch someone on a bad day, for example. Maybe you forgot to mention an important detail. Perhaps you didn’t think to ask to speak to the manager. Calling back and trying another time or two when you’re rejected probably won’t hurt. (After the third or fourth rejection, however, it may be time to take the hint.)

It won’t always work, but it likely can’t hurt to ask.

Even if you don’t need a lower interest rate, you could pay the knowledge forward by sharing it with a loved one who might be able to benefit from it. As good as helping yourself can feel, helping those closest to you save money can feel just as good or better.

Share your success stories

If you’ve ever done this successfully, I’d love to hear. How did you do it? What did you say? Were you scared? Was it easier, harder or about the same as you expected? Tell us in the comments below.

In other news… Happy World Cup kickoff day!

My family has been into soccer since my son started playing when he was little, so we’re all super-excited that the World Cup is here in the U.S.

We’re even going to go to a match in Dallas in a couple of weeks. We were fortunate enough to have matches that were just a short drive from Austin and to get tickets at face value early on, without having to use the secondary market.

Still, even with that, it ain’t cheap. We did a study at LendingTree that broke down the cost of going to an opening-round match in person in various parts of the country. (Spoiler alert: It is crazy high.)

Do you care about the World Cup? If so, share your predictions and hopes below.

Until next time!
Matt

Hi there, my friend.

Many people dread buying a car. It takes forever. It can be confusing. It can be intimidating. For a lot of people, especially women, it feels even worse than that.

Scotty Reiss, a longtime automotive journalist and car-buying expert who founded A Girls Guide To Cars, put it plainly when I interviewed her for my book.

“The reason a woman takes a man with her to a car dealership is not because she thinks he’s more knowledgeable about the car or haggling,” Reiss told me. “It’s because she feels like she won’t be victimized. It’s kind of like walking down a dark street at night. If you have a 6-foot-tall man with you, you’re less likely to be mugged.”

That’s a striking way to put it, but she’s right. And the thing is, the fear isn’t irrational.

Dealerships are designed to move you through a process quickly, keep you off-balance, and extract as much money as possible before you leave. The average dealership visit runs close to three hours, and most of that time isn’t even spent shopping for the car. It’s spent on paperwork, financing, and being pitched add-ons you almost certainly don’t need.

The buyers who come out ahead aren’t necessarily tougher or more aggressive than everyone else. They just show up with better information and better questions.

The single biggest mistake car buyers make

Most people wait too long to start shopping for their next vehicle. They know for months, sometimes a year or more, that they’re going to need a new car, but they put off the research until they’re desperate. Then they walk into a dealership and wonder why they feel unprepared.

“Dealerships know when you walk in the door and you’re under pressure,” Reiss told me, “so they find those points where they can provide a solution that often is really the worst solution for that buyer.”

When you’re desperate, you lose leverage, and you lose the mental space to ask good questions and actually sit with the answers. If a salesperson quotes you a monthly payment that feels high, do you have time to ask how the loan is structured and what the total cost looks like over its lifetime? If you’re walking in with a lease expiring in two weeks, probably not. Starting your research early, even when you don’t technically need a car yet, buys you the most valuable thing you can have in a negotiation: the ability to slow down and ask.

The inventory trick most buyers don’t know

Before you go to a dealership, check their website to see how many of the cars you want they actually have on their lot. A dealer sitting on 10 of the same model has a problem, Reiss said. Those unsold cars are costing them money every day, which means they’re motivated to deal. A dealer with one or two of a popular model? Not so much.

“If the dealer has ten Blazers on the lot, those Blazers are costing him money because they’re not sold,” she explained, “and so he’s going to be more negotiable.”

Use that knowledge. It tells you, before you ever walk in the door, how much room you have to work with, and it gives you a concrete reason to ask for a discount rather than just hoping one will materialize.

“I noticed you have quite a few of these on the lot. Is there any flexibility on price?” is a completely reasonable question. Walking in knowing the inventory means you already know the answer before they give it to you.

Yes, you can use competing prices as leverage

Knowledge is absolutely power when it comes to shopping for a new vehicle. Reiss told me she knew someone who was buying a Mazda at a dealership in Austin, Texas, and discovered another dealer in San Marcos, Texas – just 30 minutes south of Austin – had a better price. He simply told his salesman what the other dealer was offering and asked if they’d match it.

They did. That’s it. That’s the whole move.

This works more often than people expect, and you don’t even have to physically visit another dealership to pull it off. Sites like Kelley Blue Book, Edmunds and JD Power will show you what fair market value looks like in your region. Walk in knowing that number, and don’t be shy about referencing it.

“I’ve seen this car priced at X at two other dealerships. Can you do better?” is a completely reasonable question, and asking it shifts the dynamic immediately. You’re no longer a buyer at the mercy of one dealer. You’re a buyer with options, and dealers respond to that differently.

On the extras: just say no

When it comes to extended warranties, theft protection, undercoating, paint protection packages and other such extras, Reiss’ advice was simple: Don’t buy any of it.

“You only pay for the things you have to pay for, and don’t pay anything else,” Reiss said. The non-negotiables are the car’s price, the destination fee, taxes, and usually a small documentation fee. Everything else is profit margin dressed up as protection, she said.

When the finance manager starts walking you through add-ons, the most useful question you can ask is also the simplest: “Is this required?” If the answer is no, and it almost always will be, you can decline.

Six things to do before you buy your next car:

1. Start early. It isn’t always possible, of course, but give yourself at least six months before you actually need the car. If you do your research when you’re not under pressure, you’ll have the time and headspace to ask good questions and actually think through the answers.

2. Check dealer inventory before you visit. Go to the dealership’s website and see how many of your target car they have in stock. A full lot is your friend. Walk in and ask, “I noticed you have quite a few of these. Is there any flexibility on the price?”

3. Know the market price before you walk in. Use Kelley Blue Book, Edmunds, or JD Power to find fair market value, then ask to see the invoice price at the dealership. That’s your real baseline for negotiation, and most dealers will show it to you if you simply ask.

4. Shop around and say so. If another dealer has a better price, tell your salesperson. Ask “Can you match this?” It costs you nothing and works more often than you’d think.

5. Question every add-on. When the finance manager presents extras, ask “Is this required?” for each one. Extended warranties, protection packages, and similar products are almost always optional and almost always overpriced.

6. End every negotiation with this question. Before you sign anything, ask, “Is this the best you can do?” It’s a simple question that a surprising number of people never ask, and dealers will sometimes find more room when they think you’re about to walk out the door. It absolutely cannot hurt to ask.

Got a car shopping success story or horror story? Let us know

Not all car-buying experiences are awful, or so I hear. Tell us about your best or worst — or maybe just your most recent — experiences buying a new vehicle.

We’re all about paying it forward here, so please share in the comments below. Your experience may be able to help someone else.

So, how are you doing? Really, you can tell us…

Last week, I asked you to share your biggest financial worry right now.

Longtime Ask, Save, Earn follower Julie said this…

“I’m not even sure how to voice my biggest financial worry at the moment - because it feels like EVERYTHING…”

Can you relate? I’m sure a bunch of my readers can. If you can, share what you’re thinking in the comments below. You can also ask any questions you might have. I’m always happy to help.

Until next time,

Matt

Hi there, my friend.

As I’ve said many times here at Ask, Save, Earn, you have way more power over your money than you think you do.

Often when I talk about that power, I’m talking about the power to pay less and keep more of your hard-earned money. However, your power isn’t just about saving money. It is also about making more.

In this week’s Ask, Save, Earn, we focus on a key moment in your financial life when you have more leverage than you realize. Unfortunately, though, it’s also the moment when you’re most likely to stay quiet.

It’s when you get a job offer.

The most expensive “yes” you’ll ever say

I’ve spent years talking about how powerful it can be to ask the right questions, whether you’re negotiating a lower credit card interest rate, reducing a medical bill or doing countless other tasks.

Job offers are different, though. The stakes feel higher, and the risk feels bigger. For a lot of people, that fear leads them to do something costly: They accept the first offer.

In one of the interviews I did for my book, I spoke with Laura Adams, a financial expert, the host of the “Money Girl” podcast and the author of several books. She is someone who has worked in HR and seen the hiring process from the inside, and what she told me is something I wish everyone understood before they ever accepted a job offer.

“In a lot of cases,” Adams said, “the company would have paid higher salaries than what they were offering, but people would just immediately accept.”

The leverage you don’t realize you have

That’s the part most people never see. The number you’re given isn’t always the number they’re locked into. It’s often just the starting point.

“By the time they’ve made an offer, they’ve really chosen you,” Adams said. “That’s when you have the most leverage.”

Read that again.

They’ve really chosen you.

They’ve reviewed countless resumes, done bunches of interviews, compared you to other candidates, and they ultimately picked you to make an offer to.

That doesn’t mean you can demand anything you want, of course. It does mean that, at that point, the balance of power is tilted more in your direction than at any other point in the process. The problem is that most people feel the exact opposite in that moment.

Why people stay quiet anyway

Instead of feeling empowered, they feel scared. They worry that if they ask for more, the offer might disappear. They worry about seeming difficult or ungrateful. They worry about losing the opportunity altogether.

They worry too much, Adams said.

“In no case have I ever seen a company say, ‘You asked for more, never mind, we’re rescinding the offer’.”

Of course, it is possible to overplay your hand. If they offer $50,000 and you counter with $150,000, for example, it could leave a bad impression. In most cases, however, that fear that keeps people from asking just isn’t grounded in reality.

It is easy to give in to that fear, though. Believe me, I’ve been there more times than I’d like to admit. I absolutely, positively know that I’ve left money on the table over the years because I didn’t push. I also know, as a former manager, that the first offer is rarely final.

What is real is the money people leave on the table by staying silent. A few thousand dollars here or there might not feel life-changing in the moment, but over time, it compounds in a big way. Ideally, every new salary determines the floor for future salary negotiations. The higher you can make that floor, the better.

The “We’ll revisit this later” trap

There’s another trap that people fall into, too.

Sometimes companies will say something like, “We’ll revisit your salary in six months.” It sounds reassuring, but as Adams pointed out, that doesn’t always play out the way people expect.

“They’ll say, ‘We’ll have a review in six months,’ and then six months comes and goes, and it doesn’t happen,” she said.

Priorities change, budgets shift, managers move on. Suddenly, that future raise you were counting on vanishes, too.

“The only way to shortcut that,” Adams said, “is to ask for it upfront.”

What to do instead

The negotiations don’t need to be aggressive or turn into a big confrontation, but they do need to happen.

You’re not being difficult or needy. Instead, you’re stepping into a moment where you have more leverage than you think, and using it.

Here are a few simple ways to approach it:

1. Always counter politely and specifically. Even if the offer seems fair, it’s almost always worth asking if there’s flexibility. Something as simple as “Is there any room to move on the base salary?” can open the door.

2. Focus on your worth, not your feelings. Tie your request to your experience, skills, or market data rather than just what you want. This keeps the conversation professional and makes it easier for them to say yes. Plus, it has never been easier to find this information. Sites like GlassDoor can be incredibly helpful, but also, people are more willing than ever to share their salary information with their peers. That can be really useful in understanding what to ask for.

3. Don’t rely on future promises. If something matters to you, whether it is salary, title, remote flexibility, whatever, lock it in now. As Adams said, “We’ll revisit this later” is not a guarantee.

4. Focus on what you can gain rather than what you’re scared to lose. Again, in most cases, you’re not risking the offer by asking. However, you are risking leaving money on the table if you don’t.

What’s on your mind?

It’s a crazy time. What’s your biggest financial worry or goal right now? I’d love to hear what it is, what you’re doing about it and if I might be able to help. Share in the comments below or send me a message in the app. I’m always happy to listen and help.

Until next time!
Matt

When people think about preparing for retirement, they tend to focus on investments and savings. They’re aiming for magic-number dollar amounts and tinkering with their holdings to get themselves in the best position to reach their goals.

However, after talking with a retirement expert who’s spent years studying how Gen X approaches this phase of life, it’s clear that the risks go well beyond asset allocation or market returns.

What you don’t know, and the questions you don’t ask early enough, matter enormously, too.

Most people are guessing more than they realize

Ask someone how much they’ll need in retirement, and you’ll often get a confident answer.

Ask them how much they’re actually spending right now, and things get a lot less clear.

Janna Herron, co-author of “Retirement Bites: A Gen X Guide To Securing Your Financial Future,” said, “I think it’s really hard for people to figure out how much they’re going to spend in retirement. I think there are a lot of people who actually have no idea how much money is going out the door.”

That’s a big problem.

A lot of retirement planning is built on rules of thumb. One of the most common is that you’ll need around 80% of your current spending in retirement. However, that only works if you know what your current spending actually is.

“If the rule of thumb is you’re going to spend about 80% of what you spend now,” Herron said, “you need to know what that 100% is.”

For many people – especially those in their 40s and 50s, often at peak earning years – that number is surprisingly fuzzy. Without a clear baseline, everything built on top of it becomes an estimate stacked on another estimate.

The biggest retirement expense isn’t what most people plan for

When people underestimate retirement costs, healthcare is often where the gap shows up, Herron said.

That’s not just because it’s expensive, but because it’s unpredictable, and because the most important decisions affecting those costs happen years before retirement actually begins.

“In your 40s and your 50s is the last time that you can make a change to your health where it will make a difference in your 60s, 70s and 80s,” Herron said.

That’s a narrow window with long-term consequences.

That viewpoint reframes midlife decisions in a way most financial advice doesn’t. The habits you build, the conditions you manage, and the level of engagement you have with your own care can directly influence what you’ll spend later.

In other words, your mental and physical health today plays a massive role in your financial health tomorrow.

The problem is that this is an area where people often get very passive. That’s a missed opportunity, Herron said.

“If you can be a little bit more involved in your own health, it can really make a big difference in retirement,” Herron says

It can be as simple as asking some basic questions of your doctor. For example, making sure you understand why you’re taking a specific medication. It is OK, Herron said, to ask about generics or other less expensive options.

Never be afraid to ask questions regarding your health

If the upside is so clear, why don’t more people do this?

They don’t, in part, because these situations feel high-stakes and unfamiliar. Talking to a doctor or specialist doesn’t feel the same as calling a cable company to dispute a bill. We often just don’t think we know enough to ask the right questions, and that can make us not want to do it.

Herron suggested a useful way to rethink that dynamic.

“You’re probably an expert in something,” Herron said. “If someone asks you questions, do you ever think, ‘Oh, this person’s so stupid?’ No. No question’s too dumb. That’s the exact same thing when you’re talking to your mechanic or your doctor. That’s what they’re there for.”

If they do push back, consider that a giant, waving red flag

“If they do think you’re dumb or make you feel like you’re dumb,” she said, “then you should take your business elsewhere.”

That principle applies broadly, but it’s especially important in areas that directly affect your long-term financial security.

More simple questions to impact your healthcare costs

This isn’t about becoming a medical expert overnight. It’s about getting a little more intentional with the questions you ask in moments that most people just move through on autopilot.

Those moments add up. They can mean the difference between manageable healthcare costs in retirement and something far more overwhelming.

So if you’re looking for a practical way to start, here are a few additional questions worth having in your back pocket the next time you’re dealing with a doctor, a specialist, a pharmacist or your insurance company:

• “Is this test or procedure actually necessary right now, or can we monitor and revisit later?” Not everything needs to happen immediately. In some cases, a watch-and-wait approach can be just as effective and far less expensive.

• “What happens if I don’t do this?” This helps you understand the real stakes. Sometimes the downside is significant, but it isn’t always. Knowing the difference matters.

• “Can I get an estimate of the total cost before we move forward?” Healthcare pricing isn’t always transparent, but asking upfront can help you avoid surprises and compare options.

• “Are there lifestyle changes that could reduce or eliminate the need for this over time?” Doctors sometimes default to medication, but it may not always be necessary. This brings the conversation back to what you can control and where you might be able to reduce long-term costs.

• “What’s the cash price on this prescription?” It seems counterintuitive, but sometimes it is cheaper to not use insurance when getting prescription medications. It certainly isn’t always the case, but it is certainly worth asking. Your pharmacist should be happy to tell you. If they’re not, it is probably time to look for a new place to fill your prescriptions.

None of these questions is complicated. None of them requires a medical degree, but they do require you to speak up.

I’ve said it a million times here, but I’m going to keep saying it. You have way more power over your money than you think you do. Control what you can control by asking the right questions in everyday situations, including when you’re visiting the doctor, and it can make a real difference in your financial life.

I’m featured at Travelling Lens Insider!

Super-excited to share this Q&A that I did with the amazing Janice Kho from Travelling Lens Insider. In the piece, I share some of my best travel recommendations and money hacks to help you travel more without breaking the bank.

Check it out below…

Travelling Lens Insider

TravelMates: Matt Schulz

This is part of my TravelMates guest interview series of some of my favourite travel writers and explorers here on Substack, where they share their travel tips, recommendations and mistakes to avoid…

Read more

3 months ago · 7 likes · Janice | Travel & Photography and Matt Schulz

If you’ve followed Ask, Save, Earn for a while, Janice’s name may seem familiar. I showcased her travel tips here last fall. She’s super savvy and has a lot to teach us about travel.

Come for the travel tips. Stay for her amazing travel pics!

Until next time!
Matt

I saw two newsletter posts this week that I knew I just had to share with you.

Both described everyday situations that turned sketchy through seemingly no fault of the victims.

In one post, someone was overcharged by a restaurant. In the other, someone was bumped involuntarily by an airline.

Let’s get it into it…

The case of the mysterious restaurant overcharge

My friend Bobbi, a certified financial planner, author of multiple books and creator of the “Financial Wellness by Bobbi Rebell” Substack, went to dinner with her husband and another couple the other night.

Lovely night. Good food. Good company. The kind of evening where you are absolutely not thinking about… math.

That’s where the problem came in. The two couples each handed over a credit card and asked the server to split the check evenly.

She did just that. However, as Bobbi says in the post, when the server handed each couple their bill, “the math was not mathing.” The two bills were for the same amount, but that amount on each bill was $20 more than it should have been.

I’ll let you click the link below to read the full post and see how the story ends, but as the link says, she was warned not to mention the restaurant by name in her post to avoid being sued…

Financial Wellness by Bobbi Rebell

I was warned not to use the restaurant's name because we could get sued

Dear Friends…

Read more

3 months ago · 25 likes · 5 comments · Bobbi Rebell

The big takeaways:

1. Trust, but verify. This story is just further proof of the importance of checking your bill before you pay it and asking questions about it if something doesn’t look right. Regardless of whether the overcharge was accidental or intentional, the last thing anyone needs to do these days is pay $20 more than necessary for anything.

2. Never be afraid to ask a question about a bill that doesn’t look quite right. You should always ask politely and nicely first — accidents do happen, after all — because you catch more flies with honey than vinegar, as the saying goes. If that doesn’t work, some additional firmness and persistence may be required, but it rarely goes beyond that. Just being willing to push back on their initial response to your question often gets you where you need to go. That was true for Bobbi and her friends, but she never would’ve gotten there if she hadn’t taken the time to check the bill in the first place.

The case of the not-so-voluntary bumping

The other post I read was far more concerning. It was written by Christopher Elliott, an author, consumer advocate and journalist with whom I’ve spoken many times over the years, and I first saw it promoted on LinkedIn with the headline: “American Airlines claimed I voluntarily gave up my seat, but that’s a lie.”

In the post, Elliott tells the story of Charles Shearer, a man attempting to fly with his wife and son to his mother-in-law’s funeral in Japan. However, before they could board the first leg of their journey from Cleveland to New York, he and his family were pulled out of line and told there was only one seat available for the three of them.

Things got really messy from there, with much of the discussion centering around whether Shearer had been bumped from his flight involuntarily or not. Shearer was adamant that he was. American Airlines, Elliott reports, saw it differently.

As Elliott wrote…

Welcome to the Orwellian world of airline bumping, where “involuntary” can magically transform into “voluntary” with a few keystrokes in an airline’s computer system. It’s a neat trick that saves airlines thousands of dollars per incident. And as Shearer discovered, it’s nearly impossible to prove otherwise after the fact.

I can’t recommend reading his post highly enough. After his wife took the last seat on the original flight, Shearer and his son did ultimately make it to Japan, though on a different flight that got them there seven hours after they had intended. However, the real journey happened after they got home: a months-long adventure in pursuit of the compensation they were owed for being bumped. (Spoiler alert: It is a lot more than they were originally offered.)

Elliott does a thorough job of laying out what happened, what rights people have and what people can do if they find themselves in a similar situation. It’s an important read because what happened to Shearer and his family could happen to anyone. Flights are regularly oversold, and people get bumped all the time, whether voluntarily or not, so knowing how to protect yourself if it happens to you is crucial.

The big takeaway: Document, document, document. Elliott lays out several important, practical tips in his report, but one stood out most to me.

Document everything immediately. Send yourself emails. Text family members describing what happened. Take video, if possible. The contemporaneous nature of these communications makes them powerful evidence later.

This is good advice most any time you’re negotiating. In my book, “Ask Questions, Save Money, Make More: How To Take Control Of Your Financial Life,” I mention this many times. Good notes — who you spoke with, when you spoke with them, what they said and any other relevant details of a conversation — are protection. Whether intentionally or not, customer service reps can sometimes get their wires crossed, leading to you being told different things by different people on different days. Documenting your conversations can help you avoid that situation turning into a he-said/she-said debate that, honestly, you’re not very likely to win.

You don’t need to record audio or write down every word of every conversation. However, making note of key points is a very good idea. It can be hard to remember to do so in the heat of the moment, and few moments feel more heated than when you’re bumped from a flight against your will, but if you can keep your head as chaos unfolds around you, you’ll be glad you did.

Austin friends, see you on Saturday!

If you’ll be in the Austin area on Saturday, May 16, I’d love to see you at the Greater Austin Book Festival at the Central Library from 10 am to 5 pm.

I’m on a panel at 11 am, talking with several other authors about our publishing journeys. For the rest of the event, I’ll be signing books, telling people about Ask, Save, Earn, and generally spreading the word that you have far more power over your money than you think you do. Hope to see you there.

Until next time!

Matt

I’m keeping it quick this week because I’m in New York for another media tour, and it is a lot.

Here’s a picture from one of my interviews. This one was with ABC 7 New York. We talked about everything from balance transfer credit cards to mortgage rates to, of course, gas prices.

High gas prices have been a major theme throughout this trip, and it is easy to understand why. On Wednesday, the national average price for a gallon of regular gas was $4.53, according to AAA. That’s up 31 cents in just a week, 42 cents in a month and a wild $1.38 in a year. It’s all still well below the record of $5.02 set in June 2022, but it is rapidly closing the gap.

Around the country, some prices are downright obscene.

• California: $6.16 a gallon

• Washington state: $5.75

• Nevada: $5.23

Prices have even topped $4 in oil-rich Texas ($4.04). Those prices are enough to cause real hardship for consumers and businesses alike. So what should you do?

Control what you can control.

• Shop around. This doesn’t mean you need to drive across town to save a nickel on a gallon of gas. However, if you can find cheaper-priced gas just by going a little bit out of your way, it can make sense. Apps like GasBuddy and Waze can help.

• Adjust your work schedule. OK, in truth, you may not have that much control over this, but it may be worth asking about. Even coming into the office one fewer day each week can lead to real savings on gas. It could even help to adjust the time you begin and end your day. Driving in stop-and-start traffic can burn a lot more gas than a smooth, traffic-free trip can.

• Try carpooling. Sure, it may not be much fun to ride into work with Joe from Accounting, but sharing the commute with people who live near you and work similar schedules to you can definitely help save you money on gas. And who knows? Maybe you’ll find that you and Joe have more in common than you thought.

• Leverage credit card rewards. The right credit card, used wisely, can help you extend your budget. A simple cash-back rewards card that gives you 2% on everything you buy can be great if you’re looking for maximum returns with minimal effort. However, you can also find credit cards that give extra cash back for gas purchases and even knock a few cents per gallon off of the price at the pump. Just be cautious. Gas-station-branded credit cards can have sky-high interest rates even by credit card standards. For that reason, if you think you’re going to carry a balance, gas-station credit cards probably aren’t for you.

• Keep your tires properly inflated. Something as simple as underinflated tires can have a real impact on your car’s fuel efficiency.

And while it won’t reduce how much you spend on gas, updating your budget is a wise move right now, too. That extra cash to pay for those higher gas prices has to come from somewhere. A well-put-together budget makes it easier to find. That doesn’t mean that the choices will be easy — no one likes to have to slash their spending — but it will make it easier for you to make an informed decision. That matters a lot.

Hang in there. These gas prices won’t stay this high forever.

Hopefully.

Right?

Come see me at GAB Fest!

If you’ll be in Austin on Saturday, May 16, join me at GAB Fest, the Greater Austin Book Festival. I’m part of a panel with three other amazing writers, and we’ll be talking about our own book publishing journeys and what we learned in the process.

Our panel is at 11 am, but I’ll also spend the rest of the day at the festival — held at the beautiful Austin Central Library downtown — signing books, meeting people, signing folks up for my newsletter and more. It’ll be a lot of fun, and I’d be honored to see you there.

Want to improve your credit? This book is a must for you

While in New York, I found my LendingTree colleague Carol Pope’s incredible new book at the flagship Barnes and Noble on Fifth Street in Manhattan. It is called Credit 101, and it is exactly as it sounds. If you’re struggling with your credit or know someone who is, I can’t recommend it highly enough. (It could be a really great graduation gift, too.)

Until next time!

Matt

You’ve probably heard this advice before: Just ask. Negotiate everything. The worst that can happen is they say no.

Ask, Save, Earn readers know that I’ve said versions of that myself over the years. To be clear, I still believe that asking questions and advocating for yourself is one of the most powerful ways to pay less, earn more, and keep more of your hard-earned money.

However, the unfortunate truth is that “the worst that can happen is that they say no” isn’t always true. We don’t talk about that enough, and that needs to change.

In writing my book, I spoke about this with Stefanie O’Connell, author of “The Ambition Penalty: How Corporate Culture Tells Women To Step Up And Then Pushes Them Down.” (Preorder it now here!) She has spent years studying how people actually experience negotiation, especially when it comes to jobs, raises, and promotions, and one thing she told me really stuck:

“Everything people hear is that the worst they can say is no… but what I kept seeing was that there actually is downside risk.”

That’s a pretty big shift from the conventional wisdom, but it is incredibly important to recognize.

Understanding the risk

In real life, asking for more doesn’t always just get you a polite “no.” Sometimes, it gets you less. As O’Connell told me, people get labeled as difficult. They’re seen as too aggressive or pushy. In some cases, they miss out on opportunities they might have gotten if they’d stayed quiet.

That’s uncomfortable to hear. It runs counter to a lot of what we’ve been taught about negotiation. However, ignoring that reality doesn’t help anyone. We have to understand it to deal with it.

What makes this even more important is what happens next. O’Connell said that when people have one of these experiences, they don’t usually chalk it up to a flawed system or a bad environment. They internalize it.

“People think it is something wrong with them,” O’Connell said. “and that sticks with them for the rest of their careers.”

That’s the real cost. It is not just the missed raise or the lost opportunity. It is the hesitation that shows up the next time they should speak up and don’t.

So does that mean you should stop negotiating?

Of course not.

You should absolutely ask for more. You should question charges, negotiate bills, and advocate for yourself in your career. That never changes.

What should change, however, is how you think about risk, O’Connell said.

The people who benefit the most from asking aren’t just the ones who ask the most. They’re the ones who can afford the answer.

That’s a big distinction, and it leads to a smarter way of thinking about negotiation.

3 things to remember before you negotiate

First, lower the stakes before you ask. When everything is riding on a single outcome, every conversation feels high-pressure and high-risk. One job offer. One promotion. One client. If that’s your situation, even a small downside can hit hard.

When you have options, the entire dynamic shifts.

“If you have multiple opportunities… it lowers the stakes when things go awry,” O’Connell said.

This is why it pays to keep your LinkedIn updated, to have conversations even when you’re not desperate, and to stay open to new opportunities. It is not because you’re looking to jump ship tomorrow, but because having alternatives gives you leverage. It lets you ask without feeling like everything is on the line.

Second, pick your battles. Not every negotiation deserves the same level of effort or intensity, O’Connell said. Sometimes it makes perfect sense to push. Other times, it doesn’t.

If you’re dealing with a credit card company, a bank, or your cable provider, go ahead and ask. Those are the kinds of places where a simple question can save you real money.

“A big telecom company doesn’t need more of my money,” she said.

But if you’re dealing with a small business owner or someone providing a service where margins are tight, you might make a different choice. That’s not about being soft. It’s about being intentional. It’s about understanding when negotiating serves you and when it’s just about winning for the sake of winning.

Finally, and maybe most importantly, know the environment you’re in. Not every company, manager, or situation responds the same way to negotiation. Some places reward it, some tolerate it, and some quietly punish it.

You won’t always know which is which upfront, but there are clues if you’re paying attention, O’Connell said. Who gets promoted? Who’s in leadership? Do people like you advance there? Those signals can tell you a lot about how your ask is likely to be received.

Risk doesn’t mean that the ask isn’t worth it

At the end of the day, this article isn’t meant to scare you away from asking for more. It’s meant to help you do it more effectively.

You should absolutely ask questions. You should push for better deals and better opportunities. That’s how you save money and earn more over time.

Just don’t rely on the idea that there’s no downside. The unfortunate truth is that sometimes there is.

The goal isn’t just to ask. It is to ask in a way that protects you. You do that by building options, lowering your risk and picking your spots.

Now go out there and get what you deserve.

Until next time!
Matt

Hi there, my friend.

Ever heard the metaphor of the boiling frog?

The idea is this: If you place a frog in boiling water, it will immediately jump out, for obvious reasons. However, if you set the frog in lukewarm water and very slowly raise the temperature to boiling, the frog won’t recognize the danger until it is too late and will end up cooked.

Turns out that it isn’t really true, and that frogs really are smart enough to realize that they need to get the heck out of that water when it gets too hot. Still, it remains a useful metaphor for something that happens all the time in the business world.

And yep, you guessed it. We’re all the frogs.

One of the best examples of this is streaming services. This FoxBusiness.com piece brings up the “boiled frog” metaphor when talking about rising streaming prices, and for good reason.

According to data from CableTV.com, the price of a standard Netflix subscription has gone up from $7.99 per month in 2011 to $19.99 per month in 2026. That means we’re paying $12 a month more than we did 15 years ago, an average increase of less than $1 per month each year.

No biggie, right? We frogs definitely aren’t jumping out of the water for that, are we?

Probably not for just that one subscription. However, when you consider that the average person has 4 to 5 subscription services — and some, like me, have many more than that — the math changes.

You’re not just paying an extra $144 per year for Netflix ($12 increase X 12 months = $144). You’re also dealing with similar increases from other services, and those add up in a hurry. Increases of $144 per year on five subscription services add up to $720 a year in extra costs.

Suddenly, things get a little toasty for us frogs.

(Note: When adjusted for inflation, that $7.99 price from 2011 becomes $11.98, per the Bureau of Labor Statistics’ inflation calculator. That’s a significant difference, but it still means that Netflix subscription prices have risen far faster than inflation in the last 15 years.)

And of course, we know that we’re not just getting boiled by streaming services.

“I called, and they didn’t have a reason.”

My book, “Ask Questions, Save Money, Make More: How To Take Control Of Your Financial Life,” is filled with success stories from people who paid less, earned more and kept more of their hard-earned money by asking the right questions in various everyday situations.

In this story, author Marcus Garrett talks about price creep with insurance and a perhaps surprising truth behind it:

Just like phone bills, insurance bills tend to creep steadily upward.

Marcus Garrett, author of Debt Free or Die Trying, spotted that his monthly insurance bill had increased by $6. It wasn’t a hardship, but he wanted to know why he had to pay more. After six months, he decided to act. “I called, and they didn’t have a reason” for the increase. “They were like, ‘Oh yeah, you’re right. “ They credited the $36 back to his account and, going forward, reduced the bill by $6.

For many folks, $6 a month might not be worth their time, but there’s always value in asking why a bill increased without an obvious reason. “A lot of times, people assume they raised it for a reason, Garrett says. “I might not understand the reason, but there’s a reason behind it. That’s optimistic because the reason may just be that they can.” Also, remember that small increases add up. That one call saved Garrett $72 that year. For a tight budget, that’s a meaningful chunk of money. You probably have at least five to ten monthly bills:. house, electricity, car or transit, insurance, phone, Internet, gym, and more. Now we’re talking serious money for anyone. If a couple of three-minute phone calls can stop increases on just a couple of those bills, that’s definitely worth your time.

In truth, that business really did have a reason for increasing your bill, but the customer service rep just didn’t want to come out and say it: Sometimes businesses just raise prices because they can.

Sure, when inflation is high, businesses’ costs rise, too, and sometimes price increases are necessary. That’s fine. However, there are also times when a business just decides to reach for a little bit of extra profit, knowing that many of its customers won’t even notice. If they do notice, many won’t care.

It’s just an extra dollar or two. Meh.

You don’t have to take it, though.

What you can do about it

When businesses raise prices, they understand that a certain percentage of their customers will be upset. That’s true even if they only raise the price by a few bucks. It may not be a big portion of their customer base, but some of those upset customers are going to make themselves known, via email, social media, phone or elsewhere.

Here’s something you might not realize, though… At least some of those upset customers will get their old prices restored.

Or, to use another classic metaphor, some of those squeaky wheels will get greased. As Garrett found in the story above, often it doesn’t take much more than a phone call. They’re often happy to waive that extra $6 a month because they’ll ultimately make way more money on you in the long run if you stick around.

And talking to customer service doesn’t have to sound confrontational. If your bill went up recently, consider starting your conversation like this:

“I’ve been a happy customer for a long time, and I’d really like to stay that way. Is there anything you can do on the price?”

That’s it. No threats, no ultimatums, and it works more often than you’d think.

If you’re really nervous about making the call, consider role-playing the conversation with a trusted relative or friend a few times. The first time, have everything go as smoothly as possible. The second time, have your partner push back a little bit. Then, the third time, tell your partner to really let you have it.

It may sound goofy, but it can really help. I’ve heard countless coaches talk about wanting to make practice harder than the game, and the same concept applies here. Chances are very, very low that you’ll end up in some heated confrontation with a customer service rep. Most likely, you’ll end up thinking, Wow, that wasn’t hard at all. What was I so nervous about?

As I always try to be clear about, this newsletter is about you.

It is about helping you understand that you have more power over your money than you realize. I’m committed to showing you how to pay less, earn more and keep more of your hard-earned money by asking the right questions in various everyday situations. Every edition of this newsletter, every Thursday, will include some takeaway that you can use to better your financial life — and this one is no different.

However, sometimes in providing that information, I like to take you behind the scenes of my job.

I did that with my most recent media tour…

I did that when an announcement from the president threw a wrench into my Friday night…

I even did it a little less than a year ago when Jimmy Kimmel quoted (albeit inaccurately) a report I did in his late-night monologue…

That last one was particularly unique. I’ve been quoted and cited — or had something I wrote quoted or cited — by most any news and personal finance media outlet that you can name over the years. However, having a late-night talk-show host talk about something you write was something new for me.

To make something like that happen, you have to create content that gets people talking. Another report I wrote last week has certainly done that, too.

The number that got people talking

I recently wrote an article for LendingTree that stated that it would cost an average of more than $300,000 to raise a child over 18 years. That’s more than $17,000 per year.

Yeah, you read that right.

It’s an eye-opening report, with data put together by LendingTree’s brilliant research team, and it is absolutely worth a read. It also breaks down the costs for just the first five years, when daycare costs are brutal, as well as how costs vary by state. (For example, it can cost $400,000 to raise a kid for 18 years in Hawaii, but just slightly more than $200,000 in New Hampshire and a few Southern states. A massive difference, though also proof that parenting isn’t cheap anywhere in this country.)

The report has generated a massive amount of talk, including coverage from CBS News, Fortune, NewsNation, local TV and radio stations all over the country, and even Fox News’ morning show “Fox and Friends.”

They didn’t interview me or anyone else from LT for the segment, but that Fox & Friends conversation spurred even more coverage, including Huff Post and even TV Insider, which is not an outlet that typically picks up what I’m writing. Even IMDB (the Internet Movie Database) posted about it, linking back to TV Insider. Again, not my usual territory, but it is great to see people talking about what we wrote.

The biggest main reason why it is so great that this is being talked about is that this is a MASSIVE problem in our country.

Conversation raises awareness. Awareness, ideally, breeds action.

The takeaways from this report

As usual, I’m going to tell you that you have more power than you think you do. That doesn’t mean that everything’s going to be perfect or that managing these costs will be easy, but there are steps that you can take to help yourself.

Here’s my first recommendation from the LendingTree report…

“Start saving as soon as possible. Like today. If you’re thinking that you want to have a child in the next few years, it isn’t too early to start a fund devoted to the cost of raising a child. Put a few dollars from each paycheck into a high-yield savings account and let compounding interest work its magic. By the time your little one arrives, you’ll be glad you did.”

I know this is easier said than done, but it is absolutely essential. I always think about the old saying about the best time to plant a tree: “The best time was 20 years ago, but the next best time is today.” That is certainly the case with savings and investments, because no financial asset we have is more powerful than time. As silly as it may sound, if you know for certain that you want to have a family someday — even if it might not be for 5 or 10 years or more — start putting a little bit of money away for it. Call it your “Family Fund” and know that when your little one arrives, you’ll be thrilled that money is there.

And don’t worry that you’re not doing enough. Just get started. Start small, be consistent, and just let that money grow.

Here’s another recommendation from the report…

Take advantage of government and/or workplace benefits. Once you know your child is on the way, reach out to your company’s HR department to go over what benefits are offered for parents. If you don’t take the time to do that, you could leave money on the table, and that’s the last thing any parent should do. Also, use a dependent care flexible spending account (FSA) to pay for at least a portion of your child care costs with pretax dollars. Finally, make sure that when tax season arrives, you’re claiming all the credits you qualify for.

This stuff matters a lot. With costs as high as they are, parents need all the help they can get, so make sure to seek out as much of it as you can.

There are more recommendations in the report, as well as much more information on just what that $300,000 number includes. I highly recommend giving it a look.

Look what I found

So after finding the IMDb reference to our report, I had an idea.

I’m going to look up my name at IMDb.com.

There’s really no reason for me to be in there. I’ve never been involved in making a movie. I’ve never really been involved in making a TV show, outside of countless appearances on news shows.

Even knowing that, I looked myself up and, as it turns out, I do have an IMDb page…

At some point, someone created that page for me, with the only credit being an appearance I made on NBC Nightly News back in 2021. I have no idea who made it or why, but I think it is fun to know that I have one.

And it turns out I have Huff Post and Fox & Friends to thank for that knowledge. Who would’ve guessed?

Until next time!
Matt

Hi there, my friend.

This just in… Life’s expensive in 2026, and it isn’t likely to get much better anytime soon.

Thanks to the war with Iran, much of the talk has been about the crazy-high cost of gas — AAA says $4.16 a gallon, nationally, as I write this — but high gas prices don’t just hit us at the pump. They ripple across the entire global economy, raising the prices of most anything we buy. Pile those increases on top of the already stubbornly high prices Americans were facing for groceries, vehicles and, well, most anything else, and it just makes an already challenging situation that much worse.

It is easy to feel powerless amidst all of the chaos. However, if I’ve said it once, I’ve said it a million times, and I’ll continue to say it…

You have more power over your money than you realize. It is often just about asking the right questions.

I’m not going to BS you and tell you that you can haggle down the price of a gallon of a gas or a loaf of bread. That’s likely not going to happen.

However, there are many, many other purchases that you can pay less for — potentially much less for — just by knowing what to ask.

Two simple, powerful questions

My book, “Ask Questions, Save Money, Make More: How To Take Control Of Your Financial Life,” includes a section devoted to getting deals on shopping with retailers. I spoke with many of the most knowledgeable shopping experts in the business as I wrote it, and I heard the same thing over and over again in many of those conversations.

They all spoke about the power of two simple questions:

• Do you match your competitors’ prices?

• Are there any sales or discounts on this item right now or coming soon?

That’s it? Really? Price matching and sales?

Yes, really.

We often think negotiations over price are going to be terrifying, drawn-out and painful, but so many times, they’re just not. Often, you just need to be willing to ask.

To be clear, asking doesn’t always work. Nothing always works. However, it is usually worth trying.

By the way, the last part of the second question is key. The truth is that sometimes if an item is about to go on sale, a retailer will be willing to give you the future sales price anyway. Don’t expect them to do it if the sale is still a month away, but if you’re shopping on a Wednesday night and the sale starts on Friday, a retailer might be willing to work with you to keep you from walking out of that store.

Worst-case scenario: You still get a deal, but you have to wait a bit for it.

“Thanks for letting me know. I’ll be sure to come back on Friday when the sale starts.”

And the best news of all is that this works best on big-ticket items. Things like appliances and furniture. Things where you’re not just saving a buck or two, but potentially money that could have a real impact on your weekly budget.

Pro tip: Knowing who to talk to

As with any negotiation, it isn’t just about what or how you ask. It is also about who. For example, someone in a locally owned store may have more wiggle room on price than someone in a big corporate retailer.

Still, even in that small store, it matters who you choose. My friend, shopping expert and fellow Substacker Trae Bodge from TrueTrae.com, said it perfectly in my book:

“Read the room. If you see someone rushing, that’s not the person to ask. You want to ask the one moving slowly, stocking shelves, maybe dusting, someone who seems calm — especially if you’re shy. If someone’s dashing by, don’t expect them to stop and look in their computer for an extra sale.”

I’d love to hear your success stories. Share them in the comments below.

Until next time!
Matt