13 Money Moves They're Betting You Won't Make

0:00As a financial advisor, I had spent a large part of my career watching people, including very smart people, leave enormous amounts of money on the table because they didn't know the ask was possible. They assumed the first number was the final number. The whole premise of modern consumer finance is that you will assume the brochure is the truth. The hacks in this episode all exist in the space between the brochure and the reality. Your job is to now close that gap. Hello friends, this is Tyler Gardner welcoming you to another episode of your Money Guide on the Side, where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance, and investing.

0:47So let's get started and get you one step closer to where you need to be.

0:55Quick note before we get into it, June's pre-order incentive for my book, Real Wealth, is the most personal thing I've ever agreed to share. pre-order in June and submit your receipt at TylerGardner.com and you'll get an exclusive three-episode audio series that will never appear on this feed. Three pivotal moments in my own financial life. The humbling one, the embarrassing one, and the one that made me rethink everything. Three episodes, three moments, TylerGardner.com, pre-order, submit your receipt, get the episodes delivered digitally in early July and receive every additional monthly incentive between now and the book's release on December 1st.

1:35And now, on to today's episode. Last week, I spent approximately 51 minutes on the phone with Xfinity. 51 minutes. I know this because I was staring at the microwave clock the entire time, and by the end, I had memorized every scuff mark on our kitchen floor, including one shaped shockingly like Rhode Island. I was threatening to cancel. Now, I wasn't actually going to cancel. The nearest alternative provider is a guy named Dave who runs fiber out of a barn, but I knew the script. You call, you say the magic word, you get transferred to a human being in a cubicle somewhere who has, crucially, access to a pricing tier that does not exist on any website, in any brochure, or in any known universe.

2:22Her name was Melanie, and that 51-minute call will save me$43 a month for the next year. I now owe Melanie, at the very least, a Christmas card. My wife Stephanie walked in around a minute 32 and found me on hold, pacing, eating saltines directly out of the sleeve, while Dixie, one of the bloodhounds, who has the emotional intelligence of a therapist and the physical coordination of a folding chair, watched me with what I can only describe as pity. At one point, Melanie put me on hold, and I'm pretty sure I could hear Dixie sigh. But here's the thing. I saved$516 a year in 51 minutes. That works out to about$650 an hour, 100 % tax-free.

3:09This whole episode is about that phone call and 12 other money moves like it. Today, we're going to have some fun and explore 13 money hacks that most people don't know about, grouped into four categories, held together by one very simple and overarching idea, which is that almost every one of these hacks exists because the company on the other end is betting that you won't ask. So if you need to go right now and you want the one key takeaway from today's episode, I'll spoil it right now. The entire hack is asking. And as I live into my philosophy as much as I can, here's a familiar ask for you.

3:52If you have found the show helpful in any way, if you've shared it with a friend or learned something new about the markets or investing or how you think about your own values, would you please consider leaving a review on Apple or Spotify? It helps other people find the show. It helps the show grow and it helps me spread the word about asking for a discount. So more money is getting put back into your pockets so you can invest it in a low cost broad-based index fund and be one step closer to where you need to be. All right, let's get into it. Act one. I call this section the phone call hacks.

4:28The following is a list of my favorite money hacks that you can fix with a phone if, and I say this genuinely understanding we're in an era where nobody under the age of 50 picks up their dang phone anymore, you can stomach the phone. Hack number one, the cancellation retention gambit. Here's how it works, and I explored this in the intro. You call whoever it is, Xfinity, SiriusXM, your gym, your cell provider, any software subscription, and the one nobody knows about, your home and auto insurance. You tell the first person you speak to that you want to cancel. You do not negotiate. You do not argue.

5:12You do not ask for a deal. You just say, I'm calling to cancel. They will transfer you. They will transfer you because every company like this has a department called retention, although it sometimes has other names, loyalty, customer care, member services. And that department's entire job is to keep you from walking out the door or disconnecting your satellite radio, if you will. Retention agents have a completely different pricing sheet than anyone else in the company. It is not public. You cannot find it online. It exists only on their screen, and they will only deploy it when they believe they are about to lose you.

5:56At GEICO and Progressive, the retention desk can knock 15 % to 20 % off your premium without changing your coverage. At most gyms, you can get three to six months free. at SiriusXM. And I cannot stress this enough. They will drop your rate from whatever you're paying to a free year. If you press it enough, they treat SiriusXM pricing the way a rug merchant treats a rug. The posted price is simply a starting offer. But here's the key here. You have to actually sound like you're leaving. You don't have to yell. You don't have to be rude. You just have to sound bored and decided like you've already emotionally left and you're just handling paperwork.

6:37Additionally, and this is the pro tip of pro tips, do not accept their first discount. More often than not, there are about three or four levels of discounts they can give you to retain you. Again, the principle being that it is far cheaper for them to keep you at a discount than to lose you as a customer. How do I know this? Because I've successfully completed this performative hack myself about 20 times in my life to date. Now, how far will they go? Well, Just ask my father. Last week, as I pointed this hack out to him years ago, and he loves seeing how low he can get some of these companies, he hopped on a call to tell company A that he was going to cancel.

7:18After staying strong through the first round of saying no to the company's first discount, they actually asked him the following, which I have personally never heard, but should prove to all of you how far they're willing to go. They asked him, well, sir, how much are you willing to pay per month. So not wanting to be a complete ding dong, he said four bucks a month. And just like that, he's happily retained customer for four bucks a month. Now, if you are uncomfortable lying, I would gently point out that you are not necessarily lying. You are expressing a preference contingent on price, which is the foundation of every economic transaction since the invention of money.

8:00It's fine, and they expect these negotiations, and the price of not making these calls is enormous. Hack number two. Call your auto insurance every 18 months. Not every year. Every year is too often. Nothing has changed in the market enough to matter, and you burn a weekend of your life for a$10 improvement. But also not every three years, because you're leaving real money on the table because rate tables drift more than you think. I have found that 18 months tends to be the sweet spot, long enough that your driving record has a fresh look, long enough that a new entrant has probably moved into your market, and long enough that your current insurer's actuarial assumptions have shifted against you.

8:47You shop three competitors, you take the lowest quote back to your current company, and you let them match it or beat it. If they won't, and sometimes they won't because the retention desk can only go so low, you can leave. I've done this four times as an adult. Average annual savings, roughly$300. That's$1 ,500 over five years, which is, among other things, a very nice weekend at a hotel that I wouldn't normally book. Hack number three, the medical bill itemization request. any hospital bill over$500. And who are we kidding? Almost every hospital bill these days is over$500 because now that's what they charge for a styrofoam cup of ice water.

9:32I want you to request an itemized bill in writing. Note, you have to get it in writing. Here's some data that unfortunately should tick you off. Consumer advocacy studies and audits have found that roughly 80 % of itemized hospital bills contain errors. 80. Almost always in the hospital's favor. This is not some conspiracy. This is because medical coding is done by human beings, often at great scale, at the end of a very long shift, and the system is built such that errors in the patient's favor get caught very quickly, while errors in the hospital's favor get caught approximately never. You, my friends, are officially now the Quality Assurance Department.

10:21You just didn't know you had the job. Once you have the itemized bill, go through it line by line. You will eventually find duplicates. You might find charges for services you didn't receive. You will definitely at some point find Motrin billed to you at$87, which even accounting for the dramatic markup of American healthcare is still absurd. Now, you might have heard that one before, but here's one that most people I know don't know and one that has personally saved me thousands. This is the second part of the healthcare hack. After you've disputed the errors, I want you to ask for the cash pay or prompt pay discount.

11:01Hospitals will routinely knock 20 to 40 % off a bill if you ask and pay within 30 days. Now, this is partly disturbing as it indicates how few people actually pay their hospital bills and that they'd rather have cash in hand at a discount than cash in hand, well, never. But it does work, and I think you'd be foolish not to at least ask what it's worth to get them cash flow immediately. For most billing departments, this request is not seen as a headache, but as a massive relief. You will actually become their favorite cheap customer because the cost of collections is brutal. They would rather get 70 cents on the dollar today than spend 18 months chasing you for the full amount.

11:44This is not a secret. It is just not advertised. So once again, ask. I have personally cut a medical bill from$1 ,100 to$640 by doing exactly this. It took one phone call, one email confirmation. The phone call was to a person whose voice, not making this up, was so bored it made me feel bored for them. But she processed it, she gave a great discount, and then she thanked me for my timely attention to this matter. All three of our first hacks have the same shape. You pick up the phone, or you pick up your laptop and write the email, and you ask a company to do a thing they are allowed to do, but don't do unless asked.

12:26If I could make anyone listening do this one single thing after this episode, it would just be this, just ask. Every week, build a muscle around asking. This episode is brought to you by keeper. Full confession. I have a sticky note on the inside of my desk drawer with passwords written on it in pen, like a person who has fully given up. My wife found it just last month and looked at me the way you look at someone who just admitted they've never flossed. Disappointment, but not surprise. The problem isn't laziness. The problem is it's an overwhelming system to begin with. The average person has north of 100 online accounts, and strong passwords look like a cat just walked across a keyboard during a thunderstorm.

13:13Nobody is memorizing capital N lowercase o capital V 3MBRT exclamation point XQ94 for their dental insurance portal. So we pick one password we can remember, slap a different number on the end, and tell ourselves it's probably fine. It is not probably fine. One breach and that recycled password unlocks everything. Your email, your brokerage, your bank, it's not one domino, it's the whole rack. Keeper generates strong, unique passwords for every account, stores them in one encrypted vault, and logs you in automatically across your devices. You remember one master password, Keeper handles the rest.

13:56And right now, Keeper is offering my listeners 60 % off personal and family plans at KeeperSecurity.com slash Tyler. This offer is only for you, our podcast listeners. That's KeeperSecurity.com slash Tyler for 60 % off personal and family plans. Make sure you use our link so they know we sent you. KeeperSecurity.com slash Tyler. This episode is brought to you by Built. You've heard me talk about BILT as the loyalty program that lets you earn points on rent wherever you live, and they just leveled up even more. As of 2026, homeowners can also earn up to 1.25x points on their mortgage payments. This is thanks to BILT's three new credit cards, the Palladium Card, Obsidian Card, and Blue Card.

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15:37Terms and limitations apply. Subject to approval and eligibility, Built cards are issued by Column N.A., member FDIC, pursuant to license from MasterCard International Incorporated. Act two, the tax codes. Before I get into these, a brief confession. As many of you know, I used to be a financial advisor, licensed, credentialed, the whole kit. Most of you know this. I wore a tie to work. I sat in offices with wood paneling that I believe was selected by a committee in 1987 and never revisited. And in my time doing that job, the single most underutilized feature of the American tax code by a country mile was the health savings account.

16:20Not the HSA everyone knows about, the spend it on band-aids HSA. The other HSA, the one that deployed correctly, is basically the best retirement account in America, and almost nobody uses it that way. So hack four, front load your HSA, then leave it alone. Here's the move. If you're on a high deductible health plan, and this is a big if because not everyone is and it's not necessarily right for everyone, but if you are, you can contribute to a health savings account. The federal limit in 2026 is $4 ,400 for individuals and$8 ,750 for families. That money goes in pre-tax, it grows tax-free, and it can be invested and most HSA custodians let you put it in index funds after a certain threshold.

17:11And here's the part that very few people know. If you use the money on a qualified medical expense, the withdrawal is also tax-free. Pre-tax in, tax-free growth, tax-free out. So that's a triple tax advantage. No other account in the American retirement system has that. Not a 401k, not a Roth IRA, definitely not your annuities. But even knowing that, here's how most people use the HSA. They put money in, they pay their medical bills out of the HSA perfectly fine because that captures most of the advantage. But here's how a smaller number of people use it. They max the HSA every year. They pay their medical bills out of pocket, out of their checking account, they save all the receipts, CVS, dentist, specialist, optometrist, everything, and they let the HSA grow, invested in index funds, tax-free for 20 to 30 years.

18:05Then, in retirement, or whenever the heck you want, once the HSA has had years or decades to take advantage of uninterrupted compounding, they reimburse themselves for those decades-old medical expenses tax-free at any time. There is no statute of limitations on HSA reimbursement. A dental cleaning you paid for in 2026 can be reimbursed from your HSA in 2056. The IRS doesn't care. They just want to make sure you have the receipt. So what I would do is take a photo of each receipt and stick it somewhere in the cloud. What you've done is turn your HSA into the best retirement account you could ever ask for.

18:45You've taken an account meant for medical expenses and turned it into tax-free retirement money by the simple trick of deferring the reimbursement. Now, again, I'm not assuming we all have access to an HSA, and I'm definitely not assuming that we can all do this and max it out. But if you do have the cash flow to front load it without dipping into it, I would suggest you do this. Because this is a hack, I wish I'd started doing a 25. My HSA would have several hundred thousand dollars in it by now. Instead, I used mine at 25, probably to buy Claritin. Hack five, the Roth conversion in a gap year.

19:22Let me start with this. I didn't fully appreciate Roth contributions until I was making too much money to contribute to one. And now it's kind of too late for me to take advantage of it. I know, cry me a river, Tyler. But if you have a low income year, sabbatical, layoff, parental leave, starting a business, early retirement, year between jobs. That's the year of note. And I want you to note that you don't have to wait until you retire to take advantage of a Roth conversion gap year. It's sold to most people that they should do it between early retirement and 73, but I would suggest there are far better opportunities earlier in your life and career.

20:05Anyway, here's what's happening. You have money in the traditional IRA or 401k, as stats say most of us do. That money was deposited pre-tax, which means at some point has to come out and be taxed. But you can convert it, move it dollar for dollar into a Roth IRA where it will never be taxed again. The catch is the year that you convert, the conversion counts as ordinary income. So if you do the Roth conversion in a normal year when your salary is six figures plus, you can get hammered. It might not be worth it at all as the conversion stacks on top of your regular income and much of it gets taxed at your highest marginal rate, which is probably 24 or 32%.

20:48But if you do a Roth conversion in a gap year, when your salary is zero or close to it, which many of us do actually experience in our lifetimes. A big chunk of that conversion falls into the 10 or 12 % bracket. You are converting at tax rates you will likely never see again. I had a client do this once, took a year off to take care of her mother, converted$80 ,000 from traditional to Roth, paid about$9 ,000 in federal tax on it. If she'd done that conversion in a normal working year, it would have cost her closer to$22 ,000. The gap year saved her$13 ,000 for doing exactly one thing differently on her tax return.

21:31Most people in a low-income year, I appreciate, are just trying to survive. Been there, done that. But if you can scrape the cash together for the tax bill, and the tax bill is the only real cost because you're moving money you already have, a gap year Roth conversion is one of the highest leverage moves in the American tax code. And no, you don't need to wait until retirement to be thinking about this. Hack number six, appeal your property tax assessment. As many of you know, your town assesses your home's value. That assessment is the input to your property tax bill. Fewer of you know you can appeal this.

22:13And even fewer of you know, In most towns in America, fewer than 5 % of homeowners ever do. The ones who do win reductions about 40 % of the time. It's a 45-minute process. You pull three or four comparable sales from the last year, houses in your neighborhood, similar square footage, similar lot size, that's sold for less than your town's assessment of your home. You fill out a form. You submit it. In some towns, you have to show up in person to a hearing that lasts about six minutes and involves a man named Stan who's been doing this since 1983. But potential savings are hundreds to thousands per year, every year forever, because your assessment, once reduced, stays reduced until the next full-town revaluation, which, in Vermont, happens roughly every 11 billion years, and in parts of New England, I cannot name without getting sued, has apparently only happened once during the Carter administration.

23:12My father appealed his five years back, won a reduction of 8%. That saves him roughly$700 a year. Over 15 years, that's$10 ,500 for a 45-minute appeal. If someone offered you$10 ,000 to spend 45 minutes on a DMV-adjacent website, my guess is you would say yes so fast you would probably sprain something. This episode is brought to you by Gelt. Quick question. How did your CPA treat you this tax season? Did they reach out proactively, walk you through your options, and make you feel like a priority? Or did you hear from them in mid-March, feel rushed, and wonder afterward if you left money on the table?

23:56That second experience is not normal. You just haven't experienced a great CPA yet. A great CPA is a year-round partner, not a once-a-year fire drill. And Q2 is the best time to make a switch. Your new CPA has bandwidth, your numbers are fresh, and there's a full year ahead to make moves that actually matter. Gelt is offering two things for new clients who sign up before June 30th. If you filed an extension, a focused 30-minute session to find everything that can still impact your 2025 taxes before October. And for any new client onboarding in Q2, Gelt will go back through recent returns and find deductions you may have missed.

24:38Both are paid add-ons that often cost you nothing net by the time they're done. So if your CPA made you feel like an afterthought this season, go to joingelt.com slash Tyler. That's J-O-I-N-G-E-L-T dot com slash Tyler. Act three, the consumer psychology hacks. These are small moves that simply consist of pattern recognition and knowing the game. Hack number seven, the Costco price tag code. Now, before I say anything on this one, I will just say, dear Lord, I guess I've truly been living under a rock in the woods of Vermont because I had no idea the Costco tribe was as passionate about their Costco as it is.

25:24I posted two videos this past spring about the best and worst deals at Costco, and in three years of creating content, I have never, and I mean never, received as much negative feedback about treading on thin ice by even mentioning Costco as someone who's not officially part of the tribe. So as a preface to this section, I am always and forever literally just talking about financial education, and I make no claims on the values of Costco, the chemicals present or not present in their rotisserie chicken, and how valuable the Kirkland executive membership is or isn't to you and your brethren. So this is me treading lightly, and I appreciate your kindness in advance.

26:06Costco is a system. The prices on the yellow tags mean things. They are a secret code that's not really a secret, but since many people don't read the tags, it is functionally secret. So for those who don't know about this or need a reminder about this, here it is. Prices ending in 99 cents, regular price. No story, nothing interesting. Buy it if you want it. Prices ending in 88 or 00, like$1 ,999 and no cents, those are display models or final sale items, usually appliances, TVs, furniture. The store is trying to clear them out. Prices ending in$0.97, manager marked clearance. This is the money one.

26:52When you see a price ending in$0.97, the manager has personally marked it down because the item is either overstocked, discontinued, or seasonally obsolete. Savings are typically 30 to 50%. Also, a little star on the tag in the top right corner, lovingly known as the Death Star. That means the item is being discontinued from Costco's inventory, and once it's gone, it's gone. So if you love a specific brand of trash bag or hot sauce and you see a star, you better be hoarding it, baby. And my guess is you already are, because you're a member of Costco. Hack number eight. buy appliances the second week of September or the first week of May.

27:39New appliance models drop in October and June. Retailers tend to clear out old inventory three to five weeks before the new stuff lands. The markdowns are real, 20 to 40 percent, and because salespeople on the appliance floor work on commission tied to moving old stock, they will tend to be able to negotiate even further. You can often shave another 5 % just by asking a human being at Lowe's if there's any more room. There usually is. Again, this involves simply asking and making it clear that you're looking for something slightly cheaper. This also works on mattresses, TVs, furniture, and for reasons I do not fully understand, gas grills.

28:24something about the grill industry's calendar, I guess. Regardless, it's legit and it simply involves asking. Hack number nine, price protection on credit card purchases. Now, this one is kind of a vanishing feature, so make sure you check yours specifically or give them a call. But many major credit cards have or have had a price protection window of 60 to 90 days. So if you bought something at one price and it drops to a lower price within the window, you can file a claim with your card company and they will refund the difference. Chase still does this on some cards. Amex offers a version of it.