Greetings,
June’s pre-order incentive for my book Real Wealth is now live. Pre-order this month, tell me you did at tylergardner.com/book, and I’ll send you a three-part exclusive podcast series—the unfiltered version of my own financial story that didn’t make it into the book. The mistakes, the pivots, the moments that actually shaped how I think about money. Delivered digitally in early July. Pre-order now and you’re also locked in for every monthly incentive through the December 1st release.
13 Moves They’re Betting You Won’t Make
Last week I spent fifty-one minutes on the phone with Xfinity.
Not because I wanted to (we live in Vermont, the nearest alternative provider is a guy named Chip who runs fiber out of a barn) but because I knew the script. You call. You tell them you’re changing providers. You get transferred to a human being who has access to a pricing tier that does not exist on any website or in any known universe.
Her name was Melanie. She saved me $43 a month. I now owe Melanie a Christmas card.
There are 13 money hacks (and I’m sure far more) that work the exact same way, and they all exist because the company is betting on one thing: you won’t ask. The hack is asking.
Here are five that you can use starting this week, one from each section of the episode. The other eight are on this week’s episode of the podcast.
From the phone hacks → The retention gambit. Call a company. Any company. Say “cancel.” You’ll be transferred to a department whose entire job is keeping you. Their pricing sheet is a different document than the public one. Geico and Progressive might knock 15-20% off. SiriusXM might drop from $17/month to $4 (or free). The move is to never take the first offer, as there are three or four layers of discount underneath it. My father recently had a retention agent ask him, and I am not making this up, how much he was willing to pay. He said four bucks. They took it. Remember: it will always be more expensive for a company to lose you than to simply drop your rate back to intro pricing.
From the tax hacks → Front-load your HSA and don’t touch it. If you have a high-deductible health plan, setup the HSA, and then max it every year. Pay medical bills out of pocket instead. Save every receipt. Let the HSA grow, invested, tax-free, for 20-30 years. Then reimburse yourself decades later, 100% tax-free. There’s no statute of limitations. A 2026 dental cleaning can be reimbursed in 2056. Triple tax advantage, which no other retirement account in America has. I wish I’d known this at twenty-five before I used my HSA to buy…Claritin.
From the consumer psychology hacks → The Costco tag code. Costco’s yellow tags are a code. .99 = regular price. .88 or .00 = display model or final sale. .97 = manager-marked clearance, 30-50% off. Little star in the top right corner = discontinued, hoard it like it’s 1999. I was told after posting about Costco earlier this month that I had committed some kind of generational crime by not already being in the Kirkland tribe. Consider this my attempt at reparations.
From the power inversion hacks → File the chargeback before you call customer service. When a company screws you, your instinct is to call them first. Don’t. Call your credit card first and file a chargeback. Visa or Mastercard freezes the charge and puts the burden of proof on the merchant. The merchant, realizing they lose automatically if they don’t act, calls you. They suddenly have all the time in the world to fix the problem they didn’t have the time to fix yesterday. The power dynamic inverts entirely. It is the single best consumer move I have ever learned. That said, and I truly mean this, only pull this lever when a company has left you no other option. It costs them real money and real reputation. Don’t weaponize it over a shipping delay.
From the hospital hacks → The bill is not the bill. When you receive a hospital bill, you need to do three things. First, request the itemized bill, as errors are routine and the discrepancy between what they charge and what they meant to charge is often startling. Second, ask about prompt pay discounts, as many hospitals will take 20-40% off if you pay in full on the spot (I have personally done this several times and saved thousands). Third, ask about charity care. Most nonprofit hospitals are legally required to offer it, income thresholds are higher than people assume, and almost nobody asks. The system is not designed for you to know any of this. Now you do.
The other eight hacks are all on this week’s episode of Your Money Guide on the Side—including the the four-minute email that earns me 27,000 Amex points annually. If you find the show useful, a review helps more than you’d think—it’s how new listeners find the show, and how I know I’m not just speaking into the endless void of personal finance podcasts.
Listen on Apple | Listen on Spotify
Two Things I’m Currently Thinking About
1. What My Elementary School Report Cards Got Wrong (Or: A Belated Defense of the B Student). Oscar Wilde once said something that I have spent thirty years wishing someone had said to me in fourth grade. Through Gilbert in The Critic as Artist: “I am afraid that you have been listening to the conversation of some one older than yourself. That is always a dangerous thing to do…”
Every single one of my elementary school report cards contained some variation of the following: Tyler rushes through his tests, finishing in fifteen minutes instead of the forty-five allotted, and consequently misses the small details that would take him from an 85 to a 100. And this was always framed as a problem. I would like to state, for the record, that I did not experience this as a character flaw at the time; I experienced it as a scheduling opportunity.
It turns out there’s an actual economic principle for this, which I did not know in fourth grade and which would have been enormously validating if I had. The Pareto Principle: 80% of results from 20% of effort. I wasn’t being careless. I was, completely by accident, practicing resource allocation. The remaining thirty minutes went toward that evening’s homework, so while my peers were completing their problem sets at home, I may have been glued to the television appreciating the most epic cartoon block of all time: Disney Afternoon.
2. Group Projects and the Mythology of the Real World. The teacher from item one also loved group projects. They all did. And you know exactly what I’m talking about. You’re assigned a project with people you didn’t choose, on a topic you didn’t select, and told (with the practiced confidence of someone delivering a profound life lesson to children who have no choice but to listen and feign inherited wisdom) that this was preparation for the “real world.”
I have some thoughts.
The real world does contain people you didn’t choose. It also contains, and the curriculum reliably omits this, the option to simply not work with them. I want to be clear that I am not good at managing people. I have tried. The people involved have also tried. We have all agreed, privately and eventually out loud, that this is not where I add value. What I do well is work quickly and alone, without the particular entropy that comes from a group project where two people do the work and four have strong opinions about the font on the cover page that ends up mattering to precisely nobody.
I say all of this with genuine affection for teachers. But the group project as universal preparation for adulthood assumes a version of adulthood that is, for a growing number of people, entirely optional. Some of us are going to end up working alone in Vermont, talking into a microphone, with a bloodhound for a coworker. No one assigned us to that group. We chose it.
For a more authoritative challenging of fourth grade curricula, see Arundhati Roy’s The God of Small Things: “…his teachers wrote in his Annual Progress Reports…Does not participate in Group Activities…another recurring complaint. Though what exactly they meant by ‘Group Activities’ they never said.”
And Before You Go…
This week’s newsletter is brought to you by Wispr Flow.
For the better part of three decades, I have operated under the assumption that I am an exceptionally fast typist. Not just fast, but gifted fast. The kind of person who finishes sentences before other people have located the shift key. The kind of person who “won” Mavis Beacon Teaches Typing even though it was never really a competition.
Then I started using Wispr Flow.
And it turns out…I am not fast. I am just slow in a way I had never compared to anything. You can talk roughly three times faster than you can type, regardless of how emotionally attached you are to your eighth grade typing score. My entire self-concept required a slight recalibration.
I now draft podcast scripts, newsletter sections, and social captions by talking. Wispr Flow converts it into clean, ready-to-use text inside Slack, Notion, Claude, ChatGPT—anywhere I’d otherwise be typing. It handles filler words, mid-sentence corrections, names, context. No setup. Works in any app on any device.
It even works on a walk in the woods with the hounds, which is increasingly where my best thinking happens anyway.
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As always, hope this gives you something to think about throughout the week ahead,
—Tyler
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