Your Money on Easy Mode
Damien Olenslager
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37 episodes — long track record
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Recent Episodes
36: You've Been Paying to File Your Taxes for No Reason
Tens of millions of Americans pay to file their taxes every year, even though most of them qualify to do it for free.This episode breaks down how the tax prep industry spent twenty years lobbying…
35: You're Probably Doing Costco Wrong
Is your Costco membership actually paying for itself — or are you just paying sixty-five dollars a year for the privilege of buying a kayak you didn't need? This episode runs the real math on one of…
34: CMA Fact vs. Fiction: Answering the Internet’s Top Questions
Most people treat their bank like a cold, long-term relationship: you aren’t happy, but breaking up feels like too much paperwork. This episode explores the "financial heresy" of officially serving…
33: Stop Paying for Someone Else’s Perks
Ever feel like you’re playing a rigged game with your money? This episode breaks down how financial products—from credit cards to bank accounts—quietly reward the savvy while charging a “lazy tax” to…
32: Better than a Bank? Meet the CMA
What do you get when you mix checking, savings, and investing…all with no fees and solid interest? According to the internet (and the comments on my most popular video), it might just be the Fidelity…
31: Spending Rules That Actually Work
If your spending keeps “mysteriously” drifting off course, it might not be your budget. It might be autopilot. This episode is all about creating simple consumption rules that slow you down just…
30: 10 Money Challenges for Real Progress
What if the fastest way to make progress with money isn’t a new budget or a higher income, but a challenge? In this episode, we explore why so many people struggle with follow-through and how small,…
29: Financial Anxiety 101: What it is and how to break the cycle
If money makes you anxious, you’re not alone—and you’re not “bad with money,” either. In this episode, we unpack how financial anxiety shows up in sneaky ways, like avoiding bills or obsessing over…
28: You're Not "Bad with Money": Unpack the early beliefs secretly shaping your financial habits
Ever wonder why money still feels stressful, even when you’re earning more? In this episode, we dig into the sneaky money scripts you picked up as a kid and how they quietly shape your habits today.…
27: Ask for More, Pay for Less: Negotiation Strategies to Boost Income and Cut Costs
Most people quietly accept whatever number their boss or cable company throws at them, and it’s costing thousands over a lifetime. This episode of Your Money on Easy Mode takes aim at the fear of…
26: Attack The $500 Leaks, Not Lattes: Cut housing, car, bills, and interest with simple scripts
What if your money problem isn’t the lattes, it’s the life costs you’ve stopped questioning? In this episode, Damien pulls back the curtain on the real budget killers: fixed costs. He breaks down how…
25: Rewrite Your Money Story: How to Break Free from Invisible Scripts
Ever feel like your money problems follow you around no matter how much you earn or save? That’s not just bad luck — it’s your invisible money scripts at work. These are the hidden beliefs we pick up…
24: To the Moon, Then What? What Reddit Didn’t Warn You About Opendoor and Krispy Kreme
What do a doughnut shop, a discount department store, and a failing real estate tech company have in common? This summer, they all became meme stock darlings—soaring hundreds of percent in days, only…
23: The Checking Account Trap: Why Parking Cash in Checking Is Risky
Is your checking account quietly draining your wealth? In this episode of Your Money on Easy Mode, we break down why parking all your cash in checking isn’t the safe move it seems. With inflation…
22: Free Money…But at What Cost? How to Avoid Losing Your Bank Bonus
That “free” $300 bank bonus? It’s real, but it’s not always easy money. In this follow-up to our beginner’s guide to bank bonus churning, we dive into the pitfalls and fine print that can turn your…
21: $300 Just to Open an Account? How Bank Bonus Churning Really Works
Ever seen those “Get $300 for opening a checking account!” offers and wondered if they’re legit? Spoiler: they are, and they can add up to serious cash. In this episode, we unpack the surprisingly…
20: You’re Not Too Late for Crypto: Here’s how to stop pretending and start understanding
Think you missed the crypto boat? Think again. In this episode of Your Money on Easy Mode, Damien picks up where the last episode left off—this time diving into how to actually get started with…
19: What the heck is crypto? A beginner’s guide that actually makes sense
What exactly is cryptocurrency, and why does it seem like everyone’s either obsessed or overwhelmed by it? In this episode of Your Money on Easy Mode, Damien pulls back the curtain on Bitcoin,…
18: When AI Gets Weird: Use prompt engineering to get smarter, clearer answers
Ever wonder why AI sometimes gives you brilliant answers, and other times total nonsense? In this episode, Damien breaks down the misunderstood concept of prompt engineering, showing how it’s really…
17: 6 Months, 1 Login, 0 Regrets: My Full Fidelity Experiment
Have you ever wondered if it’s possible to manage your entire financial life—checking, savings, retirement, college funds, healthcare, and even credit card rewards—under one roof? In this episode of…
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