Your Money on Easy Mode

Damien Olenslager
  • 5.0 (2)
  • Self-Improvement
  • Updated Weekly

Welcome to Your Money on Easy Mode, the show that teaches you how to build wealth with minimal effort. Your host, Damien, is here to teach you how to save more, invest for your future, and enjoy the process. Damien is that weird friend who obsesses over credit card bonuses, high-yield savings account interest rates, and index fund expense ratios so you don't have to. Every week he exposes important news and tackles meaty money topics to give you an unfair advantage in the financial arena. Let's put YOUR MONEY ON EASY MODE!

  1. 42: Is inKind Actually Worth It? The Honest Breakdown

    23h ago

    42: Is inKind Actually Worth It? The Honest Breakdown

    There's a dining app called inKind that gives you up to 25% back on restaurant meals plus regular coupons, and it costs nothing to use. So what's the catch? In this episode, Damien breaks down exactly how inKind works, why the deals are real, and the one question that tells you in three seconds whether it'll save you money or quietly cost you more. You'll learn when it's a genuine win, how it stacks with your dining rewards card, and the two traps (pre-buying credit and expiring cash back) that flip a good app against you. If your favorite restaurant is on the list, this might be the easiest recurring discount in dining. If it's not, you'll know to skip it. Run the Already-Going Test and never overthink a dining deal again. Your Money on Easy Mode: practical financial clarity without the jargon, fluff, or finance-bro nonsense. New episodes weekly. This is not personal financial advice. Chapters 00:00 What is inKind? 00:59 How inKind Works 03:03 When inKind Is Genuinely Smart 04:06 The Already Going Test: Real Savings Explained 06:21 The Two Traps That Cost You Money 08:30 Homework and Final Thoughts

    10 min
  2. 41: You Gave Your Gas App Permission to What?

    Jun 7

    41: You Gave Your Gas App Permission to What?

    Your car insurance company wants to watch you drive. But in some cases, the data collection is already happening — through your gas app. In January 2025, the Texas Attorney General sued Allstate and its subsidiary Arity for secretly collecting driving data on forty-five million Americans through apps like Life360 and GasBuddy. No enrollment. No consent. Just code embedded in apps people use for entirely different things. This episode breaks down how auto insurance telematics programs actually work, what the median savings really is, when your rates can go up instead of down, and how to use the Permission-to-Profit Test before agreeing to any monitoring program. If someone in your life is weighing a telematics program, this one gives them the full picture — not just the discount brochure. Chapters 00:00 Your Car Insurer is Watching You Drive 01:54 What Telematics Actually Is 05:09 The Real Math on Savings 08:49 The Data Privacy Scandal 13:37 The Permission to Profit Test 16:59 Surveillance Creep in Consumer Products 19:50 Homework and Wrap-Up Get my free guide to where to spend your next dollar: https://stan.store/YMOEM/p/get-the-easy-mode-money-ladder-now Get my guide on how to destroy your debt: https://stan.store/YMOEM/p/get-the-easy-mode-guide-to-destroy-your-debt

    22 min
  3. 40: Did You Pick the Wrong CMA? Fidelity vs. Schwab vs. Vanguard

    May 24

    40: Did You Pick the Wrong CMA? Fidelity vs. Schwab vs. Vanguard

    Switching to a brokerage cash account was the right call. Picking the right one is the harder question — and the answer is different depending on how you actually use money. This episode runs the Cash Home Score on Fidelity, Schwab, and Vanguard across yield, access, protection, and integration. Vanguard currently leads on yield at three point three five percent with the strongest FDIC coverage — and no debit card at all. Fidelity wins on features if you set SPAXX as your core position (most people never check this). Schwab wins if Zelle is non-negotiable. Whether you're picking for the first time or reconsidering where you already are, this episode ends with a clear decision framework. Chapters 00:00 Cash Management Accounts Compared 02:03 Yield: What Your Cash Actually Earns 06:33 How Your Cash Is Protected 10:00 The Debit Card Question 13:20 What It's Like to Live in These Accounts 16:59 The Cash Home Score 19:03 But Which Account is Right for You? 20:56 Final Recommendations and Homework Get my free guide to where to spend your next dollar: https://stan.store/YMOEM/p/get-the-easy-mode-money-ladder-now  Get my guide on how to destroy your debt: https://stan.store/YMOEM/p/get-the-easy-mode-guide-to-destroy-your-debt

    23 min
  4. 39: The Passive Income Math Nobody Shows You

    May 10

    39: The Passive Income Math Nobody Shows You

    Passive income sounds simple until you run the actual math. Most popular strategies have failure rates above eighty percent, and the people selling the courses are often making more from the course than from the strategy itself. This episode uses the Passive Income Iceberg framework to expose what's hidden beneath every impressive income screenshot: the capital requirements, the upfront labor, the realistic timelines, and the numbers the platforms actually publish. We cover what a hundred thousand dollars earns you in dividends, HYSAs, and REITs right now; why seventy-five percent of course creators earn less than a thousand dollars a year; and the three-rung income ladder that reflects how passive income actually gets built. If you've been tempted by dropshipping, affiliate marketing, or an online course — or just want a realistic roadmap to income that doesn't require you to work forever — this one is built for you. Get my free guide to where to spend your next dollar: https://stan.store/YMOEM/p/get-the-easy-mode-money-ladder-now Get my guide on how to destroy your debt: https://stan.store/YMOEM/p/get-the-easy-mode-guide-to-destroy-your-debt Chapters 00:00 The Illusion of Passive Income 01:34 The Passive Income Iceberg 04:43 What Influencers Sell vs. What the Data Shows 09:05 What Genuinely Passive Income Actually Pays 13:15 The Effort-Based Streams 13:42 Effort-Based Passive Income Streams 18:24 The Time-vs-Capital Spectrum 18:46 The Passive Income Spectrum 23:43 Homework Assignment 25:03 The Full Picture of Passive Income

    27 min
  5. 38: Your Cheap Stuff Is Expensive

    Apr 26

    38: Your Cheap Stuff Is Expensive

    Cheap isn't always frugal. Every time you replace the same pan, shoe, or appliance, you're paying more than the person who bought quality once. This episode introduces the Cost-Per-Use Score (price divided by expected uses) the formula that reveals the true cost of any purchase. Damien walks through when Buy Once, Cry Once actually applies (daily-use items, the five-year test), when it's a trap (status purchases, new hobbies, hidden maintenance costs), and how planned obsolescence — a strategy costing the average household over a thousand dollars a year in tech replacements — stacks the deck against cheap buyers. The episode closes with a five-question protocol for any purchase over a hundred dollars. If you've ever replaced the same thing twice and wondered where your money went, this one's built for you. Get my free guide to where to spend your next dollar: https://stan.store/YMOEM/p/get-the-easy-mode-money-ladder-now Get my guide on how to destroy your debt: https://stan.store/YMOEM/p/get-the-easy-mode-guide-to-destroy-your-debt Chapters 00:00 "Buy Once, Cry Once" 01:27 The Cost-Per-Use Score 05:11 When "Buy Once, Cry Once" Actually Applies 09:27 When "Buy Once, Cry Once" Is a Trap 13:38 Planned Obsolescence: Grrrrrr 17:22 The Five Question Protocol 20:55 The Mental Payoff of Quality Purchases

    23 min
  6. 37: You Check Your Account Before Ordering Lunch: 5 signs your money system needs a reset

    Apr 12

    37: You Check Your Account Before Ordering Lunch: 5 signs your money system needs a reset

    Checking your bank account before buying a nine-dollar shampoo is not frugality. It is a symptom. And it is one of five specific signals that your money system has a problem worth fixing. This episode introduces the Five Money Vital Signs, a self-diagnostic that covers everyday spending anxiety, an empty emergency fund, the paycheck-to-paycheck cycle, not paying yourself first, and a financial plan that no longer fits your life. For each sign, there is a clear explanation of what is actually causing it and one concrete fix you can start this week. If your financial stress feels constant but you cannot quite name why, this episode gives you a framework and a thirty-minute homework assignment you can run tonight. Start here. Chapters 00:00 Are You Bad with Money? 00:59 The Five Money Vital Signs 02:09 You Worry About Everyday Spending 07:13 Every Inconvenience Is an Emergency 10:44 You Live Paycheck to Paycheck 14:26 You Don't Set Aside Money for Yourself 17:40 You Don't Change Your Plan 21:28 Run the Five Money Vital Signs Get my free guide to where to spend your next dollar: https://stan.store/YMOEM/p/get-the-easy-mode-money-ladder-now Get my guide on how to destroy your debt: https://stan.store/YMOEM/p/get-the-easy-mode-guide-to-destroy-your-debt

    25 min
  7. 36: You've Been Paying to File Your Taxes for No Reason

    Mar 29

    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 against free filing, hiding free options from search engines, and designing websites to push you into a paid tier. You'll get a breakdown of the options that actually cost zero dollars: IRS Free File (now with an $89,000 AGI limit for 2025 returns), Cash App Taxes, VITA, and MilTax. And the Free Filing Finder, a four-question decision tool, tells you exactly which one fits your situation before April 15th. If you've handed over a hundred or two hundred dollars to TurboTax on a simple return, this one's for you. Get my free guide to where to spend your next dollar: https://stan.store/YMOEM/p/get-the-easy-mode-money-ladder-now Get my guide on how to destroy your debt: https://stan.store/YMOEM/p/get-the-easy-mode-guide-to-destroy-your-debt Chapters 00:00 Millions are Paying for Free Filing 02:00 The Rigged Game 05:57 The "Free Filing" Lie and How to Spot It 11:30 What IRS Free File Actually Is 14:41 Direct File: RIP 15:50 The Other Truly Free Options 20:49 The Free Filing Finder 26:02 Summary and Key Takeaways

    28 min
  8. 35: You're Probably Doing Costco Wrong

    Mar 15

    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 America's most beloved warehouse stores, introducing the Payback Score: a simple framework that tells you exactly when Costco stops costing you money and starts making you money. From dog food priced at 150% more per pound at pet retailers, to allergy medication that costs nine times more at CVS for the identical molecule, to diapers and formula that can save new parents close to two hundred dollars a year — the episode breaks down five lifestyle personas and the specific products where warehouse pricing delivers a measurable return. Along the way, it names the behavioral traps — price anchoring, bulk-brain, and the Fixed Cost Fallacy — that turn a genuinely good deal into an expensive habit. If you've ever renewed a Costco membership on autopilot or wondered whether the math actually works for your household, this episode gives you a concrete answer and a homework assignment you can complete in thirty minutes. Get my free guide to where to spend your next dollar: https://stan.store/YMOEM/p/get-the-easy-mode-money-ladder-now Get my guide on how to destroy your debt: https://stan.store/YMOEM/p/get-the-easy-mode-guide-to-destroy-your-debt Chapters 00:00 Is the Costco membership worth it? 02:15 Three Costco Traps 06:05 Introducing Maya: Our Costco Composite 08:36 Persona 1: The pet parent 12:45 Persona 2: The new parent 15:59 The Bulk-Brain trap 18:46 Persona 3: The Caffeine Addict and Pantry Stocker 22:40 Persona 4: The Home Maintainer 25:35 Persona 5: The Cheap Date and Food Court Fan 27:51 Wrap-up and homework

    30 min
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Ratings & Reviews

5
out of 5
2 Ratings

About

Welcome to Your Money on Easy Mode, the show that teaches you how to build wealth with minimal effort. Your host, Damien, is here to teach you how to save more, invest for your future, and enjoy the process. Damien is that weird friend who obsesses over credit card bonuses, high-yield savings account interest rates, and index fund expense ratios so you don't have to. Every week he exposes important news and tackles meaty money topics to give you an unfair advantage in the financial arena. Let's put YOUR MONEY ON EASY MODE!

Information

  • Creator
    Damien Olenslager
  • Years Active
    2024 - 2026
  • Episodes
    43
  • Rating
    Clean
  • Copyright
    © Damien Olenslager
  • Show Website
    Your Money on Easy Mode