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 Your Money on Easy Mode, Damien takes you behind the scenes of his six-month experiment: moving all of his scattered accounts into Fidelity’s ecosystem. Was it a risky move? Did it pay off?

Throughout the episode, Damien breaks down how Fidelity's Cash Management Account became his new checking and savings hub, how the 2% cash back credit card fits seamlessly into his strategy, and why he moved his IRAs, HSA, 529s, and brokerage accounts under one login. You'll hear detailed insights into Fidelity’s unique features like money market core positions, automatic investment options, low fees, and simplified management across all account types. Damien also shares practical tips for transferring accounts, maximizing rewards, and staying tax-efficient.

If you’ve ever felt overwhelmed juggling multiple banks, apps, and accounts, this episode is for you. Damien’s experiment offers real-world proof that streamlining your finances can make your life easier, your money smarter, and your future brighter. Tune in to learn why he’s (happily) never looking back—and why you might want to rethink your own financial setup too!

Chapters

00:00 The Financial Experiment

05:00 Exploring the Cash Management Account

15:53 The Cash Back Credit Card

20:42 Retirement Accounts and Investment Options

27:00 Understanding Health Savings Accounts (HSAs)

36:34 Saving for College with 529 Accounts

41:13 Brokerage Accounts and Investment Flexibility

44:09 The Results of the Experiment

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

Dreaming of a luxury vacation without the luxury price tag? In this episode of Your Money on Easy Mode, I walk you through how my family is heading to Kauai during peak holiday season—without blowing our budget. From scoring flights using the Southwest Companion Pass and Chase Ultimate Rewards, to booking a luxury resort with Costco Travel perks, I’m sharing every tip, trick, and tool we used to stretch our dollars without sacrificing the view.

Whether you're planning your first big family vacation or just looking to travel smarter, this episode is packed with actionable advice. Learn how to use the Southwest Low Fare Calendar, find honest hotel reviews on TripAdvisor, and even scout out allergy-friendly restaurants with Yelp and Google Reviews. We’ll cover flights, hotels, food, rental cars, and activities—plus how to stack points, perks, and cashback to make every dollar work harder for your trip. Let’s get you out of town the easy way.

Chapters

00:00 Introduction to Affordable Luxury Travel

01:59 Finding the Best Flight Deals

03:11 Southwest Low Fare Calendar

08:45 Paying for Flights with Points

11:20 Tips for Finding Hotels

20:30 Maximizing Hotel Stays with Points

22:22 Costco Travel: A Smart Choice

24:20 Navigating Rental Car Options

25:44 Planning Meals and Dining Experiences

31:24 Choosing Activities and Entertainment

32:34 Conclusion and Key Takeaways

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

Ask me a question: https://stan.store/YMOEM/p/personalized-video-response-54c7iwrh

You don’t need to be a tech genius to use AI to make your financial life easier. In this episode of Your Money on Easy Mode, I walk you through exactly how tools like ChatGPT, Claude, and Perplexity can help you budget smarter, plan meals on a tight grocery budget, update your resume, and even create a debt payoff strategy. These AI tools are accessible, free (or cheap), and incredibly powerful—if you know how to use them the right way.

I’ll also show you the do’s and don’ts of working with chatbots—like how to avoid “hallucinations,” protect your privacy, and turn raw AI suggestions into real-life results. Whether you want to stop staring at a blank budget or just automate boring tasks like meal planning, this episode will show you how AI can become your behind-the-scenes money assistant. Your financial life just got easier—without the burnout.

Chapters

00:00 Unlocking Financial Power with AI

01:14 Understanding Large Language Models

04:30 Meal Plan with AI

10:33 Rewrite Your Resume With AI

16:04 Create a Budget with AI

19:38 Developing a Debt Payoff Strategy with AI

22:44 3 More Quick AI Tips

24:16 Some Dangers of Using AI

26:36 Conclusion