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

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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

Southwest Airlines is making major changes, and not in a good way. In this episode, I break down the airline’s latest moves—including the introduction of a new restrictive budget fare, the end of their non-expiring travel credits, and the shocking decision to start charging for checked bags.

These changes are a huge departure from what made Southwest a customer-friendly airline, and they could cost you hundreds in hidden fees. But don’t worry—I’ve got insider hacks to help you beat these new rules and keep more money in your pocket. I’ll also explain why Southwest is making these changes and what it means for travelers like you.

If you're a Southwest fan (or just a frequent traveler), you won’t want to miss this episode. I’ll walk you through the best ways to avoid these fees, maximize your benefits, and take advantage of little-known loopholes before the new policies take effect on May 28th. From smart booking strategies to leveraging credit card perks, I cover everything you need to know to fly Southwest without breaking the bank.

Plus, I’ll give my take on the airline’s upcoming red-eye flights, assigned seating rollout, and what these shifts mean for the future of budget air travel. Tune in now and make sure you're prepared before your next flight!

Chapters

00:00 Southwest Airlines New Policies

01:41 Impacts of Fare Changes

04:16 Fare Change Insider Secrets

06:17 RIP Free Checked Bags

09:45 Insider Tips for Dealing with Checked Bags

12:04 Travel credits now EXPIRE!

14:32 Insider Tips fro Dealing with New Cancellation Policy

16:51 Other Southwest Flight Changes

20:26 Insider Tips for Dealing with Other Changes

22:49 Conclusion

Want to build wealth without constantly watching the stock market? You don’t need to be the next Warren Buffett to succeed as an investor. In this episode, I break down my personal investing strategy—the simple and powerful 3-Fund Portfolio. No stock-picking, no market timing, just diversification, low fees, and steady growth.

You’ll learn why most professional stock pickers fail, how index funds eliminate unnecessary risk, and why bonds play an essential role in smoothing out market swings. Plus, I reveal exactly which funds I invest in (VTI, VXUS, and BND) and how you can build a stress-free, low-cost portfolio that grows over time. Whether you're a beginner or looking to simplify your investments, this episode gives you a clear roadmap to financial freedom.

Chapters

00:00 Introduction to Wealth Building

01:32 The Importance of Diversification

03:08 Diversify with Index Funds

05:13 Control Your Costs

09:00 The Role of Bonds

11:15 The Three-Fund Portfolio

12:45 VTI in Detail

15:26 VXUS in Detail

17:33 BND in Detail

19:04 Conclusion

Damien discusses the recent rebranding of YNAB (You Need A Budget) and the introduction of the term 'spendfulness.' He critiques the effectiveness of this new term and argues for a return to the straightforward concept of budgeting. He expresses his love for YNAB while highlighting its identity crisis and the need for clarity in its messaging.

00:00 YNAB Reinvents Itself

00:44 YNAB Invents A Word

03:30 Stop Tricking People into Budgeting

05:20 YNAB's Identity Crisis

06:22 Please Join the YNAB Cult

In this episode, Damien discusses the critical importance of having an emergency fund as a financial safety net. He outlines the steps to build an emergency fund, addresses common misconceptions, and provides strategies to overcome behavioral barriers to saving.

The episode also covers how to determine the appropriate size for your emergency fund, where to keep it, and how to adjust it over time as life circumstances change. Listeners are encouraged to take actionable steps towards building their emergency fund and to share their experiences.

Chapters

00:00 Introduction

01:09 Recap of Easy Mode Money Ladder

03:05 What is an Emergency Fund?

04:06 I Don't Need an Emergency Fund!

07:59 Overcome Barriers to Saving

14:17 How Much Should I Save in My Emergency Fund?

19:36 Where Should I Keep My Emergency Fund?

24:24 Adjusting Your Emergency Fund Over Time

25:48 Strategies for Building Your Emergency Fund

28:19 Viewer Feedback

In this episode of Your Money on Easy Mode, Damien discusses the fundamentals of budgeting, emphasizing its importance in achieving financial security. He introduces the concept of budgeting as a plan for money management, debunking misconceptions around the term.

The episode covers practical steps for tracking spending, organizing budgets using the 50-30-20 rule, and implementing effective budgeting strategies. Damien also highlights common mistakes to avoid, encouraging listeners to view budgeting as a tool for aligning spending with personal priorities rather than a restrictive measure.

Chapters

00:00 Intro

01:02 Defining Budgeting: A Plan for Your Money

03:36 Tracking Your Spending: The First Step

07:25 Organizing Your Budget: The 50-30-20 Rule

08:21 50% for Needs

09:57 30% for Wants

10:55 20% for Saving/Investing/Debt Repayment

11:25 Recap of Easy Mode Money Ladder

12:59 50/30/20 Example and Tweaks

15:26 Tips for Implementing Your Budget

20:53 Common Budgeting Mistakes to Avoid

22:56 Conclusion