YOUR DIY FINANCIAL PLAYBOOK
Welcome to your roadmap for taking total control of your money. I believe in doing as much yourself as possible—when you manage your own finances, you’re learning new skills and keeping your hard-earned cash where it belongs, so it’s a total win-win.
My goal is truly to teach you how to do this stuff yourself. That’s why I’ve recorded hundreds of ad-free podcasts offering all the perspective and advice I wish I had known earlier in life.
To help you navigate the catalog, I’ve organized my favorite episodes into the core steps below—from shifting your mindset and reigning in spending, to investing, career growth, and designing a life you love. Dive into the roadmap below at your own pace!
The Foundation - Mindset & Learning
Podcasts to teach and inspire you to manage your money yourself. If you don’t believe you can do this yourself, then you won’t ever do it. These episodes will teach you the art of the possible, and I’d start here to decide if you want to get things in order on your own or enlist the help of a financial coach. You can find these episodes on any podcast player, and direct links to the specific episodes and show notes are below on our website.
Recommended playlist:
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The absolute best starting point to understand why you can manage your own money without paying high AUM (Assets Under Management) fees.friends on FIRE podcast #090 – Why you don’t need a financial planner – -
If you already have an advisor, here is the exact script and tactical approach to ending that relationship smoothly.Inside Out Money podcast #058 – Breaking up with your financial planner – Why and how to do it – A powerful reminder that taking control of your savings actually leads to more joy and less stress, rather than deprivation.Inside Out Money podcast #030 – Simple joys and the art of saving money – The modern introduction to redefining wealth and aligning your mindset with your financial goals.Inside Out Money podcast #114 – The inside out approach to financial freedom –
If you’ve listened to all of these, well done! Move on to the next set below.
Money & Relationships - Navigating Finances Together
Podcasts to help you get a partner or spouse on board. If you’re in a relationship, then building wealth is a team sport. Start here to align your financial goals with your partner and set your family up for success.
Recommended playlist:
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– How to handle the emotional and practical realities of merging your life and your money with another person.Ep. 028 – Love and money – navigating finances in a relationship -
– Modern frameworks you can use to divide expenses fairly and transparently.Ep. 059 – Splitting Finances with Your Partner – Practical Approaches for Financial Transparency -
– A candid debate on the pros and cons of merging accounts versus keeping things separate.friends on FIRE Ep. 034 – Split or Combined Finances -
– How to teach the next generation about intentional spending and saving.Ep. 110 – Raising financially responsible kids – Setting money expectations at every age, with a special teenage co-host -
– Scripts and strategies for handling the uncomfortable money conversations that inevitably pop up with friends and family.Ep. 099 – Well this is awkward – Financial etiquette for sticky situations
If you’ve listened to all of these, your team is on the same page and ready for the next step. Move on to the list below.
Intentional Spending and Tracking - The Art of Enough
Podcasts to inspire you to track your expenses and consider spending less. Improving your finances can be quick and simple: spend less than you make and invest the difference. But most people get hung up on the part about spending less than they make. And yes, you can focus on making more, but let’s first rein in spending. Before you can invest, you have to know where your money is going. Start here to track your expenses, decide what is enough for you, and cut the excess.
Recommended playlist:
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– A step-by-step guide to setting up your systems so you can track your net worth and budget on autopilot. If you want a referral link to our favorite expense tracking app, you can get 50% off your first year of Monarch Money here.Ep. 167 – How We Automate and Track Our Expenses – Our Favorite Monarch Tips & Tricks -
– Dive into the psychology of impulse buying and learn how to break the cycle of purchasing things you don’t actually care about.Ep. 105 – Why we keep buying stuff we don’t need and how to do better -
– Highly actionable advice and the exact scripts you can use today to negotiate down your recurring monthly expenses.Ep. 150 – How to Save Thousands on Your Bills – Scripts, Whips, & Tips -
– Practical, everyday behavioral hacks to outsmart your own impulses and keep more money in your checking account.Ep. 085 – Trick yourself into spending less money -
– A transparent look at the specific everyday items and services to cut from your budget without sacrificing your quality of life.Ep. 054 – 15 things we don’t spend money on -
– An exploration of how lifestyle creep sneaks up on you and whether spending more actually increases your baseline happiness.Ep. 007 – Do $118 yoga pants make you happier? Lifestyle creep and lifestyle satisfaction -
– Learn how to confidently cut costs on the things that don’t matter so you can spend guilt-free on the things that do.Ep. 173 – Frugal vs. Cheap – How to Build Your Personal Spending Philosophy – If you are a High Earner Not Rich Yet, this breaks down how to stop inflating your lifestyle so you can actually build wealth.Ep. 129 – Are you a HENRY? Escaping the traps so you can build wealth -
– The exact math and philosophy behind building your cash safety net so you never have to rely on a credit card in a crisis.Ep. 055 – Our formula for how much to keep in your emergency fund
If you’ve listened to all of these, that’s impressive, and you’re moving along nicely. You’ve now graduated to the next list below.
The Growth Engine - HSAs, 401Ks & Investing
Podcasts to teach you how to take the money you’re saving and grow your wealth through the magic of compound growth and time. These episodes will teach you how to leverage the right tax-advantaged accounts to grow your wealth, start investing in index funds, and more.
Recommended playlist:
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– The ultimate overview of the exact order of operations you should follow when funding your investment accounts.Ep. 033 – Step-by-step path to grow wealth – The investment walk to financial freedom -
– A glossary episode that translates Wall Street jargon into plain English so you can invest with total confidence.Ep. 076 – Investing terms you should know – ETFs vs. mutual funds, target date funds, expense ratios, dividends, market vs. limit orders, and more! -
– The eye-opening math behind how your money snowballs over time, proving why starting today beats trying to time the market.Ep. 014 – The magic of compound interest – How time and consistency build massive wealth -
– A beginner-friendly breakdown of what index funds are and why simplifying your portfolio is the smartest move you can make.Ep. 003 – How and why to invest in index funds -
– A fully transparent look under the hood at the specific types of accounts and exact index funds that actually build long-term wealth.Ep. 039 – What’s in our wallet? Our index funds, accounts, and more! -
– A deep dive into why maxing out your employer-sponsored accounts should be one of your highest financial priorities.friends on FIRE Ep. 016 – 401ks are your BFF! -
– Once you open the account, you have to actually choose the investments. Here is how to make sure your money is actually growing.friends on FIRE Ep. 142 – What’s your 401k invested in? -
– A simple breakdown of one of the most powerful tax-advantaged retirement accounts available to you.friends on FIRE Ep. 114 – What’s a rothIRA and do I need one? -
– Everything you need to know about the triple-tax advantage of an HSA and why it is a secret retirement weapon.Ep. 023 – 4 reasons HSAs are awesome and how to maximize the benefits of Health Savings Accounts
If you’ve listened to all of these, you’re set up for future success, and you can let compound interest do its magic. You’ve now graduated to the next list below.
Make More Money - Maximizing Your Income & Career
Podcasts to focus on the other side of the equation. At some point, you can only cut your expenses so much, and there might be value in focusing on growing your career and income to fuel your savings and investments faster.
Recommended playlist:
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– Tactical advice on how to negotiate your salary and increase the cash flow you have available to invest.Ep. 117 – How to make more money – career advice, asking for a raise, side hustles, and more -
– High-level strategies for navigating the corporate ladder and making yourself indispensable.friends on FIRE Ep. 121 – Career advice from 30+ years in Corporate America -
– Actionable steps to ensure your hard work translates into title bumps and higher compensation.friends on FIRE Ep. 167 – How to get promoted at work -
– Strategic advice for navigating career transitions smoothly as you level up your income.Ep. 043 – Burning bridges or building boats? How to leave a job the right way!
If you’ve listened to all of these, your earning potential is on the right track. Move on to the final set below.
The Big Picture - FI & Life Design
Podcasts on everything from happiness to FIRE (Financial Independence Retire Early) to designing a life you love. This is the graduate degree that inspires you to reclaim your time and design a life you truly love.
Recommended playlist:
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– An exploration of the different flavors of Financial Independence so you can pick the path that matches your lifestyle goals.Ep. 106 – Find your FIRE – Lean FI, Fat FI, Coast FI, Barista FI, and more! Which FIRE is right for you? -
– A discussion on Greg McKeown’s book Essentialism and how it relates to money. Learn how to focus your time, energy, and money on only the most important things for your personal happiness, rather than racing to do it all.friends on FIRE Ep. 045 – Essentialism + Money -
– Is our obsession with comfort quietly draining our wealth and resilience? We explore the mental and financial traps of modern convenience, and why leaning into voluntary discomfort builds a more resilient mind and wallet.Ep. 175 – The High Cost of Staying Comfortable – The Comfort Crisis, Stoicism, and Misogis -
– How to design a life you enjoy today while still aggressively saving for tomorrow.Ep. 146 – The Boring Middle – Stop Waiting for Retirement to Start Living -
– If early retirement feels too far away, here is the math and mindset behind taking a mid-career pause to recharge.Ep. 139 – Can I afford to take time off? Financial considerations for a sabbatical or career break -
– A look at what actually happens after you pull the plug on your career and how to navigate the transition into your next chapter.Ep. 160 – Time Wealth and Second Chapters – The Ripple Effects of Leaving Corporate America -
– A transparent look at the realities, adjustments, and freedoms of being successfully retired for four years.Ep. 161 – Our 91% vs. 9% of Life – 4 Lessons from 4 Years of Early Retirement
If you’ve made it through this entire list, you have all the tools you need to take total control of your financial life! If you still feel like you need coaching support, I’m here, but my true passion in life is teaching you how to do this stuff yourself.
FINANCIAL COACHING INFORMATION
I completely realize that DIY isn’t the path everyone wants to take, or sometimes you just hit a wall and want a sounding board to help walk you through the details.
If you reach a point where you want someone to coach you through a particular area, I offer a limited amount of private financial coaching throughout the year.
You can also work with Andrew Knight (my co-host on Inside Out Money).
Or, if you just want a one-off session with a professional, you can check out