Your Money Guide on the Side
Episodes
5 Things I Won't Do With My Money in 2026
08 Dec 2025
Contributed by Lukas
Here are a few helpful resources, from those who continue to make this show possible for and accessible to you. Visit them today to learn more! To ...
The $2 Million Portfolio Plan No Advisor Wants You to See
01 Dec 2025
Contributed by Lukas
If you’ve ever wondered how to invest $2 million—or any substantial portfolio—without losing sleep, this episode is for you. I break down a simp...
The Best (And Worst) States to Retire To - Part 2 of 2
24 Nov 2025
Contributed by Lukas
Not all “no-income-tax” states are created equal—and some of the states you’ve been avoiding might actually be financial hidden gems. In this ...
Why Retiring in Iowa Might Make You Richer Than Florida (Seriously) - Part 1 of 2
17 Nov 2025
Contributed by Lukas
Everyone will tell you to move to Florida or Texas to retire tax-free. But the truth? Taxes are more complicated than a “No State Income Tax” bill...
The Real Financial Order of Operations - Part 2 of 2
10 Nov 2025
Contributed by Lukas
This is part two of our financial order of operations series.In part one, we covered the non-negotiables—the oxygen mask, debt payoff, insurance, an...
The Real Financial Order of Operations - Part 1 of 2
03 Nov 2025
Contributed by Lukas
This week we’re tearing apart one of personal finance’s most overused frameworks: the “financial order of operations.”You’ve heard a version...
The DIY Investor's Guide to Building Your Own Index Fund (And Why It's a Terrible Idea)
27 Oct 2025
Contributed by Lukas
What if you could skip the index fund and build your own? In theory, you can. In practice…well, it’s a bit like building your own refrigerator. Yo...
4 Tax Moves That Can Save You 6 Figures - Part 2 of 2
20 Oct 2025
Contributed by Lukas
Your 50s are a tax-planning sweet spot—a decade when smart strategies can save you tens or even hundreds of thousands over the course of retirement....
4 Tax Moves That Can Save You 6 Figures - Part 1 of 2
13 Oct 2025
Contributed by Lukas
Taxes in your 50s may not be cocktail party conversation, but they can make or break your retirement plan. In this episode, I kick off a two-part seri...
10 Ways Investors Lose Money Without Knowing It
06 Oct 2025
Contributed by Lukas
Most portfolios don’t implode in one dramatic crash; they leak slowly. A percent here, a hidden fee there, and before you know it, your retirement f...
The Only Asset Allocation Guide You’ll Ever Need
29 Sep 2025
Contributed by Lukas
Your portfolio’s performance isn’t about finding the next hot stock; it’s about how you slice the pie. In this episode, I break down the real ma...
The Secret Art of Finding Work You Love and Funding the Life You Want | Chris Hutchins
22 Sep 2025
Contributed by Lukas
Guest: Chris Hutchins, host of All the HacksEpisode theme: Building wealth with meaning—how to design a career (and life) you actually want, while o...
How I Invest My Own Money in 2025
15 Sep 2025
Contributed by Lukas
Please take a moment to complete this brief survey so I can learn more about YOU and what it is YOU want from this show! I promise, it will take no lo...
Trump vs. Obama: Whose 401(k) Made You Richer?
08 Sep 2025
Contributed by Lukas
Before you hit play: I’ve put a quick listener survey together for listeners. It takes less time than finding your password for your old 401(k), and...
What If More Money Still Doesn’t Feel Like Enough?
01 Sep 2025
Contributed by Lukas
What if the biggest financial surprise in your life isn’t running out of money—but realizing that “having enough” doesn’t feel anything like...
How Do I Make My Kid Filthy Rich (Without Going Broke)?
25 Aug 2025
Contributed by Lukas
In case you missed it, check out last week's episode of Your Money Guide on the Side that answers the question How Do I Manage My Own Investment...
How Do I Manage My Own Portfolio? 7 Steps to Start
18 Aug 2025
Contributed by Lukas
In case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question: When Should I take Social Se...
When Should I Take Social Security? | Taylor Sohns
11 Aug 2025
Contributed by Lukas
In case you missed it, check out last week's episode of Your Money Guide on the Side answered the question: How do I Make ChatGPT My New Financia...
How do I Make ChatGPT My New (Free) Financial Advisor?
04 Aug 2025
Contributed by Lukas
And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question How Much Does a Financia...
Ep 26 - Tess Waresmith - 3 Silent Wealth Killers Hiding in Plain Sight (Or Small Print)
28 Jul 2025
Contributed by Lukas
Tess Waresmith is a financial educator, speaker, and investor known for helping people reach financial independence with simple investing. She’s the...
Ep 25 - The ONLY 6 Accounts You Will Ever Need (And How to Use Each of Them Strategically)
21 Jul 2025
Contributed by Lukas
In this solo episode, Tyler breaks down the only six financial accounts you’ll ever truly need—and more importantly, how to actually use them. Whe...
Ep 24 - Bill Perkins - How to Die With Zero (and Actually Live First)
14 Jul 2025
Contributed by Lukas
Is Future Planning Ruining Your Future?What if your financial advisor told you to spend your money now? To give away your inheritance early? To go on ...
Ep 23 - The 3 Reasons You’ll Never Beat the Market (And Why That’s Okay)
07 Jul 2025
Contributed by Lukas
Let’s be honest: you’re not going to beat the stock market. And that’s not an insult — it’s a liberation. In this episode of Your Money Guid...
Ep 22 - Wendy Li - The Secret Strategies of Billion-Dollar Portfolios
30 Jun 2025
Contributed by Lukas
Wendy Li managed billions for New York’s top institutions — here’s what she thinks individual investors can (and should) steal from the pros.Aft...
Ep 21 - How Much Can I Spend in Retirement? Why the 4% Rule Gets it Wrong
23 Jun 2025
Contributed by Lukas
What if the most common retirement rule was never meant to be a rule at all?In this episode, we unpack the origins, flaws, and overlooked nuances of t...
Ep 20 - JL Collins - The Simple Path to F-You Money (And Why You Need to Ask Your Boss for a Paid Leave Today)
16 Jun 2025
Contributed by Lukas
Today’s guest is someone whose work has quietly and profoundly shaped how a generation thinks about money. JL Collins is the author of The Simple Pa...
Ep 19 - The 10 Rules of Not Getting Screwed When Buying or Leasing a New Car
09 Jun 2025
Contributed by Lukas
Car buying has become one of the most financially dangerous consumer experiences in modern life. In today’s episode, we’re flipping the script.Whe...
Ep 18 - Mady Mills - Why Billionaires Panic, What Men Need to Hear, and the One Account that Buys Your Financial Freedom
02 Jun 2025
Contributed by Lukas
She’s been on Bloomberg. The New York Times. Yahoo Finance. But Mady’s real talent? Translating the chaos of markets and money into stories that m...
Ep 17 - How I Would Invest $1,000,000 - 3 Approaches, 3 Stories, and 1 Question to Simplify Your Life
26 May 2025
Contributed by Lukas
You've hit the million-dollar mark—now what?In this episode of Your Money Guide on the Side, we tackle the deceptively simple question: how sho...
Ep 16 - Andrew Tobias - The Only Investment Interview You Will Ever Need (And How Money CAN Buy Happiness)
19 May 2025
Contributed by Lukas
What if the only investment guide you ever needed... actually was?This week, I sit down with personal finance legend Andrew Tobias—bestselling autho...
Ep 15 - Should You Hire a Financial Advisor? (And 7 Things to Look For If You Do)
12 May 2025
Contributed by Lukas
This might be the most common money question I get, and maybe even the most important: Should I hire a financial advisor? And right behind it: If so, ...
Ep 14 - Dan Brigham - On Faith, Finance, and First Principles
05 May 2025
Contributed by Lukas
He paid off $100K in debt and isn’t trying to sell you a thing — meet Dan the Budget Man.In a financial world cluttered with gurus, grifters, and ...
Ep 13 - The Truth About Debt: How to Use It, Beat It, and Stop Feeling Bad About It
28 Apr 2025
Contributed by Lukas
Is All Debt Bad? What the Wealthy Know That Most People Don’tDebt doesn’t have to be your enemy—and in this solo episode, Tyler Gardner breaks d...
Ep 12 - Andy Schneider - The Educator’s Guide to Money, College, and Real-World Finance
21 Apr 2025
Contributed by Lukas
What happens when a former English teacher becomes a CFO—and decides to teach everyone around him how money actually works?In this episode, Tyler si...
Ep 11 - The 3-Step Framework for Solving Any Financial Problem (That's Actually Worth Solving)
14 Apr 2025
Contributed by Lukas
Have you ever said, “I’m just bad with money”?Yeah—me too. But what if the real issue isn’t your spending or saving or investing strategy......
Ep 10 - Victoria Ferguson - On Money, Meaning, and Saying No to Budgets
07 Apr 2025
Contributed by Lukas
What do you get when you combine a financial planner with the heart of a teacher and the boldness of a creator? You get Victoria Ferguson—today’s ...
Ep 9 - On Playing to Win (The Asymmetry of Opportunity)
31 Mar 2025
Contributed by Lukas
Most people spend their lives trying not to lose. The wealthy? They play to win.In this solo episode, Tyler Gardner breaks down the asymmetry of oppor...
Ep 8 - Jessica Inskip - On Leaving Wall Street, Fighting Misinformation, and Redefining Financial Education
24 Mar 2025
Contributed by Lukas
This week on Your Money Guide on the Side, I’m joined by the incredible Jessica Inskip—one of the sharpest, most grounded voices in modern investi...
Ep 7 - Killing Sacred Cows of Personal Finance, Or, Why I (Really) Don't Love Bonds
17 Mar 2025
Contributed by Lukas
Bonds have been a staple in portfolios for decades, often hailed as the “safe” investment that brings stability and protects wealth. But what if I...
Ep 6 - Mike Taormina - Cutting Through Crypto Noise, and a Case for Active Portfolio Management
10 Mar 2025
Contributed by Lukas
Back in 2003, I met Mike Taormina at the London School of Economics, never expecting we'd stay in touch—let alone spend decades debating financ...
Ep 5 - Political Nonsense, the Integrity of Markets, and Broken Clocks as Great Investors
03 Mar 2025
Contributed by Lukas
In this week's episode, we explore our common tendency to react emotionally to political elections and their perceived impact on the stock market...
Ep 4 - Patrick Wetherille - Managing Detractors, Working from Anywhere, and Optimizing our Finances and our Lives
28 Feb 2025
Contributed by Lukas
My guest this week, Patrick Wetherille, shares a little bit about his experience with optimizing life, managing empathy through start-up culture, and ...
Ep 3 - TikTok "Bans," Email Musts, and Building Resilience for the Inevitable Storm
28 Feb 2025
Contributed by Lukas
In this episode, I explore the power of diversifying communication channels, income streams, and the irony of many people knowing they should diversif...
Ep 2 - Market Crashes, Awkward Neighbors, and Overcoming Angel's Landing
28 Feb 2025
Contributed by Lukas
In this episode, I do my best to touch on the absolute musts of investing and controlling our emotions. Not only controlling our emotions, but knowing...
Ep 1 - Starting With Why
28 Feb 2025
Contributed by Lukas
I am thrilled to offer a brief glimpse into the "why" behind building out the podcast. The ability to add nuance, engage other minds, and le...