Your Money Guide on the Side cover art

All Episodes

Your Money Guide on the Side — 75 episodes

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Title
1

5 Money Milestones and the Lie Each One Tells

2

How to Build an Inflation-Proof Portfolio (And 3 Mistakes to Avoid)

3

13 Money Moves They're Betting You Won't Make

4

Why the S&P 500 is the Best (And Worst) Thing to Ever Happen to Investors

5

Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.

6

The 80% Problem: Why Wealthy People Don't Save for a Rainy Day

7

The 5 Best (And Worst) Cars You Could Ever Buy (Financially Speaking, Of Course)

8

How to Divorce-Proof Your Finances (Whether You're Married, Divorced, or Somewhere In Between)

9

What I'd Do If $1,000,000 Landed in My Account Tomorrow: 3 Moves, 3 Mistakes, 3 Red Flags

10

My Interview with Burton Malkiel (That You Will Never Hear)

11

The 0% Tax Bracket Most Retirees Walk Right Past

12

I Moved to Arizona for the Winter: The 5 Things Nobody Tells You About Snowbirding

13

5 Hard Truths About Investing From 26 Years at Motley Fool | Chris Hill

14

The $172,000 Retirement Surprise (And Exactly How to Avoid It)

15

Why I'm Taking Social Security at 62 (And Why the "Wait Until 70 Crowd" Might Want to Pay Attention)

16

5 AI Prompts That Will Change How You Manage Money (And 3 Things It Still Gets Dead Wrong)

17

How to Make Your Child Absurdly Wealthy for Absurdly Little

18

How to Stop Buying a Life That Isn't Yours | Hanna Horvath, CFP®

19

The Only Investing Rule You Will Ever Need

20

The $2 Million Plan No Advisor Wants You to See - The Details

21

How to Invest $5 Million (The Only 4 Portfolios You’ll Ever Need)

22

The 3 Retirement Numbers You Actually Need

23

5 Ways to Invest (And Spend) $2 Million

24

5 Things the Insurance Industry Doesn't Want You to Know

25

The 3-Day Workweek Blueprint: How to Buy Back 104 Days a Year | Andy Hill

26

The Rebalancing Lie Every Financial Advisor Tells You

27

Why I Buy Stocks at All Time Highs

28

How to Save $50,000 in Taxes by Moving Your Investments to the Right Accounts

29

Why Men Are Terrible Investors (And Lose 1% More Than Women Every Year)

30

Your Brain Is Stealing $245,000 From Your Retirement (Here's How to Stop It)

31

5 Things I Won't Do With My Money in 2026

32

The $2 Million Portfolio Plan No Advisor Wants You to See

33

The Best (And Worst) States to Retire To - Part 2 of 2

34

The Best (And Worst) States to Retire To - Part 1 of 2

35

The Real Financial Order of Operations - Part 2 of 2

36

The Real Financial Order of Operations - Part 1 of 2

37

The DIY Investor's Guide to Building Your Own Index Fund (And Why It's a Terrible Idea)

38

4 Tax Moves That Can Save You 6 Figures - Part 2 of 2

39

4 Tax Moves That Can Save You 6 Figures - Part 1 of 2

40

10 Ways Investors Lose Money Without Knowing It

41

The Only Asset Allocation Guide You’ll Ever Need

42

The Secret Art of Finding Work You Love and Funding the Life You Want | Chris Hutchins

43

How I Invest My Own Money in 2025

44

Trump vs. Obama: Whose 401(k) Made You Richer?

45

What If More Money Still Doesn’t Feel Like Enough?

46

How Do I Make My Kid Filthy Rich (Without Going Broke)?

47

How Do I Manage My Own Portfolio? 7 Steps to Start

48

When Should I Take Social Security? | Taylor Sohns

49

How do I Make ChatGPT My New (Free) Financial Advisor?

50

3 Silent Wealth Killers Hiding in Fine Print | Tess Waresmith

51

The ONLY 6 Accounts You Will Ever Need

52

How to Die With Zero | Bill Perkins

E
53

3 Reasons You’ll Never Beat the Stock Market

54

The Secret Strategies of Billion-Dollar Portfolios | Wendy Li

55

How Much Can I Spend in Retirement?

56

The Simple Path to F-You Money | JL Collins

57

10 Rules of Buying a New Car Without Getting Screwed

58

What Men Need to Hear About Money | Mady Mills

59

3 Ways to Invest $1,000,000

60

The Only Investment Guide You Will Ever Need | Andrew Tobias

61

Should I Hire a Financial Advisor?

62

On Faith, Finance, and First Principles | Dan Brigham

63

The Truth About Debt: How to Use It (And Beat It)

64

The Educator’s Guide to Money & College | Andy Schneider

65

The 3-Step Framework for Solving Any Financial Problem

66

Do Budgets Work? | Victoria Ferguson

67

On Playing to Win (The Asymmetry of Opportunity)

68

Fighting Misinformation | Jessica Inskip

69

Should I Invest in Bonds?

70

Why Cryptocurrency Matters | Mike Taormina

71

Does the Stock Market Care Who Our President Is?

72

Optimizing our Finances and our Lives | Patrick Wetherille

73

How Do I Diversify My (Digital) Assets?

74

How Do I Control My Emotions as an Investor?

75

Starting With Why