All Episodes
Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance) — 340 episodes
Why Don't We Feel We Can Retire With Numbers That Look Good? | Early Retirement Hotline
The Shocking Reality Of What A $5M Retirement Looks Like In 2026 | Early Retirement Hotline
Can I Retire At 52? | Early Retirement Hotline
Should I Do Roth Conversions With A Pension? | Early Retirement Hotline
Can I Retire At 55 With $1M+? | Early Retirement Hotline
Can I Retire At 55 And Spend $10K/month? Early Retirement Hotline
This 59-Year-Old Might Retire..Or Make a Huge Mistake | Early Retirement Hotline
Working at 44… But Wondering If Retirement Is Closer Than He Thinks | Road to Retirement
Special Honeymoon Episode & Early Retirement Workshop Announcement
Business Owner Near Retirement Reveals Difficulty Of Knowing How Much Is Enough | Road to Retirement
Retiring at 62 After a Health Scare Changed Everything | Road to Retirement
Ex-Cybersecurity Expert Reveals How He Retired At 52 | Road to Retirement
Why I Want To Work Part-Time In Retirement | Road to Retirement
Why I Chose To Retire At 70 (Surprising Truth Revealed) | Retirement Reality
Why I Love Working For A Purpose, Not Money | Retirement Reality
Ex-Federal Employee Reveals Overcoming Obesity And Importance of Retiring In Your 50s | Retirement Reality
The Psychological Factor In Retiring Early | Retirement Reality
Single Mom Reveals How She Retired At 54 | Retirement Reality
Retiring at 58 Wasn’t the Plan, Here’s Why He Did It Anyway (& You Should Too) | Retirement Reality
Ex-Physician Reveals Why He Still Can’t Fly First Class | Retirement Reality
Single Retiree (57) Breaks Down Exactly Why You Should Retire Today | Retirement Reality
Early Retiree Reveals The Truth About Finding Purpose In Retirement | Retirement Reality
Special Episode: NEW Free Resource For Loyal Listeners!
Ex-Software Engineer Reveals Dark Truth Behind “Never Turning Off” | Retirement Reality
Retiree Reveals Why She Retired At 56 Without A Purpose | Retirement Reality
Ex-Tech Reveals The Regrets To Avoid Before Retirement | Retirement Reality
Here’s How A Retiree Spends $10K/Month Safely in Retirement | Retirement Reality
“I Would Rather Figure Retirement Out Than Continue My Job” | Retirement Reality
“Stop Worrying About Healthcare Pre-65” | Retirement Reality
New Retiree Shares How He Retired At 58 | Retirement Reality
Single Retiree Shares Surprising Truth About Retiring Earlier Than His Peers | Retirement Reality
"I Started Investing In My 30s And Retired At 53" | Early Retiree Shares All | Retirement Reality
Why Retirees Are Flocking To This One Special Community | Retirement Reality
Ex-Silicon Valley Retiree Reveals Why You Should Retire EARLY | Retirement Reality
When Is The Ideal Time To Hire An Advisor?
This Is When I Recommend You STOP Saving For Retirement
The Shocking Statistics Behind When People Collect Social Security
Why Risk Tolerance Doesn't Matter (Use THIS Instead)
How To Decide When To Turn On Social Security
How Much Fixed Income Do You Really Need in Retirement?
Why Asset LOCATION (NOT "Allocation") Overlooked In Retirement Planning
When Saving Becomes a Habit You Can’t Turn Off | Root Talks
You Want To Retire By 55. Here's 5 Things You Need To Know.
The Shocking Reason Most People Work Past 60
James Threw the First Pitch at a Padres Game—Here’s the Real Lesson | Root Talks
Why Only 3% of US Retirees Have Over $1M
Here's How Your Spending Will Change Throughout Retirement (The Retirement Smile)
Will Low Returns Ruin Your Retirement? (How to Interpret Goldman Sachs 3% Forecast) | Root Talks
How To Save On Healthcare In 2026 (If Retired)
Here's Exactly How To Withdraw From A 401(k)/IRA To Live In Retirement
A Beginner's Guide To Roth Conversions
The Cliché Advice You Should Finally Pay Attention To
7 Benefits Of Brokerage Accounts (Superhero)
6 Surprising Statistics About Wealthy Retirees
How to Know You’ve Found the Right Financial Advisor │ Root Talks
This Is What The Average Retiree Spends In Retirement
10 Questions To Ask Your Spouse So They Are Excited For Retirement
Inside Root’s Growth Plan (And the Promise Refuse to Break) │ Root Talks
What's The Average 401(k) Balance At My Age? Am I On Track?
4 Massive Reasons You'll Wish You Retired Earlier
The Hidden Cost of Financial Optimization (And How to Avoid It)
I Want To Retire (Or Just Work Less). Will I Still Be On Track For A Comfortable Retirement?
FAQs: Wills, Trusts, Power of Attorneys, and Other Estate Planning Tools (Part 2)
Does Your Spouse Really Know the Financial Plan? Why That Matters │ Root Talks
Here's When A Will Is Sufficient And Trust Isn't Necessary (Part 1)
Why I Love Retirement Planning At 29 Years Old
How to Know If You’re Ready to Retire (Hint: It’s Not Just About Money)
5 Surprising Statistics That Will Make You Want To Retire Early
Here's How To Plan For Social Security If You Retire Early
DIY vs. Financial Advisor: How to Know When It’s Time to Get Help
The Not-So-Obvious Reason To Retire Early
Why Retire Early? History Of The Podcast
Why Brokerage Accounts Might Be the Most Underrated Tool in Your Financial Plan
How to Calculate Your EXACT Early Retirement Number (Simple Formula)
How To Pay 0% Taxes On $120k+ Of Retirement Income
This Is What Financial Planning Really Changes
Why $1.5M Is Enough To Retire If You Want To Spend Like This
5 Expenses To Cut to Reach Financial Independence (and 3 NOT to)
Ready to Retire? Here's How to Tell Your Company │ Root Talks
The 4% Rule: Is It Still the Key to Early Retirement in 2025?
Here's 5 Portfolio Changes To Create More Income In Retirement
The Surprising Regrets of Wealthy Retirees | Root Talks
Why The Biggest Risk To Retiring Early Is Not What You Think
Avoid These 6 Common Mistakes When Retiring Early
Root Talks: Spend Your Way to a Happier Retirement: 5 Pillars of Better Spending
Why More People Are Retiring Early Today Than Ever Before
4 Tax Strategies To Consider This Year
Root Talks: How Does The Advisory Team Structure Work at Root?
Why It's Natural To Be Worried To Retire (And What To Do About It)
Healthcare Analysis: How We Save Our Clients Thousands Before Medicare Begins
Root Talks: How to Get Past the Fear of Retiring Even When You Have Enough
How Much Should I Have In Bonds/Cash/etc. In Retirement?
My Biggest Recommendation Before You Retire - Please Do This
Root Talks: How We Plan When Markets Are Volatile
How To Instill Financial Values In Children
The One Reason Everyone Delays Their Retirement
How To Plan For Big One-Time Expenses Before You Retire
Behind The Scenes At Root: How Do We Select Our Advisors?
How To Remove "Headtrash" and Spend In Retirement Without Worrying
5 Questions To Ask When Interviewing A Financial Advisor
Retire in Style: The 4 States That Offer the Best Bang for Your Buck
Retirement Planning With Guaranteed Income (Pension, Social Security, Rental Income, etc.)
Step-by-Step Guide To Withdrawing Retirement Income
The True Value Of A Debt-Free Retirement (Should I Pay Off My Mortgage?)
How Does Root Differ From Traditional Financial Firms?
How Do We Build The Best Team In The Financial Industry?
Root's New Community Is Coming! (EXCITING UPDATE)
How Much Should I Be Saving To Retire Early?
A Complete Guide To Long-Term Care
You Don't Need A Tax Preparer. You Need A Tax Planner.
Here's How To Live A Retirement Without Anxiety
How Many Investment Firms Should I Split My Money Between?
Behind The Scenes At Root: A Deep Dive Into Our Business
7 Steps To Check Off Before Retiring Early
How Much Do I Need To Spend $10k/Month In Retirement? Hint: LESS THAN YOU THINK!
You Won't Believe How This Couple Retired Early With $500k+
Here's How To Decide When To Turn On Social Security
How Do I Invest To Create The Most Income In Retirement?
How Do I Know When I Can Retire Early (Not Work Forever)?
Here's Why You Shouldn't Worry Regardless Of Who Is In Office
How Ari & James Met - Here's How Root Was Founded
3 Easy Steps For Happiness In Retirement
STOP! Consider THIS Before Doing a Roth Conversion
8 Tax Strategies To Consider Before Year-End
This Is The Danger Of Working One More Year: Goalpost Planning
5 Reasons You Should Not Buy An Annuity (And When To Surrender One You Have)
How To Discuss Inheritance With Your Parents (with James)
5 Fun Activities Often Overlooked In Retirement
Special Announcement - NEW SHOW!
How Much Do I Need To Spend $25k/Month In Retirement?
Run This Test BEFORE You Retire Early (How To Avoid Getting UNLUCKY)
3 Common Mistakes People Forget When Retiring Early
Do You Know How Much You Are Paying Your Advisor?
Here's How To Pay 0% In Taxes (ZERO Capital Gains)
3 Tips To Retire On Your Own Terms
Pension Decision - Lump Sum or Annuity?
Celebrating 200 EPISODES (SPECIAL EPISODE) - The History & Future Of The Show!
Don't Do Any Roth Conversions Before You Ask Yourself THIS
5 Ways An Advisor Can Change Your Retirement
The Complete Guide To Optimizing Healthcare Costs Before 65
The Complete Guide To Implementing Roth Conversions: Tax Strategy
Here's How To View Real Estate As Part Of Your Retirement Strategy
7 Surprising Regrets From My Clients Who Retired Early
5 Signs It’s Time To Consider Retiring Early
5 Easy Ways To Know If You Should Do Roth Conversions
How Do We Build Multi-Generational Wealth? [Estate Planning]
3 Retirement Rules Of Thumb That Don't Apply To An Early Retirement
My Story | Why Do I Do This?
Where Should I Withdraw Money From First In Retirement?
How To Manage Cash Flow Before & Throughout Retirement
A Real-Life Story Of Investing Too Well For Retirement
Here’s How To Determine If You Should Keep Or Break Up With Your Advisor
How To Create An Anti-Cookie Cutter Investment Portfolio
How Much Should I Be Saving To Retire Early?
A Complete Guide To Inheriting Money (Tax Planning)
4 Steps To Determine When You Can Retire Early
Understanding Early Withdrawal Strategies: Rule of 55, SEPP, etc.
How To Compare Roth Conversions v. ACA Subsidy Planning When Retiring Early
5 Steps To Navigating Health Insurance When Retiring Before Age 65
3 Regrets From My Clients Who Retired Early
3 Classic Early Retirement Mistakes To Avoid
5 Situations When It Does NOT Make Sense To Implement Roth Conversions
Do We Have Enough To Retire (And Never Go Back To Work)?
The 2 Portfolio Withdrawal Mistakes To Avoid If Retiring Before Age 65
This Is The Mindset Shift Needed To Retire Early With CONFIDENCE!
How To Protect Against Retiring, Getting Unlucky and Having To Work Again
A Complete Guide To Roth v. Pre-tax (Early Retirement Pro Tips)
Why Most People Pick The Wrong Asset Allocation For An Early Retirement
"I retired early and didn't start seriously investing until my 40s" - Special Episode With My Clients!
Here's How Social Security Gets Impacted When Retiring Early
This Is How To Retire Early Without Worrying About Running Out Of Money
5 Easy Steps To Know If You're On Track To Retire Early
3 Situations When Retiring Early Will Make More Financial Sense Than Continuing To Work
(10 MISTAKES) When Retiring Early...
5 Tips From My Clients Who Retired Early Successfully
The 3 Levels Of An Early Retirement | What Level Are YOU At?
7 Things To Optimize Your Finances Before Year-End (Checklist)
4 Simple Tips To Retire Early
How Much Do You Need To Be Able To Spend $10k/month?
When Does It Actually Make Sense To Hire A Financial Advisor?
The Tax-Efficient Way To Simplify Your Retirement
[Client Story] Why You Should Consider Retiring Earlier Than Planned
Why You Should Consider Renting In Retirement
How Much Is "Enough" To Retire Early?
[Client Story] - How To Remove Your Saving Mindset For REAL Success In Retirement
Pension FAQ: How To Determine If You Should Elect Lump Sum or Annuity
Please Ask Yourself This One Question Before You Actually Retire Early
Don't Die The Richest Person At Your Funeral with Dr. Donatello
Balancing Emotion and Finance: The Impact of Investing Well For Retirement
How To Avoid Having A GOOD Financial Plan And BAD Early Retirement
How To Diversify One Stock With Massive Gains (Tax Tip)
An Advanced Guide To Minimizing Future RMDs
Case Study Announcement: Early Retirement (YouTube ONLY)
How Much Safe Money Do I Need On Hand Once I'm Retired?
I'm 60 with $2M. Should I Prioritize Roth Conversions or Healthcare Subsidies?
The Complete Guide To Minimizing Taxes With An Early Retirement
3 Tips For A Successful Early Retirement (Story)
A Complete Guide To Insurance Protection (What You Need and DON'T Need)
Why You Should Consider To STOP Saving For Retirement *(not a typo)
5 Tips So You Only Retire Early ONCE!
5 Tips To Maximize Your Roth IRA (Pro Tips To Retire Early)
How To Increase Returns With Strategic Asset Location (And What To Avoid)
How to Create a Holistic Financial Strategy
What To Do With Your 401(k) Once You Retire / Leave Employment?
5 Reasons To Consider Retiring EARLY Today (from my clients)
How To Balance Health & Wealth For An Early Retirement (Special Guest)
Deferred Comp: How To Maximize Retirement Savings & Pay Less Taxes
Announcement: NEW eBook is live! Health Insurance for An Early Retirement
30+ Reasons To Retire Early (as if you needed more..)
3 Rules Of Thumb To Avoid If You Want To Retire Early (& 3 To Follow)!
"Should I Do Pre-Tax or Roth If I'm In A High Tax Bracket?"
4 Hidden Fees Inside Your 401(k) - How To Plan With Your 401(k) Well
To Roth Conversion or To NOT Roth Conversion..
3 Habits To Avoid When Considering An Early Retirement
5 Misconceptions About Retiring Early To Please AVOID
Should You Self-Insure or Buy Long-Term Care Insurance?
How To Invest Your "Bridge" Account To Retire Early Like A Pro
5 Strategies To Reduce Required Minimum Distributions
How To Make Sure Your Money Is Safe
How Much Money Is Needed To Retire Early?
Should I Pay Off My Mortgage Early or Invest?
*EXTRA Episode* - 10 Minutes for the Next 50 Years Of Retirement (Story)
3 Tips On Perspective When Investing To Retire Early
How To Create The Perfect Asset Allocation
How To Plan When There Is A Significant Age Gap Between Spouses
5 Tips From My Wealthiest Clients On How They Retired Early
How To Pay Less Taxes (or 0%): Tax-Gain Harvesting v. Roth Conversions
Quick Tax Tips To Reduce IRMAA Surcharges & The Impact On Roth Conversions
A Beginner's Guide To Real Estate Investing In Retirement (Worth It?)
Top 5 Options for Health Insurance If You Retire Early
3 Tips To Retire Early And Not Run Out of Money
A Complete Guide To A Successful Retirement (Client Stories)
8 Key Considerations in 2023 (and what to AVOID)
7 Tips To Optimize Your Money Before Year-End (Checklist)
How To Avoid The #1 Retirement Mistake & Create True Financial Freedom
How You Can Maximize Retirement Income Before 59.5 (don't pay extra taxes and penalties)!
A Complete Guide To Tax Savings With Charitable Giving (HUGE Tax Deduction)
How Much "Safe" Money Do You Need At All Times?
How To Build A Customized All-Weather Investment Portfolio
Top 5 Retirement Mistakes To Avoid (From My Clients)!
Everything You Need To Know To Retire Before Age 65
How To Use Your IRA To Take Advantage Of This Market Downturn
Top 3 Early Retirement Myths (Don't Spend Time/Energy Thinking About These)
3 Ways To Create Tax-Free Income (Yes, 0% Taxes)
This Is Why You Shouldn't Only Own The S&P 500 Index
What No One Tells You About Creating Financial Freedom
How To Know When To Stop Working
Where To Pull Income From When You Retire Early
5 Most Important Parts Of A Successful Financial Plan
When You Should & Should NOT Hire A Financial Advisor
How To Determine How Much You Want To Spend In Retirement
5 Tips To Prepare for Retirement (While You're Working)
Why Should You Consider An Early Retirement? A Real-Life Story
Retirement 101 - What Are The Primary Issues To Consider Before I Retire?
Retire Sooner - How To Know When You Should Stop Working
The #1 Retirement Secret - When To Stop Saving For Retirement
Retirement Activities - The Most Fulfilling Activities For a Meaningful Retirement
Retirement Planning with Roth IRAs - The Amazing Benefits of Roth IRAs in Retirement
Social Security Benefits - How To Optimize Your Retirement Income
A Complete Guide To Surviving Bear Markets
Special Announcement - I'm Featured on the Ready for Retirement Podcast!
Retirement Tax Planning - 5 Tax Opportunities To Consider Every Year
Personal Finance in Retirement - How To Maximize Your Retirement Finances
Retirement Accounts - 401(k) v. Roth 401(k) - What's Better For Your Situation?
Retirement Portfolio - Why & How You Should Rebalance Your Portfolio
5 Things I Wish I Knew About Money When I Was Younger
Retirement Projections - Don't Depend On A Monte Carlo Analysis To Retire
Retirement Income - How To Optimize Your Finances In Retirement
Financial Freedom - How Much Money Do You Need To Be "Money Free"?
Bear Markets in Retirement - A New Way To Think About Market Downturns
Retirement Investing - 5 Tips To Know
Early Retirement - 3 Key Rules To Retire Early
Retirement Annuities: Should I Buy An Annuity For Guaranteed Income?
Investing Strategy Tip - Should I Just Buy & Hold My Investments?
Retirement Goals - How To Prioritize Your Financial Goals
Tax Planning In Retirement - How To Save On Taxes
Roth Conversions Before Retiring: The Secret To Minimizing Your Taxes
Retirement Tips - 5 Tips To Retire Early
Investing Tips - A Complete Guide To Investing in Retirement
Retirement Investing - Should I Own Cryptocurrency In My Retirement Portfolio?
How I Invest My Own Money
How Much Cash Do I Need On Hand?
5 Tips To Become Financially Free
Where Should I Save For A Down Payment?
Should I Be In A 100% Stock Portfolio?
When Should I Hire A Financial Planner?
How To Beat Inflation
4 Tips For Young Investors
When Should I Buy A Home?
The Ultimate Investor Cheat Sheet (Lessons & Stories)
4 Easy Ways To Save On Taxes
Why I Love Roth IRAs
Should I Pay Off My Mortgage or Invest?
When Do I Need Life Insurance?
10 Things You Shouldn't Focus On (Financially)
The Most Important Investment Decision You'll Likely Ever Make
Should I Invest All At Once or Periodically?
The 3 Levels of Wealth
If You're Still Worried, You Aren't Wealthy
Is The Stock Market Overvalued? (And Why You Don't Need To Worry)
NFTs (Non-Fungible Tokens): How They Work & Should You Buy One?
I Just Received $100k, What Should I Do?
How Does The Stock Market Work?
What Are Capital Gains? (And How To Keep More Of What You Make)
Should I Hire A Financial Planner?
How To View Your Taxes If You’re Self-Employed
When Should I Start Saving For Retirement?
Should I Just Invest In The S&P 500 Index?
15 Year v. 30 Year Mortgage - Which Should I Do?
Should I Invest In Bitcoin?
Solo 401(k) v. SEP IRA: Which Is Best For Small Business Owners?
How Risky Is The Stock Market?
How Much Cash Is Too Much Cash?
Professional Athletes: Here's How To Manage Your Finances
Should I Invest In Individual Stocks?
Health Savings Account v. Flexible Savings Account
Should I Invest When Saving For A Home?
Employee Benefits (Part 2): Important Questions to ask HR Dept.
Employee Benefits (Part 1): Investment Questions to ask your HR Dept.
401(k) v. Roth 401(k): Which Should I Use?
Earned Income v. Passive Income
Renting vs. Buying: What Should I Do?
10 Common Investment Questions Answered
Roth IRA Benefits for Graduate Medical Students
Tax-Loss Harvesting vs. Tax-Gain Harvesting
How To Make Your Money Work For You
The Power Of Saving $20/month
Roth IRA vs. Traditional IRA: Which Should I Use?
Good Debt vs. Bad Debt
What Is An Index Fund?
Stock Options: What Are They And How Do They Work?
Tax Basics: What School Didn't Teach You
Should I Invest In Real Estate?
How I Invest My Own Money
How To Save For A Big Purchase
How Do I Teach Kids About Money?
The Rule of 72
How To Start Taking Control Of Your Financial Future
The Pros & Cons of Investing
Introduction to Personal Finance Redefined