All Episodes

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