Our guest today is Jacqueline (Jack) Howard, head of Money Wellness at Ally Financial, a leading voice in financial health & wellness, and fierce change maker. We are thrilled to bring you this special episode recorded live from FinCon 2024 in Atlanta, GA! It's no secret that we love Ally and talk about them often on the podcast. From the high yield savings accounts to the cool buckets that are perfect for allocating your sinking funds, they're our favorite. But what really blew us away in this interview was Jack's money story and how it led to her incredible work as the face of financial wellness at Ally. 

Jack blends personal finance and psychology to help people achieve holistic financial well-being that helps shift their perspective on money. She shares more about Ally's newest community initiative, Money Roots, a free financial education program designed to help people uncover the 'why' behind their money behaviors. Jack also gets vulnerable with us as she shares her own resilient story of the loss of her mother as a young girl and winning her heroic battle against breast cancer. With her giving spirit, she proudly served as chair of the Making Strides Against Breast Cancer of Detroit in 2023 and 2024.

Special thanks to LLC Attorney for sponsoring the Podcast booth at FinCon 2024.

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Resources mentioned on the show:

🌐 Ally.com

Sign up for free Ally ‘Money Roots’ Virtual Workshop

5 steps to uncover your money story

Jack's appearance on the show 'Side Hustlers' (Episode 2)

Catching Up to FI Episode: Sinking Funds Are Sexy | Bill Yount & Becky Heptig | 003

Support Jack’s favorite charity: Making Strides Against Breast Cancer of Detroit (Search on 'Jacqueline Howard')

If you enjoyed this episode, please follow the show on your podcast player and leave us a rating or review. This helps others find the show and keeps us creating great content for you!

Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Karsten Jeske also known as “Big ERN” is the founder and genius behind Early Retirement Now. He writes on all topics related to personal finance but is best known for his comprehensive series on safe withdrawal strategies.  In this episode he dives deep into the intricacies of safe withdrawal rates, sequence of return risk, the importance of market valuations for retirees and the 'one more year' syndrome often discussed in the Financial Independence community. Karsten also shares his personal journey from a modest upbringing in Germany to early retirement in the U.S.

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Resources mentioned on the show:

🌐 Early Retirement Now

The Safe Withdrawal Rate Series

Ten things the “Makers” of the 4% Rule don’t want you to know (SWR Series Part 26)

Karsten on Two Sides of FI YouTube

 If you enjoyed this episode, please follow the show on your podcast player and leave us a rating or review. This helps others find the show and keeps us creating great content for you!

Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

In this episode, Jesse Cramer discusses the essential considerations for pre and post-retirement planning and the major factors late starters should consider. Jesse is founder of the award winning 'The Best Interest' blog and podcast. He left a career as a mechanical and aerospace engineer to work with clients at a fiduciary, fee-only financial planning firm. Now, he uses those valuable engineering skills to simplify the most complex financial topics into fun explanations for his clients and his audience. 

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 Boomer Benefits: The nation’s leading family-owned Medicare brokers

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Resources mentioned on the show:

🌐 Best Interest Blog

Best Interest Podcast

Blog Post: The Market Reacts to An Assassination Attempt

Blog Post: It’s Not Too Late: 6 Finance Tips for Older Beginners

Blog Post:  NVIDIA’s Day in the Sun(flower)

Social Security Made Simple | Mike Piper | 054

Open Social Security calculator

Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

By day, Dr. Disha Spath is an internist caring for her patient’s physical and mental health.  By night, my she's known as The Frugal Physician and hosts the Finding Financial Freedom podcast. In this episode, Disha shares her personal journey from financial struggles to becoming an advocate for frugality and financial independence. She also discusses the differences between frugal and cheap, the gender wage gap, and strategies to manage income disparities in relationships. 

*Trigger warning: There are brief mentions of suicide in this episode.

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 Boomer Benefits: The nation’s leading family-owned Medicare brokers

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Resources mentioned on the show: (As an Amazon Associate, I earn from qualifying purchases.)

🌐 The Frugal Physician

Finding Financial Freedom Podcast

SPIVA® U.S. Scorecard, Year-End 2023, S&P Dow Jones Indices 

“The Loser’s Game” by Charles D. Ellis, Financial Analysts Journal, Jan/Feb, 1995

“Why Lifestyle Creep is Mostly a Myth” by Nick Maggiulli, Of Dollars And Data, July 23,2024

“She makes $550K a year. Her husband makes $60K.  Here is how it affects her relationship”, July 25, 2024, CNBC

Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Andy Hill is an award-winning blogger, podcaster, Youtuber and family finance coach. All under the brand of 'Marriage, Kids, and Money’, his primary focus is helping families build wealth and happiness. He shares his inspiring story of going from a $50,000 negative net worth to achieving financial independence and now living his best 'Coast FI' life with his family. Andy also shares how he is creating a meaningful legacy of giving and generosity with his kids.

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 Boomer Benefits: The nation’s leading family-owned Medicare brokers https://boomerbenefits.com/catchingup/ 

 DeleteMe: Your personal data is yours again. Hands-free subscription service that removes you from data broker sites. Enter the code Catchingup at checkout to get 20% off  http://joindeleteme.com/catchingup

Resources mentioned on the show: (As an Amazon Associate, I earn from qualifying purchases.)

🌐 Marriage, Kids, and Money Website https://www.marriagekidsandmoney.com

YouTube https://www.youtube.com/@MarriageKidsandMoney

Instagram http://instagram.com/marriagekidsandmoney

Podcast https://marriagekidsandmoney.com/podcast-archive/

Coast FIRE Number: What Is It And How To Calculate It https://marriagekidsandmoney.com/coast-fire-number/ 

Charities for Children: 12 Organizations Giving Kids a Better Chance at Life https://marriagekidsandmoney.com/top-charities-for-children/

An Alternative to 10% Giving for the Modern Family https://marriagekidsandmoney.com/podcast/alternative-to-10-percent-giving/

🕒 Timestamps/Chapters:

00:00 The Financial Wake-Up Call

00:41 Discovering the Debt-Free Movements 

02:25 Introduction to Andy Hill

06:18 Andy Hill's Financial Journey

13:37 The House Blunders and Lessons Learned

17:31 The Psychological Benefits of Being Mortgage-Free

28:02 Understanding Coast FI

31:47 Understanding Coast FI

33:16 Personal Journey to Coast FI

33:41 Balancing Work and Life

35:22 Marriage Counseling and Career Shift

38:38 Transition to Financial Coaching

42:40 Generational Wealth and Giving

44:33 Teaching Kids About Money and Generosity

53:17 Family Traditions and Generosity

55:25 Final Thoughts and Reflections

Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

This episode explores the intricate and confusing world of Medicare with leading expert Danielle Roberts. Danielle is founding partner at Boomer Benefits, an agency that has helped thousands of ordinary Americans learn and navigate their entry into Medicare since 2005. She's also author of the bestselling book '10 Costly Medicare Mistakes You Can't Afford to Make'. Danielle breaks through the confusion and explains Medicare's history, enrollment rules, Parts A, B, C, and D, and the differences between Medigap and Medicare Advantage plans. Discover the importance of early planning, common pitfalls to avoid, and critical decisions about Medicare coverage.

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Thank you to our sponsors:

Boomer Benefits: The nation’s leading family-owned Medicare brokers https://boomerbenefits.com/catchingup/ 

DeleteMe: Your personal data is yours again. Hands-free subscription service that removes you from data broker sites. Enter the code Catchingup at checkout to get 20% off  http://joindeleteme.com/catchingup

Resources mentioned on the show: (As an Amazon Associate, I earn from qualifying purchases.)

🌐 Boomer Benefits Website: https://boomerbenefits.com 

Boomer Benefits YouTube Channel:  https://youtube.com/@boomerbenefits

Boomer Benefits Facebook Group: https://m.facebook.com/groups/BoomerBenefits/

📗 10 Costly Medicare Mistakes You Can't Afford to Make: https://amzn.to/3BLdL1b

Catching Up to FI Health Savings Account Episode Part 1, Episode 98:  https://www.youtube.com/watch?v=8vaUH8UfPTQ&t=3629s  

Catching Up to FI Health Savings Account Episode Part 2, Episode 99:  https://www.youtube.com/watch?v=36S67X4s4pc&t=8s  

🕒 Timestamps/Chapters:

00:00 Introduction to Medicare Planning

00:25 Common Medicare Mistakes

01:28 Welcome to Catching Up to FI

02:04 Shoutouts and Acknowledgements

03:31 Introducing Danielle Roberts

05:31 History and Evolution of Medicare

07:59 Medicare Eligibility and Enrollment

10:55 Understanding Medicare Parts A and B

18:40 Medicare Part D: Drug Coverage

27:24 Medigap Plans Explained

36:56 Medicare Advantage Plans

42:17 Understanding Medigap and Medicare Advantage Plans

44:00 Cost Savings with Medicare Advantage

45:21 Tips for Medicare Advantage Plan Holders

46:57 Using HSA Dollars for Medicare Premiums

50:56 Common Medicare Mistakes to Avoid

01:08:22 The Importance of Reviewing Your Coverage Annually

01:12:19 Final Thoughts and Future of Medicare

Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Cris Gawlik sold all her possessions in 2019 to travel the world, and in this episode she shares her fascinating nomadic journey. Learn how she utilizes geo-arbitrage, manages her finances on the go, and maintains strong social connections across the globe. She gives us insights into how she handles banking, health insurance, and taxes while living internationally. This conversation provides a comprehensive guide for those considering a similar path to financial independence. Get inspired by her creative approach to generating income and the community she finds along her adventurous journey.

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DeleteMe: Your personal data is yours again

Hands-free subscription service that removes you from data broker sites. Enter the code Catchingup at checkout to get 20% off:  http://joindeleteme.com/catchingup

Resources mentioned on the show: (As an Amazon Associate, I earn from qualifying purchases.)

Website

https://christinagawlik.wixsite.com/asuitcaseandasmile

Facebook

https://www.facebook.com/asuitcaseandasmile

Linktree

https://linktr.ee/ChristinaGawlik

IRS Foreign earned income exclusion

https://www.irs.gov/individuals/international-taxpayers/foreign-earned-income-exclusion

🕒 Timestamps/Chapters:

00:00 Why I Chose to Leave the U.S.

00:38 Designing a Life Abroad

02:18 Welcome to Catching Up to FI

03:19 Introducing Dr. Christina Gawlik

04:34 Chris's Nomadic Lifestyle

08:01 Early Life and Influences

13:47 Financial Missteps and Lessons Learned

22:03 Transition to a Nomadic Life

32:31 Building a Business on the Road40:10 Creative Job Hunting Strategies

41:29 Navigating Logistics as a Digital Nomad

41:52 Banking Tips for Global Travelers

46:16 Overcoming Language Barriers

48:16 Health Insurance and Medical Care Abroad

57:48 Handling Taxes as an Expat

59:32 Social Life and Loneliness

01:02:50 Impact of COVID-19 on Nomadic Life

01:06:12 Future Plans and Reflections

Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

Subscribe and Watch on YouTube

Join host Bill and guest Diana Falck as they explore the intersection of community resilience and getting involved. In the wake of a recent crisis in Western North Carolina and East Tennessee, the duo highlights local relief efforts and community collaboration. Then in this special 100th episode, we get back to the basics with a step-by-step guide for late starters on the path to financial independence. Our guest for this special episode is original Catching Up to FI co-host, Becky Heptig! She joins Bill and Jackie as they share insights and guide you through how to get on track with your finances. They not only share what to do but in what order. It’s hard starting late and feeling like you’ve done everything wrong. The good news is, there is time to catch up and this is the place to start.

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💵 Abundo Wealth: Advice-Only Financial Planning for Everyone https://www.abundowealth.com

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🧑🏼‍🏫 Personal Finance Club (Use code CUTOFI to get $30 OFF) PFC courses https://courses.personalfinanceclub.com/?ref=0114d0 or PFC investing course only https://courses.personalfinanceclub.com/courses/build-wealth-by-investing-in-index-funds?ref=0114d0

🍑 Nectarine: Advice-Only Financial Advisors https://hellonectarine.com/r/cutfi (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)

🏦 Boston Institute of Finance Personal Growth Track: Enter code catchingup to get 5% off any “Personal Growth Track” course or package http://www.bostonifi.com/personal-growth

Resources mentioned on the show: (As an Amazon Associate, I earn from qualifying purchases.)

Red Cross: Donate 

Episodes:

Retiring Before Mom & Dad | Rob Berger | 25

A Hero’s Journey: The Mother of All Case Studies! | Krista and Ed Kim | 97 

Enoughness: Your Life or Your Money | Vicki Robin | 95

Doña Quixote, Life Energy, and The Coming of Aging | Vicki Robin | 94 

Catch-Up Contributions

📗Your Money or Your Life: 9 Steps to Transforming Your Relationship with Money and Achieving Financial Independence

Shocking Simple Math Behind Early Retirement ~Mr. Money Mustache

The Simple Path to Wealth: Your Road Map to Financial Independence and a Rich, Free Life ~JL Collins

Ally High Yield Savings Account (4% as of 10/4/24 + $100 Bonus with direct deposit-by 12/31/22024)

Personal Finance Club - example for late starters:  https://www.personalfinanceclub.com/is-it-too-late-to-start-to-investing

The Ultimate Investing Checklist: https://www.personalfinanceclub.com/the-ultimate-investing-checklist

Ground Rules according to the Money Guys 2/1/24: https://moneyguy.com/article/foo

🕒 Timestamps/Chapters:

00:00 Call to Action: How You Can Help in the Disaster in North Carolina and Tennessee

05:28 Introduction

07:50 Celebrating 100 Episodes with Becky Heptig

10:52 Why People Get a Late Start in Financial Independence 17:16 Disadvantages of a Late Start

25:26 Advantages of a Late Start

38:01 Financial Order of Operations for Late Starters

44:57 Eliminating Debt: The First Step to Financial Freedom

45:57 Big Picture Wealth Building Strategies

47:27 Calculating Your Net Worth and FI Number 

49:32 Increasing Income and Reducing Expenses

51:06 Playing Defense: Insurance and Protection

54:51 Offensive Strategies: Emergency Funds and Employer Matches

01:01:35 Investing Wisely: Roth IRAs, HSAs, and More

01:06:15 Risk Tolerance and Rebalancing Your Portfolio

01:10:02 Maximizing Employer Plans and Mid-Range Debts

01:12:55 Hyperaccumulation and Taxable Brokerage Accounts

01:16:06 Prepaying Future Expenses and College Funding

01:22:57 Reevaluating and Automating Your Financial Plan

01:27:09 Final Thoughts and Encouragement

🎧 Listen & Subscribe: Don't forget to subscribe to "Catching Up to FI" for more insightful episodes. Tap the bell icon 🔔 to get notified of new episodes!

✍🏻 Leave a Comment: Share your thoughts or experiences in the comments below. Have questions for our guests or the hosts? Drop them here, and we’ll get back to you!

👍🏻👍🏿 Like, Share, and Subscribe: If you enjoyed this episode, please like, share, and subscribe! Your support helps us bring more valuable content to you.

Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

In the second episode of this special two-part series we continue with our deep dive conversation about Health Savings Accounts (HSAs) with Bill and Jackie, and guest co-host, Jeff York (also known as the Wealthy Custodian from episode 74 & 76). We break down in-depth scenarios, including unique contribution rules for domestic partners and adult children, investment strategies, drawdown plans and estate planning considerations. We answer listener questions and share our wish list for HSAs in the future.

For this episode we are providing a formal presentation here:

PDF of Full HSA Presentation 

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Thank you to our sponsors:

 Abundo Wealth: Advice-Only Financial Planning for Everyone

 DeleteMe: Your personal data is yours again

Personal Finance Club: Use code CUTOFI to get $30 OFF any course or PFC investing course only

Nectarine: Advice-Only Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)

 Boston Institute of Finance Personal Growth Track: Enter code catchingup to get 5% off any “Personal Growth Track” course or package

Resources mentioned on the show: (As an Amazon Associate, I earn from qualifying purchases.)

HSA Rules and Regulations (IRS Pub#969)

Qualified Medical/Dental/Vision Expenses (IRS Pub#502)

Preventive Care and Chronic Conditions (IRS Notice)

Morningstar / Best HSA Providers 

Kitces / HSA ‘Deathbed Drawdown’

Fidelity / HSA Education 

 Wex Health / HDHP with HSA vs. traditional health plan calculator

Consumer Friendly List of HSA-Eligible expenses

🕒 Time stamps:

00:00 Introduction to HSA Series Part Two

00:23 Maximizing HSA Contributions for Families

02:34 Drawdown Strategies for Health Savings Accounts

06:59 Planning for HSA Beneficiaries

14:55 Case Study: Domestic Partners and HSA Contributions

20:06 Q&A Session: HSA Myths, Tips, and Tricks

28:17 Evaluating HSA Options for Chronic Conditions

28:53 Financial Considerations for High Deductible Plans

29:54 Using Calculators to Compare Health Plans

31:25 HSA Contributions and Family Plans

33:18 Maximizing HSA Benefits and Investment Strategies

43:54 Legislative Changes and Future of HSAs

47:57 HSAs for Late Starters in Financial Independence

53:01 Conclusion and Final Thoughts

Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

In this special two-part episode we unveil the 'Wealthy Custodian,' Jeff York (from episode 74 & 76), and take a deep dive into the world of Health Savings Accounts (HSAs). Jeff joins as co-host along with Bill and Jackie (our HSA Maven) to share how they supersized thier HSAs and discovered how powerful they can be on the path to FI. This comprehensive series starts with Part 1 where we explore tips, tricks, and common misconceptions about HSAs and tackle little known strategies that are rarely discussed. We'll also talk about who should consider a high deductible plan, eligible expenses, bright ideas like using your HSA for health expenses abroad, and even IRA to HSA transfers. Whether you are new to HSAs or looking to maximize your FI strategy, you won't want to miss this episode. Stay tuned for Part 2 where we explore HSA drawdown strategies, advanced scenarios and answer listener questions!

For this episode we are providing a formal presentation here:

PDF of Full HSA Presentation 

🔗Connect with us

 Buy CUtFI a coffee

 Record a message for CUtFI

Thank you to our sponsors:

 Abundo Wealth: Advice-Only Financial Planning for Everyone

 DeleteMe: Your personal data is yours again

Personal Finance Club: Use code CUTOFI to get $30 OFF any course or PFC investing course only

Nectarine: Advice-Only Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)

 Boston Institute of Finance Personal Growth Track: Enter code catchingup to get 5% off any “Personal Growth Track” course or package

Resources mentioned on the show: (As an Amazon Associate, I earn from qualifying purchases.)

HSA Rules and Regulations (IRS Pub#969)

Qualified Medical/Dental/Vision Expenses (IRS Pub#502)

Preventive Care and Chronic Conditions (IRS Notice)

Morningstar / Best HSA Providers 

Kitces / HSA ‘Deathbed Drawdown’

Fidelity / HSA Education 

 Wex Health / HDHP with HSA vs. traditional health plan calculator

Consumer Friendly List of HSA-Eligible expenses

🕒 Time stamps:

00:00 Introduction to the Special Episode

00:07 Unveiling the Wealthy Custodian

00:33 Diving into HSAs: Tips, Tricks, and Misnomers

03:00 Personal HSA Journeys

13:09 Understanding High Deductible Plans

25:02 Flexible Spending Accounts vs. Health Savings Accounts

28:11 HSA Eligibility and Contribution Limits

34:09 State-Specific HSA Tax Rules

37:58 Unique Provisions for Different States

38:10 Understanding the Last Month Rule

40:09 HSA Eligible Expenses

41:48 Supersizing Your HSA

42:27 Investment Strategies for HSA

44:50 Maximizing Contributions and Advanced Strategies

47:20 Reimbursement Strategies and Record Keeping

52:40 IRA to HSA Conversions

01:02:16 Bright Ideas for HSA Usage

01:09:21 Using HSA Funds Abroad

01:11:30 Conclusion and Final Thoughts

Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions. 

This heartfelt episode dives into the incredible story of Krista and Ed. From growing up in poverty to facing financial insecurity as adults, this resilient couple shares their journey of overcoming adversity and finding hope in the FIRE movement. Discover how a deep bond of love, open communication, strategic planning, and an unwavering spirit led them to financial independence. Learn about their pivotal experiences, including a live case study at the EconoMe conference and actionable tips that can help you on your financial journey. Don’t miss their powerful message of never giving up and transforming your dreams into reality.

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Thank you to our sponsors:

 Abundo Wealth: Advice-Only Financial Planning for Everyone

 DeleteMe: Your personal data is yours again

Personal Finance Club: Use code CUTOFI to get $30 OFF any course or PFC investing course only

Nectarine: Advice-Only Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)

 Boston Institute of Finance Personal Growth Track: Enter code catchingup to get 5% off any “Personal Growth Track” course or package

EconoMe Case Study: Real Life Numbers

🕒 Time stamps:      

00:00 A Childhood of Hardship and Resilience

02:11 Introduction to the Case Study

02:27 Meet Krista and Ed

03:03 The Financial Journey Begins

06:37 Krista's Reading Habit

08:11 Ed's Gaming Passion

08:45 Ed's Immigrant Upbringing

15:00 Krista's Struggles and Triumphs

25:44 The Debt Story Unfolds

36:56 Exploring Contentment and Consumerism

37:16 Discovering the FI Movement

39:09 Joining the ChooseFI Community

41:32 Applying for the EconoMe Case Study

42:49 Sharing Financial Details Publicly

45:53 Case Study Insights and Learnings

47:22 Financial Goals and Planning

52:57 Budgeting and Debt Management

01:03:59 Investment Strategies and Risk Tolerance

01:07:25 Final Thoughts and Advice for Late Starters