Mind Blowing ways to Maximize Your Health Savings Account (HSA) | Jeff York | 98
Catching Up to FI: Financial Independence for Late Starters
Release Date: 09/29/2024
Sequence of Returns Risk: What Every Retiree Needs to Know | Karsten Jeske | 106
Catching Up to FI: Financial Independence for Late Starters
Karsten Jeske also known as “Big ERN” is the founder and genius behind . He writes on all topics related to personal finance but is best known for his comprehensive . 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. 🔗 Thank you to our sponsor: ...
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Space Telescopes, Sunflowers, and Financial Gardening | Jesse Cramer | 105
Catching Up to FI: Financial Independence for Late Starters
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. 🔗 Thank you to our sponsors: ...
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Tennis and the Stock Market: Winning the Loser's Game | Disha Spath | 104
Catching Up to FI: Financial Independence for Late Starters
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. 🔗 Thank...
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Generosity and Smart Spending: A Family Affair | Andy Hill | 103
Catching Up to FI: Financial Independence for Late Starters
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. 🔗 Thank you to our sponsors: Boomer Benefits: The nation’s leading family-owned Medicare...
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Beyond the Alphabet Soup: Expert Tips for Mastering Medicare & Avoiding Pitfalls | Danielle Roberts | 102
Catching Up to FI: Financial Independence for Late Starters
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...
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Wanderlust and Wealth: A Nomadic Guide to FI | Cris Gawlik | 101
Catching Up to FI: Financial Independence for Late Starters
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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From Zero to Hero: A Late Starter’s Guide to the Galaxy | Becky Heptig | 100
Catching Up to FI: Financial Independence for Late Starters
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...
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Maximizing HSAs Part 2: Devising Drawdowns, Badass Scenarios & Listener Questions | Jeff York | 99
Catching Up to FI: Financial Independence for Late Starters
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 & ). 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: ...
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Mind Blowing ways to Maximize Your Health Savings Account (HSA) | Jeff York | 98
Catching Up to FI: Financial Independence for Late Starters
In this special two-part episode we unveil the 'Wealthy Custodian,' Jeff York (from episode & ), 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,...
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A Hero’s Journey: Krista & Ed, The Mother of All Case Studies! | Krista and Ed Kim | 97
Catching Up to FI: Financial Independence for Late Starters
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...
info_outlineIn 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:
Thank you to our sponsors:
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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’
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.