Jesse Cramer, founder of 'The Best Interest' blog and podcast, transitioned from aerospace engineering to financial planning, simplifying complex topics for his clients. He discusses essential strategies for pre and post-retirement planning, particularly for late starters. Jesse emphasizes the importance of financial literacy, tackling the emotional fears surrounding retirement, and the balance between conservative and aggressive investment styles. He uses gardening as a metaphor for diversification and nurturing personal relationships to achieve financial wellness.

Disha Spath, an internist and host of the Finding Financial Freedom podcast, shares her journey from financial struggle to frugality advocate. She discusses the crucial difference between being frugal and cheap, tackling the gender wage gap, and strategies for managing income disparities in relationships. Disha emphasizes the importance of value-based spending and wise investing, particularly for high-income professionals. With vivid anecdotes, she offers actionable advice on navigating financial realities while striving for independence and well-being.

In this engaging conversation, Andy Hill, an award-winning blogger and family finance coach, shares his inspiring journey from deep debt to achieving financial independence. He emphasizes the importance of teaching generosity to children through family traditions like 'the big give.' Andy explores how to cultivate a culture of giving while maintaining financial literacy at home. He also discusses the 'Coast FI' concept, highlighting the balance between personal fulfillment and long-term financial goals. Tune in for heartwarming insights that promote wealth, happiness, and a generous legacy.

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.   🔗Connect with us  Buy CUtFI a coffee  Record a message for CUtFI   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.

Christina Gawlik, a former math professor, sold all her possessions in 2019 for global adventures. She dives deep into geo-arbitrage and how she navigates finances on the go. Discover her creative income strategies and the importance of maintaining social connections while traveling. Christina sheds light on managing banking and healthcare as a nomad, sharing personal insights on the joys and challenges of her lifestyle. Tune in for inspiration on prioritizing experiences over possessions and achieving financial independence!

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.  🔗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 https://www.abundowealth.com ❌ DeleteMe: Your personal data is yours again http://joindeleteme.com/catchingup 🧑🏼‍🏫 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    🔗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 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 insightful discussion, Jeff York, known as the 'Wealthy Custodian,' teams up with HSA Maven Jackie to unfold the secrets of maximizing Health Savings Accounts. They dive into strategies for investing HSAs for long-term wealth, tackle misconceptions, and explain the benefits of transitioning from IRAs to HSAs. The duo also shares tips on using HSA funds for healthcare abroad, and how to navigate high deductible plans efficiently. Whether you’re a novice or looking to supercharge your financial strategy, their expertise will leave you ready to take action!

Krista Kim, a finance enthusiast with a knack for insightful case studies, and Ed Kim, who brings an immigrant perspective to financial planning, share their inspiring journey to financial independence. They discuss overcoming childhood hardships, the role of resilience in shaping their financial strategies, and their transition towards minimalism. The couple also emphasizes the importance of open conversations about financial struggles and the transformative power of community support, offering actionable advice for achieving stability and investment success.

Brian Page, a former award-winning teacher, now educates on financial literacy and relationships. He introduces the concept of 'money dates,' where couples engage in meaningful financial discussions, arguing that communication is key to successful partnerships. Page also highlights his innovative Marriage Toolkit, which offers practical strategies for managing finances in modern marriages, including navigating marriages in blended families and overcoming materialism. With real-life anecdotes and expert insights, he emphasizes financial transparency for a thriving relationship.