I dive into the Southwest Companion Pass, a travel hack I’m currently using that offers huge savings for frequent travelers. The pass allows you to bring a companion along on any Southwest flight for just the cost of taxes, making it an incredible deal if you often fly with someone. To earn the pass, you need 135,000 qualifying points, which can be done efficiently through Southwest credit cards and carefully timing your spending to hit signup bonuses early in the year. I stress the importance of tracking expenses diligently to maximize the two-year eligibility period, ensuring you get the most value out of the pass. For me, the potential savings—$4,000 to $6,000 in travel value over two years—makes this a no-brainer, especially if you’re a responsible credit card user or a business owner. I also share tips for maintaining the pass long-term, like alternating eligibility with a spouse. If you fly Southwest frequently, this is an easy way to make your travel budget go much further.

Key Takeaways:

• The Companion Pass allows you to bring a companion on any Southwest flight for just the cost of taxes.

• Earning the pass early in the calendar year maximizes its value because it’s valid for the rest of that year and the entire following year. Aim to hit qualifying thresholds in January.

• The strategy only works if you pay off balances in full each month to avoid interest. Carrying debt undermines the benefits of the Companion Pass.

• You can requalify for the pass after 24 months by canceling your Southwest cards and reapplying. Many couples alternate who earns the pass to extend the benefit indefinitely.

• This hack is especially valuable for frequent travelers, those who live near Southwest hubs, and business owners or side giggers who can easily meet spending requirements.

Key Timestamps:

(00:00) - Introduction and Personal Hack

(00:25) - Understanding the Southwest Companion Pass

(01:29) - Steps to Earn the Companion Pass

(07:03) - Maximizing the Companion Pass Benefits

(10:28) - Conclusion and Final Thoughts

(11:28) - Additional Resources and Farewell

Key Topics Discussed:

BLUF Veteran Finance Podcast, Military Finance, Veteran Financial Planning, Military Money Management, VA Benefits, Military Retirement Planning, Financial Literacy for Soldiers, Military Budgeting Tips, Debt Management for Service Members, VA Loans, Military Investment Strategies, Saving for Deployment, Thrift Savings Plan (TSP), Transitioning to Civilian Life, Military Tax Benefits, Financial Independence for Veterans, Military Money Manual, The Military Money Show

Mentions:

Companion Pass information: https://www.southwest.com/rapid-rewards/tiers/companion-pass/

Chase Southwest Rapid Rewards Performance Business Card: https://www.referyourchasecard.com/226o/JUSTZTPE0R

More of Baskin Financial Planning:

Download the Ultimate Military Finance Checklist⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, with 7 pages of critical things to be thinking about to clarify your journey to financial freedom.

Think you might need some financial help? ⁠⁠⁠⁠⁠Book an intro call with me to see if we would be a mutual fit.

Questions or comments, drop me a note at: erik@baskinfp.com

www.baskinfp.com/post/56

Today, I welcome Broc Buckles, co-founder of BC Brokerage, an insurance partner for fee-only financial planners specializing in diverse insurance types, including life, disability, and long-term care. We discuss BC Brokerage’s unique approach, emphasizing honesty and transparency, especially for military veterans and active-duty members who may face insurance hurdles due to health screenings. We highlight the importance of adequate life insurance, especially for transitioning military personnel, and explore how company-provided insurance might lack portability and sufficient coverage, urging listeners to secure personal policies early. Disability insurance is crucial, as statistics show that one in four 20-year-olds will experience a disabling event before retirement, often due to illness rather than injury. These events don't necessarily mean total incapacitation; they may simply impact regular work capacity. Desk workers, for instance, could experience back pain or chronic migraines, limiting work hours. We also discuss life insurance and underscore the value of working with fee-only planners, who prioritize clients' best interests over aggressive sales tactics typical of some large firms.

Key Takeaways:

• Broc’s approach to life and disability insurance.

• Why you must take advantage of plans offered by your employer.

• Which plans set you up best for when you leave the military.

• Why you need disability insurance - even if you’re in “perfect health”.

• How to compare costs of different brokers.

• How insurance prevents strain on your retirement funds.

Key Timestamps:

(00:38) - Understanding the Insurance Industry

(01:17) - BC Brokerage: A Unique Approach

(03:46) - Life Insurance for Military Members

(11:40) - Disability Insurance Insights

(17:40) - Insurance for Business Owners

(22:11) - Why Work with Fee-Only Planners?

(24:05) - Contact Information and Conclusion

Key Topics Discussed:

BLUF Veteran Finance Podcast, Military Finance, Veteran Financial Planning, Military Money Management, VA Benefits, Military Retirement Planning, Financial Literacy for Soldiers, Military Budgeting Tips, Debt Management for Service Members, VA Loans, Military Investment Strategies, Saving for Deployment, Thrift Savings Plan (TSP), Transitioning to Civilian Life, Military Tax Benefits, Financial Independence for Veterans, Military Money Manual, The Military Money Show, Disability Insurance, Life Insurance

Mentions:

Website: https://www.bc-brokerage.com/

More of Baskin Financial Planning:

Download the Ultimate Military Finance Checklist⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, with 7 pages of critical things to be thinking about to clarify your journey to financial freedom.

Think you might need some financial help? ⁠⁠⁠⁠⁠Book an intro call with me to see if we would be a mutual fit.

Questions or comments, drop me a note at: erik@baskinfp.com

www.baskinfp.com/post/55

I outline the top three year-end tax planning strategies that can benefit you this fall. I emphasize the importance of assessing your tax situation as the year draws to a close, highlighting that by this time, you typically have a clearer picture of your income and taxes due to bonuses and other financial events. The first strategy I discuss is Roth conversions, which can be advantageous in years of lower income, allowing you to pay taxes on the converted amounts now rather than later. The second strategy focuses on charitable contribution planning, particularly through donor-advised funds (DAFs) and using required minimum distributions (RMDs) to donate directly to charity, maximizing tax benefits while avoiding capital gains taxes. Finally, I touch on retirement account contributions, stressing how contributions to traditional accounts can lower your taxable income, especially if you’re a business owner. Overall, I provide practical advice for you to optimize your tax situation as the year ends.

Key Takeaways:

• Converting traditional pre-tax money to Roth accounts can be beneficial in low-income years, allowing you to pay taxes now rather than later.

• Having a mix of traditional and Roth accounts is important for tax management in retirement, providing flexibility in withdrawals.

• Donor-advised funds (DAFs) are a powerful tool for charitable giving, allowing for immediate tax deductions and avoiding capital gains taxes on appreciated stock.

• Individuals subject to required minimum distributions (RMDs) can donate their RMDs directly to charity to avoid increasing their taxable income.

• High-income earners can use backdoor Roth contributions to get money into Roth IRAs despite income limits.

• Implementing these strategies can result in significant tax savings, sometimes amounting to thousands of dollars in reduced taxable income.

Key Timestamps:

(00:00) - 3 Fall Tax Planning Moves for Veteran Business Owners

(01:25) - Understanding Roth Conversions

(02:52) - Benefits of Roth Conversions in Retirement

(04:05) - Charitable Contribution Planning

(04:45) - Utilizing Donor Advised Funds

(05:40) - Tax Benefits of Donor-Advised Funds

(06:48) - Required Minimum Distributions to Charity

(07:48) - Maximizing Retirement Account Contributions

(09:45) - Roth Conversions and Charitable Deduction Planning

(10:56) - End-of-Year Tax Strategies Recap

(11:31) - Closing Remarks and Resources

Key Topics Discussed:

BLUF Veteran Finance Podcast, Military Finance, Veteran Financial Planning, Military Money Management, VA Benefits, Military Retirement Planning, Financial Literacy for Soldiers, Military Budgeting Tips, Debt Management for Service Members, VA Loans, Military Investment Strategies, Saving for Deployment, Thrift Savings Plan (TSP), Transitioning to Civilian Life, Military Tax Benefits, Financial Independence for Veterans, Military Money Manual, The Military Money Show, DAFs, RMDs

More of Baskin Financial Planning:

Download the Ultimate Military Finance Checklist⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, with 7 pages of critical things to be thinking about to clarify your journey to financial freedom.

Think you might need some financial help? ⁠⁠⁠⁠⁠Book an intro call with me to see if we would be a mutual fit.

Questions or comments, drop me a note at: erik@baskinfp.com

www.baskinfp.com/post/54

I dive into the critical components of employee benefits packages during open enrollment season. I walk through key considerations like health insurance options (HSA and PPO plans), life insurance, and disability insurance, explaining how they fit into both personal and family financial plans. I also touch on underutilized benefits like dependent care FSAs, 401k matches, and ESPPs, emphasizing how to maximize these offerings based on individual needs. Ultimately, this episode is a reminder to evaluate your employer benefits annually, ensuring that they align with your unique financial goals and family situation.

Key Takeaways:

• Will securing long-term disability insurance with a private policy provide greater stability for you?

• When carefully planned, FSAs can help you save on taxes.

• Ways you can maximize your employer’s 401k match and Employee Stock Purchase Plan (ESPP).

• Fringe benefits often go unnoticed or unused. Pay special attention to opportunities for gym memberships, education assistance, and more.

• Regularly reassess your benefits during open enrollment to ensure they match your family’s changing needs, especially if you’re comparing offers from different employers.

Key Timestamps:

(00:00) – Open Enrollment and Employee Benefits

(01:13) – Understanding Health Insurance Options

(03:36) – Life Insurance: What You Need to Know

(05:15) – The Importance of Disability Insurance

(07:38) – Dependent Care FSA: A Valuable Benefit

(09:14) – Maximizing Your 401k and ESPP

(10:51) – Other Important Employer Benefits

(11:39) – Conclusion and Final Thoughts

Key Topics Discussed:

BLUF Veteran Finance Podcast, Military Finance, Veteran Financial Planning, Military Money Management, VA Benefits, Military Retirement Planning, Financial Literacy for Soldiers, Military Budgeting Tips, Debt Management for Service Members, VA Loans, Military Investment Strategies, Saving for Deployment, Thrift Savings Plan (TSP), Transitioning to Civilian Life, Military Tax Benefits, Financial Independence for Veterans, Military Money Manual, The Military Money Show. ESPP, Employee Stock Purchase Plan, 401k match, fringe benefits, employee benefits, health insurance, disability insurance

More of Baskin Financial Planning:

Download the Ultimate Military Finance Checklist⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, with 7 pages of critical things to be thinking about to clarify your journey to financial freedom.

Think you might need some financial help? ⁠⁠⁠⁠⁠Book an intro call with me to see if we would be a mutual fit.

Questions or comments, drop me a note at: erik@baskinfp.com

www.baskinfp.com/post/53

In episode 52, I welcome my wife, Shelley Baskin, to talk about how we handle finances in our marriage. We share our thoughts on joint versus separate finances, the importance of open communication, and how we balance our individual spending preferences. We also dive into managing our household finances while running a business and setting long-term financial goals. Shelley and I emphasize how crucial shared values and honest communication are in creating financial harmony.

Key Takeaways:

• Should all accounts be joint? When should accounts become joint?

• Who pays for what? And is there a right answer?

• Monthly financial check-ins.

• How common values can guide financial decision making.

• When do prenups actually make sense?

• When the kids grow up, how do we want them to see money?

Key Timestamps:

(00:00) – Welcome and Introduction

(00:56) – Joint vs. Separate Finances

(03:23) – Spending Priorities and Values

(10:17) – Monthly Financial Reviews

(12:04) – Business Finances and Household Impact

(14:10) – Early Financial Planning and Saving Strategies

(15:34) – Defining Financial Goals and Comfort

(19:40) – Views on Prenups

(21:40) – Teaching Kids About Money

(23:14) – Closing Thoughts and Resources

Key Topics Discussed:

BLUF Veteran Finance Podcast, Military Finance, Veteran Financial Planning, Military Money Management, VA Benefits, Military Retirement Planning, Financial Literacy for Soldiers, Military Budgeting Tips, Debt Management for Service Members, VA Loans, Military Investment Strategies, Saving for Deployment, Thrift Savings Plan (TSP), Transitioning to Civilian Life, Military Tax Benefits, Financial Independence for Veterans, Military Money Manual, The Military Money Show, marriage, common values, monthly financial check in

More of Baskin Financial Planning:

Download the Ultimate Military Finance Checklist⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, with 7 pages of critical things to be thinking about to clarify your journey to financial freedom.

Think you might need some financial help? ⁠⁠⁠⁠⁠Book an intro call with me to see if we would be a mutual fit.

Questions or comments, drop me a note at: erik@baskinfp.com

www.baskinfp.com/post/52

In this podcast, I explore how to approach investing during election years, addressing the common questions I hear from investors about whether to adjust their portfolios as election season approaches. I discuss the historical performance of the U.S. stock market under different political parties, comparing returns during Democratic and Republican presidencies. Using examples from 1928 to the present, I show how staying invested consistently through election seasons often results in better long-term returns than trying to time the market. I emphasize the importance of focusing on your long-term investment goals rather than reacting to election-related news, pointing out that market fluctuations during election periods are hard to predict and usually don’t warrant major changes to your investment strategy.

Key Takeaways:

• Who is better for the stock market? Democrats or Republicans?

• Is there enough data to really know?

• The dangers of trying to time the market around an election.

• The best strategy is to focus on your long term investment goals.

• Stock market election years from 1928 to 2020.

• Is this election any different?

Key Timestamps:

(00:00) Introduction: Investing During Election Years

(01:45) Comparing Returns: Democrats vs. Republicans

(04:52) Case Studies: Elections 1928 to 2016

(09:28) Monthly Returns Analysis

(12:36) Concluding Thoughts

Key Topics Discussed:

BLUF Veteran Finance Podcast, Military Finance, Veteran Financial Planning, Military Money Management, VA Benefits, Military Retirement Planning, Financial Literacy for Soldiers, Military Budgeting Tips, Debt Management for Service Members, VA Loans, Military Investment Strategies, Saving for Deployment, Thrift Savings Plan (TSP), Transitioning to Civilian Life, Military Tax Benefits, Financial Independence for Veterans, Military Money Manual, The Military Money Show, 2024 election, US election, presidential election

Mentions:

https://ofdollarsanddata.com/sp500-calculator/

https://www.nasdaq.com/articles/heres-average-stock-market-return-under-democratic-and-republican-presidents-hint-it-may

https://www.fool.com/investing/2024/04/02/average-stock-market-return-democrat-republican-pr/

https://123jump.com/Monthly-Returns

More of Baskin Financial Planning:

Download the Ultimate Military Finance Checklist⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, with 7 pages of critical things to be thinking about to clarify your journey to financial freedom.

Think you might need some financial help? ⁠⁠⁠⁠⁠Book an intro call with me to see if we would be a mutual fit.

Questions or comments, drop me a note at: erik@baskinfp.com

www.baskinfp.com/post/51

In this episode, I discuss options for managing your TSP after leaving the military: keeping it in the TSP, rolling it over to an IRA or an employer-sponsored plan, or taking a distribution or purchasing an annuity. Keeping it in the TSP is easy and low-cost but offers limited investment options and multiple account management. Rolling it into an IRA provides more investment choices and easier management but can complicate backdoor Roth IRA contributions. Rolling into a new employer’s 401(k) consolidates accounts and preserves Roth IRA opportunities, though fees and options vary. Taking a distribution or buying an annuity offers different benefits and risks, including potential penalties and lower returns. The best choice depends on your personal circumstances and financial goals. Tune in to get a better idea of these options.

Key Takeaways:

• Keeping your TSP where it is can be a simple way to keep costs low and your financial life simple.

• Rolling your TSP into an IRA or 401(k) is a great way to broaden investment opportunities or consolidate accounts.

• Be cautious about taking a distribution from your TSP too soon, before 59 and a half, there can be penalties (though exceptions apply).

• Annuities are a transfer of risk to an insurance company, and can be considered, but the benefits really depend on your goals.

• To keep your TSP open, leave $200 in the account.

• The best decision depends on your situation and goals.

Key Timestamps:

(00:00) - Introduction: What to Do with Your TSP After Leaving the Military

(00:46) - Option 1: Keeping Your TSP in Place

(02:26) - Option 2: Rolling Your TSP to an IRA or Employer Plan

(04:51) - Option 3: Taking a Distribution or Purchasing an Annuity

(06:50) - Conclusion: Making the Best Decision for Your TSP

Key Topics Discussed:

Erik Baskin, Baskin Financial Planning, BLUF, Bottom Line Up Front, The BLUF Finance Podcast, Military Money Manual, veteran finances, TSP, Roth IRA, 401(k), employer sponsored retirement plans, retirement savings, low cost savings

More of Baskin Financial Planning:

Download the Ultimate Military Finance Checklist⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, with 7 pages of critical things to be thinking about to clarify your journey to financial freedom.

Think you might need some financial help? ⁠⁠⁠⁠⁠Book an intro call with me to see if we would be a mutual fit.

Questions or comments, drop me a note at: erik@baskinfp.com

www.baskinfp.com/post/50

I welcome Evan Kaufman from WeVetHomeLoans, a fellow Air Force Academy graduate and economics major, to discuss VA loan refinancing amidst the fluctuating mortgage market. Evan explains the current state of interest rates, specifically for VA loans, and how recent trends have made refinancing particularly advantageous. We cover the unique benefits of the VA Interest Rate Reduction Refinance Loan (IRRRL), also known as 'Uncle Earl,' including no appraisal or income documentation requirements, low costs, and the ability to significantly lower monthly payments. Evan also introduces a newly developed tool from WeVet that helps veterans and active duty members determine their eligibility and potential savings instantly. We emphasize the importance of resetting mortgage rates periodically to maximize financial benefits and offer detailed insights into financial planning strategies for those with VA loans.

Key Takeaways:

• What are the benefits of VA IRRRL (Interest Rate Reduction Refinance Loan)?

• When will I know it’s time to refinance my mortgage?

• How will this affect my long term savings plans?

• Evan covers the tools he offers to notify you when you’re eligible and how you could benefit.

Key Timestamps:

(00:00) - Introduction to Evan Kaufman

(02:53) - Understanding VA Loan Refinancing

(04:16) - Benefits of VA IRRRL (Uncle Earl)

(07:32) - Refinancing Process and Costs

(11:27) - Strategic Considerations for Refinancing

(20:01) - VA Funding Fees and Savings

(20:23) - The Benefits of Refinancing

(21:07) - Calculating Long-Term Savings

(22:21) - Exploring Different Refinance Scenarios

(25:19) - Introducing the VA Loan Rapid Refi Tool

(29:34) - Evan's 20-Year Vision for Clients

(32:42) - Final Thoughts and Contact Information

(35:41) - Conclusion and Resources

Key Topics Discussed:

Erik Baskin, Baskin Financial Planning, BLUF, Bottom Line Up Front, The BLUF Finance Podcast, Military Money Manual, veteran finances, refinancing VA loans, IRRRL, Evan Kaufman

Mentions:

https://wevett.com/

More of Baskin Financial Planning:

Download the Ultimate Military Finance Checklist⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, with 7 pages of critical things to be thinking about to clarify your journey to financial freedom.

Think you might need some financial help? ⁠⁠⁠⁠⁠Book an intro call with me to see if we would be a mutual fit.

Questions or comments, drop me a note at: erik@baskinfp.com

www.baskinfp.com/post/49