The Fiscal Foxhole – Roth Conversions: Tax Nerdery Finale

Hosts: Rob Moore & Omen Quelvog

Release Date: November 26th,, 2025

Episode Summary

In this jam-packed episode, Rob and Omen celebrate the Marine Corps birthday, share Thanksgiving plans, and dive deep into two hot financial topics: the proposed 50-year mortgage and Roth conversions. They break down the math, the myths, and the practical strategies for listeners navigating today’s housing market and retirement planning.

Key Topics & Segments

1. Celebrations & Listener Questions

• Marine Corps birthday shoutout.
• Thanksgiving plans and family traditions.
• Announcement: First listener question received! Tune in next episode for answers.

2. Headline: The 50-Year Mortgage Gambit

• The math behind longer-term loans: Lower monthly payments, but nearly double the lifetime interest.
• Why stretching loan terms doesn’t solve housing affordability—and could inflate prices further.

3. Roth Conversions:

• Roth vs. Tax-Deferred: Quick refresher on the differences..
• Roth conversions explained: Moving money from tax-deferred to Roth, paying taxes now for future tax-free growth.
• Timing matters: Low-income years, deployments, and the “retirement valley” are prime opportunities.
• Special considerations for military families and surviving spouses (“widow’s tax”).

4. Practical Roth Conversion Strategies

• Partial conversions: Fill up your tax bracket year by year.
• Planning for tax impacts: Always have cash on hand to pay conversion taxes—don’t use IRA funds if under 59½.

5. Fun Tax Facts

• Molasses Act of 1733: Rum trade and sneaky taxes.
• Townshend Act of 1767: 63 types of paper taxed!
• Estate tax for the Navy (1797–1802): Funding battleships with document stamps.

6. Trivia Challenge

• Mortgage history: What was the required down payment in 1782?

7. Off Duty: Dog Stories & Life Updates

• Rob and Omen share updates on their dogs, including surgery, recovery, and puppy growth.

Connect & Subscribe

• Questions for the show? Email: [email protected]
• Book an appointment with Omen
• Book and appointment with Rob
• Enjoyed the episode? Please subscribe, write a review, and share The Fiscal Foxhole with friends!

Disclaimer: This podcast is for educational and entertainment purposes only. Rob Moore and Omen Quelvog are registered investment advisor representatives, but are not your advisors. Nothing in this episode should be taken as specific investment, legal, or tax advice. Please consult a qualified professional for guidance tailored to your individual circumstances.

Episode Summary

In this episode, Rob and Omen dig into the world of tax loss and gain harvesting, break down the essentials of car insurance, and share some off-duty culinary adventures. Whether you’re a military family, a financial planning enthusiast, or just here for the banter, there’s something for everyone.

Key Topics & Highlights

1. Car Insurance Deep Dive

• How your car’s make and model can impact insurance premiums
• Why recent years have seen a spike in rates (up 12% in 2025)
• The importance of tailoring coverage to your needs—not just picking the cheapest option
• Understanding state minimums, liability, and umbrella policies
• Special considerations for families with teenage drivers

2. Tax Loss & Gain Harvesting Explained

• What is tax loss harvesting? How can it offset gains and reduce your tax bill?
• The “final four” analogy for matching short-term and long-term gains/losses
• Carrying forward losses and the $3,000 annual deduction rule
• The wash sale rule: what it is, how to avoid it, and why it matters
• Tax gain harvesting: when and why to intentionally realize gains in low-income years
• Practical tips for tracking cost basis and managing lots

3. Fun Tax Facts

• The beard tax of 1698 (thanks, Peter the Great)
• The cat food deduction for junkyard owners
• The famous “Chesty Love” case: breast implants as a business expense

4. Off-Duty & Trivia

• Smoked sausage fatty recipe and BBQ talk
• Trivia challenge: wild hedge fund tax loss strategies (and a zero-point streak for Rob)
• Outtakes and behind-the-scenes laughs

Key Takeaways

1. Car Choice Matters: The car you drive can seriously impact your insurance bill. Check how your dream car scores with insurers before you buy.
2. Tax Loss Harvesting: Selling investments for less than you paid can offset other gains and up to $3,000 of regular income each year.
3. Wash Sale Rule: You can’t buy the same or substantially identical investment within 30 days, or the IRS cancels your loss. Track your trades carefully.

• Subscribe & Share: If you enjoyed this episode, please subscribe and share The Fiscal Foxhole with a friend!
• Send Us Your Questions: Email [email protected] with questions or topics you’d like covered.
• Book a Consultation:
  • Book a meeting with Omen
  • Book a meeting with Rob

Disclaimers

This podcast is for educational and entertainment purposes only. Rob Moore and Omen Quelvog are registered investment advisor representatives, but they are not your advisors. Nothing you hear on The Fiscal Foxhole should be taken as specific investment, legal, or tax advice. For guidance tailored to your situation, consult a qualified professional.

Episode Summary

Welcome to the Foxhole! Hosts Omen Quelvog and Rob Moore kick off a three-part miniseries on tax nerdery, starting with the surprisingly complex world of tax withholdings. Whether you’re a military veteran, retiree, or just someone who wants to keep more of your paycheck, this episode is packed with practical advice, fun tax facts, and actionable steps to help you avoid giving the IRS an interest-free loan.

Key Topics Covered

• Why Withholdings Matter: How underpaying or overpaying taxes throughout the year can impact your finances—and why a big refund isn’t always a win.
• Safe Harbor Rules: What they are, why they matter, and how to use last year’s tax return to avoid penalties.
• W-2 vs. Self-Employed: Strategies for managing withholdings across multiple jobs, pensions, and self-employment income.
• Fun Tax Facts: From England’s window tax to Missouri’s bachelor tax, plus ABBA’s glittery costumes and the “vanishing children” of 1987.
• How to Check Your Withholdings: Step-by-step breakdown of the basic tax formula, plus recommended online calculators (IRS and Dinky Town).
• Action Steps: When and how to adjust your W-4, and what to do if your life changes (marriage, divorce, new dependents, moving states, bonuses).

Featured Resources & Links

• IRS Withholding Estimator (note: may not be updated for the latest tax law)
• Dinky Town Tax Calculator
• Email your questions: [email protected]
• Book a free consultation with Rob
• Book a free consultation with Omen

Practical Takeaways

1. Lifelong savers often struggle to spend in retirement. Identify what matters most and spend intentionally with a plan.
2. Your tax refund or bill isn’t a grade. Aim to break even—no big refund, no big liability.
3. Tax planning is a year-round habit. Review withholdings and estimated payments after major life changes.

If you found this episode helpful, please share it with a friend—especially fellow military veterans and retirees who could benefit from smarter tax planning. Rate and comment wherever you listen to podcasts. Your feedback helps us reach more listeners and keeps the educational mission alive!

Disclaimer

Rob Moore and Omen Quelvog are registered investment advisor representatives. This podcast is for educational and entertainment purposes only. Nothing you hear should be taken as specific investment, legal, or tax advice. Please consult a qualified professional for guidance tailored to your situation.

🎙️ Episode Summary

In this episode, Rob and Omen welcome Heather Walrath to the foxhole. Heather shares her expertise on VA benefits and disability claims along with other valuable VA benefits. In the news segment, Rob and Omen discuss recent headlines about gold and precious metals, their role in investment portfolios, and how market hype can influence investor behavior.

🗝️ Key Topics Covered

• Gold & Precious Metals:
  • Recent volatility in gold prices and what it means for investors.
  • The importance of low correlation assets in a diversified portfolio.
  • Why emotional investing can derail your financial plan.
• VA Benefits & Disability:
  • Heather’s background and credentials.
  • How to get started with VA benefits.
  • Navigating the VA system and avoiding scams.
  • The value of working with accredited experts.
• Personal Stories:
  • Rob and Omen’s marathon training and running anecdotes.
  • Reflections on podcasting, editing, and the value of sharing financial education.

💡 Main Takeaways

1. Market Hype vs. Fundamentals: Emotion-fueled rallies can turn quickly. Gold’s fundamentals are strong, but corrections happen when sentiment overshoots reality.
2. Getting Started with VA Benefits: Begin early and stay organized. Use va.gov and veteran service organizations to guide you through eligibility and paperwork.
3. Navigating the VA Maze: Work with trusted, accredited experts to avoid scams and get the benefits you deserve.

Links

If you enjoyed this episode, please leave us a review, share it with a friend, and subscribe to The Fiscal Foxhole. Questions for the show? Email us at [email protected]. Interested in financial planning? Rob Moore and Omen Quavo are accepting new clients.

• Schedule a free consultation with Rob at Everman Prosperity
• Schedule a free consultation with Omen Formermynder Wealth Management:
• Connect with Heather Walrath

Disclaimer: Rob Moore and Omen Quelvog are registered investment advisor representatives. This podcast is for educational and entertainment purposes only. Nothing you hear should be taken as specific investment, legal, or tax advice. Please consult a qualified professional for guidance tailored to your situation.

🎙️ Episode Summary

In this episode, Omen and Rob bust the top five myths about transitioning out of the military. Drawing from personal experience and real conversations in military financial circles, they break down common misconceptions, share practical advice, and offer candid stories about life after service. The episode also features a headline segment on new legislation affecting 401(k) investments, a trivia challenge, and practical takeaways for listeners preparing for their own transition.

🗝️ Key Topics & Segments

• Headline News: New bill codifies Trump’s executive order on alternative investments in 401(k)s, opening the door to private equity, real estate, and crypto. Omen and Rob discuss what this means for retirement plans and why caution is needed.

✅Myths About Leaving the Military (from Episode 6)

• VGLI is a ripoff
• Military discipline guarantees civilian success
• SBP (Survivor Benefit Plan) is a bad deal compared to buying term insurance and investing the difference
• You cannot touch your TSP until age 59½
• The military handles your retirement for you
• Filing a BDD (Benefits Delivery at Discharge) claim guarantees a rating prior to separation and immediate payments
• VA benefits are only available to those who retire from the military
• I’ll get 100% VA disability because my buddy did
• I’ll go to college right after separation
• I’ll cash out my TSP to start a business or buy a home as soon as I separate
• Buying a house using your VA disability rating is easy right after separation
• I can keep my current state residence and tax situation when I retire

💡 Practical Takeaways

1. Don’t solve problems that don’t exist: Avoid investments you don’t understand; keep it simple and seek help when needed.
2. Treat your transition like a mission: Prep early, recon your options, and don’t go AWOL on your future.
3. You’re the CEO of your next mission: Civilian life comes with choices—make them count.

🏅 Host Highlights

• Oman celebrates earning his CFP® designation after years of hard work.
• Rob shares insights from his recent retirement ceremony and the importance of family seeing both sides of military life.

If you enjoyed this episode, please subscribe, write a review, and share The Fiscal Foxhole with a friend! Your support helps us reach more listeners and continue bringing practical financial advice to the military community.

Connect & Learn More:

• Schedule a free consultation with Rob at Everman Prosperity
• Schedule a free consultation with Omen Formermynder Wealth Management:

Disclaimer:Everman Prosperity, LLC and Former Wealth Management, LLC are registered investment advisors in the Commonwealth of Virginia. This podcast is for informational purposes only and does not constitute investment advice or a solicitation to buy or sell securities. All investing involves risk, including the potential loss of principal. Please consult a qualified financial professional before making any investment decisions.

🎙️ Episode Summary

Rob and Omen tackle one of the most debated questions for military families and frequent movers: Should you buy or rent your next home? Drawing on years of PCS experience, personal stories, and client case studies, they break down the pros and cons of each option, share practical tips for open enrollment season, and remind listeners that the “right” answer is the one that fits your life, not just your spreadsheet.

📰 This Week’s Headline

Open Enrollment for Military & Federal Benefits: The hosts highlight two timely articles from Military.com about open enrollment for FedVIP (dental/vision) and TRICARE health insurance. They explain who qualifies, why it matters, and how to use open enrollment and qualifying life events to optimize your coverage. Plus, a deep dive into the new Flexible Spending Account (FSA) options for active duty and retirees—including tips for maximizing healthcare and dependent care savings.

💡 Key Topics & Takeaways

• Buying a Home: Pros & Cons
  • Build equity and net worth with every mortgage payment
  • Stability, control, and the emotional value of “home”
• Renting a Home: Pros & Cons
  • Ultimate flexibility for PCS moves and changing plans
  • No maintenance worries, predictable costs, and lower monthly payments
• Military-Specific Insights
  • How BAH (Basic Allowance for Housing) factors into buy vs. rent decisions
  • The impact of short assignment windows and market timing
• FSA Tips
  • How to use healthcare and dependent care FSAs to save on taxes
  • Contribution limits, rollover rules, and qualifying expenses for military families

🏡 Off Duty

Rob and Omen share updates on family life, terminal leave, and the bittersweet experience of closing out a military career. Rob reflects on his last mission at Arlington National Cemetery and the emotional transition to civilian life, while Omen celebrates having his son home from Kirtland AFB.

📚 Resources & Links

• FedVIP Benefits Eligibility Tool
• FEDVIP Open Season for Military and Retiree Health Insurance | Military.com
• Everything You Need to Know About Tricare Open Enrollment | Military.com
• FSAFEDS
• Connect with Rob
• Connect with Omen

📬 Get In Touch

Have questions or want your topic featured on the show? Email: [email protected] Rob and Omen are accepting new clients and happy to chat about your financial game plan.

Omen and Rob welcome their second guest, Air Force veteran and financial planner Erik Baskin, for a candid roundtable on what it’s really like to leave the military before reaching pension eligibility. Erik shares his journey from hospital administrator to successful firm owner, and the trio compare their different career arcs, transitions, and the trade-offs between stability, entrepreneurship, and personal values.

📰 This Week’s Headline

Government Shutdown & Emergency Funds: The hosts discuss the October 1st government shutdown, its impact on federal workers, and why emergency funds are more important than ever. They share practical tips for managing expenses, using financial institution support, and finding silver linings in unexpected downtime.

💡 Key Topics & Takeaways

• Career Transitions: Comparing the experiences of leaving the military at 5, 20, and 25 years, and how timing affects financial and personal outcomes.
• Entrepreneurship vs. Stability: Why Erik chose to “burn the boats” and launch his own firm, and how military service can be a powerful launching pad for business ownership.
• Financial Planning for Transitions: The math behind leaving early—calculating the value of pensions, healthcare, GI Bill, and other benefits. Why liquid savings and a strong financial runway are critical for flexibility.
• Healthcare After Service: Navigating health insurance options post-military, including marketplace plans, Medi-Share, VA healthcare, and ChampVA for families.
• Veteran Benefits: VA disability, VA loans (including IRRRL streamlined refinancing), GI Bill, and how to maximize these lifelong advantages.
• Values & Community: The importance of aligning career decisions with personal values, family priorities, and finding a supportive tribe after leaving the military.

🏆 Game Time Segment

Erik plays trivia for Omen: In 2021, what was the total amount of loans guaranteed by the VA loan program? A) $155 billion B) $290 billion C) $341 billion D) $447 billion

🏡 Off Duty

Rob and Omen swap stories about hobbies, marathon training, buying new gear, and the realities of staying active (and watching your diet) as life moves forward. Omen shares his quest to qualify for the Boston Marathon, while balancing other physical habits such as lifting, cycling, and balancing with the joys of family time.

📚 Resources & Links

• BBC: Why the US Government Has Shut Down and What Happens Now
• Erik Baskin – Baskin Financial Planning
• Veteran Finance Podcast
• DoD Retirement Calculators
• Connect with Rob
• Connect with Omen

📬 Get In Touch

Have questions or want your topic featured on the show? Email: [email protected] Rob and Omen are accepting new clients and happy to chat about your financial game plan.

In this episode, Omen and Rob welcome their first guest to the foxhole: Brandon Lovingier, Army veteran and creator of “The Enlisted Money Guy.” Together, they tackle the big question: “Is 20 years in the military really worth it?” Brandon shares his personal journey, the financial and emotional ups and downs of military life, and how service members can make empowered career decisions. The conversation blends practical advice, honest reflections, and a few laughs about foxhole etiquette.

📰 This Week’s Headline

FAFSA Opens Early: Omen and Rob discuss the Department of Education’s early release of the FAFSA (Free Application for Federal Student Aid), why it matters for military families, and how recent changes make it easier to apply for college aid. They break down what counts (and doesn’t count) as assets, and share tips for maximizing eligibility—especially for those using GI Bill benefits and state programs.

💡 Key Topics & Takeaways

• Military Retirement: BRS vs. Legacy: Why Brandon would choose the Blended Retirement System (BRS) over the legacy pension, and how continuation pay and TSP matching can boost financial security.
• Calculating the Value of a Pension: How to estimate the lifetime value of military retirement, and why it’s only part of the bigger picture.
• The Human Side of Service: The emotional and family costs of a 20-year career—deployments, relocations, and the impact on spouses and children.
• Mental Health & Leadership: Brandon’s honest account of seeking therapy, overcoming stigma, and how military life shapes resilience and character.
• Financial Empowerment: Why having your finances squared away gives you the freedom to choose your own path—whether that’s staying in, transitioning out, or pursuing new opportunities.
• Decision Framework: Brandon’s “Numbers, Emotions, and Time” approach to making big life and career decisions.

📚 Resources & Links

• CNBC: FAFSA Opens Early
• Home - Enlisted Money
• Brandon Lovingier, ChFC®, MQFP® (@enlistedmoneyguy) • Instagram photos and videos
• Enlisted Money | LinkedIn
• Military OneSource Retirement Calculators
• Connect with Rob
• Connect with Omen

📬 Get In Touch

Have questions or want your topic featured on the show? Email: [email protected] Rob and Omen are accepting new clients and happy to chat about your financial game plan.

In this episode, Omen and Rob dig into one of the most common questions for service members and federal employees: “Should I save in my TSP, open an IRA, or just YOLO and spend?” They break down the pros and cons of each savings vehicle, share personal stories (including a surprise Great Dane puppy!), and offer practical advice for building a balanced financial life—without sacrificing fun.

📰 This Week’s Headline

Government Shutdown & Your Investments: The hosts discuss the looming federal government shutdown and its impact on the stock market. Despite the headlines, history shows markets are surprisingly resilient during shutdowns. Rob and Omen emphasize the importance of staying the course and not letting fear-based news drive your investment decisions.

💡 Key Topics & Takeaways

• Savings Frameworks: The 50/30/20 rule and why starting with 20% savings (even if it feels painful) is a solid goal. How to automate savings and make small, manageable changes over time.
• TSP vs. IRA: Why getting the match in your TSP is “free money.” The flexibility and benefits of IRAs, including spousal IRAs for military families.
• Roth vs. Traditional: How to decide between Roth and traditional accounts based on your effective tax rate and life stage. Why a mix of both can be smart, and how Roth IRAs can act as a backup emergency fund.
• Order of Operations: Step-by-step strategy: Get the TSP match, max out your IRA, then max out TSP, and finally save in a taxable brokerage account.
• YOLO (You Only Live Once): Why responsible saving means you can also spend on things that matter to you—whether it’s a dream vacation, a new car, or even a giant puppy.
• Military-Specific Tips: Special considerations for service members, including how allowances affect TSP contributions and the importance of factoring in pensions and benefits.

🏆 Game Time Segment

Rob challenges Omen with a trivia question: Which of the following is a real example of someone using a Self-Directed IRA to generate retirement income? A) Racehorse in the Kentucky Derby B) Spaceship in a video game leased for virtual rent C) Haunted house attraction D) Vending machine empire

📚 Resources & Links

• Kiplinger: What Does a Government Shutdown Mean for Stocks?
• Rob Moore’s 1% Bump Article
• 50/30/20 Calculator - Email [email protected] to request your copy!
• Book a Consultation with Rob Moore
• Contact | Get In Touch — Formynder Wealth Management

📬 Get In Touch

Have questions or want your topic featured on the show? Email: [email protected] Both Rob and Omen are accepting new clients and happy to chat about your financial game plan.

Fiscal Foxhole – Episode 1: “Debt vs. Savings – What Should You Do With Extra Cash?”

Hosts: Omen Quelvog & Rob Moore

Release Date: October 22nd, 2025

🎙️ Episode Summary

Welcome to the inaugural episode of Fiscal Foxhole! Hosts Omen Quelvog and Rob Moore kick off the series by tackling one of the most common (and complicated) financial questions: “If you suddenly come into extra money, should you pay down debt or pile up cash?”

They break down the pros and cons of each approach, share personal stories from military life, and offer practical advice for finding the right balance—especially for service members and their families.

💡 Key Topics & Takeaways

• Debt vs. Savings:
  • Why paying off high-interest debt is often a guaranteed “win.”
  • The psychological and behavioral side of debt aversion.
• Emergency Funds:
  • Why every household (military or civilian) needs a liquid emergency fund.
  • How much is enough? The “three to six months” rule explained.
• Balanced Approach:
  • Why going “all in” on either debt or savings can backfire.
  • How to split extra cash between mini-emergency funds and debt payoff.
• Military-Specific Tips:
  • TSP matching and maximizing contributions (especially in combat zones).
  • The Savings Deposit Program and other unique opportunities for service members.
• Behavioral Finance:
  • Recognizing spending habits and cash flow problems.
  • The importance of open conversations with partners about money.

📚 Resources & Links

• The stock market finally has what it wants — and is now asking 'now what?' - Hamza Shaban
• How to Maximize TSP Contributions in a Combat Zone – Doug Norman, Military Wallet
• Snowball vs. Avalanche Debt Calculator – Rob Moore
• Book a Consultation with Rob Moore
• Book a Consultation with Omen Quelvog

📬 Get In Touch

Have questions or want your topic featured on the show? Email: [email protected]

Both Rob and Omen are accepting new clients and happy to chat about your financial game plan.

Thanks for joining us in the financial trenches! Subscribe, share, and stay tuned for Episode 2.