One For The Money

Episode 119: Five Strategies for Retiring Early

Early retirement requires a different playbook. In this episode, I explain five strategies for bridging the gaps before Social Security and Medicare, managing taxes, and funding your lifestyle with greater flexibility.

In the tips and tricks segment, I share how Roth IRA contributions can provide an additional source of penalty-free funds before age 59½.

Key points

• Build a taxable brokerage account

• Maximize your HSA

• Use pre-tax 401(k) contributions strategically

• Establish a dedicated cash reserve

• Understand early retirement-account access

• Use Roth IRA contributions for added flexibility before age 59½

Episode 118: Building a More Satisfying Retirement

What does a successful retirement really look like?

In this episode, Jonny explores why retirement satisfaction depends on more than just the size of your portfolio. Research shows that four factors play an important role: income, savings, health, and social connection.

You’ll learn why a comprehensive retirement plan should go beyond investments and include thoughtful planning for healthcare, relationships, purpose, and the lifestyle you want to enjoy.

In This Episode

• The four key drivers of retirement satisfaction
• Why health and social connection can be as important as financial security
• How to avoid sacrificing well-being solely to build a larger nest egg
• Why many retirees report being more financially comfortable than they expected
• The ongoing role of Social Security, Medicare, and lower work-related expenses in retirement

Key Takeaway

A successful retirement is not just about having enough money to stop working. It is about having the financial confidence, health, relationships, and purpose to enjoy the life you have built.

Episode 117: Social Security Claiming Strategies and Tips for Married Couples

In this episode of One for the Money, we take a close look at one of the most important retirement decisions you can make: when to claim Social Security. While the timing can have a meaningful impact on your lifetime retirement income, too many people still make this choice without a clear strategy. We break down the key claiming ages, the tradeoffs between claiming early or delaying, and why the right decision should be based on your goals, income sources, life expectancy, and overall retirement plan.

We also explore research showing why delaying benefits can often create more long-term value than claiming early and investing the difference. In the Tips, Tricks, and Strategies section, we discuss how married couples should think about spousal benefits, survivor benefits, and how to coordinate claiming decisions to support long-term retirement income.

Key topics covered:

• When to claim Social Security and why timing matters.
• How claiming at 62, full retirement age, or 70 changes your benefit.
• Why many retirees leave money on the table by claiming too early.
• Research on the value of delaying benefits.
• Social Security strategies married couples may want to consider.
• How to think about survivor benefits and spousal coordination.

Why listen:

If you want a clearer framework for deciding when to claim Social Security, this episode offers practical guidance, planning considerations, and a few strategies that can help you make a more informed choice.

Episode 116 – The Alphabet Soup of Employee Stock Benefits

• Why employee ownership can be a powerful wealth-building tool
• Overview of ESOPs, ESPPs, RSUs, and the NUA tax strategy
• How ESOPs and ESPPs give you company stock through contributions or discounted purchases
• How RSUs work, when they’re taxed, and why they often lead to concentrated employer stock
• What NUA is and when it can reduce taxes on appreciated company stock in a 401(k)
• Key risks of single‑stock exposure and why diversification is crucial
• Practical RSU tip: when it can make sense to sell vested shares and reinvest or pay down debt
• How to think about these benefits as part of an overall financial and tax plan

If you’d like help reviewing your equity compensation and overall plan, schedule a free introductory meeting at betterplanningbetterlife.com.

This material is for general information and educational purposes only and is not intended to provide specific advice or recommendations for any individual.

In this episode of One for the Money, I revisit author Morgan Housel—best known for The Psychology of Money—and explore his newer, even more impactful book, The Art of Spending Money. I share why building wealth is only half the equation and why learning to spend that wealth intentionally, in line with your values and life experiences, is its own crucial skill. You’ll hear practical ideas for using money as a tool to create freedom, deeper relationships, and meaningful memories, rather than simply chasing a bigger account balance.

Episode 115 – The Art of Spending Money (Morgan Housel)

• Follow-up to episode 13 on The Psychology of Money
• Focus: Morgan Housel’s new book The Art of Spending Money and how to use money to live better, not just build wealth

Key Themes

• Money success is more about behavior than intelligence
• Building wealth is one skill; spending it wisely is a separate skill
• Money should be a tool for happiness and freedom, not a status scoreboard

Spending and Personal Experience

• No one-size-fits-all formula for spending; it must reflect your values and life story
• “Post-traumatic broke syndrome”: people who grew up with scarcity may struggle to spend even when they’re financially independent
• Good planning and projections help clients see what’s safe to spend, reducing fear of running out

Time, Relationships, and Happiness

• Life moves in phases; time with family is finite and irreplaceable
• At the end of life, what matters most are stories and relationships, not account balances
• As income rises, core joys often stay the same: family time, meaningful conversations, simple shared experiences

Practical Takeaways (Tips, Tricks, Strategies)

• Main drivers of happiness: strong relationships, health, meaningful work, rest, and purpose
• Spend intentionally on what truly matters; cut ruthlessly what doesn’t
• Guiding rule: “Spend extravagantly on the things you love—only if you are equally disciplined in cutting the things you don’t.”

This material is for general information and educational purposes only and is not intended to provide specific advice or recommendations for any individual.

Debt, Deficits, and Your Financial Future

In this episode of One for the Money, Jonny zooms out: yes, we’re living in the most prosperous era in human history—but America’s debt and spending habits are a growing reason for concern.

In this episode:

• How Washington turned the U.S. into a “transfer society” and why interest on the debt now rivals defense spending
• What trillion‑dollar deficits really mean (using a simple time analogy)
• Practical ways to protect yourself from future tax hikes: Roth strategies, HSAs, defined benefit plans, tax‑gain and tax‑loss harvesting
• Why voter choices—and new technologies like AI—could still shift us toward a more abundant, fiscally responsible future

Listen in to understand the stakes, then learn concrete steps you can take now to strengthen your own financial plan.

One for the Money — Episode 113

The Case for Optimism (5th Annual)

Each July, the One for the Money podcast makes the case for optimism — and this year's edition may be the most compelling yet. Despite an unsettling headlines landscape that includes the ongoing wars in Ukraine and Iran and persistent political dysfunction, the data tells a different and far more hopeful story. This episode is your annual reminder of just how remarkable a moment in history we are living through.

In This Episode

• Why 2026 — turbulence and all — is the best time in history to be alive
• America at 250: the Declaration of Independence and the outsized global contributions the U.S. has made in technology, medicine, economic growth, education, and democratic ideals
• Why freedom, protected by checks and balances, produced the most prosperous society in human history
• The paradox of low happiness despite record prosperity — and what's really driving it
• Climate fear vs. climate data: what the numbers actually show
• Global progress by the numbers, courtesy of HumanProgress.org
• Boomers vs. Millennials: what the data says about who actually had it harder
• AI anxiety in historical context — and why Chicken Little keeps getting it wrong
• Wealth inequality: where we are, where we've been, and the rise of billionaire philanthropy
• A personal note on becoming an American citizen

Key Takeaways

• Extreme poverty has fallen from over 80% of the world two centuries ago to under 9% today
• U.S. GDP per capita is now 40% higher than Western Europe and 60% higher than Japan — and growing three times faster since 2020
• Natural disaster deaths in 2024 (16,753) were well below the 20-year average of 65,566 — a 90% decline over the past century
• Political division is nothing new: from Aaron Burr to four presidential assassinations, America has always had turmoil — and always moved forward
• Millennials now have a higher average net worth at comparable ages than Boomers did
• Every major wave of technological disruption — steam, electricity, the internet — created more opportunity than it destroyed

Tips, Tricks & Strategies

Spend money on travel. As Mark Twain put it, "Travel is fatal to prejudice, bigotry, and narrow-mindedness." Whether it's Yosemite, Crater Lake, the Grand Tetons, or a trip to Thailand or Costa Rica, the conversations and memories you make along the way are among the highest-return investments you can make. Travel doesn't just broaden your perspective — it deepens your gratitude.

Remember — a better life is a result of better planning.

Episode 112: Family Matters & Money - For Better or For Worse

Money can’t buy love or happiness—but it can absolutely impact both.

In this episode of One for the Money Podcast, I share how money can either strengthen or damage the relationships that matter most in our lives. Research consistently shows that strong relationships are one of the greatest predictors of happiness, health, and longevity. The question becomes: are your financial habits helping your relationships or hurting them?

In this episode, I explore practical ways to use money intentionally to create stronger family connections, healthier communication, and lasting memories.

I also share:

• Why money is one of the leading causes of conflict in families and marriages
• Lessons from the Harvard Study of Adult Development
• How financial education can become a generational gift
• Why discussing family goals and financial plans matters
• The importance of spending money on experiences instead of just possessions
• The inspiring story of Joy Ryan and Brad Ryan visiting all 63 U.S. National Parks together

Tips, Tricks & Strategies Segment

In this week’s practical segment, I share how to use money to benefit your descendants and preserve family relationships across generations, including:

• The surprising statistic about how quickly many inheritances are spent
• The concept of “warm giving” — giving while you are alive
• Why communication and estate conversations matter
• How experiences can become one of the greatest legacies you leave behind

Key Takeaway

There may be only one thing that compounds better than money: memories.

Better planning leads to a better life—and that includes planning for the people you love most.

Thank you for listening to One for the Money Podcast!

In this episode, I break down one of the newest and most talked-about financial policies introduced in 2025: Trump Accounts. Created as part of the “One Big Beautiful Bill,” these tax-advantaged investment accounts are designed to give American children a financial head start from birth.

I cover how these accounts work, who qualifies, the role of government and private funding, and whether they make sense for your family. We also compare Trump Accounts to other popular savings vehicles like 529 plans and custodial accounts (UTMA/UGMA), so you can make an informed decision.

If you’re a parent—or planning to be—this is an important conversation about building generational wealth and setting your kids up for long-term financial success.

What You’ll Learn

• What Trump Accounts are and how they work
• Who qualifies for the $1,000 government seed contribution
• How the $5,000 annual contribution limit works
• The role of private philanthropy (including the $250 bonus opportunities)
• Key benefits and drawbacks of these accounts
• How Trump Accounts compare to 529 plans and custodial accounts
• When these accounts make sense—and when they don’t
• Why starting early matters more than the account type

Pros of Trump Accounts

• $1,000 federal seed contribution (for eligible birth years)
• Additional $250 potential philanthropic contributions
• Tax-deferred growth
• Flexible use of funds at age 18
• Employer contribution opportunities
• Simple, index-based investment approach

Cons of Trump Accounts

• No tax deduction on contributions
• Withdrawals taxed as ordinary income
• Limited investment options
• الطفل gains full control at age 18
• Lower flexibility compared to some alternatives
• New program with evolving rules and uncertainties

Trump Accounts vs. Other Options

529 Plans

• Best for education-specific savings
• Tax-free growth and withdrawals (if used for qualified expenses)
• Less flexibility for non-education use

Custodial Accounts (UTMA/UGMA)

• Greater flexibility in how funds are used
• Potential tax advantages through capital gains treatment
• No contribution limits
• Assets count toward financial aid calculations

When Trump Accounts Make Sense

• You have a child born between 2025–2028 (to capture the $1,000 seed money)
• Your child qualifies for additional philanthropic contributions
• Your employer offers contributions to the account

When to Consider Alternatives

• You’re primarily saving for education (consider a 529 plan)
• You want more tax-efficient withdrawals
• You prefer greater flexibility and control over investments

Important Dates & Timeline

• Account activation begins: Before July 4, 2026
• Initial $1,000 deposit: No earlier than July 4, 2026
• Contributions allowed starting: July 4, 2026

Final Takeaway

Trump Accounts are an interesting new tool designed to jumpstart investing from birth—but they’re not a one-size-fits-all solution. The most important factor isn’t the account type—it’s getting started early, staying consistent, and having a plan.

Subscribe

If you found this episode helpful, be sure to subscribe, share it with a friend, and leave a review. And as always, better planning leads to a better life.

Episode 110: The Hidden Power of 529 Plans (and How to Use Them Like a Pro)

Welcome back to the One for the Money podcast!

In this episode, we dive into one of the most powerful—and often misunderstood—tools for college planning: 529 plans. With graduation season in full swing, this topic hits especially close to home as families prepare for the next big (and expensive) chapter.

🎓 What’s Inside This Episode

A Personal Milestone

Graduation season is here, and in the West household, it’s a big one. From elementary school to high school, the years may feel long—but they fly by. With one son heading to college, this episode reflects both the emotional and financial realities of preparing for higher education.

💡 529 Plans: More Than Meets the Eye

At their core, 529 plans are tax-advantaged investment accounts designed for education expenses. But beneath the surface, they offer far more flexibility and strategic value than many people realize.

Here’s why they stand out:

• Tax Advantages: Contributions grow tax-deferred, and withdrawals are tax-free when used for qualified education expenses.
• Flexible Beneficiaries: You can change the beneficiary to another family member—or even yourself.
• Future Planning Power: Start a 529 today and transfer it later to future children or grandchildren.
• No Required Distributions: Funds can continue growing for years—even generations.
• Superfunding Opportunities: Front-load up to five years of gifts in one contribution for powerful estate planning.

🔄 New Rules: 529 to Roth IRA Transfers (SECURE 2.0)

Recent legislation introduced a game-changing strategy: rolling unused 529 funds into a Roth IRA for the beneficiary.

Key rules to know:

• The Roth IRA must belong to the 529 beneficiary
• The 529 must be at least 15 years old
• Contributions made within the last 5 years (and earnings) are excluded
• Annual rollovers are limited to IRA contribution limits (no double-dipping)
• Lifetime rollover cap: $35,000 per beneficiary

Why this matters:

This creates an opportunity to “jump-start” a child’s retirement savings—potentially turning unused college funds into long-term, tax-free growth.

🚀 Strategy Spotlight: Start Early, Think Long-Term

By funding a 529 early in a child’s life and gradually rolling funds into a Roth IRA (once eligible), families can harness decades of compounding. With consistency and time, even modest amounts can grow into significant retirement assets.

🛠️ Tips, Tricks & Strategies: Investing Inside a 529

Don’t overlook how you invest within the account:

• Early Years: Consider growth-oriented or stock-heavy portfolios to maximize long-term returns
• 5 Years from College: Gradually shift to more conservative investments
• Preserve What You’ve Built: As college approaches, focus less on growth and more on preserving funds

Real-life approach:

As college nears for the host’s oldest son, the first few years of expenses have been moved into conservative investments—reducing the risk of a market downturn right when the money is needed.

🎯 Key Takeaway

529 plans aren’t just college savings tools—they’re flexible, strategic, and surprisingly powerful vehicles for both education and long-term financial planning.

Thanks for listening!

If you found this episode helpful, be sure to share it with someone navigating college planning. And remember:

A better life is the result of better planning—and that absolutely includes planning for education.

See you next time!

Resources

Congress.gov – SECURE 2.0 Act (529-to-Roth IRA Provision)

Fidelity Investments – 529-to-Roth IRA Transfer Rules Explained

FINRA – 529 Plan Investment Strategies

Internal Revenue Service – 529 Plans (Qualified Tuition Programs)

Saving for College – Complete Guide to 529 Plans

Saving for College – 5-Year Gift Tax Averaging (Superfunding)

Schwab – Understanding 529 to Roth IRA Rollovers

U.S. Securities and Exchange Commission – Introduction to 529 Plans

Prior to investing in a 529 Plan investors should consider whether the investor's or designated beneficiary's home state offers any state tax or other state benefits such as financial aid, scholarship funds, and protection from creditors that are only available for investments in such state's qualified tuition program. Withdrawals used for qualified expenses are federally tax free. Tax treatment at the state level may vary. Please consult with your tax advisor before investing. (19-LPL)

The content in this material is for general information only and are not intended to provide specific advice or recommendations for any individual. All information is believed to be from reliable sources; however, LPL Financial makes no representation as to its completeness or accuracy.