Money Hungry – Details, episodes & analysis

In 2024, the S&P 500 returned over 25% — yet the average investor captured only 16.54% of it. This episode explores the behavioral science behind why markets feel so dangerous when they drop, and what disciplined investors actually do differently. You'll learn why loss aversion is hardwired into your decision-making, why market timing reliably destroys returns even for intelligent people, and how to build a plan that works before volatility hits — so you're not making critical decisions in the middle of a storm.

"I'll think about it later" is one of the most expensive decisions in personal finance — but most people treat it as a neutral, low-stakes choice. This episode breaks down the real cost of delay across three areas: retirement investing, life insurance, and estate planning. The compound interest math is laid out plainly — a 10-year delay in investing can cut your final portfolio value by more than half, even if you contribute the same total amount. Life insurance premiums rise 8–12% per year with age, and health events can close that window permanently. And dying without a will can leave families locked out of accounts and forced into costly, time-consuming probate. The episode also explores why awareness of these costs rarely translates into action — and what research on financial behavior says actually moves people to start.

Most high earners assume that making more money means retirement is easier to solve. This episode challenges that assumption head-on. Social Security replaces a much smaller share of income for high earners — sometimes under 30% — meaning the burden of funding retirement falls almost entirely on you. On top of that, many standard tax-advantaged tools phase out above certain income levels, little-known strategies like the backdoor Roth and mega backdoor Roth are available but widely overlooked, and the distribution phase introduces risks — sequence of returns, Medicare surcharges, and Required Minimum Distributions — that can quietly derail even a well-funded retirement. This episode walks through each of these gaps clearly and explains what a coordinated, complete retirement strategy actually requires for high earners.

For high earners and long-term investors, taxes are often the single largest drag on wealth—yet most people never see it happening. This episode explains tax drag: how small annual tax costs compound into significant wealth differences over time, where it hides (turnover, fund distributions, asset location), and how it hits high earners especially hard through layered taxes like the Net Investment Income Tax. It then walks through four core strategies—tax-advantaged accounts, tax-loss harvesting, asset location, and Roth conversion planning—that investors use to improve after-tax returns without changing what they earn.

nly 41% of Americans work with a financial advisor—but even among those who do, most are receiving investment management, not full financial planning. This episode breaks down the difference: what investment management covers, what it leaves out, and what comprehensive financial planning actually looks like across taxes, insurance, estate planning, and retirement strategy. It also examines how advisor compensation models shape what clients receive, and gives listeners three concrete questions to ask their own advisor.

This episode traces the career path of Anthony Macaluso from the floors of Morgan Stanley and Capital One Investments to the founding of Oakfield Wealth Management. It explores why experienced advisors leave large institutions, what they find limiting about the traditional model, and how that frustration shapes a different kind of firm—one built around listening first, and designing financial strategies around the individual client.

Money Hungry is a practical, conversational podcast for high-income professionals and business owners focused on wealth building, retirement planning, and financial independence. Each episode simplifies complex investment strategy, tax-efficient planning, and market uncertainty into clear, actionable insights. If you’re successful, driven, and money hungry for smarter financial decisions, this show delivers expert guidance without hype—just disciplined strategy and long-term thinking.