Capitalist Investor

Most retirement planning focuses on building wealth. But what happens when age, illness, or cognitive decline make it difficult, or impossible, to manage your money?

In this episode of The Capitalist Investor, Diamond Hands D is joined by Sam and Jack to talk through one of the most important retirement planning conversations families tend to avoid: how to protect your finances before something goes wrong.

They discuss why cognitive ...

For decades, the 4% rule has been one of the most common retirement planning guidelines. The idea was simple: withdraw 4% of your portfolio in the first year of retirement, adjust for inflation each year, and your money should last for 30 years.

But does that rule still work today?

In this episode of The Capitalist Investor, Diamond Hands D is joined by Sam and Jack to break down where the 4% rule came from, why it was never meant to...

Most people assume the key to retirement is aggressively saving every extra dollar possible. But what if working just two more years could have an even bigger impact?

In this episode of The Capitalist Investor, Tony and Derek break down the surprising math behind delaying retirement. They explain how two additional working years can potentially increase 401(k) contributions, allow more time for compound growth, reduce early withdraw...

Many Americans dream about retiring early, but few fully understand the healthcare costs that come before Medicare eligibility at age 65. In this episode of the Capitalist Investor, Mark Tepper and Tony Zabiegala break down the real financial impact of retiring early and why healthcare planning needs to be part of every retirement strategy.

They discuss COBRA, Affordable Care Act options, HSA strategies, Roth conversions, tax effici...

What happens when one spouse is ready to retire… and the other hasn’t even thought about what retirement actually looks like yet?

In this episode of The Capitalist Investor, the team breaks down the retirement conversations couples often avoid until it’s too late. From retirement timelines and spending habits to travel plans, Social Security decisions, healthcare costs, and lifestyle expectations, this discussion ...

What happens when the market drops right as you need your money most? 

In this episode, we break down one of the biggest retirement planning mistakes people make: being overexposed to the stock market without a true cash safety net. Using real-world market scenarios like the 2020 crash, we discuss sequence of returns risk, retirement income planning, and why liquidity matters more than most investors realize. 

We also explo...

Are Social Security increases actually helping retirees or quietly falling behind?

In this episode of The Capitalist Investor, we break down why a recent 2.8% cost of living adjustment may feel more like a loss than a gain. When rising costs for healthcare, groceries, and energy outpace government adjustments, retirees are left asking a simple question: is this really enough?

We also explain how COLA is calculated and why it may not ...

Most people think they understand retirement planning… but the reality is, small decisions today can completely change your future. Whether you’re contributing to a 401k, exploring a Roth IRA, or just starting to think about saving for retirement, this conversation breaks down what actually matters.

We cover how everyday spending habits impact your ability to save, build retirement income, and reach true financial freed...

For those nearing retirement, the absence of a clearly defined financial plan can create significant risk, regardless of accumulated assets. This episode examines the consequences of delayed planning and the challenges that arise when key factors such as longevity, healthcare costs, inflation, and spending are not properly accounted for.

The discussion explores why individuals often avoid planning, the importance of understanding pe...

In this episode of The Capitalist Investor, Tony Zabiegala speaks with Sam Petitjean about earning the Certified Financial Planner designation and what that process reveals about the depth of financial advice.

They discuss the discipline required to complete the CFP, the difference between basic investment management and true financial planning, and why coordination across tax, legal, and investment strategy matters for long-term ou...

As retirement approaches, the margin for error narrows. What helped build wealth may no longer be appropriate once income replaces accumulation, and poorly managed risk at this stage can have lasting consequences. 

In this episode, the discussion centers on how portfolio structure should evolve before and after retirement. The conversation explores the impact of market downturns at the wrong time, the importance of rebalancing,...

For investors with significant assets, geopolitical events can introduce uncertainty that extends beyond short-term market movement. Energy prices, inflation pressures, and supply chain disruptions all play a role in shaping the economic landscape.

This episode examines how current conflict in the Middle East is affecting markets, with a focus on energy dependency, market volatility, and sector-level impacts. The conversation highli...

Many experienced investors question whether recent market volatility reflects a deeper structural issue or simply a shift in expectations.

In this episode of The Capitalist Investor, Tony and Dave discuss the difference between headline driven volatility and fundamental market deterioration. They explore how geopolitical developments can influence energy markets, why employment and earnings growth remain important indicators of stab...

Debt can be a powerful financial tool, but it can also become a major obstacle as retirement approaches.

In this episode of The Capitalist Investor, Derek Gabrielsen and Jack Root explore how debt affects retirement planning and why managing liabilities becomes increasingly important as earning years begin to shrink.

The conversation covers how business owners should approach debt tied to their companies, why exit planning matters fo...

For investors nearing retirement, decisions surrounding pension elections and portfolio discipline require careful analysis. In this episode, we examine two foundational areas of retirement planning.

First, we discuss the mechanics of portfolio rebalancing and its role in maintaining intended risk levels over time. Second, we analyze a real world pension scenario involving a $60,000 lifetime annuity versus a $1.2 million lump sum. T...

If you are approaching retirement, investment risk is no longer just about chasing higher returns. It becomes about whether you have enough time to recover from market declines and how volatility can affect your ability to retire when planned. 

In this episode of The Capitalist Investor, Diamond Hands - Derek and Jack Root discuss how risk tolerance evolves as retirement nears and why preserving capital, managing allocation, an...

In this episode of The Capitalist Investor, Derek and Tony break down how California’s tax system can impact professional athletes, even after winning a championship.

They also examine whether consumer spending is truly slowing, reviewing retail growth data, job creation numbers, wage trends, and what higher tax refunds in 2026 could mean for the economy.

Finally, they discuss the streaming wars and whether cutting cable has ac...

In this episode, Tony and Derrick open with a practical warning about identity theft and financial fraud, sharing real client stories and simple steps you can take today, including changing passwords, freezing credit, and using identity monitoring services.

They then shift into recent market volatility, breaking down gold and silver swings, Bitcoin’s technical patterns, and the surprising connection to the McRib. The conversat...