Real Money Pros

For many, index funds are one of the best ways to build long-term wealth. But as portfolios grow and taxable investments become a larger part of the picture, the conversation often shifts beyond investment returns. Today, Nic talks about how direct indexing fits into the next stage of financial planning. He explains why successful investors with large taxable brokerage accounts may begin looking f...

Brian Wiley is joined by business coach and author Allison Dunn for a conversation about why critical thinking is one of the most valuable financial skills an investor, business owner, or retiree can develop. They discuss how better decision-making applies to retirement planning, leadership, investing, and navigating life's biggest financial choices. The show also answers listener questions on ret...

Most families don't think about Medicaid planning until they're facing a health crisis—but by then, some of the best planning opportunities may already be gone. Nic and Jeremiah are joined by Brooke Baker and Jessica Young of Legacy Navigation for an in-depth conversation about the realities of long-term care, Medicaid eligibility, and protecting family assets. Together, they break down the differ...

Brian Wiley and Jeremiah Bates open the show with a discussion on concentrated stock positions, portfolio rebalancing, and the challenges investors face after large gains. Using examples ranging from Micron stock to broader market opportunities, they explore diversification, risk management, investor psychology, and the ongoing battle between fear and greed. The conversation also examines what it...

SpaceX officially went public, raising a record $75 billion and becoming the largest IPO in history—and Jeremiah Bates and Nick Daniels spend the first hour breaking down what that means for investors, how IPOs work, whether buying newly public companies makes sense, and how many investors may gain exposure through index funds and retirement accounts. The conversation then shifts to a major tax pl...

Estate planning used to be relatively straightforward: create a will, establish a trust if appropriate, and make sure your beneficiaries were named correctly. Today, it's much more complicated. We talk about how modern estate planning has evolved beyond traditional documents and why many families may have planning gaps they don't realize exist. Common reasons estate plans become outdated, the grow...

What happens to your money, your assets, and even your digital life if you don't have children to step in? Jeremiah Bates and Alex Lundgren spend the first hour tackling one of the fastest-growing estate planning challenges in America: planning for incapacity and inheritance when there are no children or obvious heirs. The discussion covers power of attorney decisions, trustees, elder abuse risks,...

Can you really know if you're ready to retire? Jeremiah and Alex spend much of this episode unpacking one of the most commonly misunderstood tools in financial planning: retirement projections and Monte Carlo simulations. They explain what an 85% or 90% probability of success actually means, why those numbers can be useful, and where they can create a false sense of certainty if they're viewed in...

For decades, most people focus on one side of retirement planning: Saving money, building investments, and growing retirement accounts. But eventually the question changes: "How do I actually live off this?" Nic talks about one of the biggest and most overlooked transitions in retirement: replacing a paycheck with income created from your own portfolio. From dividend-paying investments and automat...

Financial problems don't always come from bad decisions—they often come from not understanding the rules. Jeremiah Bates and Nic Daniels break down the costly financial mistakes people make when acting without a clear strategy. The conversation starts with the growing threat of AI scams, wire fraud, romance scams, and why even younger, financially savvy individuals are getting caught off guard. Fr...

"I'd retire tomorrow… if it weren't for health insurance." It's one of the most common concerns we hear from people approaching retirement, especially those hoping to leave work before Medicare begins at age 65. In this podcast, Nic Daniels breaks down the real planning considerations behind retiring before Medicare eligibility. From COBRA and Affordable Care Act marketplace plans to spouse covera...

Jeremiah Bates and Alex Lundgren spent Mother's Day weekend tackling one of the biggest financial issues many families avoid until it's too late: long-term care and the cost of aging. The show opens with Brooke Baker and Jessica Young, Co-Founders of Legacy Navigation, breaking down how Medicaid actually works, what it really covers, and the biggest misconceptions families have around qualifying f...

What happens when your 401(k) suddenly surges and your lifestyle starts rising with it? This week, Brian and Jeremiah uses a real example of Micron stock climbing over 600% in about a year to show how quickly investor behavior can change. They break down how rising account balances lead to increased spending, more confidence, and a shift away from the original concern many had just a year ago: how...

Taking money out of your accounts sounds simple… but it's usually not as simple as it seems. In this episode, Nic walks through why withdrawals are more than just getting cash. They're actually one of the biggest tax decisions you'll make, especially in retirement. From understanding the difference between pre-tax, Roth, and brokerage accounts to seeing how each one impacts your taxes over time, t...

A simple tax question turns into a bigger realization: even if you don't owe income tax, you can still owe thousands in self-employment tax. Brian and Alex break down why a new graduate's tax bill didn't disappear after the standard deduction—and how Social Security and Medicare taxes quietly hit 1099 income at ~15%, catching a lot of people off guard. They shift into the real math behind Social S...

  Most people don't have a money problem—they have a follow-through problem. Brian Wiley and Jeremiah Bates use real-life case studies, including a massive estate mess left behind by Brian's own father, to show why DIY financial planning often leads to incomplete or broken outcomes—especially when trusts aren't properly funded or plans aren't kept up to date. The conversation goes into estate plan...

Guaranteed income is often seen as the goal in retirement, but it comes with trade-offs that many investors don't fully understand. This podcast breaks down what you're actually giving up when you exchange a lump sum for a fixed income stream. While guaranteed income can provide predictability and peace of mind, it often comes at the cost of flexibility, control, liquidity, and long-term planning...

A volatile stretch tied to the Iran conflict quickly reversed last week, giving us a real-time example of how fast markets can swing and why reacting to short-term headlines can backfire. Jeremiah and Alex tackle listener questions, starting with whether apps like Acorns are a legitimate way to build wealth and leave money behind for family. That conversation turns into a deeper look at estate pla...

If you have one, choosing between a pension lump sum and monthly income may seem simple, but it's one of the most important financial decisions you'll make in retirement. Nic breaks down the key differences between taking a guaranteed monthly pension and opting for a lump sum payout. While many people approach this decision based on whether they "need income," Nic explains why that thinking often...

With tax deadlines approaching, we talk about the real-world complexity of Roth conversions—starting with a detailed caller scenario that highlights how confusing the rules can actually be. Brian and Jeremiah walk through how taxes are paid on conversions, when estimated payments are required, and unpack lesser-known strategies like the "withhold and replace" approach and the 60-day rollover rule....

Many investors believe they have a financial plan. When in reality, they simply have an investment account... Nic Daniels and Alex Lundgren break down the critical difference between investment management and true financial planning. While investment management focuses on selecting funds and tracking performance, real planning goes much deeper—covering tax strategy, retirement income, risk managem...

With markets entering correction territory , Brian and Jeremiah break down what recent volatility actually means and how investors should respond without making emotional mistakes. They explain how rising oil prices, inflation expectations, and interest rate uncertainty are driving market swings, and why having a strategy in place matters more than reacting to headlines. The conversation then shif...

Most couples assume taxes will decrease when one spouse passes away, but in many cases, the opposite happens. In this podcast, Nic focuses on the often-overlooked "Widow's Tax Penalty" and why it can create a significant tax burden for surviving spouses. When filing status shifts from married filing jointly to single, tax brackets shrink—often resulting in higher taxes on similar or even reduced i...

As markets flirt with correction territory and geopolitical tension continues to drive uncertainty around oil, inflation, and interest rates, Brian and Jeremiah focus on what investors should actually do when volatility rises. Rather than reacting to headlines, they explain why market pullbacks create opportunities—from tax-loss harvesting to strategic gifting—and how disciplined planning can turn...

With oil prices pushing above $100 amid escalating Middle East tensions, Brian Wiley and Jeremiah Bates open the show by breaking down what geopolitical shocks can mean for markets, inflation, and investor sentiment. They discuss more about how headlines surrounding energy prices and global conflict can amplify volatility, but also explain why long-term investors should focus more on portfolio str...