Real Money Pros

Selling a business can be one of the biggest financial events of an owner's life, but getting a good deal takes more than simply finding a buyer.

This week, Jeremiah Bates is joined by Rob Wolfe, Managing Director at Apollon Wealth Management, to discuss what makes a business attractive to potential buyers and how owners can prepare years before an exit. They cover the difference between owning a practice, a business and an enterprise, along with owner dependency, recurring revenue, customer concentration, clean financials, due diligence and the factors that can ultimately influence what someone is willing...

What do rising Treasury yields actually mean for your portfolio, and should market volatility change the way you're investing?

This week, Nic Daniels and Alex Lundgren start with September market volatility, rising Treasury yields and the relationship between bond prices and yields, while explaining why investors should be careful about making long-term portfolio decisions based on elections, geopolitical events or short-term market swings.

A listener preparing to retire after 37 years with the Postal Service asks about using a Social Security survivor benefit while delaying her own benefit, along with coordinating her pension and inherited IRA.<...

Your retirement projection is green. The Monte Carlo analysis shows a 95% probability of success. Everything looks good. So what could still go wrong?

A retirement plan is only as good as the assumptions behind it—and real life rarely follows those assumptions perfectly.

In this episode, we look beyond investment returns at some of the risks that can change an otherwise strong retirement plan: long-term care, the early death of a spouse, living longer than expected, helping family, lifestyle creep, liquidity problems, market declines early in retirement, and changing tax laws.

More importantly, we...

What does financial planning actually mean beyond managing an investment portfolio?

Jeremiah Bates and Nic Daniels are joined by Bob Ruelle, Senior Vice President of Financial Planning at Apollon Wealth Management, to walk through how an experienced planner approaches a client's entire financial picture. Bob explains why good planning starts with understanding a person's goals, lifestyle, concerns and priorities before recommending anything—and why the financial plan itself should ultimately be the benchmark for whether a strategy is working.

The guys cover tax planning, Roth conversions, retirement withdrawal strategies, RMDs, Social Security, Medicare IRMAA, insurance, ri...

Estate planning is often built around a familiar structure: your spouse makes decisions for you, your children eventually inherit your assets, and a responsible family member serves as executor or trustee.

But what happens when you don't have children—or an obvious person to fill those roles?

In this episode, we discuss how estate planning changes when there aren't default answers. Who should make financial or healthcare decisions if you're incapacitated? Who should administer your estate? And if leaving a traditional inheritance isn't part of the plan, what do you actually want your wealth to ac...

Brian Wiley and Alexandra Lundgren are joined by Eric Sterner, Chief Investment Officer at Apollon Wealth Management, for an extended conversation on portfolio strategy and where he sees opportunities developing across the investment landscape.

Eric discusses why the AI investment story extends well beyond technology stocks, with potential beneficiaries across healthcare, utilities, industrials, materials and the infrastructure needed to support continued AI growth. The conversation also explores healthcare and biotech, portfolio diversification, private equity and private credit, and the tradeoffs investors should understand before allocating money to alternative investments.

A listener considering SpaceX and XRP...

You need cash for a major purchase or investment opportunity. You could sell appreciated investments and potentially trigger capital gains taxes—or borrow the money and leave your investments alone.

Borrowing can sound like the obvious choice. After all, loan proceeds generally aren't taxable income. But what happens when it's time to pay the loan back?

In this episode, Nic breaks down the planning behind selling investments versus borrowing, including when debt can be an effective short-term tool, when paying the tax may actually leave you better off, and why avoiding taxes today shouldn't be the...

The financial world looks very different than it did just a few years ago. Brian Wiley is joined by Steve Cilley of Ataraxis PEO for a wide-ranging conversation about how changes in technology, the workplace, housing, and the economy are reshaping the way people build and protect wealth.

The show begins by looking back at the economic fallout from COVID, including stimulus, inflation, changes in employee expectations, and the lasting impact on businesses. A listener with gains in XRP brings the conversation into cryptocurrency, tax-loss harvesting, cost-basis tracking, cold wallets, and the challenges of proving and protecting...

Where you invest your money is only part of the equation. Which accounts hold those investments, how they're taxed, and where you eventually take income from can have just as much impact on your financial plan.

Brian Wiley and Jeremiah Bates begin with a listener looking for conservative retirement income, breaking down Treasury bills, notes and bonds, buying at auction versus the secondary market, bond ladders, CDs, annuities, interest-rate risk, and why avoiding state income tax shouldn't be the only consideration when choosing an investment.

The conversation then turns to asset location and retirement income—ho...

For many entrepreneurs, their business is their largest financial asset, but very few know what it's actually worth or what it takes to maximize its value before an exit.

This week, our team is joined by Jeff Szczypinski of WR Valuation for an in-depth discussion on business valuations and why they're about much more than determining a sale price. They explain how valuations support retirement planning, succession planning, estate planning, buy-sell agreements, gifting strategies, and ownership transitions. The conversation also covers the biggest drivers of business value, including management teams, key-person risk, customer concentration, financial records, and...

Selling a business is one of the largest financial events many entrepreneurs will ever experience... But most owners spend years building their company without spending nearly enough time planning how they'll eventually leave it.

Jeremiah and Nic discuss why successful business exits begin long before a purchase offer arrives. They explain why business owners should start planning two to three years before selling, the importance of obtaining a professional business valuation, preparing financial records for buyer due diligence, building enterprise value instead of simply generating income, and coordinating your CPA, attorney, valuation specialist, and financial advisor throughout...

Owning an annuity you no longer like does not automatically mean surrendering it is the right decision.

Nic has the discussion of how to evaluate an annuity that no longer seems to fit your retirement plan. He walks through the reasons investors become dissatisfied with their contracts, the questions to ask before making a change, and the different options that may be available. Depending on the contract and your circumstances, the answer could be to keep the annuity, wait for surrender charges to expire, take partial withdrawals, complete a 1035 exchange, begin using its income features, or surrender i...

Retirement taxes are rarely as simple as people expect, and making the wrong withdrawal at the wrong time can have consequences far beyond your tax bill.

In our first hour, Jeremiah Bates and Alex Lundgren explain how IRA withdrawals, pensions, Social Security, brokerage accounts, Medicare IRMAA surcharges, and capital gains work together to shape your lifetime tax picture. They discuss why major purchases, home remodels, and other large withdrawals deserve careful planning to avoid unnecessary taxes and higher Medicare costs.

The conversation later shifts to Social Security planning. The hosts cover when to claim benefits...

Whether you're starting a business, growing one, or preparing to exit, the financial decisions you make today can have long-term tax and estate planning consequences.

In Hour 1, Brian Wiley and Jeremiah Bates explain the differences between LLCs and S Corporations, when an S Corp election may make sense, how business structure affects taxes and liability, and why business owners should coordinate their entity planning with their estate plan. They also discuss cost basis, inherited assets, and avoiding costly mistakes before they happen.

Hour 2 shifts to investing, covering concentrated stock positions, strategies for managing highly appreciated...

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 for additional flexibility around taxes, portfolio customization, and managing highly appreciated assets.

You'll learn how direct indexing differs from traditional index investing, why tax-loss harvesting is only part of the story, and...

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 retirement planning, including how to coordinate 401(k)s, Traditional IRAs, HSAs, and Roth conversion strategies to improve tax efficiency. Brian explains why retirement accounts should be viewed both individually and as part of one comprehensive financial plan, while also...

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 differences between Medicare and Medicaid, the true cost of care, common misconceptions about qualifying for benefits, and why so many families find themselves overwhelmed when a loved one suddenly needs assistance.

The discussion explores re...

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 really means to be wealthy, how to think about financial independence, and why having a plan matters more than chasing the next investment opportunity.

The second hour focuses on retirement income planning and highly appreciated assets, particularly rental properties. They discuss...

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 planning issue approaching at the end of 2026: Qualified Opportunity Zone (QOZ) investments. The guys explain why deferred gains from these investments are becoming taxable, the planning opportunities available before the deadline, and what investors sh...

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 growing importance of digital assets, and the challenges families can face when trying to access online accounts, digital photos, cloud storage, payment apps, and other assets that didn't exist when many estate plans were originally created.<...

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, professional fiduciaries, pet trusts, digital assets, online accounts, passwords, and why failing to plan can leave critical decisions in the hands of the court.

The second hour shifts to a major market...

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 isolation.

They explores sequence-of-return risk, retirement spending assumptions, inheritance surprises, and the reality that successful retirement planning requires far more than simply hitting a target number.

Later in the...

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 automated distributions to cash reserves, taxes, Roth flexibility, and income coordination, Nic explains what retirement income actually looks like in the real world and why it's often much more complex than simply "living off dividends." He...

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.

From there, the show moves into retirement planning mistakes—how improper 401(k) rollovers can trigger unnecessary taxes and penalties, why understanding account rules matters, and when consolidating scattered retirement accounts makes sense.

The hosts also...

"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 coverage, bridge employment, and self-funding healthcare costs, Nic walks through the high-level options people should be aware of.

But this conversation goes beyond just healthcare, because depending on how retirement income is structured, healthcare costs may be i...

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 for benefits. The conversation covers in-home care, assisted living, memory care costs, spousal asset protection strategies, the five-year lookback rule, and why certain estate planning decisions can accidentally create Medicaid problems later on.

Going...

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 to generate reliable income in retirement.

The conversation centers on a key idea: Growth doesn't solve income. Without a plan, big gains can actually increase risk by...

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, this conversation focuses on how small decisions today can create bigger consequences down the road.

He also shares real examples, including helping a child with a down payment and a situation wh...

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 Security—how a system that started at 1% contributions grew to over 15%, why it's under pressure, and what would actually have to change to keep it functioning. They challenge common fears arou...

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 planning mechanics, breaking down how wills vs. trusts actually work, why co-trustee structures can create logistical nightmares, and how poor coordination leads to delays, legal headaches, and family tension (even when intentions were...

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 opportunities.

Nic walks through how these decisions impact your ability to adapt to life changes, manage taxes, respond to market opportunities, and leave assets to heirs. He also explains why focusing...

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 planning basics, including when simple tools like transfer-on-death designations work—and when they fall short.

A standout segment features a real listener story about naming multiple co-trustees, which led to mo...

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 falls short.

From investment responsibility and market risk to tax flexibility and long-term income planning, both options come with trade-offs that extend far beyond the initial decision. He also highlights factors...

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.

The show also covers a second caller navigating a pension lump sum, breaking down rollover options, how to access funds without unnecessary penalties, and strategies like 72(t) distributions. Along the way, the hosts explain why even simple financial de...

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 management, estate coordination, and life transitions.

They discuss common scenarios where portfolios have grown successfully over time, but clients lack a clear plan for how to turn those assets into sustainable income. From tax-efficient withdrawal strategies and Roth conversions to planning for ma...

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 shifts into actionable tax and investment planning. The guys walk through strategies like tax-loss harvesting, managing concentrated stock positions, and why reducing taxes can be just as impactful as chasing higher returns. They also highlight commonly missed opportunities, including properly funding...

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 income.

Nic explains how income sources like IRAs, Required Minimum Distributions (RMDs), and certain pensions may remain unchanged, while Social Security benefits are reduced. This combination can create what's known as "tax compression," wh...

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 short-term declines into long-term advantages.

The show then shifts into practical, real-world financial planning conversations. The hosts walk through how to handle inheritances, including what happens to debt, how probate works, and why some assets may need to be liquidated despite emot...

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 structure and diversification rather than reacting emotionally to short-term news cycles.

The conversation then shifts into deeper retirement planning strategy. Using real-world experiences, the guys walk through Roth conversion planning, including how investors with large IRA balances should think...

Long-term care is one of the biggest financial risks retirees face... yet it's rarely discussed until a crisis happens. In this podcast hosted by Nic Daniels, he explains what long-term care actually is, why it can be so expensive, and the common misconceptions surrounding who pays for it. Many retirees assume Medicare will cover these costs, but in reality most long-term care expenses must be paid out of pocket unless someone qualifies for Medicaid after depleting much of their assets.

Nic walks through the different ways families approach this challenge, including self-funding care, traditional long-term care insurance, a...