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 real-world planning considerations, including asset protection strategies, the five-year lookback period, spousal protections, estate recovery rules, and the challenges families face when trying to navigate the complicated system on their own.

Guests:

Brooke Baker & Jessica Young

Legacy Navigation

https://legacynavigate.com/

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

—————————————————————

Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

—————————————————————

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 capital gains concerns, 1031 exchanges, Delaware Statutory Trusts (DSTs), step-up in basis rules, and strategies for investors who want to simplify their lives without creating unnecessary tax consequences. They also cover Treasury bills, retirement withdrawal planning, income-focused investing, and how to evaluate whether your assets are positioned to support your long-term goals.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

Hosts:

Jeremiah Bates & Brian Wiley

—————

Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

—————————————————————

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 should be doing now to prepare.

The show also covers donor-advised funds, highly appreciated stock strategies, the differences between flat-fee planning and traditional asset management, and practical retirement tax planning topics including required minimum distributions (RMDs), qualified charitable distributions (QCDs), Roth conversions, and Medicare-related planning opportunities.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

Hosts:

Jeremiah Bates & Nic Daniels

—————

Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

—————————————————————

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.

We also discuss the difference between legal authority and practical access, why estate planning should be reviewed periodically, and simple steps families can take to reduce confusion and stress for loved ones.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

—————————————————————

Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

—————————————————————

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 story: SpaceX's highly anticipated IPO. Jeremiah and Alex break down how IPOs actually work, why many investors misunderstand them, the risks of buying into market hype, and how SpaceX could eventually impact index investors and retirement accounts through future index inclusion.

The final hour focuses on practical planning decisions, including pension maximization strategies, large income windfalls from business sales and acquisitions, Medicare and tax planning considerations, and tax gain harvesting opportunities for investors sitting on significant unrealized gains.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

Hosts:

Jeremiah Bates & Alex Lundgren

—————

Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

—————————————————————

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 show, Jeremiah and Alex tackle another area where people often misunderstand the rules: company stock compensation. They break down how RSUs, stock options, and employee stock purchase plans work, why taxes can catch employees off guard, and the planning opportunities available when company stock becomes a meaningful part of your net worth.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

Hosts:

Jeremiah Bates & Alex Lundgren

—————

Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

—————————————————————

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 also dives into the emotional side of retirement income planning, including why so many people struggle with touching principal, spending from their own assets, and maintaining confidence once the steady paycheck disappears.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

—————————————————————

Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

—————————————————————

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 tackle highly appreciated stock positions, Roth conversion strategy after age 65, Medicare premium impacts, Social Security coordination, and tax-efficient ways to unwind concentrated positions.

The broader theme throughout the episode is simple: many of the most expensive financial mistakes are completely avoidable with proper planning…

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

Hosts:

Jeremiah Bates & Nic Daniels

—————

Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

—————————————————————

"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 impacted by ACA subsidies, tax strategy, and withdrawal planning decisions. Nic also shares a real planning example involving a household looking to retire early and how outside assets—not retirement accounts—helped create flexibility in bridging the gap to Medicare.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

Hosts: Nic Daniels

—————————————————————

Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

—————————————————————

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 into the second hour, Jeremiah and Alex pivot into another major planning blind spot: letting taxes dictate investment decisions. They discuss concentrated stock positions, large unrealized gains, rental property sales, 1031 exchanges, Medicare IRMAA surcharges, and why many investors hold onto assets longer than they should simply because they fear the tax consequences.

Throughout the show, the bigger theme remains the same: most financial problems become significantly harder when planning is delayed. Whether it's long-term care, estate coordination, taxes, or investment decisions, this show focuses on why proactive planning matters before life forces the issue.

Listen, Watch, Subscribe, Ask!

https://www.therealmoneypros.com

Hosts:

Jeremiah Bates & Alex Lundgren

Guests:Brooke Baker, RN & Jessica Young, MSW

Co-Founders of Legacy Navigation

https://legacynavigate.com

—————————————————————

Ataraxis PEO

https://ataraxispeo.com

Tree City Advisors of Apollon:

https://www.treecityadvisors.com

Apollon Wealth Management:

https://apollonwealthmanagement.com/

—————————————————————