Episodes

Should you change your retirement investments because an expert says the market is headed for a downturn? What happens if the market moves in the opposite direction? With economic headlines, financial commentary, and conflicting opinions coming from every direction, deciding which information deserves your attention can be difficult, especially when you’re nearing retirement. In this episode of Ramp Up To Retirement, Dan Reese explains why having more financial data doesn’t necessarily provide g...

Your parents’ retirement experience can reveal lessons that are difficult to see while you’re still working. What has changed between their generation and yours, and which financial habits still hold up? In this episode, Dan Reese, CFP®, explains how retirement planning has changed across generations and what you can learn by asking your parents thoughtful questions. He covers the shift from pensions to personal savings, the healthcare gap before Medicare, longer life expectancies, lifestyle cre...

Choosing between Roth and pre-tax retirement savings can feel simple until taxes, healthcare costs, income changes, and future withdrawals enter the picture. In this episode, Dan Reese, CFP®, explains how Roth and pre-tax 401(k) contributions affect when you pay taxes and why the more appropriate choice may change throughout your career. He covers why lower-income years may favor Roth contributions, when pre-tax savings may become useful, and how Roth assets can provide added flexibility in reti...

When should you claim Social Security, at 62, full retirement age, or 70? The answer can affect more than your first monthly payment, including your future income, taxes, portfolio withdrawals, and the benefit available to a surviving spouse. In this episode, Dan Reese, CFP®, explains how Social Security benefits differ when claimed at age 62, full retirement age, or age 70. He examines break-even calculations, annual cost-of-living adjustments, life expectancy, earnings limits, and household cl...

If you’re approaching retirement with a large traditional IRA, deciding whether to convert to a Roth account can affect your future taxes, Medicare costs, and what your heirs receive. How do taxes, Medicare costs, retirement income, and estate planning all connect when making this decision? The right decision depends on your situation, not just what tax rates are doing. In this episode, Dan Reese, CFP®, explains how recent tax law changes have shifted the reasons people may evaluate Roth convers...

Are you getting financial advice, or are you simply getting investment updates? Many people build strong relationships with their financial advisor, but that doesn’t always mean every part of their retirement plan is being addressed. Knowing what questions to ask can make a meaningful difference before small planning gaps become bigger problems. In this episode, Dan Reese, CFP®, explains how to evaluate whether your financial plan is covering the areas that matter most. He shares the 3-lane plan...

Estate planning is often treated as a task to complete later, but many of the biggest financial decisions begin long before legal documents are signed. How can tax planning, retirement income planning, and investment decisions work together to support your long-term goals while potentially improving how assets are transferred? In this episode, Dan Reese explains why estate planning is much more than wills and legal paperwork. He shares how investment planning, retirement income planning, and tax...

Selling your business may feel like the finish line, but for many owners, it can mark the start of a completely new chapter. One surprising statistic discussed in this episode: nearly 70% of business owners report regretting the sale within a year. In many cases, owners may feel unprepared for what comes next. In this episode, Dan Reese wraps up the business exit-planning series by exploring the emotional, financial, and personal realities that follow a business sale. From the shift in identity ...

Selling a business involves both financial and personal considerations, and the transition path you choose may influence your long-term business, employee, and personal goals. In this episode, the seventh in the business exit planning series, Dan Reese walks through the most common exit paths available to business owners, including strategic sales, private equity, ESOPs, management buyouts, and family transitions. He breaks down the pros and cons of each, explains how payment structures like ear...

What contributes to a business’s value when it’s time to step away? Is it just the numbers, or is there something deeper that drives what buyers may be willing to pay? In this episode, Dan Reese breaks down part 6 of the business exit series, focusing on ways to potentially enhance business value before a sale. He explains why financials alone do not tell the full story and introduces four key drivers, human, customer, structural, and social capital, that can influence valuation. Dan walks throu...

Growth gets most of the attention, but what happens when hidden risks start to impact what an outside buyer may consider when evaluating your business? What would an outside buyer see that you might be overlooking today? In this episode, Dan Reese breaks down the fifth part of the business exit series, focusing on how business owners can help address risks that may affect value before a sale. He explains how risks like key person dependency, customer concentration, and weak systems may influence...

Most business owners assume they know what their company is worth, but that number is often far from reality. What factors actually influence value, and how can small changes today impact what you walk away with later? In this episode, Dan Reese continues the business exit series, breaking down how business owners can better understand valuation and prepare for a future exit. He explains the role of EBITDA, the risks buyers evaluate, and how leadership depth and systems impact value. The convers...

Thinking about selling a business is one thing; knowing what you actually need from it is another. How do you move from guessing a number to having greater clarity about your financial future and lifestyle? In this episode, Dan Reese breaks down Part 3 of the business exit series, focused on defining “your number” through personal financial planning. He explains how business owners can identify their true financial needs, account for concentration risk, and understand the gap between what they h...

What happens when the title you have carried for decades suddenly disappears? How do you prepare for the emotional shift that comes after stepping away from your business? In this episode, Dan Reese, CFP®, continues the business exit series by focusing on the personal side of transition. He explains why identity, routine, and purpose play such a critical role in life after a sale. Dan shares practical exercises to help business owners design their ideal week, align with their spouse, and prepare...

Thinking about stepping away from your business someday? The real question is whether you are preparing to leave or preparing to grow. In this episode, Dan Reese, CFP®, kicks off a multi-episode series on exit planning for business owners. He introduces the concept of value acceleration as a proactive alternative to traditional succession planning and explains why many owners may overestimate what their business is worth while underestimating how much they rely on it financially. Dan breaks down...

Most people see one or two meetings a year and assume that’s the whole picture. But real planning is happening year-round, often when no one is sitting across the table. In this episode, Dan Reese, CFP, pulls back the curtain on how an annual service calendar guides financial planning throughout the year. He walks through how winter tax planning sets the foundation, how spring portfolio reviews and tax strategies are handled, and why summer and fall are critical for scenario planning, insurance ...

Retirement tax decisions often feel simple on the surface, but the ripple effects can last decades. The real question is not whether taxes will be paid, but when, how, and by whom. In this episode, Dan Reese, CFP®, walks through how Roth conversions, a taxable event, can fit into a broader retirement and estate plan for high-income earners. He explains when conversions may help manage future tax exposure, Medicare premiums, and inherited IRA issues. The conversation also covers market downturns,...

Most business owners say they feel prepared to step away, but available data suggests gaps in readiness. In this episode, Dan Reese breaks down insights from the National State of Owner Readiness Report and explains common areas where small and mid-sized business owners may lack preparation for a significant financial transition. With a large portion of many owners’ net worth tied up in their business, exit planning often involves business, personal, and financial considerations. Dan walks throu...

Online platforms surface a steady stream of financial content, often from influencers whose guidance is not tailored to individual situations. In this episode of Ramp Up to Retirement, Dan Reese discusses the difference between broad online commentary and fiduciary planning, and how that gap can affect real retirement decisions. He walks through examples involving Roth conversions, Social Security timing, and investment choices that are sometimes framed too broadly in short-form content. What to...

Gold is in the headlines again. Prices are higher this year, we see gold ads on TV, and fear-based marketing may be convincing more retirees to convert their savings into precious metals. But is gold truly as safe as it’s perceived to be, or are investors falling for glitter over substance? Dan Reese delivers a calm, factual look at the emotional and financial realities of gold investing. From physical bars to ETFs, Dan explains the pros, cons, and costly surprises many people overlook, especial...

Mark and Susan thought they did everything right: no debt, over a million saved, markets trending up. But one well-intentioned gift to their kids set off a chain of financial consequences they didn’t anticipate. In this episode, Dan Reese is joined by Brent Oliver for a hypothetical case study exploring how using the concept of a financial “postmortem”, an exercise in looking back to uncover what went wrong and why. You’ll hear how early retirement optimism, overconfidence, and lack of a coordin...

Did you know that even one extra dollar of income in retirement may trigger higher taxes, Medicare premiums, or health insurance costs? This week, Dan Reese explains common retirement planning situations where a single extra dollar in income can unexpectedly spike your taxes, Medicare premiums, and insurance costs. From IRMAA surcharges to Social Security taxation rules to ACA subsidy limits, Dan explains how understanding these often overlooked thresholds can help retirees make more informed fi...

One of the biggest risks to your retirement may not be the market. It could be overconfidence. Dan Reese examines the genuine risks of DIY financial planning, particularly in a world inundated with AI tools and financial influencers who oversimplify complex decisions. From emotional investing to overlooked tax landmines and Medicare surprises, Dan breaks down why retirement planning involves more than simply choosing investments. You’ll learn how behavioral biases, sequence-of-return risk, and m...

Most people think the hard part is saving for retirement, but the real challenge begins when the paychecks stop. Dan Reese walks through the crucial mental and financial shift from accumulation to decumulation and why so many retirees get it wrong. From tax surprises and market volatility to emotional roadblocks and overlooked estate planning, Dan breaks down the common pitfalls and shares what it takes to create a truly sustainable income plan. You’ll learn how to map out long-term tax liabilit...