Category: Investment Management
Do Roth Conversions Still Make Sense After Tax Law Changes? (Ep. 35)

Do Roth Conversions Still Make Sense After Tax Law Changes? (Ep. 35)

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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 conversions as part of their retirement planning. He shares how Roth conversions can affect retirement taxes, future required distributions, and the assets passed to heirs. Dan also explains how reviewing your current financial picture, evaluating different tax-bracket scenarios, and coordinating with financial and tax professionals can help clarify the potential trade-offs.

Key points:

  • How Roth conversions can affect retirement taxes, Medicare premiums, and future financial decisions
  • Why recent tax law changes changed the reasons many people consider Roth conversions
  • How inherited retirement accounts can create tax concerns for the next generation
  • Why spreading conversions across multiple years may help manage tax brackets
  • How financial planning connects taxes, income, investments, and estate decisions
  • And more!

This information is not intended to provide specific legal, tax, or other professional advice. For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Converting from a traditional IRA to a Roth IRA is a taxable event.

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How to Know If Your Financial Advisor Is Really Helping You Plan for Retirement (Ep. 34)

How to Know If Your Financial Advisor Is Really Helping You Plan for Retirement (Ep. 34)

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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 planning framework, covering investments, retirement income, and tax planning, and discusses how Social Security, Medicare, estate planning, and long-term tax decisions work together. Dan also explains why planning performance often matters just as much as investment performance when preparing for retirement.

Key takeaways:

  • How fiduciary advice differs from investment-focused conversations and why that distinction matters
  • Why retirement income, tax planning, and investments should work together instead of separately
  • Questions to ask when evaluating whether your advisor is addressing your complete financial plan
  • How Social Security and Roth conversion decisions can influence lifetime retirement taxes
  • Why planning performance may have a greater financial impact than investment returns alone
  • And more!

Converting from a traditional IRA to a Roth IRA is a taxable event.

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Tax-Focused Estate Planning Before Retirement (Ep. 33)

Tax-Focused Estate Planning Before Retirement (Ep. 33)

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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 planning all influence one another through what he calls the three lanes of the financial highway. Dan also explores how Roth conversions, beneficiary designations, charitable giving, and account positioning can affect taxes during retirement and for future generations. 

Throughout the conversation, he emphasizes creating a coordinated strategy while there may still be more planning flexibility.

Key takeaways:

  • How investment, retirement income, and tax planning work together instead of as separate decisions
  • Why estate planning begins with strategy before legal documents are created and updated
  • How Roth conversions may influence taxes paid by both retirees and future beneficiaries
  • Why beneficiary designations and asset location can change long term tax outcomes
  • How coordinated planning may uncover opportunities across multiple financial decisions
  • And more!

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What Happens After You Sell Your Business? (Ep. 32 | Pt. 8)

What Happens After You Sell Your Business? (Ep. 32 | Pt. 8)

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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 that happens after stepping away from daily operations to the challenge of transitioning from entrepreneur to investor, Dan explains why many business owners find that a successful transition involves more than just the valuation.

Dan discusses:

  • Why many business owners experience emotional challenges after selling
  • The difference between building wealth and preserving it
  • How fear and emotion can impact investing after a liquidity event
  • Why tax planning can play an important role before and after a sale
  • And more!

If you’re a business owner thinking about an exit, or already navigating life after one, this episode offers perspective on navigating the transition after a business sale. 

Whether you’re years away from selling your business or already thinking about life after work, this episode offers insight into building a retirement plan designed to align with your financial goals, personal priorities, and long-term legacy.

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Choosing the Right Exit Path for Your Business (Ep. 31 | Pt. 7)

Choosing the Right Exit Path for Your Business (Ep. 31 | Pt. 7)

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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 earnouts and lump sums work, and addresses what buyers are actually looking for. 

Dan also highlights the biggest mistakes owners make, from waiting too long to ignoring tax planning and cultural fit.

Dan discusses:

  • How a strategic sale may result in higher valuations when a buyer sees immediate synergies with your existing business and processes
  • Why private equity may involve a larger upfront payment structure, and how earnouts and equity shares factor into the deal structure
  • How ESOPs may provide tax-related considerations, employee ownership opportunities, and continuity planning benefits for some companies for owners who want a gradual exit
  • Why the highest purchase price may not align with an owner’s broader priorities when legacy, culture, and employee impact matter to you
  • How procrastinating on exit planning and value acceleration may limit flexibility and preparation during a future transition
  • And more!

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Building Business Value Beyond the Numbers (Ep. 30 | Pt. 6)

Building Business Value Beyond the Numbers (Ep. 30 | Pt. 6)

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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 through how leadership, customer structure, internal processes, and reputation can shape buyer perception and future potential. 

Dan discusses:

  • Why two businesses with identical financials can sell for very different prices based on structure and team strength
  • How recurring revenue and customer diversification may support stability and buyer confidence
  • The importance of human capital and building a team that can support long-term business continuity
  • How structural capital, including processes and systems, may improve scalability and transferability
  • Why social capital and reputation can play a role in how buyers evaluate long-term potential
  • And more!

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Managing Business Risk Before an Exit (Ep. 29 | Pt. 5)

Managing Business Risk Before an Exit (Ep. 29 | Pt. 5)

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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 what buyers are willing to pay. 

The conversation highlights practical ways help to identify and manage these risks, including building leadership depth and improving processes. Dan also shares why viewing your business through a buyer’s lens can change how you prepare for an exit.

Key takeaways:

  • How reliance on one person can limit business value and create challenges when transitioning ownership
  • Why customer concentration and inconsistent revenue streams raise concerns for potential buyers
  • The impact of undocumented processes on hiring, training, and overall operational stability
  • How regulatory and legal exposure can influence valuation and ongoing profitability considerations
  • Practical steps to help reduce risk, including leadership depth, audits, and working with specialists
  • And more!

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What Is Your Business Really Worth and How to Increase It Before You Exit (Ep. 28 | Pt. 4)

What Is Your Business Really Worth and How to Increase It Before You Exit (Ep. 28 | Pt. 4)

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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 conversation also highlights emotional bias in pricing and practical ways to strengthen a company over time. Listeners will learn how consistent improvements and proper planning can help support stronger outcomes when it matters most.

Key takeaways:

  • Why many owners misjudge their business value and how a proper valuation helps establish a clearer baseline
  • How emotional attachment can distort pricing expectations and may negatively impact decision-making
  • Why building leadership depth can help reduce perceived risk and increase appeal to potential buyers
  • How EBITDA adjustments provide a clearer view of profitability beyond tax-driven accounting choices
  • Why buyers scrutinize systems, customers, and financials, and what that means for preparation
  • And more!

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What’s Your Number? The Key to Selling Your Business Without Regret (Ep. 27 | Pt. 3)

What’s Your Number? The Key to Selling Your Business Without Regret (Ep. 27 | Pt. 3)

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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 have and what they may need. The conversation also highlights the importance of tax planning, building the right advisory team, and preparing well in advance to help reduce the likelihood of costly mistakes and uncertainty.

Key takeaways:

  • Why business owners should not rely on rough estimates when deciding how much they need from a sale
  • How personal financial planning can reveal true lifestyle costs and hidden benefits from a business
  • The role of concentration risk when most wealth is tied to a single company asset
  • Why taxes and deal structure can significantly reduce what you actually receive after a sale
  • How having the right team helps improve clarity and support more informed decision-making
  • And more!

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Life After the Sale: Designing Your Next Chapter Before You Exit (Ep. 26 | Pt. 2)

Life After the Sale: Designing Your Next Chapter Before You Exit (Ep. 26 | Pt. 2)

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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 emotionally for what comes next. He also discusses research suggesting that many owners experience regret after selling and how intentional planning may help reduce the likelihood of regret.

Key takeaways:

  • Why identity transition is one of the biggest hurdles after selling a business
  • How routine and decision-making impact emotional well-being in retirement
  • The importance of lifestyle design and structuring your ideal week
  • Why spousal alignment and family communication matter before exiting
  • How proactive exit planning strategies can help business owners prepare emotionally and financially for transition
  • And more!

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