Overtime Earnings

Many investors know about traditional Roth IRAs but are unaware that certain 401(k) plans may allow additional after-tax contributions to be converted into Roth assets. We breakdown how the "Mega Backdoor Roth" strategy can create additional tax-free growth opportunities for eligible participants as well as important steps to determine if it can be implemented as part of your plan. PPG- 9175305.1...

Retirement isn't just about how much you've saved, it's about how you use what you've saved. In this episode, we break down how withdrawal strategies, taxes, and account sequencing can play a major role in retirement income, long-term wealth preservation, and legacy planning. PPG-9031405.1a(09/26)(exp.09/30

Dave and Ken explain how a cash balance plan can supplement a traditional 401(k) and potentially allow eligible, high-income business owners to make substantially larger pre-tax retirement contributions. The conversation covers the types of owners who may be a good fit, how these plans are established and administered, and how they may support retirement catch-up and business-exit planning. We als...

When a child has a disability, learning difference, or complex medical need, families can quickly feel overwhelmed by unfamiliar laws, financial considerations, and difficult decisions. In this episode of Overtime Earnings , we welcome special education attorney Katie Thomas of Ally Legal Planning to explain IEPs, 504 plans, guardianship, ABLE accounts, special needs trusts, and the importance of...

In this Quick Tip Tuesday episode, Ken Handy and David Baker explain how an irrevocable life insurance trust, or ILIT, can own a life insurance policy and they discuss the trade-offs, including giving up control, and handling annual administrative requirements. PPG-9072023.1(10/26)(exp.10/30)

For many business owners, the business is their largest asset. Yet investment planning, taxes, retirement, estate planning, risk management, and the eventual exit are often handled by different professionals operating from separate playbooks. Using football as their playbook, they explore what happens when every coach is calling a different game and why your CPA, attorney, financial advisor, risk...

For corporate executives, directors, and other company insiders, selling company stock can involve significant legal and compliance considerations. A properly established Rule 10b5-1 trading plan can provide a structured way to buy or sell company shares according to predetermined instructions. For insiders managing concentrated company stock, this episode offers a helpful introduction to how a 10...

“Golden handcuffs” refers to valuable employer benefits, such as RSUs, stock options, employee stock purchase plans, and deferred compensation. In this episode Dave and Ken discuss how each form of equity compensation has different tax rules, making proactive and coordinated planning essential. A personalized strategy is also a key factor in working towards your financial goals. PPG-9024313.1(09/2...

Many investors unknowingly roll company stock from a 401(k) into an IRA, potentially missing one of the most valuable tax strategies available. In this episode, Dave and Ken break down Net Unrealized Appreciation (NUA). They discuss eligibility requirements, potential tax savings, common mistakes that can permanently eliminate the opportunity, and why careful planning is critical before taking any...

What does a successful life look like after more than four decades at the highest levels of law, business, and professional sports? Ken and Dave sit down with attorney and sports executive Mark Levinstein for a wide-ranging conversation about the habits that create lasting success. Mark shares lessons on building trust, giving others credit, seeking mentors, preparing for career transitions, manag...

What if appreciated stock could support the causes you care about while potentially creating a more tax-efficient outcome? In this Quick Tip Tuesday, David and Ken explain how a donor advised fund may allow charitably inclined investors to contribute appreciated stock, potentially avoid recognizing capital gains, receive a deduction based on fair market value, and recommend grants to charities ove...

In Part 2 of our asset location discussion, we shift from accumulating assets to strategically using them during retirement. The episode examines how withdrawals from traditional retirement accounts, Roth accounts, and taxable brokerage accounts may produce different tax outcomes. It also explores how retirement income sources can interact with Social Security taxation, Medicare premiums and more!...

Non-qualified stock options, or NQSOs, are a common and flexible form of equity compensation, but exercising them can create an immediate tax obligation. In this Quick Tip Tuesday episode of Overtime Earnings , Ken Handy and David Baker explain how NQSOs work, and the value of coordinating an exercise strategy with qualified tax and financial professionals. PPG-9051607.1(08/26)(exp.08/30)

In this installment of Overtime Earnings, Ken Handy and Dave Baker introduce asset location, the practice of considering which investments are held within tax-deferred, tax-free, and taxable accounts. Using sports and stadium analogies, they discuss how placing investments in account structures that complement their tax and growth characteristics may improve a portfolio’s overall tax efficiency. P...

In this Quick Tip Tuesday episode of Overtime Earnings, we break down incentive stock options, or ISOs, in plain English. They explain how ISOs work, why their potential tax treatment can be attractive, and the holding-period rules that may apply. The key takeaway: ISOs can be a valuable wealth-building tool, but exercising them without a coordinated strategy may lead to costly surprises. PPG-9051...

No championship is won by one player, and financial success should not be managed by one person operating alone. Using sports as the foundation, we explore why every successful person needs trusted professionals who are willing to deliver candid advice, identify blind spots, and communicate with one another towards a common goal. PPG-8965795.1(07/26)(exp.07/30)

Ever wondered if investment losses can become part of your tax strategy? In this episode we talk about ways to use investment losses to offset gains in the portfolio which can help keep alignment with a long-term strategy. PPG- 9001606.1(08/26)(exp.08/30)

The latest wave of IPOs has many investors asking whether they should jump in before "the next big thing" takes off. In this episode, Dave and Ken discuss IPOs through a Warren Buffett-inspired lens, exploring why investors should be cautious of hype, focus on valuation and fundamentals, and remember that patience often leads to better investment decisions. They also share practical questions inve...

Restricted Stock Units may look simple, but their tax implications and concentration risks can catch employees and executives off guard. In this Quick Tip Tuesday episode, Dave Baker and Ken Handy explain how RSUs vest, when they become taxable, how post-vesting gains are treated, and why withholding may not cover the full tax obligation for higher-income earners. They also discuss the decision to...

In this episode of Overtime Earnings, we sit down with Brian Mulberry, Chief Market Strategist at Zacks Investment Management, for a wide-ranging conversation about what may be happening beneath the market’s daily noise. The conversation also explores the massive investment in artificial intelligence infrastructure, how investors might distinguish productive growth spending from balance-sheet risk...

In this Quick Tip Tuesday episode of Overtime Earnings, David Baker and Ken Handy explain the mechanics of a retirement plan rollover in plain English. They discuss how the method used to transfer retirement funds can affect tax withholding, deadlines, and the amount ultimately deposited into the receiving account. PPG-9023637.1(08/26)(exp.08/30)

Succession planning is not just for business owners. Every family needs a playbook. In this episode of Overtime Earnings, Ken and Dave explore why conversations about aging parents, family responsibilities, inheritances, and estate intentions are often so difficult, and why waiting until a crisis can make those decisions even harder. Using relatable sports analogies and personal stories, Ken and D...

Welcome to the first Quick Tip Tuesday episode on Overtime Earnings! A shorter episode with big ideas! Ken Handy and David Baker break down one of the most powerful and misunderstood retirement planning strategies: the Roth Conversion. PPG-9001418.1(08/26)(exp.08/30)

Should you buy a home while mortgage rates remain elevated? Is now a good time to sell? And does downsizing actually mean spending less? In this episode we welcome Maryland real estate professional Steve Huffman for a practical conversation about navigating today’s housing market. Steve brings local, on-the-ground perspective from Howard County and the broader Maryland market. He explains why well...

Most entrepreneurs know how to compete but are they operating with a coordinated tax strategy, or simply reacting after the season ends? In this episode Ken Handy and David Baker use the language of sports to make tax planning more approachable. They discuss why entrepreneurs may benefit from treating their tax advisor like a coach, watching important deadlines, coordinating across their professio...