Overtime Earnings

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 management professional, and business consultants need to understand the same objectives. PPG-9051562.1(09/26)(exp.09/30)

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 10b5-1 plan may fit into a broader financial strategy. PPG- 9092945.1(09/26)(exp.09/30)

“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(09/26)(exp.09/30)

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 distributions or initiating a rollover. PPG-9021788.1 (08/26) (exp. 08/30)

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, managing wealth with purpose, and creating a life that continues to inspire you long after traditional retirement age. PPG-9043166.1 (08/26)(exp.08/30)

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 over time. PPG-9092980.1(09/26)(exp.09/30)

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! PPG-8976948.1(07/26)(exp.07/30)

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. PPG-8975577.1(07/26)(exp.07/30)