Overtime Earnings

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-9051584.1(08/26)(exp.08/30)

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 investors should ask before investing in any IPO and why having a plan matters more than chasing headlines. PPG-9001385.1(08/26)(exp.08/30)

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 sell or hold vested shares and the importance of developing a written strategy based on your individual circumstances. PPG-9051594.1(08/26)(exp.08/30)

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, and why the next phase of AI may shift attention from the companies building the technology to the businesses using it to improve productivity. PPG-9083771.1(08/26)(exp.08/30)

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 Dave discuss how families can prepare for changing roles, organize important documents and account information, clarify who may make key decisions, and communicate intentions before uncertainty creates conflict. PPG-8871254.1(05/26)(exp.05/30)

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-positioned homes can still attract fast and competitive offers, why overpriced properties may sit, and how buyers can prepare before they find the home they want.

The conversation also explores the financial realities facing first-time buyers, move-up buyers, retirees, and families considering helping the next generation purchase a home. Steve also shares important considerations involving condos, solar-panel agreements, remote-work space, and the relationship between employment stability and housing activity. PPG-8990862.1(07/26)(exp.07/30)