Did you know two investors could earn the same average return, pay the same fees, and still retire with very different outcomes? In this episode, Matt explains why sequence of returns risk is one of the most important concepts to understand within 5–7 years of retirement.
Roth conversions can be a powerful tax strategy, but are they the right move when you’re just about to retire? In this video, Matt walks through a real-life case study to test that very question.
This episode, Matt breaks down one of the most powerful (and often overlooked) retirement strategies available today: the Mega Backdoor Roth.
Would you ever pay more to the IRS… on purpose? Sometimes the smartest move in retirement planning is the one that feels most counterintuitive, like voluntarily paying more taxes now. In this episode, Matt breaks down why certain high earners should consider a Roth 401(k) conversion during a lower-income year- if their plan allows it.
Your company’s IPO can be a major financial opportunity, or a costly misstep if you’re not prepared. In this episode, Matt walks you through what really happens when your private company goes public, and the five things every employee with stock compensation needs to know before making a move. It’s often more complex than most people realize, so it pays to be prepared.
tax law changes, QSBS, AMT relief, estate tax planning, retirement strategy, QBI deduction, small business owners, financial planning, OBBB, One Big Beautiful Bill
In this episode, Matt dives into one of the most common forms of equity compensation: Restricted Stock Units (RSUs). If your company just handed you some stock, you may be asking yourself, “What now?” Matt walks through three key questions that will help you move forward with confidence. He also shares practical tips for tracking your vesting schedule and deciding whether to hold or sell your shares.
Roth 401k contributions can be a powerful tool, but only if you know how to use them wisely. In this episode, Matt shares practical tax strategies for deciding when, why, and how to contribute to a Roth 401k through your employer plan.
Medtronic offers one of the most generous benefits packages in the industry, but many employees aren’t using those benefits to their full potential. In this episode, Matt highlights three valuable but often overlooked Medtronic benefits beyond the standard 401(k). These include the Employee Stock Purchase Plan (ESPP), Health Savings Accounts (HSAs), and optional long-term disability insurance.
In this episode, Matt and Jacob unpack a listener question about how to move forward after being forced into retirement earlier than expected. They walk through key considerations for anyone in a similar situation: how to handle severance and stock options, when (or if) to pay off a mortgage, how to approach early healthcare coverage before Medicare kicks in, and whether finding part-time work or consulting could be part of the solution.