Should You Convert to a Roth Before 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.
Mega Backdoor Roth Explained: The Tax-Free Growth Strategy for High Earners
This episode, Matt breaks down one of the most powerful (and often overlooked) retirement strategies available today: the Mega Backdoor Roth.
Why High Earners Should Sometimes Pay MORE Taxes- On Purpose!
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.
Going Public? 5 IPO Planning Tips for Employees with Stock Comp
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.
The One Big Beautiful Bill Breakdown
tax law changes, QSBS, AMT relief, estate tax planning, retirement strategy, QBI deduction, small business owners, financial planning, OBBB, One Big Beautiful Bill
You Just Got Some RSUs- Now What?
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: Smart Moves You’re Missing
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 Benefits Employees Miss Out On
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.
Forced Into Retirement Early – Now What?
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.
Can You Build a Tax-Free Retirement Fund with an HSA?
Are Health Savings Accounts one of the best tax-advantaged accounts out there? Can you really stockpile a massive balance and use it tax-free in retirement? Today, Matt and Jacob will explain why HSAs can be one of the most power-ful tools for long-term, tax-advantaged growth and why using it wisely takes more than maxing out your contributions.