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.
By Matthew Nelson
August 18, 2025
Going Public? 5 IPO Planning Tips for Employees with Stock Comp
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.
By Matthew Nelson
July 31, 2025
The One Big Beautiful Bill Breakdown
A new tax bill has officially passed (you’ve probably heard it mentioned as the “Big Beautiful Bill”). While most headlines are focused on the politics, we’re zeroing in on what it means if you’re retired, a business owner, have stock compensation, or are thinking about estate planning. The decisions you make in the next year or two could significantly affect how much of your wealth you keep and how much goes to Uncle Sam.
By Matthew Nelson
July 24, 2025
Arctic Wolf: An Employee Stock Options Case Study
Questions you are probably asking yourself if you have stock options from Arctic Wolf: “What the heck are these? What do I do with them? Do they have value?” Today, I am going to break these…
By Jacob LaRue
July 17, 2025
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.
By Matthew Nelson
July 17, 2025
What the One Big Beautiful Bill Means for Your Taxes
On July 4th President Trump signed into law the One Big Beautiful Bill. This marked a new era to our nation’s tax code. The bill covers a wide variety of items ranging from government spending to…
By Jacob LaRue
July 10, 2025
Arctic Wolf Stock Options: What You Need to Know
Part of your compensation package at Arctic Wolf may include stock options. However, for employees of private companies like Arctic Wolf, navigating the complexities of stock options can feel daunting. Decisions about whether to exercise options…
By Jacob LaRue
May 22, 2025
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.
By Matthew Nelson
May 8, 2025
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.
By Matthew Nelson
May 1, 2025
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.
By Matthew Nelson
April 24, 2025
