Don’t Let Bad Timing Ruin Your Retirement Savings
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.
By Matthew Nelson
October 2, 2025
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. Using Jerry and Ruth Crawford’s $7.3 million portfolio, he explores different strategies, from converting everything at once to filling tax brackets little by little.
By Matthew Nelson
September 18, 2025
Mega Backdoor Roth Explained: The Tax-Free Growth Strategy for High Earners
Have you ever maxed out your 401k and thought, ‘Where else can I put money that grows tax-free?’ If you’re a high earner, especially working in MedTech or the corporate world, this strategy might change the way you save for retirement. Matt breaks down one of the most powerful (and often overlooked) retirement strategies available today: the Mega Backdoor Roth.
By Matthew Nelson
August 28, 2025
Plan Your Stock Compensation for the Year
Stock compensation can be one of the most rewarding benefits your employer can offer you. However, it also carries complexities that require careful planning. Whether you’re dealing with restricted stock units (RSUs), stock options, or performance…
By Matthew Nelson
August 19, 2025
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
