3 Times Selling Company Stock Makes More Sense Than Holding
You’ve probably heard the advice to hold on to your company stock. It feels logical- you work there, you believe in the business, and selling can feel disloyal. But what if that advice is actually putting your financial future at risk?
By Matthew Nelson
January 22, 2026
351 Exchanges & Exchange Funds: Diversify Portfolio & Skip Taxes
Diversifying a large stock position without triggering a massive tax bill can feel impossible, but there are advanced strategies designed specifically for this challenge. In this episode, Matt breaks down two powerful but often misunderstood tools: the 351 Exchange and the Exchange Fund.
By Matthew Nelson
November 20, 2025
Launching a MedTech Company? Funding, Regulation & Success Strategies with Karandeep Singh Badwal
In this episode, Matt sits down with Karandeep Singh Badwal, a UK-based consultant, content creator, and host of The Medtech Podcast. They explore the realities of launching and funding MedTech ventures.
By Matthew Nelson
November 6, 2025
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
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
2025 in Review: What’s Ahead for Investors in 2026?
Markets don’t move in straight lines, and 2025 proved that once again. In this episode, Matt sits down with Matthew Finley to walk through their 2026 Market Outlook and what investors should realistically expect in the year ahead.
By Matthew Nelson
January 8, 2026