Markets dont 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.They reflect on the shar

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

What does it really take to get a MedTech startup from concept to market? In this episode, Matt sits down with Karandeep Singh Badwal, a UK-based consultant, content creator, and host of The Medtech P

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 t

Roth conversions can be a powerful tax strategy, but are they the right move when youre just about to retire? In this video, Matt walks through a real-life case study to test that very question. Using Jerry and Ruth Crawfords $7.3 million portfolio, he

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. M

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 consi

Your companys IPO can be a major financial opportunity, or a costly misstep if youre 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 compensat

A new tax bill has officially passed (youve probably heard it mentioned as the Big Beautiful Bill). While most headlines are focused on the politics, were zeroing in on what it means if youre retired, a business owner, have stock compensation, or are

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 tha