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?
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.
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.
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 Podcast. They explore the realities of launching and funding MedTech ventures.
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.
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.
This episode, Matt breaks down one of the most powerful (and often overlooked) retirement strategies available today: the Mega Backdoor Roth.
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.
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.
tax law changes, QSBS, AMT relief, estate tax planning, retirement strategy, QBI deduction, small business owners, financial planning, OBBB, One Big Beautiful Bill