Episodes

  • 351 Exchanges & Exchange Funds: Diversify Portfolio & Skip Taxes

    351 Exchanges & Exchange Funds: Diversify Portfolio & Skip Taxes
    Nov 20 2025
    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.
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    6 mins
  • Launching a MedTech Company? Funding, Regulation & Success Strategies with Karandeep Singh Badwal

    Launching a MedTech Company? Funding, Regulation & Success Strategies with Karandeep Singh Badwal
    Nov 6 2025
    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.
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    31 mins
  • Don’t Let Bad Timing Ruin Your Retirement Savings

    Don’t Let Bad Timing Ruin Your Retirement Savings
    Oct 2 2025
    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.
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    13 mins
  • Should You Convert to a Roth Before Retirement?

    Should You Convert to a Roth Before Retirement?
    Sep 18 2025
    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.
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    12 mins
  • Mega Backdoor Roth Explained: The Tax-Free Growth Strategy for High Earners

    Mega Backdoor Roth Explained: The Tax-Free Growth Strategy for High Earners
    Aug 28 2025
    This episode, Matt breaks down one of the most powerful (and often overlooked) retirement strategies available today: the Mega Backdoor Roth.
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    9 mins
  • Why High Earners Should Sometimes Pay MORE Taxes- On Purpose!

    Why High Earners Should Sometimes Pay MORE Taxes- On Purpose!
    Aug 18 2025
    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.
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    8 mins
  • Going Public? 5 IPO Planning Tips for Employees with Stock Comp

    Going Public? 5 IPO Planning Tips for Employees with Stock Comp
    Jul 31 2025
    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.
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    12 mins
  • The One Big Beautiful Bill Breakdown

    The One Big Beautiful Bill Breakdown
    Jul 24 2025
    tax law changes, QSBS, AMT relief, estate tax planning, retirement strategy, QBI deduction, small business owners, financial planning, OBBB, One Big Beautiful Bill
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    8 mins