Episodes

  • The Equity Compensation Blind Spot

    The Equity Compensation Blind Spot
    Aug 11 2026
    RSUs and stock options often make up the single largest slice of a high earner's net worth, and this episode breaks down the tax surprises that come with them. We explain why the standard withholding on vesting shares almost never covers what you'll actually owe, and why ISOs can trigger real tax bills before you've sold a single share. From there we cover why "just holding" concentrated company stock isn't the safe move it feels like, according to both the SEC and FINRA. Finally, we walk through the underused tools, like NUA elections and 10b5-1 plans, that actually manage the risk instead of ignoring it.
    Show More Show Less
    10 mins
  • Estate Planning Isn't for the Elderly

    Estate Planning Isn't for the Elderly
    Aug 4 2026
    Only about a third of Americans have a will, and this episode explains why that's most dangerous for the people who assume they have time: young parents and high earners. We look at why your will doesn't actually control everything, since retirement accounts and life insurance follow whatever beneficiary form you filled out years ago, not your estate documents. A landmark Supreme Court case shows just how rigidly those forms get enforced, even when a divorce decree says otherwise. With trillions in wealth about to change hands and new rules compressing how fast heirs must draw down inherited accounts, this is the ten-minute check most high earners keep putting off.
    Show More Show Less
    10 mins
  • The Raise Trap

    The Raise Trap
    Jul 28 2026
    Nearly half of six-figure earners still live paycheck to paycheck, and this episode explains why. We dig into the "raise trap," the mechanical reason spending rises in lockstep with income, leaving even top earners with nothing saved. Along the way, we look at why windfalls, from NFL contracts to lottery jackpots, rarely change the outcome without a plan. The fix isn't earning less; it's deciding where the next dollar goes before your lifestyle gets a vote.
    Show More Show Less
    10 mins
  • From Income to Wealth: The Transition Most High Earners Never Plan For

    From Income to Wealth: The Transition Most High Earners Never Plan For
    Jul 14 2026
    There's a gap between the top 1% of income earners and the top 1% of wealth holders — and it's wider than most people expect. This episode explores why high earners so frequently fail to convert income into lasting wealth, from lifestyle inflation and a late start to tax drag and the absence of an intentional savings strategy. You'll learn how the wealthiest Americans actually save, what the real retirement number looks like, and the specific decisions that separate people who earn well from those who build something that lasts.
    Show More Show Less
    9 mins
  • The 5 Biggest Financial Mistakes High-Income Professionals Make

    The 5 Biggest Financial Mistakes High-Income Professionals Make
    Jul 7 2026
    Earning a high income doesn't automatically produce financial security — and the data confirms it. This episode identifies the five most common financial mistakes made by doctors, lawyers, and other high-income professionals: overconfidence in financial decision-making, a delayed start due to debt and long training programs, lifestyle inflation that absorbs every raise, exposure to the wrong financial products, and chronically underinsuring the income that funds everything else. These mistakes are common, understandable, and correctable — but only once you can see them clearly.
    Show More Show Less
    11 mins
  • Moving Your Money: Why It Feels Risky and How to Do It the Right Way

    Moving Your Money: Why It Feels Risky and How to Do It the Right Way
    Jun 30 2026
    Changing financial advisors is one of the most common decisions high earners delay — not because the process is complicated, but because it feels that way. This episode demystifies the ACATS transfer system, which moves most account assets in three to four business days, and addresses the psychological barriers — fear of confrontation, loss aversion, inertia — that keep people in professional relationships that no longer serve them. If you've been thinking about making a change, this is the episode that tells you exactly what to expect.
    Show More Show Less
    9 mins
  • Do You Really Know What You're Paying in Fees?

    Do You Really Know What You're Paying in Fees?
    Jun 23 2026
    Most investors can name their advisory fee. Almost none can state their all-in annual cost — and the difference can amount to hundreds of thousands of dollars over a career. This episode breaks down the three layers of investment costs: the advisor's fee, the underlying fund expenses, and platform charges that rarely appear as a line item. You'll learn how to calculate your true total cost, what questions to ask your advisor, and how to evaluate whether what you're paying is commensurate with what you're receiving.
    Show More Show Less
    8 mins
  • Market Volatility: What Sophisticated Investors Do When Markets Get Rough

    Market Volatility: What Sophisticated Investors Do When Markets Get Rough
    Jun 16 2026
    In 2024, the S&P 500 returned over 25% — yet the average investor captured only 16.54% of it. This episode explores the behavioral science behind why markets feel so dangerous when they drop, and what disciplined investors actually do differently. You'll learn why loss aversion is hardwired into your decision-making, why market timing reliably destroys returns even for intelligent people, and how to build a plan that works before volatility hits — so you're not making critical decisions in the middle of a storm.
    Show More Show Less
    10 mins