Taxes, Concentration, and the Planning Problem Nobody Connects for You Week 6 | The Missing Chapter | Joshua Grass, CFA, CFP® Your employer gave you RSUs. Did anyone explain what they actually do to your taxes, your portfolio, and your financial plan? For most people, the answer is somewhere between “not really” and “not at all.” The grant shows up in an offer letter. Shares vest on schedule and land in a brokerage account. And the full picture tends to go unexplained: what that income means for your tax bill, how it fits into your investments, and what the sell-or-hold decision actually involves. Restricted stock units have become one of the most common forms of compensation for high earners at public companies. Most people know what they are, roughly. What’s less well understood is how they function as a connected planning problem, one that touches your tax bracket, your […]
Week 5 (Special Edition) | The Missing Chapter | Joshua Grass, CFA, CFP® I was recently invited to speak to a group of young engineers, most of them a year or two into their first real jobs. They had come prepared with a written list of questions. Near the top: How do we find a good financial advisor? Before I answered, I thought about what was really behind the question. Reading between the lines, from the questions they were asking and what they weren’t quite saying, a few things were clear: some felt like they were probably leaving money on the table, some were starting to earn real money and had no plan for it, and more than a few had heard stories about advisors taking advantage of clients and weren’t sure who to trust. That last part is worth pausing on, because it’s the right instinct. The financial advisory […]
Week 4 – The Missing Chapter – Joshua Grass, CFA, CFP® Our son Beaux was born on December 4th, three weeks ahead of schedule. A few weeks later, the medical bills arrived. We paid them and didn’t touch the HSA. I want to be honest about what made that an easy call for us. We’re in a financial position where we can afford to contribute to an HSA consistently. We have good insurance that covered the significant majority of the delivery costs. And even if we’d been on the hook for our full annual out-of-pocket maximum, we could have covered that from our regular cash flow without real strain. That’s not a universal position, and I don’t want to gloss over it. For a lot of people, the HSA functions as exactly what it sounds like: a savings buffer for healthcare costs that insurance doesn’t cover. A way to […]
Week 3 | The Missing Chapter | April 2026 A couple I recently started working with are a few months from retirement. Decades of consistent saving, a paid-off house, no debt, a retirement income they can live on comfortably. By the numbers, they are in good shape. They had also been putting off home updates for a while, the way most people do during the busy years. Now, with retirement a few months out, the project had become both timely and necessary. Getting up and down the stairs had gotten harder as they had gotten older. The renovation would make the house safer and easier to move through. They wanted to stay in that house as long as they could, and doing it now, while they had the energy to manage a construction project, made more sense than waiting. When we started working together and looked at how to fund […]