Dispatches

1. Dispatch 15

   The Tax Alpha That Decays

   Direct indexing is sold as ongoing tax alpha. It produces tax alpha for a defined window, after which the sleeve hardens into a position whose harvestable losses thin to near zero. The question is not whether it works. The question is whether the structure that follows the window has been planned.

2. Dispatch 14

   The Lot You Sell First

   The post-IPO lockup is treated as a liquidity event. It is in fact an inventory decision, and the brokerage's default settings — chosen by no one and reviewed by almost no one — pick the worst lots first under both of the frames that should actually be deciding the order.

3. Dispatch 13

   When the Position Becomes the Plan

   A year-end net-worth tally tells you when the position you happen to hold has quietly become the position that defines what you can do next — and what was once a portfolio question has become a planning question.

4. Dispatch 12

   The Lockup You Sign For

   An exchange fund and a direct-indexing account are often presented as alternatives within a single decision. They are structurally different tools, doing different work, with consequences that diverge most sharply at the moments the deck does not cover.

5. Dispatch 11

   The QSBS Question Most Founders Get Wrong

   Section 1202 has changed twice in living memory. Most of what's circulating about it still assumes the older regime, and the founders who rely on that commentary tend not to discover the gap until a return is being filed.

6. Dispatch 10

   What Changed in July

   Two bodies of law, one signing date, and a great deal of planning built on assumptions that no longer hold.

7. Dispatch 09

   The Year With No W-2

   The year after a business sale has a peculiar tax quality. Ordinary income collapses, brackets that have been theoretical for a decade become accessible, and two adjacent systems — Medicare's income-linked premiums and the ACA subsidy cliff — begin reading MAGI with consequences two calendar pages away.

8. Dispatch 08

   The Step-Up That Isn't Yours Yet

   The cost basis reset happens at the date of death. The operational one takes three to six months — and the gap is where the avoidable mistakes get made.

9. Dispatch 07

   What a Signed LOI Actually Starts

   The useful tax runway for a business sale runs backward from the closing date, not forward from the LOI. A timeline-shaped guide to what each window still permits, and what quietly stops being available.

10. Dispatch 06

    The 22% Problem

    Why the default withholding on restricted stock rarely matches the rate it will be taxed at — and how the gap compounds into a January surprise.

11. Dispatch 05

    When Rebalancing Becomes a Tax Event You Didn't Choose

    The irony of disciplined investing in a taxable account.

12. Dispatch 04

    The Free Lunch Sitting in Your Losers

    Tax-loss harvesting, properly understood, is not about losing. It is about keeping the option.

13. Dispatch 03

    The Quiet Cost of Mutual Fund Turnover

    What the expense ratio doesn't tell you, and why most investors never find out.

14. Dispatch 02

    Two Investors, One Fund, Two Different Tax Bills

    Why where you hold what you own matters as much as what you own.

15. Dispatch 01

    Why Your 1099 Keeps Surprising You

    The tax that runs through your portfolio without ever asking permission.