Page 81: Stock options letters. ISO, NSO, RSU, 83(b) elections. I have been putting this one off because equity compensation is genuinely complex and I wanted to do it properly rather than write four shallow templates with placeholder language. The ISO letter required building an AMT capacity framework that an advisor can actually use: here is how many ISOs you can exercise before triggering AMT, here is what happens to the AMT credit if you go over, here is why the year-end exercise window exists. The 83(b) election letter was the one I was most careful about. The 30-day filing deadline is absolute — no extensions, no relief, courts have uniformly refused — and advisors who serve pre-IPO company employees need to communicate this deadline with urgency. I put it in bold, with the specific deadline date, in the first paragraph. The RSU letter had an interesting compliance wrinkle: advisors working with clients who hold concentrated positions in their employer's stock need to document the concentration level and their recommendation explicitly. If the stock subsequently drops 60%, the advisor who sent a letter noting "this represents 34% of your investable assets, I recommend a diversification schedule" is in a very different position than the one who didn't mention it.

Page 82: Deferred compensation letters. NQDC plans are, in my experience, the area where the most money is left on the table through benign neglect. The mechanics are not complicated once you understand them — defer now, pay tax later, hopefully at a lower rate — but the election windows are annual, the deadlines are real, and the 409A rules that govern distribution elections are genuinely restrictive in ways that catch clients off-guard. I wrote four letters: the deferral election strategy letter (the Q4 letter that should go to every executive client), the distribution election planning letter (the one that helps clients not regret their choices in year 15), the 409A overview for new participants (the one that explains why you can't just "change your mind" about the distribution timing), and the SERP update letter (for the increasingly common situation where an employer's SERP has been amended or the company's financial position has changed and the unsecured nature of the obligation deserves a conversation). The California tax note in the deferred comp letter is something I specifically wanted to include — advisors serving California executives who plan to retire elsewhere often forget that California taxes NQDC on compensation earned in-state, regardless of where the distribution is received. It's a common and expensive blind spot.

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