The Situation

Steven and Grace looked like the picture of Silicon Valley success. Combined cash compensation was extraordinary — roughly $1 million on one side (with about half delivered as RSUs and ISOs still in play) and about $700,000 on the other (with roughly a third in RSUs). They were in the highest federal tax bracket, saving aggressively, and still felt like they were flying blind.

Grace had roughly $1 million in RSU carrying substantial long-term capital gains. So she was reluctant to sell. Steven’s startup stake was illiquid and hard to value, it’s around $2 million based on the current valuation. He also has a decent amount of ISOs.

For years they prepared their own tax returns. That worked until it didn’t. With AMT exposure on ISO exercises, ordinary income on RSU vesting, state taxes, and endless “what if we exercise this year vs. next?”, they couldn’t reliably answer the question that mattered most: What will we actually owe if we do X? Should Steven exercise ISOs now or wait? Sell RSUs at vest or hold? Harvest losses elsewhere to offset gains? Could they qualify for QSBS treatment on startup shares? Would married filing separately ever make sense? Where should new money go? They were smart people drowning in moving parts, not lazy ones avoiding planning.

They wanted minimum tax and wealth preservation, not hot tips or product pitches.

The Approach

Steven and Grace looked for advisors who had guided tech professionals through equity compensation before — not generic “high net worth” talk, but planning that started with vesting calendars, tax projections, and concentration risk.

Just as importantly, they wanted to understand every major decision: exercise timing, sale strategy, diversification, trusts, and investments — no jargon, no black box. They wanted confidence that recommendations were tied to their tax return and their family’s immigration and estate picture, not a commission on the next product.

The work centered on two pillars: equity compensation tax planning and concentration risk management — with cash flow, investments, and protection built around those decisions.

The Results

Steven and Grace were relieved to partner with a team that could do more than rebalance a brokerage account. They received a comprehensive plan that incorporated:

• A personalized net worth map — cash, taxable accounts, retirement accounts, real estate, 529 plans for the daughter and son, and a clear breakdown of RSU, ISO, and private startup holdings (with ranges where values were uncertain), so every recommendation started from one picture of liquid vs. illiquid wealth.

• Cash flow projections — take-home pay after withholding, vesting-driven income spikes, estimated tax payments, and lifestyle spending — so they could see surplus cash before deciding how much to invest or diversify each year.

• Comprehensive tax planning, including:

  • Multi-year tax projections for RSU vesting, ISO exercises (regular tax vs. AMT), and stock sales before they pulled triggers.

  • Exercise-and-sell playbooks — when to exercise ISOs, when to sell vs. hold RSUs, and how to coordinate with other income and deductions.

  • QSBS eligibility review for startup shares — whether requirements might be met and what documentation and holding periods mattered.

• Concentration risk management — a disciplined diversification framework for employer and startup stock, including:

  • Rules for how much single-company exposure to keep vs. trim over time.

  • The guiding question they’d been missing: Concentration via labor capital helped you build wealth; now that financial capital is large, do you want it taking the same bet? If this were cash, what would you buy?

• Life insurance review, including if the coverage through work is sufficient to take care of two minor children and evaluation of a LIRP (life insurance retirement plan) strategy could support tax-favored access to cash value later.

• Safe harbor estimated-tax strategy — modeled federal liability against prior-year safe harbor thresholds so they could avoid underpayment penalties while keeping more cash in high-yield savings until tax payments were due — earning more interest on surplus cash without guessing whether it was “safe” to wait.

Steven and Grace now know what they owe (or would owe) before they exercise or sell, how much employer stock they’re willing to keep, and where new money should go once vesting events create cash. Steven’s ISO decisions are tied to AMT and long-term goals, not gut feel in December.

Most importantly, they have the peace of mind they were looking for: tax outcomes they can see in advance, concentration they’re choosing rather than inheriting from every paycheck, and a team always in their corner.