Executives & Equity-Comp Professionals
RSUs, ISOs, ESPP, and a concentrated position that's done very well, now carrying real risk and tax baggage. Dogpatch Wealth builds tax-aware diversification plans for SF Bay Area executives and tech leaders.
The Concentrated-Stock Problem Most Executives Face
Years of RSUs, ISOs, and ESPP purchases add up, and one day you look at the statement and a single company stock has quietly become most of your net worth. That position did very well, and now it carries real risk and real tax baggage. The challenge is unwinding the concentration without handing a fortune to the IRS in a single year.
RSU, ISO & ESPP Planning
Each form of equity comp has its own playbook. We typically treat RSUs like a cash bonus at vest, selling to control concentration rather than buying more company stock. For ISOs we model the spread, the AMT impact, and your holding period to time exercises deliberately. For ESPP we capture the discount while keeping your overall exposure in check, all coordinated with the rest of your plan.
Concentrated Stock Diversification & Tax Strategy
There is no single button for diversifying a large position, but several levers used together help: direct indexing with ongoing tax-loss harvesting, selling in planned stages across tax years, gifting or charitable strategies, and timing sales around lower-income years. We model the after-tax outcome and build a multi-year plan rather than a one-time dump.
Coordinating Equity Comp With Your Full Financial Plan
Equity comp does not live in a vacuum. We fold your vesting schedule, tax withholding gaps, and concentration risk into the same plan that covers your cash flow, retirement, and family goals, so each vest and each sale is a decision that fits the whole picture rather than a scramble against a deadline.
Pre-IPO & Post-IPO Planning
The window around an IPO is dense with decisions and short on time. Before the event we screen QSBS eligibility, model 10b5-1 plans, and put structures in place while they still work. After the event we manage the transition from paper wealth to a diversified, tax-aware portfolio. Starting early is the single biggest advantage you have.
Frequently Asked Questions
-
There is no single button, but several levers used together help: direct indexing with ongoing tax-loss harvesting, selling in planned stages across tax years, gifting or charitable strategies, and timing sales around lower-income years. We model the after-tax outcome and build a multi-year plan rather than a one-time dump.
-
It depends on the spread, the AMT impact, your holding period, and your view on the stock. We model exercise scenarios against your full tax picture to find the timing that captures favorable long-term treatment without an avoidable AMT surprise. The goal is a deliberate plan, not a deadline-driven scramble.
-
Treat each vest like a cash bonus you would not use to buy more company stock. We typically plan to sell at vest to control concentration, cover the tax withholding gap, and redeploy into a diversified, tax-aware portfolio, all coordinated with your other equity and your goals.
-
It may be. QSBS (Section 1202) generally requires C-corporation stock acquired at original issuance, a company under the gross-asset threshold when issued, and a 5-year hold. We help you screen eligibility early and, where it fits, coordinate trust-stacking strategies before a liquidity event.
-
Yes. We regularly advise executives and employees across San Francisco and Silicon Valley tech, finance, and biotech employers on RSUs, ISOs, ESPP, 10b5-1 plans, and concentrated positions. We tailor the plan to your specific equity package and company situation.
-
Existing limited partners log in at dogpatchfunds.com. Your credentials are issued at onboarding.