1 October 2026, 12:58 PM
Tax planning, answered.
The questions executives, founders, and operators ask most often before engaging on private client services.
What are private client services, and how are they different from return preparation?
Return preparation is reactive — it reports what already happened. Our private client services are proactive — we design entity structure, transaction timing, jurisdiction, and equity sequencing before a decision is made, so the eventual return reflects an engineered outcome. Most of our value is created in the 12 to 36 months before a liquidity event, not in the 90 days before a filing deadline.
When should a high-income earner first engage a tax strategist?
Ideally before any of the following: a first priced funding round, an 83(b) election window, a planned secondary, a state move, an inheritance, or a sale or recapitalization. Once equity is issued, a transaction is signed, or domicile is challenged, the structuring window closes quickly. Most of our W-2 executive clients start at $2M+ in annual income; most founder clients start pre-exit.
How does QSBS Section 1202 planning actually work?
QSBS can exempt up to $10M (or 10× basis) of gain from federal tax on the sale of qualified small-business stock held five years. We structure issuance timing, stacking via non-grantor trusts to multiply the per-taxpayer exemption, gifting strategies for spouses and family members, and exit sequencing to maximize the available exclusion. The planning has to happen before issuance — not at exit.
Do you handle equity compensation — RSUs, ISOs, NSOs, founder stock?
Yes — equity compensation planning is one of our most active practice areas. We model AMT exposure on ISO exercises, sequence 10b5-1 plans for post-IPO operators, structure exchange funds for diversification, and coordinate with company counsel on lockups, secondaries, and recapitalizations. The work is done with the operator's CPA, attorney, and wealth manager — not in isolation.
Charitable Donation Strategies
We incorporate Charitable Donation Strategies into broader tax planning where appropriate, including DAFs, CRTs, CLATs, and private foundations, with the goal of coordinating charitable objectives with income, deductions, and long-term wealth planning.
Conatct us : https://neiljesani.com/tax/
The questions executives, founders, and operators ask most often before engaging on private client services.
What are private client services, and how are they different from return preparation?
Return preparation is reactive — it reports what already happened. Our private client services are proactive — we design entity structure, transaction timing, jurisdiction, and equity sequencing before a decision is made, so the eventual return reflects an engineered outcome. Most of our value is created in the 12 to 36 months before a liquidity event, not in the 90 days before a filing deadline.
When should a high-income earner first engage a tax strategist?
Ideally before any of the following: a first priced funding round, an 83(b) election window, a planned secondary, a state move, an inheritance, or a sale or recapitalization. Once equity is issued, a transaction is signed, or domicile is challenged, the structuring window closes quickly. Most of our W-2 executive clients start at $2M+ in annual income; most founder clients start pre-exit.
How does QSBS Section 1202 planning actually work?
QSBS can exempt up to $10M (or 10× basis) of gain from federal tax on the sale of qualified small-business stock held five years. We structure issuance timing, stacking via non-grantor trusts to multiply the per-taxpayer exemption, gifting strategies for spouses and family members, and exit sequencing to maximize the available exclusion. The planning has to happen before issuance — not at exit.
Do you handle equity compensation — RSUs, ISOs, NSOs, founder stock?
Yes — equity compensation planning is one of our most active practice areas. We model AMT exposure on ISO exercises, sequence 10b5-1 plans for post-IPO operators, structure exchange funds for diversification, and coordinate with company counsel on lockups, secondaries, and recapitalizations. The work is done with the operator's CPA, attorney, and wealth manager — not in isolation.
Charitable Donation Strategies
We incorporate Charitable Donation Strategies into broader tax planning where appropriate, including DAFs, CRTs, CLATs, and private foundations, with the goal of coordinating charitable objectives with income, deductions, and long-term wealth planning.
Conatct us : https://neiljesani.com/tax/