Who We Serve
Venture & Technology Family Tax AdvisoryPractice Areas
Trusts & Estates Business TaxEA Academy
EA Exam Program Student AreaVenture & Technology · Founders · Executives · Investors
37.8199° N · 122.4783° W — Golden Gate · San Francisco Bay Area
Advance tax advice for Silicon Valley founders, executives and investors on equity compensation, company structure, financings, M&A and due diligence — coordinated with counsel and investment advisers.
By email inquiry first · 30 minutes · credited in full upon engagement
Email is for initial communication only. Sensitive documents are not sent by ordinary email; the channel is arranged separately, with an NDA where appropriate.
Our View
The tax on an eight-figure exit is set largely by earlier decisions: when shares were issued, who holds them, where income is sourced, how the company handles R&D and assets, and how the deal is structured. Our work is to complete that analysis before those decisions are made.
Practice Areas
Six areas, from the founder's equity to the deal and what follows.
01How We Work
Five questions, taken in order; each answer determines whether the next is necessary.
What is actually in place?
Facts to establishIndividual: share classes and lots, dates and basis, work and residence. Company: entity, IP, R&D locations. Deal: LOI terms and timetable.
DeliverableFact and position schedule
After-tax result on each path?
Facts to establishHold, secondary, tender, M&A, IPO — federal, California, AMT and NIIT modeled separately.
DeliverableMulti-scenario after-tax model
Which arrangements remain available?
Facts to establish§1202 exclusions, deal structure, R&D and asset choices, gifts and charitable vehicles, residency — each with cost and risk.
DeliverablePlan or structuring memorandum
Who implements, when, in which documents?
Facts to establishLegal documents drafted by counsel; appraisal timing; company-level qualification; post-closing coordination.
DeliverableExecution checklist
Does it still hold as things change?
Facts to establishAnnual review on current parameters; immediate involvement on new rounds, offers or IPO windows.
DeliverableAnnual review memorandum
02Key Considerations
QSBS
Stock acquired after July 4, 2025 is excluded in 3-, 4- and 5-year tiers, so old and new shares in one company follow different rules and must be tracked by lot; California does not conform. Treasury officials said in May 2026 that multi-trust stacking will be addressed.
ISO & AMT
The ISO spread is an AMT item; from 2026 the phase-out rate is 50%, so exercises are sized against current income, estimates and liquidity.
California
Option income is allocated by California workdays from grant to exercise, and RSU income from grant to vest, and moves near a transaction draw audits; since 2023 California treats ING trusts as grantor trusts.
Deal Structure
Stock and asset deals produce very different seller tax; 338(h)(10), F reorganizations and rollovers each have prerequisites; a tax-deferred rollover can carry the QSBS holding period only if reorganization requirements are met, and the exclusion is limited to gain built in at the exchange.
R&D & Compute
Domestic R&D is deductible currently from 2025, foreign R&D is amortized over 15 years; qualifying GPUs and hardware get 100% first-year expensing; California conforms to neither in full and is modeled separately.
Concentration
10b5-1 plans, exchange funds, hedges and loans, CRTs and donor-advised funds are taxed differently, and certain hedges may be constructive sales under §1259; charitable transfers must precede a practically certain sale. Investment decisions rest with the client and adviser.
03Illustrative Analysis
An AI-company founder received shares at formation in August 2025 (83(b) election made) at near-zero basis; the company qualified as a small business at issuance. Expected gain on sale: $20,000,000. The founder is a California resident.
| Year 3 | Year 4 | Year 5 | |
|---|---|---|---|
| Federal exclusion | 50% | 75% | 100% |
| Federal gain excluded ($15M cap) | $7,500,000 | $11,250,000 | $15,000,000 |
| Federal tax | $3,575,000 | $2,382,500 | $1,190,000 |
| California tax (no QSBS) | $2,660,000 | $2,660,000 | $2,660,000 |
| After-tax proceeds | $13,765,000 | $14,957,500 | $16,150,000 |
Reading the Analysis
Selling in year 3 leaves about $2,385,000 less than selling in year 5; a year-3 offer would need to reach about $23,800,000 (roughly 19% higher) to match a $20,000,000 sale in year 5 after tax. Whether to wait depends on whether an offer clears that threshold and on valuation and deal risk in the meantime — a judgment for the client; the analysis supplies the after-tax threshold.
Illustrative only; not a specific client, not investment advice and no outcome is promised. Federal: the non-excluded part within the cap at 28% plus 3.8% NIIT, gain above the cap at 20% plus 3.8%; California simplified at the 13.3% top rate. Excludes AMT, transaction costs, the state tax deduction, time value of money and deal risk.
04Perspective
Planning is tested years later — in an audit, a diligence process or a family event. Every document is prepared to that standard.
Earned while at securities and investment firms; valuation basis, liquidity and concentration are assessed before tax treatment.
A U.S. CPA license: opinions are signed, and models are reviewable and traceable.
Authorized to represent taxpayers in audits, collections and appeals; planning positions are prepared to be defended.
Pursued after a first-hand U.S. legal proceeding; clause-level work with counsel so tax intent is written into the documents.
The firm sells no insurance or investment products and charges no asset-based fees.
05Engagement
The first session is not booked cold: submit your topics, and we confirm fit before you book. If the answer is 'nothing to do now', we say so in writing.
01
$699
Submit the topic form first; 30 minutes with Wen Shi, followed by a one-page memorandum of risks, open windows and next steps.
Credited in full upon engagement
Email us firstAlready in touch? Book · $69902
Scoped quote
Liquidity planning, company structure, deal structure, due diligence, investor tax, post-exit planning — scope and fee agreed in writing. Diligence can be quoted directly.
Scope and fee agreed in writing
03
Annual retainer
Individuals and families: planning, returns, major-event involvement, IRS representation. Companies: tax and finance advisory, financing and diligence readiness.
For clients with recurring equity and transaction events
Initial Consultation
Submit the topic form on the contact page, or email a brief description.
Sensitive documents are not sent by ordinary email; the channel is arranged separately, with an NDA where appropriate.
Once fit is confirmed, book and pay $699.
A 30-minute session by video or phone, followed by a one-page memorandum.
06Suitability
Where a consultation shows the matter is outside our scope, we say so and refund the fee.
The LOI, the gift, the move and the exercise each carry a deadline. The initial consultation identifies them and determines which remain open.
Email is for initial communication only. Sensitive documents are not sent by ordinary email; the channel is arranged separately, with an NDA where appropriate.
General tax information only; not tax, legal or investment advice for any specific situation. Rules and amounts may change and apply only on specific facts. Wen Shi is a Certified Public Accountant, an Enrolled Agent and a CFA® charterholder, and a J.D. candidate who does not provide legal advice. The firm gives no investment advice and sells no insurance or investment products. The firm gives no investment advice and makes no securities recommendations, provides no deal sourcing and takes no success fees; legal documents are drafted by the client's counsel.
Venture & Technology · Founders · Executives · Investors
Advance tax advice for Silicon Valley founders, executives and investors on equity compensation, company structure, financings, M&A and due diligence — coordinated with counsel and investment advisers.
By email inquiry first · 30 minutes · credited in full upon engagement Email is for initial communication only. Sensitive documents are not sent by ordinary email; the channel is arranged separately, with an NDA where appropriate.
Our View
The tax on an eight-figure exit is set largely by earlier decisions: when shares were issued, who holds them, where income is sourced, how the company handles R&D and assets, and how the deal is structured. Our work is to complete that analysis before those decisions are made.
Five points that set the outcome
Practice Areas
Six areas, from the founder's equity to the deal and what follows.
How We Work
Five questions, taken in order; each answer determines whether the next is necessary.
Facts to establishIndividual: share classes and lots, dates and basis, work and residence. Company: entity, IP, R&D locations. Deal: LOI terms and timetable.
DeliverableFact and position schedule
Facts to establishHold, secondary, tender, M&A, IPO — federal, California, AMT and NIIT modeled separately.
DeliverableMulti-scenario after-tax model
Facts to establish§1202 exclusions, deal structure, R&D and asset choices, gifts and charitable vehicles, residency — each with cost and risk.
DeliverablePlan or structuring memorandum
Facts to establishLegal documents drafted by counsel; appraisal timing; company-level qualification; post-closing coordination.
DeliverableExecution checklist
Facts to establishAnnual review on current parameters; immediate involvement on new rounds, offers or IPO windows.
DeliverableAnnual review memorandum
Key Considerations
QSBS
Stock acquired after July 4, 2025 is excluded in 3-, 4- and 5-year tiers, so old and new shares in one company follow different rules and must be tracked by lot; California does not conform. Treasury officials said in May 2026 that multi-trust stacking will be addressed.
ISO & AMT
The ISO spread is an AMT item; from 2026 the phase-out rate is 50%, so exercises are sized against current income, estimates and liquidity.
California
Option income is allocated by California workdays from grant to exercise, and RSU income from grant to vest, and moves near a transaction draw audits; since 2023 California treats ING trusts as grantor trusts.
Deal Structure
Stock and asset deals produce very different seller tax; 338(h)(10), F reorganizations and rollovers each have prerequisites; a tax-deferred rollover can carry the QSBS holding period only if reorganization requirements are met, and the exclusion is limited to gain built in at the exchange.
R&D & Compute
Domestic R&D is deductible currently from 2025, foreign R&D is amortized over 15 years; qualifying GPUs and hardware get 100% first-year expensing; California conforms to neither in full and is modeled separately.
Concentration
10b5-1 plans, exchange funds, hedges and loans, CRTs and donor-advised funds are taxed differently, and certain hedges may be constructive sales under §1259; charitable transfers must precede a practically certain sale. Investment decisions rest with the client and adviser.
Illustrative Analysis
An AI-company founder received shares at formation in August 2025 (83(b) election made) at near-zero basis; the company qualified as a small business at issuance. Expected gain on sale: $20,000,000. The founder is a California resident.
Federal exclusion
50%75%100%Federal gain excluded ($15M cap)
$7,500,000$11,250,000$15,000,000Federal tax
$3,575,000$2,382,500$1,190,000California tax (no QSBS)
$2,660,000$2,660,000$2,660,000After-tax proceeds
$13,765,000$14,957,500$16,150,000Selling in year 3 leaves about $2,385,000 less than selling in year 5; a year-3 offer would need to reach about $23,800,000 (roughly 19% higher) to match a $20,000,000 sale in year 5 after tax. Whether to wait depends on whether an offer clears that threshold and on valuation and deal risk in the meantime — a judgment for the client; the analysis supplies the after-tax threshold.
Illustrative only; not a specific client, not investment advice and no outcome is promised. Federal: the non-excluded part within the cap at 28% plus 3.8% NIIT, gain above the cap at 20% plus 3.8%; California simplified at the 13.3% top rate. Excludes AMT, transaction costs, the state tax deduction, time value of money and deal risk.
Perspective
Planning is tested years later — in an audit, a diligence process or a family event. Every document is prepared to that standard.
Wen Shi · CPA, EA, CFA®
Earned while at securities and investment firms; valuation basis, liquidity and concentration are assessed before tax treatment.
A U.S. CPA license: opinions are signed, and models are reviewable and traceable.
Authorized to represent taxpayers in audits, collections and appeals; planning positions are prepared to be defended.
Pursued after a first-hand U.S. legal proceeding; clause-level work with counsel so tax intent is written into the documents.
The firm sells no insurance or investment products and charges no asset-based fees.
Engagement
First session
$699
Submit the topic form first; 30 minutes with Wen Shi, followed by a one-page memorandum of risks, open windows and next steps.
Credited in full upon engagement
Email us first Already in touch? Book · $699Liquidity planning, company structure, deal structure, due diligence, investor tax, post-exit planning — scope and fee agreed in writing. Diligence can be quoted directly.
Scope and fee agreed in writing
Individuals and families: planning, returns, major-event involvement, IRS representation. Companies: tax and finance advisory, financing and diligence readiness.
For clients with recurring equity and transaction events
Suitability
Where a consultation shows the matter is outside our scope, we say so and refund the fee.
The LOI, the gift, the move and the exercise each carry a deadline. The initial consultation identifies them and determines which remain open.
Email us first Already in touch? Book · $699General tax information only; not tax, legal or investment advice for any specific situation. Rules and amounts may change and apply only on specific facts. Wen Shi is a Certified Public Accountant, an Enrolled Agent and a CFA® charterholder, and a J.D. candidate who does not provide legal advice. The firm gives no investment advice and sells no insurance or investment products. The firm gives no investment advice and makes no securities recommendations, provides no deal sourcing and takes no success fees; legal documents are drafted by the client's counsel.