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Business Owner
Founder · Silicon Valley
For Startup C-Suite & Founders
MicroTax for the people
building from zero
and stewarding what comes next
CEOs, CFOs, COOs, and VP-level leaders at Series-A-through-pre-IPO companies. Where the equity is mostly illiquid, the founder shares carry the future, and the planning window opens once and closes when the deal closes.
A pre-IPO founder with properly qualified §1202 shares can take up to $10M of capital gains free of federal tax. A founder with the same shares, mis-handled before the liquidity event, takes the full federal hit. The difference is paperwork done five years before the exit.
The planning that determines after-tax outcomes for startup leaders happens long before the term sheet is signed. QSBS qualification, §83(b) timing, ISO/AMT modelling, trust placement, charitable structuring, all of these compress into the months before a liquidity event, or they don't get done at all. MicroTax exists to do them on time, before the structuring window shuts.
Section 01 · Audience
Who this serves
Founders, CEOs, CFOs, COOs, and VP-level leaders at venture-backed companies, Series A through pre-IPO. Compensation is typically modest in cash and significant in equity, with the equity itself representing the entire wealth thesis. Income ranges $200K–$600K in cash; equity, on paper, can be ten times that or more.
The defining feature is not the title or the cash. It is the calendar. Most of the planning that determines after-tax outcomes for this segment happens in a finite window, five years before the exit for QSBS, six months before a tender for charitable structuring, the moment before an option grant for §83(b) timing, and then doesn't get done at all.
This is the audience for whom when a decision is made matters more than which decision is made. A good move executed late is a bad move. A mediocre move executed early often beats a great move executed at the closing dinner.
Section 02 · Diagnostic
What's typically going wrong
Most of these are not unusual. Each is well-documented, well-understood, and routinely missed, because the work has to happen years before the moment when its absence becomes obvious.
Six recurring problems in this segment
QSBS §1202 qualification not preserved.
Five-year hold from original issuance in a qualifying business with gross assets under $50M at issuance. The technical rules are unforgiving. A single secondary sale, conversion, or restructure done without care can disqualify what would have been up to $10M of federally tax-free gain per shareholder per qualifying issuer.
§83(b) elections missed or filed late.
Restricted stock with a substantial risk of forfeiture is taxed at vest unless an §83(b) is filed within 30 days of grant. Missing the window means paying ordinary income tax on the appreciation that occurs over the entire vesting period. The election has to be filed early or it can't be filed at all.
ISO/AMT exposure on private-company exercise.
Exercising ISOs triggers AMT on the spread between strike price and fair-market-value, even though no cash has changed hands. Founders and early employees have, repeatedly, ended up with AMT bills exceeding their cash savings. The fix is to model AMT before exercise, not after.
Founder share basis not documented.
Original issuance basis, secondary sale tracking, and qualifying-business attestations need to be documented at the time, not reconstructed in the year of the exit. Reconstructed documentation rarely passes scrutiny.
No pre-event trust or gifting structure.
Grantor trusts, intentionally defective grantor trusts, and charitable remainder trusts placed before a liquidity event compound across the event itself. Placed after, they accomplish less than half of what they could have. The structuring window is the months before the term sheet, not the months after.
Pre-exit charitable strategies unconsidered.
Donor-advised funds funded with appreciated pre-IPO stock generate a charitable deduction at fair-market-value and remove the appreciation from the taxable estate. For founders facing a liquidity event with no charitable plan, this is often the single largest after-tax optimization available, and it requires execution before the lockup expires.
Section 03 · The change
What changes under a MicroTax engagement
Seven specific moves, sequenced through the F.A.S.T. Steps method, with the entire sequence calibrated to the liquidity-event horizon.
1
Equity inventory & cap-table modelling
Founder shares, options, RSUs, secondary sales, and warrants reconciled into a single ownership picture with grant dates, vesting schedules, and tax characteristics documented for every position.
2
§83(b) protection & basis documentation
For every restricted-stock grant, an §83(b) calculation and filing recommendation within the 30-day window. Basis documentation built at the time, not reconstructed later.
3
ISO/AMT planning
Exercise timing modelled against AMT exposure, cash flow, and the holding period required for long-term capital-gains treatment. Partial-disqualification approaches where appropriate.
4
QSBS §1202 qualification & preservation
The single highest-leverage planning move for founders facing a liquidity event. Qualifying-business attestations, holding-period satisfaction, original-issuance documentation, and stacking-strategy modelling across multiple shareholders. See the related §7702 layer →
5
Pre-event trust & gifting structure
Grantor trusts, intentionally defective grantor trusts, and charitable remainder structures placed before the liquidity event so growth compounds outside the taxable estate. Coordinated with partner attorneys.
6
Pre-exit charitable design
Donor-advised funds, charitable remainder trusts, and direct gifting of appreciated pre-IPO stock structured for maximum deduction at fair-market-value, funded before the lockup expires.
7
Post-event diversification & protection
Once the deal closes: tax-aware diversification, §7702 TFRA layer, estate-document refresh, asset-protection structures, and the transition from one large concentrated position into a coordinated long-term plan.
Section 04 · Outcomes
Indicative year-one outcomes
$10M
QSBS §1202 exemption preserved per qualifying shareholder
2–5 yrs
Typical planning window before liquidity event closes optionality
$1.5M+
Avg. liquidity-event tax recovered for properly-structured founders
Illustrative, based on representative founder outcomes; individual results vary materially with company structure, exit type, and timing. QSBS outcomes depend on holding-period satisfaction and qualifying-business status under §1202.
Section 05 · A client voice
From a founder who'd already signed
Section 06 · Go deeper
Related strategies for startup leaders
Service · Flagship
§7702 Tax-Free Retirement, properly explained
After the liquidity event, the question shifts from "how much tax do I owe?" to "how do I structure what's left?" The §7702 vehicle is built for high-net-worth founders looking for retirement income outside the qualified-plan ceiling. Read the explainer →
Methodology
The F.A.S.T. Steps Method
Our four-stage advisory framework, Foundational, Advanced, Strategic, Tactical, applied with particular sensitivity to the liquidity-event timeline. The work that has to happen years in advance, sequenced correctly. See the methodology →
Article · Pre-IPO Playbook
QSBS §1202, the pre-IPO playbook
The five-year hold, the qualifying-business test, the original-issuance rule, the stacking strategy. Up to $10M of capital gains free of federal tax, or zero, depending on what you did three years ago. Read the article →