QSBS Financial Advisor for Venture-Backed Founders
As your QSBS financial advisor, Keystone confirms your Section 1202 eligibility, models every path to a larger exclusion, and helps you execute the structures in time.
Keystone Global Partners is an SEC-registered fiduciary and multi-family office that works with venture-backed founders expecting to personally net $20M or more at exit. Co-Founder Peyton Carr is a recognized authority on Section 1202, having authored widely published analysis and established the firm’s specialized practice around qualified small business stock optimization.
QSBS financial advisory at Keystone is not a one-off consultation. It is the tax engine inside our Personal Exit Advisory® program, where we act as your personal CFO from zero to three years before your liquidity event. We model your equity, quantify what each strategy is worth to you in after-tax dollars, coordinate the attorneys and CPAs who document it, and stay with you through closing and beyond.
Founders who apply the QSBS exclusion at exit, without planning for it in advance, typically leave seven figures on the table, usually because they never multiplied the exclusion across trusts, never addressed state tax, or started planning too late.
KEYSTONE RECOGNITION
What We Actually Do Before Your Exit
Every founder engagement runs through the same six workstreams. QSBS sits at the center, but the value comes from running them all together, in the right order, with enough lead time.
01
Eligibility Verification and Documentation
Before any strategy matters, your stock has to qualify. We review your cap table, acquisition dates, the company’s gross assets at each issuance, its active business history, and any redemptions that could disqualify shares. We then assemble the documentation file the IRS requires, because if your exclusion is challenged, the burden of proof is on you, not the company.
02
Tranche-by-Tranche Exclusion Mapping
Founders rarely hold a single block of stock. Founder shares, options, stock received in a conversion, and secondary purchases each carry their own acquisition dates, holding periods, and sometimes exclusion caps. We map every tranche to its applicable rules, including the pre- and post-OBBBA regimes, so you know exactly how much is excludable today, how much becomes excludable with time, and what is not excludable at all.
03
Interactive Modeling of Your Exit Scenarios
This is where most of our pre-exit time goes. Using our modeling tools, we show you your after-tax proceeds across exit valuations, exit dates, deal structures (cash, stock, earnout), and planning strategies, side by side. You see what a 12-month delay is worth, what a trust structure is worth, what a residency change is worth, and whether a secondary sale today compromises a larger exclusion later.
04
Exclusion Multiplication Through Trusts and Gifting
The per-taxpayer cap is a floor, not a ceiling. By gifting shares to non-grantor trusts and, where appropriate, to family members, each recipient is a separate taxpayer that may qualify for its own exclusion. We design the trust structures with your estate plan in mind, since the same transfers that multiply QSBS also move future appreciation out of your taxable estate. We coordinate with high-quality trust and estate counsel who, like us, understand the importance of planning ahead for an exit.
05
State Tax Strategy
Many states, such as California, do not recognize the federal QSBS exclusion. A California founder with a fully excluded $15M federal gain, for example, still owes roughly $2.0M in state tax. We model your full state exposure and evaluate the paths available to reduce it, including non-grantor trusts, a residency change, and other planning suited to your situation. Then we tell you which option is realistic for your timeline and family, and what each one costs you in trade-offs.
06
Exit Timing and Section 1045 Rollovers
For stock issued after July 4, 2025, the exclusion steps up from 50% at three years to 75% at four and 100% at five. On a $15M position, the difference between a three-year and five-year hold is about $2.4M in federal tax. We model whether a delay is worth pursuing relative to your deal terms and your risk. When gains exceed your cap, or a tranche does not yet qualify, we model Section 1045 rollovers into replacement QSBS so you can defer tax on the excess rather than pay it at closing.
BEYOND THE TAX PLAN
QSBS planning that stops at the tax return leaves money on the table elsewhere in the deal. As part of Personal Exit Advisory®, we also:
Why Founders Choose Keystone
Financial advisors generally treat QSBS as one item on a checklist. For a founder, it is often the largest single tax decision of a lifetime — and it is the center of our QSBS practice.
| Capability | Keystone Global Partners | Generalist Advisor | Large Institution |
|---|---|---|---|
| Founder-first practice, built around exits | — | — | |
| Pre-exit engagement, 0 to 3 years out | Limited | Rarely | |
| Interactive after-tax exit modeling | Rarely | Limited | |
| QSBS stacking and trust multiplication | Rarely | Limited | |
| State residency and non-grantor trust planning | Limited | Varies | |
| Secondary, lending, and deal-term guidance | — | Limited | |
| Fiduciary, SEC-registered, fee-only | Varies | Varies |
Keystone has been recognized by the PAM Awards as Best Private Wealth Manager Under $5 Billion and Best Multi-Family Office Under $25 Billion from 2022 through 2025, and was a ThinkAdvisor Luminaries finalist for financial and investment innovation.
Our Process
Step 1
Equity Audit and Eligibility Review
We review your cap table, grant history, and company records to confirm eligibility and calculate your current maximum exclusion under federal law and the law of your state.
Step 2
After-Tax Exit Modeling
We model your proceeds across valuations, exit dates, holding periods, and planning strategies, and show you which levers are worth the most in your specific situation.
Step 3
Structure Design and Execution
We design the trust, gifting, and residency plan, select the counsel, and sequence every step. We recommend completing this work before an LOI. Transfers made after a deal is in motion carry more risk.
Step 4
Deal Support Through Closing
When an LOI arrives, we run an analysis against the actual deal terms, model cash, stock, and earnout scenarios, and support negotiation of the items that affect you personally.
Step 5
Transition to Full Wealth Management
After closing, we move into a full wealth management relationship: post-exit planning against your original expectations, investment policy, endowment-style asset allocation, alternative investment program, ongoing tax minimization, and family office support where the exit warrants it.
Founder Success Stories
Keystone helped me structure my QSBS across multiple trusts and charitable entities, saving about $12M in federal taxes. Their pre-exit planning was invaluable. We started working together 18 months before my LOI.
The state residency planning alone saved me over $10M. Having Keystone in my corner made the difference between good and exceptional outcomes.
Frequently Asked Questions
When should I engage a QSBS advisor?
Ideally zero to three years before a likely exit, or before your Series B. Trust stacking needs the shares transferred well before any deal is in motion, and a residency change needs to take place well in advance of an exit. If you are within three years of an exit and have not addressed these, now is the right time.
Can my CPA handle QSBS planning?
Most CPAs will confirm eligibility and claim the exclusion on your return. What most do not do is model your exit scenarios, design the trust and gifting structure, address state tax, or advise on secondary sales and deal terms. Those require a specialist engaged early and a team that coordinates your CPA, your attorney, and your deal. That’s where a dedicated QSBS financial advisor comes in.
Do I need to leave California to benefit from QSBS?
Not necessarily. A properly structured non-grantor trust in a no-income-tax state may shield a portion of the gain from California tax without a move. A bona fide residency change remains the most certain way to eliminate California’s 13.3% top rate on the full gain, but it has to be a real move, made well in advance of an exit and sustained afterward. The right answer depends on the size of your exit, your timeline, and whether relocation is realistic for your family.
I am considering a secondary sale before my exit. Does that affect my QSBS?
It can. Which shares you sell, when, and how the transaction is structured all affect your holding period and your remaining exclusion. We model the secondary alongside the full exit so you do not trade a larger exclusion later for liquidity now without knowing the cost.
What does Keystone charge for QSBS financial advisory?
Pre-exit QSBS and exit planning is provided as part of Personal Exit Advisory® at no upfront charge. We recognize that founders rarely have free cash flow before an exit. Our compensation is structured as a tiered, assets-under-management wealth-management arrangement after closing, which keeps us aligned with your after-tax outcome. We discuss fees openly before any engagement begins.
This Is the Right Fit If You Are
- A venture-backed founder with QSBS-eligible equity and a realistic exit within three years, expecting to net $20M or more
- A founder whose position exceeds the per-taxpayer cap and wants to multiply (“stack”) the exclusion before any deal begins
- A repeat founder managing QSBS across multiple companies
- A founder in California or another non-conforming state who needs a concrete state tax plan
- A founder weighing a secondary sale, tender, or share-backed loan and wants to understand the QSBS consequences first
- A founder whose current advisor confirmed eligibility but has not addressed stacking, pacing, state tax, trust structures, or deal terms
This is not the right fit if your personal exit is expected to be under $20M.
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Schedule a Confidential Discussion
Book an introductory call with our founder below.
About Keystone Global Partners
Keystone Global Partners specializes in comprehensive exit planning and wealth management for ultra-high-net-worth venture-backed founders, with a focus on helping founders make informed, well-modeled decisions before liquidity, not after.
Investment advisory services are provided by Keystone Global Partners, LLC, an SEC-registered investment adviser. This page is for educational purposes only and does not constitute legal, tax, or financial advice. QSBS rules are complex and subject to change. Individual outcomes vary. Consult qualified tax and legal professionals regarding your specific situation.
Footnotes
- 1IRC §1202(c)(1), (c)(2), (c)(3), (d), and (e). Redemptions by the issuer from the holder or related persons within the windows in §1202(c)(3) can disqualify otherwise eligible stock.
- 2Pub. L. 119-21 (the One Big Beautiful Bill Act), §70431, amending IRC §1202 for stock acquired after July 4, 2025. Stock acquired on or before that date remains subject to the prior rules, including the $10M or 10x basis cap and the five-year holding requirement.
- 3IRC §1202(b)(1) applies the cap per taxpayer. Non-grantor trusts are separate taxpayers. Gifted shares retain the donor’s holding period and QSBS status under §1202(h)(1) and (h)(2).
- 4IRC §2501 and §2505 (lifetime gift tax exemption). Exemption amounts are indexed and subject to legislative change.
- 5California R&TC §18152.5 (exclusion repealed for tax years beginning on or after January 1, 2013); Pennsylvania and Mississippi do not conform to §1202; Alabama decouples. District of Columbia decoupling per the FY2026 Budget Support Act.
- 6California’s top marginal rate on capital gains is 13.3% (R&TC §17041 plus the 1% Mental Health Services Tax). $15M × 13.3% ≈ $1.995M.
- 7IRC §1202(a)(1)(B) as amended by Pub. L. 119-21, for stock acquired after July 4, 2025: 50% exclusion after three years, 75% after four, 100% after five.
- 8Assumes $15M of gain, 28% §1(h)(4) rate on the non-excluded portion plus 3.8% net investment income tax under §1411. At 50% exclusion, $7.5M taxable × 31.8% ≈ $2.39M; at 100% exclusion, $0.
- 9IRC §1045. Replacement QSBS must be purchased within 60 days of sale and the original stock must have been held more than six months.
- 10IRC §1202(d)(1) as amended by Pub. L. 119-21. The $75M threshold applies to stock issued after July 4, 2025 and is indexed for inflation beginning in 2027.
1. Eligibility Verification and Documentation
Before any strategy matters, your stock has to qualify. We review your cap table, acquisition dates, the company’s gross assets at each issuance, its active business history, and any redemptions that could disqualify shares. We then assemble the documentation file the IRS expects to see, because if your exclusion is challenged, the burden of proof is on you, not the company.
2. Tranche-by-Tranche Exclusion Mapping
Founders rarely hold a single block of stock. Founder shares, options, stock received in a conversion, and secondary purchases each carry their own acquisition date, holding period, and exclusion cap. We map every tranche to its applicable rules, including the pre- and post-OBBBA regimes, so you know exactly how much is excludable today, how much becomes excludable with time, and what is not excludable at all.
3. Interactive Modeling of Your Exit Scenarios
This is where most of our pre-exit time goes. Using our modeling tools, we show you your after-tax proceeds across exit valuations, exit dates, deal structures (cash, stock, earnout), and planning strategies, side by side. You see what a 12-month delay is worth, what a trust structure is worth, what a residency change is worth, and whether a secondary sale today compromises a larger exclusion later.
4. Exclusion Multiplication Through Trusts and Gifting
The per-taxpayer cap is a floor, not a ceiling. By gifting shares to non-grantor trusts and, where appropriate, to family members, each recipient is a separate taxpayer that may qualify for its own exclusion. We design the trust structures with your estate plan in mind, since the same transfers that multiply QSBS also move future appreciation out of your taxable estate. We coordinate with high-quality trust and estate counsel who, like us, understand the importance of planning ahead for an exit.
5. State Tax Strategy
Many states, such as California, do not recognize the federal QSBS exclusion. A California founder with a fully excluded $15M federal gain, for example, still owes roughly $2.0M in state tax. We model your full state exposure and evaluate the paths available to reduce it, including non-grantor trusts, a residency change, and other planning suited to your situation. Then we tell you which option is realistic for your timeline and family, and what each one costs you in trade-offs.
6. Exit Timing and Section 1045 Rollovers
For stock issued after July 4, 2025, the exclusion steps up from 50% at three years to 75% at four and 100% at five. On a $15M position, the difference between a three-year and five-year hold is about $2.4M in federal tax. We model whether a delay is worth pursuing relative to your deal terms and your risk. When gains exceed your cap, or a tranche does not yet qualify, we model Section 1045 rollovers into replacement QSBS so you can defer tax on the excess rather than pay it at closing.
Why Founders Choose Keystone
Financial advisors generally treat QSBS as one item on a checklist. For a founder, it is often the largest single tax decision of a lifetime — and it is the center of our practice.
| Capability | Keystone Global Partners | Generalist Advisor | Large Institution |
|---|---|---|---|
| Founder-first practice, built around exits | — | — | |
| Pre-exit engagement, 0 to 3 years out | Limited | Rarely | |
| Interactive after-tax exit modeling | Rarely | Limited | |
| QSBS stacking and trust multiplication | Rarely | Limited | |
| State residency and non-grantor trust planning | Limited | Varies | |
| Secondary, lending, and deal-term guidance | — | Limited | |
| Fiduciary, SEC-registered, fee-only | Varies | Varies |
Keystone has been recognized by the PAM Awards as Best Private Wealth Manager Under $5 Billion and Best Multi-Family Office Under $25 Billion from 2022 through 2025, and was a ThinkAdvisor Luminaries finalist for financial and investment innovation.
Our Process
Step 1: Equity Audit and Eligibility Review
We review your cap table, grant history, and company records to confirm eligibility and calculate your current maximum exclusion under federal law and the law of your state.
Step 2: After-Tax Exit Modeling
We model your proceeds across valuations, exit dates, holding periods, and planning strategies, and show you which levers are worth the most in your specific situation.
Step 3: Structure Design and Execution
We design the trust, gifting, and residency plan, select the counsel, and sequence every step. We recommend completing this work before an LOI. Transfers made after a deal is in motion carry more risk.
Step 4: Deal Support Through Closing
When an LOI arrives, we run a final tranche analysis against the actual deal terms, model cash, stock, and earnout scenarios, and support negotiation of the items that affect you personally.
Step 5: Transition to Full Wealth Management
After closing, we move into a full wealth management relationship: post-exit planning against your original expectations, investment policy, endowment-style asset allocation, alternative investment program, ongoing tax minimization, and family office support where the exit warrants it.
Founder Success Stories
Keystone helped me structure my QSBS across multiple trusts and charitable entities, saving about $12M in federal taxes. Their pre-exit planning was invaluable. We started working together 18 months before my LOI.
The state residency planning alone saved me over $10M. Having Keystone in my corner made the difference between good and exceptional outcomes.
Frequently Asked Questions
When should I engage a QSBS advisor?
Ideally zero to three years before a likely exit, or before your Series B. Trust stacking needs the shares transferred well before any deal is in motion, and a residency change needs to take place well in advance of an exit. If you are within three years of an exit and have not addressed these, now is the right time.
Can my CPA handle QSBS planning?
Most CPAs will confirm eligibility and claim the exclusion on your return. What most do not do is model your exit scenarios, design the trust and gifting structure, address state tax, or advise on secondary sales and deal terms. Those require a specialist engaged early and a team that coordinates your CPA, your attorney, and your deal. That’s where a dedicated QSBS financial advisor comes in.
Do I need to leave California to benefit from QSBS?
Not necessarily. A properly structured non-grantor trust in a no-income-tax state may shield a portion of the gain from California tax without a move. A bona fide residency change remains the most certain way to eliminate California’s 13.3% top rate on the full gain, but it has to be a real move, made well in advance of an exit and sustained afterward. The right answer depends on the size of your exit, your timeline, and whether relocation is realistic for your family.
I am considering a secondary sale before my exit. Does that affect my QSBS?
It can. Which shares you sell, when, and how the transaction is structured all affect your holding period and your remaining exclusion. We model the secondary alongside the full exit so you do not trade a larger exclusion later for liquidity now without knowing the cost.
What does Keystone charge for QSBS financial advisory?
Pre-exit QSBS and exit planning is provided as part of Personal Exit Advisory® at no upfront charge. We recognize that founders rarely have free cash flow before an exit. Our compensation is structured as a tiered, assets-under-management wealth-management arrangement after closing, which keeps us aligned with your after-tax outcome. We discuss fees openly before any engagement begins.
This Is the Right Fit If You Are
This is not the right fit if your personal exit is expected to be under $20M.
Schedule a Confidential Discussion
Book an introductory call with our founder below.