QSBS Specialist Advisory for Venture-Backed Founders
Keystone Global Partners works with venture-backed tech founders to plan, structure, and implement QSBS strategies before and during an exit.
You spent years building your company. When it’s time to sell, Section 1202 of the tax code could let you exclude millions of dollars in gains from federal taxes.
But the rules are complicated. Miss a detail, and you could owe millions more than necessary. Our co-founder, Peyton, is recognized as one of the leading QSBS specialists in the country, with deep expertise in practical implementation for $20M+ exits.
KEYSTONE RECOGNITION
How the Process Works
Step 1
Initial Conversation
We learn about your company, your stock position, and your exit timeline.
Step 2
Qualification Review
We assess your shares against Section 1202 requirements and calculate your exclusion potential.
Step 3
Strategy Development
We build a plan covering exclusion maximization, stacking, trust planning, and state tax.
Step 4
Ongoing Advisory
As your situation changes, we update the strategy and coordinate with your attorneys and CPAs.
Step 5
Post-Exit Transition
After your liquidity event, we move into full wealth management to protect and grow what you’ve built.
QSBS Specialist Advisory Services
01
Section 1202 Exclusion Analysis
Before building any strategy, we confirm your stock qualifies and determine what exclusion percentage applies.
The One Big Beautiful Bill Act (OBBBA), signed July 4, 2025, created new rules for stock acquired after that date. Stock issued on or before July 4, 2025 remains under the prior rules.
Your exclusion depends on when your stock was issued:
| Stock Issued | Holding Period | Exclusion |
|---|---|---|
| After September 27, 2010 and on or before July 4, 2025 | More than 5 years | 100% |
| After July 4, 2025 | Less than 3 years | 0% |
| After July 4, 2025 | At least 3, less than 4 years | 50% |
| After July 4, 2025 | At least 4, less than 5 years | 75% |
| After July 4, 2025 | 5+ years | 100% |
Stock acquired before September 28, 2010 falls under legacy 50% or 75% tiers with different AMT treatment.
We also review your company’s eligibility based on entity type, company gross assets before and after stock issuance, and the active business requirement. The aggregate gross assets test caps company assets at $50 million for stock issued on or before July 4, 2025, and $75 million for stock issued after that date, measured using cash + the adjusted tax basis, rather than fair market value, at all times before and immediately after issuance.
Note: for stock issued after July 4, 2025, the exclusion cap is the greater of $15 million or 10 times your adjusted basis, per taxpayer, per issuer (the $15 million is indexed for inflation beginning in 2027). For stock issued on or before that date, the cap is the greater of $10 million or 10 times basis.
02
Mixed Tranche Analysis
Most founders hold multiple stock positions with different acquisition dates and different rules. Founder shares from 2019, options exercised in 2022, and shares issued in late 2025 under the new rules each follow their own exclusion percentage, holding period, and cap.
We analyze every tranche separately, calculate the total exclusion potential across all positions, and flag any gaps before they become a problem at closing.
03
Exit Timing Strategy
For founders holding post-OBBBA stock, a few months can make a significant difference. Waiting from three to five years of holding moves a founder from a 50% exclusion to a 100% exclusion. On a $15 million gain, the difference in federal taxes is over $2 million.
We model whether adjusting your exit timeline makes financial sense, factoring in deal certainty, market conditions, and your personal goals.
04
Deal Structure Review
How your deal is structured determines whether you keep your QSBS benefit.
| Deal Structure | QSBS Treatment |
|---|---|
| Direct stock sale | Section 1202 exclusion preserved |
| Asset sale | Exclusion generally eliminated |
| 338(h)(10) election | Treated as asset sale; exclusion generally eliminated |
| Stock-for-stock merger (Section 368) | Exclusion preserved up to built-in gain at closing; future appreciation generally not covered |
We review purchase agreement terms and tax elections before you sign to catch any structural issues that could wipe out an exclusion you spent years building.
05
QSBS Stacking Strategies
If your exit exceeds the exclusion cap, stacking can expand your total tax benefit. Stacking works by gifting shares to multiple qualified taxpayers before the exit. Each separate taxpayer qualifies for their own exclusion cap.
Example: how stacking expands total exclusion (post-OBBBA stock)
| Taxpayer | Per-Issuer Exclusion Cap |
|---|---|
| Founder | $15M |
| Non-grantor trust (first) | $15M |
| Non-grantor trust (second) | $15M |
| Family member (separate taxpayer) | $15M |
| Total potential exclusion | $60M |
A few things that matter here:
- Grantor trusts do not create a separate taxpayer and will not multiply your exclusion
- Non-grantor trusts are separate taxpayers and can qualify for their own cap if drafted correctly.
- Multiple trusts must be meaningfully different (beneficiaries, trustees, terms). Carbon-copy trusts can be collapsed into one taxpayer under Section 643(f)
- Transfers made after a sale is practically certain could fail, and be considered an assignment of income by the IRS
A true QSBS specialist understands that timing is everything. Stacking requires planning well ahead of any LOI or exclusivity agreement.
06
Trust Planning and Entity Structuring
As QSBS specialists, we coordinate with qualified tax and legal professionals to align your QSBS strategy with your broader trust and estate goals.
Services in this area include:
- Non-grantor trust and other types of structuring to expand the total exclusion
- QSBS Packing, if applicable
- Charitable planning
- Generation-skipping trust planning for multi-generational wealth transfer
- Family office coordination
07
State Tax Planning
Federal exclusion is only part of the picture. State treatment varies significantly.
| State | Conforms to Federal QSBS? | Notes |
|---|---|---|
| California | No | 13.3% state capital gains tax still applies |
| Pennsylvania | No | Does not conform |
| Alabama | No | Does not conform |
| Mississippi | No | Does not conform |
| Washington D.C. | No | Decoupled retroactive to January 1, 2025 (temporary legislation; status evolving) |
| Oregon | No | Addback required for tax years beginning on or after January 1, 2026 |
| New Jersey | Yes | Conforms starting January 1, 2026 |
| New York | Yes | Full conformity, including for NYC residents |
| Most other states | Yes | Generally follow the federal exclusion, though several states have partial or evolving rules. State treatment is a moving target and should be verified for your situation |
We help founders understand their full state tax exposure and plan accordingly. That may include residency planning (24 to 36 months before exit offers the most planning room), non-grantor trust structures in conforming jurisdictions, and timing strategies for founders in recently updated states.
08
Section 1045 Rollover Planning
If you sell QSBS you have held for more than six months but have not yet met the exclusion holding period, a Section 1045 rollover lets you defer tax by reinvesting proceeds into new qualifying stock within 60 days of the sale. Your original holding period carries over to the replacement stock.
This is a deferral strategy, not a permanent exclusion. It works best when you plan to deploy capital into another qualifying startup. We model whether it fits your exit, and we handle the coordination so the replacement stock stays on track for its own future exclusion.
Personal Exit Advisory Program
If your exit is between zero and three years out, please reach out to discuss our Personal Exit Advisory® program.
The goal is simple: the planning decisions you make before your exit determine how much of your exit you actually keep. By the time you have an LOI on the table, some options are no longer available.
This program covers:
Learn more about our Personal Exit Advisory® program.
Who Keystone Works With
Keystone serves venture-backed tech founders who are approaching or planning a liquidity event of $20 million or more.
You are a good fit if:
We specialize in working with founders in California and New York, and across tech ecosystems nationwide.
Post-Exit Wealth Management
After your exit, Keystone moves into a full wealth management relationship. Because we worked with you during the pre-exit phase, we already know your goals, your financial picture, and what matters to you. That continuity matters.
Post-exit services include:
What Most Advisors Get Wrong
QSBS planning is not a checklist. The rules interact in ways that depend on your specific situation.
A few mistakes we see regularly:
Each of these errors can cost millions. Catching them requires a QSBS specialist who regularly works in this space.
GET STARTED
Connect with Our Founder
If you are a venture-backed founder with a potential exit on the horizon, the time to review your QSBS position is now, not after you have signed a term sheet.
Connect with our founder to discuss your specific situation.