A preview of the personalised planning workspace · NYC Edition · 2026
This toolkit is provided for informational and educational purposes only and does not constitute legal, tax, or investment advice. Allegiance Partners does not act as your attorney or CPA. Please consult your own CPA and/or attorney before executing any strategy described here.
City
New York, NY
Entity
Delaware C-Corp
Incorporated
2022
Current valuation
$15M
Target exit
$75M · ~2029
Founder ownership at exit
50%
Dynasty Trust
5% — fund now
QSBS clock
2022 → 2027
NYC blended tax
38.6%
Trust situs
Delaware
Overall roadmap progress
0%
This is a live, interactive tool — every founder's roadmap is built around their own cap table, incorporation date, and exit timeline. Click into any step below to see the level of detail a real workspace would include.
This roadmap shows the planning steps that give an exit — and the wealth it creates — the best possible foundation. Some steps have a natural sequence; John will help the founder think through timing as their picture develops.
1
2026
Foundations
0/5 complete
Basic estate planLegal
Will, power of attorney, healthcare proxy. Worth adding a pre-marital agreement if marriage is planned — assets placed in trust before marriage are protected.
Dynasty Trust — fund nowTrust
A Delaware perpetual trust funded with shares at today's valuation. Assumes the company's incorporation date under §1202(h)(2) — locking in the founder's QSBS clock for the trust as well. Usually the most time-sensitive planning step.
Grantor vs non-grantor trust electionTaxTrust
As a grantor trust, the founder pays the trust's income tax personally each year — an additional tax-free gift to the trust. As a non-grantor trust, the trust pays its own tax and stacks its own QSBS exclusion separately. T&E counsel advises which fits the founder's goals.
Appoint T&E counselLegal
NYC trusts and estates specialist with Delaware situs expertise. Often the most important advisor appointment in the plan.
Appoint CPA / tax advisorTax
NYC and NYS tax specialist who can model the QSBS exclusion, the exit waterfall and the estate tax cliff effect.
2
2026–2027
Charitable structure
0/4 complete
Establish Donor Advised Fund (DAF)Tax
A DAF is often the right vehicle for founders at this stage — fast to establish, simple to run. John helps identify the right sponsor and confirms the pre-sale gift strategy with T&E counsel.
Establish charitable vehicleLegalTax
Once decided, set up and fund the vehicle — in place well ahead of the exit horizon.
Pre-exit charitable gift strategyTax
A gift of shares before any LOI is signed — timing relative to the sale process is critical and co-ordinated by T&E counsel and John.
Dynasty Trust participates in any funding roundTrust
Ensure the Trust maintains its equity position through any further investment rounds.
3
2027–2028
Pre-exit preparation
0/4 complete
Beneficiary decisionsTrust
Children (current or future) are typically the intended beneficiaries. John helps founders think through the right structure at their own pace.
NY estate tax planningTax
With a $7.16M cliff exemption, keeping assets outside the taxable estate via the Dynasty Trust and PPLI is important. The CPA models the estate position at exit.
Appoint M&A counselLegal
Transaction specialist, engaged ahead of any formal sale process.
Pre-exit tax waterfall modelTax
Full scenario analysis across personal proceeds, trust, charitable vehicle and investor shares at multiple exit valuations.
4
2028–2029
Final preparation
0/3 complete
Confirm QSBS positionTax
Formal confirmation of the founder's and the Dynasty Trust's QSBS qualification with CPA and T&E counsel ahead of any deal process.
Dual-class share structureLegal
Confirm voting control through to exit — enhanced-voting share classes can protect founder position through the sale process.
Investor alignmentLegal
Confirm investor exit expectations and how proceeds will flow across the cap table.
5
~2029
Exit
0/5 complete
Pre-sale charitable giftTax
Transfer of shares to the charitable vehicle before any LOI is signed. Timing is everything — co-ordinated by T&E counsel and John.
Full advisor alignmentLegal
T&E counsel, M&A counsel, CPA and John all working from the same plan before anything is signed.
Sign LOI and closeLegal
With full structural clarity across personal proceeds, Dynasty Trust, charitable vehicle and investor shares.
Closing DayTrust
The Dynasty Trust sells its shares. Proceeds flow to the Trust — ready for Level 2 deployment.
Post Exit Tax Planning deploymentEst. Freeze
After Closing Day, the Family Trust's Grantor Trust election is confirmed with counsel — locking in tax-free growth for the next generation while the founder covers the trust's tax bill personally. PPLI remains available as a more advanced, later-stage option for founders who outgrow this default approach.
This illustrative base case is a $75M exit with 50% founder ownership at sale. The cap table splits across the founder's personal holding, investors, a Dynasty Trust and an optional charitable gift. Move the sliders to explore different outcomes — all four shares should add up to 100%.
$75M
50%
40%
5%
5%
100%
38.6%
Exit valuation
$75.0M
Founder gross proceeds
$37.5M
Investors receive
$30.0M
Dynasty Trust
$3.8M
Charitable gift
$3.8M
Charitable deduction
$2.8M
QSBS exclusion
$10.0M
Tax bill
$9.2M
Founder net personal
$24.6M
Without planning
$23.0M
Total family wealth
$32.1M
Planning advantage
+$9.1M
Cap table: founder 50% · investors 40% · trust 5% · charity 5% = 100%. Planning saves $9.1M compared to an unstructured exit at NYC rates — a 39% improvement. Dynasty Trust proceeds of $3.8M available for Level 2 PPLI after Closing Day.
An illustrative QSBS position. This example company was incorporated in 2022 — the 5-year holding period completes in 2027, about a year away. At a $75M exit the founder's shares are worth $37.5M (50% ownership). The federal exclusion alone could save over $2M in tax. A Dynasty Trust funded now assumes that same 2022 date under §1202(h)(2) and can access its own separate $10M exclusion once qualified.
Incorporated
2022
5-year hold completes
2027
Founder exclusion
$10M (2027)
Trust exclusion
$10M (fund now)
Combined potential
$20M
NYC tax saved
$7.7M
NYC vs NJ advantage
+$810,000
Taxpayer
QSBS exclusion
Status
Tax saved at 38.6%
Founder
$10,000,000
Incorporated 2022 — qualifies 2027
$3,860,000
Dynasty Trust
$10,000,000
Assumes 2022 date under §1202(h)(2) — fund trust now to secure
$3,860,000
Combined potential
$20,000,000
Confirm with T&E counsel and CPA
$7,720,000
NYC tax context
NYC founders pay federal, NY State and NYC city tax on exit proceeds — a combined blended rate of approximately 38.6%. This is meaningfully higher than neighboring states and makes the QSBS exclusion and post-exit trust planning especially valuable. A grantor trust — where the founder pays the trust's income tax personally — is particularly compelling at this rate, since it effectively becomes an additional tax-free gift to the trust each year.
Tax layer
Rate
Notes
Federal long-term capital gains
20.0%
QSBS exclusion applies here first
NIIT (ACA surcharge)
3.8%
On net investment income
NY State income tax
10.9%
NYS conforms to federal QSBS treatment ✓
NYC city surcharge
3.876%
Additional city layer — unique to NYC residents
Combined blended rate
38.576%
Every $1M of QSBS exclusion saves ~$386K
NY estate tax — the cliff effect
New York's estate tax exemption is approximately $7.16M — but with a cliff effect: if an estate exceeds 105% of the exemption, the entire estate is taxed, not just the excess. On top of the federal estate tax of 40%, NYS can add up to a further 16% — a combined rate of up to 50%+ at death before anything reaches the next generation. This makes keeping assets outside the taxable estate — via a Dynasty Trust structured as an estate freeze — especially important for NYC-based founders. See Post Exit Tax Planning.
After an exit, the Dynasty Trust's proceeds can keep compounding under an Estate Freeze — a well-established, easily explained structure that uses a Grantor or Non-Grantor Trust election, with no specialized insurance product required. If the founder elects grantor trust status, they pay the trust's income tax personally each year — the trust grows tax-free, and the payment itself is treated as an additional tax-free gift to the trust. Combined with the assets sitting entirely outside the taxable estate, this can dramatically outperform holding everything personally. Federal and NY estate tax (40% federal above a $15M exemption; 16% NY above a $7.16M exemption, with a 105% cliff) are held fixed per current law; adjust the other illustrative assumptions below.
37
82
6.5%
38.6%
Unplanned
Everything held personally — no trust
$54.1M
Income tax on gains annually, then full Federal + NY estate tax at death before reaching the next generation
Non-Grantor Trust
Trust pays its own income tax — separate taxpayer
$66.4M
Trust assets sit outside the estate, but there's no additional tax-free gift from the founder each year
Grantor Trust ★
Founder pays the trust's income tax personally
$89.9M
Each tax payment is an additional tax-free gift to the trust — and the trust passes to the next generation free of estate tax
Unplanned held personally
Non-Grantor Trust separate taxpayer
Grantor Trust founder pays trust's tax
Advantage vs Unplanned
Year 5 (age 42)
$16.0M
$18.6M
$18.9M
$2.9M
Year 10 (age 47)
$18.2M
$21.3M
$22.2M
$3.9M
Year 15 (age 52)
$20.9M
$24.6M
$26.3M
$5.4M
Year 20 (age 57)
$24.1M
$28.7M
$31.5M
$7.4M
Year 25 (age 62)
$28.0M
$33.6M
$38.1M
$10.1M
Year 30 (age 67)
$32.7M
$39.5M
$46.6M
$13.9M
Year 35 (age 72)
$38.5M
$46.8M
$57.6M
$19.0M
Year 40 (age 77)
$45.6M
$55.6M
$71.6M
$26.1M
Year 45 (age 82)
$54.1M
$66.4M
$89.9M
$35.7M
At life expectancy (age 82, 45 years): the Grantor Trust election delivers $89.9M to the next generation — compared to $54.1M held personally with no planning. That is $35.7M more, a 1.7× improvement. Life expectancy defaults from the SSA 2023 Period Life Table based on age and gender, and is adjustable.
A well-structured exit works best with a co-ordinated team. John will help identify and introduce the right specialists at each stage — the founder does not need everyone in place at once, the team builds naturally as the plan develops.
Wealth strategist
John Alexander
Allegiance Partners
Available — book a Discovery Call
Trusts & estates counsel
To be identified
NYC specialist Delaware trust situs expertise
Introduced when needed
CPA / tax advisor
To be identified
NYC & NYS tax specialist QSBS & exit waterfall
Introduced when needed
Charitable vehicle
Donor Advised Fund (DAF)
Sponsor selected with John if charitable giving is a goal