What is a Certified Exit Planning Advisor (CEPA)?

A Certified Exit Planning Advisor (CEPA) is a credentialed professional trained to help business owners plan the transition or sale of their business. CEPAs coordinate legal, financial, and tax strategies to maximize the value an owner receives from their exit. Adam Gould is one of the few financial advisors in San Francisco who holds this designation.

Do you work with startup founders and tech executives?

Yes. Dogpatch Wealth focuses specifically on founders, executives, and early employees at Bay Area tech companies who are navigating liquidity events, IPOs, or significant equity compensation. Adam Gould has deep experience with equity planning across a variety of vesting structures and exit scenarios.

What is the minimum investment or AUM to work with Dogpatch Wealth?

Dogpatch Wealth works with clients who typically have $1 million or more in investable assets or are expecting a near-term liquidity event. The firm is selective to ensure each client receives highly personalized, ongoing advisory support.

What does exit planning mean for a business owner?

Exit planning is the process of preparing a business owner for the eventual transition or sale of their company — whether to a third party, private equity, or family members. It encompasses valuation, tax minimization, estate planning, and personal financial readiness. Dogpatch Wealth helps owners build a plan years before an exit so they can maximize proceeds and avoid costly mistakes.

Is Dogpatch Wealth a fee-only financial advisor?

Yes. Dogpatch Wealth is an independent, fee-only registered investment advisor. Adam Gould does not earn commissions or referral fees from product sales. This fiduciary model aligns his incentives entirely with client outcomes.

How can I diversify a concentrated stock position without triggering a large tax bill?

There is no single answer — the right approach depends on your cost basis, time horizon, income, and goals. Common tax-aware strategies include: gradual systematic selling spread across multiple tax years to manage annual capital gains exposure; exchange funds, which allow qualified investors to contribute a concentrated position to a diversified fund without immediately realizing capital gains (subject to a minimum seven-year lock-up); charitable giving vehicles such as donor-advised funds or charitable remainder trusts, which can eliminate the capital gains tax on donated shares; and hedging overlays or structured products that provide downside protection while keeping the position intact. Dogpatch Wealth evaluates the full trade-off — tax cost, concentration risk, liquidity needs, and fee drag — to recommend the strategy that fits your situation.

What are the risks of holding a concentrated position in a single stock?

The core risk is that a single company's fate can swing your entire net worth. Historically, most individual stocks underperform a broad market index over their lifetimes — and a significant portion lose money outright. Even stocks that were once exceptional performers often give back their gains: past winners do not reliably continue to outperform. Keeping a concentrated position also tends to increase portfolio volatility, which over time compounds into slower wealth growth even in favorable scenarios. The reluctance to sell is understandable — tax bills are real and emotional attachment to a stock that built your wealth is natural. But it helps to separate the question of whether the company will do well from the question of whether your concentrated exposure to it is the right risk for your financial plan.

Multiply your
QSBS exclusion

QSBS trust stacking lets eligible founders multiply the $15M per-taxpayer Section 1202 exclusion across properly structured non-grantor trusts — turning one exclusion into several.

Book A Consult

GAIN EXCLUSION MATH

$15 Million

The federal QSBS gain exclusion per taxpayer, per issuer (stock issued after July 4, 2025 under OBBBA).

$60 Million

Founder/Investor + spouse + two non-grantor trusts. Four taxpayers.

Same exit. Same equity. Very different return to the family.

FIGURE 1 — FEDERAL GAIN SHELTERED ON A $60M EXIT

Stacked bars showing how the $60M moves from federally taxable into the QSBS-exclusion column as you add non-grantor trust taxpayers.

QSBS trust stacking gain exclusion chart

FIGURE 2 — FEDERAL TAX OWED AT EXIT

On a $200M exit, a four-taxpayer stack may shelter roughly $14M more in federal tax than a single taxpayer — same exit, same equity.

Take the Intake Quiz

2 minutes, no email required. The Intake Quiz takes your equity and family situation and recommends a structure. The fastest way to know whether this page applies to you.

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Run your own facts.

Run your own numbers. Book a consult and we’ll model your exact equity and family situation in a personalized Promissory illustration.

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HOW THE STRATEGY WORKS (4 STEPS)

Identify

Confirm eligibility and model the stack against the founder's cap table.

Transfer

Gift qualifying stock well before a liquidity event. Gifting inside 12 months of a signed LOI is a no-go zone —recharacterization risk spikes.

Design

Choose the right structures. SLATs (grantor) do NOT stack; SLANTs, NGTs, non-grantor IDGTs do.

Realize

At exit, each properly structured trust claims its own §1202 exclusion.

Dogpatch brings the advisory relationship. Promissory brings the trust infrastructure — drafting, valuation, and administration.

Who qualifies for QSBS trust stacking

Domestic C-corporation issuing the stock.
Most VC-backed software, hardware, biotech, climate companies qualify.
Gross assets under $75M at original issuance (post-OBBBA).
Five-year holding period for the full 100% exclusion (50% at 3 years, 75% at 4 years under OBBBA).
12–24+ months of runway pre-liquidity. Inside 12 months is a no-go zone.
Best fit: Seed through Series B. Series C possible with the right timeline.

On the live page, founders pre-screen against these chips visually, then jump into the Intake Quiz for a structured assessment.

FAQ’s

QSBS trust stacking is the practice of allocating qualifying Section 1202 stock across multiple eligible taxpayers — typically the founder, spouse, and one or more properly structured non-grantor trusts — so each can claim its own $15M federal exclusion at exit. It’s mainstream §1202 planning when done early, and risky inside 12 months of an LOI.
Planning should begin 18–24 months before a likely liquidity event. Inside 12 months, recharacterization risk rises sharply, and after a signed LOI the window is effectively closed for new structures.
No — California does not conform to federal §1202 and continues to tax the gain at ordinary state rates. QSBS trust stacking is a federal benefit; California outcomes depend on trust situs, beneficiary residency, and source rules.
No — Dogpatch coordinates with your existing CPA and attorney rather than replacing them. Promissory’s panel attorneys handle the trust drafting, with sign-off pathways for your own counsel.
Promissory’s platform fee is a transparent $7,500 standard package covering up to four trusts, attorney review, valuation, and tax-form prep, plus $1,500/yr trust custody after year one. The Dogpatch advisory overlay is scoped after the initial consult.
No — properly structured QSBS trust stacking is recognized §1202 planning that venture-backed founders have used for two decades. Real trusts, real beneficiaries, real administration, real holding periods. We turn down fact patterns that don’t support it.

DISCLAIMER

Educational only. Not tax or legal advice. Tax outcomes depend on individual facts and circumstances and may vary. Any potential tax savings discussed are illustrative and not guaranteed. California does not conform to federal QSBS treatment. Dogpatch Wealth coordinates with your CPA and attorney; we do not replace them. Services provided in partnership with Promissory

Multiply your
QSBS exclusion

QSBS trust stacking lets eligible founders multiply the $15M per-taxpayer Section 1202 exclusion across properly structured non-grantor trusts — turning one exclusion into several.