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.

Executives & Equity-Comp Professionals

RSUs, ISOs, ESPP, and a concentrated position that's done very well, now carrying real risk and tax baggage. Dogpatch Wealth builds tax-aware diversification plans for SF Bay Area executives and tech leaders.

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The Concentrated-Stock Problem Most Executives Face

Years of RSUs, ISOs, and ESPP purchases add up, and one day you look at the statement and a single company stock has quietly become most of your net worth. That position did very well, and now it carries real risk and real tax baggage. The challenge is unwinding the concentration without handing a fortune to the IRS in a single year.

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RSU, ISO & ESPP Planning

Each form of equity comp has its own playbook. We typically treat RSUs like a cash bonus at vest, selling to control concentration rather than buying more company stock. For ISOs we model the spread, the AMT impact, and your holding period to time exercises deliberately. For ESPP we capture the discount while keeping your overall exposure in check, all coordinated with the rest of your plan.

Concentrated Stock Diversification & Tax Strategy

There is no single button for diversifying a large position, but several levers used together help: direct indexing with ongoing tax-loss harvesting, selling in planned stages across tax years, gifting or charitable strategies, and timing sales around lower-income years. We model the after-tax outcome and build a multi-year plan rather than a one-time dump.

Concentrated Stock

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Coordinating Equity Comp With Your Full Financial Plan

Equity comp does not live in a vacuum. We fold your vesting schedule, tax withholding gaps, and concentration risk into the same plan that covers your cash flow, retirement, and family goals, so each vest and each sale is a decision that fits the whole picture rather than a scramble against a deadline.

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Pre-IPO & Post-IPO Planning

The window around an IPO is dense with decisions and short on time. Before the event we screen QSBS eligibility, model 10b5-1 plans, and put structures in place while they still work. After the event we manage the transition from paper wealth to a diversified, tax-aware portfolio. Starting early is the single biggest advantage you have.

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WHAT WE DO

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Investment Management

Concentrated single-stock positions get diversified with intent, not with a template — 10b5-1 plans, ISO/NSO exercises, and post-sale reinvestment done in the open with you.

See how we invest

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QSBS & Trust Stacking

For founders sitting on qualified small-business stock, we coordinate with counsel on non-grantor trust structures that can multiply the exclusion. It is niche work, and it is done here.

Talk about QSBS

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Tax Planning

RSU vests, AMT exposure, and QSBS eligibility get modeled before the calendar year closes — not after, when the options are gone.

Tax Planning

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Dogpatch Venture Fund

Clients get access to the Dogpatch Venture Fund — a proprietary fund-of-seed-stage-funds that leverages SF relationships. Nearly 200 underlying companies in year one.

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Frequently Asked Questions

There is no single button, but several levers used together help: direct indexing with ongoing tax-loss harvesting, selling in planned stages across tax years, gifting or charitable strategies, and timing sales around lower-income years. We model the after-tax outcome and build a multi-year plan rather than a one-time dump.
It depends on the spread, the AMT impact, your holding period, and your view on the stock. We model exercise scenarios against your full tax picture to find the timing that captures favorable long-term treatment without an avoidable AMT surprise. The goal is a deliberate plan, not a deadline-driven scramble.
Treat each vest like a cash bonus you would not use to buy more company stock. We typically plan to sell at vest to control concentration, cover the tax withholding gap, and redeploy into a diversified, tax-aware portfolio, all coordinated with your other equity and your goals.
It may be. QSBS (Section 1202) generally requires C-corporation stock acquired at original issuance, a company under the gross-asset threshold when issued, and a 5-year hold. We help you screen eligibility early and, where it fits, coordinate trust-stacking strategies before a liquidity event.
Yes. We regularly advise executives and employees across San Francisco and Silicon Valley tech, finance, and biotech employers on RSUs, ISOs, ESPP, 10b5-1 plans, and concentrated positions. We tailor the plan to your specific equity package and company situation.
Existing limited partners log in at dogpatchfunds.com. Your credentials are issued at onboarding.

Executives & Equity-Comp Professionals

RSUs, ISOs, ESPP, and a concentrated position that's done very well, now carrying real risk and tax baggage. Dogpatch Wealth builds tax-aware diversification plans for SF Bay Area executives and tech leaders.

The Concentrated-Stock Problem Most Executives Face

RSU, ISO & ESPP Planning