Who we serve
For equity-compensated executives
Every quarter, a little more of your future lands on one stock. Aspirean helps executives unwind concentrated company stock, coordinate their investment management, and plan the tax consequences of every grant before the window opens.
The moment
What a grant asks of you, every quarter
An RSU vest is a decision to buy the stock at that day’s price, made by default. Holding vested shares while your salary and unvested grants already ride on the same company concentrates more than the portfolio shows.
The work is deciding what to sell, when, and what it costs in tax, then putting it on a schedule that runs whatever the news: a 10b5-1 plan adopted in an open window, ISO exercises sized so the AMT stays digestible, and a concentration ceiling the plan can live with.
Meet with usHow much is too much
Lower than the usual 10 to 15 percent, because your salary and unvested grants already ride on the same company. Our test: the position is too large when a 50 percent drop would change your family’s plans. We set the ceiling first and the selling schedule follows from it.
Selling as an insider
Adopt a Rule 10b5-1 plan in an open window, when you hold no material nonpublic information. It sells on a pre-committed schedule whatever you learn later. Officers and directors wait 90 to 120 days before the first trade; other employees wait 30. We design the schedule around your vesting calendar and your employer’s trading policy.
ISOs and the AMT
Exercise while the spread is small, or in annual tranches sized so the AMT stays digestible. The AMT taxes that spread even though no cash arrived, but much of it returns as a credit in later years. We model each tranche with your CPA before the exercise, not after the return is filed.
Questions we answer
The questions this moment asks.
Each one started as a question a client asked. The short answer is here; the full answer is a perspective of its own.
The stock keeps vesting and keeps climbing. How concentrated is too concentrated?
Lower than the usual 10 to 15 percent, because your salary and unvested grants already ride on the same company. Our test: the position is too large when a 50 percent drop would change your family’s plans.
Read the full answerI want to diversify, but I’m an insider. How do I sell without tripping over trading windows?
Adopt a Rule 10b5-1 plan in an open window, when you hold no material nonpublic information. It sells on a pre-committed schedule whatever you learn later. Officers and directors wait 90 to 120 days before the first trade; other employees wait 30.
Read the full answerMy ISOs are in the money. Should I exercise, and why does everyone warn me about the AMT?
Exercise while the spread is small, or in annual tranches sized so the AMT stays digestible. The AMT taxes that spread even though no cash arrived, but much of it returns as a credit in later years.
Read the full answerHow we work with you
The services this moment leans on.
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Investment Management
Evidence-based portfolios built for your goals, not this quarter’s headlines.
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Tax Planning & Coordination
In-house tax planning, coordinated with the CPA who prepares your return, so April stops bringing surprises.
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Risk Management Planning
The coverage you already hold, against what your plan actually needs, free of conflict of interest or perverse incentive.
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Financial Planning
A living plan for the decisions in front of you: exits, equity, income, education, the freedom to make a change.
The situation
A senior technology executive had roughly 90 percent of the portfolio concentrated in a single stock, accumulated through years of RSU vesting.
What we did together
We developed a long-short tax-loss harvesting strategy to unwind the position deliberately, generating losses along the way to absorb the gains the selling created, with a defined concentration target of 20 percent.
Where it landed
A single-stock position on a managed path from roughly 90 percent of the portfolio toward 20, without handing the difference to the IRS.
Drawn from a real engagement, with details generalized to protect the client’s privacy. Every situation is different; outcomes depend on circumstances and timing.
Offices
Three offices, one team.
Marin County, CA
6 Knoll Lane, Suite BMill Valley, CA 94941
(415) 383-8404
Marin County, CA · Mill Valley, CA · San Francisco Bay Area, CA
St. Joseph, MI
505 Pleasant St, Suite 401St. Joseph, MI 49085
(844) 687-5342
St. Joseph, MI · Benton Harbor, MI · Southwest Michigan
Chesterton, IN
160 Rail Rd, Suite 4Chesterton, IN 46304
(844) 687-5342
Chesterton, IN · Valparaiso, IN · Northwest Indiana
Frequently asked questions
The things you’re probably wondering.
Do you have a minimum asset level?
Yes. We best serve individuals with at least $1 million in investable assets, including 401(k) plan assets, or more complex financial situations. Our minimum annual fee is $7,500 for clients below that threshold.
How are you compensated?
We are a fee-only Registered Investment Advisor and a fiduciary, paid via a percentage of the assets we manage.
Who actually sells the shares?
The accounts stay in your name at an independent custodian, and sales of company stock follow your employer’s trading policy and, where you adopt one, your 10b5-1 plan. Our role is the decision and the coordination: what to sell, when, in what order, and what it costs in tax, worked out with your CPA before the window opens.
What about the taxes on a vest?
The withholding taken at vest is often less than the tax the shares create, which can leave a balance due in April. We estimate the year with your CPA, decide whether to sell shares at vest to cover it, and plan exercises and sales around your bracket rather than around the calendar.
Is this only for public-company executives?
No. Private-company equity raises the same questions with fewer exits: ISOs and the AMT, an 83(b) election on early exercise, tender offers and secondary sales, and how much of your net worth sits in paper you cannot yet sell. We plan those with your CPA and the company’s counsel.
Meet with us
Let’s talk.
We take on a limited number of new families each year, on purpose. If some version of this moment has arrived at your door, we’d like to hear from you.
Meet with us