Question 1

Who is this for?

Accepted Answer

Anyone making equity decisions where tax, hedging, or diversification tradeoffs matter:

Employees with RSUs, ISOs, NSOs, or options contracts
Founders sitting on pre-exit stock
Retirees with a pile of employer shares
Retail investors hedging positions or minimizing tax drag on their trades
CPAs and financial advisors planning for any of them

One ISO grant over a few months is enough to benefit; so is twenty asset types over a decade.

Question 2

Why does this work?

Accepted Answer

Most planning tools either pick one market scenario and design for it, or give you a range of probabilities you can't easily apply to your portfolio and tax situation. OptionsAhoy does neither. Every candidate plan is scored for you personally against potential market paths (neutral, bearish, or bullish) at once, to produce maximum values across all three combined. The optimizer searches for that plan using established traditional and quantitative finance methods. So whether the market trends up, sideways, or down, your plan was built to hold up along that path while keeping the upside from getting eaten by IRS and state bills.

Question 3

Is this financial advice?

Accepted Answer

No. OptionsAhoy is a planning and modeling tool. It tells you what the math says given your inputs. For personalized advice, talk to a CPA or CFP.

Question 4

How does the optimizer handle taxes?

Accepted Answer

The tax engine is tested against IRS publications for federal income tax, AMT, long-term capital gains, NIIT, and 50-state income tax. It factors in filing status and household income. 2026 test cases are available on request.

Question 5

What about AMT on ISO exercises?

Accepted Answer

Exercising ISOs doesn't trigger regular income tax. It does trigger AMT on the bargain element (FMV at exercise minus strike), which can create a significant tax bill in cash, on gains you haven't sold yet. The right plan depends on your income, AMT exemption, filing status, cash position, holding-period goals, and how the stock moves. Two decisions drive it each year: • How many ISOs to exercise: more exercise now means more AMT now, but also more shares qualifying for long-term capital gains later. • When and how many to sell: selling within two years of grant or one year of exercise is a disqualifying disposition (ordinary income); past those windows it's a qualifying disposition (LTCG). The optimizer searches hundreds of thousands of exercise-and-sell schedules against your equity picture, income, and filing status. It models AMT jointly rather than checking it after the fact, then picks the schedule that maximizes portfolio value, minimizes taxes, maximizes cash, or any weighted mix. A CPA can tell you the tax impact of a scenario you bring them; the optimizer tells you which scenario to bring.

Question 6

What about pre-IPO or private company stock?

Accepted Answer

OA models public tickers. If you hold pre-IPO shares, OA can plan what happens after IPO given your grants and strike prices. Pre-IPO valuation decisions (409A-based exercise planning, tender offers) are not yet modeled.

Question 7

Do you connect to my brokerage?

Accepted Answer

Not at beta. Manual entry takes a few minutes and keeps your brokerage credentials out of our system. Integrations are on the roadmap for post-beta convenience.

Question 8

Is my data private?

Accepted Answer

Yes. Your inputs are encrypted at rest, never sold, and not used for marketing. Access is invite-only during beta.

Question 9

How often should I use this?

Accepted Answer

Use it as often as you want, ideally at least once a month, to adjust your plan to current market conditions. Plans you created before will help you enter those conditions with a portfolio already aligned to them, and tax timing already optimized.

Question 10

What does this add if I already have a CPA or CFP?

Accepted Answer

A CPA correctly applies the tax rules; a CFP integrates planning across your goals. The trade picks themselves — which lots to sell, when, in what order — typically come from professional judgment, not systematic search, modeled case by case. That work costs thousands of dollars per engagement and is slow to re-run when conditions change. OA searches across hundreds of thousands of candidate plans in minutes and lets you re-run whenever you want. Your CPA or CFP remains the right partner for personalized advice, audit defense, and filings; OA gives you the optimization math underneath.

Question 11

What does it cost?

Accepted Answer

Beta is free: no credit card, no usage limits. Pricing will be set before general availability; beta users will get advance notice.

Capability	Traditional tools	OptionsAhoy
Tax optimization	Tax is separate from investment planning	Optimizes the tax impact of your equity decisions: federal, state, AMT, capital gains, and NIIT calculated together with your personal income and financial goals
Scenario modeling	Single forecast or manual what-if	Every strategy stress-tested across bullish, neutral, and bearish markets simultaneously
Risk reduction	You decide when to hedge	Optimizes protective puts and long calls to limit downside exposure at minimum cost
Income generation	Manual setup, one strategy at a time	Optimizes covered calls and cash-secured puts to generate income from existing positions
Actionable output	Charts you interpret yourself	Month-by-month action plan: what to sell, exercise, or hedge, and when
Multi-year planning	Single year at a time	Optimizes across 3 months to 10 years, with every tax and vesting event in context

Your equity, actually optimized.

Three advisors, three tools, nobody optimizing them together.

Take three steps in 5 minutes. Plan your best trades from a few months to 10 years ahead.

Enter your holdings

Set your goals

Get your plan

What you get that traditional tools can’t give you.

A month-by-month action timeline, not a chart you interpret.

Things people ask us.

Request access to the Beta.