The tools that let you test different stock option exercise strategies include Secfi, DQYDJ, Erik Barbara’s ISO Tool, Carta, and EquityList.
Deciding how to handle your equity is often the most significant financial decision of your career, yet most spreadsheet models fail to account for the interplay between alternative minimum tax (AMT) and exit timing.
Secfi provides a specialized platform that combines automated data import with advanced scenario modeling to help you visualize the long-term impact of your exercise choices.
Comparison of equity testing tools
ToolTypeIdeal forKey featuresSecfiStrategy platformEmployees and executives modeling complex equity, tax, and liquidity decisionsAdvanced scenario modeling, AMT projections, Carta sync, Maeve AI assistant, liquidity financingDQYDJ ESO CalculatorLightweight calculatorQuick estimates of ISO exercise costs and taxesSimple AMT checks, ISO/NSO breakdowns, net proceeds estimatesErik Barbara’s ISO ToolAMT planning calculatorDetermining how many ISOs to exercise without triggering excessive AMTAMT threshold calculations, ISO-focused tax planningCarta Exercising SimulatorEquity admin simulatorEmployees whose companies already use CartaVesting simulations, exercise presets, pre-tax cost estimatesEquityListEquity management platformCompanies and employers managing equity across multiple jurisdictionsGrant tracking, valuation visibility, document management dashboards
For Illustrative Purposes only
Use lightweight tools for quick checks
If you only need a high-level view of your potential tax bill, we feel lightweight calculators are a fast way to get numbers without a full account setup. These tools are helpful when you are in the first round of research and want to know if exercising your options is even financially feasible.
DQYDJ ESO Calculator
This tool is designed for a quick check of Incentive Stock Option (ISO) costs. You input your grant details and estimated tax rates to see a breakdown of net proceeds and worst-case tax scenarios.
Ideal for: Rapid "back of the envelope" calculations.
Key features:
- Models three hold-and-sell strategies based on the one-year and two-year holding requirements.
- Displays the bargain element that factors into your Alternative Minimum Tax (AMT) calculation.
- Shows estimated net proceeds after accounting for capital gains tax.
Erik Barbara’s ISO Tool
This is a focused planning tool specifically for managing AMT, which only applies to ISO grants. Many employees realize too late that the longer they wait, the more expensive exercising becomes because the gap between the strike price and fair market value (FMV) grows.
Ideal for: Avoiding the AMT "cliff." – the point where exercising additional ISOs suddenly creates a much larger tax bill due to AMT exposure.
Key features:
- Helps you determine the exact number of options you can exercise to stay under the AMT threshold.
- Simplifies specialized tax logic that most generic financial tools ignore.
Use strategy modeling platforms for deeper insights
As a company grows, we have found that simple calculators often fall short because they cannot interpret your stock option vesting schedule or model multiple exit valuations simultaneously.
“When stakes are high, testing a strategy should be a collaborative problem-solving exercise. Having an expert who can speak the lingo and coordinate with your existing accountants or lawyers ensures that every party agrees on the tax treatment before you move forward.” – John Klingler, Equity Strategist at Secfi
Strategy platforms allow you to test "what-if" scenarios that reflect your specific financial goals, such as buying a home or leaving the company.
Secfi: One of the leading choices for comprehensive strategy modeling
Secfi is a specialized platform built to handle the complexities of equity compensation that traditional wealth tools miss. Most generic models assume liquid assets and predictable returns, but equity requires you to factor in 409A valuations and uncertain exit timelines.
The platform uses a proprietary calculation engine to model exactly how different strategies impact your taxes and long-term wealth. By importing your data directly from Carta or uploading grant documents, you can see the math behind every scenario.
Read more: How to value stock options in a job offer letter
Ideal for: Employees and executives with complex equity situations who want to model multiple exercise, tax, and liquidity scenarios before making a decision.
Key features:
- Automated data sync from platforms like Carta or uploaded grant documents
- Advanced scenario modeling for exercising, holding, selling, or financing equity
- AMT projections and AMT credit recovery modeling
- Maeve AI assistant for testing personalized “what-if” equity scenarios
- Liquidity solutions, including non-recourse financing for exercise costs and taxes
- Access to equity specialists who understand ISO, NSO, and pre-IPO tax complexities
- Access dashboards to track vesting events and track monetary growth over time.
Carta Exercising Simulator
Carta is primarily an equity administration tool used by companies to manage their cap tables, but it offers a simulator for individuals who hold grants on their platform.
Ideal for: Employees whose companies already use Carta for equity management.
Key features:
- Presets for "Exercise All Vested" or "Customize Your Exercise."
- Automatically updates vested amounts when you change the simulated exercise date.
- Estimates pre-tax costs by multiplying share quantity by the strike price.
- Use dashboards to track vesting events and growth.
Read more: Deciding when to hire a financial advisor for your equity
Use full stack equity tools for overall management
Some tools are designed to provide an end-to-end view of equity for both founders and employees. These are useful for seeing how your ownership fits into the broader company structure.
EquityList
EquityList is an administration platform used by hundreds of companies to oversee grants, lapses, and exercises. It focuses on providing transparency through a centralized dashboard.
Ideal for: Employers with global teams who need to track equity & shares across different jurisdictions
Key features:
- Provides real-time visibility on valuation updates.
- Simplifies the exercise process with built-in document management.
- Offers dashboards that celebrate vesting events and track monetary growth over time.
How to choose the right tool
We believe selecting a tool depends on the complexity of your situation and the dollar value at risk. If you are an early-stage hire with a small tax burden, a lightweight calculator may be enough. If you are an executive or a late-stage employee with six-figure tax implications, you need a platform that offers more nuanced calculations.
“Many startup employees wait until they are forced to act by a deadline or a liquidity event, but that is often when it is too late to manage the costs on their own. The most effective planning happens before you are in a high-pressure situation, allowing you to avoid being caught off guard by a multi-million dollar tax bill.” – John Klingler, Equity Strategist at Secfi
Criteria to consider when evaluating tools:
- Data accuracy: Does the tool pull real-time market data or rely on user-entered estimates?
- Tax depth: Can it handle the difference between federal and state tax systems, including the AMT?
- Actionability: If the tool models a strategy you cannot afford, does it offer pre-IPO liquidity solutions?
- Expert oversight: Is there a human strategist available to help you navigate gray areas that software might miss?
Test your strategies before exercising
We feel checking your stock option strategies is about more than just finding the lowest tax bill. It is about making an informed decision and creating flexibility in your financial life.
When you use tools to model these scenarios, you gain a grounded sense of what your equity is actually worth, and how much it will cost to exercise rather than relying on a 10 year old strike price or the latest headline in making your decision.
The reality is that most people wait until they have a deadline to take action, but by then, the cost of exercising may have grown out of reach.
By testing your options today, you can find a win-win scenario that protects your potential upside while managing the risk of a high tax bill or your company valuation decreasing. Whether you use a quick calculator or a full strategy platform, the most important step is to see the math before you make a commitment.
The tool shown here uses artificial intelligence and is for illustrative purposes only and not necessarily indicative of future results and there is no guarantee that similar results can be achieved. The information provided by the tool is not professional advice and is not intended by Secfi, Inc., its affiliates, and Secfi representatives, to be deemed as investment, legal, tax or other professional advice or recommendations of any kind, or to form the basis of any decision to do or to refrain from doing anything. Secfi does not review the accuracy or completeness of the information provided to us within the tool.
Sources
- https://dqydj.com/iso-calculator/
- https://www.equitylist.co/products/stocks-option-management
- https://erikbarbara.com/iso-amt-calculator/
- https://www.equitylist.co/solutions/founder
- https://releasenotes.carta.com/introducing-an-exercising-simulator-for-option-holders-13OsNO
- https://carta.com/
- https://carta.com/equity-management/
- https://www.irs.gov/taxtopics/tc427