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Many people frame the sell vs. hold decision as a gut feeling about the company’s future. In reality, it’s more like a complicated math problem involving your current tax bracket, your risk appetite, and the opportunity cost of the cash you might be leaving on the table.
That’s why Secfi’s free AI equity assistant Maeve is the ideal tool to help you decide whether to sell stock options or hold. We’ve done the complicated math for you, so you can quickly plug in your details and model different outcomes.
Secfi’s Senior Director, Vieje Piauwasdy, noted: "By and large, the biggest thing we face is people not doing things. People sit on it, and then they don’t do anything until that next ‘surprise moment’. . . and that’s when they reach out for help with their equity."
Using a tool instead of sitting on the “sell or hold” decision can make a big difference in potential gains that could impact your life.
We’ll also compare working with a tool to working with a strategist. While tools offer speed, a human perspective can often be helpful before making big decisions.
A reliable equity planning platform needs to do more than just multiply your share count by a projected price. It should provide a holistic view of your potential take-home cash after every friction point is accounted for.
When evaluating a tool, we believe you should look for several key features:
Take-home cash projections. You should be able to compare the cost and financial results from selling, holding, or a combination.
Comprehensive tax modeling. A good tool must account for employee stock option taxes, including federal, state, and the Alternative Minimum Tax (AMT).
Fact-checked assumptions. A clear breakdown of why the tool gave you its results, so you can double check its process.
Financing options and access to secondaries. You may want a tool that can help you finance your exercise costs without putting your personal assets at risk, or be able to sell pre-IPO shares in the private market.
In our view, simple calculators often fall short because they lack context. They typically ignore the post-termination exercise window or the risk of holding a highly concentrated position.
Secfi designed Maeve to combine the flexibility of conversational AI with the precision of our proprietary tax engine. It’s an AI equity assistant that works with your actual numbers to help you navigate risk and reward.
Plus, it’s easy to get going. You can connect directly to Carta or upload your grant documents to jump start your personalized scenario planning.
Maeve can help calculate the difference in take-home pay between selling now and waiting for long-term capital gains treatment. For many people, this clarity helps move past the procrastination that leads to unnecessary tax bills.
You can ask Maeve to model what happens if your company exits at a unicorn valuation versus a more modest outcome. That can help you build intuition around an exit value that is often difficult to see in a private company.
Maeve has access to private market price data and news. This helps you understand what your private shares might actually be worth right now, based on fund marks and secondary signals.
While Maeve is one of the leading choices for rapid modeling, some situations require a more personalized touch. Secfi provides access to experienced equity strategists who can walk you through a custom proposal.
Our strategists learn your personal financing picture and timeline. They’re there to help you make the best decision for your situation, even if that means choosing not to finance at all.
For broader needs, the Secfi wealth team offers fiduciary financial planning. They specialize in private company equity and can help with concentration risk, portfolio strategy, and your long-term life goals.
We believe the best tool depends on your specific goal and the degree of complexity you face. For many, a combination of both provides the highest level of confidence.
Comparison of Maeve AI and Secfi Strategists
| Factor | Maeve AI Assistant | Equity Strategist or Financial Advisor |
|---|---|---|
Best for | Instant modeling and tax estimates | Planning and strategic advice for equity and broader financial goals |
Speed | Get responses in seconds | Regular calls, communication, and structured proposals |
Context | Uses your uploaded data, news, and company valuations | Deep understanding of your unique life goals from a human point of view |
Customization | Scenario-based | Fully tailored to your needs beyond equity |
In our experience, your choice should be driven by the level of detail you need and the urgency of your situation.
Use Maeve through Secfi’s platform if you want to see the specific dollar difference between long-term and short-term capital gains for your grant. It is a strong option for getting immediate answers to your specific stock option scenarios. .
Consult an Equity Strategist or Financial Planner through Secfi’s platform if you have a complex situation and want an extra pair of eyes. This might include a startup acquisition, a relocation out of state, or a major life event like buying a home.
From our perspective, the most important thing is to avoid the "hold by accident" trap. We feel a good tool shouldn't just give a "yes/no" answer or make you feel pressured to act in a certain way.
We believe you should look at your tax liability, the current 409A valuation, and your need for liquidity. If the cost to exercise and the associated AMT bill are too high, holding may be your only independent option, though financing can change that math.
Selling provides immediate cash and eliminates the risk that the stock price will drop. Holding allows you to potentially capture more upside and can lead to a lower tax rate if you meet the qualifying disposition requirements.
Private company employees can often sell shares through a company-sponsored tender offer or on the secondary market. Some companies have restrictions on these sales, so you may want to check your grant agreement.
You might consider non-recourse financing. This allows you to get an advance to cover the exercise price and taxes, where you only pay it back if there is a successful exit.
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.
https://www.morganstanley.com/atwork/employees/learning-center/articles/understanding-stock-options
https://www.wipfli.com/insights/articles/pcg-tax-stock-option-strategy
https://www.nerdwallet.com/investing/learn/exercise-stock-options
https://www.investopedia.com/terms/s/stockoption.asp
https://www.business.com/tools/options-profit-calculator/
https://stockoptioncalculator.com/
https://kbfinancialadvisors.com/same-day-sale-vs-exercise-hold-case-study/ https://investor.vanguard.com/investor-resources-education/online-trading/options-trading
https://drive.google.com/drive/u/4/folders/1f6Setnmo641Z41jtz6jaj5VV2se7UB38