You're leaving your company — should you take the exercise deadline extension?

When leaving a startup that awarded you ISOs, it used to be that you were pretty much screwed.

Your incentive stock options (ISOs) would expire within three months (due to their so-called 90-day post-termination exercise window), so you had to either buy the shares before the exercise deadline – often triggering a hefty tax bill – or let go of your hard-earned employee equity.

Luckily, more and more startups are now willing to extend exercise deadlines by 5 or more years. Examples:

• Mixpanel: 5 years
• Coinbase: 7 years
• Quora: 10 years

There's one caveat. If you take the extension, your ISOs convert to non-qualified stock options (NSOs).

So – should you do it?

TL;DR

If you're optimistic about the company, it's probably better to exercise your ISOs now rather than converting to NSOs.

The reason? If there's a successful IPO (and you meet certain requirements – see below), you save on taxes, so you'll take home more.

Of course exercising isn't free, so this only works if the costs aren't too high – or if you are eligible for exercise financing at good enough rates (so you're still at a net benefit with the tax savings, despite the financing fees). Otherwise, take the NSO conversion.

The long answer:

If you don't want to lose your equity, you have 3 options

Each with their pros and cons.

A. Exercise your ISOs, pay for it with your own money

👍 Reduced IPO tax (you'll earn more in a successful IPO)

🚫 You pay exercise costs, including taxes

🚫 You risk losing money (if no/mediocre IPO)

B. Exercise your ISOs, pay for it with exercise financing

👍 Doesn't cost you anything

👍 No risk of losing money (if unsuccessful IPO)

👍 Reduced IPO tax (you'll earn more in a successful IPO)

🚫 However, (a part of) your tax savings goes to financing fees

C. Convert to NSOs, don't exercise

👍 Doesn't cost you anything

👍 No risk of losing money (if unsuccessful IPO)

🚫 High IPO tax, so you'll earn less in the IPO

Note that with a "successful IPO" I mean one where the exit value of your company is high enough, so you can sell your shares at a gain.

Which of these three options is the best?

You can make the highest amount of money with Option A

...if you can afford it.

By exercising your ISOs, the gains you make in the IPO can get taxed as long-term capital gains. That's a substantially lower tax rate. The difference can be lucrative – see this Snowflake case study (tax savings: $135,000).

You'll get long-term capital gains if you check two boxes:

• You sell your shares at least 12 months after exercising your ISOs
• You sell your shares at least 24 months after the ISOs were granted to you

Of course Option A is only an option if you can afford the costs to exercise, including the tax bill you'd trigger. (You can use this online calculator to see what your costs would be.)

Also, going this route means putting your money at risk. If your company doesn't manage to have a successful exit, it's gone.

Otherwise, whether Option B is best for you depends on 2 things

Optimistic about an IPO, but option A not possible?

Then Option B is best for you if:

• Exercise financing is available to you
• You can get it at good enough rates

Both depend on the company you work(ed) for.

If your company isn't eligible for exercise financing, Option B is also not an option and you should go with Option C: convert to NSOs.

But if you can get exercise financing at good enough rates, you're better off with Option B in case of a successful enough exit. Even though you'll owe fees, you'll be at a net benefit versus Option C due to the reduced IPO tax.

So, in summary. Assuming good financing rates and assuming a successful exit, your best option is A, then B, then C. For Option A you'll have to come out of pocket, while B and C won't cost you anything.

How to decide? Use this flowchart

Step by step:

• Use this online calculator to check what your exercise costs would be (including taxes)
• Exercising affordable? Confident the company will go on to have a successful exit? OK with the risk that you might lose your money? Go with Option A: exercise your ISOs, paying for it yourself
• Exercising too expensive? Check if exercise financing is available to you, and at what rates.
• Exercise financing available at good rates? Expect to check the boxes for long-term capital gains? Go with Option B: exercise your ISOs using exercise financing
• No exercise financing available? Go with Option C: take the deadline extension and convert your ISOs to NSOs

If you need a sparring partner, happy to help out. Just hit me up for a quick chat ↘️

How to quickly check the rates at which you can get exercise financing

If you're considering Option B:

• Create a Secfi account and enter your equity details (takes 3 minutes)
• Once logged in, request a financing proposal (takes 1 minute)
• If eligible, we'll send you a detailed proposal catered to your situation

You'll get a personalized chart that models out your specific scenario and shows your benefits under options A, B and C.

We'll also invite you for a quick "we answer all your questions" call, where we can discuss anything. Feel free to ask about rates, stock options, taxes, ISOs vs NSOs, how IPOs work...

For a lot of companies (e.g. Coinbase, Procore, Gitlab, Segment) we already have rates because we've worked with employees before. If you're at one of those, the process is fast-tracked and you'll have the proposal in just a few days.

On the fence between Option A and Option B?

If you want to exercise your ISOs but are not totally comfortable covering the costs with your own savings, it's perfectly possible to exercise up to a certain amount at your own cost, then use exercise financing for the remainder only. That way the fees will be a bit lower, and you'll have the best of both worlds.

You can decide up to what amount you're comfortable putting in. Just let us know, and we'll include that scenario in the financing proposal.

Converting to NSOs? Two additional things to consider

1. If you take NSOs and don't exercise right now, but later decide you still want to exercise after all, it's probably more expensive

The tax bill from exercising will be higher for two reasons:

• NSOs have a less favourable tax treatment than ISOs
• If the company continues to grow, its 409A valuation (also known as fair market value) will continue to rise

If you want to see the impact of ISOs vs NSOs as well as higher 409A valuations, use our free Stock Option Tax Calculator. If you add your stock options twice – once as NSOs, once as ISOs – you can toggle both and see the difference.

2. An extended deadline is great, but still no guarantee your company will in fact exit within that deadline

If it doesn't, you'll still lose your equity when the deadline expires. That's not a risk if you exercise your stock options instead. Good to consider especially in case of a 5-year extension.