When LLCs Make Sense for Startups

TL;DR Nutshell: In the vast majority of instances, tech startups are best served by starting out as Corporations (C or S-corps, but usually C-Corps) on Day 1, and lawyers suggesting otherwise are usually generalists who lack tech/vc-specific domain expertise to understand why. However, there is a narrow set of circumstances in which LLCs make sense for a startup.

Background Reading:

This post is about the “almost” part of that tweet. But to get there, it’s important to address the “simpler” and “tax efficient” aspects, because those are the two core reasons that I often hear pushed onto founders for why they should be LLCs.

LLCs may be simpler generally, but Tech Startup LLCs with investor capital and equity compensation never are.

Here’s a hypothetical: Imagine you’re an athlete who’s signed up for a football camp held in Boston in the middle of February. Your general knowledge of Boston weather tells you that it is going to be a** cold. You ask a few other people with knowledge of Boston, including me (I went to law school there), and receive confirmation that Boston is a** cold in February. So you show up to the camp with only your winter gear… but it turns out the camp is entirely indoors in a heated facility. Whoops. Should’ve asked someone with true domain-specific knowledge of that camp, not just people with general knowledge. 

That, in a nutshell, is what happens when lawyers and other business people tell tech founders to use LLCs. LLCs are extremely common in the general legal world. For simple operations with one or a small number of owners, they are by far the dominant legal structure, because they usually are simpler. However, for tech startups, who very often (i) use equity as a significant part of their compensation for employees/service providers, and (ii) often raise capital with multiple equity classes, complex preferences/rights, etc., things get extremely complex under an LLC structure, much more so than with corporations. The amount of tax and legal analysis that has to be done to issue equity compensation and/or raise capital in an LLC is (without exaggerating) 10x that of a corporation.

So, if your plan is to raise capital and use equity as a form of compensation for employees and contractors (which is usually a hallmark of a tech startup), do not delude yourself for a second that an LLC will be simpler than a corporation. 

The “Double Tax” issue usually only matters if your startup is a “cash cow.”

Yes, in a general sense LLCs have one layer of tax and C-corps have two. That is another reason why (as stated above), LLCs have become a very dominant legal structure, not just for simple companies but also for many large businesses as well. Again, though, context is key. The “additional layer” of tax that corporations face is on net profits; after accounting for expenses, including salaries. No net profits, no corporate tax. So if a startup is going to be generating substantial profits (taxed once) with the end-goal of distributing those profits to shareholders (taxed again at individual level) as a dividend, the two layers are a problem.

But how many high-growth tech startups do you know that, instead of reinvesting profits for growth, pay profits out as dividends? Not many; certainly not in the first 5-10 years of the company’s life. Most high-growth tech startups deliberately operate at a net loss for a very long period of time, and therefore (i) aren’t worrying about taxes on net profits, and also (ii) are taking advantage of those losses at the corporate level in a way that may not be even use-able on the individual level. This, btw, is also why S-corps are usually not very helpful for tech startups either.

And to add an additional wrinkle: in an acquisition, corporations often have the ability to do tax-deferred stock swaps, whereas LLCs don’t. So, in short, the “LLCs save a lot of taxes” perspective, while generally correct, is usually misapplied to tech startups by people who simply don’t do enough startup/vc work to give sound advice. Yes, VCs often push companies to be C-Corps (read the background articles), but VCs are hardly the only reason why the C-Corp structure is used in tech. 

LLCs therefore make sense for tech startups that:
(i)
expect substantial net profits very early on;
(ii) aren’t planning on raising institutional venture capital, and/or
(iii) aren’t planning on using equity to compensate a lot of people.

Lots of net profits early on (rare)? The single layer of tax may be worth it, and even institutional VCs sometimes are willing to accept the complexity of an LLC to take advantage of the tax savings.  Not planning on raising VC money any time soon? Other types of non-tech investors are usually more comfortable with LLCs than VCs are. Not planning on paying your employees with equity? Then you’ll avoid the tax nightmare of issuing LLC equity to dozens/hundreds of people.

Few tech startups fit the above scenario, and that’s why few are LLCs. The classic tech startups that operate (rationally) as LLCs are bootstrapped/self-funded software and app companies with no plans to scale very quickly with outside capital, and large “marketplace” startups for which the actual investment in the technology is minimal relative to the large amount of revenue/profit pushed through the marketplace. For almost everyone else, C-corps are king, and for good reason.

p.s. I am not your tax lawyer, and am not pretending to know the right answer for your specific company. The above is just general knowledge; not legal advice. If you rely exclusively on a blog post to determine your legal structure, without talking to a professional to understand your context, you’ve taken on the risk of screwing it up.

Early Hires: Options or Stock?

Nutshell:  While the conventional equity path of a startup is to issue (i) common stock to founders and (ii) options to employees, early hires concerned about taxes will often insist on receiving stock as well. Voting power, along with other political factors, present a few tradeoffs for founders to consider in that scenario.

Vocabulary:

  • Option Pool” – a portion of the company’s capitalization set aside (after founder stock is issued) for equity issuances to employees, consultants, advisors, etc., and subject to a special “plan” designed to comply with complex tax rules.  Even though it’s referred to as an “option” pool, properly designed equity plans will allow for direct stock issuances under the pool as well; not just options.
  • ISO – Incentive Stock Option – a tax-favored type of option issuable only to employees, if certain requirements are met. The main benefit is that upon exercise, the difference between the exercise price and the fair market value on the stock at the time of exercise is not taxed as ordinary income. However, it is subject to the Alternative Minimum Tax (AMT), which can hit certain people depending on their tax situation.
  • Restricted Stock” – For purposes of a private startup, just another way of saying Common Stock. The same security that founders get, except for non-founder employees it’s usually issued from the “pool” (under the Plan) using different form documents.
  • Early Exercise Options” – Conventional options issued to employees are not exercisable until they vest; meaning until the recipient has worked long enough to “earn” the right to exercise them.  Early exercise options have modified vesting/exercise provisions so that they can be exercised from Day 1 – with the underlying shares becoming subject to the vesting schedule.  From the Company’s perspective, early exercise options are very similar to restricted stock issuances. The only real difference is that the recipient has the option to exercise and receive the Stock on Day 1, or sit on it and exercise later.

Convention.

The conventional path of a Company’s equity issuances goes something like this:

  • Founders receive direct issuances of Common Stock (not options)
  • Non-Founder employees receive ISOs (options)
  • Consultants, advisors, etc. receive NSOs (options)
  • Investors receive Preferred Stock, or SAFEs/Convertible Notes that convert into Preferred Stock

Backround:  

  •  The value of restricted stock is taxable as ordinary income on the date of issuance, unless its fair market value (FMV) is paid in cash.
  • Options, both ISOs and NSOs, however, are generally not taxable on the date of grant, as long as their exercise price is equal to the FMV.
  • So, you would normally expect employees to prefer receiving options over stock. No tax > Tax. And this is the case when the stock’s FMV is relatively high. That’s why later hires (usually after a Series A) almost always receive options, without question.
  • Stock gets to vote on stockholder approvals. Options do not (until they’re exercised for stock).

The Issues: Early employees want to minimize tax. Companies want to avoid giving away voting rights/complicating stockholder votes too early.

  • However, in the very early days of a startup’s life, avoiding tax on restricted stock is easy because of how low the FMV of the stock is (fractions of a penny): write a check for a few dollars (the full FMV), or just pay the tax on the few dollars of ordinary income.  You therefore get the “no tax on grant” benefit of options, without worrying about paying tax later on an exercise date.  Receiving stock also gets the clock running on long-term capital gains treatment.
  • Therefore, very early hires, when they do their homework, tend to insist on receiving restricted stock (or early exercise options) over conventional options. Better to deal with tax when the stock is worth (at least to the IRS) virtually nothing, instead of years later upon exercising the option when the tax bill could be much greater (ordinary income for NSOs, or AMT (for some people) for ISOs).
    • Sidenote: Conventional equity plans also have a 90-day post-termination exercise period, meaning, when an employees leaves a company (voluntarily or involuntarily) they have to exercise their options within 90 days, or they then get terminated – even if vested. Paying the exercise price isn’t an issue for an early hire in that scenario, because it’s very low (the fractions of a penny FMV), but if the AMT comes into play it can hit them with a tax bill.  This doesn’t come up in a Restricted Stock scenario.
  • The tradeoff from the Company’s perspective is that, just like founders, those hires that receive restricted stock will have full voting rights (including seeing whatever is submitted for stockholder votes) for all of their stock on Day 1, before they’ve vested in anything.  When only one or two people are in question, this may not be a big deal. It can be a way of making early employees feel like a part of the core team, because their equity is being treated just like founders.  When there are more than a handful of hires, however, it can get unwieldy fast. The number of people to consult for stockholder votes can go from 2-3 to 10, 15, 20. If there are consultants and advisors in the picture, they may start to ask why they aren’t getting the same tax benefits as early hires. And then at some point you have to draw a line and start granting options. Is the first optionee not as special as the restricted stock people? Politics. 

Generally speaking, the decision to give restricted stock v. options to very early hires is a practical/political one.  While the tax-favored nature of ISOs means that most early employees won’t see much of a tax difference between receiving ISOs v. restricted stock, the prospect of an AMT hit in the ISO scenario does make restricted stock, on net, better for recipients.  That needs to be balanced, on the company’s side, against the early voting power/information rights given away when an employee receives stock instead of options, and how it will play out with all of the company’s other hires.  

My general advice to founders is to be aware of the tradeoffs, and to consciously treat the early voting power and tax benefits associated with restricted stock as currency not to be wasted.  If there’s a very early superstar that you deliberately want to single out as a key player, use the currency.  If not, then make the decision based on all the other factors. Company culture will likely factor greatly into the calculus.  Many, many founders prefer to avoid the politics/complications and simply draw a line at the founder (stock)/non-founder (option) division.  Others are more selective. There’s no magic formula.

A few separate issues worth addressing:

  • The 90-day post-termination exercise period (after which unexercised options, vested or not, are terminated) often gets criticized as being unfair to employees, and there’s some justification for that criticism. The view is that the employee shouldn’t be forced to “use it or lose it” if they did their time (their option vested) and are now moving on to a new company.
    • The actual 90-day number comes from tax rules requiring that ISOs be exercisable only within 90 days of termination.  If an option is exercisable after that, it automatically becomes an NSO for tax purposes. But there’s nothing in the tax rules requiring that the option be terminated at 90 days. That’s largely meant (i) as a deterrent (frankly) to people quitting, and (ii) a way to clean up the cap table for people who didn’t want to pay their exercise price, allowing that portion of the pool to then be re-used for new hires.
    • While the 90-day period is still convention, key executives/hires will often either negotiate for an extended exercise period for their own grants, or the Company will as a gesture of good will, decide on its own to selectively extend the period when someone leaves on good terms.

Obligatory Disclaimer: This post contains a lot of fundamentals and generalizations on tax rules, but it’s obviously not intended to be an exhaustive statement of those rules. Circumstances vary, and you should absolutely not rely on this post without consulting your own attorney and/or tax advisors.  If you do, don’t blame me when it blows up in your face.  You’ve been warned.

Reserve an Option Pool; Not an Ocean.

TL;DR  The larger the pool reserved at formation, the more dilution founders are shouldering that would otherwise be shared with employees and investors. Take it seriously.

Here’s how much discussion usually goes into determining a startup’s option pool size at formation:

Attorney: What size of an option pool do you want to reserve?

Founder: I don’t know, what’s the usual size?

Attorney: 20%

Founder: Ok, let’s go with that.

The reason so little thought goes into it is partially due to the fact that startup formations have (for good reason) become very standardized.  Neither founders nor attorneys are interested in delving into any nuances beyond the core questions about equity distribution and founder dynamics.  The founders want to focus on their product.  The lawyers don’t want to burn time on a fixed-fee transaction.

But here’s why failing to take the time to think through your initial option pool size is a problem: reserving too large of a pool, even if it’s never used, means you’re giving away a larger amount of the company to future hires/investors than you want to.

“That can’t be!”, the founder says. How can an unused pool impact my dilution? Whatever doesn’t get used just gets canceled at an exit, right?  While technically correct, this misses a very important issue: future employees and investors will rely on the term “fully diluted capitalization” in determining how much of the Company they want to ask for in the hiring or investment process. And “fully diluted capitalization” includes the unused part of the option pool.

The Hiring Example

You’re negotiating a compensation package for a rockstar developer, and they say they want 5% “of the Company.” What does that mean? The vast majority of the time it means 5% of the “fully diluted capitalization,” which means all outstanding equity AND all reserved but unused equity in the option pool.

Think this through a bit.  5% means having to give them more shares if your option pool size is 20% instead of 10% (because the pie is larger), even if none of the pool is in use.  If you end up getting a good exit in a year without having used much of the pool, the unused pool will get canceled, but the “5%” shares the developer received won’t be reduced proportionately.  The pie shrinks, but his slice stays the same size – which means yours shrinks.  The 5% hire ends up with a much higher percentage of the cap table.

Nutshell: The larger pool you reserve, even if none of it is in use, the more shares you’ll have to give to early hires to get them to a % they feel comfortable with.  Those extra shares mean, if the pool is unused at an exit, those hires own more of the Company than the % they bargained for.

Incubators-Accelerators also base their equity requests on a “fully-diluted” basis (%-based), so by having an excessively large pool, you’re giving them too many shares.

The Investment Example

This is a bit more nuanced, and I suggest you read the excellent Venture Hacks post: The Option Pool Shuffle.

Background:

  • Convertible Notes with caps generally use “fully diluted capitalization” (remember, that includes an unused pool) in determining the conversion price. So a larger pool means the investor gets more shares to get them to the right %, producing the same issue as with employees: if the pool is unused at an exit, they end up with a larger chunk.
  • In a Term Sheet, VCs generally make you “top up” the option pool to have a certain % of availability post-closing, but they make the pre-money cap table absorb all the dilution from it.  The ask will look something like this:

the total post-Closing available option pool (excluding granted options) represents 15% of the fully diluted shares of the Company.

The Venture Hacks article gives a mathematical example, but the most important point is this: the higher % the VCs require as available (unused) post-closing option pool, the lower the price they are paying for their shares, and the more dilution the founders are absorbing.

How does this relate to the point of not going overboard in reserving your original option pool? The pool you reserve before your first VC financing will set the baseline for negotiating how much of an option pool “top up” VCs make founders absorb.  If you have a 16% available pool pre-funding, it makes it look a lot more benign for a VC to demand a 15% post-money pool than, for example, if your pre-funding pool was only 5%.  Getting from 5% pre-funding to 15% post-funding will require a very large increase in the pool size.

By having a smaller pool before your funding, it reveals a much bigger “hit” on the founders when the financing is modeled and the VCs post-funding pool “ask” is reflected.  When both the VCs and the founders see the substantial dilution resulting from the pool increase, it forces a deeper discussion about what the post-funding pool should really look like. And that’s where the Venture Hacks wisdom comes in: have a hiring plan and a solid argument for how much of a pool you really need, and make the VCs argue for theirs.

Nutshell:  By keeping your pool size small before funding, it requires a much larger pool increase to get to a VC’s desired post-funding unused pool, all of which is borne by the pre-financing cap table.  This forces a necessary discussion with the VCs about what the appropriate pool size really is, instead of just accepting whatever number they pull out of thin air.

So what is the right formation pool size?

It depends. How many founders are there? Whom are you likely to need to hire in the next 12 months? These are details to discuss with your attorney.  Whatever you do, don’t just accept 20% without thinking about it.

Conclusion

As a founder, your ownership is set at formation.  Everything afterward is dilution.  By reserving an unnecessarily large pool, you’re basically protecting future hires and investors from dilution, while absorbing it all yourself.  It’s not that hard to increase your pool size if you run out of room, and when you do so, at least everyone on the cap table will absorb the dilution with you.  By keeping your pool smaller, you’ll also make VCs think twice about casually dumping an unnecessarily large pool size on their term sheets in order to drive their share price down.