How Startup Founder Stock Often Triggers Unnecessary Personal Tax Hits (2024)

“It's a secret, but no secret

It's a rule, but no rule”

Cooksferry Queen” by Richard Thompson

It feels like once or twice a day I speak with a startup that has tripped over a seemingly invisible rule applicable to founder equity: the founders and early employees/advisors in startups really need to get their stock or options BEFORE there’s a term sheet for a venture or angel funding.While not a secret, the law doesn’t come right out and expressly say this. Frankly, to know this you’d have to talk to folks who have an understanding of tax law, corporate law and startup life.That understanding, unfortunately, is in shorter supply than it should be and, for founders, seems to largely have been learned the Sharon Jones & the Dap Kings way:

“I learned the hard way, baby. Now I know about you. I learned the hard way … Not to be your fool.” I wonder whether Sharon was singing about Section 409A?

In an effort to save folks both cash and heartache, and to save other folks (especially me) the time involved in having to explain this (I currently explain this to founders multiple times each week), I’ve laid out below some background on the rule, an explanation of how and why founders most commonly miss this, and finally, how to avoid learning it the hard way (thanks Sharon…love your tunes!).Let’s start by explaining the problems pertaining to stock options and then discuss founder stock.

Background on Section 409A

In 2004, the IRS announced that it was going to change the way stock options worked for startups. Okay, it didn’t actually say “for startups,” but that’s our focus in reviewing Section 409A of the Internal Revenue Code, a rule which phased in over the following few years and was a backlash against the abuses of Enron, Worldcom and the executives who took cash off the table ahead of investors who were left with worthless Enron and Worldcom stock.

Why 409A Matters for Startups

The rule applies to deferred compensation. Have your eyes already glazed over? Mine have! But stay with me because we’re talking about stock options, the key currency for startup talent recruiting and retention.The rule, in oversimplified and practical terms, says that you can’t grant stock options at an exercise price below the then-current fair market value of the stock you’d get for exercising that option.

So how does this translate into giving stock before your startup gets a term sheet? Glad you asked!

The IRS gave guidance urging startups to obtain an independent written valuation using accepted methodology done by someone skilled in the field of valuing companies.This spawned a cottage industry of 409A valuation firms. Here’s where it gets complicated.The IRS wanted to help all of us by offering some degree of clarity and ‘protection,’ which I’d describe as complex and a bit fuzzy. The ‘protection’ in this instance, means that if you do what the IRS prescribes, the IRS will give you the benefit of a “rebuttable presumption” that you didn’t screw things up.A “rebuttable presumption” is NOT a “safe harbor;” rather it’s just a presumption that the IRS can overcome by showing that the valuation method or its application was “grossly unreasonable,” whatever that means. We have to take what we can get because the presumption is all the IRS was willing to give us!

While the IRS also allows a rebuttable presumption for valuations performed by someone affiliated with the startup, it also suggests that the affiliated valuation person should have logged at least five years of valuation-focused experience (business valuation, accounting, investment banking, private equity), but even then, a “good faith” effort isn’t sufficient, so we’re not surprised that most startups we see do use an independent valuation firm.

Oh Joy, a Rebuttable Presumption! Gee Thanks!

Here’s how you typically can avail yourself of Section 409A’s rebuttable presumption: The startup’s board of directors has to review the valuation report and it really should deliberate about it (does the report make sense, are the facts correct, does it definitely mention the recent transactions in the company’s stock, is the number of shares outstanding correct, are there other errors in it?). Once the board is comfortable with the report’s factual and mathematical accuracy, the board must ask some additional questions. First, the board must ask whether the valuation report is fresh? There are two dates on these 409A valuation reports, the “as of” date (typically the end of a period, like 12/31 or a month end, because valuation firms likes to rely on financial statements dated at the as of date). The second date is the issue date of the report (when the valuation firm completes the work).These reports become stale after a year and sometimes a report can go stale even sooner (growth companies generally get new valuations more than just annually). Specifically, the presumption applies to an independent appraisal that meets the necessary requirements “as of a date that is no more than 12 months before the relevant transaction to which the valuation is applied (for example, the date of grant of a stock option).” If it goes stale, the board can’t rely on it so, paraphrasing Seinfeld’s Soup man, “no presumption for you!”

Next, the board has to consider whether there’s been what I will call a “supervening valuation event,” since a report can go stale if it “fails to reflect information available after the date of the valuation that may materially affect the value of the corporation.” What does that mean, and how does it affect the presumption? Nobody’s entirely sure, but the startup and venture community has reached consensus that one thing that generally qualifies as a “supervening valuation event” is a written term sheet to fund or acquire the company from a realistic purchaser who has actually done some diligence on the startup before issuing the term sheet. So if you get a term sheet that’s for real (we can discuss when a term sheet isn’t for real!), that probably makes the valuation stale, especially if the startup later completes that deal. How much diligence? What’s a realistic purchaser? How much money has to be involved? What if you think the term sheet is entirely inaccurate? The answers to these questions will require some fact-sensitive judgment.

Having gotten some comfort that the report seems accurate and isn’t stale, the board next adopts board resolutions finding that the report’s valuation of a single share of the startup’s common stock accurately reflects the current fair market value of that share. In that same meeting, the board then grants options on common stock with an exercise price per share of not less than the valuation price. Of course, stock option grants are only valid if they contain the number of shares, the strike (or exercise) price per share, the vesting schedule, and the recipient. So all of that should be laid out in the resolutions too. We almost always see that in an exhibit or schedule to the resolutions.

Supervening Valuation Events Also Affect Outright Equity Grants

Section 409A doesn’t specifically apply to giving someone stock, whether outright or subject to risk of forfeiture (vesting). However, and we think this is a pretty big “however”, it would be pretty awkward to grant stock options based on a fresh 409A valuation report that the board has adopted and then give someone shares of stock at a much lower valuation at about the same time. That would mean that the board, acting on behalf of the company, would be taking inconsistent tax positions regarding value of a single share of the company’s common stock. Let’s avoid doing that! I know that “consistency is the hobgoblin of little minds” but this is the IRS we’re talking about! (To the IRS team members reading this: I meant that lovingly, seriously, no disrespect intended!). Also, I’m pretty sure that the Ralph Waldo Emerson “hobgoblins” quote speaks about “foolish consistencies” and to me, it doesn’t seem foolish to say that if a single share of common stock in a privately held startup was worth one thing on Tuesday then absent a “supervening valuation event” it should be worth the same thing on Thursday (see IRS, I really am on your side on this one!).

Founder Stock

So why does this mean founders must receive their stock before the term sheet hits? Well, I needed to build some foundation because this stuff is complex. Let’s say you incorporate the startup on December 2 (most venture capital-backed startups are Delaware C corporations) and there are three founders who toil tirelessly for four months. On April 2, they receive a term sheet stating that a good venture fund will lead a seed round totaling $1 million in a deal that values the startup at $5 million on a pre-money basis. Pre-money valuation simply means that the deal values all the outstanding stock before the investment at $5 million and, when you include the shares the startup will issue for the fund’s $1 million, the startup would be valued at $6 million on a “post-money” basis.

If the founders had documented the issuance of the shares on (or just after) December 2, using a valuation much lower than the April 2 valuation, all is probably well. The IRS is likely to respect the startup’s position that the founders’ hard work has enabled the startup’s value to climb appreciably over the span of four months. But what if the founders had neglected to paper the stock issuance and now have to do that before the deal closes? The IRS might conclude that the reason each founder is receiving her shares is because she either paid for them or worked for them. In most cases, the founders have paid very little cash for their shares and, instead, have mostly worked to earn those shares (equity paid for with hard work rather than cash is often called sweat equity).

Tax on Sweat Equity

How does the IRS treat payment (whether in shares, cash or chocolate) made for a person’s work effort? Well, the IRS treats that as ordinary income and taxes the employee based on when she receives payment (in this case, in shares). Remember that pre-money value of $5 million? The investors are buying preferred stock so their shares are probably worth more than the common shares, but in this case, the common shares are still worth a ton of money. Might those shares of common be worth well over $1 million? Indeed they may well be. Let’s assume – just for our hypothetical – that the common shares held by the founders are worth, in aggregate, $1 million and let’s split that evenly in three ways among all the founders. Now let’s say each founder has used her own cash to fund the company but that in aggregate only totals $10,000. The IRS could conclude that each founder paid $3,333 in cash and is getting roughly $333,333 worth of stock so she has $330,000 of income, and the startup has to withhold income and payroll taxes. In this situation, the founder will be looking at a tax hit of roughly $130,000 (it could be more but that assumes a 40% tax rate on a state and federal level). Had the founders only papered the stock issuance at the beginning (when they incorporated), they likely would not have ANY tax hit at the time of the term sheet.

Promised Equity

Of course, in the situations we typically confront, the founders have also promised equity to at least one employee and one contractor/advisor. (I’ve separately written about the business rationale for stock option vesting for employees and advisors). Those people could have obtained really inexpensive stock options that would now be pretty valuable. But in our hypothetical, the founders haven’t had their lawyer “write anything up” yet because they only called or hired a lawyer when the term sheet arrived. They’re now likely in a “blackout” period for option grants. In other words, it’s too risky to grant options at a low valuation now, because the fair market value of a single share of the startup’s common stock is about to change…dramatically. The startup is right in the middle of a “supervening valuation event” and will likely want to wait until the deal is closed to obtain a valuation report that comports with Section 409A and then issue options at the strike price derived by referencing that report.

The founders would have been better off papering their equity back in December when they formed the corporation and the employee and contractor would have been smart to have insisted on getting their options papered when they started providing services to the startup, rather than waiting for a few months. It’s totally fine for the startup to ask the contractor and employee to wait for the next regularly scheduled board meeting, but the founders shouldn’t be surprised if the employee and contractor express some unhappiness if the price has increased materially because the next board meeting occurs months later.

Fixing a Hole

There may be some ways out of this hole, depending on the facts of your specific situation but the best way out of the hole is to do the paperwork in real time as the situation is unfolding. Otherwise, you’re right back in Sharon Jones’ school where founders learn things the hard way!

How Startup Founder Stock Often Triggers Unnecessary Personal Tax Hits (2024)

FAQs

What are the tax implications of founder stock? ›

When you sell your founders shares, you'll usually have to pay both federal and state taxes on that income. Most states, including California, don't treat investment income differently than they treat income from a normal salary.

What do startup founders struggle with? ›

Startup founders are no strangers to long hours and unrelenting workloads. With limited resources and a constant need to prioritize, there is always more to be done than time allows. The pressure to deliver results can lead to burnout, as founders struggle to maintain a balance between work and personal life.

Does QSBS apply to founders? ›

Qualified small business stock (QSBS) is a type of share issued by a C corporation (C corp) that meets requirements in the Internal Revenue Code, specifically Sections 1202 and 1045. QSBS offers substantial tax benefits to shareholders, most notably founders and early investors.

What happens when founder sells his shares? ›

Under a typical vesting schedule, the stock vests in monthly or quarterly increments over four years; if the Founder leaves the company before the stock is fully vested, the company has the right to buy back the unvested shares at the lower of cost or the then fair market value.

How do billionaires not pay taxes with stocks? ›

Billionaires (usually) don't sell valuable stock. So how do they afford the daily expenses of life, whether it's a new pleasure boat or a social media company? They borrow against their stock. This revolving door of credit allows them to buy what they want without incurring a capital gains tax.

What is the difference between common stock and founders stock? ›

Founders stock refers to the equity that is given to the early founders of an organization. This type of stock differs in a few important ways from common stock sold in the secondary market. Key differences are (1) that founders stock can only be issued at face value, and (2) it comes with a vesting schedule.

What are 4 mistakes startups typically make? ›

Here are the top ten most common startup mistakes – and how to avoid them.
  • Spending money on the wrong things. ...
  • Rushing through the hiring and onboarding process. ...
  • Operating without a style guide or brand persona. ...
  • Being afraid to test and learn. ...
  • Partnering with the wrong investors.
Jun 19, 2023

What is the average age of successful startup founders? ›

The study reveals that the average age of successful startup founders is between 35-45.

What is the #1 reason why startups fail? ›

1. Lack of product-market fit (PMF) 42% of startups fail because they lack product-market fit — their offering simply doesn't solve a real problem that enough people are willing to pay for.

What is the 80% rule for QSBS? ›

The stock must be purchased with cash, property, or as payment for a service. The stock must be held for at least five years. At least 80% of the issuing corporation's assets must be used in the operations of one or more of its qualified trades or businesses.

What states don't recognize QSBS? ›

States that do not conform to Federal QSBS (IRC Section 1202)
  • Alabama.
  • California.
  • Mississippi.
  • New Jersey.
  • Pennsylvania.
  • Puerto Rico.

What is the 10 million limit for QSBS? ›

QSBS protects up to 10x their investment from long-term capital gains taxes, or $10 million, whichever is greater. For example, an investor who put in $10 million could avoid paying federal capital gains tax on up to $100 million.

How are founder shares taxed? ›

Founders of a start-up usually take common stock as a large portion of their compensation for current and future labor efforts. By electing to pay a nominal amount of ordinary income tax on the speculative value of the stock when it is received, founders pay tax on any appreciation at the long-term capital gains rate.

How much stock should a founder get? ›

Investors own 20-30% of startup shares, while the founders and co-founders should have more than 60%. You can also leave around 5% of available shares but allocate 10% to employees.

Do founder shares get diluted? ›

This research shows an average of about 28% founder dilution — almost 30% — from Seed round to Series A. Founder dilution from Series A to Series B is about 11%. By Series B, on average founders own less than 30% of the business while investors own more than 55%.

What are the advantages of founders shares? ›

Founder's stocks offer early, low-cost equity to founders, granting substantial control and ownership. While these stocks dilute as funding increases, they come with voting rights and vesting schedules, aligning founders' long-term interests with the company's growth and marking key milestones in its journey.

How are startup shares taxed? ›

The tax rate depends on your holding period. If you held the investment for more than one year, it's considered a long-term capital gain, which generally has a lower tax rate. If you held it for less than a year, it's a short-term capital gain, taxed at your ordinary income tax rate.

What percentage of shares should a founder have? ›

The short answer to "how much equity should a founder keep" is founders should keep at least 50% equity in a startup for as long as possible, while investors get between 20 and 30%. There should also be a 10 to 20% portion set aside for employee stock options and, in some cases, about 5% left in a reserve pool.

How do founder shares work? ›

Founder's shares represent a form of ownership granted to the founders (and often initial employees) of a startup. They provide unique rights and privileges, allowing founders to participate in crucial decisions regarding the company's leadership, strategic direction, and operational matters.

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