Imagine you and a group of friends start a company together. Over time, you bring in outside investors to help grow the business. These investors provide the funding you need, but in return, they get a say in how the company is run. Now, fast forward a few years. The company has grown, and a big corporation offers to buy it for a significant amount of money. Everyone is excited, but there’s a problem: one of your original co-founders doesn’t want to sell. They believe the company has more potential and want to hold out for a better deal. What happens now? This is where a drag-along agreement comes into play.

A drag-along agreement is a legal provision that allows majority shareholders to force minority shareholders to join in the sale of a company. In simpler terms, if the majority of shareholders agree to sell the company, the minority shareholders are legally obligated to go along with the decision, even if they personally disagree. This might sound harsh, but it serves an important purpose. It ensures that a small group of shareholders can not block a deal that benefits the majority and the company as a whole.

In the world of startups and venture capital, drag-along agreements are especially important. Startups often have multiple classes of shareholders, such as founders, employees with stock options, and outside investors who hold preferred stock. Each group might have different priorities. For example, founders might be emotionally attached to the company and want to keep growing it, while investors might be looking for a quick return on their investment. A drag-along agreement helps align these interests by making clear everyone is on the same page when it comes to major decisions like selling the company.

Let’s go back to our example. Suppose your company has three co-founders: you, Sarah, and Mike. You also have a venture capital firm, TechInvest, as a major investor. TechInvest owns 60% of the company, while you, Sarah, and Mike each own 10%, and the remaining 10% is split among employees. If TechInvest decides to sell the company, they can use the drag-along agreement to force you, Sarah, Mike, and the employees to agree to the sale, even if some of you would prefer not to.

Types of Drag-Along Agreements 

Drag-along agreements come in different forms, each designed to address specific situations that can arise in the life of a company. Let’s break down the two main types.

First Flavor: Preferred Investors Dragging Common Shareholders

In many startups, investors like TechInvest hold preferred stock, which often comes with special rights and privileges. One of these rights is the ability to drag along common shareholders—typically the founders and employees—when it comes to selling the company. Here’s how it works: if TechInvest, as the majority preferred shareholder, decides to sell the company, they can force you, Sarah, Mike, and the employees to agree to the sale, even if some of you would rather not.

This type of drag-along agreement is especially common in venture capital deals. It’s designed to prevent a small group of common shareholders from blocking a deal that the majority of investors believe is in the company’s best interest. For example, if TechInvest negotiates a $50 million acquisition offer, they do not want one co-founder holding out and demanding $60 million, potentially scuttling the deal. The drag-along agreement helps that everyone moves forward together.

The language in these agreements is usually straightforward. It might say something like: “If a majority of the preferred shareholders approve a sale of the Company, all holders of common stock shall be required to consent to the transaction and shall have no right to object, challenge, or otherwise impede the sale.”  This gives the preferred investors the power to make decisions without being held hostage by minority stakeholders.

Historically, this type of drag-along agreement became more common after the early 2000s dot-com bubble burst. During that time, many startups were sold for less than their investors had hoped, and founders often resisted these sales because they wouldn’t receive any proceeds after the investors’ liquidation preferences were paid out. To avoid these conflicts, investors began insisting on drag-along provisions to push they could exit their investments when needed.

Second Flavor: Dragging Along Departed Founders

The second type of drag-along agreement deals with a different but equally tricky situation: what happens when a founder leaves the company but still owns shares? Let’s say Mike, one of your co-founders, decides to leave the startup after a disagreement. He still owns 10% of the company, and now he’s no longer involved in day-to-day operations. If the company later decides to sell, Mike might refuse to agree out of spite or because he has different ideas about the company’s future. This could create a major roadblock.

To prevent this, many companies include a drag-along provision specifically for departed founders. Under this agreement, if Mike leaves the company, his shares are automatically “dragged along” with the majority in any sale or major decision. In other words, Mike no longer has the power to block a deal. Instead, his shares are voted in proportion to how the other shareholders vote. For example, if 90% of the shareholders vote in favor of a sale, Mike’s shares will be counted as 90% in favor and 10% against, even if he personally disagrees.

The language for this type of agreement might look like this: “Upon the departure of any shareholder who was an original signatory to this agreement and held common stock at the time of its execution (a ‘Departing Shareholder’), all shares held by such Departing Shareholder, including common stock or any preferred stock acquired through conversion, shall be subject to a drag-along provision whereby they shall be voted in the same proportion as the aggregate vote of all other outstanding shares in any sale, merger, or liquidation event.” This assists that a departed founder can’t hold the company hostage or disrupt important decisions.

This second flavor of drag-along agreement has become increasingly popular in recent years, especially as startups face more complex dynamics between founders and investors. It’s a way to protect the company from the potential fallout of a founder’s departure, whether it’s due to personal differences, burnout, or other reasons.

Key Considerations and Negotiations

Let’s assume your company, which you co-founded with Sarah and Mike, has grown significantly. TechInvest, the venture capital firm that owns 60% of the company, is pushing for a sale to a larger tech company. You, Sarah, and Mike each own 10%, and the remaining 10% is held by employees. As founders, you’re emotionally invested in the company and want to make sure your voices are heard.

The size of your ownership stake plays a big role in how much drag-along terms matter to you. If you’re a small shareholder—say, you own just 1% of the company—your ability to influence the outcome of a sale is very limited. In most cases, a single small shareholder will not have much leverage to block a deal, even without a drag-along agreement. However, if there are many small shareholders like you, collectively holding a significant portion of the company, your combined influence could become a problem for the majority shareholders. This is why drag-along agreements are often included in term sheets—to prevent a fragmented group of small shareholders from derailing a deal.

But ownership isn’t the only factor. Where your company is incorporated also matters. Different jurisdictions have different rules about shareholder consent. For example, in California, a sale typically requires a majority vote from each class of shareholders (common and preferred). In Delaware, which is a popular state for incorporating startups, the rules are slightly different. There, a sale usually requires a majority vote of all shares on an “as-converted” basis, meaning preferred shares are treated as if they have been converted to common stock for voting purposes.

When negotiating drag-along terms, there is often room for compromise. One common approach is to align the drag-along rights with the majority of common stockholders rather than the preferred investors. In our example, this would mean that TechInvest could only force a sale if a majority of the common shareholders (you, Sarah, Mike, and the employees) also agreed. This gives the founders and employees more control over the outcome, while still making clear that the company can move forward if there is broad consensus.

Another strategy involves preferred investors converting some of their shares to common stock. This might sound counterintuitive, but it can actually benefit everyone. By converting preferred shares to common, investors can increase their voting power in a way that aligns with the common shareholders. For example, if TechInvest converts enough shares to common, they can help push through a sale that benefits both them and the common shareholders. This also reduces the overall liquidation preference, meaning there’s more money to go around for everyone in the event of a sale.

Negotiating drag-along agreements can get complicated, which is why having a good lawyer is a good idea. In our example, let’s say you hire a lawyer to negotiate the term sheet with TechInvest. During the discussions, your lawyer might push back hard against the drag-along provision, arguing that it limits your rights as a founder. While this might seem like they are protecting you, it could actually harm the company’s ability to secure funding or execute a sale down the line.

This is where conflicts can arise. If your lawyer is too focused on protecting your personal interests, they might overlook what is best for the company as a whole. For instance, if TechInvest walks away from the deal because they feel the drag-along terms are too weak, the company could lose out on critical funding. A good lawyer should strike a balance.

Practical Implications and Conclusion

Drag-along agreements come into play in situations where a company is being acquired, merging with another business, or going through liquidation. In these high-stakes moments, the last thing a company wants is for one or two shareholders to block the entire deal. Without a drag-along clause, even a single minority shareholder could refuse to sell, creating delays, legal battles, or even scaring off potential buyers.

For small shareholders—especially those who own only a fraction of the company—it’s important to recognize when a drag-along clause is actually worth fighting over. If you own just 1% of the company, your ability to stop a sale is already limited, even without a drag-along. However, if you and a large group of small investors collectively own 30% or more, then these provisions matter a lot more because together, you might actually have the power to influence a sale. In these cases, understanding the specific voting thresholds and how drag-along provisions are structured can make a real difference.

These agreements exist because different types of shareholders have different priorities. Preferred investors, usually venture capital firms, want flexibility when it comes to selling the company. They invested with the expectation of a strong return, and they don’t want a few dissenters standing in the way when the right buyer comes along. Common shareholders, including founders and employees with stock options, might have a different perspective. As mentioned earlier, founders are often emotionally attached to the company and may want to hold out for a better deal-or not sell at all. Employees who own stock may not be enthusiastic about a sale if it does not include meaningful payouts for them. In most cases, these agreements are structured to favor investors because they have more bargaining power. However, founders who understand their options can sometimes push for fairer terms that give them a stronger voice in the decision-making process.

If you’re a small shareholder, it’s worth asking yourself: Does this really affect me? If your ownership stake is tiny, there may be more important things to focus on in the negotiations. But if you hold a significant portion of common stock—especially as a founder—you should make sure the terms are fair and that you are not giving up too much control.

At the end of the day, drag-along agreements are designed to keep things moving when a sale is on the table. Whether that is a good thing or a bad thing depends entirely on your position. If you are an investor, you probably want strong drag-along rights to prevent holdouts from blocking a deal. If you are a founder or employee, you’ll want to make sure you’re not being forced into a sale under terms that do not work for you.

The best way to protect yourself is to read the agreement carefully, ask the right questions, and, if needed, negotiate better terms before signing anything. Once the deal is done, you’re bound by those terms—so make sure you know exactly what you’re agreeing to.

When a company offers stock options to employees, it does not hand over all the shares immediately. Instead, the process of becoming fully entitled to these shares happens gradually over time, which is known as vesting.

The most common arrangement for vesting spans four (4) years. However, there is typically a condition called a “one-year cliff,” which means that employees must work for at least one year before earning any shares. Once they reach that milestone, they receive 25% of their stock options. After that, the rest of the shares are divided and awarded evenly each month over the remaining three years. This structure motivates employees to stay longer and remain invested in the company’s growth.

For founders of a company, the story can be a bit different, especially when venture capital investors get involved. Venture capitalists often require founders to also have a vesting schedule for their shares. This is partly to confirm fairness—founders need to stay committed to the company for the long haul—and partly to protect the investors’ interests.

Standard Vesting Clauses

Once the standard vesting arrangement is in place, there is usually also a safeguard known as a repurchase right. This means if an employee leaves before becoming fully vested, the company can buy back those unvested shares at a set price, often whichever is lower between the original cost or the current market value. This facilitates that any unearned equity returns to the company and can be reallocated to other employees or stakeholders.

Over the years, these practices have settled into a familiar pattern. Most early-stage companies stick to a one-year cliff and a four-year total vesting period. This schedule, now considered the industry norm, brings a sense of fairness and predictability to both employees and founders. For employees, it is clear exactly when their share of the pie stops being theoretical and becomes theirs to keep. For founders, it helps maintain balance by preventing large chunks of the company from walking out the door with someone who lost interest after a few months.

Sample Stock Vesting Clause (for illustrative purposes only, not legal advice)

Section [X]: Vesting of Shares

1. Vesting Schedule. The Recipient’s right to ownership of the Shares granted under this Agreement (the “Shares”) shall vest over a total period of four (4) years, subject to the conditions set forth herein. The vesting shall include a one-year “cliff,” followed by monthly vesting thereafter. Specifically, no Shares shall vest for the first twelve (12) months from the Vesting Commencement Date. On the first anniversary of the Vesting Commencement Date, twenty-five percent (25%) of the total number of Shares shall vest. After this initial one-year period, the remaining seventy-five percent (75%) of the Shares shall vest in equal monthly installments over the following thirty-six (36) months, with one thirty-sixth (1/36) of the remaining Shares vesting on the last day of each month thereafter, until all Shares are fully vested at the end of the four-year period.

2. Vesting Commencement Date. Unless otherwise stated in the Recipient’s offer letter or a separate written agreement, the Vesting Commencement Date shall be the Recipient’s first day of employment with the Company or another mutually agreed-upon date set forth in writing.

3. Continuous Service Requirement. Vesting of the Shares is contingent upon the Recipient’s continuous employment or service relationship with the Company or any of its subsidiaries or affiliates. If the Recipient’s employment or service terminates for any reason—whether voluntary or involuntary, and including resignation, termination with or without cause, death, or disability—no further Shares shall vest after the termination date.

4. Repurchase Right for Unvested Shares. In the event of the Recipient’s termination of employment or service for any reason prior to the vesting of all Shares, the Company shall have the right, but not the obligation, to repurchase any and all unvested Shares at a price per Share equal to the lesser of (i) the original purchase price paid by the Recipient, if any, or (ii) the fair market value of such Shares on the date of repurchase, as reasonably determined by the Company’s Board of Directors. The Company may exercise this repurchase right by providing written notice to the Recipient (or, if applicable, the Recipient’s estate) within ninety (90) days of the termination date, and completing the repurchase transaction within thirty (30) days thereafter.

5. Cliff Vesting Provision. During the initial twelve-month cliff period, the Recipient shall not vest in any Shares. If the Recipient’s employment or service terminates prior to the one-year anniversary of the Vesting Commencement Date, the Recipient shall forfeit any and all rights to any Shares that would otherwise have vested on or after that date. If, however, the Recipient remains continuously employed or engaged by the Company through the one-year anniversary, twenty-five percent (25%) of the total Shares shall vest immediately on that date.

6. Acceleration of Vesting [Optional]. In the event of a Change in Control, as defined in the Company’s governing documents, the Company’s Board of Directors may, at its discretion, accelerate the vesting of some or all of the Recipient’s unvested Shares. Any such acceleration of vesting rights shall be documented in a separate agreement or Board resolution and may be subject to additional conditions, such as the Recipient’s continued employment for a specified period post-transaction.

7. Adjustments and Amendments. The Company may, from time to time, adjust the number of Shares subject to this Agreement and/or amend the vesting schedule due to stock splits, reorganizations, or other corporate events, provided that any such adjustments shall be made in accordance with applicable law and shall not unfairly reduce the Recipient’s vested interests without the Recipient’s written consent.

8. No Guarantee of Continued Service. Nothing in this Agreement or the grant of Shares shall be construed as a guarantee of continued employment or service. The Recipient acknowledges that their employment or engagement is “at will” (except as otherwise provided by written contract), and that their status may be terminated at any time, with or without cause, subject to applicable law and any written agreements to the contrary.

Where things can diverge is in how these rules apply to founders versus everyone else. Founders, after all, often pour their time and energy into the business long before it is anything more than an idea scrawled on a whiteboard. When outside investors appear on the scene, they usually want to lock in the founders’ commitment with a vesting schedule, but it’s common for founders to negotiate some kind of “head start.” Often this comes as vesting credit, which treats them as though they’ve already put in a year or more of service. That way, when their shares begin to formally vest, it acknowledges the tough, risk-heavy work they did early on, before salaries were stable or a product even existed.

For regular employees, if they depart before hitting those crucial milestones, their unvested shares return to the company. This replenishes the option pool, making it easier to attract new recruits down the line with the promise of equity. For founders, a similar outcome arises if they leave too soon, except that the unvested shares do not simply return to a general pool. Instead, those shares effectively vanish from the departing founder’s allocation. This, in turn, slightly increases the percentage stakes of everyone else—other founders, employees, and investors—who remain with the company. Known as reverse dilution, this process facilitates that nobody gains or loses unfairly and keeps the overall ownership structure balanced and orderly.

Special Cases and Considerations in Vesting

Even though the founders usually own their shares from day one—the company still treats these shares as if they are subject to a potential buy-back. In other words, instead of waiting for the shares to “vest” like an employee would, the founder’s shares are all there immediately, but the company keeps the right to purchase back any portion that is not considered “earned” if the founder leaves early. The end result is basically the same as vesting: if the founder departs too soon, they don’t keep all their shares. However, the legal setup is different enough that it can affect how taxes are calculated.

There are also alternatives to standard vesting that founders and key employees can explore to protect their positions in the company. For example, they might negotiate for the right to purchase their unvested shares at the same price as the financing round if they leave the company. This protects their stake even if they are no longer actively involved.

Another strategy involves filing what’s known as a Section 83(b) election. This allows individuals to pay taxes on the value of their shares at the time they are granted rather than when they vest. The advantage is that if the company’s value grows significantly over time, they can lock in lower tax rates early on and potentially save a substantial amount by qualifying for long-term capital gains treatment.

The Impact of Mergers and Acquisitions

When a company goes through a merger or acquisition (M&A), it can significantly affect how vesting works. One important aspect to consider is acceleration—this refers to speeding up the vesting process so individuals gain access to their unvested shares sooner than originally planned. Acceleration comes in two main forms: single-trigger and double-trigger.

Single-trigger acceleration instantly vests all remaining shares the moment a company is bought, making it an attractive idea for those holding shares. However, most VC deals prefer double-trigger acceleration. In this setup, two things must happen before the unvested shares are fully vested: the company has to be sold, and the individual must either lose their job without a valid reason or have their role significantly altered. This approach makes sure that key players are motivated to stay and support a smooth handover after the acquisition, rather than simply cashing out and leaving as soon as the deal is done.

The reason double-trigger acceleration is popular is that it finds a fair middle ground. It keeps both founders and employees protected by making sure they do not suddenly lose their potential future gains, but it also satisfies investors and the new owners who come in after the acquisition. From the buyer’s perspective, having some unvested shares still on the table encourages the key people running the company to stick around and work hard even after the sale. If all shares were fully vested right away, the new owner might have to come up with separate plans to keep those important employees motivated, which can make the deal more complicated.

In effect, double-trigger acceleration serves everyone’s interests at once. Founders and employees do not feel short-changed if they are let go after an acquisition, and the acquirer still has a tool to ensure that the company’s team remains committed. Because of these advantages, this structure is common in venture-backed companies, helping maintain a solid balance between rewarding those who built the business and ensuring it can thrive under new leadership.

What Research and Best Practices Show

Over the past two decades, a de facto standard has emerged in the U.S. startup community: four-year vesting with a one-year cliff. This standardization itself is a product of trial, error, and refinement as startups, founders, and investors learned what works best to maintain balance and fairness.

Though formal academic studies on vesting’s direct impact on turnover are limited, anecdotal evidence and survey data from startup ecosystems (for example, “Global Startup Ecosystem” reports) suggest that reasonable vesting schedules help reduce early voluntary departures by aligning personal incentives with medium-term company milestones.

Early legal scholarship and guidance from seasoned startup attorneys frequently emphasize vesting as a mechanism to prevent “dead equity”—equity held by individuals who no longer contribute but still have voting rights and ownership stakes. A balanced vesting schedule mitigates this scenario.

Conclusion

By putting a clear vesting plan in place right from the start, everyone knows what to expect and understands that staying committed over the long run really matters. There is no need to start from scratch—tried-and-true guidelines from respected sources like the NVCA or Y Combinator can give a solid foundation.

Of course, one size does not fit all. The parties can adjust the vesting schedule for certain key players or senior team members, and even speed it up in special situations, making sure it’s fair to everyone involved. When each person’s equity matches the time and effort they have put in, they are not only reducing the chances of conflicts but also fostering a culture where the team works together smoothly.

In the long run, having a clear and fair vesting system will not just keep the team happy and in sync—it can also make the company more attractive to investors and buyers. This means simpler negotiations, better valuations, and an easier time if they ever decide to sell or bring in new partners down the road.

Imagine you’ve invested in a company, and now it’s being sold or its assets are being liquidated. A liquidation preference determines who gets paid first and how much they get before others receive anything. Think of it as a safety net for investors. If the sale price is lower than what they initially put in, this clause makes sure they get their money back before anyone else does.

There are two key parts to a liquidation preference: the preference itself and something called participation. The preference part means that, in a liquidation event, certain investors get paid a specified amount before others. So if you’re an early investor, you might be entitled to a 1× liquidation preference—meaning you get back exactly what you invested before others get paid.

Then, there’s the participation part, which comes into play after the initial preference is met. Depending on the terms, some investors not only get their money back but also share in any remaining proceeds, which adds an extra layer to their return.

Overall, liquidation preferences are there to protect investors, especially if things don’t go as planned and the company’s value doesn’t meet expectations. It’s a way for investors to manage risk while hoping for an eventual upside if the company does well.

I. Components of Liquidation Preference

Liquidation preference has two main parts that determine how money gets divided when a company is sold: (i) Actual Preference and (ii) Participation.

Actual Preference

This part, called the “actual preference,” is about giving certain investors—usually those who invested first or hold specific types of shares—priority to get paid before others when the company is sold. Think of it as a line where some investors get to go to the front and claim their share before anyone else.

For example, if investors hold what’s called “Series A Preferred” stock, they’re first in line to receive an agreed-upon amount—often the amount they originally invested—before common shareholders get anything. The reason for this setup is simple: these investors took an early risk by putting money into the company, and this priority treatment helps protect that risk.

An example of how this might be worded in an agreement is: “In the event of liquidation, Series A Preferred shareholders are entitled to receive their original investment back before common stockholders receive any payment.”

Participation

The Participation part of liquidation preference determines if certain investors can receive additional money beyond their initial preference. Once they’ve received their priority payout (the “actual preference”), some investors might also get to participate in any remaining proceeds. There are three main types of participation:

• No Participation. In this setup, investors receive only their initial preference amount and nothing more. For example, if someone invested $4 million with a 1× liquidation preference, they would receive just their $4 million back, even if there’s more money left after that. This type is sometimes called “nonparticipating preferred” stock.
• Full Participation. Here, investors get their initial preference amount and a share of any leftover proceeds. For example, if an investor has a 1× liquidation preference with full participation, they get back their initial $4 million, and then they also share in the remaining proceeds based on their ownership percentage, as though they held common stock. This allows them to benefit both from their priority payout and from any additional upside.
• Capped Participation. Capped participation lets investors receive their preference amount and a portion of the remaining proceeds, but only up to a specific limit or “cap.” For example, if an investor’s cap is set at 2.5× their original investment, and they invested $4 million, they can receive up to $10 million in total ($4 million preference plus up to $6 million more from participation). Once they reach this cap, they don’t receive any additional payout, regardless of how much more is available.

II. Conversion and Participation

In liquidation preferences, conversion allows investors with preferred shares to switch their shares to common stock under certain conditions. This option gives them flexibility, as they can choose to convert if it will result in a higher payout. The decision to convert usually depends on a conversion ratio, which specifies how many common shares an investor receives in exchange for each preferred share.

Let’s break it down with an example.

Imagine an investor owns preferred stock with a 1:1 conversion ratio, meaning each preferred share can be converted into one common share. If the company is being sold, the investor can either (a) stick with the liquidation preference and receive their original investment back first or (b) convert their preferred shares into common stock and receive a share of the total sale proceeds based on their ownership percentage.

Here’s a scenario to illustrate how conversion might work:

1. Example 1 “No Conversion Needed”. Suppose the investor put in $3 million and has a 1× liquidation preference. The company is being sold for $4 million. In this case, the investor would likely choose not to convert, as sticking with the 1× liquidation preference guarantees them $3 million back before anyone else is paid. Converting would only dilute their payout, so they opt to keep their preferred status.
2. Example 2 “Conversion for a Higher Payout”. Now, let’s say the company is sold for $10 million, and the investor has 25% ownership in preferred shares. With a 1× liquidation preference, they could take back their original $3 million, but converting their shares to common stock would give them 25% of the $10 million sale price, or $2.5 million. In this case, they might choose to keep their preferred stock for the guaranteed $3 million payout, rather than converting to common and receiving a lower amount.
3. Example 3 “High-Value Sale and Conversion Advantage”. Finally, imagine a big exit where the company is sold for $20 million. Now, if the investor has 25% of the company, converting to common stock would result in a $4 million payout (25% of $20 million). In this case, conversion is beneficial because they can receive more than the $3 million from sticking with the liquidation preference.

III. Examples of Participation Scenarios

Let’s go over four different scenarios that show how participation terms impact investor and common stockholder payouts in a company sale. We’ll use examples with different types of liquidation preferences: 1× nonparticipating, 2× nonparticipating, 1× fully participating, and 1× capped at a 3× multiple.

Assume:

• The investor originally invested $2 million, holding 40% of the company.
• The common stockholders own the remaining 60%.
• We’ll look at company sale values of $3 million, $10 million, $20 million, and $50 million.

Case 1. 1× Nonparticipating Preference

Terms: The investor has a 1× nonparticipating preference, meaning they can either take their initial $2 million investment back first or convert to common shares to receive 40% of the sale if it’s higher.

Sale Scenarios:

• $3 million sale: The investor takes their 1× preference, getting $2 million, leaving $1 million for common holders.
• $10 million sale: The investor could take their 1× preference ($2 million) or convert to receive 40% of $10 million ($4 million). They choose to convert, taking $4 million, while common stockholders get $6 million.
• $20 million sale: The investor converts to common to take 40% of $20 million, or $8 million. Common holders receive $12 million.
• $50 million sale: Again, the investor converts to common, receiving 40% of $50 million, or $20 million, with the remaining $30 million going to common holders.

Case 2: 2× Nonparticipating Preference

Terms: The investor has a 2× preference, which entitles them to twice their initial investment ($4 million) before common holders get anything.

Sale Scenarios:

• $3 million sale: The investor’s 2× preference entitles them to $4 million, but since the sale is only $3 million, they take the entire amount, leaving nothing for common holders.
• $10 million sale: The investor takes their 2× preference of $4 million, leaving $6 million for common holders.
• $20 million sale: The investor takes $4 million, with common holders receiving the remaining $16 million.
• $50 million sale: The investor converts to common to take 40% of $50 million ($20 million), which is higher than their $4 million preference. Common holders receive $30 million.

Case 3: 1× Fully Participating Preference

Terms: The investor has a 1× preference with full participation, meaning they first receive $2 million, and then share in the remaining proceeds based on their ownership.

Sale Scenarios:

• $3 million sale: The investor takes their $2 million preference, leaving $1 million for common holders.
• $10 million sale: The investor receives their $2 million preference and 40% of the remaining $8 million ($3.2 million), totaling $5.2 million, while common holders get $4.8 million.
• $20 million sale: The investor takes $2 million first, then 40% of the remaining $18 million ($7.2 million), for a total of $9.2 million, with common holders getting $10.8 million.
• $50 million sale: The investor receives $2 million, then 40% of the remaining $48 million ($19.2 million), totaling $21.2 million, with common holders getting $28.8 million. 

Case 4: 1× Preference with a 3× Cap

Terms: The investor has a 1× preference with participation capped at 3×, meaning they get back their $2 million investment and can participate up to a $6 million maximum payout.

Sale Scenarios:

• $3 million sale: The investor takes the $2 million preference, leaving $1 million for common holders.
• $10 million sale: The investor receives their $2 million preference and 40% of the remaining $8 million ($3.2 million), totaling $5.2 million. Since this is below the 3× cap, they keep it all, and common holders get $4.8 million.
• $20 million sale: The investor takes their $2 million preference and 40% of the remaining $18 million ($7.2 million), totaling $9.2 million. However, they’re capped at $6 million, so they stop there, and common holders receive the remaining $14 million.
• $50 million sale: Here, the investor also reaches their cap of $6 million, as their participation amount would otherwise exceed it. Common holders receive the remaining $44 million.

IV. Impact of Multiple Investment Rounds on Liquidation Preference

As a company raises more rounds of investment, liquidation preferences can become more complex. When multiple rounds (like Series A, B, and C) have different investors with varying priorities, there are two main ways these preferences can be structured: Stacked Preferences or Blended Preferences (also known as pari passu).

Stacked Preferences

With stacked preferences, each investment round has priority based on when it was made, with later rounds getting paid first. This structure is sometimes favored by newer investors who want assurance that they’ll recover their investment ahead of earlier rounds. Here’s how it might work in practice:

• Imagine a company has raised three rounds: Series A ($3 million), Series B ($7 million), and Series C ($10 million), for a total of $20 million in investments.
• If the company is sold for $15 million, Series C investors, having the latest round, would be paid back first. They receive their $10 million investment, leaving $5 million.
• Series B investors would then receive up to their $7 million investment from the remaining $5 million, but since that’s all that’s left, they only recover $5 million.
• Series A investors would receive nothing because the sale price doesn’t cover earlier investors’ stacked preferences.

Stacked preferences make each subsequent investment round riskier for previous investors, as they move further down the payout line if the company doesn’t achieve a high sale price.

Blended Preferences (Pari Passu)

In blended preferences, or pari passu structure, all rounds share the proceeds proportionately based on their investment amounts, without one round being prioritized over another. This approach spreads the risk more evenly among investors in different rounds.

• Using the same investment amounts as above, let’s say the company is again sold for $15 million.
• With blended preferences, the proceeds are distributed pro-rata. Here’s how it might work:
  • Series A, which contributed $3 million, would receive a proportionate share of the sale price: 15% of the $15 million, or $2.25 million.
  • Series B, which invested $7 million, would receive 35%, or $5.25 million.
  • Series C, with the highest investment of $10 million, would receive 50%, or $7.5 million.

In this scenario, all rounds of investors get some return, rather than later investors getting prioritized. Blended preferences are often seen as fairer when the company has a diverse set of investors who all took risks at different stages.

The choice between stacked and blended preferences often depends on the investors’ bargaining power and the company’s needs. Later-stage investors, like Series C, may prefer stacked preferences to maximize recovery if the exit is small. Meanwhile, blended preferences are more equitable and can appeal to early investors by giving everyone a fair share of proceeds, regardless of the investment sequence.

V. Negotiating Liquidation Preferences

When setting up liquidation preferences, companies and investors must find a balance that protects investors while also keeping employees and management motivated. Liquidation preferences should ideally provide security for investors without overly limiting the potential rewards for the team running the company.

Investors typically want liquidation preferences to secure their investment, especially in the early stages when the company’s future is uncertain. However, setting high or complex preferences can limit the amount left over for employees and management, who are usually holding common stock or options. If team members feel they won’t see significant rewards unless the company has a very high sale price, their motivation to drive the company forward may decrease.

For example:

• Suppose an early-stage company raised $1 million in a seed round with a 2× liquidation preference, guaranteeing the seed investor $2 million in a sale before any proceeds reach common shareholders.
• If the company later sells for $3 million, the investor would take $2 million, leaving only $1 million for all common shareholders, including employees and management.
• In this scenario, the small remaining payout may discourage employees, as they see limited upside unless the company achieves a very high exit.

Finding a balance often means negotiating preferences that protect investors without excessively reducing potential returns for the team. For instance, a 1× preference, rather than 2× or 3×, can offer investors downside protection while still allowing meaningful upside for common shareholders in smaller exits.

Best Practice: Keeping Preferences Simple and Lightweight in Early Rounds

In early rounds, it’s generally advisable to use straightforward and low-level liquidation preferences, such as a 1× nonparticipating preference. This simple structure ensures that investors get their initial investment back but doesn’t add layers of complexity or significantly impact the returns available to employees and management.

For example:

• A company raises $500,000 in its seed round, with a 1× nonparticipating liquidation preference. If the company is sold for $2 million, the investor would take back their $500,000 first, leaving $1.5 million to be shared among common shareholders, which includes employees and founders.
• This simple approach gives early employees and management a strong incentive, as they can see a meaningful return in even moderately successful exits.

VI. Defining a Liquidation Event

A liquidation event is any situation where a company undergoes a significant change in ownership or control, triggering the payout rights defined in the liquidation preference terms. Liquidation events often include mergers, acquisitions, and changes in control, but they can also cover situations like the sale of all or most of the company’s assets. These events are essential to define in investment agreements because they determine when and how investors receive their payouts.

Types of Liquidation Events

1. Merger. When a company combines with another entity to form a new organization. For example, if Company A merges with Company B, creating a new merged entity, it can trigger a liquidation event for shareholders.
2. Acquisition. When one company buys out another, either through a purchase of shares or assets. For instance, if Company X acquires all shares of Company Y, this acquisition is a liquidation event for Company Y’s shareholders.
3. Change of Control. When there’s a significant shift in who holds controlling interest or voting power within the company. This could be through a sale of majority shares or a voting power transfer. For example, if a new investor acquires 70% of the voting shares, it may be classified as a liquidation event, allowing other investors to receive their payouts.
4. Sale of Major Assets. If a company sells off most of its assets or business units, this can also trigger a liquidation event. For example, if a tech company sells all its intellectual property and core assets, this sale could be treated as a liquidation event.

Standard Language for Defining a Liquidation Event

To ensure clarity, investment agreements often include precise language to define what qualifies as a liquidation event. Here’s an example of standard language:

“Liquidation Event. A liquidation event includes (a) any merger or consolidation of the Company with another entity in which the Company’s existing shareholders do not retain a majority of the voting shares in the surviving entity; (b) the sale, lease, or transfer of all or substantially all of the Company’s assets; (c) the sale or transfer of more than 50% of the Company’s voting stock to a single entity or group acting together; or (d) any other transaction in which the Company’s shareholders receive cash, stock, or other securities in exchange for their shares.”

The term “security” may sound straightforward, but in law, it carries significant weight. Knowing what qualifies as a security might become critical, as it determines whether a transaction must comply with securities regulations. This distinction does not just affect buyers and sellers. It also involves brokers, advisors, and other intermediaries who play a role in these transactions. 

For businesses and individuals, identifying whether a financial instrument is classified as a security shapes how they operate. Adhering to securities laws can be complex, time-consuming, and expensive. Failing to comply can lead to severe penalties, including hefty fines or legal action. That is why it is essential to have a clear understanding of when these regulations apply and how to stay compliant. 

The Importance of Definition

When an instrument is classified as a security, several significant legal requirements and protections come into play:

• Companies issuing securities must register them with the SEC unless an exemption applies. This process involves providing detailed information about the company’s business, finances, and management to the public (See Securities Act of 1933, Sections 5 and 7).
• Issuers and related parties are subject to heightened antifraud provisions. Misleading statements or omissions of material facts can lead to severe legal consequences. For example, Section 10(b) of the Securities Exchange Act and Rule 10b-5 prohibit fraudulent activities in connection with the purchase or sale of any security.
• Brokers, dealers, and other intermediaries involved in securities transactions must register with the SEC and are subject to its rules and supervision. This oversight aims to protect investors from unethical practices (Refer to Securities Exchange Act of 1934, Section 15).
• Violations of securities laws can result in civil lawsuits, SEC enforcement actions, and even criminal charges. Penalties may include fines, disgorgement of profits, and imprisonment. The Sarbanes-Oxley Act of 2002, for instance, increased penalties for corporate fraud and imposed stricter regulations on corporate governance.

Legal Foundations of a “Security”

Federal Securities Laws

The federal securities laws, primarily the Securities Act of 1933 and the Securities Exchange Act of 1934, provide a comprehensive list of financial instruments considered to be securities. The statutes specifically enumerate certain instruments as securities. These include stocks, bonds, debentures, notes, and transferable shares. Each of these instruments represents a form of investment where individuals provide capital with the expectation of receiving financial returns.

In addition to these specified instruments, the laws include catchall terms to encompass a broader range of financial arrangements. These terms are “evidences of indebtedness,” “investment contracts,” and “certificates of interest in profit-sharing agreements.” The inclusion of these categories ensures that the laws remain adaptable to new and innovative financial products that may not fit neatly into the traditional categories. For example, an “investment contract” is a flexible term that can apply to various schemes where people invest money with the expectation of profits derived from the efforts of others. This term was intentionally left broad to prevent promoters from evading securities laws by creating novel investment vehicles not explicitly listed.

An important feature of these definitions is the phrase “unless the context otherwise requires.” This clause means that even if an instrument falls within one of the enumerated categories, it might not be considered a security if the specific context suggests otherwise. This provision allows for flexibility, ensuring that the application of securities laws aligns with the intent of the legislation and the realities of the marketplace.

Judicial Interpretation

While the statutory definitions provide a framework, courts often play their own role in interpreting these definitions, especially when dealing with unconventional investments. Two key questions arise in judicial interpretations:

1. When do unorthodox investments fall under catchall terms like “investment contract”?
2. When might instruments that fit an enumerated category not be considered securities?

To answer these questions, courts examine the economic realities of the transactions rather than relying solely on the formal titles of the instruments. This approach helps prevent individuals or companies from circumventing securities laws through creative labeling.

One landmark case that addressed the first question is SEC v. W.J. Howey Co., 328 U.S. 293 (1946) – Howey case.” In this case, the Supreme Court established the “Howey Test” to determine whether a particular scheme qualifies as an investment contract and, therefore, a security. The test considers whether there is an investment of money in a common enterprise with an expectation of profits derived primarily from the efforts of others. If these elements are present, the investment arrangement is considered a security, regardless of its form.

Regarding the second question, courts recognize that some instruments might superficially appear to be securities but, in substance, are not. For example, not all notes are securities. In Reves v. Ernst & Young, 494 U.S. 56 (1990), the Supreme Court introduced the “family resemblance” test to determine when a note is a security. This test presumes that a note is a security but allows for exceptions if the note closely resembles instruments that are not securities, such as short-term notes secured by a lien on a small business or consumer loans.
Courts consider several factors in this analysis, including the motivations of the buyer and seller, the plan of distribution, the reasonable expectations of the investing public, and the presence of alternative regulatory schemes that reduce the risk of the instrument.

The absence of a unified judicial approach arises because courts may emphasize different aspects of these factors. Some courts focus on the level of commonality among investors, distinguishing between horizontal commonality (where investors pool their resources) and vertical commonality (where a single investor’s fortunes are linked to the promoter’s efforts). Others may prioritize the degree of control investors have over their investments.

A central theme in judicial interpretations is the role of investors entrusting their money to others. When investors lack control over the management of their funds and rely on the expertise or efforts of others to generate profits, there is a heightened need for regulatory oversight to protect their interests. This situation gives rise to agency problems, where the managers (agents) may not act in the best interests of the investors (principals). Additionally, when there are many investors, collective action problems make it difficult for them to coordinate and monitor the managers effectively.

The Howey Test for “Investment Contracts”

Understanding what constitutes an “investment contract” is essential in determining whether a financial arrangement is subject to federal securities laws. One of the most significant developments in this area, as we mentioned above, is the establishment of the Howey Test, which originated from the“Howey case.”

In the Howey case, the W.J. Howey Company sold parcels of citrus groves in Florida to investors, offering them optional service contracts where Howey would cultivate, harvest, and market the citrus on their behalf. Many investors were not farmers and had no intention of working the land themselves. The Securities and Exchange Commission (SEC) argued that these transactions were “investment contracts” and should be registered as securities.

The Supreme Court agreed with the SEC and established a four-pronged test to determine when a transaction qualifies as an investment contract:

1. An investment of money;
2. In a common enterprise;
3. With an expectation of profits;
4. Derived solely from the efforts of others.

The Court emphasized that the determination should be based on the “economic realities” of the transaction rather than its form or terminology.

Detailed Breakdown of the Howey Test

Investment of Money

The first element requires that an individual invests money. This investment is not limited to cash; it can include other forms of consideration, such as services or property. The critical aspect is that the investor provides something of value with the intention of receiving a financial return. The investor is seeking profits, not merely purchasing a consumable commodity or service for personal use.

In a Common Enterprise

The second element involves a common enterprise. Courts have interpreted this in two primary ways:

1. • Horizontal Commonality. This is the majority view, where multiple investors pool their funds into a common venture, and their returns are tied to the collective success of the enterprise. For example, if several investors contribute to a fund managed by a company, and their profits depend on the overall performance of that fund, horizontal commonality exists.
   • Vertical Commonality. Some courts, though in the minority, accept vertical commonality, where an individual investor’s success is directly linked to the promoter’s efforts. There are two types:
     • Broad Vertical Commonality. The investor’s fortunes are linked to the efforts of the promoter, but not necessarily to the promoter’s profits.
     • Narrow Vertical Commonality. The investor’s profits are directly correlated with the promoter’s profits.

Regardless of the approach, the essence is that the investor is part of a venture where their financial outcome is connected to the performance of the enterprise or the promoter.

Expectation of Profits

The third element requires that the investor enters the transaction with the expectation of earning profits. These profits can come from income (like dividends or interest) or capital appreciation. The motivation should be financial gain, distinguishing investment contracts from transactions where the primary intent is to consume a good or service. Importantly, profits should be derived from the earnings of the enterprise or appreciation in the value of the investment, not merely from the contributions of additional investors (as in a Ponzi scheme).

Derived Solely from the Efforts of Others

The fourth element focuses on who is responsible for generating the profits. The investor’s expected profits must come predominantly from the efforts of someone other than themselves. Although the original wording uses “solely,” courts have interpreted this element flexibly, recognizing that investors may have some involvement. The key factor is that the managerial efforts of promoters or third parties are the essential factors in the success or failure of the enterprise. The investor’s role is largely passive, relying on the expertise and efforts of others.

The Howey Test has also been applied in various cases to determine whether certain schemes qualify as investment contracts:

• In Smith v. Gross, 604 F.2d 639 (9th Cir. 1979), promoters sold earthworm beds to investors, promising to repurchase the worms and provide marketing assistance. Investors were enticed by the prospect of high profits without needing expertise in worm farming. The court found this arrangement to be an investment contract.
• In SEC v. Koscot Interplanetary, Inc., 497 F.2d 473 (5th Cir. 1974), participants paid to join a multi-level marketing scheme selling cosmetics. Profits were primarily derived from recruiting new participants rather than retail sales. The court held that such schemes are investment contracts because participants invest money with the expectation of profits from the efforts of others in the recruitment chain.

Extending Howey’s Principles Beyond Unorthodox Investments

The Howey Test is not limited to unorthodox or novel investment schemes. Courts have also applied its principles to more traditional financial instruments when assessing whether they qualify as securities. The federal securities laws list specific instruments as securities, including stocks, bonds, debentures, and notes. However, the statutes include a provision stating that these instruments are securities “unless the context otherwise requires.” This clause allows for flexibility, recognizing that not all instruments labeled as “stocks” or “notes” function as securities in practice.

Instances Where Instruments May Not Be Securities

Notes

While notes are generally presumed to be securities, the Supreme Court in Reves v. Ernst & Young, 494 U.S. 56 (1990) established the “family resemblance” test to determine when a note is not a security. Under this test, a note is considered a security unless it bears a strong resemblance to a type of note that is not a security, such as:

1. • Short-term notes secured by a lien on a small business or its assets.
   • Notes evidencing a character loan to a bank customer.
   • Notes secured by a home mortgage.
   • Short-term notes secured by accounts receivable.

Reves v. Ernst & Young involved demand notes issued by a farmer’s cooperative. The Court held that these notes were securities because they did not fit into any recognized exceptions and investors were led to expect profits from the cooperative’s efforts.

Stocks

Although stocks are the quintessential example of securities, there are rare instances where an instrument labeled as “stock” may not be a security. The Supreme Court in United Housing Foundation, Inc. v. Forman, 421 U.S. 837 (1975) examined “stock” in a cooperative housing corporation. Investors purchased shares to obtain the right to lease an apartment, not for investment purposes. The Court concluded that the shares were not securities because they lacked the characteristics of traditional stock, such as the expectation of dividends, transferability, and appreciation in value.

The key principle in securities regulation is that substance prevails over form. Simply labeling an instrument as a “note” or “stock” does not automatically make it a security. Courts scrutinize the actual characteristics and purpose of the instrument:

• If the primary intent is to use or consume the item purchased (as in purchasing cooperative housing for living purposes), it may not be a security (investor’s intent).
• Transactions resembling commercial loans or consumer financing are typically not securities (nature of the transaction).
• Securities laws aim to protect investors in situations where they are at a disadvantage due to lack of information and control over their investments (level of risk and information asymmetry).

The Risk Capital Test as an Alternative Approach

While the Howey Test is the primary method used by federal courts to determine whether an investment qualifies as a security, some state courts have adopted an alternative approach known as the Risk Capital Test. This test is particularly relevant under state “blue sky” laws, which are state securities regulations designed to protect investors from fraudulent investment schemes.

The Risk Capital Test focuses on whether an investor’s funds are placed at risk in a venture over which they have no managerial control. Unlike the Howey Test, the Risk Capital Test centers on the vulnerability of the investor’s initial capital.

This approach originated from the California Supreme Court case Silver Hills Country Club v. Sobieski, 55 Cal. 2d 811 (1961). In this case, promoters sold memberships in a planned country club to finance the development of its facilities. The court held that these memberships were securities under California law because the investors’ funds were used to finance a speculative venture, and the investors had no control over how their money was used.

The Risk Capital Test has been utilized by courts in several states to interpret their securities laws, often leading to a broader definition of what constitutes a security compared to federal law.

The Risk Capital Test differs from the Howey Test in significant ways:

• The Risk Capital Test does not necessitate a common enterprise or the pooling of funds among multiple investors. A single investor’s capital at risk can suffice (no requirement of commonality).
• Unlike the Howey Test, which requires an expectation of profits primarily from the efforts of others, the Risk Capital Test focuses solely on the risk to the investor’s initial capital, regardless of who is responsible for generating returns (no need for profits derived from others’ efforts).
• The test centers on whether the investor’s funds are subject to the risks of an enterprise over which they have no managerial control, making them dependent on the promoter’s honesty and competence (emphasis on capital at risk).

In another case (State v. Hawaii Market Center, Inc., 485 P.2d 105 (Haw. 1971) investors purchased memberships in a discount buying club that promised future benefits contingent on the club’s successful establishment and operation. The Supreme Court of Hawaii applied the Risk Capital Test (economic realities) and concluded that these memberships were securities because the investors’ funds were used to finance the venture, and they lacked control over how their money was utilized.

Conclusion

As new financial instruments emerge—such as cryptocurrencies, alternative assets, and innovative investment schemes—they often blur the lines of traditional definitions. These advancements challenge regulators and courts to reassess and interpret the term “security” in contexts that were unimaginable when the original laws were enacted.

The dynamic nature of these investment vehicles/instruments means that courts must continually adapt. They strive to balance the need for investor protection with the encouragement of market innovation. On one hand, stringent definitions may stifle creativity and the development of new financial products. On the other hand, overly lax interpretations can leave investors vulnerable to fraud and abuse.

Looking ahead, there is potential for legislative updates or new judicial standards to address the changing and developing landscape of financial instruments. The rise of decentralized finance (DeFi), non-fungible tokens (NFTs), and other digital assets may prompt lawmakers and regulators to refine or expand existing definitions.

The need for clarity is paramount. Clear guidelines help investors make informed decisions, assist issuers in complying with regulations, and enable legal practitioners to provide accurate advice. Regulatory bodies like the SEC continue to issue guidance and engage in rulemaking to address novel financial products. For example, in recent years, the SEC has provided insights into when digital assets may be considered securities under the federal securities laws. 

The journey to define a “security” is ongoing and reflects the dynamic interplay between law, finance, and innovation. While the complexity presents challenges, it also offers opportunities for the legal system to adapt and protect investors in new ways.

Participation in the resale market for venture capital funds is crucial for investors who wish to liquidate their investments earlier than initially anticipated. This requirement might be due to diverse personal or strategic financial points like a sudden demand for liquidity or a wish to rebalance one’s investment portfolio. As an increasing number of investors demonstrate a proclivity to sell shares that do not align with the designated settlement date, there is a corresponding rise in the number of prospective purchasers who are interested in acquiring these stakes.

Venture capital entities have already effectively adapted to the growing dynamism in this secondary market. They have standardized the documentation and processes to facilitate these equity transfers efficiently. Although the process is designed to be streamlined, recent regulatory changes in the U.S. have introduced some complexities. For instance, tax regulations under Section 1446(f) of the Internal Revenue Code necessitate the withholding of taxes when shares are sold by non-U.S. investors, complicating the payout process.

Suppose there is a case involving a non-U.S. investor, who is looking to divest their venture capital fund shares. According to the IRS tax guidelines, a portion of the sale proceeds must be withheld for tax purposes before distributing the remaining funds to the seller.

Tax Implications for Non-US Investors Under Section 1446(f)

In the example we discussed, where non-U.S. investor (limited partner) wants to sell their shares in a venture capital fund, they face specific tax obligations under U.S. law, particularly under Section 1446(f). This section deals with how profits from the sale are taxed if the fund itself would have made a profit in a hypothetical situation where all its assets were sold at their current market value.

Let’s break it down: suppose a non-U.S. investor sells their interest in a venture capital fund and makes a $1,000,000 profit. If the fund, in a theoretical sale of all its assets, would have made a profit where 10% of that profit was connected to U.S. business activities, then $100,000 of the investor’s $1,000,000 profit would be considered connected to U.S. business (“effectively connected income”, or “ECI”).

For U.S. investors, this ECI designation does not really change anything; they must pay U.S. taxes on all their gains regardless. However, for non-U.S. investors, whether their profit counts as ECI is crucial. If none of their profit is ECI, they typically would not owe U.S. taxes on it. But if some of the profit is ECI, as in our example, they face U.S. tax obligations.

Under Section 1446(f), when a non-U.S. investor sells their fund interest, the buyer of that interest has to act almost like a tax collector for the IRS. Specifically, the buyer must withhold 10% of the total amount the seller gains from the sale. So in our example, if a non-U.S. investor gains $1,000,000 from the sale, the buyer needs to withhold $100,000 and send it to the IRS.

If the buyer forgets or fails to withhold this amount, the venture capital fund itself is then responsible for making sure the IRS gets its due. The fund must withhold the necessary tax from any future payments it was supposed to make to the buyer related to the investment.

Moreover, the buyer has to confirm to the venture capital fund how they have met these withholding requirements. They need to provide a formal certification detailing this compliance within 10 days after the sale.

Withholding Tax Exceptions for Non-US Venture Capital Investors 

It is also important to know that there are several exceptions to these rules under Section 1446(f) that might prevent the need for withholding tax at all.

First, let’s look at exceptions related to certifications by the non-U.S. limited partner who is selling their interest. One way to avoid withholding is if this partner certifies that their sale does not result in any actual profit or gain. Essentially, if they’re not making any money from the sale, there’s no income to tax, so no withholding is necessary.

Another way is a bit more complex but comes down to the partner’s previous tax history with the fund. If the selling partner can certify that they’ve been part of the fund for the last three tax years, and during each of those years, their share of effectively connected income (ECI) was both under $1,000,000 and less than 10% of their total income from the fund, and they have correctly reported this income and paid any taxes due on it in the U.S., then withholding can be skipped. This shows the IRS that the seller has a consistent history of small-scale involvement in terms of taxable U.S. operations and compliance with U.S. tax laws.

There are also exceptions based on certifications from the venture capital fund itself. If the fund can certify that it was not engaged in any U.S. trade or business at any point during its current tax year up to the transfer date, then no withholding is required because there’s no U.S. business activity connected to any gains.

Alternatively, if the fund can prove that even if all its assets were sold at a current market value (a deemed sale), the resulting ECI would not make up more than 10% of the total gain from such a sale, or the non-U.S. partner’s share of ECI would not be moree than 10% of total income from the sale, then again, withholding is not needed. This would indicate that a connection to U.S. business activities is really minor enough not to trigger the need for tax collection.

Section 1446(f) Challenges for Non-US Investors

Applying the exceptions from withholding taxes under Section 1446(f) can be tricky and is not always so cut-and-dried, primarily due to some qualifying conditions and the need for cooperation among different parties involved.

For instance, one significant hurdle is the requirement for a non-U.S. limited partner (the seller) to have held their interest in the venture capital fund for at least three full tax years to qualify for certain exceptions. If a partner has not met this tenure requirement, they cannot use the exception related to having minimal ECI below the thresholds of $1,000,000 or 10% of their total income from the fund. This can be quite limiting, especially for newer investors who may be looking to exit earlier than this timeframe.

Additionally, the process of obtaining necessary certifications either from the non-U.S. limited partner or directly from the venture capital fund itself often requires considerable coordination and cooperation. The transferee (the buyer) relies heavily on these other parties to provide accurate and timely certifications that confirm no withholding is necessary. Any delays or inaccuracies in this process can complicate the transaction and may inadvertently lead to withholding obligations.

Moreover, if a situation arises where the required withholding was not executed by the transferee, the venture capital fund itself becomes responsible for ensuring compliance. This secondary withholding obligation necessitates the fund to know exactly how much was realized from the sale of the non-U.S. partner’s interest—a detail that the fund might not have immediate access to. This lack of information can complicate how the fund manages its subsequent distributions, particularly when it comes to withholding the correct amounts from future payments to the transferee.

Overall, while the exceptions under Section 1446(f) provide pathways to avoid withholding taxes, the actual application of these exceptions can be complex and fraught with challenges, often depending on precise documentation and the cooperative effort of all parties involved in the transaction.

Double Tax Treaty Implications

The application of double taxation treaties (DTT) may have a significant impact on the withholding tax rate stipulated by Section 1446(f) when a non-U.S. investor disposes of shares in a U.S. venture capital fund. In the absence of a tax treaty, the default rate is 10% on the gross proceeds from the sale of partnership interests by foreign partners. However, this rate can be adjusted or waived if a tax treaty between the United States and the investor’s country of residence offers more favorable terms.
The effective application of DTTs necessitates compliance with the requisite documentation and procedural requirements. For example, non-U.S. investors may be required to submit IRS Form W-8BEN in order to certify their residence in a treaty country and qualify under the “limitation of benefits” provisions of the DTT, thus enabling them to benefit from the treaty provisions. Failure to provide this form accurately and in a timely manner can result in the automatic application of the statutory withholding rate, regardless of any treaty provisions that might otherwise reduce the investor’s tax liability.

A very recent ruling by the Supreme Court came on June 27, 2024, in Securities and Exchange Commission v. Jarkesy, which held that the Seventh Amendment to the U.S. Constitution requires the Securities and Exchange Commission (SEC) to bring a civil penalty for securities fraud in the federal district courts before a jury, not through an administrative proceeding.

The SEC charged George Jarkesy, Jr. and his investment firm, Patriot28, LLC, with fraud in connection with the operation of their investment funds. If the SEC believes that someone has violated the securities laws, it has two options: It can bring the case in federal court or handle the matter internally through its administrative proceedings. In this case, the target for alleged violations of the securities law was adjudicated by the SEC itself. Thus, the action was handled by an administrative law judge—who works for the SEC—rather than a federal court.

This raises some very serious legal questions under the Seventh Amendment, which ensures there will be a trial by jury in certain civil cases. So, the real basic legal question of this case was whether under the Seventh Amendment, Jarkesy and his firm had a constitutional right to a jury trial in light of the SEC’s decision to handle prosecution of the charges in-house.

The Supreme Court has ruled that the SEC’s internal case handling method, which does not offer a jury trial, violates the Seventh Amendment. Now this could have a significant impact on how the SEC and potentially other federal agencies enforce their rules.

The SEC’s Enforcement Action

The SEC enforcement charged several instances of allegations for fraud-related activities.

• Misrepresentation of Investment Strategies. The SEC charged Jarkesy and Patriot28 with the misrepresentation of investment strategies to misled investors.
• False Information Regarding the Auditor and Broker. Jarkesy and his firm were also charged with false representations regarding an auditor and a prime broker for the funds.
• Inflating the Value of the Funds. Another grave allegation was that Jarkesy and his firm inflated the value of the funds under their management.

The SEC took the following enforcement actions in response to the allegations:

• Civil Penalties. A civil penalty of $300,000 was imposed by the SEC on Jarkesy and Patriot28. Civil penalties include money fines that the SEC can levy to punish wrongdoing and deter wrongdoers.
• Cease and Desist Order. The Commission ordered Jarkesy and Patriot28 to cease and desist from committing or causing any violations of the antifraud provisions of the securities laws. This is a standard regulatory step to prevent the believes from continuing whatever activity is charged as illegal under securities laws.
• Disgorgement. It was ordered that Patriot28 disgorge the ill-gotten gains by returning money or property gained in an illicit manner to the parties concerned.
• Industry Bars. Jarkesy has been barred from the securities industry and penny stock offerings.
• Adjudication Process. Instead of taking it before a federal court, the SEC chose to conduct the case internally within its administrative process. It involved an administrative law judge appointed by the SEC, which created much legal controversy as to the appropriateness of such denial of a jury trial in cases relating to civil penalties against securities fraud.

Seventh Amendment Overview

The legal analysis of the Seventh Amendment claims in SEC v. Jarkesy turns on whether defendants have the right to a jury trial when the SEC decides to pursue civil penalties in its internal administrative proceedings rather than in federal district court. The question at hand was centrally located within the determination of the constitutional limits of the different administrative enforcement actions by regulatory agencies like the SEC.

The Seventh Amendment grants the right to trial by jury in civil cases at common law if the amount in controversy be greater than twenty dollars.

The power of the SEC to enforce the securities laws either through administrative proceedings or through filing actions in federal court is long-established. When administrative proceedings are initiated, they typically do not involve juries, which raises a constitutional question.

In contrast, civil penalties, which are monetary in nature, are not merely compensatory and thus punitive in nature. They are intended to punish and deter wrongful conduct, and therefore have a punitive character. While actions for penalties could be tried by a jury at common law, similar actions under modern law may also require a jury.

In Granfinanciera, S.A. v. Nordberg (1989), the Supreme Court held that a statutory action of this nature, much like an action brought at common law, does grant the defendant the right to trial by jury under the Seventh Amendment if its judgment may lead to “personal liability” for money damages. The Court distinguished between actions that primarily concern public rights and those that primarily concern private rights disputes, which are more characteristic of the common law.

In Atlas Roofing Co. v. Occupational Safety and Health Review Commission (1976) the Supreme Court had held that it was within congressional power to assign the determination of statutory rights created by Congress to an administrative agency, with no right to a jury. However, this has been interpreted to apply to cases where the statutory framework creates new legal rights and obligations distinct from traditional common law actions.

In Tull v. United States (1987) the Supreme Court again restated that the right to a jury trial depends on the remedy sought. When relief is sought through penalties or action punitive in nature—characteristics traditional to common law—the right to trial by jury is preserved.

The critical legal question of SEC v. Jarkesy lies in the query: Did the SEC’s pursuit of civil penalties through its in-house, administrative processes without providing a right to a jury violate the Seventh Amendment?

Additionally, the arguments presented in the case hinge on whether the SEC’s action can be classified as a public rights adjudication, which typically does not require a jury, or rather, a private rights dispute that is subject to a jury trial. Given that the penalties in question are punitive and that the fraudulent nature of the actions otherwise alleged is grounded in common law history, it would be strongly in line with the Seventh Amendment to call upon a jury to determine the case.

Court’s Decision and Reasoning

The Supreme Court ruled that defendants have a right to a jury trial under the Seventh Amendment when the SEC seeks civil penalties for securities fraud.

The Court noted that the civil penalties sought by the SEC are, in fact, punitive rather than remedial. The basic purpose of such penalties is not so much to compensate the victim as to punish the offender and deter others from similar wrongdoing. It is this punitive nature that brings them more accurately within the concept of traditional common law actions, where the right to a jury trial is preserved.

Additionally, the SEC’s enforcement actions were based on allegations of fraud. The Court pointed out that fraud, historically a common law claim, involves deception and misrepresentation—actions traditionally adjudicated by juries. The SEC’s use of terms like “fraud” and “deceit” in its enforcement actions invokes common law principles, which necessitate a jury trial under the Seventh Amendment.

The “public rights exception” to the Seventh Amendment allows some legal claims to be decided without a jury, namely those involving public rights that Congress commits to resolution by administrative agencies or specialized courts. But the Court held this exception did not apply here, at least for the following reasons:

• Private vs. Public Rights. The Court distinguished between public rights, which are integral to a public regulatory scheme and typically do not require jury involvement, and private rights, which involve personal interests and are closely tied to the historical use of juries. The SEC’s action, involving allegations of private misconduct (fraud) and seeking punitive penalties, was categorized as a matter concerning private rights.
• Historical Precedent and Legislative Intent. The Court considered the historical contexts in which the public rights exception was applied, namely to customs duties, public land disputes, and certain government benefits, and stated that these cases typically involve legislative or sovereign functions or statutory schemes that by their very nature are governmental in character. Conversely, securities fraud is concerned with private dealings and harm to private investors.
• Jury Trial Precedents in Comparable Circumstances. The Court relied on cases like Granfinanciera, S.A. v. Nordberg and Tull v. United States to mandate the need for a jury trial when statutory actions have elements and features of common law actions, particularly when punitive measures are pursued.

Paradigm Shift in Power

SEC v. Jarkesy raises important questions about the future of the SEC’s administrative proceedings in general, and particularly those that do not involve fraud or seek civil penalties. Along with other recent decisions of the Supreme Court in Ohio v. EPA and Loper Bright Enterprises v. Raimondo, these decisions suggest a transfer of powers by paradigm shift, from the executive branch to the judiciary and, more specifically, to the Supreme Court.

Furthermore, the Loper Bright Enterprises v. Raimondo case saw a significant shift in approach, with the “Chevron Doctrine” being removed. This suggests a reduction in deference to administrative agencies like the SEC when interpreting ambiguous legislation. It also indicates a more rigorous level of judicial review for agency decisions, which could have a significant impact on securities regulation enforcement in general.

For example, the Dodd-Frank Act contains what has been dubbed the “Volcker Rule”, which prohibits banks from making certain types of speculative investments that are not in the best interest of their clients. Previously, some regulatory agencies, including the SEC, had the ability to have discretion in interpreting and changing the details of these prohibitions to ensure they remain relevant for current financial markets and practices. But with the power of fine-tuning vested in the SEC, these investment restrictions began to be redrawn afresh with the new judicial posture invoked. This may even result in a scaling back or rigorous implication of such regulatory frameworks, impacting their flexibility within which these banks are supposed to avert risks and set an innovative financial strategy.

Additionally, these decisions reflect a broader skepticism about the “administrative state” and its power. The weakening of deference toward administrative agencies could result in a significant increase in litigation, as decisions previously left to expertise-heavy agencies will now be subject to greater judicial scrutiny. This could significantly impact the workload of the federal courts and provide an opportunity for legal professionals at a time when litigation is expected to increase.

Logic suggests that under these changes, there could be increased judicial scrutiny and control over regulatory actions; nonetheless, there is no assurance that outcomes will evidence any improvement over those produced by agency expertise. A change of this nature can fundamentally alter not only the ways in which regulatory practice takes place but also the meaning given to laws within a wide variety of areas.