How to Maximize Your Minority Rights in Small-Scale Private Equity Investments

Even if you consider yourself a small-scale investor in private companies relative to today’s private equity giants, you should seek certain basic minority rights to protect your investment and enhance your exit opportunities.  In fact, most minority protections that a small-scale investor should seek are exactly the same as those that any larger PE fund would require.

Among my clients, these small-scale private equity investments generally range from $100,000-$3,000,000 for purchases of 10%-30% of a company’s outstanding equity.  They may be investments in corporations or limited liability companies (LLCs).

Here is an overview of rights you should consider:

  1. Preferred Equity.  The preferred stock (corporation) or preferred membership interests (LLC) may have any or all of three elements to help compensate you for placing your capital at risk:
    • A preferred right to dividends or distributions, which should be coupled with a tax distribution clause in an LLC;
    • A liquidation preference, giving you the right to be paid prior to other investors upon a dissolution or sale of the company or its assets; and
    • a right to convert into common equity if the common’s value would be higher than the value of the preferred in a change in control transaction.
  2. Preemptive Rights; Anti-Dilution Protection. A preemptive right is the right to acquire your pro rata share of any new securities issued after the date of your investment, which is self-help protection against dilution.  Preemptive rights may also be coupled with anti-dilution protection, allowing you to receive additional equity if securities are issued below the per unit price you paid for your equity.
  3. Board Appointment. The right to appoint a member of the board of directors (corporation) or board of managers (LLC) gives you a seat at the table at board meetings and the right to vote on board matters.  If board appointment rights cannot be negotiated, you could seek to appoint a non-voting board observer to attend meetings.  Your director/manager should receive at least the same indemnification benefits as other directors.
  4. Veto on Material Transactions.  You should seek a veto over company actions that could materially and adversely affect your investment, such as:
    • Bankruptcy or other liquidation or winding-up;
    • Acquisitions of equity or debt securities or assets;
    • Mergers, consolidations, conversions, or reorganizations of the company;
    • Sales of substantially all of the company’s assets;
    • Formation of subsidiaries;
    • Amendments to governing documents;
    • Transactions with affiliates;
    • Incurrence of debt or expenditures above a certain limit;
    • Termination of key employees; and
    • Changes in board size or composition.
  5. Financial Reports. Quarterly and annual financial reporting may be required, as well as audited financials in certain cases. If the investment is in an LLC, annual tax reports should also be provided to enable you to timely file Form 1065 K-1.
  6. Warrant/Option Rights. The warrant or option is a useful tool for mitigating risk while retaining upside opportunity.  Depending on the terms, a warrant or option can allow you to increase your investment incrementally during an agreed exercise period at the same price and the same valuation associated with the original investment.  This reduces your downside risk if the company fails to perform as anticipated and helps preserve your upside.
  7. Right of First Offer (ROFO).  A ROFO requires an equity holder who receives a third party offer for the purchase of his units to first offer to the other equity holders the right to purchase their pro rata portion of the seller’s units on the same terms as those offered by the third party.  The ROFO can enable you to increase your equity ownership by purchasing the equity of others, which is particularly beneficial if the company’s prospects are favorable and you are able to capitalize on distressed sales by other equity holders.
  8. Exit Rights.  There are several different types of valuable exit rights, a few of which are described below:
    • Tag-Along.  The corollary to the right of first offer is the tag-along right, which gives you the right to “tag-along” on a unit sale by a selling equity holder to a third party on the same terms as those given to the selling equity holder.
    • Drag-Along.  The drag-along right allows a group of equity holders (usually a supermajority) to require all equity holders to participate in a sale of company equity or assets.  If you, as the minority investor, do not wish to be made subject to the tyranny of the supermajority in a drag-along provision, you could negotiate for an appraisal mechanism requiring determination of the fair market value of the equity proposed to be transferred as a condition to the supermajority’s exercise of its drag-along rights. If the appraisal determines that the actual fair market value is greater than the proposed drag-along sale value, you would have the right to retain your equity.
    • Right to Cause a Liquidity Event. You may wish to negotiate the right to obligate the board and shareholders to pursue a sale of company equity or assets the company fails to achieve certain pre-determined milestones.

Top 9 Warning Signs in a Business Deal

One of the benefits of being a corporate lawyer is the opportunity to participate in a variety of interesting deals.  In these, you encounter a motley crew of characters.  You witness a range of negotiating styles and tactics, and learn which are effective and which are not. You see some ventures succeed and many others fail.

In the great theatre of the deal, there are rare moments in which something may not feel right to the lawyer or the client about a proposed business transaction or partner.  The thing amiss may only be verifiable by circumstantial evidence.  To paraphrase the Delaware Chancery Court, it may be that the circumstances surrounding the person or transaction stink bad enough that they simply do not pass the “smell test“.

Questions may arise following diligence on the target (which should minimally include Google and litigation searches), from a person’s conduct in negotiation or from other third party sources.  There will not typically be any proverbial smoking gun, so your judgment and careful diligence will be your guiding light.

In my years as a deal lawyer, the appearance of any of these nine elements (not in any order of priority) has been a fairly reliable harbinger of difficulty, dishonesty or even fraud in proposed business deals.  If any of these elements arise in your dealings, you should consider diving deeper into diligence to determine if there is genuine cause for concern or possibly re-negotiate or abandon the deal altogether.

  1. The demanding long-winded negotiator of trivial things.  Excessive demands for non-substantive or patently unreasonable changes to the initial non-binding deal document, such as the term sheet or letter of intent, may foreshadow protracted and possibly agonizing negotiation of the definitive agreements and a challenging ongoing business relationship.  If the demands are coupled with the party’s long-winded or repetitive arguments why he is right and you are wrong (or other ridiculous anectdotes), they may suggest personality issues.  In my experience, character defects are not easily remedied and often worsen with time. The unreasonable negotiator should distinguished from the tough savvy negotiator, who requests substantive deal points but is often reasonable and a good business partner after the deal is papered.
  2. The deal requires urgent participation and won’t be available after “X” occurs.  This is the classic illusion of scarcity tactic.  If your prospective business partner claims that if you fail to act now, (i) a large investment from Mrs. “Y” will soon be received and the price of the investment will increase or (ii) the deal will not be available for “Z” reason, the claim may be a red herring and should be carefully scrutinized.  Fictional future money is sometimes characterized as coming from abroad or from some well-known person with whom the partner purports to have a close relationship.
  3. The secrets that cannot be revealed.  If the target’s founder or your prospective partner is unwilling to reveal certain fundamental aspects of the business or how it expects to make money, the company may not have a business plan.  You have a right to know the company’s business model and growth strategy, with the understanding that the model will likely evolve over time. In one startup deal I reviewed for a client, the founder made repeated excuses why he could not provide information about critical company inventions and provisional patent applications.  Later diligence revealed that the company had no inventions and its business plan was impracticable. After spending the other investors’ money, the founder abandoned the company and the U.S.  This is akin to Bernie Madoff’s “black box” investment strategy that was “so good” that it could not be understood or replicated by any reputable investor.
  4. The anonymous “big money” partner.  Any person who must remain anonymous is often a red flag, particularly if this mystery man is a primary financing source.  A client once instructed me to prepare the draft documents for a “big investment by a Chinese investor who needs to remain anonymous.”  A third party had informed the client that the Chinese wanted this, that, and the other, and I prepared several draft iterations at the client’s request.  The Chinese investment never materialized and the client wasted money on legal fees. Some celebrities and others have genuine reasons to protect their privacy, but if you are doing a deal with someone (including a celebrity), you have a right to know their identity and to size them up.  Always insist upon lifting the veil of anyone who says they must remain anonymous.
  5. The shell company spider web.  Domestic and offshore entities are often formed to execute lawful business strategies, including liability and tax mitigation, particularly for companies with substantial non-U.S. source income.  But as the Panama Papers confirmed, offshore shells with limited assets may also be created for tax evasion and other corrupt purposes.  Before doing any deal with a company that owns or operates affiliates, especially offshore shell entities, you should fully understand the organization chart and confirm that each entity exists for lawful and legitimate purposes.
  6. The paperless office.  It is fine if your partner keeps a clean desk and operates in the cloud, but a lack of paperwork memorializing a business’s structure, assets and operations is almost invariably a red flag.  You should have access to reasonable diligence paperwork and you should be able to freely ask questions and to have them answered.
  7. No skin in the game.  If the deal does not require your business partner to put money or something else of value into the deal, your interests may be de-aligned from the beginning.  In the startup context, this could be the situation where a founder’s shares are fully vested from day one and he has no invested capital or other hook to prevent him from walking away when the going gets tough or he receives a better offer.  In a joint venture, it could be the ability of a party to enrich himself at the expense of the venture.  De-alignment can usually be remedied by careful drafting of the legal incentives in the deal documents.
  8. The promise of abnormally high or guaranteed returns. This trick is as old as prostitution: returns above market rates or guaranteed returns on invested capital are often signs of a Ponzi scheme, where the prompter lures you to invest to pay his prior investors rather than to make bona fide investments with you money. You should always determine the source of returns and whether that source is capable of generating the projected payout.  Most financial projections are exactly that, and vary dramatically from actual results.  There is no such thing as a guaranteed return.
  9. It sounds too good to be true.  This is a corollary of abnormally high returns.  As the adage goes, if what you are to receive in exchange for your participation sounds too good to be true, then it probably is.  In most of these cases, you should run away from these deal absent a reasonable and verifiable justification for its sweetness.