The role of venture capital securities in entrepreneurship

The role of venture capital securities in entrepreneurship

For entrepreneurs to flourish, they need funding: venture capital is financial capital provided to early-stage, high-potential, high-risk, growing entrepreneurial companies. Venture capital is particularly attractive for new companies with a limited operating history that are too small to raise capital in the public markets, and have not reached the point where they are able to secure a bank loan or complete a debt offering. In exchange for the high risk that venture capitalists (VCs) shoulder by investing in smaller and less mature companies, venture capitalists usually get a significant portion of the company's ownership (and consequently their value).

Once a VC decides to invest in a venture, the involved parties need to settle on a deal structure. When negotiating the deal structure, parties need to keep a few considerations in mind:

  • The deal structure needs to protect the VC against losses and should encourage entrepreneurs to work hard to make the venture a success.
  • Most VC investments are illiquid, which means that unlike shares of listed companies, they cannot be sold very easily.
  • Finally, most investments are characterized by asymmetric information. In general, the entrepreneur knows more about the venture than the investor.

VCs typically use convertible preferred equity to finance ventures. As the name suggests there are two important features of these securities: conversion and preferred.  Investors of convertible preferred equity have the option of either holding a debt-like claim -preferred equity or converting into common equity. Converting into common equity implies sharing ownership in the venture with the entrepreneur. Preferred terms make it similar to a loan (debt), gives holders a right to interest payment (dividends) and additionally gives preference in payments over common equity. In other words, the preferred feature ensures that preferred investors are paid before common equity holders. In a typical deal, VCs would hold preferred equity and the entrepreneur common equity, thus the VC can get paid before the entrepreneur if the venture does not do well. However, if the venture succeeds and its value increases, the VC would convert the preferred equity into common equity and share the fruits of this success with the entrepreneur.

Another feature of VC investments is that they are done in stages. VCs would never provide all the capital upfront to a venture; instead, they would only provide sufficient capital to reach the next milestone. Once the capital has been used up, the entrepreneur has to raise another round of financing to reach the next milestone. The advantage of staging is that VCs can stop financing if the venture is not doing well. It can also be advantageous for the entrepreneur, as the terms can be made more favorable to them if their venture is successful. Staging also helps reconcile the aforementioned asymmetric information levels between entrepreneurs and VCs, since future investments are only made based on past outcomes.

Finally, in addition to providing capital, VCs also monitor and guide the venture. The structure of most deals is designed to ensure the monitoring role of VCs. While VCs do not hold the majority of shares, they would have the right to nominate members to the board of directors. These rights help the VC monitor progress and guide the venture and gives them the power to replace managers if operations are not going smoothly.

Having discussed the general features of VC investments, we will now explore details of some specific securities used in VC contracting. It must be noted that convertible preferred securities come in various flavors. Dr. Arcot analyzes one such security called participating convertible preferred security (PCP), used widely in venture capital contracts (Arcot, 2014). Participating convertible preferred stock gives its holders the right to be paid first (before common shareholders generally held by the entrepreneurs) and at the same time, allows them to participate in excess earnings (i.e., the cash flow after all debt and preferred claims have been satisfied) along with the common stockholder. PCP holders thus concurrently hold both a debt-like claim (preferred equity) as well as an equity claim (participation rights). However, PCP holders lose their preferred rights if they convert this PCP stock into common stock. His research explores why venture capitalists are willing to convert their PCP stock into common equity and give up their preferred rights.

He proposes a signaling model for PCP stock based on its role in venture capital exits. The two major forms of exits observed in venture capital are the initial public offerings (IPOs) and the trade sale. IPOs are exits where shares of the venture are sold to investors and then listed on the stock market and trade sale is a transaction in which a venture is sold to another company.  Typically, a PCP stake is converted into common equity during an IPO exit, but is not converted in a trade sale exit. The model shows that VCs can signal the quality of their venture in an IPO by converting their PCP stake into common equity and giving up some of their cash flow rights. By giving up something during an IPO, VCs are signaling to investors that the venture is of a high quality.  Signaling is of particular importance in an IPO, because in an IPO shares are sold to new investors who do not have access to documents to analyze the venture’s performance. Investors in an IPO typically have to rely on a bank to perform the due diligence and hence are thus relatively uninformed about the venture. In contrast, potential trade buyers are given access to documents, which they can analyze to reach conclusions about the venture’s quality. Since trade buyers typically come from the same industry as the venture, they are likely to have industry knowledge and are better equipped to interpret the information provided.

When exit is through an IPO, the entrepreneur retains control of the firm. Thus, when the firm value is high, an IPO exit rewards the entrepreneur and should be the preferred exit route. However, the VC may be reluctant to take that route, given that investors in an IPO are less informed and the VC may not get the full value for his stake. When the firm value is high, the VCs may prefer to target investors who are more informed and get a higher value for their stake. In other words, exit through a trade sale. However, the interests of VCs and entrepreneurs are more easily aligned when the VCs convert their PCP stakes into common shares and exit through an IPO.

Venture capitalists investing in start-ups use sophisticated financial instruments to structure their investments. This article provides a rationale for the use of one such instrument, PCP stock, based on the venture capitalist’s exit strategy. In doing so, it makes a connection between the exit route and entrepreneurial effort. This highlights factors that have direct implications for the incentives of venture capitalists to invest in ventures and entrepreneurs to exert effort to make them a success.


Arcot, S. (2014). Participating convertible preferred stock in venture capital exits. Journal of Business Venturing, 29(1), 72-87.

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