Private investments in venture and early-stage companies are characterized by their potential for positive asymmetrical outcomes (PAO). The risk of losing the entire investment is offset against the potential for high-multiple ROIs. But asymmetric outcomes refers to more than the non-linear relationship between risk and return…it also refers to the appeal of investments where multiple liquidity and exit outcomes are possible.

This is often referred to as optionality…current knowledge of the potential for multiple future outcomes.

According to his book, In an Uncertain World, Robert Rubin, the nine-figure alumni chairman of Citi, is said to have developed his appreciation of optionality in his prior days of risk arbitrage at Goldman. While practicing risk arbitrage, Rubin developed a penchant for optionality (keeping ones options open) and avoidance of a mindset that restricted decision-making to binary and zero-sum outcomes.

It is believed that Larry Summers ultimately coined the phrase “preserving optionality” back when he was deputy secretary of the treasury under Robert Rubin in the Clinton administration. It was meant to describe a strategy of keeping options open and fluid, before all of the uncertainties have been resolved in dynamic environments where there is a high likelihood for the emergence of new and material information.

The phrase is relevant in venture circles for investors, as well as, entrepreneurs.

Preserving Optionality for Investors and Entrepreneurs

For entrepreneurs, optionality in rapidly evolving scenarios (such as a start-up) means leveraging real-time data and experience before making important decisions that are either resource intensive or cannot be easily reverse…such as pursuing a market vertical, developing a new technology or application, embarking on a joint venture or contemplating multiple exit strategies.

In most instances these options were not conceivable at the outset of the venture because, at best, a start-up’s business plan is to an entrepreneur what a treatment is to a script writer…it’s simply a first draft. It is the actual, real-time development of the story line and its characters that ultimately determines the final draft of a movie script…or the path to monetization for a new business venture.

Investors and experienced entrepreneurs know this. I have rarely seen a startup that successfully monetized itself based upon the mission, objectives and milestones envisioned in its original business plan. That’s because time in the market is often more valuable than time to market with respect to improving the quality of the critical decisions that are of material consequence.

Technology consultant Sean Hull of the Heavyweight Internet Group notes this nuance…“preserving optionality is a philosophy that takes some getting used to. It involves having a sense of humor, and realizing our own human limitations.”

Author-epistemologist-investor Nassim Taleb gets it as well. In Fooled by Randomness he characteristically opines “people overestimate their knowledge and underestimate the probability of their being wrong“. He suggests that by being ever aware of our limitations of prescience, and keeping our eyes and our options open, we can make better, more educated, and lower risk decisions. He is correct.

This implications and realities of preserving optionality, often positions entrepreneurs at odds with investors. The interests of optionality must be balanced.

For the entrepreneur, preserving optionality is an interest that frequently requires a balancing act against intrusive, non-strategic, no-value-add investors who view accountability and measurability as metrics preeminent to the benefits of prudent executive flexibility and strategic discretion.

On the other hand, the investor’s needs for optionality is particularly relevant today in light of the macro market malaise and minimal marquis exits. With venture-backed IPOs now more an exception, venture investors need to stipulate optionality with respect to cash-flow and exit rights as a contingency to their investment commitment.

Investors need to see visibility to alternative liquidity events such as dividend distributions or return of initial capital beyond the sale or merger of the company or its assets, or a less than likely IPO.

It is of no surprise that investors have a preference for positively-skewed outcomes and hold an aversion to negatively-skewed outcomes despite the fact that linear or variance-based risk measures generally weigh the outcomes equally.

Yet, investors seeking the potential for multiple and positive asymmetric outcomes on their commitments must also apply the measures of asymmetry and optionality to their deal diligence and terms. More than ever, investors should require visibility on multiple paths to liquidity. The investor has the responsibility to appropriately balance their interest in ROI with the survival or expansion cash-flow needs of the portfolio company.

Why so many “professional” investors are so passive on this issue is puzzling.

Investors and entrepreneurs alike both benefit from preserving optionality and having the pre-negotiated discretion to pursue a prudent Plan B.

We will discuss those some of those options in upcoming posts.

Album:   Balance & Options, DJ Quik, 2000

The Black Swan by Nicholas Nassim Taleb holds its own among the most important investment books ever written. In it, Taleb argues persuasively that any sensible long-term strategy in a world dominated by extreme and unpredictable (black swan) events has to accept, and even embrace, that very unpredictability. It is poignant and timely advice for any investor and a must-read for investment professionals.

I met Taleb for lunch at Bice in NYC one afternoon about three years ago while I was heading Alternative Strategies for an investment management firm. I was interested in exploring the idea to engage Taleb as a sub-advisor for an investment fund that we were contemplating. I found him to be personable, enthusiastic, engaging and surprisingly modest.

I had read and re-read Fooled by Randomness: The Hidden Role of Chance in the Markets and in Life before our meeting and I was looking forward to discussing his contempt for investment managers that sell themselves on their track record…a cynicism that I shared. But Taleb had just finished his final draft manuscript of The Black Swan and directed our discussion towards his treatise on asymmetric outcomes-the central theme of the unpublished tome that he brought along with him and referenced throughout our visit.

The notion of asymmetric outcomes, “I will never know the unknown since by definition it is unknown. However, I can always guess how it may affect me, and I should base my decisions around that”, causes Taleb to advise to seek out (investment) situations “where favorable consequences are much larger than unfavorable ones.”

That is a central tenet of Venture Populism and my advocacy of committing a portion of an investor’s portfolio to private venture-oriented investments. Like Taleb, I believe that effective investment portfolios should contain meaningful (and appropriate) exposure to positive Black Swans-such as private equity investments in emerging ventures and distressed companies.

In posts to come I will expand on this premise and propose a provocative new model for portfolio construction that balances the investor’s need to mitigate the asset-depleting impact of negative black swan events with simultaneous allocations that benefit from the potential of positive Black Swans and asymmetrical outcomes.

Many advisors now concede that Modern Portfolio Theory, traditional asset-allocation and buy-and-hold investing models have failed and investors are looking for improved approaches that preserve capital and manage unexpected risks more effectively without giving up on the prospects for capital appreciation.

The Black Swan is indeed a brilliant and provocative work. As the New York Times review summed, “It concerns the occurrence of the improbable, the power of rare events and the author’s lament that in spite of the empirical record we continue to project into the future as if we were good at it.”

We expect all swans to be white and are shocked when a black swan swims by…the same way that we were lulled into complacency with flawed risk management models and were then shocked when the market fell 50% and erased away trillions of wealth.

Investors and their advisors can build better portfolios that are for the most part insulated from the impact of negative black swan events, yet have simultaneous exposure to asymmetrical risk/return opportunities.

Album:   The Black Swan, Story of The Year, 2008

In prior posts I have taken swipes at traditional asset allocation, buy-and-hold investing, the Efficient Frontier, the Efficient Market Hypothesis and Modern Portfolio Theory (MPT).

Sure, I am trying to be provocative, poke a little at advisor complacency and provoke polemic on the comment boards…but I am also sincere. MPT relies entirely on investment history for investment analysis and conclusions. These tired and discredited methods are rubbish…and have cost investors trillions.

It is encouraging to see evidence of advisor post-mortems in progress as some advisors are seeking not to repeat the mistakes of the past. I was also entertained by John C. who cracked on the comment board, “What’s over 50 years old and still considered modern?   MPT”

But pretty pie charts and Powerpoints are not so easily disposed of. As an anonymous critic incites, “The appeal of Modern Portfolio Theory in the investment advising community is its simplicity, graphic presentation value, and most of all, little or no investing judgment or skill is required; just pick, print, present, and hope; chasing efficient frontiers, hoping that investment history will somehow repeat itself, and just waiting for historical updates to generate new efficient frontiers to justify investment change.”

Nevertheless, some advisors are stubbornly standing by their man(tra).

Modern Lovers

Consider these edited comments that I received from Matthew K. in response to the Crisis = Opportunity post;

“MPT works. With the right allocation and systematic rebalancing to maintain percentages as well as in line with client’s goals, there is no lost decade. Markowitz knew what he was doing, and as an academic, he did not stand to profit…When MPT is juxtaposed with Daniel Kahneman’s Nobel Prize winning ideas on heuristics, you see how MPT does add value when used in line with client’s goals…Any classic definition of “Venture” includes the idea of risk taking. Where does that fit in CAPM or the efficient frontier?”

I cannot rebut a hopeless romantic, so let’s engage Matthew K. in a virtual volley with interlaced quotes excerpted from a FT article and a McKinsey interview with the especial epistemologist, Nassim Nicholas Taleb. Taleb is the author of two true investor instant classics and must-reads, Fooled By Randomnes and The Black Swan.

Taleb has a strong opinion on the matter of MPT and modern finance…and he is no modern lover:

MK- MPT works. With the right allocation and systematic rebalancing to maintain percentages as well as in line with client’s goals, there is no lost decade.

NNT-We learn from crisis to crisis that MPT has the empirical and scientific validity of astrology, without the aesthetics…In 1990 William Sharpe and Harry Markowitz won the prize three years after the stock market crash of1987, an event that, if anything, completely demolished the laureates’ ideas on portfolio construction….I would ban portfolio theory immediately. It’s what caused the problems…Portfolio theory simply doesn’t work. It uses metrics like variance to describe risk, while most real risk comes from a single observation, so variance is a volatility that doesn’t really describe the risk. It’s very foolish to use variance.

MK-Markowitz knew what he was doing, and as an academic, he did not stand to profit…When MPT is juxtaposed with Daniel Kahneman’s Nobel Prize winning ideas on heuristics, you see how MPT does add value when used in line with client’s goals.

NNT-Academic economists are no more self-serving than other professions. You should blame those in the real world who give them the means to be taken seriously: those awarding that “Nobel” prize… Every time I have questioned these methods I have been abruptly countered with: “they have the Nobel”, which I have found impossible to argue with. There are even practitioner associations such as the International Association of Financial Engineers partaking of the cover-up and promoting this pseudoscience among financial institutions. The knowledge and risk awareness we are accumulating from the current subprime crisis and its aftermath will most certainly not make it to business schools.

Thanks, (virtual) Nassim. I will take the next one.

MK-Any classic definition of “Venture” includes the idea of risk taking. Where does that fit in CAPM or the efficient frontier?

VP-Of course, venture implies risk-taking… they are nearly synonymous. A venture investor is knowingly acknowledging and accepting an implicit and quantifiable serving of risk that is decidedly less than a range of positive (asymmetric return) outcomes. Perhaps investors would have been better served if their notion of the risk that they were assuming in their efficient frontiers was not muted (and implied to be mitigated) by the marketing machinations of MPT. CAPM is a future-oriented model yet it essentially relies on historic data to predict future returns. The Efficient Frontier? I have seen the inputs, I have seen the outputs…and I have seen the results…the efficient devastation of unsuspecting portfolios.

Album:   The Modern Lovers, The Modern Lovers, 1976