Angel and venture investors in startups and early-stage companies frequently have the option to determine the extent to which they intend to contribute intellectual capital, beyond their financial commitments. “Value-added” private venture investors often lend their business skills, resources and rolodex to their interests, helping the company solve tough problems, prioritize objectives, build a great team and even seek out strategic partners and potential customers.

Equally compelling to private venture investors is the ability to influence the terms of engagement of their capital in a manner that increases the opportunity for a favorable investment outcome. Unlike conventional public investment vehicles and most alternative products such as hedge funds, the investment terms for private venture investments are generally negotiable…depending on the size of the contemplated investment and stage of the company and the funding history.

Evaluate—Negotiate–Allocate

Between due diligence and the investment decision is the opportunity to influence and negotiate investment terms in a manner that increases the probability of a positive asymmetric outcome. It surprises me when angel allocators, particularly lead investors in a seed round, simply accept the offering terms of a private venture without fully leveraging their currency to negotiate the best deal for their capital. Startup capital for new ventures is scarce today relative to the halcyon days of the 1990’s. That tilts the advantage in favor of capital and provides early-stage venture investors with an opportunity to materially improve upon their position.

Angel round investors are a unique breed. They take on startups at the riskier seed stage (in pursuit of higher-multiple exits) at a point where venture capital firms will typically not engage. VCs and institutional investors are more apt to require some evidence of progress with a startup…whether with regards to financing, product development, a proven business model or market traction. Yet that does not prevent VCs from coming to the table with their own terms for a Series A financing.

On the other hand, angels too often let the entrepreneur set the terms for the seed and bridge financing rounds.

So, which provisions in an angel round’s term sheet are generally negotiable? All of them.

I am humored by entrepreneurs who describe their terms as being “market”. Because there is no market without the angel’s capital, and that means that valuation, liquidation preference, anti-dilution protection, dividends, various protective provisions, board composition and even the vesting of the founder’s stock can and often should be subject to negotiation…particularly in a smaller financing round.

Each of these terms may have a critical influence on the outcome of an early-stage investment, but valuation is arguably the most difficult for angel investors to negotiate as there is little meaningful company history to assess…rather, merely a vision around an idea, a market and a management team, and perhaps a business plan.

The “market” (of angel investors and entrepreneurs) has responded to this quandary by predominantly relying upon Convertible Notes to fund seed-stage companies. Rather than dickering endlessly about the present value of a future uncertainty, angels and entrepreneurs agree to lend their capital to the new venture in the form of a note (often secured with some form of collateral and offering a dividend) and agree to convert their debt to equity at the price set in the subsequent round of financing.

The theory is at that point in the future, much more will be known about the business, market, competition and opportunity and that it will be easier to agree on a valuation.

Consequently, Convertible Notes have become the primary template for seeding young companies and providing “bridge” financing from the concept stage to a larger, subsequent financing round.

Early-stage investors should engage the growing universe of online content that speaks to best practices, suggested deal terms and negotiation tips for investors in early-stage ventures. Most critically, tyro angels should engage a securities attorney with ample experience in private venture financings to advise them on term sheet negotiation.

In Woody Alan’s 1994 crime-comedy Bullets Over Broadway, the gangster-financier played by Chazz Palminteri exploited his angel status by casting his girlfriend in a lead role and rewriting the play’s script.

In early-stage financings artful angels should always consider opportunities to leverage their currency to rewrite the script of the bridge note and positively influence their investment’s ultimate optionality and outcome.

Album:   Script of the Bridge, The Chameleons, 1983

In short-sighted efforts to convey the accrued wisdom and tenets of their craft, venture investors occasionally declare their due diligence dogmas by way of the fallacy of false dilemma…a distorted line of reasoning where an outcome must be the result of either of two options. Often referred to as “black and white reasoning”, a false choice is offered up between two scenarios when in fact many more scenarios are probable.

Our false dilemma du jour is; which venture investment in a startup is positioned for a better outcome…the “A” idea with a “B” management team, or the A team with the B idea?

[Of course, it is never this simple, as the query ignores other critical items such as market size and maturity, competition, barriers to entry and of course, deal terms…but let’s play along…]

I opt in favor of the A team with the B idea. The B team may not be able to execute on the A idea, but I have seen many A teams successfully monetize B (and C) ideas.

I would postulate that the majority of angel and venture investors concur on the acute importance of the quality of the team engaged to execute a new venture’s business plan. But I diverge from the consensus when that same conventional wisdom subsequently surmises that the A team’s commitment is not validated unless those “founders” have contributed a material amount of their own personal financial assets to the venture.

The notion of a founder’s cash as an indication of their “skin-in the-game” ranks among the myriad of myopic and misplaced myths of venture investing. It is derivative of another false dilemma fallacy that evaluates the involved vs. the committed startup founder by pitting the pig against the chicken as the sources of a traditional bacon and eggs breakfast. (The pig has truly “committed” by providing the bacon, while the chicken is merely “involved” in providing the eggs.)

I recently attended the road show where an ambitious retail venture (redundant, eh?) was presented by a genuine A team of co-founders comprised of a young entrepreneur and a seasoned C-level executive CEO. It only took a few minutes into Q&A for an experienced institutional investor to impugn the initiative by inquiring about the absence of co-founders capital committed to the enterprise.

In this particular instance, the young entrepreneur was early in his career with a very young family and simply lacked the personal financial resources to allocate any capital to his vision. On the other hand, the seasoned 60-year old CEO walked away from a prestigious C-level position where he enjoyed a high six-figure compensation from a venerable multi-national concern at the peak of his career to take a flyer on a yet-to-be-financed retail startup…during a recession.

It is certainly appropriate to question a founder’s commitment as long as the answer is evaluated in its appropriate context. The CEO was “all-in” career-wise and the young founder had the chops, but lacked the bacon to commit to the plate.

Considering founder’s personal financial assets to be prerequisite skin-in-the-game simply ignores the lessons of ventures past. Steve Jobs was 21 when he founded Apple and his partner Steve Wozniak was 26. Gates and Allen were 20 and 21, respectively. Google founders Page and Brin were both 25. Hewett and Packard were 26 and 27 and Michael Dell was merely 19.

None of these extraordinarily successful founders had any meaningful cash to invest in their own startups. If they did, angel and professional venture capital investors would have been deprived of billions of dollars in long-term capital gains and carried interest.

Of course if a founder has a material amount of personal financial assets—it is appropriate for an investor to expect those funds to be committed to the venture. Moreover, it is prudent for the founder to use proprietary resources as it enables him to ultimately preserve more equity in his enterprise. But, career risks, opportunity costs and reputational risks can be far more consequential to a founder than losing several dollars or pounds of flesh.

In fact, our only 100% write-off in this decade was an investment in a serial internet entrepreneur who already had committed $13 million of his own funds to the startup.  He had the bacon, but not the chops or experience to execute in the specific sector. The ensuing high-profile strikeout subsequently insured that the failed venture would be the entrepreneur’s final turn at bat, as he was no longer considered bankable.

Before you judge a venture based on a founder’s capital as skin-in-the-game, make certain that you fully understand the emotional commitment, as well as, the actual impact that the demise of the startup will have on the founders. A skin tight founder is not, by itself, a reason to walk away.

Album:   Skin Tight, Ohio Players, 1974

In our previous post (Let It Be) we noted that Senator Chris Dodd’s financial reform bill that is on the way to the House floor contains new provisions that would reduce the number of individual eligible to invest in private ventures. The original draft of the bill would increase the $1 million net worth threshold that defines an “accredited investor”, which in turn determines an individual’s eligibility to invest in exempted private securities offerings under Regulation D of the 1933 Securities Act.

These Reg D offerings enable startup businesses access to “angel” capital — the critical means of finance for early-stage ventures that could not otherwise bear the prohibitive costs and regulatory burdens of SEC registration.

The angel investor and entrepreneurial community responded vociferously against the proposed legislation citing the chilling impact that an estimated 77% reduction in the ranks of accredited investors (per Bloomberg BusinessWeek’s estimate) would have on angel investment, financing startups, new job creation and reviving the reliable stalwart of economic growth—the small business sector.

Now we hear that the Angel Capital Association announced that Dodd and his Senate Banking Committee have drafted amendments to the initial proposal whereby the threshold for “accredited investor” would stay the same, although the standard for net worth of $1 million would be revised to exclude the investor’s primary residence.

The ACA has proclaimed that although “we would have preferred no adjustment to the standard for angel investors, we believe this is a good compromise” adding that the amendments “improve the bill so that it balances the importance of small business capital formation while protecting angels and other types of private investors from securities law violators.”

What bunk. The ACA should be opposing such compromising compromises. The opportunity to make a private investment in a private venture should be every investor’s right. The ability to invest in a new business should not be an exclusive privilege bestowed by politicians upon persons of a certain economic class.

Moreover, there are ample investor protections already in place. The SEC’s powerful Rule 10b-5 is all about protecting investors, and it applies to private investors just as it applies to the general public. Every state has securities laws on the books that protect private investors from fraud. Indeed, the registration requirements of the 1933 Act also serve that protection purpose.

As explained by SEC alumnus Patrick Daugherty of Foley & Lardner, “Regulation D is an exemption from those registration requirements. It’s part of our law precisely because there exists a class of investors who can ‘fend for themselves,’ in the words of the Supreme Court’s venerable Ralston Purina holding. Congress, the SEC and the Supreme Court have believed for fifty years that offerings limited to investors who are ‘rich and smart’ about finance need not be registered.” 

Although there is no doubt that the majority of frauds have occurred in highly regulated or visible investment schemes (remember Refco, Enron, Worldcom), there is ample history of unscrupulous brokers, dealers, issuers and promoters abusing Reg D and defrauding investors. The SECs recent indictment of Provident Royalties, LLC for a massive $485 million ponzi scheme is a good example of how the SEC’s limited resources could be effectively allocated away from surfing porn on the web.

But I have never heard a cogent argument that supports the notion that any individual should be restricted from the opportunity to invest in a startup or new business venture that has appropriately disclosed the risk of failure and loss of all capital that is inherent to venture investment.

Private venture investment in startup and early-stage businesses should be entirely exempt from the Reg D accredited investor provisions.

Angel investors know the risks are high and that a significant portion, if not the majority of their venture investments will fail. There is absolutely no evidence that angels investing in startups played any role whatsoever in the recent financial crisis that has prompted Dodd’s proposed reform bill. So, who does this compromise “protect”?

The notion that net worth is an effective indication of an individual investor’s sophistication or ability to bear the risk of loss is laughable. The bright-line standard used to ascertain an investor’s sophistication is ironically unsophisticated and utterly under-inclusive.

I align with Richard Rahn, chairman of the Institute for Global Economic Growth that “the rule makes little sense and strongly discriminates against knowledgeable people who are not yet wealthy but are quite capable of making good investment decisions.” Rahn refers to this as “financial fascism”.

In this connection, there is no reason to suppose that investors who are millionaires only after including home equity are unable to fend for themselves while those who are millionaires exclusive of home equity are self-reliant. Consider Sid and Nancy. Sid has $500,000 in financial assets and a $1 million home with no mortgage. Nancy has $1.4 million in financial assets and a $1 million home with a $900,000 mortgage. Both Sid and Nancy have a net worth of $1.5 million. Sid has constructed a more-conservative balance sheet for himself. But Senator Dodd says that Sid needs federal protection while Nancy doesn’t.

This makes no sense, especially since Sid can “become accredited” simply by borrowing $500,000 against his house and investing the proceeds in securities. Does Senator Dodd really want to encourage greater mortgage borrowing as a means of facilitating private capital formation?

Does anyone really believe that an IT professional making $75K is less able to evaluate a web startup than a professional athlete? Is a recent B-school grad less able to assess the merits of a new retail business venture than a trust fund baby? Is a cook any less able to evaluate a new restaurant venture than a lottery winner with an eight grade education? Wealth is simply not an effective proxy of sophistication.

But what I find most offensive is that this “compromise” only compromises personal financial freedoms and investor’s rights and liberties…a viewpoint shared by my old friend John Mauldin, acclaimed creator and curator of commentary at investorinsights.com, a blog focused on private money management.

“Why should 99% of Americans be precluded from the same (investment) choices available to the rich? If you were to tell investors that they would be discriminated against because of their gender or race or sexual preferences, there would be an outcry….It is a matter of Choice…Equal Access…Equal Opportunity…it is time to change a system where Americans are relegated to second-class status based solely on their income and wealth.”

Nice, John. I also see that one of Canada’ top angel investors also shares our opinion that any investor should be able to make angel investments (assuming the proper disclosure of risks).
 

Regulators and politicians whom plead that such provisions protect the poor and unsophisticated from unscrupulous promoters are hollow hypocrites. Presently 42 state governments run lottery programs—a regressive tax that preys on lower-income households to the tune of more than $17 billion in 2007, the most recent annual estimate. Recently, researchers have identified a correlation between economic difficulties and the popularity of lotteries….so we are likely seeing greater lottery ticket sales today.

Single state lotteries usually have odds of about 18 million to 1, while multiple state lotteries have odds as high as 120 million to one. The state lottery and government officials know that it is a sucker’s bet that is disproportionately supported by low-income households and marketing programs make sure to advertise in lower income areas and increase television advertising when welfare and social security checks are distributed. The poor and unsophisticated are left to their own defenses when government acts as the issuer and the promoter.

Government should be encouraging private investment in new businesses which historically account for the majority of the innovation and job creation in the American economy. The Kauffman Foundation, tells us that “between 1980 and 2005, virtually all net new jobs created in the U.S. were created by firms that were 5 years old or less…That is about 40 million jobs. That means the established firms created no new net jobs during that period.”

Startups continue to be a robust and critical engine of job creation as according to Bloomberg, despite the sluggish economy some 259,480 angels invested $17.6 billion in 57,225 entrepreneurial ventures in 2009.

As the average startup employs approximately eight people, increasing the bracket for accredited investors in any manner will only make it more difficult than it already is for startup businesses to raise money and create new jobs.

To the contrary, nothing would be gained by reducing the pool of accredited investors—no additional protections to investors and no benefits to the national financial system or the economy. Private venture investment in startup and early-stage businesses should be entirely exempt from the Reg D accredited investor provisions.
 

Album: Up The Bracket, The Libertines, 2002

Senator Chris Dodd looks determined to leave his last term in office with a dubious legacy – his sponsorship of the Restoring American Financial Stability Act of 2010  which passed the Senate Banking Committee on a party-line vote  on its way to the House floor.

Dodd’s 1,336-page reform bill seeks to address the timely and substantive need to police abusive and unfair terms for mortgages and other financial products, the “systemic risks” inherent in derivatives such as credit default swaps, as well as, the use of leverage by tackling the “too big to fail” issue. Of course this comes after the barn door has been open and all the horses have fled, and many will argue that The Street will inevitably develop new instruments to challenge the new regulations and oversight…but that’s another problem.

In the over-reaching spirit of not letting a good crisis go to waste, Dodd’s bill also seeks to fix what’s not broken with provisions that asphyxiate investment in startup ventures and subsequently stifles what has historically been the most sustainable source of new job creation during a period of hopelessly high unemployment.

Dodd proposes adjusting for inflation the income and net worth requirements for a person to be considered an “accredited investor” by the SEC under the 1933 Act. If this were to occur it will materially decrease the pool of private capital that is available to finance new companies, and in turn, innovation, job creation and economic growth.

Presently, an individual must have a minimum net worth of $1 million or an annual income of $200K to be an accredited investor. Although the reform bill does not identify the proposed multiplier to adjust these numbers, it is fair to assume that an inflation adjustment approach (based on CPI) is likely which would raise the 1982 mandated $1 million dollar net worth threshold to approximately $2.25 million and the individual annual income threshold to approximately $450,000.

Applying a $450K income threshold to the latest IRS tax return data, the number of accredited investors would drop approximately 77%, from 4.5 million individuals who earned $200K or more to a little over 1 million. That’s a material decrease in the pool of available “angel” capital.

A 2008 study of accredited investors based upon data reported in the 2008 Statistical Abstract of the United States by business demographer Paul Reynolds found that only 10.5% of accredited investors had made a private venture or angel investment in the prior three years. Adjusting that data for the increased thresholds implied under the Dodd bill reduces the number of likely angel investors to between 121,000 and 174,000 individuals…devastating.

We can debate forever the wisdom behind an over-inclusive system that uses personal wealth as a proxy for investment sophistication. Yet, many others (myself included) would maintain that the accredited investor standard prevents those with adequate access to information, or experience, or due diligence skill, or sector expertise, or entrepreneurial spirit or emotional tolerance for risk to embrace the potential asymmetrical upside of private venture investment. (What would you expect from a Venture Populist?)

I agree with the recent opinion expressed on this subject by digital strategist Alex Alben in the Seattle Times…”more investors today have access to financial information and filings through electronic databases than ever before. The old notion that only wealth buys access to financial information is increasingly quaint in our digital age. The financial crisis of 2008-09 was not precipitated by millionaires losing money in private placements…the monetary amount should not be a moving target, changeable at the whim of the SEC… Both houses of Congress should pass a bill with meaningful consumer protection and bank oversight, but not harm privately funded startups in the process.”

I would also add that if the current administration is so intent on identifying the $200,000 income level as “the rich”…as those capable of taking on a greater financial burden in the form of higher taxes, shouldn’t those same individuals continue to have the right of access to private equity and venture capital transactions, the asset class that has historically delivered investors the highest returns?

Rich enough to tax should at the very least mean rich enough to invest.

Personally, I believe the accredited investor thresholds as they are applied to investments in early-stage businesses are arbitrary, under-inclusive, undemocratic, discriminatory, and unnecessarily restrict innovation, economic growth and new job creation. All individuals should be allowed to invest in new businesses. The current rules should exempt venture capital.

But the most that you can ask of a regulatory regime is too simply leave the current law alone. It’s may not be ideal, but it certainly is not broke. Dont’ fix it. Let it be.

Album:   Let It Be, The Beatles, 1970

Private venture investors consciously embrace the notion of swapping liquidity and safety of principal in the pursuit of positive asymmetrical outcomes and the higher risk premium associated with venture capital. Against the certainty of uncertain outcomes, the venture investor accepts liquidity and principal risks as the apropos quid pro quo towards achieving high double-digit and triple-digit IRRs on investment.

But, venture investors too willingly accept the notion that their investments outcomes will be the result of a binary set of events—characterized either by loss of capital or an attractive multiple on exit as the result of an IPO, sale, merger or other change of control transaction.

These investors can become more effective fiduciaries of their capital by demanding investment terms that broaden the variety of each investment’s potential returns. I refer to this as increasing an investment’s “optionality” beyond a binary set of boom or bust outcomes.

Among the most frustrating venture investment experience is the non-outcome outcome. In an earlier post (Hits & Exit Wounds) we described this sort of venture purgatory as “My Grandkids Company”—a private company that is successful but there is no exit in sight. (Perhaps your grandchildren’s inheritance?). You were prescient enough to back an early-stage venture that is now successful yet all you have to show for it is an annual K-1. This is where investment term sheet mechanisms that enhance the investor’s optionality really come in handy.

I have become a strong proponent of requiring that venture investors demand a “put right” (or, put option) as a contingency to committing venture capital to an angel round or early-stage equity financing. A well-conceived put option may reduce unintended gifting to your grandchildren by giving you one way out of a private investment without an exit in near sight.

Typically, a venture investor’s exercise of a “put” would require the company to repurchase their equity securities at fair market value. Investor put rights have been around venture transactions for years for the express purpose of providing a way out of an investment with no liquidity event in near site. But, because of the terms by which they have generally been structured, they have been rarely exercised.

That’s because if the company appears to be on the right track, investor’s are more likely to let their fortunes play out. On the other hand, if the company is not performing to plan it is not likely to be able to afford to honor the investor’s put—rendering the option worthless.

With investors rarely exercising these puts and with companies generally apprehensive of the uncertain implications of any non-budgeted hit to their balance sheet, issuers are less willing to draft investor put rights into their offerings…but you should insist.

It works like this…upon completing due diligence and deeming a venture to be worthy of a capital commitment the investor reviews the company’s anticipated revenue projections to identify a period in the future (beginning at 30 or 36 months out) at which the company’s cash flow model and pro forma balance sheet suggests that it would be able to return the investor’s initial capital contribution along with any accrued dividend. As a contingency to financing the venture, the investor requires the company to grant a put option for that future point in the company’s growth trajectory.

If the investor exercises the put, the investor is entitled to redeem all or a portion of their equity interests in exchange for the initial capital contribution value plus a nominal return above the risk-free rate. In addition to the return of investment, the put right allows the investor to maintain a reduced equity position in the company…perhaps, somewhere between 50% to 75%. (This would imply an increase two to four times higher than the company’s initial valuation)

Essentially, the exercise of the put allows the investor the ability to take “risk off the table” (the initial contribution) while still maintaining a material amount of “skin in the game”.

To prevent the investor from exercising the put at a moment when the company’s financial stability or expansion plans could be jeopardized, the company can require that in addition to a prescribed time period restriction, certain revenue and/or R&D milestones must be achieved and set as “triggers” before the put may be exercised.

The put option must be constructed in a manner that enhances the investor’s optionality, without putting the company at balance sheet risk. It is possible to achieve that balance. The company that achieves the predetermined revenue milestones would likely savor the opportunity to buy back its stock to the pro-rata benefit of the remaining stakeholders, and of course the investor benefits from the possibility of a wider variety of liquidity events and exit outcomes…which, in turn, enhances the ultimate appeal of venture capital as an asset class.

Album:    One Way Out, The Allman Brothers Band, 2004

The common and conventional wisdom of venture investing is populated with a myriad of musty and meaningless maxims that do little to develop due diligence deft. The list of utter untruths include little tarradiddles such as the purported prerequisite that a start-up must draft a comprehensive business plan when seeking financing (wrong), or that there must a clearly defined exit strategy (also wrong).

The often cited notion that the entrepreneurs have material amounts of their personal cash invested as “skin-in-the-game” is another feckless formula for evaluating venture opportunities. It’s bunk. My only private investment write-off in the last ten years was the result of backing a proven entrepreneur with a prior high-multiple liquidity event who put $12 million of his own money behind a good idea that proved to be beyond his ability to execute. An expensive lesson, but…school me once (shame on me).

The majority of the most compelling private investment opportunities originated from entrepreneurs that lacked the personal wealth to back their great idea. Sweat equity, career opportunity costs, an equity positon providing material upside incentive and personal sacrifice are generally sufficient substitutes for a founder’s flesh.

One of the more sophomoric shibboleths among venture investment evaluation criteria is the fictitious “first-mover advantage” (FMA). The naïve notion, which garnered its groupies during the dot-com delirium, suggests that the first entrant to a market space can fend off the followers and dominate the market for a material period of time. Fueled by VC funding and visions of carried interests, blind faith to this “first-to-market” fallacy financed many blow-outs and busts.

Fact is, for every Amazon where the FMA proved sustainable, there are dozens of examples where the market pioneer gave ground to a later entrant. There are only a few instances where the first mover held considerable market share (and developed material enterprise value) for a material period…such as Henry Ford’s Model T dominated the market for years until giving ground to Chevrolet.

The second mouse gets the cheese

My own experiences concur with this more accurate history of venture. I had a hand in the development of a multi-billion alternative strategies asset management firm that picked off the AUM of the first-to-market pioneer firms by developing cheaper, more transparent and more liquid investment vehicles. The pioneers spent vast sums on educating the marketplace. We simply piggybacked and poached the pioneer’s early adopter clients on the way to assuming a dominant market position.

In most cases, you are better off backing the entrepreneurs that are building the second coming of the next big thing. The slower but wiser entrepreneur for me.

Viola, Erwise and Midas, the first browsers, gave way to Mosaic, which in turn, gave way to Netscape. Chux, the first disposable diaper from J&J gave way to P&G’s Pampers. Micro Instrumentation & Telemetry Systems pioneered personal computing with Altair, which later gave way to Apple who hardly dominates the personal computer market today.

Microsoft succeeded not by being first. Digital Research developed the first desktop operating system. In fact, Softy purchased the original DOS program from Seattle Computer works for $50K. Easy to forget today, but back in the day Gates expertise was marketing, not innovating.

Visacalc, the first desktop spreadsheet program, gave way to Lotus 1-2-3 which in turn gave way to Excel.  Boeing did not pioneer the commercial jet, Disney did not introduce the theme park, Starbucks was not the first gourmet coffee shop and Wal-Mart was not the pioneer of discount retailing. They were not first—they were better.

Proponents of the FMA argue that the first entrant achieves name recognition, achieves economies of scale, locks in early customers due to consumer habits or high switching costs and develops brand loyalty…consequently building barriers to entry.

But, with the exception of truly proprietary IP or geographic advantages in brick and mortar or service industries, I don’t find those “advantages” to be sustainable by virtue of fiat. Better will always end up beating out first.

The empirical research bears this out. In the 1996 study, “First to Market, First to Fail?”, Gerard Tellis and Peter Golder demonstrated that pioneers are rarely rewarded for their efforts. Rather, they found that another class of firms labeled early leaders (the category of second and third-comers) enjoyed “a minimal failure rate, an average market share almost three times that of market pioneers and a high rate of market leadership.”

Thats because the first-mover pays a huge cost in R&D, marketing and advertising to educate and entice early adopter customers or clients. The later comers have the benefit of case study, market intel and the opportunity to sell relative value…often referred to as the “free-rider effects”, where late movers may be able to free-ride on a pioneering firms investments in R&D, consumer education and infrastructure development. These “imitation costs” are more vastly affordable than the “innovation costs” that often cause the pioneer to crash and burn.

When evaluating pre-revenue ventures, I find it best to eschew first-to-market business models in favor of the better, faster or cheaper followers. Look to who’s next. It’s easy to be sucked in by the intuitive appeal of the FMA, but I have already been schooled…I won’t get fooled again.

Album:   Who’s Next, The Who, 1971

I have noticed that VCs tend to talk to the public and with their peers more about their home runs than their strike outs. Angel investors, on the other hand, prefer to relentlessly revisit their pain—often comparing their battle scars like veteran samurai. Probably because angels put up their own capital. Because they truly do eat their own cooking it’s harder for angels to forget their fallen soufflés.

VCs achieve their highs from the opium of OPM…so even a bad trip is still a free trip.

I recently had lunch with an inveterate venture investor (aka “angel”) whom I had co-invested with in a biotech, as well as, a med-tech company, several years back. Our conversation inevitably turned to peck at our past portfolios.

The biotech company was a true home run—a high-multiple exit realized in a 2004 IPO. (When was the last time you saw biotech, high-multiple and IPO in the same sentence?)

But, rather than relishing in a reminiscence of our raison d’être, we chose to get muddy in the mire of our miss—the medical device company that (nearly seven years later) was still trudging along with neither an exit, nor a write-off in sight.

There is the baneful scenario–five or more years in an illiquid private investment that just keeps rolling over but never plays dead, and, there is the painful scenario–a company running profitable for several years straight but no IPO, acquisition or distribution on the near horizon.

Two questions dominated our discourse. First, what would become of the med-tech investment? And secondly, what can we do differently as investors to avoid non-outcome outcomes in the future?

My most previous venture ovation opined, “There is very little that is binary about venture investing outcomes. It is not just feast or famine…outcomes are diverse and asymmetric. You can lose your entire investment, just lose a portion, break even, receive periodic distributions producing double-digit IRRs or achieve exits at 5X, 10X, 20X multiples or greater…”

That list of outcomes would be just fine if it was indeed comprehensive, but I employed some autistic license. The reality of the absence of binary outcomes in private venture investment occasionally includes the potential absence of any outcome at all.

In an amusing piece “10 Exits”, Angel Capital Association’s chairman John Huston further parses this purgatory. He evokes the venture vernacular “Zombie” as “a walking dead venture that will never become a great company, nor will it die so I can declare the loss.”

There are a number of ways to euthanize a zombie but what do you do about the investment that Huston calls, “My Grandkids’ Company…a company that is successful but there’s no exit in sight”? (“Maybe it will occur after my grandchildren inherit the portfolio.”)

That is the second question, and yes, there are methods that an investor can apply at the outset of the investment that mandate distributions from profitable private companies.

I have developed some effective term sheet and funding mechanisms that enhance the optionality of a private investment’s outcomes that avoid inadvertently gifting your grandchildren. I will share them in an upcoming post. They are the byproduct of my own experiences, and as you know, experience is what you get when you were looking for something else.

Album:   Hits and Exit Wounds, Alabama 3, 2008

Contrary to conventional cliché, there is very little that is binary about venture investing outcomes. It is not just feast or famine. Rather, outcomes are diverse and asymmetric. You can lose your entire investment, just lose a portion, break even, receive periodic distributions producing double-digit IRRs or achieve exits at 5X, 10X, 20X multiples or greater on your initial investment.

What does appear to be binary is the manner in which prospective investors in private ventures perceive the asymmetric return profile of venture investment outcomes….most either adore it or abhor it.

On one hand, an investor like Jim Rogers is attracted to what he no doubt views as a positive asymmetric profile of venture investment outcomes. His venture acumen began developing at the age of five by selling peanuts and by picking up empty bottles that fans left behind at baseball games. In 1970, he co-founded the Quantum Fund. During the following 10 years the portfolio gained 4200% while the S&P advanced about 47%. Nice.

In a recent rant Rogers opined not only that “diversification was garbage”, but also went on to say that “you only need four or five good ideas in your life to get really rich”.

(Note that Rogers says “really” rich…which seems a bit elitist seeing as how only one or two good ideas can make one simply rich.)

Nevertheless, 90X returns over the S&P implies that he had very little fear of placing losing bets.

But what about those less adventurous souls that eschew positive asymmetric return scenarios in favor of more traditional investments with binary and symmetrical outcomes? Why are there so few angel and venture investors despite the compelling data of the asset class’ returns and the proven history of private enterprise as the single greatest creator of family wealth?

Economics psychologist Daniel Kahneman explained this behavior with his 1979 nobel-winning, Prospect Theory which describes decisions between alternatives with uncertain outcomes where the probabilities are known. In prospect theory, Kahneman identified Loss Aversion–people’s tendency to strongly prefer avoiding losses to acquiring gains. In fact, studies suggest that losses are twice as powerful, psychologically, as gains.

In their perpetual pursuit to mirror the risk-free rate of return, some investment advisors are factoring prospect theory and loss aversion into their asset-allocation schemes. But loss aversion studies opposing symmetrical outcomes…such as either winning $100 or losing $100. It provides little insight with respect to investor’s fear of positive asymmetric return profiles.

I prefer the wisdom in David Gal’s 2006 study, A Psychological Law of Inertia and the Illusion of Loss Aversion, which discounted loss aversion as “superfluous” and found instead that risk/return tradeoff decisions were decidedly “influenced by a tradeoff between the status-quo and change”. Gal calls it inertia, noting that that people will tend to remain at the status-quo when they have no clear preference between the status quo and an alternative option.

The rigid portfolio allocation to the same traditional asset classes within the same stale strategic asset allocation model is the status quo that Gal is referring to. The results have been far from compelling yet most investors, and their advisors, keep doing the same thing while expecting different results.

In a recent WSJ article, Jason Zwieg accounts for this “mental lazziness” that prevents  investors and advisors from challenging their status quo approach to investing (and consequently, not embracing alternative asset classes and strategies). “In short, your own mind acts like a compulsive yes-man who echoes whatever you want to believe. Psychologists call this mental gremlin the confirmation bias…people are twice as likely to seek information that confirms what they already believe as they are to consider evidence that would challenge those beliefs.”

Try Harder. Properly allocated, private equity and venture investments can materiality improve a portfolio’s risk/return tradeoffs and benefit from the proven superior performance of the asset class. But, expanding your repertoire by opening your portfolio to private investment opportunities requires commitment and effort to educate yourself on the rules of the engagement and evaluation.

Achieving superior returns by embracing private investment requires initiative…not inertia.

Album: Underachievers Please Try Harder, Camera Obscura, 2004

One of the few commonalities among the thousands of VCs and angel investors is the consensus that the process of identifying an attractive private venture investment is “part art, part science”. The art part speaks to the inherent absence of certainty with respect to any venture’s viability. There are no absolute truths…no bankable checklist to follow that ensures a successful outcome for a private venture investor.

The science part? That’s simply hindsight, which of course is an exact science. Of the ways that I have derived knowledge as a private venture investor, hindsight is the most expensive, the least merciful and the most valuable.

When it comes to separating the wheat from the chaff, my primary screen is simple. For a private venture investment (PVI) to be worthy of the costly, time-consuming, bandwidth-bogarting process of evaluation, consideration, due diligence and deal term negotiation, it must initially meet these four criteria;

1.  There is a large market for the firm’s products or services

The size of the market must be material for a PVI to potentially achieve a high cash flow or high-multiple (positive asymmetric) outcome. The success of category-killer app, product or service in a small market lacks the potential of an exponential payoff and does not proportionately offset the risk of a loss.

Ideally, the market should not be merely mature—it should be a growing market. The market can be newly-emerging (alternative energy, for example) or non-existent (Twitter) at the point of the venture’s introduction of its product or service, but it’s potential must be measurable and meaningful.

The values set forth in the modern business classic Blue Ocean Strategy often come to mind. Blue oceans denote industries untainted by competition. In blue oceans, demand is created rather than fought over…competition is irrelevant because the rules of the game are waiting to be set.

I am predisposed to the notion that the initially contemplated product, service or business model rarely succeeds, and consequently ventures are frequently forced to adapt to new data points. This requires the room to maneuver that a large market provides.

2.  The firm has a sustainable competitive advantage

The venture must have a sustainable edge to attract and retain its market share. The location or lease of a real estate development can be an edge. The celebrity chef to a restaurant, the IP portfolio of a technology or medical device company or a strong distribution channel relationship can be a critical edge to a consumer product.

The more tangible, unique, defensible and proprietary the edge (such as patents)…the better. The competitive advantage should discourage competition and create a barrier to entry. The edge will vary according to the venture’s industry. First-mover status is often meaningless (like many others I prefer second-mover) and certainly not sustainable in a market of compelling size.

A sustainable edge to compete in a large market is critical to potential acquirers or public markets and the objective of realizing compelling multiples on an exit.

3.  The management team has compelling expertise in the contemplated market

You must have a great execution team. Visionary founders may be inspiring but they alone cannot bring a great idea home. Get an experienced and accomplished operator in early.

In a couple of my early investments I failed to hone this rule to its proper endpoint. Naively, I believed that the serial entrepreneur with prior liquidity events was a proven winner and worthy of the wager. The first time that formula fell short I failed to make the proper connection, the second time I learned the lesson. There will not be a third time.

Successful entrepreneurs too often become deal junkies fueled by the fumes of their prior triumph. Some become self-anointed business “generalist” experts (contradictory, eh?) that no longer feel restricted by the limitations of their actual core competencies.

The founding partners and management team must include an accomplished C-level executive or highly accomplished operator with a track record of proven experience with the specific business model and target market. Moreover, the operator must have the authority and discretion to execute the business plan. Serial entrepreneurial ego in the absence of domain expertise is a formula for failure.

4.  The deal terms are no less than fair, and ideally—favorable

Valuation, investor rights, board representation, management discretion and transparency with respect to material events, protective provisions, anti-dilution protection, liquidation preferences and optionality issues must incentivize and respect the source of the capital. The investor’s capital is the great enabler… the sine qua non for any venture.

Few things are as humbling as the successful venture that does not translate into a successful investment. I respect the often repeated axiom that a fair deal is one where both parties feel that they got a bad deal, but the end game should always be to negotiate favorable deal terms.

The probability of an attractive outcome is diminished if a private venture investment cannot meet these initial thresholds. In VC-speak you are nursing a newborn “zombie”…a walking dead venture…the ship is already sinking and it has not even left the port.

Album:   We Were Dead Before the Ship Even Sank, Modest Mouse, 2007

As my career has been largely devoted to the intersection of money management and venture finance, I am no stranger to the independent RIA universe.

I have worked with dozens of wealth managers and family offices that regularly evaluate and allocate to private venture investments. Although they represent a fraction of the RIA universe, they are invariably among the most successful of their peers. These progressive wealth managers represent the primary audience of this blog.

I regularly advocate that RIAs that possess the requisite mandate, the means and the mindset should embrace private venture investments–for the benefit of their client’s portfolios, as well as, their practices. Yet, the majority of independent wealth managers should best leave this sandbox to VCs and angel investors.

Does your advisory practice possess the rationale and the resources to advise clients in start-up, early-stage and other private venture investments?

Your advisory practice may be uniquely qualified, if you consider:

• (To begin by stating the obvious…) You are in the business of wealth preservation and wealth creation.  Without question, the primary source of family wealth in America is the result of private enterprise and private venture investments characterized by their potential for positive asymmetric outcomes.

• You embrace Modern Portfolio Theory.  Despite its flaws, MPT advocates diversification into non-correlated asset classes. One-off investments in private ventures are distinctly non-correlated to broader asset classes and major market indices and have exhibited less correlation during negative black swan events.

• You possess the proper due diligence skills.  In addition to those skills you also posess the doubting disposition that is critical in evaluating private investments. The skills that advisors have developed in the course of investment manager evaluation are relevant and applicable to the private equity universe. Moreover, your experiences have taught you to be cynical and skeptical of assumptions regarding future performance.

• You are an entrepreneur.  As an independent wealth manager have chosen to compete in a highly-competitive, low margin industry. Your personal experiences should render you more prone to recognize the prerequisite personality traits of a successful entrepreneur…de rigueur in the executive team due dilly process. You also recognize the mission-critical elements beyond the strengths of the management team that determine the probability of successful enterprise.

• You understand finance.  As a stock, sector and industry analyst you know your way around balance sheets, cash flow, valuation issues and income statements. I am frequently surprised at the number of professional private venture investors that have little understanding of business and finance.

• You possess both an awareness of regulatory issues and a fiduciary responsibility that is consistent with the best practices of seasoned angel investors and VCs.

• You are networked. Beyond your practice, you have access to an expansive network of tools, resources and expertise that are essential to evaluating new technologies, industry sectors, new business models, intellectual property and other elements of private investment. Your industry colleagues offer incomparable access to the analysts, research, legal and domain expertise that is required in the course of successful private investing.

• You have access to the critical resources.  As an independent wealth manager you have enviable access to the two most important resources of private investment….investor capital and deal flow. Your HNW clients most likely became HNW clients as a result of their own ventures in private investment. Serial entrepreneurs and HNW investors are an excellent ongoing source of deal flow.

Advisors that affirmatively identify which each of these traits may have the mandate and the means to expose their client’s portfolios to the asset class that has historically created the vast majority of our nation’s private wealth and can dramatically differentiate your practice from its peers.

More advisors should explore asset allocation beyond the lame limitations of highly-correlated asset classes, stale style boxes and pointless pie charts.

Album:    Playing the Angel, Depeche Mode, 2005