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The most thoughtful startup founders and executives often make the same mistake. They have too much conviction as to whether their promising startup will succeed.
Predicting outcomes is tremendously difficult, even for sophisticated operators at exciting companies. And one cannot underestimate how their involvement with a startup can cloud their judgment as to the likelihood of its success and its merit relative to alternatives.
I will give arguments and concrete examples. And if they resonate, the implication is that founders and employees need a paradigm shift in the way that they manage risk.
They need a way to protect one’s equity, that does not compromise one’s alignment, upside, and passion for their work. Whether that’s partial secondary sales, cashless diversification (Aption pools), option financing, or other mechanisms.
“Ok," you might think to yourself, "I can understand the argument for diversification. But when I'm in the day-to-day of my company, I understand so much about its operation.. My advantage is in that ‘insider knowledge’”.
In fact, these observations are less valuable than they seem. Even for an experienced founder or operator. But before we can advance this controversial argument, let’s agree on something:
Picking successful companies is extremely hard. Even when they are being picked at a moment that they are performing very well.
We know this is true in the public markets (the vast majority of hedge funds cannot beat an index fund, over time). What might be more surprising is that it’s true in the private markets as well, despite the legality of insider information.
I’ve seen the historical returns data for one of the best, most well-known growth stage VCs in the world. They only invest in mature, healthy, dynamic businesses. Their model is to make decent returns on all of them, and have some of them break out.
Yes, their returns look similar to those of an early stage fund (a few bets carrying most of the portfolio). Most of them underperform and a few break out more than expected. This is despite an incredibly high performance bar, for the few investments they choose to make.
And consider the talent in this market. A VC needs to show differentiated thoughtfulness, intelligence, work ethic, etc. to break into the industry.
They then go on to look at thousands of businesses. And unlike operators, they don’t need to worry about receiving a paycheck from any of them – they just need to pick just their one or two favorites. After spending dozens of hours with the founders, reviewing bookings, pipeline, marketing, efficiency. Drawing on widespread institutional knowledge of how startups develop and pattern matching in a way that only a trained professional investor can. Speaking to customers in-depth and asking challenging questions. Speaking to competitors and assessing technological and tactical advantages.
The vast majority of venture-backed startups fail.
This should have huge implications on the confidence that one is willing to have in their startup. Deep conviction from thoughtful investors does not translate to consistent success. Much less “home runs”.
What does that say about one’s ability to pick the likelihood and scale of their startup’s success?
A late-stage startup that I know well took a large investment from a strong VC fund.
The diligence process that this fund underwent was stupendous. Every single billing file was turned over and reconciled with every financial statement. A world-class competitive analysis was created, complete with dozens of slides that encompassed hundreds of hours of high-caliber professional work. Top customers were spoken to about their commitment to the product and to the company. Only after the company passed these tests with flying colors did this firm complete the investment.
Within 6 months, this legitimately ultra-promising rapid-growth company lost its momentum, to the surprise of all the investors and executives, both new and old. The major customers that this investor spoke to (and who spoke the world of the company) churned. The investment was immediately impaired.
“Okay”, one might say. “A sophisticated investor might still be wrong the vast majority of the time. But they aren’t on the ground, in the company. Being part of day-to-day operations offers a more nuanced perspective than what an investor can ever get.”
This might be true. However, it doesn't correlate with ability to predict outcomes. If anything, it can be misleading. That’s because very few executives have a full picture of what’s going on at the business.
(Caveat – the one major exception is the CFO. And it’s no surprise that the earliest adopters of diversification solutions like Aption have been CFOs, including those of top startups in the world.)
If you look through a Glassdoor for investment advice, you’ll mostly see red herring
A common dynamic in strong growth stage businesses is that as they build out a mature operation, there is dramatic degradation in Glassdoor reviews. At the inflection points of some of the most successful companies I've known, there is often (but not always) a plummeting of average employee feedback from ~4.5-4.8 to ~3.5-4.0.
The reviews themselves don’t just bemoan “the good old days of being a small company”. They are pointed and specific!
They give examples of operational incompetence. They explain how the company has lost its way, how sales quotas are unachievable, now management is unprofessional and chooses favorites, and so on.
It’s not uncommon for companies with such reviews to announce an IPO or large M&A, that seems “out of the blue”.
On the flip side, I know of growth-stage companies with effusive Glassdoor reviews and huge sums of capital raised from great investors that suddenly laid off massive portions of their staff. Cultural strength and the operational observations can be unreliable indicators of long-term success and failure.
No one in the company gets the whole picture, besides the founders and to some extent, the CFO.
Not only that – the company deliberately obfuscates the reality from employees, to keep a consistent culture and improve retention.
For example, I've witnessed board meetings at many promising and dynamic companies. More often than not, the most trusted executives will give highly-detailed presentations on particular dynamics at the company. They’ll be exposed to candid board conversations as well. But the same executive will often not be present just minutes later, when critical and non-obvious business concerns are raised. Matters that would be absolutely critical for them to know, to develop a point of view about the promise of their equity.
And founders themselves don’t always understand just how positive or negative a certain piece of news truly is. They are untrained as inventors, heavily occupied with day-to-day operations, and emotionally attached to their business in a way that can cloud objective judgment.
Both investors and insiders struggle to make sense of what will happen at a company. There are many ups and downs that no one expects. The amount of luck and randomness involved in any given startup cannot be overstated.
Consider Docker, an investment I sourced for Insight Partners. It launched to much fanfare and Benchmark led a round. It lost its luster as its enterprise and security offerings failed to take-off. It went open-source to much fanfare and Insight led a round. And then it lost momentum once more.
It launched product after product that didn’t pick-up as it should. It went through down rounds and CEO replacements. It was considered by many to be a lost cause. Then, many years after being founded and repeatedly being left for dead, revenue began to explode.
Startup shares can be some of the best investments in the world. But when left as standalone holdings, they are often just shots in the dark.
The key to managing these equity stakes is “balance”. Whether that’s option financing, secondary sales, or an Aption pool, founders and employees should mitigate the risk of their large and concentrated holdings.
This nuanced, open-minded approach is the one best supported by data and commonsense. It protects downside, while keeping the upside that everyone hopes for.