A Startups Guide to Milestone Investing

 In Blog
August 6, 2014 – By Bill Liao
Too much money is rarely enough.Strange thing is, money, in and of its self, has no value. Yet we have co-evolved with money to the point where it has very strange effects on the physiology of our brains.For instance, as Dan Pink famously popularized more cash rewards it lead to poorer performance in undertaking tasks that involve even rudimentary cognitive skill.From my own experience, I have also found that the more money you have at any one time the easier it appears to be to spend it both literally and, crucially, emotionally.

The investment landscape is littered with the hollowed out shells of companies that raised truly enormous sums of money from investors only to then implode in a frenzy of overspending.

This is also testament to the fact that while it’s easy to spend a million dollars, it’s a lot harder to spend it wisely. And it is even harder to make two million more while doing so.

If you have spent a long time raising money from investors by pounding the pavement and dialing for dollars, there is a sense of achievement when the big cheque finally arrives. In fact, this sense of achievement is the falsest of false dawns, for the light at the end of the investing tunnel is all too often the headlight of the oncoming freight train.

Another dangerous side effect of large sums of money beyond an almost irresistible and patently irrational hubris is that the science tells us that compassion also tends to evaporate around money. If there is one time when a leader needs compassion it’s when they are driving their young team to go beyond the limits of endurance to make something work.

And what of the team it’s self? Does cash have any negative side effects for them? You bet your aunty Mabel it does. A full bank account suddenly stuffed with, as yet, unearned cash, can inflate all kinds of spending wiping away years of patient lean practice with profligacy. This can have even the most loyal team members question whether they should work 48 hour shifts for minimum wage and (as of yet) worthless equity.

Over funding is far more dangerous in my experience than underfunding and neither correlate particularly well to overall success.

The simple yet bitter truth is that for money to be handled well takes practice. It takes a range of abilities and money that is not properly earned actually is always dilutive, not just in terms of equity. It is dilutive in terms of focus as well.

So what to do?

So far I have made a pretty good case for never speaking to an investor and given that is my day job, a job I happen to both believe in and thorough to enjoy, what hope is there of success given the apparent toxicity of money? Where,in fact, too much money all at once is not only not nearly enough, it is positively devastating.

Enter the humble milestone.

What many people have come to regard as an almost insulting show of investor distrust is in fact a potential panacea, if applied intelligently.

Now milestones can have major downsides for the entrepreneur. This is especially true of those who are unrealistically optimistic. A milestone that is poorly formed and overly optimistic becomes instead a millstone, dragging the team towards sometimes wholly inappropriate outcomes.

Even so, well formed and thought through milestones that are pre-agreed between the parties, provide many benefits. Not the least of which is the sense of having earned the cash though achieving something meaningful.

Ultimately, milestones are pretty simple and should be constructed out of markers that can be easily measured. One key thing that makes a milestone valuable for the entrepreneur is that the milestones should be based on measuring traction that is externally validated.

The obvious targets for externally validated traction are revenue and profitability and there are other metrics that should bear notice. For instance, the level of increase in user adoption and usage are sometimes even better measures of shorter term success (or longer term)

What does not work is having excessively complex milestones or having no flexibility to have a change in direction to find better milestones on an alternate route to success. (As long as the discussion takes place early on when trouble is first spotted. Last minute failures to achieve cannot be cured with pivoting milestones)

The benefits of investment cash being given in response to well designed and mutually agreed milestone achievement include cures for all of the proceeding maladies. As the entrepreneur at no point, finds themselves with a company awash with cash and suddenly disgruntled team members.

It’s also my view that overachievement of milestones that are externally validated should be a trigger for new valuation discussions to reward excellence. While conversely significant underachievement can be a trigger for reductions in valuations or a signal that the business is not actually viable.

This last point may be the bitterest of all for an entrepreneur to swallow. Yet there are times when the almost maniacal “sticktoitiveness” that an entrepreneur must possess to succeed can actually cause them to hang on to their idea far beyond its use by date and a failed set of milestones can then be a beneficial indicator or warning flare of a possible sinking ship allowing them to finally throw in what remains of the towel and move on to something new, different and better.

Thus the failed milestone is then the trigger for them to cut their losses and embark on a new journey (almost a badge of honor in some places) that they might otherwise have missed enduring a much longer, drawn out and more miserable failure.

Of course, maintaining a milestone based investment approach takes a lot more interaction and work on the part of the investor. There will be upsets when milestones are not achieved as well as serious discussions if they need to be altered. But ultimately, they are deeply beneficial to all parties.

Because nothing beats achievement… and doing what you said you would.

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