To outside observers, it sometime seems that investors are very lucky when they get an exit and make a spectacular return. Those of us who invest regularly in startups, and then take an active role, know that there is a great deal more than luck involved. It’s really hard to have a startup survive to get to exit. There is no formula, nor is there an algorithm to follow that makes this so. Would that it were so! If you drive your car by looking intently in the rear-view mirror, you will know with great precision where you have been, but are unlikely to avoid the truck that is driving straight at you.

But.. there is one thing that is generally predicative of success – valuation. If the valuation is set too high, you risk crashing on a down round when the inevitable happens and things that can go wrong, will go wrong. If you set the valuation too low, then the entrepreneur owns too little of the company to be incented; and follow on rounds with new investors is difficult because ownership is too concentrated in the hands of the early investors.

From both the entrepreneur’s and Angel’s point of view, it is better to grow the valuation steadily (and most usually slowly) than to have a high valuation at the start and then not increase the valuation later. Raising money is difficult at best; it becomes ever more difficult when valuation expectations are not aligned.

So, I make the following three recommendations:

1. Balance, balance, balance. It is critical to understand the amount of capital that must be raised in the first round, what milestones that money will attain, and if that is sufficient to achieve the following round. Some businesses are just not financeable by Angel investors. If, for example, if your company really needs to raise $2M to ship your product that only addresses a potential $10M opportunity, you are unlikely to raise that money. And.. raising only $250k with the hope that, before you hit a meaningful milestone, you will later raise more is not fair to you or your investor.
2. Try to project capital needs for future rounds (yes.. I know that most plans say this will be the ONLY money that the company will ever need. But I can’t think of an example where that was actually the case). Understand that each new investor in these future rounds will expect that their investment will lead to a good return – in short a good deal. The existing investors will like their investment to grow; they took a risk on the entrepreneur and the company and would like to see value commensurate with the risk they took, especially if you need them to continue to invest. And lastly, the entrepreneur team wants to maintain a reasonable stake that can lead to a good value on exit. While this is hard in the initial round with only one set of investors and the entrepreneur team, it is much more difficult when there are also new investors joining the process.
3. Know the market. Angel Groups, like the Alliance of Angels, see a lot of deals and know what Angels consider a fair valuation for the risk and reward that those companies present. There is a market for Angel financing of startups. And, like any market, supply and demand matters. Seek advice on valuation from trusted sources, but weigh the advice heavily towards those that write checks to startups. We often ask entrepreneurs how they came up with their valuation. The most common answers are: (a) my lawyer told me that was fair; (b) I looked on the Internet to see what bloggers were suggesting; and/or (c) I build an excel spreadsheet that shows the valuation after we are successful and did a backward projection. While all of these methods have merit, they rarely lead to a true market-based valuation that leads to a quick and successful financing. While it is no fun to explain to an entrepreneur that the current value of their company is significantly less than they believe it should be, this is why “professional Angels” have become a trusted source for setting fair valuations.

In summary, the best way for an entrepreneur and Angel to agree on valuation is to see the deal from each other point of view.

More startups fail because of poorly set initial valuation (both too high and too low) than almost any other cause. This is an easy problem to solve, but it must be solved up front. We are lucky to have professional Angel groups that are willing to work with entrepreneurs to help startups succeed.