What I’ve learned after 5 years of buying common stock in startups

From day one, Pillar VC has offered to buy common stock in startups.

Instead of the standard 10-page venture capital term sheet riddled with terms and conditions, our team believed that a far simpler structure where we owned the same security as the founders would align interests, increase trust, and hopefully, enhance the performance of our investments.

There are many terms and conditions in a preferred term sheet that can misalign investors and founders

Five years since launching Pillar, as we finish investing our second fund and begin deploying our third, we thought it was a good time to reflect on whether buying common stock instead of preferred stock has offered the benefits that we had hoped for.

Preferred stock can misalign incentives between parties

There are many terms and conditions in a preferred term sheet that can misalign investors and founders — for brevity, I’ll highlight just two below. (For more, see the term-sheet grader).

Preference: Preferred stock has a “preference” that gives the investor the right to choose whether they want to get their money back or take their percentage of the total proceeds. In downside scenarios, having an investor take their money back may mean that they are taking a far higher percentage of the proceeds than the founders “thought” they sold.

For example, if an investor buys 25% of a company for $2 million in preferred stock, their break point on this decision will be $8 million, which happens to be the post-money valuation of the round. If the company is sold for less than $8 million, the investor would rather take their $2 million back. If the company is sold for more than that, the investor would choose to take 25% of the total.

The founder thinks that they sold 25% of their company, but that percentage is actually determined by what the company is sold for. Yes, if the company is sold for $8 million or more, they sold 25%, but if the company is sold for, say $4 million, the investors will choose to take their $2 million back, which is 50% of the proceeds. Worse still, if the company is sold for just $2 million, investors will take all of it.

Anti-dilution: This clause means that if an investor buys shares for $10 and the startup raises money in the future at a price point that is lower than $10, the investor’s share price will be recalculated retroactively to a lower price. How is this done? By issuing the investors more shares, which dilutes the rest of the ownership pie, especially the founders and employees. The company is not performing well and the investors are made whole at the expense of the founders. Aligned? Hardly.