This guest post is authored by Mark Bivens. Mark is a Silicon Valley native and former entrepreneur, having started three companies before “turning to the dark side of VC.” He is a venture capitalist that travels between Paris and Tokyo (aka the RudeVC). You can read more on his blog at http://rude.vc or follow him @markbivens. The Japanese translation of this article is available here.

Red Auerbach — winning basketball coach of the Boston Celtics for 9 NBA championships in the 1950s and 60s, famously remarked that, “You can’t coach height.” He made the statement in response to a reporter‘s question on why he drafted somebody who turned out to be a fantastic player but didn’t possess much in the way of basketball skills other than being super tall. In other words, some favorable basketball attributes can be coached: passing, dribbling, shooting free throws, making plays, rebounding shots, etc. whereas other attributes can never be taught, namely a player’s height. 
I think the equivalent of this expression for entrepreneurs would be, “You can’t coach ambition.”

This expression came to mind again as I witness reverberations in the Silicon Valley echo chamber about the recent funding round of Clubhouse. 

The brouhaha relates to Clubhouse’s Series A fundraising of $10 million from Andreessen Horowitz, which was accompanied by $2 million worth of secondary cash paid directly to the Clubhouse founders.

Perhaps it’s because I spent more of my investing career in Europe then in Silicon Valley, but for me, creative deal structures like this one — even if it looks egregious to some on the surface — do not strike me as eye-popping. 

Although I would not classify most European founders as underprivileged, very few come from positions of extreme wealth. Most of the entrepreneurs I have encountered had been toiling away for years with modest wages (especially on a net basis after significant taxes and social charges), and limited capital gains from other sources such as stock market appreciation. Functioning universal healthcare coverage provides a safety net on the downside, in contrast with the U.S., making entrepreneurship accessible to a wider range of economic classes.

For these and historically cultural reasons, the go-for-broke mentality is far less prevalent among European entrepreneurs.

So I’ve been no stranger to structuring deals with a secondary component for the founders who have been plugging away for years with relatively little concrete monetary value to show for it. No, I have not offered secondaries of $2 million — closer to an order of magnitude smaller — nor have I offered them on Series A rounds, only at later stages. However, I’ve done them on multiple occasions.

In some cases, the secondaries have worked out superbly well, removing obstacles for founders to strive for aggressive growth. On other occasions, they provided little or no improvement, and have sometimes even backfired by misaligning the interests in the cap table.

It was only after numerous experiences with these that I realized the importance of controlling for another variable: the intrinsic ambition of the founder.

If a founder’s self-imposed restraint stemmed from external factors, for instance family responsibilities, alleviating such burdens with a small secondary payout has proven wildly effective. If the risk aversion originated from within, on the other hand, the hoped-for benefits of a secondary structure never seemed to materialize.

Ambition is raw. It sits independently of the support I might provide to portfolio companies, either directly or by finding people who do. Company structuring, financial management, marketing, pitching, fundraising, negotiating, recruiting, exit positioning, etc. all of these skills can be fostered and encouraged.