The S Word

For many people, the word “strategy” conjures up images like this one (an actual slide from my strategy professor last year): 

Strategy is theoretical. It’s amorphous, intangible, and fluffy. It’s a presumptuous MBA drawing red lines connecting concepts and assuming that their work is done. It is the complete opposite of what startups and their founders stand for and prefer — execution, “doing things,” “getting shit done.” Diagrams like the one above give strategy, per se, a bad name. It’s associated with the b-school student who’s trying to break into the startup scene but doesn’t really have any “true value” to add. Strategy has become a taboo word to mention around an early stage company, particularly one for which you’re trying to work.

However, despite the knocks on strategy and the people who want to “do it,” there is a meaningful place for it in a startup environment. It is on the same level as execution for the simple fact that you shouldn’t have one without the other. We saw this firsthand at Gumroad when determining which verticals and specific content creators to approach. Each choice was evaluated closely prior to sending those initial emails to managers, agents, label execs, and creators themselves. This statement will sound self-evident, but all decisions are inherently strategic. And if you don’t consciously think about the strategic aspects and implications of a decision prior to executing, you’re doing your company a disservice.