The Founder's Dilemmas

Wasserman is a well of knowledge for people problems in startups. The book is an overview of major decisions that founders have to face, beginning from whether to found a company to deciding the successors of the company's leadership. Wasserman’s thesis is that often, there exist decisions that founders face early on which have long-lasting consequences, decisions that founders often don’t take so seriously or actively try to avoid due to their contentions nature, such as which cofounders they work with and how equity is split. This book was a stepping stone for me, forcing me to look within myself and see which end result I really want, and from those end results decide which paths along the way would be the best. I regret not reading this book even earlier, since I’ve already made some decisions in my first company that I could have handled better.

The most important idea is the core, overarching dilemma between having control and wealth. Wasserman’s data pits the two ideals against each other. As a company matures, it often relies on outside capital, and the investors ask for some control in order to have a say in their investment. After 2 or 3 series of venture funding, most startup founders have already lost majority control of their startup, some even being ousted as the chiefs, or hired someone better and gave them the reins. Those who don’t lose control, often struggle to scale the startup since they have trouble attracting investors and talent, and often scale slower. Facing this dilemma, it forced me to think about what I value. Right now, at my age of 22, I'd say I value wealth more than control – wealth begets power in the future, but power without wealth is only ephemeral and even at that, the fearful prospect of losing power probably isn’t worth it if it means I'd be losing out on building actual wealth.