Founder's Dilemmas & Exceptionalism

I recently read Wasserman's The Founder's Dilemmas after a conversation with Andy Sparks. The book itself goes into detail on specific choices (when to start, choosing cofounders, equity splits, early hires). Two things stuck with me.

Wealth vs. King

A large chunk of the book is devoted to entrepreneur's motivations. Wasserman showcases two motivators - the desire for growth (wealth) and the desire for control (king).

I originally chafed at this distinctions. I think wealth motivated founders would like to sort themselves into "impact" and control motivated founders would like to sort themselves into "vision." But I do think wealth and king accurately describe the outcomes.

When I'm not in charge, I'm definitely motivated by wealth. I've struggled with control oriented leaders, much in the way the book lays out. If I were to join another early stage startup, I would definitely ensure the founder was wealth motivated. Similarly, if I were to found another startup, I'd want my cofounder to be wealth motivated.

However, when the founder-CEO starts making control-oriented decisions, such as refusing to raise needed capital or to delegate decisions to experienced executives, the wealth-motivated hire is likely to chafe under the founder’s leadership and to feel that the founder is sacrificing the hire’s benefit (value creation) for the founder’s own benefit (personal control).


Being a founder often means ignoring conventional wisdom. But we do have some data on failures and successes. If I were to pick mistakes I have made, nearly all of them could fall in this bucket:

Throughout this part of the book, we have examined how founders’ natural inclinations can create pitfalls for their decision making and for their ability to build their startups. Passionate, confident founders often hear about the problems ... but want to believe that they are different, that they will be able to deal with it. One founder lamented to me, several months after his startup had failed, “Even after you showed us the data ... we just figured, ‘Those things happen to other people, they won’t happen to us.’

I think this comes up a lot in wealth vs. king. Many founders try to say that the only way to generate large wealth is by being king, despite evidence to the contrary.