The Monk and the Riddle: The Art of Creating a Life While Making a Living (1999) by Randy Komisar

Written in the “olden days” of the Internet (i.e. late 1990s), Randy Komisar’s “The Monk and the Riddle” is a classic with a timeless message: there’s a fundamental difference between passion and drive. The latter is what propels type A personalities to succeed at anything they undertake. The former is more visceral and personal; it is something that you genuinely love and would be happy “to do for the rest of your life.”

Komisar, my good friend and mentor (full disclosure), conveys his message through the story of his interactions with an aggressive but morally wayward entrepreneur by the name of Lenny who is pitching a business plan for funerals.com, an opportunity to sell caskets and linings online at a fraction of the price demanded by the traditional bricks-and-mortar funeral homes. It quickly becomes clear that selling caskets more cheaply on the Internet is not what Lenny really cares about nor what drew him to the opportunity in the first place. Over the course of several chapters, mostly told narrative-style between the author and Lenny, Komisar learns that beneath all the snazzy PowerPoint decks and pitch buzzwords there is a deeper idea at play that Lenny genuinely wants to pursue, but is afraid that it’s not a legitimate business idea. He calls it “Full Circle” and it sounds an awful lot like a Facebook for funerals, although the book was written when Mark Zuckerberg was still in junior high school.

Komisar ultimately passes on the deal — at least from working directly with Lenny as Virtual CEO — but he tells an important story in the meantime. Essentially, entrepreneurs need to be driven by passion. They must want to establish their company and vision not to get rich, but to make the world a better place, however it is that they believe that’s possible. It is an argument for startups stripped of recently minted business school students, motivated primarily by avarice and ego. Komisar knows better than most that very few startups turn into Google or Instagram, so the founders need to be motivated by something beyond (and far deeper than) mere dollars and sense (pun intended). Indeed, it is those with such an altruistic and passionate approach who often end up winning in the end.