The Monk And The Riddle

Welcome to the History of Computing Podcast, where we explore the history of information technology. Because understanding the past prepares us to innovate (and sometimes cope with) the future! Today we’re going to review a fantastic little book, called “The Monk and The Riddle” by Virtual CEO Randy Kommisar Like a lot of authors, I’m a reader. There have always been a lot of technical books in my house. In fact I had to downsize at some point because they were getting out of control. So I made a dedicated Instagram account called deadtechbooks to post photos of books. Separation anxiety is for reals. But I’ve also read a lot of books about startups and venture capital. And it never ceases to amaze me just how big a jerk most of the authors are. There are the super jerks who just come right out with it and let the reader know they invested in Google or Amazon and have billions to throw away. And that they’re so god-like that should you pitch to them, you’ll be struck down by some kind of Jesus fire. You’re left wondering why they bothered to write a book. But then you realize it’s an elitist business card. Then there are the overly eloquent nerdy jerks who let the reader know how rich they are by hiring a ghostwriter with such great prose that the biography pretending to be an autobiography would likely be taught in literature courses along with their fellow literary greats had they not chased a big old vapid paycheck. you can feel the disdain they have for the giant douchenozzle paying their check oozing between the book bindings. You can empathize with the ghostwriter, given the landmass of ego they distilled into perfectly digestible 7th grade prose. Nerdy founders who go down this route likely need to partake in the spirits just as badly given many will never have a good enough idea to found another company that actually bothers to launch a product. Then there’s the opposite; the autobiography masquerading as a biography. You can feel the subject become the author. Sometimes they commission the book. Other times the author becomes enamored with the subject of the book and all objectivity is lost. There may be thinly veiled attempts but founders, investors - they can be seductive to a storyteller. Whether through accomplishments or wealth. Don’t get me wrong, love stories are great; they just belong in the romance section of the bookstore. Then there are the startup guides. Be very careful because one size doesn’t fit all. Saying you have to do things using a formula is as dangerous as it is delusional. There are no best practices when starting a company, only worst practices. Some use such arcane tactics that many a buyer for a new startup might consider them offensive. To be clear though writing potential customers hand-written thank you cards is quaint and totally legit. Then there’s the books that focus on the facts. But without opinion or feelings they read more like code. The worst of the bunch are the humble-brags. These self-defacing tomes make sure you know just how smart the author is. Their wealth or brilliant ideas tell you exactly what you need to know. Or they would if the author didn’t tell you it was just a matter of timing, right before taking you through all of their business master strokes in a wild stimulation of... themselves. I’ve learned to read between the archetypes. Sometimes I get lost and later realize what happened but I frequently start a book just a bit leary. Randy Komisar is none of these. He began his professional life as a lawyer and then worked on the deal that put Pixar in the hands of Steve Jobs. From there, he landed at Apple and worked to license the Mac operating system. When that fell through he ended up co-founding Claris with Bill Campbell. He tells the reader some of his failures along the way, but never with an air of the humble-brag. He speaks of Campbell and others with reverence. Not as heroes but as mentors; not with adoration but with warmth. He then goes through how he landed in what we now call venture capital. He addresses his good fortunes and privilege and mixes pronouns in a way that doesn’t feel the least bit contrived. He mentions his time and involvement in the early days of webtv and TiVo in the book and explains the differences between a few types of startups in a way that’s easy to understand. Komisar warns against being bigger, faster and cheaper while telling the reader that sometimes that’s actually the right way to launch a company. He doesn’t bother to tell the reader too much of his own story until pretty late in the book. Instead he focuses on a startup who is pitching him. He explores motivations and the type that align to his world view. He does so with a genuine desire to help a person he doesn’t initially like. Why? Because he sees something in the big idea the guy has. But through the book the young founder pivots into a content portal over time with no clear route to make money but instead a focus helping people. Throughout the journey he drops insights that can help a reader navigate that world but not overtly. By the end you’re left wondering where the journey has taken you, and you almost forgot about where it began. The book opens with a story of meeting the Dalai Lama. It’s not a bragadochio opening. Instead It’s a “this isn’t going to be your typical startup book” opening. By the end you’ve almost forgotten about where the book began. The monk had asked the author about why people aren’t more compassionate to one another. By the time the book is done the author has become the monk and helped the startup reorient around compassion. And the author has shown compassion to the young founders by looking past their initial presentations full of charts and graphs and helping them recapture the why behind their idea, moving away from big, fast and cheap. So next time you’re out trying to sell your ideas, dig below the surface. Revisit your passion. Let your motivation show and you just might find a champion who can help you find a path to something that you maybe didn’t see in your own journey. This book won’t be for everyone. But I’m lucky it landed in my lap at a time when I was able to accept the message. Just as I’m lucky you chose to listen to this episode of the history of computing podcast. Thank you so much for joining me. Have a great day!