I’m surprised I waited so long to read this book by Randy Komisar, now almost a decade old, titled The Monk and the Riddle: The Education of a Silicon Valley Entrepreneur
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The book is a light read, I finished it between two short airplane flights to/fro Philly. Lots of this stuff is intuitive if you read startup rags all the time, but I like that Randy’s book is written from the perspective of a VC talking to an entrepreneur about his million dollar idea, “funerals.com”. Anyway, there are some great reminders for startuppers in there. Most business books make me yawn but this one is way more than a business book.
My favorite parts, painfully typed out for your benefit.
p42
I have never seen a company fail for having too much money. Dilution is nominal, but running out of money is terminal. Set reasonable expectations among your investors, don’t gouge them, and then out-perform expectations. Future rounds will be much easier if you are seen as having positive momentum
p52 — A brief explanation of Rocket Ship Models of startup investments vs Brave New World startups (that proceed more gingerly, without the precedents to guide them).
p55
I have to share this one with my (sometimes) Marxist design friends
Business is one of the last remaining social institutions to help us manage and cope with change. The Church is in decline in the developed world, ceding leadership to a materialism of unprecedented proportions. City hall is subservient to the economic interest of its constituencies. That leaves business. Business, however, has a tendency to become tainted with the greed and aggressiveness that at its best it channels into productivity. Left to its single minded pseudo Darwinian devices, it may never deliver the social benefits that the other fading institutions once promised. But, rather than give up on business, I look to it as a way, indirectly, of improving things for many, not just a lucky few. I accept its limitations and look for opportunities to use it positively. In the US, the rules of business are like the laws of physics, neither inherently good nor evil, to be applied as you may. You decide whether your business is constructive or destructive. H help people understand this and express themselves in what they do, trying to make a difference through business.
p65
The Deferred Life Plan: Step One: Do what you have to do. Then, eventually — Step Two: Do what you want to do. The Deferred Life Plan dominates Silicon Valley. Most people think getting rich fast provides the quickest way to get past the first step — and where can you get rich faster than Silicon Valley?
p69
Here was a talent and a pleasure, I began to realize — the ability to put a blank piece of paper on the table and to create something in the context of work and business. I enjoyed sitting down, analyzing a problem, and then concocting a bunch of free-form solutions. I might have simply reinvented the wheel, made a hexagon instead of a circle, but I could get it rolling and I wasn’t afraid of venturing outside my realm of comfort and experience.
p83
The distinction between drive and passion is crucial. I had asked Lenny about his passion. He thought I was questioning his drive and commitment. Passion and drive are not the same at all. Passion pulls you toward something you cannot resist. Drive pushes you toward something you feel compelled or obligated to do. If you know nothing about yourself, you can’t tell the difference. Once you gain a modicum of self-knowledge, you can express your passion.
p92
I had begun to find aspects of the startup game increasingly disturbing. Expedience ruled. Sometimes I wondered if, rather than developing tomorrow’s business leaders and talent, we weren’t merely cloning speculators, hack businessmen and women, who arbitraged their drive for a quick hit and who believed that if you’re rich, you’re right. Heaven help us if these businesses actually have to be operated on a bottom line basis for the long run.
p104
TiVo had a chance to change the status quo for the better, with a potential we could only guess at. Sure, the market and business model were not yet proven, the incumbents could stonewall, and competitors large and small might hijack the opportunity, but Mike and Jim were up for the challenge: smart, experienced, flexible, capable of learning on the fly, and willing to do what it would take to win. They did not waste time talking to me about exit strategies. Personalized television would be their legacy.
p127
(on acquisition of Claris by Apple)… But it was a Pyrrhic victory. With our spouses, we all gathered at the home of one of the founders to celebrate our good fortune. Together we drank the celebration into a wake. We were proud of the price we’d gotten from Apple.. there was reason to celebrate — but when we looked around the room at each other, the deal’s downside hit us: it was unlikely we would ever work together again.
… I later realized what a rare privilege it had been to work with this group of people, in a place of our own making that gave us the opportunity to reach and stretch, to have impact, and to be great. Building a $90M a year, market leading business was a hard thing to do. Claris gave us, as a team and as individuals, a platform for growing and a chance to build a legacy and a culture that would contain our DNA in its values for decades to come. You couldn’t put a price on it, and I didn’t realize that until our company was dead and buried.
This may sound cheesy, but I feel like I’m incredibly excited to build a team, culture, and company at BettrAt like Randy experienced at Claris. Building a Bettr, sustaining business is so much more satisfying in the long run than a quick hit + sellout — at least from every one I’ve ever read about or talked to who’s built one.
p144
For me, the moral of the story of Steve Perlman and WebTV is the need to emphasize visionary leadership over management acumen in the formative stage of a startup. If you turn a visionary startup into an operating company too early, you throw out its birthright. It will never be as big, as grand, or as influential as it might otherwise be. It will be much harder, perhaps impossible, to expand the vision later, when performance is being measured quarter to quarter against operating plans, because then there’s too much at stake. Steve was the right leader, the only leader, to take WebTV through its formative years.
p156
Work hard, work passionately, but apply your most precious asset -time- to what is most meaningful to you. What are you willing to do for the rest of your life? does not mean, literally, what will you do for the rest of your life? That question would be absurd, given the inevitability of change. No, what the question really asks is, if your life were to end suddenly and unexpectedly tomorrow, would you be able to say you’ve been doing what you truly care about today? What would you be willing to do for the rest of your life? What would it take to do it right now?
p157
This is the creative edge of business – startups, working with a blank canvas to challenge the status quo and make change happen. I work with brilliant entrepreneurs who have a vision for how things can be better (Bettr? 
and who can’t resist doing the next great thing. I am their consigliere.
This is truly an awesome book (in this case, it was worth blogging about). If you want to change the world with your ideas, read it. I’ll let you open it rather than talk about “the riddle” here.
As Levar would say, you don’t have to take my word for it!
