Episode 20 – Learning the Art of Creating a Life While Making a Living – Lessons from a Startup VC

The Art of Creating a Life While Making a Living 

– Lessons from a Startup VC 

“And then there is the most dangerous risk of all- the risk of spending your life not doing what you want on the bet you can buy yourself the freedom to do it later”

“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?”

If you are one who believes you need to work the majority of life doing something you don’t want to do, so you can eventually retire and then devote your time to your passion then this book is for you.

This is the idea of the ‘Deferred Life plan’ – if there is only one thing you want to take away from this book then this is the one.

My parents lived their whole lives like this. There are people who go into something they don’t love but hope will make them enough money so that they would eventually do something else later

The problem is our life’s timeline is unknown.  We may never reach “one day.”

That step 1 you do what you must then step two do what you want – it implies that what we must do is necessarily different from what we want to do. 

Essentially the life we want cannot exist without doing something unsatisfactory? He calls out that while sacrifice and hard work is necessary as part of step 1, why not do it because it is meaningful and not just to get over it to move to the step 2.

He then talks about the Whole Life plan  – 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.

This is an interesting distinction that I had never thought of earlier. In reference to the steps in the Deferred Life Plan, drive is what you experience in the first step, and passion is what you hope to experience after you’ve put in your time.

“Passion pulls you toward something you cannot resist. Drive pushes you toward something you feel compelled or obligated to do.”

Chosen as one of the Top 100 Business books of all time, the book I referenced to is The Monk and the Riddle

I picked this up because I wanted to learn the inner workings of the silicon valley startups – from ideation to how they get launched, to how venture capitalists do deals to how plans get pitched an insider perspective from a startup investor. But I came out of it learning more than that.

Silicon Valley is filled with garage-to-riches stories and hot young entrepreneurs with big ideas.

This book describes the journey of one Silicon Valley insider has blazed a path of professional – and personal – success playing the game by his own rules.

Randy Comisar is a ‘virtual CEO’, a startup investor and provides ‘leadership on demand’ to several companies

The story opens with the author on a motorcycle journey through Miramar, where he meets a monk who poses a riddle:

“Imagine I have an egg and I want to drop this egg three feet without breaking it. How do I do that?”

It is a business book quite unlike the others, where instead of using a framework, Komisar takes us through a narrative of a dialogue between himself and would be startups.

It unfolds to showcase not just the inner workings of the VC and startup world but leaves one with differences between leadership and management, passion vs drive and finally what it means to succeed personally and professionally.

As Keynes postulated, in the long run, we’re all dead. Time is the only resource that matters.

Choose where you want to spend it.