[BBD Prologue] Introducing the Billion Dollar Diary

There is a famous question getting thrown around all the time that is supposed to cure people’s fear of failure: “What would you attempt to do if you knew you would not fail.” My first thought was, “that’s a terrible question!”

If I could not fail, I would concentrate my effort working on building things that have the most impact on humanity – an air spray that make everyone kind and loving, a time-traveling virus that targets only Hitler, or a foot massage shop on Venus. But in the real world, I would fail, and I would be wasting time doing these things, and that has to be part of the calculation.

My second thought was, “who said this?”

After some googling, I saw the name, Robert Shiller. I thought, “wait… Robert Shiller? The Yale professor who came up with the Case-Shiller Index? Interesting… I would not have predicted an inspirational, touchy-feely quote from someone extremely rational, like a Nobel-winning economist who predicts upcoming housing crashes.

Then I dug a little deeper. No, it’s not Robert Shiller. It’s Robert Schuller! A “positive thinking” motivational speaker and televangelist famous in the 70s! Now that sounds like a guy who would say something like that.

Now, a better question should be, “what would you do anyway if you knew you would fail for sure?”

Now that’s a tough one. I thought about it for a long time… and I need to be honest with myself. My answer has always been “to build a $1B company that makes people better.”

In noble terms, it’s an enterprise with a double bottom line.

And in Silicon Valley terms, it’s called a unicorn that poops ice cream. (Seriously, there is a life-changing product whose ad is based on this image.)

I could give some grandiose reason for choosing this venture even if I knew it would fail. But the answer is straightforward – it’s fun and good! I believe in the journey more than the destination. I believe that success, beauty, and joy are found in the wins and struggles along the path, even if the final stop is a dark, cold, and lonely void. It’s like when Jack found Rose on the Titanic and became the ultimate winner in life, even though the ship sunk and Jack’s worldly fate was the most handsome fish food in history.

I am writing this blog to capture the beauty and folly of an entrepreneur and his ongoing journey to build a $1B company. I am calling it the Billion Dollar Diary.

I fully understand that this blog which likely no one will read, is about a venture that will surely fail. (Who reads blogs in 2020’s anyway?) But you know what? Dreaming is fun! Company-building is fun! And writing is fun! I am going to do it anyway, no matter the outcome. If you happen to stumble upon this blog and find it enjoyable or insightful, let me know. And if not? Who cares anyway?