My friend just returned from the Dominican Republic. He is a photographer and took dozens of pictures from his stay in Santo Domingo. One house in particular fascinated him. A gorgeous palace of stone and brick, with a beautiful wooden interior. It was built a few hundred years ago by a wealthy man from Italy. His daughter missed their home country and he had this house built in an Italian style to remind her of home. The father would have spent a fortune on this building.
This got me thinking. A millionaire by today’s standards and he is still making decisions on basic emotions. His daughter cries for home so he pulls out the purse and provides work and the livelihood for the architect, suppliers, and laborers on a massive project. Imagine that – his want to make his daughter happy supported hundreds of people because of his decision.
Now imagine Ebay’s former CEO Meg Whitman championing the purchase of Skype for $2.6B. Everyone around her agreeing to it, an $8.5B bureaucratic machine of lawyers and bean-counters mobilizing to make this happen. In the end it was a bad decision, a poor fit. Should have never happened.
What emotions were at play here? What basic feelings made her and the people around her go through with this? Whatever they were they weren’t enough. The real issues weren’t strong enough on the table, and the quest was wrong.
Infochimps is still a small startup, and any decisions we make only have a swath of 3-10 people. But it is so important for us to maintain our focus while we burn cash. A slight deviation from the course at this stage can lead to a difference of hundreds of miles at the end.
I try to ask these these questions whenever an important decision is on our minds. What is really pulling us in this direction? Where are there biases? Why should we do this? What would our advisors say? What could this mean 6 months, 1 year, and 5 years down the road? What have we learned from decisions like this in the past that can make this experience better?
Joseph Kelly's Blog 
I just think it’s amazing. To have all the cash you could ever want at your disposal, and you’re still making decisions on base emotions.
Belief that getting rich will somehow solve all your problems is wrong. You will not be able to avoid wasteful and irresponsible behavior unless you practice good decision making while on the road there.
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