Delivering Happiness

Dabbling
As I tried to figure out what I wanted to do next, I ended up doing a whole
lot of dabbling. I dabbled in “investing” and day-trading, putting money
into the stock market in companies that I knew nothing about, and ended up
losing a lot of money. I decided to invest in a movie called Christmas in the
Clouds, in which I had a small cameo role. I ended up losing a lot of money
in that too.
They were expensive lessons, but I guess what I ended up learning was
that it’s a bad idea to invest in industries you don’t understand, in
companies you don’t have any control or influence over, or in people you
don’t know or trust.
Over time, I also kept asking myself why I was investing in anything at
all. What was my goal? To make more money? That didn’t make sense,
since I had already given up a lot of money when I walked away from
Microsoft.
I realized that the day-trading and investing I was doing weren’t really
fulfilling. I didn’t feel like I was really building anything. It felt more like I
was gambling, but with the odds stacked against me because I was investing
money in things I didn’t understand. I ultimately made the decision to pull
out of almost all my stock market investments and to try to figure out
something more meaningful to focus on instead.
I had been checking in every week or two with the folks at Zappos,
offering advice (especially on the technology side) as needed. It was just a
handful of people working at Zappos, but they were making good progress
for such a small team.
Alfred and I introduced Zappos to Michael Moritz at Sequoia and helped
set up an initial meeting. We felt good. The Zappos team was passionate
about what they were doing, they were making great progress, and Alfred
and I had talked up Zappos to Sequoia in our e-mail introductions to them.

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We assured the Zappos folks that the meeting was more of a formality than
a pitch. With their LinkExchange investment, Sequoia had turned a $3
million investment into over $50 million—basically multiplying their
money by seventeen in just seventeen months. Alfred and I had credibility,
and in our minds, it seemed like a relatively small thing to ask Sequoia for a
few million dollars to put into Zappos.