"What was your biggest Dip?"
I've had lots and lots of Dips, which is really lucky for me.
There are plenty of people I went to business school with who have been on a dead end ever since. There are plenty of people who I worked with at my first job, who have been at a dead end ever since.
What I have tried to do is seek out Dip after Dip. Now, there have been a few times when I've quit in the Dip and regretted it. There have been a few times when I almost quit in the Dip, and managed to just squeak through. Just before I sold Yoyodyne to Yahoo in 1998, the good news is the day before we sold, we were profitable which was very unusual in those days. The bad news is that in the six weeks before we sold, there were three occasions where we almost missed payroll. We were within an hour of not having the money in the bank to pay our employees.
And it would have been really easy in those days to give up. To look around at the well-funded companies that had raised twenty or forty or eighty million dollars. We had raised four. To look at the companies in California that were getting great deals and hook-ups because of who they knew, and we were in New York and knew no one.
And, it would have been easy in the pressure of the moment to say, "Well, we gave it a good try. Let's go home." I'm really glad we stuck that Dip out.