Success hides your mistakes

(written by lawrence krubner, however indented passages are often quotes). You can contact lawrence at:, or follow me on Twitter.

This is a great interview with Tim Brady of Yahoo:

Craig : After you closed those first ad sales were you all still freaking out over if this would be viable to not?

Tim : It was probably a full year of discomforting uncertainty. Even after we brought Tim Koogle in, it wasn’t a sure thing. The Internet was a sure thing but Yahoo wasn’t a sure thing. It probably took until the end of ‘95 to guarantee that.

Craig : Interesting. Did how you feel about the company change as you scaled?

Tim : Nope. I was all in the whole time.

Craig : How long did you stick around?

Tim : I was there until 2003.

Craig : How was it to ride that wave, especially when the bottom fell out in 2000?

Tim : When things are going well and you’re in a growth industry, you don’t have to deal with many difficult issues. It’s the old cliche, winning solves everything.

Craig : For sure.

Tim : It’s really true. It solves everything… or maybe better said, it masks all your mistakes. A lot of the mistakes you make get masked because you receive almost no negative feedback.

But then the bottom fell out and the board let Tim Koogle go. The upper ranks of management emptied out pretty quick, except for me and the CTO who stuck around. We got a new CEO and set of peers in upper management. Let me just say, I learned a whole lot more about business on the way down than I did on the way up.

Craig : When you think back on your time at Yahoo, how do you feel about it?

Tim : Well, I definitely made some of my closest friends there. I compare them to childhood friends. I can pick up the phone and call any of 50 people and talk to them as if no time had passed. It’s a pretty cool feeling.

Craig : That’s really neat.

Tim : It was formative in so many different ways. Granted it was early in my career, but then again most of the entrepreneurs at YC are early in their careers, too. It’s this intense experience where for the first time in your life where you’re defining your own test and seeing if you measure up. You find out a lot about yourself in that environment.

Craig : I imagine it really builds confidence.

Tim : It does.

It was certainly career defining. The financial success was nice, but it was way more than that. The entire process helps define who you are, what you’re good at, what you want to do, and what you think is important.