What was a “turning point” in your life, where you were at a mental crossroads and had to make a life-changing choice? How did you choose, and where do you think you would be now if you had made the other choice?



I was a lawyer for 22 months in the go-go days of Web 1.0

I was a pretty terrible lawyer. You can’t be a good lawyer if you lack attention to detail (one of my weaknesses), that’s for sure. But my clients loved me, because I loved start-ups and it was in my blood, and because I did whatever it took to deliver. I had a passion to help founders succeed. I worked harder, and more importantly, took ownership where others wouldn’t. I got it done — and I believed.

One day, a very prestigious VC came up to me in a parking lot on Sand Hill Road and asked me if I would represent all his investments. (I had worked with him on a few start-ups before that).

That would be a pretty plum piece of business for a young corporate attorney to bring in, in his second year.

I had a pause. I could then see the future. I saw I could bring in business, I could be successful on the track I was on. And I saw it wasn’t a track I wanted to be on.

I walked in the next day, and quit. That future — once I knew what it was — it wasn’t my future.

I had no job prospects, and no savings, a ton of grad school debt, a mortgage, and no idea what I wanted to do next. My wife was kind of shocked.

But I just needed to get back into startups and software and the internet.

The one thing I did right was give 60+ days notice. I finished helping on a $2b+ acquisition, an IPO, and a bunch of other matters. (And in fact, doing so end up costing me a huge amount of money).

But during those 60 days, in a rare bit of positive karma, three of the startups I’d worked for offered to bring me in in senior roles. I took a big pay cut and joined one of them, and a few years after that, had enough semi-experience to start my own.

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Published on November 8, 2017
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