Emotional Lessons From the Collapse of the Internet Bubble

My friend Dave Jilk recently shared the following Robert Frost poem with me.

Lodged
by Robert Frost

The rain to the wind said,
‘You push and I’ll pelt.’
They so smote the garden bed
That the flowers actually knelt,
And lay lodged–though not dead.
I know how the flowers felt.

That perfectly describes how 2001 felt to me.

We now have at least one generation of VCs and entrepreneurs who didn’t experience the collapse of the Internet bubble. Fred Wilson wrote a great post this morning titled Diversification (aka How To Survive A Crash). Fred does a great job of covering the financial dynamics around a crash.

But he didn’t really address the emotional dynamics.

In 2001, I was on the board of four public companies (and was co-chairman of two of them which I had been a co-founder of.) Sometime in the spring of 2000, all of them hit their peak stock price. By mid-2001 I think all of these were sub-$1 stocks and – if they weren’t – they would be soon.

The rain to the wind said,
‘You push and I’ll pelt.’

I knew my work world was totally fucked. I was working as hard as I knew how to work, dealing with a steady stream of failures. Amy and I were in a better place than the one I talked about in the beginning of our book Startup Life where we almost split up, but everything was still very rough around the edges.

My moment of capitulation came sometime in the early summer of 2001. For months, I was going to bed each night with the thought “tomorrow will be better.” By summer, it was warmer, but one night, as I was crawling into bed, I realized that each day had been worse, and often much more punishing than the previous one. The cumulative impact of what by that point was over a year of an intense, downward spiral in every aspect of my work world, was undeniable.

Forget about the paper money, much of which had vaporized. I was just completely exhausted hoping that something would break my way.

They so smote the garden bed
That the flowers actually knelt,
And lay lodged–though not dead.

That night, I changed my perspective. Instead of hoping the next day would be better, or easier, I went to bed thinking, “Fuck it – let’s see what the world will throw at me tomorrow…” If you’ve read my post from 2015 titled Something New Is Fucked Up In My World Every Day, you will recognize this philosophical shift.

I know how the flowers felt.

Eventually, it got better.

I wasn’t dead. Someday I will be, but I wasn’t then. The pelting eventual stopped. Lots of things I was working on were smote, but the sun came out and I kept at it.

Every successful entrepreneur I’ve ever met has stories like this. Every successful long-term VC has had these moments, sometimes for extended periods of time.

Just like Fred suggests you diversify financially, you should diversify emotionally. I have no idea how I would have survived this period without Amy. When I reflect on my relationship with Seth, Jason, and Ryan much of the intense loyalty between us was forged in the period during and after the debacle that was the collapse of the Internet bubble. Some of my lifelong friendships, with people like Len Fassler, Dave Jilk, Rajat Bhargava, Jenny Lawton, Will Herman, Ilana Katz, and Warren Katz were solidified by the intensity of this time frame.

Until that day in the summer of 2001, my emotional well-being was much too connected to my financial well-being. The day after, not so much …


Also published on Medium.