How Chris Dixon helped me handle Fear

Thanks dude!

Thanks Chris!

Oh shit.

That’s all I could blurt out. I was at the ATM staring at my Chase business checking account balance and the number staring back at me was $500.

Oh shit.

An $8,000 bill that my business owed was scheduled to post tomorrow. Earlier in the day, I hounded a client about a slightly late payment they owed for a big marketing campaign. The VP I spoke to curtly assured me that the payment would arrive the next day.

Oh shit.

Running through the logistics in my head, the mailman arrived at my office every day around 3:00 PM. That gave me about two hours to collect the client check (assuming that it indeed would arrive) and deposit it in the bank. If the $8,000 bill posted at the end of the day, I’d be okay. If it posted earlier, then I’d now have to deal with a bounced check, which was sure to create headaches for the line of credit I had applied for at Chase…


I went through thousands of moments like this when I was running my startup. Fear was a daily part of my life. I felt it all the time in the form of a constant pressure in my chest relentlessly pushing harder and harder.

Life as an entrepreneur is terrible. 99% of entrepreneurship is depressing, where it feels like the house of cards you’ve built for years will collapse at any moment from the smallest thing. As Jess Lee aptly observes, it’s no wonder why startup founders are always unhappy.

But then there are those 1% moments when things go right. It’s absolute exhilaration and perfection—probably like what I imagine heroin feels like.

As a startup founder, I’ve dealt with Fear and burnout more frequently than I would like to admit over the 7 years I ran my company pre-acquisition.

During a particularly tough moment in my startup journey, I had an epiphany. Well actually it was not my own epiphany. I came across a piece of writing that perfectly characterized my Fear and simultaneously explained why I do what I do.

It was a short blog post written by Chris Dixon, a serial entrepreneur turned venture capitalist. Here’s what it says:

Two Kinds of People

Click to enlarge.

(check out more awesome posts on Chris Dixon’s blog)

I’ve never met Chris before. But in 253 eloquent words, Chris spoke directly to me by summarizing my entire journey as an entrepreneur and reiterating why I forced myself out of bed every morning for more pain. I was trying to build something new; something great that would change the world.

I’ve kept that screenshot of Chris’ inspirational blog post on my desktop for the past three years. And I read this message almost every day.

Chris’ blog post didn’t remove the Fear that gripped me every day, but it did remind me of my Purpose. Whenever the Fear felt overwhelming, I would take a minute to read this post on and then carry forward. I was able to stick with my startup and eventually make it to the finish line.

To entrepreneurs reading this post: I understand your Fear. Take note of Chris’ words. Know that you have a Purpose and remind yourself that you are bringing something new and great into the world. That’s worth fighting for every day.

To Chris: Thank you, so much.

1 thought on “How Chris Dixon helped me handle Fear

  1. rea

    Thanks for a marvelous posting! I genuinely enjoywd reading it,
    you are a great author.I will remember to bookmark your blog and will often come
    back sometime soon. I want to encorage onne too continue your grea work, have a
    nice weekend!


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s