Essays

I publish essays about once a week on media, startups, creativity, and mindset.

Getting Started Jan 20, 2021

How to make money on the internet, circa 1998

My life changed forever when, as a teenage nerd, I discovered how to make money on the internet.

Startups Jan 13, 2021

Your startup is not your baby

After I sold my first company, people would say to me: “That’s like giving away your baby.”

Life Jan 06, 2021

2020: A personal year in review

No doubt about it: 2020 was a lemon. But I still made lemonade.

Media Dec 23, 2020

How Bleacher Report found our first writers

How a handful of friends started a sports blog and built it into a community.

Creative Process Dec 16, 2020

The inverted curiosity pyramid

A tried-and-true process to get maximum leverage from your content creation.

Creative Process Dec 09, 2020

Dreamer, realist, or critic?

Walt Disney's creative process can help you make magic.

Mindset Dec 02, 2020

Fresh eyes

Acknowledging that the success paradox exists is the first step. The next and most important step is developing strategies to overcome it.

Startups Nov 18, 2020

The sophomore slump

I know the success paradox well. I’ve fallen prey to its intoxicating effects.

Startups Nov 11, 2020

The success paradox

The bigger the success, the harder it becomes to parse which inputs were most vital.

Life Nov 04, 2020

When life feels surreal

Reality now feels like we are living in a David Lynch movie.

Startups Oct 28, 2020

Setting off on your own

If you find yourself stuck climbing the career ladder, get off and build an elevator.

Mindset Oct 21, 2020

I have an unfortunate announcement

I am a fraud. An impostor. My entire career – my whole life really – has been built on lies and deception.

Media Oct 14, 2020

The leaky bucket

How Bleacher Report became an email powerhouse

Mindset Oct 07, 2020

Living with uncertainty

Uncertainty is everywhere. Here's how to deal with it.

Media Sep 30, 2020

Why media companies should be direct to consumer

It doesn't matter what trend you chase, growth hack you engineer, or platform you build on.

Startups Sep 23, 2020

Startup lessons from the Dead

What can the Grateful Dead teach us about building startups? More than you'll ever know.

Startups Sep 16, 2020

The arrival fallacy: What it feels like to sell your company

It should have been one of the best days of my life. And yet on the day the deal closed, I felt depleted.

Mindset Sep 09, 2020

Launch day

Launch day always brings some unique feelings. One chapter closes, and countless others begin. There is anxiety. There is relief. There is possibility.

Creative Process Sep 02, 2020

Making things and putting them on the internet

Last year, a friend who runs a middle school in Red Hook, Brooklyn invited me to speak to a group of eighth graders at their career day. My fellow speakers were an education administrator and a pharmaceutical salesperson. Compared to them, my career arc was a little harder to explain.

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