Essays

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

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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