I publish essays about once a week on media, startups, creativity, and mindset.
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.
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.”
Jan 06, 2021
2020: A personal year in review
No doubt about it: 2020 was a lemon. But I still made lemonade.
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.
Dec 16, 2020
The inverted curiosity pyramid
A tried-and-true process to get maximum leverage from your content creation.
Dec 09, 2020
Dreamer, realist, or critic?
Walt Disney's creative process can help you make magic.
Dec 02, 2020
Acknowledging that the success paradox exists is the first step. The next and most important step is developing strategies to overcome it.
Nov 18, 2020
The sophomore slump
I know the success paradox well. I’ve fallen prey to its intoxicating effects.
Nov 11, 2020
The success paradox
The bigger the success, the harder it becomes to parse which inputs were most vital.
Nov 04, 2020
When life feels surreal
Reality now feels like we are living in a David Lynch movie.
Oct 28, 2020
Setting off on your own
If you find yourself stuck climbing the career ladder, get off and build an elevator.
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.
Oct 14, 2020
The leaky bucket
How Bleacher Report became an email powerhouse
Oct 07, 2020
Living with uncertainty
Uncertainty is everywhere. Here's how to deal with it.
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.
Sep 23, 2020
Startup lessons from the Dead
What can the Grateful Dead teach us about building startups? More than you'll ever know.
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.
Sep 09, 2020
Launch day always brings some unique feelings. One chapter closes, and countless others begin. There is anxiety. There is relief. There is possibility.
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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