I publish essays about once a week on media, startups, creativity, and mindset.
May 05, 2021
Purpose, then process
With any creative effort, there is an important order of operations to follow.
Apr 28, 2021
Why newsletters work
They're simple, efficient, and perhaps a bit overhyped. But why are newsletters such an effective medium?
Apr 21, 2021
Feel like a stranger
I journeyed down the web3 rabbit hole, and found a tantalizing future for media.
Apr 14, 2021
Let things unfold organically
Creators are often told that consistency is a key virtue. But that’s not the whole story.
Apr 07, 2021
Connecting the dots
A great story has the power to stretch time and bend the cosmos. Here's how to tell yours.
Mar 31, 2021
Forget creative genius: pursue craftsmanship
You don't need to be a genius to create, and you don't need to be tortured to be an artist.
Mar 24, 2021
A content strategy fit for Bubba Gump
Forget "fish where the fish are." To find your audience, you need to fish where no one else is fishing.
Mar 17, 2021
Get on the bus!
There are times when something big, something beyond description comes along. And you’ll face that question: do I get on the bus?
Mar 10, 2021
Slice it thin
How to generate an endless supply of content ideas that will help you build your audience.
Feb 24, 2021
Planning the perfect personal retreat
How to reclaim your time, rebalance your energy, and become one again with the Force.
Feb 17, 2021
No excuses: Create something
How to silence your inner critic and embrace creativity.
Feb 10, 2021
You’ll know when it's time to sell your company
In a landscape overflowing with hustle porn, startup acquisitions are the money shot.
Feb 03, 2021
Surrender to the flow
The world is full of distractions. Flow is your reward for tuning them out.
Jan 27, 2021
Media liquidity is back, baby!
SPACs and creators are bringing the fun back to media.
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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