I Quit My Job (Again)

When you start a startup, it looks like this:


The idea is oblong and awkward. Then you have a small victory, and it stands upright:

With each successive rotation the edges get smoother. It starts to take shape:

Then rounder:

When a startup turns into a wheel, we consider it in “high growth stage.”

But what turns a high growth startup into a rocketship?

Something counter-intuitive; the startup tucks in the wheels.

…then it takes off.

Introducing my new passion, ArtSpot.

Closing Tabs

This weekend I wrote a parody to “Closing Time” by Semisonic, inspired by my experiences with Google Chrome.

Check it out:

Happy Sunday.

On auditioning

In Donald Glover’s stand-up special Weirdo he says:

“No matter how “famous” I get, people always ask me to audition. This is strange to me because I can’t imagine walking on set one day and forgetting how to act.”

Before hearing this I assumed A-Listers “just show up” and everyone else has to prove their worth. Thanks to a bit of research, it turns out I was wrong. Sometimes A-Listers screen test, sometimes C-players hook a gig after lunch with the producer.

Shortly after watching Donald’s routine, an interesting marketing opportunity called my bat line. The next step was to submit a formal application.

But rather than core questions like “how would you make X better” or “what’s your approach,” the application insisted I send mind-numbing (and unrelated) research to an intern. I declined.

From this experience I realized auditioning has little to do with skill and everything to do with skill perception. Your work should speak for itself, and great managers can synthesize past performance into future potential. Hint: bad managers can’t.

In 2015 I’m going to do a better job of a) helping managers see my value, but also b) swallowing the occasional pride pill with a song and dance routine.

I hope you do too.

The problem with startup PR

So the young startup wants a feature in TechCrunch.

They hire a PR girl (or guy, but let’s be serious) and a few $10,000 retainers later, they land VentureBeat and Gawker.

No TechCrunch, but oh well. That’s a scam pub anyway, right?

As traffic hits the servers, a team member sacrifices her Apple monitor for dedicated Google Analytics watching.

Some signups happen.

A month later the press is buried, traffic is normalized (zero), and the team ponders what to try next.

“How about marketing?” someone suggests.


Marketing should be the first investment, not the second.

PR’s function is limited — it amplifies success. But growth marketing helps understand users, fix products, segment audiences, and optimize messaging. (Great ingredients for a strong PR campaign, no?)

Yet young startups would rather expense a PR team to amplify a shitty product than invest in marketing to help make it better.

You can budget accordingly or die with your name in headlines.

Your biggest fan

In high school I started a band and our first show was downtown. Tickets were $6 each.

When I started selling them I anticipated some no’s. People are busy and I get that.

Then I got lots of no’s. Friends said $6 was expensive and that Atlanta was too far away, despite their allowance being 5x mine and their frequent weekends in the city.

This was my first exposure to people not believing in me.

Then I graduated high school in May 2008. While my friends flew to college that Fall, I drove to North Carolina and spent my life savings recording a solo album.

My website was all like,

“Do you want to pre-order it?”


“Here’s a link.”

–radio silence–

My third experience was Nov 2012, when I wrote a book and launched a Kickstarter project to fund the publication.

Things were different now, I thought, because everyone grew up and had jobs and disposable income.

Emails to friends were all like,

“Do you want to pre-order it?”


“Here’s a link…”

You can guess what happened next.

When you do entrepreneurial stuff, you’ll probably need funding. Art projects, product launches, mission trips, whatever. All cars need gasoline before they run.

Counterintuitively, you won’t learn if all those people rooting for you actually believe in what you’re doing until after you ship. This is because it’s free to support ideas but a burden to support execution.

I said before that entrepreneurship is the ultimate heartbreaker.

Not software, design, or operations.

Those are functions, while entrepreneurship is the aggregation of resources (belief) and the transformation of those resources into an area of higher yield (profits, attention, social good, etc).

So something entrepreneurs experience that other people don’t is the incessant pulse of how much (or little) people believe in them.

And that begs a critical ingredient of entrepreneurship– you have to be you biggest fan. But you also have to be your biggest critic.

Because to be good at your craft requires experience. And failure begets experience 10x more than a pat on the back.

So you have to fail all the time, believe in yourself anyway, ship stuff that everybody might hate, and then improve.

That’s entrepreneurship.