“Who Cares?”

Why I created Iteration

James Do
Iteration
3 min readAug 19, 2020

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From the moment I joined Medium as a writer about a month ago, it was perhaps inevitable that I’d create my own publication before long.

Medium is a bit like the job market, and there’s no one right way to go about it. You can try to work with existing large publications. Or, you can start your own little publication.

I started my first business when I was 15. My best friend Michael and I were policy debate partners in school, and in sophomore year we decided to create a debate course to make a little money.

We christened it TD Debate Camp (our last initials), photoshopped a flier, printed a stack of copies (color), and confidently headed to the nearest tiger parent congregation (Asian grocery store). After a long day of passing out fliers in the parking lot, we waited. Days passed. No inquiries.

Not content to give up, we set up a meeting with the owner of a local tutoring center, and pitched her our idea for a public speaking and debate course. She liked our concept, and offered to pay us $20/hr for us to teach our course there. For a couple of high schoolers in 2004, that was a lot of money.

But with dollar signs in our eyes, we countered at $40/hr, and she politely and very understandably shooed us off her property. Other priorities started taking more of our time, and that was the end of TD Debate Camp.

It’s one of my most cherished memories from high school. I still find it hilarious that our flier featured a picture of us, scrawny arms folded across our chests, donning shades (thanks to Photoshop, they were the same pair of Michael’s Ray Bans, because I didn’t even own sunglasses at the time). I’m still amazed that, despite our nonexistent track record in teaching debate, we managed to secure an offer representing three times the pay our friends were eking out as math tutors in the same center. I still smile, sometimes a little misty-eyed, when I recall our childish, unbounded ambition in turning it down, hoping to score just a little more.

I’m now twice as old and a good bit wiser. But there’s some deep wisdom there, in the beautifully carefree way Michael and I started and ended our first business together. Something that I have to work never to forget.

It gets harder, the older you get. You have more to lose, more ego to protect. But not keeping that playfulness — that sense of Who Cares? — alive is what kills young men and women decades before they die.

As a new Medium writer of barely a handful of articles, I found myself already worrying too much what the editor of a publication might think of each new story.

No, I’m the only editor whose opinion should matter when I write.

And that’s why I created Iteration. It’s my way of experimenting, without worrying about what others will think. If you enjoy the stories here, awesome. If not, you’ll know at least I did.

The author and his best friend at a high school debate tournament, circa 2004.
Me (left) and Michael at a debate tournament, circa 2004. Definitely posted without his permission.

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James Do
Iteration

My life’s work is to help people discover and focus on theirs. Founder of Cortex Education. Investor. Former attorney.