Poker, Zappos, and the Writing Business

I have never bought a pair of shoes from Zappos.  I also don’t read a lot of business books, mostly because they bore me.

But I read Tony Hsieh’s book almost straight through because he’s cool.  He thinks outside the box even more than I do.  Like, it would never occur to me to write a sonnet in Morse code and say, “I’ll get an A or an F.”

I paid particular attention to what he learned from poker and applied to business.  A few struck me as applying to writing.  Click here to read his lessons directly on his website.

Now for my own 2 cents.


Evaluating Market Opportunities

.            Table selection is the most important decision you can make.

.            It’s okay to switch tables if you discover it’s too hard to win at your table.

  • If there are too many competitors (some irrational or inexperienced), even if you’re the best it’s a lot harder to win.


The table is crowded right now.  New York publishers are letting good editors go and the remaining ones are pretty gun shy.  I’m still keeping my hand in the ring.  I went to three major conferences in the past few months.  But I’m also open to the idea of switching tables, which is why I looked into radio drama.  Will it pay off?  I don’t know.  But if the traditional, straightforward methods aren’t working, I’m happy to go sideways.



  • The guy who wins the most hands is not the guy who makes the most money in the long run.

.            The guy who never loses a hand is not the guy who makes the most money in the long run.


I learned this lesson in “the Game” with Dean Smith, Kris Rusch and Loren Coleman.  Basically, Kris and Dean have a Master Class and the evenings are spent playing the game where you roll dice and pick random cards to establish your character’s traits.  For example, Karen Abrahamson, one of my classmates, ended up owning a Lexus and paying expensive rent, so she had to sell more books to make up for those costs.

I was lucky.  My expenses were moderate and I happened to write fast (6 books a year).  Steve Mohan, Jr., who happens to be a talented writer and all-around good guy, nicknamed me “Miss Six.”  But whenever Dean asked me if I wanted to risk more–say, roll the dice, and if I won, I could write seven books, but if I lost, I’d go down to five.  I’d always say, “No, thank you.”

Meanwhile, other people were risking more and getting up to my speed, but I didn’t care.  Steve called me risk averse, which is totally true.

When we had the end of class party, some veteran writers walked up to the board and said, “Who won?”

I found it a funny question.  “Gerry Weinberg made the most money and I sold the most books.”

Loren called my career “a typical midlist career.”  I sold a lot of books (won a lot of hands), but not for a lot of money each.  I got some good breaks, like one of my books got optioned by Hollywood, but I had to replace my roof twice, which wiped out some of that.

Was my fictional career a success?  Depends how you define a success.  But I’d have to say, although I didn’t lose many hands, I also didn’t make the most money.


Always be prepared for the worst possible scenario.

Not a problem for me.  Like I said, I’m always risk averse.  However, as Tony points out,

.            Go for positive expected value, not what’s least risky.

.            Make sure your bankroll is large enough for the game you’re playing and the risks you’re taking.

.            Play only with what you can afford to lose.

  • Remember that it’s a long-term game. You will win or lose individual hands or sessions, but it’s what happens in the long term that matters.

I’m slowly starting to take more risks.

For my book launches, this year, I ended up buying the books at an author’s discount and selling basically all of them (31 Indian Country Noir and 26 Dragon and the Stars).  I took the risk and I made the profit.

When everyone’s paid me for their copies, I should have approximately doubled what I made on straight short story payments.  I probably could have made more money by buying more copies and taking more of a risk, but we already know I’m taking baby steps at this.  Eric Choi pointed out that giving away copies can be good promo, which had honestly never occurred to me, so intent was I on making my money back.  But this time, I experimented on giving the occasional discount (once I’d made my money back) and the copy I’m shipping to Sandra Kasturi in T.O., I will only break even because shipping is prohibitive, but I figure it’s worth it because Sandra is a poetry editor and a reader and a way of expanding my audience.



.            Don’t play games that you don’t understand, even if you see lots of other people making money from them.

  • Figure out the game when the stakes aren’t high.


And now I’m looking at the future.

I have pretty much ignored e-publishing up ’til now.  I have written a bucketload of novels, but I had my heart set on printing them the traditional way.

I also have very little idea how to go about e-publishing–how to format it (Smashwords?), where to post it (sure, I want everything from Kindle to .pdfs, but this’ll take time), how to make a good-looking book cover (like pornography, I recognize it when I see it, but how do I create my own–book cover, I mean, not porn.  I ain’t that desperate.  Dean uses Powerpoint, but it’ll obviously be a learning curve).

Once I do feel comfortable, I’ve decided to put up some of my published work–short stories, poems, my medical non-fiction–and just have fun with it.   I’ve always kind of liked my photography.  Why not make a book cover out of some of my pictures?

If I make 35 cents on a 99 cent short story sale, cool.  If I don’t, I’ll live.  I’m pretty terrible at re-selling the rights to my stories because I can hardly manage to keep my encyclopedia of unpublished stories and novels in the mail (as well as aiming for 1000 words/day) without bothering about reprints.  This way, I’ll wet my feet in the e-market and maybe make a few bucks, but it’s the risk-taking that’s imporant and new for me.

One final word on Tony Hsieh.  One thing I like about him is that he’s not that interested in money.  He likes taking risks and building a tribe in pursuit of happiness.  He’s a millionaire, but more importantly, he seems happy.  His bio is that he lives in SF and “sort of has a cat.”

I’m no millionaire.  I’m not the richest doctor and I’m certainly not making a living off my writing.  But I know I would be miserable if my family consisted of a part-time cat, no matter how much money I made or how much my corporation and my friends reflected my values.  (I know he’s joking, but I’m just sayin’.)  I’d rather save a few lives, write and publish some good stories, and end the day with my sweethearts, none of whom are feline.

In the end, we are all authors of our own happiness, and that’s what’s most important.