So You Want To Write A Book?

This article format is an experiment. Instead of fleshing this out in 2,400 words, I’ve just summarized the points, leaving out the nuance.

My Experience w/ Book Writing

Managed an academic publisher (Eisenbrauns) for 5 years, later sold to Penn State.

Offered three (sh1tty) publishing contracts and turned them all down.

Started a publishing firm back when self-publishing was stigmatized and published 30+ books from other authors under that imprint. (We closed it after the need passed.)

Six-time author, four of which are good.

Should You Write A Business Book?

Do you have a very specific idea that you are totally committed to sharing with the world so that hundreds/thousands of people can benefit from your thinking without ever hiring you?

Do you have the discipline to stick with something for a couple of years?

Is there substantially more to say than can be said in a longish, two-part article?

Missing from this list: writing it, selfishly, to be famous or rich. Those are terrible reasons, and the books are awful.

Do You Want It To Be A Better Book?

Throw big parts of it away.

Make what’s left a lot shorter.

Get a good editor who is not afraid of you and who doesn’t mind making you work hard.

Let your own unique use of grammar and cadence shine through. Be different.

Illustrate it.

Read it yourself, if you can, with great audio gear and editing.

Do You Want It To Be Successful?

Do you already have thousands of followers, who are addressable and can be told about the book? And because they know you, they really want to read it?

Do you care if you don’t make any money? The rule of thumb is to give 1 away for every 2 you sell.

Do you realize that you’ll have to do all the marketing? Including stupid podcast appearances where some hosts clearly haven’t read the book and mainly ask the same questions?

Remember that design and format matter. Unless you’ve designed hundreds of book covers, do not try this at home. I’d recommend faceout studio.

If there are going to be Audible and Kindle versions, release all three formats at once.

Do You Want It To Be Successful For A Long Time?

Read Ryan Holiday’s Perennial Seller.

Make sure quality is more important than marketing.

Stay away from fads/trends. Write something that’s evergreen.

Solve a big human problem that will always be with us.

Test it exhaustively in the marketplace before release.

Do You Want To Be Respected By Real Authors?

Careful on the bestseller and award-winning claims. Those folks know, just like you, how they can be manipulated. To be an Amazon bestseller, you just need to dominate a single, narrow category for 24 hours. It ain’t hard. And “best-selling” is as meaningless as “award-winning.”

Properly credit your sources and influences. It’s honest and gracious.

Write a book so good that people want to write a blurb and don’t grudgingly agree.

What Should Your Expectations Be?

For most people reading this, their first book will be self-published and will sell 2,400 copies over 5 years. That’s way above the average. Say it’s priced at $24.95, and since you’ll give away one-third of the copies, the remaining 1,600 will sell on Amazon, where you’ll receive 45% of the list price, or $18,000.

From that $18,000, you’ll probably design it yourself (a mistake) and pay $10,000 to print it (POD should be your last choice). From that you’ll pay fulfillment (shipping and supplies), a failed promotional effort of $5,000, and a vacation to Costa Rica for $4,000 to recover from the effort. That’ll leave you $1,000 from your investment, not including about 800 hours, probably, of labor. So you’ve made $1.25/hr. Like I said, it’s not about money. If money comes, be thrilled. My revenue from books is probably $500,000 over the years? I don’t care and that’s not why I did it.

Or you can use a hybrid publisher for $25-40k and have them very reliably publish a very ordinary book with no more input from you than you want. Their editing won’t improve the book much, but you won’t have to mess with the logistics and they’ll get you in some bookstores where it won’t sell anyway. It’s an excellent choice if you don’t want to view self-publishing as a fun adventure.

But ignore all that, because it’s the unmeasurable stuff that’ll keep a smile on your face:

  • A bit more credibility when prospects are comparing otherwise equal firms/people.
  • A half dozen speaking engagements you wouldn’t have otherwise had, each of which delivers two clients.
  • Envy from your neighbors. Misplaced, but still envy.
  • Hatred from your competitors. This is priceless, indeed.

But even if none of those things materialize, here are the two things that people can never take away from you:

  • You have spent a lot of time with a key concept and now you know it so much more confidently.
  • You will have helped hundreds of nameless people figure something out, leaving the world in a better place.

Finally, It would be legitimate to do everything your own way—that’s kind of how you got this far anyway—but if you want to pursue a very good education on writing a business book, or even work with a top expert, check out Josh Bernoff.

My Favorite Quotes About Writing:

“Nobody ever became a writer just by wanting to be one. If you have anything to say, anything you feel nobody has ever said before, you have got to feel it so desperately that you will find some way to say it that nobody has ever found before, so that the thing you have to say and the way of saying it blend as one matter—as indissolubly as if they were conceived together.”

―F. Scott Fitzgerald, letter to his daughter, October, 1936

"I don't really teach. I talk about things that I care about to those who are ready."

—Transparent, Season 2, Episode 5, Mee-Maw, teacher at Berkley

 “I do not so much write a book as sit up with it, as with a dying friend.”

  —Annie Dillard

“The moment that you feel that, just possibly, you’re walking down the street naked, exposing too much of your heart and your mind and what exists on the inside, showing too much of yourself. That’s the moment you may be starting to get it right.”

  —Neil Gaiman, commencement speech at University of the Arts


The four good books I’ve written (I’ll leave the other two off the list):

  • Managing (Right) For The First Time (2010)
  • Financial Management of a Marketing Firm (2010; revised 2023)
  • The Business of Expertise: How Entrepreneurial Experts Convert Insight to Impact + Wealth (2018)
  • Secret Tradecraft of Elite Advisors: Covert Techniques for a Remarkable Practice (2023)

Two in the works:

  • Building a Sellable Professional Services Firm (2025)
  • Nashville Falling (2026, a novel about a long slow slide into homelessness)

  • Secret Tradecraft of Elite Advisors

    Secret Tradecraft of Elite Advisors

    Covert Techniques For A Remarkable Practice

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