Behind the Book Cover (Newsletter)

David Homan has a background so sprawling that introducing him almost broke the show: composer with seven albums, former head of a Bernie Madoff-sponsored arts foundation and now the person who quietly runs what may be the largest private network of “connectors” on the planet—2,800 of them and counting. His book, Orchestrating Connection, co-written with UC Irvine professor Noah Askin, landed at #2 on the USA Today bestseller list for business books the week it launched.

A listener asked me a two-part question: as she gets ready to publish her book and launch her speaking career, what’s the simplest, most economical path to having a box of copies on hand, and what should she budget to get there?

Most traditionally published authors go through a moment (or 100 moments) when they realize that their publisher isn’t actually doing anything for them. Some just accept that while others ask themselves the age-old question: can I get my rights back? That’s what a listener asked me this week: when a publishing contract expires, is it better to renew or get the rights reverted? I’m not a lawyer, and I don’t know the details of this person’s contract, but I’m naturally biased toward reversion.

Two of you sent me questions that looked different on the surface but landed in the same place: how to market a book under a pen name, and why past launches haven’t performed the way you wanted. My answer to both is the same. Lead magnets, newsletter lists and social media followers have done almost nothing for me, and the data backs it up. Justin Timberlake and Billie Eilish still had their books fail despite millions of followers, and Amy Chen sold just three books off a $10,000 TikTok campaign.

For some reason, I never really tell people I’ve been reviewing books on KATU TV/ABC Portland for years. I think I don’t tell people because I feel like I’m making it up when I say “I review books on TV.” It’s a weird thing to say. It’s a weird thing to do. Also, I feel like, well, it’s a local station and since I used to appear on so many massive shows, there was something a little like “Who cares?” about this.

A client of mine named Jimmie Applegate asked me a question I get from almost every author I work with, even though he was too polite to ask it quite this bluntly: he has a published book, Addicted to Failure, and a great Psychology Today feature to his name—and he still doesn’t know what to do next. Instead of answering him privately, I answered him on the show, because I know that so many other authors wonder the same thing. Jimmy got the press hit. That part’s done.

So last week I had the bucket list experience of being published by The Cut, as I told you guys. What I couldn’t tell you at the time because it hadn’t happened yet is just how much of a getting-sucked-under-by-a-wave-when-you-just-wanted-a-casual-day-at-the-beach experience it was. Look, I wrote the piece knowing the comments would be harsh. I’ve read pretty much every Cut story ever published so I know how vicious the commenters are.

Paul Colligan has written 13 books, is in the Podcasting Hall of Fame and has helped Donald Miller, Brendan Burchard, JJ Virgin and Joe Polish turn podcasting into what he calls a “grown-up business strategy” instead of a hobby. He also sent me a question I love: when you already have a working book, how do you know if it’s time to write a new one or keep leveraging the one you’ve got?

I worship New York magazine. Every bit of cultural awareness I have has come from the magazine or site. Any article of clothing I’ve bought in the past few years has probably been a recommendation from The Strategist. Writing for them has always felt completely out of my league. I never would have even thought to pitch them. But a few months ago I was having lunch with my friend Melissa de la Cruz—one of my writing career angels.

I’m trying something entirely new on the podcast. I asked you to send me your book questions and I’d answer them like the brass tacks book strategist I am, and the first person who took me up on it was Brenda. Brenda has three different book ideas in her head, a 100-page version of each, an abandoned memoir and a new instinct to pivot into the longevity market. I’m going to tell her to scrap most of it and write one big book instead. Here’s the case.