Tom Gates' Wayward Is #1 Bestselling Travel IBook

Published in February, Wayward has quickly blown up on Amazon and iTunes. I couldn’t be more stoked for Tom and asked him about it earlier today.

[DM] Dude your shit is blowing up. I saw where you’re leapfrogging Jon Krakauer and about to take down Rick Steves in the iTunes travel ebook bestseller list and crack Amazon’s top ten travel essays. Did you have any idea it would happen so fast?

[TG] I have no idea what the fuck I’m doing, really. I made this plan in my head that was built on how I’ve self-released music from bands that I’ve managed over the years. And what I learned at Matador. I know promotion and marketing, so I just applied everything that I knew. The idea was to put it out quietly on Kindle and Amazon, then garner a few reviews, then slowly come out of the closet with the book. I ended up coming out faster than a lispy 16-year-old dancing to Gaga at junior prom.

I hadn’t really told my friends and family that the book was coming, and I was a little nervous about the more risqué stuff in there. Aunt Becky will surely have a heart attack. But once it flew out there I just embraced it and put it up on my socials, and here I am. I’m trying not to obsess about the charts but I did take a screen shot now that it’s #1.

Take us through the timeline of putting this book together. I remember you working on these pieces throughout your editorship at Matador, but then it seems like there was an extended “incubation period” afterwards which really helped refocus your work overall. How did this all go?

I came back from my 12 countries in 12 months trip and then dove right back into the music business. The music business is overwhelming, to say the least, and my first artist back just shot right out of a cannon. I rode the cannonball too.

I couldn’t figure out how to do both, so I put the editing and writing aside. Then I fell apart because of it. Anyone who writes laughs when I tell them this — if you just stop cold, it’s a bad shock to the system. So, I actually went to a writing coach and set up a schedule where I wrote in my underwear at night and worked in my clothes during the day.

I wrote a few of the things after the trip and resurrected a few other pieces that hadn’t been finished. I killed about 10 other pieces. My roommate at the time would just look at me, zombiefied, like why the hell are you doing this to yourself?

I know you had some publisher interest in the manuscript. What was it, in the end, that made you decide to publish this DIY?

I’d sign with the right publisher in a second. The interest just wasn’t strong enough and I’ve seen so many artists sign deals with record companies that are sniffing-level interested. They end up working at gas stations on interstates.

My friends make DIY records and start DIY record companies. I grew up around this culture and have run so many of my artists’ record labels. I have no fear about winging it, despite only a shot glass full of knowledge on the book business. If I can sell 100,000 records with only the outreach I know, why can’t I sell a thousand books?

The fear creeps in with the possibility that it could do more than that. There’s no big button to push on my desk. That’s where the Hand of God that being with a big publishing house is helps.

There is something really neat about my first book being exactly what I want it to be though, flaws and all. It’s like my killer first EP, rough around the edges, with messed up Oxford commas and everything. My friend Sam made the cover, and it’s just so me and exactly what I wanted the aesthetic to be.

For fans of your writing on Matador, what new bits and surprises can we expect in Wayward?

There are a couple of pieces in there that seem to really connect, and they crushed me to write. “On Drowning” is about this incredible band that I managed who broke up on the same day that I witnessed a death, and how it spun me around in six different ways.

I’m probably most proud of “Woe Was Me.” I never thought I’d write a story about coming out, let alone this incredibly secret affair I had with someone I met on the internet, back when the internet was brand new.

It’s scary as hell to put these down and out into the world. I don’t know if I’m even at peace now with that concept, but they’re out there now. The very first time I ever wrote like that was on Matador, for my 9/11 piece. It was a big milestone and helped me figure out that the difficult stuff is worth pulling out.

How can others interested in self-publishing be successful? What advice do you have as far as putting together a book for sale via iTunes / Amazon?

If I can do it, anyone can. I was working 60+ hours a week with the mushiest of brains when I got this together.

First – give your book to friends to help edit. You can’t even imagine how many errors I had in my book, and there are still about 10 that make me crazy. My friend Deborah and Matador’s own Kate Sedgwick both really helped me comb the pages. I’ve read self-releases with errors, and it immediately makes them seem without credibility. I’m fixing mine for the physical book, and I’ll sleep better at night because of it. Put aside more time than you think for editing.

Second – find someone great to help you lay it out. Spend the money. I used booknook and can’t recommend them enough.

The thing that I think helped me most is that it was a clandestine project. There’s something so great about making this thing on your own, knowing that you have something that other people might like, but that it’s yours for the moment. Now it’s out there and it’s everyone’s. That’s fine too!