
Interview with The Thoughtful Entrepreneur Podcast
It was a pleasure to be interviewed for The Thoughtful Entrepreneur podcast.

You can listen to the episode on the UpMyInfluence website or on YouTube.
It was a pleasure to be interviewed for The Thoughtful Entrepreneur podcast.
You can listen to the episode on the UpMyInfluence website or on YouTube.
Mike Rhode and I go way back and it was a pleasure to reconnect with him on the Sketchnote Army podcast and discuss communication, creative work, and explainer videos.
What we covered in the show:
Thanks for having me on the show!
Big Enough, my forthcoming book, arrives on September 15th. It’s being published via a partnership between me and publishing industry pros. Below, I’ll explain why I made this choice, how it differs from traditional publishing, and why this option might become more popular in the future.
In 2012, I worked with Wiley, a major book publisher, to publish The Art of Explanation. I enjoyed working with Wiley and I’m proud of what we produced. Our relationship represented how publishers have worked with authors for generations.
My goal with Big Enough, though, is to self-publish a book that’s indistinguishable from one produced by a major publisher. It will appear on the same bookshelves and be of similar quality. Before getting into that, I think it’s important to understand the variety of expertise that goes into publishing nearly any book destined for bookstores.
The bottom line is this: high-quality books require significant investment and acceptance of risk. I think about it in terms of a break-even point. Will the book sell enough to pay for the cost of publishing it?
Now, let’s talk traditional publishing. In working with Wiley, I wrote the book and they handled most of the work I described above. I was not required to invest in editing, design, printing, distribution, etc. In fact, they gave me an advance payment while writing the book, which I paid back through book sales. This relationship insulated me, the author, from financial risk.
In this scenario, the publisher is betting that they can produce a book that, at least, breaks even. Because of their size and volume, they dominate the supply chains and can negotiate the best deals. They have in-house talent and decades of experience that reduce the risk. This is why “getting a book deal” is sometimes a struggle. Publishers must bet on the future work of authors.
Being an author in a traditional publishing relationship can be stressful because there is a sense of obligation. When the publisher’s money is on the line, they call the shots. Many have a structured process designed for maximum output. Because the publisher’s money goes into production, they also keep much of the income from book sales. In this scenario, authors sometimes feel a loss of control.
Now, let’s switch to Big Enough.
I love the idea of self-publishing and have spent over a decade self-publishing Common Craft videos. One of the messages of Big Enough is that technology has made it possible for anyone to be a publisher and earn a living from their intellectual property. My approach to book publishing is an expression of this focus on independence.
Self-publishing, though, has some baggage. Once it became technologically possible, authors could publish e-books with a minimum investment and without the help of experts who ensure quality, like editors and designers. Without these gatekeepers, quality sometimes suffered and self-publishing became known as inferior.
This is where things have changed. Self-publishing isn’t defined by technology, gatekeepers, or quality. There is no reason a self-published book can’t compete with a major publisher’s book. The key difference can be boiled down to a simple question: who is taking the risk?
In the case of Big Enough, it’s me. I am investing in the expertise and relationships that I believe will make the book a success. I am putting my money on the line and betting that I can make Big Enough successful enough to break even. As such, I remain in control and earn a greater percentage of the income.
My partner in this adventure is a company called Page Two, which is owned and operated by industry veterans Trena White and Jesse Finkelstein. Page Two specializes in working with non-fiction authors to self-publish high-quality books. Their team of professionals does the work of a major publisher but on a mostly fee-for-service basis. Further, they have key relationships with printers and distributors that would be difficult for me to form. Page Two is my secret weapon in making Big Enough a major publisher-style book.
One of the things I love about this relationship is that Page Two, in publishing industry terms, is a start-up. It’s refreshing to work on a book with a young company successfully being disruptive. They encourage ideas, like direct sales from my website, that major publishers might not condone. Importantly, they reflect the values I believe are important, like independence and a sense of creative control.
I consider this model of self-publishing the best option for me and the message of Big Enough. It represents a personal risk, but it’s one I’m willing to take.
Learn more about BIG ENOUGH.
The post below was sent as an issue of my newsletter, Ready for Rain.
Over the last six months, I’ve been mentally preparing to publish my second book. During that time, most of the writing was completed and the process was on track. It felt good to see it take shape. But lingering in the back of my mind was always a voice reminding me that publishing a book means more than just writing it. One of the real challenges, especially for a less established author like myself, is introducing the book to the world. For Big Enough, my next book, marketing the book is the hill I must soon climb.
For longtime authors like Stephen King or Seth Godin, book marketing is less of a challenge because they’ve spent many years establishing their brand of writing and honing their marketing. Their names are attached to a genre, style, and perspective. Their fans will reliably buy any book they publish because they know what to expect.
I don’t have that luxury. Big Enough is a book about our business and fans aren’t currently beating down my door to hear what I have to say about the subject. In that context, I’m relatively unknown. This means I have to give them a reason to be interested and that’s more difficult than it sounds.
I’ve been through this once before. When I published The Art of Explanation in 2012, it needed to be introduced to the world, too. It was my first book, so no one had any expectations regarding my writing. But I had a secret weapon. Starting in 2007, the “explainer” style videos Sachi and I produced at Common Craft became very well-known, with tens of millions of views. We were, to a small degree, internet famous. A book about explanation skills was very much on-brand and expected. It was obvious why I was the person to write it.
Given this history of video production, my name is most often connected to creativity, communication, and education. And that’s the challenge. In publishing Big Enough, I am re-introducing myself as not only a video producer but an entrepreneur who has a business-focused story to tell.
The question becomes: how? How, over the next four months, will I change that perception and position myself as the right person for writing this book?
This is, at heart, a marketing challenge and one that’s not absolutely required. I could write and publish the book without marketing it at all. In this case, the book would suddenly appear on Amazon and bookshelves without anyone expecting it. And it could work. Sometimes a book can do well by simply existing, but I am not willing to take that risk.
For Big Enough, I plan to throw myself at the marketing beast. My challenge is to learn how to market a book successfully. If I can develop a marketing strategy that fits with my style, I will have a head start for future books.
Here’s the ideal scenario… Over the next few months, I publish multiple articles, blog posts and videos that focus on the ideas in the book and point people to the book web page. I appear on podcasts and do interviews that promote it. I share links on social media that are retweeted and shared on Facebook. Popular blogs and newsletters write about the book and point people to the book’s web page and sign up to receive a free chapter and be notified when it drops. Slowly but surely, demand builds and people become interested. They tell friends. Readers have been primed for action and on the day it’s released, it makes a splash that puts it in front of even more people and momentum builds from there. That’s the ideal scenario.
For me, that day is May 5th, 2020. My focus between now and then will be on that splash, how high it can go, and how far the ripples will travel.
Making this happen, even to a small degree, is a challenge that I’m not taking lightly. I’m cautious about turning people away or making a bad impression by selling too hard. To get through it, I am summoning my gumption. It’s up to me, the author, to put myself out there and say, “Order my book. Read my articles. Post a review. Sign up for my emails. Share my posts, please?”
I don’t take naturally to self-promotion or promotion at all, really. But I also feel that my book is something people in my market will enjoy and want to know exists. It would be a mistake to put so much effort into it and just hope for the best. Instead, my plan is to promote it in a style that fits with me and I’m ready for the challenge. I’m ready to experiment and push myself. Most of all, I’m ready to learn.
This post originally appeared in my newsletter, Ready for Rain.