459: Unexpected Twists On My Book Publishing Journey – A Behind The Scenes Look | Family First Friday

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My book publishing journey with The Family First Entrepreneur took three years, resulted in a six-figure advance from HarperCollins (a Big Five publisher), and required a 49-page proposal, a literary agent, and roughly nine months of writing before the marketing work even started. This is a candid Family First Friday episode of the My Wife Quit Her Job podcast, recorded four days before the book officially released, walking through every step of the process and the four-prong launch strategy I used to chase a national bestseller list.

None of the six-figure advance is going in my pocket. Every penny went back into marketing the book. I wrote it for four reasons that have nothing to do with money, and I picked traditional publishing over self publishing for one reason that is almost entirely ego.

Below is the full behind-the-scenes breakdown: why I wrote it, why I went traditional, how the proposal and agent process worked, how the actual writing got done, and the exact four-prong strategy I used to move copies during launch week.

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Key takeaways

• Writing a book was never going to be profitable on its own. Even with a six-figure advance, every dollar went back into marketing.
• My four reasons for writing the book: a lifelong bucket-list goal, a moment I could share with my kids in a bookstore, credibility with my mom (who never understood my online businesses), and lead generation for the rest of the business.
• I chose traditional publishing over self publishing purely for the Barnes & Noble shelf, the bestseller-list eligibility, and the pride of a Big Five imprint.
• Hiring Jeff Goins (bestselling author, founder of Fresh Complaint) was step one. The proposal alone took a year to build.
• The 49-page book proposal covered author bio, marketing, target market, comparable titles, annotated outline, and a sample chapter.
• The advance was six figures, royalties are ~15% per book, and at $30 cover price the book would need to sell ~22,000 copies to earn out.
• Only 48% of US adults finished one book in the past year. Books are a genuinely hard sell in the TikTok era.
• To hit a national bestseller list you need to sell 5,000 to 6,000 US hardcover copies in one week. Ebooks and audiobooks do not count.
• My four-prong bestseller strategy: $690 in expiring bonuses, an aggressive podcast tour, favor calls to friends’ email lists, and bulk sales to past sponsors who wanted to gift books to their audience.

Why I wrote The Family First Entrepreneur

I wrote The Family First Entrepreneur for four reasons, and none of them was money. Writing a book was never going to be a lucrative career move, and even the six-figure advance went entirely back into launch marketing.

Reason one was pure bucket list. I have always wanted to walk my kids through a bookstore and show them a book with my name on it, which is something we planned to do on release day at our local Barnes & Noble.

Reason two was my mom, who never understood any of my online businesses. Selling handkerchiefs, running a blog, hosting a podcast: all of it confused her.

When I told her I was publishing a book she finally got excited, because a physical book on a physical shelf was something she could relate to.

Reason three was that a lot of the business books I was reading did not apply to me. I did not want to work 80 hours a week or chase a public exit at the cost of my family, and there was no book on the shelf saying it was okay to build something smaller.

Reason four was the boring one: a book is great lead gen for the rest of the business, and it tends to unlock speaking engagements, media coverage, and additional credibility.

Why I chose traditional publishing over self publishing

I chose traditional publishing over self publishing because self publishing does not get you into physical bookstores at scale and does not put you in credible contention for a national bestseller list. Self publishing usually pays better per copy (roughly 70% margin versus ~15% royalties), but money was never the point. Ego and legacy were.

I wanted a Big Five imprint on the spine and a shot at the New York Times, Wall Street Journal, or USA Today list. The process reminded me of applying to Stanford. I picked the goal, reverse-engineered exactly what it would take, and executed.

If your goal is maximum profit per copy or getting to market fast, self publishing is the better choice. If your goal is bookstore distribution and bestseller eligibility, traditional is still the only realistic path.

The first hire: bringing in Jeff Goins

The single most important decision I made was hiring Jeff Goins early, because I knew nothing about publishing and Jeff had already written multiple bestsellers. Jeff is a national bestselling author (The Art of Work, Real Artists Don’t Starve) and the founder of Fresh Complaint, which helps authors plan, write, and publish books.

We met in 2015 at FinCon, where he was a keynote. I bought his book, he signed it, it went on my shelf, and I had no expectation of ever working with him.

Years later he was one of the first calls I made when the book idea got serious. I think of moments like that as lottery tickets. The more people you meet and the more work you do, the more tickets you accumulate, and eventually one of them cashes in.

Step 1: Writing the 49-page book proposal

The book proposal is the document literary agents use to sell your book to publishers before you have written any of the actual manuscript, and it took me a full year working with Jeff to complete. Mine was 49 pages long.

The standard sections in a professional proposal:

• Highlights about the author (credentials, platform, media)
• About the collaborator (if you are working with a ghostwriter)
• Marketing and publicity plan for the book
• Target market and audience
• Comparable titles (books like yours, and how yours is different)
• Annotated outline (every chapter, one paragraph each)
• A full sample chapter

Nailing the angle inside the proposal took the most work. I already had 800+ blog posts, 400+ course videos, and roughly 350 podcast episodes, spanning e-commerce, business, philosophy, parenting, and investing. The problem was finding the through line.

After many hours of conversation with Jeff, it landed. Most business books are written by single guys with no dependents whose default mode is grow, grow, grow, and almost none address the entrepreneur who wants a great business without becoming a stranger to their family.

That gap became the book.

Step 2: Hiring an agent and running the auction

Once the proposal was ready, I hired a literary agent to shop it to editors at the Big Five publishers because agents already have those relationships and unagented authors typically make substantially less money. Agents take 15% of your advance and royalties.

My agent pitched the proposal to his contacts. I ran Zoom meetings with several interested publishers to test editor fit, and then we set a bid date. On that date, publishers submitted their offers.

I picked HarperCollins largely because of my editor Hollis, who had previously worked with Gary Vee and other business authors. Editor fit matters a lot more than the top-line dollar amount, because that editor is the person you will actually work with for the next two years.

The actual economics of a six-figure advance

A six-figure advance sounds great until you do the math on when it earns out. I got roughly 15% royalties per copy sold, so on a $30 hardcover that is about $4.50 per book.

At a $100,000 advance (round numbers), the book would need to sell about 22,000 copies before I would see any additional royalty check. That is genuinely hard to hit, and most business books never do.

I was not writing this book to make money on royalties, so this did not bother me. But it is important context for anyone considering the traditional path expecting a big payday from the book itself.

Step 3: Writing the manuscript in nine months

With Jeff and his team, I drafted the guts of the manuscript in about nine months by combining my existing blog posts and course material with new audio I recorded to fill the gaps. Most of my writing these days is done by talking into Google Docs and editing the transcript, because I can speak faster than I can type.

HarperCollins was easy to work with on edits. The only substantive change they asked for was removing a section where I made some jokes about China. I agreed to cut it, mostly because I go to the Canton Fair every other year and would rather not get blacklisted or stranded.

Writing was the most tedious phase but also the most straightforward. Once the structure was set, it was mostly execution.

Why selling a book is harder than selling a $2,000 course

A $30 book is harder to sell than a $2,000 online course or a $1,000 conference ticket, because reading a book takes hours and the modern attention economy has trained people out of that habit. In 2022, only 288 million printed books were sold in the US total, while YouTube sees roughly 5 billion video views every day.

The average TikTok user spends 1.5 hours per day on the platform. Compare that to the fact that only 48% of US adults finished a single book in the last year, and you can see the demand curve is not tilted in a book’s favor.

That does not mean books are dead. It does mean you need a launch plan that respects how differently people consume information now.

Why book bestseller lists have strange rules

To hit a national bestseller list you need to sell 5,000 to 6,000 US hardcover copies in a single week, and every copy has to be attributable to a unique buyer or IP address so you cannot bulk-buy your way onto the list. Ebooks and audiobooks do not count, which is bizarre in a world where a huge share of readers only consume books digitally.

My wife only reads ebooks. Friends of mine only listen to audiobooks. None of that helps a bestseller campaign, which is one reason the launch strategy has to be so distributed.

You also cannot rely on Amazon’s own weekly numbers, because they report their sales to the lists on their own schedule, which does not always line up with launch week.

The bestseller campaign advice that changed my launch

My book launch coach told me to stop trying to sell the book and start selling the bonuses, throwing the book in for free effectively. I took that advice to heart from day one of the launch.

I stacked $690 worth of high-value bonuses on top of the book:

• A three-day workshop on how to start a print-on-demand business
• A two-day course on how to make money with blogging, YouTube, and podcasting
• A six-week Family First business challenge starting in June, where I would work with buyers inside a private Facebook group to help them figure out their next side hustle

When I first launched the bonuses on their own, I sold maybe 100 books. It was going to be a real uphill fight to move thousands.

My four-prong bestseller launch strategy

To have any shot at the bestseller list, I ran a four-prong launch strategy in parallel, because no single channel can move 5,000+ hardcover copies in a week on its own. Every prong targeted a different pool of buyers.

Prong 1: The bonus stack with weekly urgency

I offered the $690 bonus stack for buying the book, then launched an expiring bonus every single week in April to keep urgency high. That urgency loop worked well, and April ended up being my strongest sales month. People need a specific reason to act now.

Prong 2: An aggressive podcast tour

I called in favors with friends who host popular podcasts and ran an intense tour that peaked at four podcast recordings in a single day. I do not recommend that pace. It is exhausting and the ROI is not obvious in real time, but the compound effect is a launch-week buzz and a wave of new audiences hearing about the book at once.

Prong 3: Email list swaps with friends

I worked with a bunch of close friends in the space to have them blast their email lists announcing the book. Email is still the highest-converting channel by a wide margin for book sales.

Prong 4: Bulk sales to past sponsors

The prong most people miss: I went back to every company that had ever sponsored me and offered to trade content (sponsored ad reads, videos, blog posts) for bulk book purchases. The sponsor would give the books away to their own audience, then send me a spreadsheet of physical shipping addresses so the books could be sent to unique buyers, which is what counts toward the bestseller list.

Why I did not spend my way onto the New York Times list

There are ways to buy your way onto a bestseller list. An acquaintance of mine spent roughly $1 million on ads to move enough books to hit the New York Times list. I was never going to spend that kind of money.

I am famously frugal. There was no scenario in which I would spend more on marketing the book than the advance was worth.

I got close to my target through the four-prong strategy alone, which was the whole point of picking a target realistic for our size instead of chasing the biggest possible number.

Frequently asked questions

Is traditional publishing worth it if you already have an audience?

Traditional publishing is worth it if you want physical bookstore distribution, bestseller-list eligibility, or the credibility of a Big Five imprint. If your goal is maximum profit per copy or a fast release, self publishing pays more and gets you to market in weeks instead of years.

How much does a book advance actually pay?

Business-book advances range widely, from about $10,000 for a first-time author with a smaller platform to mid six figures for authors with major reach. Advances are paid in installments (typically on signing, delivery of the manuscript, publication, and paperback release), and you have to sell enough copies to earn out the advance before you see any royalty checks.

Do you need a literary agent to sell a book?

You do not technically need an agent, but unagented authors typically get smaller advances and less favorable contract terms, which usually costs more than the 15% commission an agent takes. Agents also protect you from clauses that could hand the publisher rights over your derivative products like courses or membership sites.

How many copies do you have to sell to hit a bestseller list?

You generally need to sell 5,000 to 6,000 US hardcover copies in a single week to hit the New York Times, Wall Street Journal, or USA Today bestseller list, and every sale has to be attributed to a unique buyer or IP address. Ebooks and audiobooks do not count toward those lists.

How long does the whole book publishing process take?

Plan on at least two to three years from idea to release day. My proposal took a year, the writing took about nine months, and the publisher’s production pipeline added another year on top of that before the book hit shelves.

What is the best strategy to sell books on launch week?

Sell bonuses instead of the book itself, then throw in the book. Stack high-value bonuses that your audience would actually pay for on their own, make ordering the hardcover the only way to unlock them, and drive urgency with expiring components. Combine that with a podcast tour, email swaps with friends’ lists, and bulk sales to past sponsors who want to gift books to their audience.

How much of the advance goes to marketing the book?

For most first-time business-book authors, essentially all of the advance goes back into launch marketing (podcast tour production, bonus development, promotional copies, launch coach fees, and ads). Very few first books earn out enough in royalties for the author to keep the advance itself as profit.

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