How We Wrote a Bestseller in 90 Days – The Inside Story of “Insuring Tomorrow”

People think I’m insane when I tell them that we wrote Insuring Tomorrow: Engaging Millennials in the Insurance Industry in 90 days. They hold the book up and say “How? It’s excellent. I love it! How on Earth did you write this in 90 days? 90 days?!?”.

I’d like to pretend we’re geniuses, but we’re not. The truth is we wrote it in 90 days, and we wrote it in five years. It took us five years of being obsessed with the insurance ecosystem and the demographic and talent crisis it is facing. Five years spent collecting and reading everything we could get our hands on about Millennials as employees and about Millennials in insurance. Five years of attending multiple insurance conferences and participating in spirited hours-long debates about the topic. Five years of chatting with every Millennial insurance professional we could find and asking them about their experience.

I’m not going to pretend we could’ve pulled it off without those five years of research, and this article isn’t a crazy how to write a book in 90 days guide, it’s just the inside story of how we wrote ours.

Early this year, my girlfriend came home, and, in a very matter of fact voice, she informed me “You have to write the book, it’s time. If you wait much longer, the time will pass and you’ll miss your chance.” I called Carly and simply said “It’s time to write the book.” I didn’t have to explain which book, she knew. We had been preparing for half a decade. We knew exactly what we had to do; we just had no idea how to do it.

Right away, I set a deadline of June 1st. I truly had no clue how we’d hit it or even if it was possible to hit it, but I knew we had to do it quickly. Without a deadline, the book would never happen. I created a shared document on Google Docs and… nothing happened… it sat completely blank for a few weeks. Even a deadline wasn’t going to push us forward until we had a plan.


We are passionate travelers, and we had a trip to Lana’i planned with my girlfriend’s family. We expected this trip to be mostly relaxing hanging out in the beach house and staring at the water. I told her I’d start really working on the book during that time. The trip came and went and, when we returned, all I had done was a table of contents. I showed it to my girlfriend who told me it wasn’t good. “Do it again. You can do better”.

A couple of weeks after that I finally sat down and wrote a little bit better table of contents, and Carly and I agreed to a standing meeting every Saturday until release date. At this point, it was early April, and we only had 90 days to get it done by deadline, that’s when we jumped into action. We assigned each chapter to one of us to be primarily responsible and set deadlines on when drafts of each chapter would be ready. We used what I like to think of as “Agile Book Writing”. Every morning we’d text each other asking “What’s your productivity plan for today? What are you stuck on?”, and we’d keep each other accountable at the end of the day.

Some chapters came very easily; others were very hard. Ultimately, we ended up cutting some chapters out because even though we thought the ideas in them were important, we couldn’t find enough resources to back up our thinking. The book had to be more than just our opinions, it had to help anybody who read it understand the issues facing the industry, not just people who already trusted us. In fact, the most important thing was to make sure that when somebody who doesn’t know us from Adam picks up the book, they come across with a full understanding of our thinking and have a roadmap of further readings to actually put some of our recommendations into practice.

We engaged in spirited debates about how much of other people’s ideas to include and on how to support more controversial ideas like sabbaticals and student loan reimbursement. We fought over the placement of commas (or more accurately the fact that I simply don’t use them or put them in random parts of a sentence). We reached out to several industry leaders asking for permission to include something they had said or written in the book.

By April, a rough draft of the book was starting to take shape, but it was nowhere near completed. We had a major difference of opinion, very common of our diametrically opposite personalities. I wanted to start marketing the book right away. Carly was adamant on waiting until we had a completed rough draft. I had a pretty good idea that we wouldn’t have a rough draft until 2-3 weeks before publication, and I wanted more time to build buzz!

We didn’t yet have a cover, a title, or a proper rough draft, but time was running short, and the CPCU Society Leadership summit was fast approaching. So, I quietly ordered little business cards that simply said “Engaging Millennials in Insurance The Book to Solve The Talent Crisis. By . Pre-order at http://MillennialsAt.Work “. The cards were in the theme of an old cassette tape which I figured would be a good conversation starter.

I registered the very unfinished book for pre-sale on Amazon and realized for the first time that Amazon doesn’t allow you to change a release date once you’ve set it up for preorder. We were now married to the early June release. They also don’t let you create a book for pre-order unless you upload it to the system. I didn’t have a finished book, so I uploaded what I had. A potentially career-destroying, not nearly cleaned up version of only about 100 pages, full of grammatical errors and lacking in continuity or grace. I lovingly called the file “The Headfake” and would refer to it as The Timebomb from then on. The deed was done. Rain, thunder or snow, Amazon was going to “ship” any pre-orders on release date and make us look awful, unless we upload a cleaned up version in time, three days before release.

We went back and forth on what to call the darn thing. I offered all sorts of awful titles: iSurance, GenInsurance, TalentBomb, and I don’t even remember some of the others. Carly, Nick and myself all came up with their own suggestions. Finally, in a moment of absolute brilliance Carly texted us “How about Insuring Tomorrow”? We all knew right away she had struck gold. The name was decided.


Less than a week before Leadership Summit, I went on Fiverr and hired two different designers to work on the cover. We really had no idea what it should look like. I paid one of them $50 and the other one $150 and gave them each 3 days to come up with something. They came up with several designs but nothing we loved. Then Nick suggested “You’re talking basically about remodeling the industry. How about something construction related?” I didn’t love it, but we still gave the idea to the designers. They came up with about 10 different covers ideas, and there were four we kind of liked.

I wanted to test the four covers in a massive poll of our entire networks to find the best one, but Carly was against the idea. “We are not going to be one of those authors who outsources the design of their book.” She finally relented and agreed to let me privately poll a few of my closest friends. “Maybe 5-10 people at most”. So of course off I went and created a SurveyMonkey and privately message 180 of my closest friends! (Before reading this post Carly had no clue there were that many people involved. There’s a chance I’ll get yelled at once she reads this.)



Carly and I both kind of liked a newspaper themed version of the cover, but the result wasn’t even close. The crowd loved the construction-themed cover Nick had inspired so we went with that one. The book now had a title and a cover. But the rough draft was still only at about 60%.

We kept working on the rough draft, and on April 20th, we headed to Baltimore, MD for the CPCU Leadership Summit. I flew from Atlanta, while Carly and her husband drove from Pennsylvania. The morning the conference was opening I posted an article on InsNerds publicly announcing the release of the book and encouraging people to preorder it. Carly was driving and literally had no idea what was going on.

I ran around the conference like a madman handing out the little cards. It quickly became clear that there was a lot of interest on the topic, and preorders starting rolling in. The pressure was on! If we failed to produce a good final version, there would be no way to avoid the embarrassment now. It would be a very public defeat.

By mid-morning of the first day, I finally ran into Carly. I considered whether I needed to run for my life, but she appeared friendly. I asked her if she was upset about me posting the article announcing the book without giving her a heads up. She was annoyed but understanding and just asked me to borrow my laptop to correct my grammar in the post. (Carly’s Note: I would have waited to announce until 2020, if I could have, but I’m pragmatic enough to know that somewhere in between Tony’s plans and mine is usually the best option.)

We came back from Maryland re-energized and jumped head first into finishing the book. We made tons of progress, but the more we dug, the more we found new primary sources we wanted to include. Maybe we should have a chapter on gamification! How on Earth do we not have a chapter on internships!? That’s important! You do it. No, you do it.


We had secured an editor for the book, and we had promised we’d have a finished version of the draft to her three weeks before release date. But, as the date drew nearer, it became clear there was no way we were going to hit that deadline. We begged and pleaded with the editor to engage with us on an agile editing process. She would edit while we were still actively writing and creating new content… She wasn’t happy about it, but thankfully she reluctantly agreed.

The last three weeks were a blur of early morning “What’s your productivity plan?” texts and late nights. Red Bull became a staple of my breakfast, lunch and dinner menu in order to survive on four to five hours of sleep. I also realized how stupid I had been when setting the release date. The great majority of my book of business at my day job unexplainable renews on 6/11, meaning that my busiest months are May and early June, the exact same months when the book had to get finished in! Whatever happens, you can bet our next book will have a December release date 😛

Photo “The evolution of Can” by Damien du Toit. Shared on Flickr under creative Common Attribution 2.0


Tony actually drinks the sugarfree version, but you get the general idea.

We met with the editor at the end of May, and she told us she thought the book was “pretty good. At least you won’t embarrass yourselves.” We kept working on it and finished the final version just seven hours prior to Amazon’s deadline. I submitted the manuscript, cover, and book description and let out a big sigh. Within 24 hours, the powers that be had approved it and all that was left was waiting for release.


We had learned that quickly getting five to ten Amazon reviews in the first few days after release was absolutely necessary, otherwise your book will die on the shelf, so to speak. We sent out a few dozen copies to some of our closest mentors and advisers asking for feedback and an Amazon review pretty pretty please. The review copies were sent via email on Friday; the book would officially release to the public on Monday. This was going to be an interesting weekend. I went to bed Friday night wondering when I would get the first review and crossing my fingers that we hadn’t completely missed the mark.

I woke up Saturday morning, and I had an email from one of our trusted advisers. He had read the book cover-to-cover during a flight to London and had written a thoughtful, several paragraph long email with this thoughts. I read the email with my heart pounding. He’s a big-wig in the industry, the CEO of a reinsurance carrier and a demanding leader who expects a lot. I expected some tough criticism and prepared to be thick-skinned and learn from my mistakes. I read paragraph after glowing paragraph about how much he had loved the book. I figured the constructive criticism was at the end, but it never came. To my surprise, he had loved the book overall, he said it was “ready to ship as is.” That’s the very moment I knew we had done it. We had successfully written and published a book that would change the insurance industry. From that day on, we weren’t just Tony and Carly the crazy kids that run that one insurance blog. We are authors. We are thought leaders. We are changing insurance for the better!

Since then, the book has sold over 500 copies, which in our very tiny niche of insurance books, makes it an official best seller and has quickly exceeded our expectations. VERY few business books sell more than 5,000 copies, 500 copies is a HUGELY successful start. As of today it has collected 30 uniformly positive reviews on Amazon and has a 4.9 stars average. Only a single review is 4 stars, and it’s still pretty positive. We have received two bulk orders from insurance companies and industry organizations wanting groups of their leaders to read it and a major recruiting firm gave out over 100 copies to the attendants at the Super Regional conference. We’re also getting invitations for awesome speaking engagements: Carly will be speaking at the 2018 Women in Insurance conference, and I’ll be giving my session as the opening session keynote at PLRB New Orleans later this year. And we are just getting started!

One of the coolest things is that since we decided that it made more sense for InsNerds to become a publisher, rather than go through a traditional one, we own the entire rights to the book and can do really cool stuff with it like customize copies for specific purposes. We’ll have an article about that in a few weeks.

You can buy copies of Insuring Tomorrow: Engaging Millennials in the Insurance Industry here.

About Antonio Canas

Tony started in insurance in 2009 and immediately became a designation addict and shortly thereafter a proud insurance nerd. He has worked in claims, underwriting, finance and sales management, at 4 carriers, 6 cities and 5 states. Tony is passionate about insurance, technology and especially helping the insurance industry figure out how to retain and engage the younger generation of insurance professionals. Tony is a co-founder of and a passionate speaker.

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