The Story Behind My Book, “Free Trials and Tribulations”

Why I wrote a book and how I got it published

Kyle Racki
May 23 · 9 min read

Why I decided to write a book

Writing a book has been a dream of mine since I was eleven years old.

I can actually trace the genesis of this dream to a grade 6 school project, where I had to interview an adult who did what I wanted to do when I grew up.

I interviewed Lesley Choyce, a local author here in the Maritimes, who was kind enough to come down to Joseph Giles Elementary and take questions from an eleven-year-old. Ever since, I’ve always held onto that dream of being an author and publishing a book.

As I grew up, life came at me hard and fast, throwing plenty of punches along the way (if you read my book you’ll see what I mean). But writing that book was always in the back of my mind. And along with that desire I wrestled with the author-to-be’s eternal struggle: what do I write about?

In 2016, Time published an article about the struggles that I had running a business, starting a software company, growing up as a Jehovah’s Witness, and subsequently leaving that religion. It garnered a decent amount of attention; that part of my life always seems to be the topic of interest when I’m speaking or when I’m talking to people about my entrepreneurial journey.

So, I thought it would make a good subject for a book. I decided to write somewhat of a personal memoir, especially about the last 10 to 15 years, and combine that with a business book that has the tactical and strategic lessons that I learned along the way.

Pick yourself up a copy on Amazon now, in either paperback or eBook.

Writing the book: the process from idea to publication

Thus, armed with an infallible idea, a devilishly comprehensive plan for the structure of the book, and no distractions on the horizon, I sat down and wrote the entire manuscript in a 36-hour marathon session.

Just kidding.

I struggled with getting started for months.

I encountered the same challenges I imagine innumerable aspiring authors face (and George R.R. Martin, apparently); staring at a blank Word Doc, taunted by that blinking cursor, not really sure how to move forward.

Eventually, as luck would have it, I stumbled upon a really cool company by the name of Scribe (formerly known as Book in a Box). Tucker Max, the co-founder of Scribe and a customer of ours, reached out to me one day because he wanted to talk about Proposify.

Tucker is an established author and no stranger to the New York Times bestseller list. Through that process of him reaching out I discovered what Scribe does, which is essentially helping people like me who have ideas and want to get them across and put them in a book form but aren’t experienced authors.

They guide you through the authoring process from beginning to end; from outlining the book, to writing it, designing the cover, all the way through to printing and launching it to the world. They’ll even help you with marketing.

Here’s a brief outline of the process I went through with Scribe to publish my book:

The first step is meeting your publishing manager. Mine was Ellie Cole. Scribe is a partially remote company based in Austin Texas, but with staff distributed all over the US. Ellie is based out of Hawaii. She became the person that would be with me for the entire process.

Side note: During that first call, JT McCormick, the company’s CEO, jumped on for a few minutes just to say hello and welcome. That was a really nice touch, and a great customer success tip. For founders out there, try taking a few minutes to get on a call with a new client when they come in the door. Speaking as a customer, it’s a great way to get warmed up to a new company.

Ellie ran the process from there. She introduced me to my outliner Karla, who helped me determine what the basic skeleton of the book would look like. Over several phone calls, Carla and I put together the book’s structure, organizing the key ideas and thoughts and making sure they flowed nicely. This happened over three or four two-hour phone calls. Prepare to spend a lot of time on the phone if you partake of Scribe services.

But that’s the beauty of their service: you present most of your ideas over the phone, getting them out of your head and onto the page.

I mean that quite literally. Each outline call is recorded, transcribed, and later when you’re working with your scribe — mine was named Sheila — they ask questions based on those outlined conversations. I talk and answer those questions, essentially filling the gaps in the outline, and she rewrites what I say with the proper authorial prose.

At this point you may be thinking, hang on, were these really my words? Did I actually write it?

And I would say yes, yes I did.

What ended up in the book are my words, my thoughts, and my story. That’s a big part of what Scribe does; they never insert their ideas into your book.

One of the first things the folks at Scribe establish is your individual tone; how your voice will ‘sound’ when it comes off the page. How you talk is a big part of finding that tone. Another part comes from borrowing from a decades-old writing trick; emulating the voice of writers you admire.

I pointed them to a few different authors whom I respect and the parts of their tone that I’d like to echo. For instance, I used Mike Monteiro. He’s a blogger with a witty, slightly cantankerous vibe to his writing. It’s what makes me really enjoy reading his stuff, so inserting a little bit of that humour into the book was a big focus.

It’s always hard for someone to represent your voice the way you think it is. Nailing that down came in the editing process. The text Sheila put forth from our conversations was edited several times. I took the content she wrote and edited some parts, entirely rewrote others, added new sections, and left the parts I liked.

We’d iterate that process, editing and cleaning it up and making sure everything flowed nicely. I can say with confidence the end product was my own.

From chaos to conquest: what my book is about

Free Trials and Tribulations is ultimately the story of how I started the company of my dreams with all the ups and downs along the way.

It’s a personal story. I share parts of my life most people would be embarrassed to share. But in this book, as with most things I write, I try not to pull any punches or sugarcoat things. I try to be as honest as I possibly can (without getting people in trouble or hurting anyone’s feelings).

But I tried to even go deeper, even more raw. Some of the people that I talk about I refer to by their first name only. I don’t make it obvious who it is — some of the things aren’t always flattering to them. Some of the things I say aren’t flattering for myself.

In the spirit of transparency, I’d be remiss if I didn’t mention that publishing this book got me slapped with a lawsuit. A person I wrote about in the book is suing me for defamation of character. The lawsuit is currently going on, so I’ll leave it at that for now.

But you can’t write a memoir without talking about the ugly details or the things that you’re ashamed of. Leaving that out would be disingenuous and would compromise the integrity of my story. It was important to me to remain honest, and that’s what makes it relatable.

If you’re writing anything and you’re not afraid to hit the publish button, maybe you’re not being honest enough. Being authentic isn’t easy; when I write these blog articles and I’m afraid to publish it probably means I’ve been as genuine as I can. There’s a certain amount of vulnerability attached to honesty, which is where that fear comes from.

I took that deep, honest, and personal approach ten times over with my book.

The book is split into three parts, mirroring the classic creation mythology. Part one is creation, the middle part is destruction, and the final part is rebirth. (A little tongue-in-cheek nod to my religious upbringing which I touch on quite a bit in the book.)

Growing up as a Jehovah’s Witness, I didn’t think that I would be where I am today. I thought I would always be a Jehovah’s Witness. And in fact, I didn’t even really think I would live in this world as we know it, which I know sounds a little crazy but that’s part of the belief system in which we grew up as Jehovah’s Witnesses.

At some point in my mid-20s, I went through a really powerful transformation. I woke up and realized that I didn’t agree with the religious teachings. So I left.

Leaving caused a tremendous fall out with my family. It changed who I am as a person and what I believe.

All this was going on while I was building my first business, Headspace, a web design agency. Essentially, I dig into the worst two years of my life. I lost my father, who died. I realized I was living in a cult and escaped and got shunned by my community. I got divorced. I suffered financial ruin and near bankruptcy. And so all these crazy things were happening while I was also facing a failing business.

Yet somehow I managed to climb out of that with the help of some great people in my life who I talk about in the book — one of whom is Kevin Springer, who’s my business partner. Out of chaos, we created Proposify.

Free Trials and Tribulations is the story of that journey — going from extreme hardship, extreme tribulations, to having a successful company and an amazing life now. I hope that people can find inspiration in my story, especially entrepreneurs who may be going through their own trials and tribulations, and realize that there’s light at the end of the tunnel.

The impact of writing a book

When I first started this project I had zero expectations; I didn’t think it would be an Amazon best-seller, or that I’d sell more than a handful of copies. This was a personal project—in more ways than one.

I launched the book on Jan 29th, 2019, and my friend and colleague, Jennifer Faulkner, organized a launch party for me where about 50 friends gathered to support me. I was completely blown away by the love and support shown there.

In the months since I’ve sold a few hundred copies. It’s nothing to write home about, but sales never were the point. The measure of success for me is what kind of an impact it makes upon those who read it. One reader wrote:

I’m very committed to 8 hours of sleep per night, but…

This book kept me awake until I reached the end!

Not only is Kyle Racki an engaging writer, but he writes from the heart. Kyle is someone who is not only relatable and down to earth, but he is someone who has been through the ringer and lives to tell the tale. This book honestly kept me on edge because I was living in his shoes.

In “Free Trials and Tribulations”, Kyle tells the tale of starting one of the world’s fastest growing start-ups while leaving a lifestyle and religion that is incredibly comfortable; impending bankruptcy; divorce; friendships; and fatherhood. This isn’t just a narrative on living life, but on thriving on it in today’s society. It is thought provoking, inspiring, heartwarming, and evocative. His story proves that any of us can live our dreams with the same dedication, hard work, and overwhelming grit that Kyle displays.

Well done, Kyle! A must-read for any business owner or even human being in 2019!

I’ve received dozens of comments like this one, some from people I know and others from complete strangers. Reactions like this mean a lot more to me than selling thousands of copies.

I’m incredibly proud of the finished product. Scribe did an amazing job of helping me take my ideas and vision for this book and bring it to life. I’m really excited it’s out there in the world, and I hope everyone finds it as enjoyable to read as I found it to write.


Enjoyed this article? I’d appreciate you giving it some claps. Free Trials and Tribulations is available now on Amazon, in either paperback or eBook. It would mean a lot to me if you guys check it out and let me know what you think.

Kyle Racki

Written by

CEO of Proposify, Author, Speaker, Investor

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