Who I Am


Not a born hustler.

Kyle Racki is the co-founder and CEO of Proposify, a SaaS company based out of Canada that helps more than 8,000 sales teams eliminate the frustration caused by the proposal-process.

He started his first business, a web design company, at age twenty-four and sold it after five years. Kyle has blogged extensively about his journey through the ups and downs of entrepreneurship and was the subject of a 2016 article in TIME Magazine.

In 2019 He published his first book, Free Trials & Tribulations: How To Build A Business While Getting Punched In The Mouth, which was featured as an Amazon Best Seller.

Here is what readers of his book are saying:

“This is exactly what a startup founder needs to feel like there is some level of support and a comforting "pat on the back" during this journey.

Building a company is one of the hardest things that you will ever do, and you will hear people tell you that you're doing it wrong or that it's too risky for you to move forward with. It can be debilitating sometimes, with the amount of struggles and the ups and downs.

Kyle's story shows just how important these struggles are, that "diamonds come from pressure", and that, sometimes, the most beautiful things can come out of the darkest places.

Kyle's struggles with leaving his religion, with the tumultuous balance between his agency and his crumbling family life, and all the other rollercoasters that he has been on through his journey - it's exactly what I need to read about right now.

To see Kyle doing great now - with a company of over 80 employees, as a trusted startup advisor and community leader, and a loving father and husband. It's really amazing to see how far things have changed for him, and this book is that whisper in the darkness that tells you to keep going.”

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!

An amazing and surprisingly candid insight into the details leading to this remarkable success story. It is written in a very relatable way which makes the reader feel as if they are being told a story over coffee rather than a do's and don'ts narrative so common in these types of books. I read most of this book on a plane trip and was actually saddened to reach my destination as I really didn't want to stop. I did walk off the plane however with a sense of motivation and inspiration despite the rather negative and dreadful epoch we live in.