Today’s episode is with Kyle Racki, author of Free Trials (and Tribulations). Now, Kyle is the cofounder and CEO of Proposify, which is a SaaS company that currently serves more than 6,000 customers worldwide, and even though Kyle is a successful entrepreneur running this successful business, his book is about all the other stuff that comes with that as well.

He shares his full journey, and I mean full journey, from difficult beginnings to dealing with grief, divorce, and actually being shunned for abandoning a religion that he realized was a cult.

If you’re an entrepreneur and you know that running a company can be a lonely, stressful experience, this is the episode for you, because Kyle’s going to share how to build a business—even when life punches you in the mouth.

 

Get Kyle’s new book Free Trials (And Tribulations) on Amazon.

Find out more at KyleRacki.com.

 

Kyle Racki: I remember about 10 years ago, I was running a small agency here in town where I live in Dartmouth, and my wife and I had just separated and it was a very messy breakup. Police were called, it was just extremely chaotic. I was living in this kind of rundown apartment because I had to basically pay for the house and I needed sort of to get out of the house, so I was just down the street from the agency that I was running.

The agency wasn’t doing incredibly well, and I remember at one point, my now ex-wife had come into the office when I wasn’t there and in front of my business partner and all the staff demanded to be paid for her, I think 1% of the company. She was basically trying to get money and they had to threaten to call the police and take her out of there.

These kind of things happened many times and it sort of brought to mind that idea of right now, entrepreneurship, we’re in a time where they’re almost more rock stars than actual rock stars, right?

You’ve got Jeff Bezos walking arm and arm with Grimes, having pics taken by the paparazzi, Gary Vaynerchuck on the streets getting selfies with fans. Elon Musk is like a fashion icon. You know, actually, I got that mixed around—sorry, it was Musk who was dating Grimes and Jeff Bezos who is the style icon. Either way, right? It’s like rock stars.

When I was a teenager growing up, I wanted to be an actual rock star. Like I wanted to go on tour with my band and all that kind of thing. Now these same teenagers want to be entrepreneurs, right? They want to be the next Mark Zuckerberg or whoever.

We’re just living in a really interesting time right now, and I think what a lot of people forget is that much like an actual rock star, you have to go through years, decades even of a playing dive bars and having no money and sleeping out of your van to actually get to the point where you’re successful.

So that’s kind of what this book is really meant to encapsulate. The idea that even though it’s my story, it’s not really just me. It’s a reflection of the idea that you have to eat shit and get punched in the mouth countless times to come out on top as an entrepreneur.

It’s a combination of a personal memoir and an actual business book. There’s a story in there, it’s a little dark, a little depressing, got some humor thrown in there to lighten it up. But ultimately, it is a business book with some practical takeaways and strategies that people can implement for their own business.