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.

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.

Some of it is based on my successes, some of it is based on my failures, but they’ll get some practical takeaways.

Leaving before Doomsday

Charlie Hoehn: Your book is broken down into part one, two and three. Part one is In the Beginning, part two is Armageddon, part three is Rebirth. Is Armageddon when you left the doomsday cult?

Kyle Racki: Yeah, absolutely. As you pointed out, the structure of the book is broken into kind of like a classical mythological tale of creation, destruction, and rebirth. That’s kind of the idea behind that structure and a little nod towards the major religious element in my life that shaped who I am but also kind of destroyed me. I came out of that.

Charlie Hoehn: Wow. Of all the things that you said, I had heard before except for the doomsday cult. So let’s dig into that story. What was that like?

Kyle Racki: Yeah, I mean, that’s a loaded topic but, you know, the funny thing is that I think that people would be surprised at what I described as being a doomsday cult. You know, we tend to think of like heaven’s gate and, you know, what was the one? Drinking the KoolAid, I forget what that cult.

People tend to think about those really like fringe groups that are very small that maybe a hundred people fall for, but this particular one has 8 million followers worldwide. They’re the Jehovah’s Witnesses.

So I was actually raised as a Jehovah’s Witness from babyhood. Grew up under that belief system. Most people don’t really know a lot about the Jehovah’s Witnesses. They kind of think of them as a benign group that goes around and kind of annoys you on Saturday morning when you’re trying to watch your cartoons, eat your cereal, you get a knock on the door, somebody’s pushing a Watchtower in your face. You tell them to go away.

So I think that’s what most people think of is being a pretty harmless group, but more and more these days, there’s actually a big movement from ex-Jehovah’s Witnesses who are now starting to shine a spotlight on the religion and a lot of the scandals related to child abuse that have been coming up.

There was a lot to unpack there, but essentially, I woke up one day basically gave myself permission to read literature that was written by ex-members, which is forbidden in the religion. You’re not allowed to read anything that’s not written by Jehovah’s witnesses that talks about Jehovah’s witnesses.

For that exact reason.

“They call it the apostate material.”

Essentially, they tell you that if you read anything that an ex-member has written, it’s going to poison your mind, Satan’s going to get in there and basically control you, and there’s this fear of apostates that’s baked in. I basically gave myself permission to read it and very quickly realized that yeah, I had been raised in a cult.

Charlie Hoehn: Wow. That was earth shattering in your mind. What happened to you next?

Kyle Racki: Yeah, it was obviously a very transformative year. Everything that I thought I believed or thought was true was completely shaken up. I think it’s around the middle chapter of the book in the Armageddon section where I basically talk about kind of that time that I realized what I was in and then the steps I took to get out of it, which included sending an email to my mother thinking that I could present her evidence.

Did not go well. Ultimately led to the second breakup with my wife because we had gotten back together a few times.

Charlie Hoehn: Was she a Jehovah’s Witness as well?

Kyle Racki: She was actually, yeah. She had been raised as well as a Jehovah’s Witness and then left in her teens and then had come back as an adult. So a couple of years after, she had gotten baptized as one, that’s when she and I met.

She’s 10 years older than me. We went through this period where we’re both very gung-ho, completely brainwashed members and very into it and it was our life. Then that started to kind of fade as time went on for various reasons, so when I actually presented it to her, she rejected it at first because of the mind control but ultimately she ended up leaving as well.

We’re not together anymore, but she’s still out.

The Story behind the Star

Charlie Hoehn: Man, Kyle, I’ve got to say, I so appreciate you including that story in your book. What do you think young entrepreneurs, people who are just starting out in their journey, are missing by not getting this more human side, the full story of entrepreneurship?

Kyle Racki: I think we’re hearing a lot these days about what social media is doing to our brains and how when you’re looking at Instagram and Facebook and seeing people’s highlight reels, it makes people depressed because they feel like, “Wow, my life doesn’t match up to my friend’s lives.”

I think that to a large degree, we get that both on social media and just in general. We only really hear about the successful entrepreneurs. We don’t hear a lot about the failed ones, and those are much more plentiful than the successful ones. Specifically when you read TechCrunch and hear about unicorns and the Ubers and the Airbnbs. People tend to not look at those as being outliers, which they are. They kind of look at them as, “Wow, why haven’t I done that?” or “Why isn’t my businesses as successful as them?”

When you dig underneath the hood, you realize that for every Airbnb or Uber, there’s thousands of businesses that have failed along the way or some of them actually are doing well. They just kind of fly under the radar but really, the stories are very disparate. I’ve also found through research that depression is much higher among entrepreneurs than the general population. There’s a higher rate of depression and suicide and drug and alcohol addiction and I think probably a lot of that is because building a business is really hard and everybody has challenges in their lives.

Everybody has to deal with illness or deaths in the family or you know, issues with their relationships. Everybody deals with that, but then throw on top of that the burden of trying to provide for your employees, trying to make payroll, trying to make your customers happy, try not to lose your house in the midst of doing that, and it’s a recipe for disaster.

I think that more and more people are coming out and talking about their failures or their personal challenges or tragedies, it kind of makes you feel like you’re not alone, this is common, you’re not the weirdo.

I found that especially running an agency. I run a Software as a Service business now, but back when I was running an agency, which was my first business and ultimately a massive failure, in the local community of other agencies who you’re mostly competing against, it was sort of this thing…you go to a conference or an event where maybe somebody who runs a competing agency is at and you say to them, “Hey, how’s business?”

“Oh, it’s doing great, amazing work, we’re just slammed with work. We have no time for anymore. We’re just killing it,” and it sort of this puffing out your feathers because you don’t want that competing agency to think that, “Oh geez, I don’t know how am I going to make payroll. We had a client who is not paying their bill and another one the project is way over budget and we are losing money on it.”

Nobody ever tells that because they don’t want their competitors having any view that they are weak or they are failing.

Charlie Hoehn: I have seen it in the author world, right? Speaking with authors, I compare myself to a handful of authors who I know who have sold millions of copies of their books. And if I only look at them, I view myself as a not very good author. But they are in the 0.001% like literally in authors, they’re anomalies. I think the same thing goes with business.

Kyle Racki: Yeah, I talk about that in the book too, a lot—about imposter syndrome. It comes up again and again.

I actually started community college at a pretty young age because I graduated, just based on my age and when I was born, when I was 17. I’d started college and was really intimidated by the idea that I was there with older people in their 20s and 30s and 40s. So I felt like, “Wow, these are the people I am competing with for graphic design positions out there in the city?” Like, there is no way somebody is going to hire a kid like me to design their billboard or whatever.

Then of course eventually I got a job at 18 or 19, and I was like, “I can’t believe what are they doing? Why are they paying me for this to sit around and design things?” Then later becoming a freelancer and then becoming an agency owner and then a SaaS founder.

Basically, at every step of my journey I was like, “There is no way somebody is going to pay me to do this.” A lot of it comes down to imposter syndrome, even just writing this book. I’m like, “Wow, who is going to pay to read my words?” You know what I mean? It just is constant, and I don’t think it ever ends.

New Beginnings

Charlie Hoehn: I want to talk about part three in Rebirth and the tides changing for you. Tell me a story from this section of the book where you started to come into a new life.

Kyle Racki: Yeah there’s a couple pivotal moments. At the time, I didn’t realize how significant they were, but in hindsight of course you realize how your life may have changed if you didn’t take that action.

One of them was December of 2013, we were in the midst of trying to sell off our agency business, which was failing and we were struggling to keep running. We had these buyers who were interested, but they were delaying the deal. Our lawyers were delaying it, and really, we should have just laid everybody off, filed for bankruptcy, screwed over our clients and our landlord and our debtors and all that kind of stuff.

It would have probably been the most practical approach, but we were trying to keep this thing floating just enough.

“Just long enough to be able to sell it and get it into somebody else’s hands.”

Proposify as a company, which is my software business, was really at the early startup stage. I was working with a developer on getting it out there but we didn’t have customers at the time, and amongst all of that I had just broken my toe because I kicked a dresser in anger.

I was still dealing with a lot of the post cult trauma syndrome, which is (believe it or not) a real thing.

So I was really in a bad place, and it was winter too so it was always dark and depressing. I was feeling pretty borderline suicidal. Then I just decided, “I need to get out there in the community or something and like go to an event and talk to other entrepreneurs.”

I noticed that this startup house, Volta, was putting on a pitch competition where you stand up for five minutes and pitch your startup and then you have judges who vote on it. So I ended up signing up for it and going to it and pitching, and what was really cool was I won the competition. So the judges voted for me to win it.

But then even more pivotal was the idea that there was investors in the audience, one of whom came up to me afterwards and basically said, “Hey, I knew we chatted a year ago and we didn’t think you guys are ready. We’re in now. We want you to pitch the board and get in. We’ll fund your venture.”

That was a game changer for us. So what ended up happening was in one month we literally sold our agency and raised a seed around for Proposify, which completely changed everything for us. If I hadn’t gotten out there to that event, maybe that wouldn’t have happened.

Life Today

Charlie Hoehn: Awesome and now you are the CEO and cofounder of Proposify, of course, and what is life like for you today? Describe your typical week at Proposify.

Kyle Racki: We have a great team here. We’re just up about 65-person mark at the company. We have a very positive culture here at Proposify. A lot of new people because we have grown a lot in the last year.

A typical week is actually busy, but it is a good kind of busy. I am trying to make health more of a priority. So I’ll usually go to the gym before I come in, maybe come in around 10 or 11. I usually have a lot of meetings and calls and that kind of thing for the afternoon but really have a pretty good work-life balance.

I got remarried this past September to Christina. She had also come off a divorce in the last couple of years, so yeah, we found a lot in common there. I also have two sons. So I have Micah and Ty from my previous marriage. We are building a house right now, and things are great.

I am part of a coaching group with Dan Martell. I don’t know if maybe listeners have heard?

Charlie Hoehn: He is the founder of Clarity FM, which I am sure many listeners have used to book calls with experts on particular topics, specifically entrepreneurs.

Kyle Racki: He’s got his own really interesting story. He actually writes the forward for the book. So I am part of his coaching group, this thing called JFDI. There is about 10 of us in the group and we go to different cities. We were just in Boston last week, and the reason I brought that up is that he did something interesting with us to help us get to know each other better. We drew a timeline of basically our birth to now, and then we had to draw all the highest and the lowest points and talk about them to the group for 10 minutes.

And the thing that was fascinating to me was just how many people who are all successful entrepreneurs with SaaS businesses in the $5 to $10 million a year range and how almost every single one of them has had crazy horrible things happen to them in their life. From addiction to trauma to suicides of close people in their lives. Maybe that just speaks to the general population, but I do think that entrepreneurs experience that at a higher rate than probably most.

Reaching Out

Charlie Hoehn: Did you have one main goal in mind when you were making this book?

Kyle Racki: I have wanted to write a book for a very long time, basically since I was a kid. I actually interviewed an author when I was I think 11 years old in grade six when they said, “What do you want to do one day?” and then you have to interview somebody who does that.

There was a local author named Leslie Choice who came in and took questions from an 11 year old. So actually it was a lifelong goal, kind of a personal milestone.

I also really enjoy creating things. I have been blogging and doing podcasts and stuff for the last few years. I like making music, and my dream is to actually one day make a movie. That is a big passion of mine.

So I just enjoy creating content and I enjoy sharing the lessons, the mistakes and the wins and so this was just another format for that was to tell the personal story but, again, talk about the actual takeaways, the business lessons.

So I think for people who read the latter part of the book, the part three of Rebirth is that is where you get into more like how do you generate demand through content, how do you grow through key performance indicators? You get into more the actual meat, the really practical stuff around building a business. So I wanted to share all of that.

Charlie Hoehn: Awesome. If you were going to make a movie this year, what would that movie be about?

Kyle Racki: Oh it would probably be some variation of this. Maybe the protagonist isn’t Kyle Racki, but there’d probably be a lot of similar things happening. I think you could probably point to any ad agency in the city you live in and I bet there is a TV show in it, you know? Because there’s just ridiculous characters who work at these places—and startups too, for sure.

Connect with Kyle Racki

Charlie Hoehn: True. This has been awesome. My final two questions for you are what’s the best place for our listeners to follow you or potentially connect with you?

Kyle Racki: So if they want to, from a personal standpoint, check out my website, That’s basically where the blog and link to sign up to the book. You’ll get links there as soon as it launches.

If people want to check out my business it is and basically we’re a SaaS product that helps sales teams write proposals faster and get faster sign off.

Charlie Hoehn: I’ll attest to Proposify being an awesome product. So it is definitely worth checking out if you write proposals. The final question is, give our listeners a challenge. What is the one thing that they can do from your book this week that will have a positive impact?

Kyle Racki: I think so often people underestimate themselves. So I talked about imposter syndrome. One thing I had once said to an entrepreneur who was talking to me about what he had planned for his business, I kind of felt like he was aiming really low. So I actually wrote a post about it called, Stop Aiming for the Trees, and that’s what I think a lot of us do. We go, “Well we can never aim for the moon or the stars.” Some people call it sandbagging, where you set your goal so low that it is just easy to achieve. You don’t really have to stretch yourself.

So I think as a challenge, what people could do is if you don’t have any goals for the next five years in terms of what do you want your ideal life to look like—I had written that down a number of years ago and then pulled it out. It was an Evernote file. I pulled it out recently and I was like, “Holy crap!” I actually knocked most of these things off.

It’s not like I went back and referred to it every day. It just sort of happened.

I think when you write down what your ideal life looks like, you’d be amazed at how that sticks in the back of your head and how you put in the work and you do the things that will get you there.

I’d actually challenge people to aim higher than they probably already are.