How I escaped a cult and built a multi-million dollar SaaS business.


This is a talk I gave in 2015 that reflects my startup journey.

The following is a revised version of what appeared on the Groove blog and a post I wrote on the Proposify blog. You can also read about my story on TIME

I was raised in a cult.

As the son of devout Jehovah’s Witnesses, I spent much of my childhood and early adulthood studying Watchtower literature, going to meeting (church) and service (door-to-door preaching). 

In 2012 my father died at 56 years old, and a month later my second son was born.

Thinking deeply about life, I finally gave myself permission to research my religion, reading websites like JWfacts. In so doing, I discovered that much of what I had been taught was absolute truth was a lie.

When I told my mother and sister what I had learned, they said they'd never speak to me again, as is the standard practice when a baptized member leaves the religion. Everyone I knew in the religion also shunned me. 

My last photo with my family, a day before my father died.

My last photo with my family, a day before my father died.

My wife and I separated for the second (but not final time). While this was going on I was deeply in debt, both personally and with my agency business. I considered ending it all but for the sake of my children.

Fast forward a few years, and today I'm the CEO of Proposify, a profitable and rapidly growing SaaS business. I'm personally healthier and happier in every way.

Here's how I got here:

Why I became an entrepreneur

I (on the right) grew up 20 minutes outside of Halifax, Nova Scotia, Canada.

I (on the right) grew up 20 minutes outside of Halifax, Nova Scotia, Canada.

Because of my religious upbringing, I was only 20 when I got married. I had a stepdaughter, and all I wanted to do was get a job. I had no aspirations at all to be an entrepreneur… in fact, the idea scared the shit out of me.

After a couple of years, I got dissatisfied with the idea of going to work and making somebody else money, especially when I had some bosses who made it very easy for me to become disenchanted.

I always thought things like “if this were my agency, I would do it this way,” but they didn’t listen to me because I was just a little kid to them. 

And so I hustled on the side for a year, building up my clientele and left my salaried job to become a freelancer. I actually doubled my earnings that year from what I was making at the agency, so that was the point where I thought, “yeah, I think this entrepreneurship thing might be for me.”

Building an agency

After several months as a freelancer, I found himself wanting to take a step forward. And as luck would have it, so did my former colleague, Kevin Springer, who I met at my last agency and who coached me on sales and entrepreneurship.

So when Kevin told me, “I’m going to go out on my own, maybe start a consultancy or something,” I immediately thought: that’s the guy I want working with me. 

I didn’t want him to be an independent consultant or start his own business, I wanted him to work with me. I remember driving with him and just saying, “why don’t you join me?” 

A few conversations later, we started an agency together.

Kevin and I shooting a video in June 2017 - 10 years since we first met in the agency.

Kevin and I shooting a video in June 2017 - 10 years since we first met in the agency.

We grew our agency, Headspace, to a ten-person business over the next five years. The agency always earned us a living to pay our bills, but it never became very profitable or scalable. We did good work, but we made a lot of mistake on the sales and operational side of things.

Our projects ran over budget and we didn’t ever charge the clients enough for it. We let the sales cycles go too long, we took too long to get paid, we were always wrestling with cash flow and never had enough money.

That’s when we began to experiment with building our own products.

Tinkering with SaaS products

In 2011, three years after Kevin and I joined forces, the business was just kind of going along. 

Sometimes it was profitable, and sometimes it wasn’t, but we were always talking about products and how in our hearts we really loved selling products, not services.

We started building several products in-house before Proposify, including a DIY website builder (before Wix and Squarespace), and a social media monitoring tool (a dummied down version of Radian 6).

They all failed miserably, for one reason or another, but it taught me a lot about how not to build a products.

  • For one, trying to build an internal product with agency resources is extremely difficult. You need a dedicated developer to work solely on the product.

  • Building a product simply because you see a market opportunity is a bad idea. You need to be passionate about the problem your solving.

  • You need to do proper customer development and research before taking on a risky and expensive MVP build.

Scratching My Own Itch

The idea for Proposify had started long before the team began building it.

Even in my early agency days, I was frustrated by the proposal process, with proposal creation being assigned to junior designers and taking long hours to complete.

I sketched some wireframes back then, and would occasionally pull them out of a desk drawer in my basement to revisit them.

Finally, after two failed products, we thought that maybe it was time to give my proposal software idea another go.

We worked with a developer on a very rough version of the idea, exchanging design services with him so we didn't invest a lot of hard cash. 

There was an event called Demo Camp going on in Halifax that I was told about the day before the event, and when I heard about it, I decided to go pitch. 

To my surprise, people loved the product and later came up to me saying things like “holy shit, this is awesome.” 

Proposify in its current state

Proposify in its current state

There was also somebody in the audience from the local government. We’re blessed up here in Canada to have things like the Atlantic Canada Opportunity Agency (ACOA). They’re federally funded, and basically they can give grants to businesses they believe in. Somebody from ACOA came up to me and they said, “hey this looks like something we could help you with.” 

Amazingly, they ended up giving us a grant to help cover the costs of hiring a specialized developer to work on our software for a year. So we put up a job posting, and found Jonathan Down, who is now our CTO. He took on the job and quietly built Proposify with me while Kevin and I tried to keep the agency business running.

Building a Real Product

With Jonathan on board, the team got to work turning their prototype into a real product that customers could actually use.

We hired Jonathan in January, and he took four months to build version one. He basically threw out everything we had before, started from scratch and built it out. 

I had started blogging a little while before then, had put up a landing page and drove a little bit of AdWords to start collecting email addresses and doing a bit of pre-marketing for it. 

So by the time we launched the first version in April, we had a small email list of around 100 people to send it to. 

So four months later, we released it. 

The response was less than enthusiastic.

That’s when we started getting super-specific feedback about the product, and it’s one of the reasons I always tell people that customer development is so important. 

When I was envisioning the tool, I had never thought anybody would want things like proposal templates or online signatures or even metrics to be able to view how long people looked at certain sections. It was very foreign, as that wasn’t something I had ever really needed or done with RFP’s; I thought the pain I was really solving was making it faster to build proposals, but then after enough customer development, it just became clear that people wanted all of these things.

While the initial marketing work began to drive a few signups, Proposify was far from building anything resembling traction.

It was then that Kevin and I decided that to win, they’d have to sell the agency.

Selling our agency business

Kevin eventually found a buyer in a former client, things got very, very ugly.

For a very long time, they kept delaying the deal to crush our leverage, but making sure that we kept all of the staff. We really should have laid off people, as we just didn’t have the funds for them, but we kept the façade in place in order to get this deal to come through. 

Obviously the buyers knew this, and they kept pushing things back to make us more and more desperate. 

While this was happening, we also owed money to the bank, and the bank wouldn’t release the assets on the business in order to sell it. They said that they had a claim on our assets and that we couldn’t sell it without their permission, so we said “well if we sell the company, we can actually pay you back,”, and they basically just said “no, you can’t sell the assets because you owe us money.” 

It was just a massive pain and distraction with the buyers, bankers, lawyers, and meanwhile we’re just dying, and we need to make this sale happen.

Eventually, the sale did happen, though it left Kevin and me with nothing but freedom from the distraction of trying to sell the agency.

To help things along, we received news that we had been accepted to the Canadian Technology Accelerator in Boston, a three-month program for tech startups.

Kevin and me on our first day in Boston together.

Kevin and me on our first day in Boston together.

But the acceptance came with challenges. It meant that we would have to be there for three months, so the way Kevin and I sorted it out, I would go the first month, and he would go the second, and I would go the third. It was just hard with kids and family to be away for that long, and I was absolutely terrified going down there.

We still needed some contract consulting and freelance work to pay our bills and keep our families fed. 

Still, the pair decided to go. The accelerator period would end up becoming a huge turning point in Proposify’s history, but before things got better, they’d get much, much worse.

Things Get Worse

2012 was a horrible year, with my father dying, leaving the cult, getting shunned and separated.

2013 was almost as bad with the agency struggling, the sale delaying, Proposify floundering, debt accumulating and not knowing what the future held. I even broke my foot for good measure.

In December of that year I was super depressed and thinking that I need to get out and do something… maybe go to an event or reconnect with people.

The Event That Changed Everything

There’s this start-up community called Volta here in Halifax, and they were having a pitch competition, so I signed up just to get out there and talk to people and show what we had been working on. 

I ended up winning the pitch competition, which was cool, but even better was that an early-stage VC firm (who looked at us a year ago and turned us down) came up to us afterward and said, “you’re at a point where we could potentially do a deal with you.” 

They were also impressed that we were going to be going to the accelerator in Boston. 

So while we were down in Boston, we heard that this group wanted us to leave to come to Halifax and pitch the board. 

Now, mind you, this isn’t a massive amount of money ($250,000), but for us where we were at the time, this was absolutely huge.

Finally, things began to look up.

The cash hit our account in May 2014, and that was when the purchase and sales agreement was signed for the agency, too. That changed everything, and it was the moment where we both finally thought, “holy shit we’re not going to die.”

Kevin and me at a startup event in Montreal, summer of 2014

Kevin and me at a startup event in Montreal, summer of 2014

Turning Proposify Into a Real Business

A lot of businesses struggle with having a great product but being unable to find the right market, but we had the opposite problem. We had the market figured out, but our product was shit. 

We needed to add features, fix bugs, improve the UI; roadmap stuff that we needed more developers for. So we used the cash to hire another developer.

We could pretty much attribute all the churn we had in those days to things breaking, being difficult to use, or simply missing features that our competitors had. 

Our advisors were telling us, “hey what you have is solid, you just need to spend some money on marketing or use this money to hire a sales team and just get it out there,” and we ignored them and said “we appreciate that, thank you, but we’re not going to do that.”

Two features in particular—pre-made proposal templates and the ability to legally sign proposals online, along with an improved onboarding process—directly resulted in the biggest revenue increase the team had seen to date.

Once the dev team rolled it out, we saw a big bump. You can see there on our chart, it doesn’t look like a big blip now, but on September 30th we had done $958 MRR, which wasn’t a huge jump from the month prior, but then on October 31 we did almost $1500.


All of a sudden, the feedback started getting more positive. 

Instead of people Tweeting things like “your product sucks, you should go work at McDonald’s,” it was like “Wow, Proposify really saved me a lot of time and I closed a deal.” 

We thought, OK, maybe this is an anomaly, but then in November our MRR jumped to almost $2,500, and in December it was almost at $4,000 so it started climbing really quickly.

Now here we are at $3,000,000 in annual recurring revenue and a team of 23 people.

And more importantly, my personal life is in a great place.

I take better care of myself. I balance hard work with spending time with my two adorable sons and amazing, supportive wife, Christina.

I'm still figuring things out, and while Proposify may not be considered a "unicorn", the business is working. I'm much further ahead than ever and working to keep growing and improving.

What I've been through shaped me, and it's why I'm so passionate about helping other entrepreneurs out.

If you read this far, thank you. I'd love if you subscribe to my email list, and if you want the full story, read my book, Free Trials (and Tribulations).