Why We Didn’t Give Up On Our Business (And Why You… | Proposify

Why We Didn’t Give Up On Our Business (And Why You Shouldn’t Either)

In the last 12 months, Proposify went from having less than 30 paying customers to over 1,100 (and counting). And while I’m incredibly proud of this achievement, I often remind myself that I almost threw in the towel two years ago. Let me explain...

8 min. read

My business partner Kevin and I were balancing building our proposal software with running our web design agency, but progress was slow.

After hiring our now-CTO Jonathan to work exclusively on the product, we finally got an early-stage MVP (Minimum Viable Product) out into the hands of users in April 2013.

The impact could best be described as a fart in a windstorm.

The few people who tried the product didn’t return to it, and when pressed for feedback, even from mentors and investors we knew personally, it was less than heartening.

These were just three of the emails I received from people who didn’t get what we were trying to do.

I’m glad they were honest with me — I’d prefer that to blowing smoke — but it feels like a punch to the gut when people you respect don’t believe in what you’re doing.

Still, we didn’t let the feedback stop us from staying on our path. It wasn’t like every bit of feedback was negative — if it was then it would have given us serious pause and forced us to make the decision between drastically changing our idea or giving up all together.

While these kinds of emails weren’t overly specific or helpful, they did give us the emotional boost we needed to keep going.

In the ten months that followed, Kevin worked on keeping the finances together while I kept talking to users and working on the product in what seemed like an endless cycle of ... design… fail… design… win a little… fail somewhere else… design...

Almost a year passed and we could only retain a handful of customers. Plus, working on the product took the focus away from our agency, Headspace, so it meant that now we had two failing businesses.

I’ve written before about the long, painful process of selling our agency. That dreadful experience combined with the slow progress of our SaaS product was agonizing and I felt like throwing in the towel on multiple occasions — not just on the business, but on life itself. I was that low.

The thoughts of suicide were fleeting, but they were there, and I’m not alone.

I’m very fortunate that I don’t suffer from clinical depression, and I am not for a minute comparing myself to those who have to deal with these feelings on a regular basis.

My point is that entrepreneurship can be a long, lonely road filled with times of despair, and I am lucky to have a trusted business partner I can lean on for support.

The tides change

“I am a great believer in luck. The harder I work, the more of it I seem to have.”
— Unknown

I remember it was just after Christmas and I was at a low point. I felt like I really needed to get out of the house and do something. I needed to meet people.

I looked on Eventbrite for local events and saw that Volta (a Halifax-based startup house) was putting on a pitch competition. I signed up to pitch for no other reason than to just to get reinvigorated with the product.

Much to my surprise, I won the pitch competition.

The smile of victory.

In the audience was a representative from the regional early-stage venture capital firm. They had been looking at us for the last year but felt it now was time to start seriously talking about getting us a seed round.

A few months later, the money was in our account, we sold Headspace, and our life changed. Proposify now had a chance to succeed. Persistence paid off.

Two years later

Last month I was at a party when I saw one of the original mentors/investors mentioned above who didn’t believe in us.

A better man wouldn’t have taken the opportunity to indulge in a bit of gloating. Much to his credit he acknowledged he was wrong and praised the investors who did believe in us.

My point here isn’t to say, “I told you so”, it’s to show that people are often wrong so don’t let them get you down.

When you receive feedback on your product idea you’re going to get the entire gamut from glowing praise to indifference to scorn. If you truly believe in your vision and have even a few people who get what you’re doing, focus on them.

Chances are there’s more of them out there than haters.

How to apply this to your business

Focus obsessively on product-market fit

One of the biggest reasons startups fail is because they don’t reach product-market fit. In other words, they don’t relieve an acute pain point for a specific type of customer in a large, addressable market.

Getting to PM fit is hard and takes a long time, longer than you think. But just because it’s taking a while doesn’t mean you won’t get there.

I remember once seeing Dan Martel speak at a conference, and he said: “Everyone wants the hockey stick, but in order to have a hockey stick, you need the flat part.”

This was what our revenue growth looked like from the day we launched Proposify to January 2015. Everyone tends to look at the big spike at the end without considering the long stretch of little-to-no revenue for a year and a half.

Some people give up before they ever hit the spike because they think it will never come, but no one wants to be the miner who stops digging six inches away from the oil. If you have any evidence at all you’re even close to solving a real need, keep learning and keep iterating until you solve it.

Here are some Ziad K. Abdelnour quotes from his book, Economic Warfare: Secrets of Wealth Creation in the Age of Welfare Politics to keep in mind when you feel like giving up:

“One of the hardest decisions you'll ever face in life is choosing whether to walk away or try harder.”“Until you are broken, you don't know what you're made of.”“Nothing ever stays the same. Just because things aren't good now doesn't mean they will be that way forever....Never quit.”

There’s nothing wrong with having a plan B

We’d all like to be the kind of entrepreneurs who go all in, quitting full time jobs to focus exclusively on their new business. If you can make it work while still keeping food on the table and a roof over your head, that’s great.

But just because you need a full or part-time job to pay the bills, or you need to take on freelance work, scrub toilets or whatever, it doesn’t mean you’re a failure.

In a recent interview with Alex Turnbull from Groove, Zapier founder, Wade Foster admitted he had a similar experience:

“We wanted to make a go of it and turn it into a business, but we were in Columbia, Missouri. It’s not a place where there’s a lot of funding. Businesses are bootstrapped businesses, and so it had to be a side project. We had to keep our day jobs and approach it from that angle, and so that’s where we started.”

There was a time when Kevin and I didn’t know if we were going to successfully raise money for Proposify so we each started our own plan B. Kevin lined up a full-time job (which he ended up turning down) and I took on freelance work just to keep rent paid.

Find Your Community

As I mentioned earlier, it really helped that I wasn't alone during the dark days when things weren't going as planned. Having a supportive business partner makes a huge difference - it was me and Kevin against the world, and for Proposify. We also share a twisted sense of humour so that helped relieve stress on the regular.

You can probably tell by this photo that we're hilarious.

Tapping into what other start ups were doing both on the local and international scene really helped keep my focus as well. Connecting with Volta as I mentioned before, attending start up events, and following growing businesses like Groove, and leaders like Dan Martell reminded me that what what we were experiencing was normal, that founders and dreamers all over world were digging deep to transform their ideas into reality.

They proved it could happen. And that proved we could happen.

Let go of the need for comfort

In the early days of running your business things will be uncomfortable. You’re going to have months when you don’t know how your rent or mortgage will get paid.

You’ll yearn for simpler times when you had a steady paycheque every two weeks. When you could take the evenings and weekends off and not think about work. When you had health benefits and a pension plan.

The times when you feel like giving up are generally the times when you don’t have money, and that’s a pretty good reason to feel stressed, but not a good reason to throw in the towel.

This is what separates real entrepreneurs from wannabes. Comfort will come eventually, but not right now. Embrace discomfort for the time being. Remember, there is no reward without risk.


I wrote this post for anyone who feels like giving up on their business, and I sincerely hope it helps in any small way. While Proposify is not indestructible, we are growing quickly and on stable footing. The last few years have taught me to savour the good times because more challenges will come in the future. When they come, I plan to be ready.

How do you keep your motivation to keep going when times are tough?

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