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Kyle Racki, Co-founder and CEO of Proposify
Kyle Racki
Co-Founder and CEO - Proposify

Overcoming Challenges as an Entrepreneur

Published on

Takeaways

  1. The startup ecosystem in Canada is healthy, from the access to government supports to the climate of cooperation and support among entrepreneurs.
  2. Entrepreneurs have to have an obsessive drive not only to make their business successful, but also to build a product or service that provides value to people.
  3. Entrepreneurs are a rare breed that excel away from the norm, who require the drive and willingness to break the rules.

Action

Government should put more emphasis on giving resources to underrepresented groups to help them become successful entrepreneurs. There are systemic problems that still exist in the country limiting the potential of underrepresented people. With their empowerment, the country will soon see the net benefits of their success.


What are the strengths and weaknesses of the Canadian entrepreneurship ecosystem? 

I live a little bit in my own bubble, focusing on my own company and the city that I am in, so I do not have a broad perspective of what is going in Canada. However, what I can say about living in Atlatnic Canada or Halifax, Nova Scotia, is that there are not a lot of funding opportunities. There are a ton of government grants that we rely and depend on, which gave us a huge leg up that our American counterparts likely wish they could get. There is a lot of support from that standpoint.  

I know by talking to our investors who are based out of Toronto, the Canadian Business Growth Fund (CBGF), a lot of their philosophy around startups and investing in Canada has been that Canada places a lot of emphasis on the startup but very little on the scale-up. The few ones that we know of—the Shopifys and Hootsuites—they rely on a lot of American funding in order to scale up operations, and usually have to move or at least have some kind of a presence in San Francisco. That is my high-level take on the Canadian startup ecosystem.  

“Canada places a lot of emphasis on the startup but very little on the scale-up.” 

From what I hear talking to other entrepreneurs, and this maybe is limited to Atlantic Canada, for some early stage companies, it is very difficult to get funding. You usually have to have some level of traction in the market and some level of revenue, and the bar is being raised all of the time. Locally, one of our investors is Halifax-based Innovacorp, and the bar is around $10,000 monthly recurring revenue or similar in order to get investments. The bar was much lower before, and we would not have qualified when we first went for it five years ago. For really early stage companies, getting seed capital is harder and maybe that is when they have to go to the US to get funding. 


What were some of the challenges you have faced as an entrepreneur and how did you overcome them? 

The year of hell was about four years into my business, around 2012. That year, all the personal losses compounded with a lot of business failures. In one year, I lost a belief system, which I had been raised up with—it was a very evangelical kind of cult. I woke up from that and realized I did not want to be in it anymore, which resulted in the loss of most of my family and community. My father died the same year, I got divorced, and my business was essentially running on fumes. I did not have enough money for the bridge toll to get over to work one day. That was the year of hell and it was really more like two years of hell but thankfully, I am in a much better place today. 

“The more I am pressed down, the harder I work to push through it, which is a good trait for entrepreneurs.” 

Having the support of my business partner, Kevin, was pretty key because he is almost like family or like a replacement older brother. I got support from him and other people, and I knew there was another community willing to open its arms while I was going through those struggles, and it was really the entrepreneurial startup community in Halifax for the most part. We worked through it. I have a little bit of natural, ingrained stubbornness, or resiliency, where the more I am pressed down, the harder I work to push through it, which is a good trait for entrepreneurs. 


What are the core traits of an entrepreneur that you think are the most important? 

That is a great question and one that I love talking about because there is something unique about entrepreneurs and you do not get any real training in school for it. The school system is generally there to create employees and they train you how to be a good employee, how to study, follow the rules and do what you are told, and usually entrepreneurship requires somebody who is ready and willing to break the rules in order to create something new. There is a little bit of that rebellious streak that a lot of entrepreneurs have. There are classic, overused examples that are still worth saying like Mark Zuckerberg, Bill Gates, Steve Jobs, and probably many others who are college dropouts, and there is a reason for that.  

“Entrepreneurship requires somebody who is ready and willing to break the rules in order to create something new.” 

I received average marks in school: 60s, 70s, sometimes 80s, but I was not academically gifted and I did not know I wanted to be an entrepreneur. All I knew was I that liked design and creativity. There are a lot of different factors and traits that go into an entrepreneur but the important ones are resiliency, problem solving, the ability to take abstract concepts and crystallize them, and most importantly, move on them. Do not sit around for years dreaming but actually put pen to paper or fingers to keyboard and just make it happen.  

“Entrepreneurship requires somebody who is ready and willing to break the rules in order to create something new.” 

The transition that every entrepreneur makes as you start to scale is trying to figure out how to become really good at a lot of different things, whether it is sales, marketing, or product development. You usually have to be very good at putting your head down and working your butt off for hours and hours a day and probably sacrifice a lot of other parts of your life, such as not spending as much time with your friends and not going out as much. You have to be almost obsessive about building the business in order to make it work. But then once it actually is working and it is starting to scale, and you are now hiring people, that next piece is where a lot of entrepreneurs struggle because they are so good at doing the work, but they do not know how to hire right or lead effectively. They usually do not learn strategic planning frameworks, how to run one-on-ones, and how to do an effective all-hands presentation. Those are more of the leadership traits that a lot of entrepreneurs do not have and they need to learn them. 

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What advice would you give to other entrepreneurs or your younger self? 

Entrepreneurship is really important and I like to talk about it because a lot of kids and young people do not understand that this is available to them. There is more awareness around the space now. In the last 20 years we have begun talking about entrepreneurship in a way that is almost cool, like entrepreneurs are rockstars. You have people like Gary Vaynerchuk, who gets stopped on the street for selfies; you have Jeff Bezos in celebrity gossip magazines. These kinds of things were not really happening in the 1980s and 1990s for entrepreneurs—entrepreneurship was not cool, it was usually just nutcases who decided to go and start businesses.  

“In the last 20 years we have begun talking about entrepreneurship in a way that is almost cool, like they are rockstars.” 

Entrepreneurship is cooler now but the fundamentals of business have not really changed that much just because the mechanism to deliver products is different. It is easier to distribute and hosting costs are low now. You still have to grind it out and you still have to struggle for a long time because it is not going to magically happen. Sometimes, younger people have this notion that just because it is cool now to be a tech entrepreneur, that it is a really fast path to success but it has not really gotten easier. Entrepreneurship requires being obsessive about not just trying to achieve wealth but trying to solve a really important problem. If you focus on delivering value to customers and solving their problems, the money is just a natural by-product. A lot of people chase the money and the more you chase it, the more it eludes you. 

“Take complicated concepts and try to make them digestible and easy to understand, and that trait naturally correlates to sales.” 

I was never formally trained in sales but I was formally trained in speaking and teaching because that was in the religion that I grew up in, where there were weekly trainings on public speaking and that kind of thing. That is the approach I have always taken, which was to take complicated concepts and try to make them digestible and easy to understand, and that trait naturally correlates to sales. That is one thing. Then the other thing is that if you get really good at creating content that people find enjoyable, entertaining, or valuable in some way, it creates and forms trust and bonds with potential buyers. They are more willing and likely to buy from somebody that has taught them something than somebody just coming in with a hard sell. 


If you had 30 seconds to pitch anyone to improve the entrepreneurship ecosystem in Canada, what would you say and to whom? 

I would try to convince government to put more emphasis on educating and giving resources to underrepresented groups, particularly Black and Indigenous people. There is a huge opportunity to offer a level playing field to other members of the community. I do not think it is a coincidence that a ton of us tech entrepreneurs or just entrepreneurs in general are white men. It is very systemic, and just by offering more opportunities to other underrepresented groups, we will start to see the net benefit of that in 10 to 20 years. 

“Anybody who is used to fighting every single day is going to try harder and work harder and that is going to line you up for success more than just having cash in the bank.” 

It is funny because for entrepreneurs who have had big successes, wins, and have gotten their companies acquired, often their next business fails because they have gotten a little soft and they have had more money and access to resources so they have not tried as hard. But if you take somebody who basically is ready to live on the streets and then give them resources, they are going to be really dangerous because they are used to fighting. Anybody who is used to fighting every single day is going to try harder and work harder and that is going to line you up for success more than just having cash in the bank. 

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Kyle Racki, Co-founder and CEO of Proposify
Kyle Racki
Co-Founder and CEO - Proposify

Bio: Kyle Racki is the Co-Founder and CEO of Proposify. He started his first business, a web design company, at the age of 24He is a prolific blogger who has written 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. 

 

Organization Profile: Proposify is an SaaS company that provides proposal software giving more control and insight into the proposal process, from design to sign-off. They work with over 10,000 sales teams worldwide and have assisted with the creation of over hundreds of thousands of proposals. With Proposify software, clients can now save pre-approved templates, set parameters for unique user roles and permissions, sync data through an integrated CRM, and more.