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Canada's Top Entrepreneurs Reflect On Their Challenges

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Nothing is harder than being an entrepreneur: self-sacrifice, countless hours, true diligence and undying commitment.

I interviewed the following accomplished entrepreneurs, who excel at what they do and have been handpicked by the media as ones to watch. Here, they reflect on their past mistakes and share some of their insights with their B2B counterparts when it comes to e-commerce, IT, funding, delegation, sales and scaling too fast.

On working more efficiently:

"Adopting technology tools such as Zoom, and Asana will eliminate unnecessary bottlenecks in real-time".

-Stephen Ufford, CEO at Trulioo, the recipient of the 2017 Lendlt International Innovator of the Year Award

On anti-fraud measures:

"A lesson I learned early on was the importance of having anti-fraud measures that go above and beyond what the credit card companies provide. This is especially important for a company like Voices.com, where we operate as an online marketplace that connects buyers and sellers, and therefore must take credit card payments online. I knew that we assumed a degree of risk when managing these payments, but because of our small size at the time and assuming the best of our customers, we thought the anti-fraud measures we had in place were sufficient".

-David Ciccarelli, CEO and founder of Voices.com (Microsoft, Hulu, Bell, Cisco, etc).

On management softwares, ERP cloud systems & cost-effectiveness:

If there's a few things most entrepreneurs agree on, it's the importance of time-efficiency, decreased operating costs, less required resources and growth rates. Thankfully, there's a plethora of tools worth exploring that will improve all the processes within a business such as cloud-based ERP systems (according to one study, 69 percent of enterprises were using cloud-based software or system architecture in 2014).

"ERP systems are definitely cost-effective at scale compared to the cost of developing a custom solution. A good guiding principle is that companies should only invest in development of systems that are core and unique to their business model."

- Ben Neville, CTO at Breather, whose off-site spaces are used by hundreds of the most creative companies on the planet.

On employee management:

"A key lesson I've learned is to surround myself with smart, hard-working people who can lead different aspects of the business that aren't my strongest suit. Having a diverse group to share ideas with is also helpful because you have access to a large wealth of knowledge and experience to pull from and it forces us out of our comfort zones to rethink how we do things.
Transparency breeds efficiency. Communicating effectively and collaborating with teams across departments helps to ensure projects and tasks critical to the product roadmap are completed on time".

-Stephen Ufford, CEO at Trulioo

On growth-related problems:

Ah, the delicate act of balancing the challenges and temptations that growth brings to small and medium businesses:

"(We) quickly proved that our approach does drive very high employee participation even in complex and hard-to-engage organizations. We thought that this early, demonstrated success would drive growth by itself. But it turned out that we were solving a problem that most people thought could not be solved. And until people have focused on a problem and are actively looking to understand and solve it, they are very hard to sell to"

-Brad Palmer, CEO, Jostle Corporation, whose services are used by Coldwell Banker, The Onion, etc.

"In the beginning, we never expected to grow as quickly as we did. (One) day, a major publication told the world we were revolutionizing healthcare, and it turned out a huge number of healthcare professionals wanted to join the revolution, all at once. If you're not expecting it, it can quickly become a nightmare. One thing we've learned: When you get big, stay small. As our teams have grown, we've split our organization down into autonomous teams that are the same size that Figure 1 was in its first year. Each of these teams is fully autonomous, capable of moving as quickly as we did when we started the company. As the organization grew and we added roles like data scientists and QA analysts, we realized we had scaled up the team but not the process".

- Richard Penner, co-founder & CTO at Figure 1, which app got featured in The Wall Street Journal, The Atlantic, CNN, etc.

"A major challenge of being "high-growth" is the breadth of opportunity in front of you - it's everywhere you look and often more than you can handle all at once. It's tempting to spread the teams thin and jump at everything, but most often that is not the right answer. We needed to learn the hard way that success follows focus. (It) can be difficult to find the right point between moving too fast versus moving too slow, but never underestimate the need to build a strong foundation on which you can scale. (That) may appear to slow you down in the short term, but in the long term it will be what helps you maintain the momentum you build".

-Tyler Douglas, Chief Sales & Marketing Officer for Vision Critical, whose services are used by numerous Fortune 500 companies

"The downside of being a fast-growing company is that it's easy to focus on the wins and overlook the fact that you need to have processes in place. (At) Thinkific, as we scaled up with people and growth, we started to notice cracks. (Fortunately), instead of overlooking this, we proactively fixed them by setting up the right processes and aligning the entire company on direction and values. We have a team in place to ensure that we operate, as much as possible, as a well-oiled machine"

-Sid Bharath, VP of Growth at Thinkific, which counts many consumers and companies (such as Hootsuite) running their online courses on their platform

On business priorities:

"The more you can use your time to serve customers, listen to them, and think about how to make better products, the faster your business will grow. You need to limit the time you spend on activities that are not about your customers and building a great team. I put in this category tech events, social media and even equity financing".

-Pierre-Alexandre Fournier, CEO at Hexoskin, and which products are sold at Best Buy and were featured in The New York Times.

On losing focus:

"It's tempting to get distracted by good (but not great) sales leads or executing on good (but not great) projects. (We've) learned to only execute on the things that matter. If something doesn't fit the smell test, we need to be vigilant and ruthless in putting it aside".

-Jeff Desjardins, President at Visual Capitalist, which was featured in The Wall Street Journal, The New York Times, Business Insider, etc.

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