Business COVID-19 Entrepreneur

One Year Later: Lessons Canadian Entrepreneurs Learned During the COVID-19 Pandemic

In March 2020, the COVID-19 pandemic took over our lives.

What began as a few weeks, quickly turned into months, and now one year later, we still seem to be without a clear date of returning to normal—whatever “normal” may be.

The last 12 months have been plagued with darkness and fear, but there have also been many examples of hope, like creating vaccines in record time, and compassion, as we’ve seen with many social justice movements making strides.

Throughout this turbulent year, businesses—big and small—took on unprecedented changes and these Canadian entrepreneurs rose to the challenge.

Entrepreneurship requires ambition, guts, and adaptability, all of which the following founders have plenty. Here, they share how they navigated the last year and all of the twists, turns, and lessons that came with it.

 

Swish Goswami – Trufan

Swish Goswami – Trufan

Swish Goswami is the CEO of Trufan, an industry-leading audience engagement platform with a strong focus on first-party data. The platform helps brands generate, segment, and activate first-party data so they can retarget their audience whenever and wherever they want. Trufan has made two acquisitions, raised over $4.1M to date (from several NBA players and venture firms), and has customers like Netflix, NBA, NFL, Sony Music, and a plethora of small to medium-sized businesses.

Swish is also a public speaker (3x TEDx speaker) and an advisor/investor in popular social companies like Upstream, FaZe Clan, and Ashare. 

What is the biggest lesson you’ve learned since the COVID-19 pandemic began?

Communication is everything. Since I can’t meet my team members in person, I’ve had to rely on digital tools to communicate with them efficiently. I’ve found that in the beginning I was scared to overcommunicate but as the pandemic continued, my team and I saw a huge benefit in overcommunicating. Since the pandemic started, we’ve ramped up the times we speak as a team besides our weekly Friday team call (adding on a Monday morning huddle and a Hopes and Fears session every three weeks).

What is one practice that you have adopted in the past year and intend to continue post-COVID-19?

Random check-ins. I enjoy just messaging a team member randomly and saying, “how are you doing?” Right now, it’s good to do that since I don’t see people in an office and have no real clue how people are doing unless they’re on a call with me. I feel like the pandemic has given everyone an excuse to check in with their team more often and with their friends/family regularly. I intend to do that post-COVID-19.

How have you remained motivated during these times?

I’ve remained motivated by remembering three things. Firstly, our product is insanely valuable to businesses (especially SMBs) now more than ever. Due to COVID, many retailers had to shut down their physical location and had to open up online shops. Using our data, they are able to locate their tribe online and engage them. Secondly, our team has been rapidly expanding. We are up to 30 people now and I stay motivated by remembering the commitment and sacrifices they have made to work at Trufan. Thirdly, I try to stay motivated by remembering that I’m not alone in this situation. I talk to a small group of Toronto-based entrepreneurs weekly to understand what their problems are. I find myself finding a lot of common problems and I enjoy being able to work them out with the group. 

What’s one piece of advice you’d give to yourself if it was March 2020?

Remember that they are people who are going to be in a much more difficult situation than you. Count your blessings, try to help others wherever you can, and use this pandemic as an opportunity to focus on yourself (sleep better, eat better, and workout).

Tobyn Sowden – Redbrick

Tobyn Sowden – Redbrick

Tobyn Sowden is a digital entrepreneur who has started more than 10 businesses, generating over $250M in lifetime revenue. His current position is CEO at Redbrick, a parent organization to a portfolio of digital companies. There, he is responsible for defining the company’s overall business strategy and vision—including new product development and future business growth. Since founding Redbrick in 2011, the company has been ranked the 5th Fastest-Growing Company in Canada and 2nd in software by PROFIT 500.

What is the biggest lesson you’ve learned since the COVID-19 pandemic began?

The biggest lesson I’ve learned since the COVID-19 pandemic began is the importance of flexibility. We are at a crucial time right now and as a leader, I’ve had to pivot when the data shows me that the world is changing. For example, over the last few months, I’ve had a complete 180-degree shift in my perspective on remote work. I believe in-person connection is essential for building high performing teams but I realized many employees have re-evaluated their priorities and as a leader, I need to adapt and embrace those priorities in order to retain and attract top talent. As a result, I plan to rebuild a new company culture that upholds my values around in-person connection while becoming more flexible for employees. 
What is one practice that you have adopted in the past year and intend to continue post-COVID-19?

A practice I’m going to continue post-COVID-19 is the importance of taking time to disconnect from the screen. I set the goal of getting into a consistent morning routine where I take 20-30 minutes to listen to a podcast between family time and work. Whatever I’m listening to usually gets my creativity flowing and gets me pumped up for the workday.

How have you remained motivated during these times?

The rapid evolution of technology because of the shift towards digital has continued to motivate me during these times. Digital is my passion, seeing so many new ideas emerge, I get motivated to figure out how Redbrick could work to grow them into thriving digital businesses.

What’s one piece of advice you’d give to yourself if it was March 2020?

I would tell myself to be prepared to continuously adapt. That said, with change comes opportunity, particularly in the digital space. As a leader, it will be critical to keep the team motivated and find new ways of communicating so that everyone feels empowered to bring ideas to the table and stay engaged with the work we are doing.

Taylor Lindsay-Noel – Cup of Té

Taylor Lindsay-Noel – Cup of Té

In 2008, Taylor Lindsay-Noel, an aspiring Olympic gymnast, suffered a devastating accident while in training that left her paralyzed and in a wheelchair. Driven to overcome her challenges and transform her situation into something meaningful and extremely valuable to lives, she launched Cup of Té in 2018 with the goal of providing the world’s finest loose leaf organic teas and teaware.

Based in Ontario, Canada, the premium online retailer is dedicated to enriching lives through the experience of premium teas specially made from organic ingredients with each taste offering unique benefits to tea lovers all over the world and every drop telling a story.

What is the biggest lesson you’ve learned since the COVID-19 pandemic began?

The pandemic taught me that you have to be open to change. As an entrepreneur, you constantly run into issues but having a global crisis that affected everyone was something that was very unique. Instead of letting it defeat me, I decided to see the opportunities that could arise from such a negative situation. Being adaptable was and is imperative to our success through the pandemic.

What is one practice that you have adopted in the past year and intend to continue post-COVID-19?

One of the practices I have adopted over the last year is being open to help. So often when you are the founder of a company you try to do everything by yourself. I’ve learned that it’s okay to know what you know and know what you don’t know. The things I don’t know how to do well I now comfortably outsource, which takes the pressure off of me as well as optimizes my company’s potential.

How have you remained motivated during these times?

To stay motivated I started engaging and learning from other entrepreneurs while finding time to spend time with my family and friends virtually. Having my core support system is imperative to my happiness and scheduling time for that has made all the difference.

What’s one piece of advice you’d give to yourself if it was March 2020?

I would tell myself to stay positive. The pandemic is something that will last a lot longer than you ever expected, however, if you stay focused and don’t let the noise on the other side get to you, lots of incredible things will unfold, so be ready for that.

Rajen Ruparell – Endy

Rajen Ruparell – Endy

Rajen Ruparell, Founder and Chairman of Endy, is a serial entrepreneur who has built and invested in a number of high-profile consumer brands in North America and Europe. He founded Endy with the simple aim of giving Canadians a better sleep, with products made, warehoused, and delivered exclusively in Canada. In just over three years, Endy became Canada’s leading mattress retailer and was sold for $89 million to Sleep Country Canada in 2019—one of Canada’s largest-ever e-commerce acquisitions. Rajen continues to be chairman of Endy and maintains its mission of helping all Canadians get a better night’s sleep, including expansion into sleep accessories, charitable partnerships, and donation matching.

What is the biggest lesson you’ve learned since the COVID-19 pandemic began?

Trust your team and trust your leaders.  This is something I’ve always embraced, however, COVID-19 took this to another level. Let’s say your employee wants to go to the gym in the middle of the day. Why not encourage it, as long as their work is getting done? That’s probably something we wouldn’t have felt comfortable with pre-pandemic, and it took a few weeks to get used to, but one-year in, we realize that people are happier and they’re doing better work. Everyone works in different ways.  When you give great people the freedom to do their best work and judge them on the results, you’ll be surprised at what your team can accomplish. The acceleration of this learning has truly humbled me in these past 12 months.   

What is one practice that you have adopted in the past year and intend to continue post-COVID-19?

Amid the daily routine of Zoom calls and phone calls, it’s been essential for me to take multiple 15-minute breaks throughout the day, with intention, without devices. It allows me to pause, reset, and slow down. We typically make decisions at the pace we’re going. If we’re speeding through the day, racing from one meeting to the next, it’s easy to become immersed without the clarity of perspective. Prior to the pandemic, I would go for lunch or take walking meetings. These days, scheduled breaks have been game-changing for me, and mindful pauses will be a must post-pandemic. Sitting in an empty room for 15 minutes is surprisingly rejuvenating.

How have you remained motivated during these times?

As an entrepreneur in e-commerce and tech, it’s hard not to be motivated right now on the business side. We’re seeing fundamental and systemic shifts in consumer behaviour, and an acceleration of an industry in one year that could have taken 10. There’s a ton of opportunity, and no shortage of big problems to solve—and this extends beyond the world of commerce. 

More importantly, when we see, first-hand, the challenges that so many Canadians are facing one-year into the pandemic, there’s endless motivation to give back and make a difference. Over the past year at Endy, we’ve given the gift of sleep to healthcare heroes at 13 hospitals across Canada, transforming call rooms with new Endy mattresses. This helps frontline workers get the rest they need between patients and on overnight shifts, and we’re dedicated to expanding this program to help as many hospitals as possible over the next year. As leaders in the Canadian e-commerce space, we feel it is important to inspire and motivate other companies to step up and give back in their own way, too.

What’s one piece of advice you’d give to yourself if it was March 2020?

Place your POs, take a breath, and embrace the uncertainty that lies ahead.

Sean Hoff – Moniker

Sean Hoff – Moniker

Sean Hoff is the Founder and Managing Partner of Moniker, a corporate culture agency that went from planning retreats, offsites, and incentive trips around the globe to developing virtual team-building experiences and workshops after COVID-19 grounded travel.

What is the biggest lesson you’ve learned since the COVID-19 pandemic began?

Humans (and organizations) are more adaptable and open to change than we often give them credit for. When the pandemic hit, people and many businesses were forced to entirely change the way they approached work and operated, essentially overnight. It was incredible to see the innovation and creativity that came out of the pandemic leading to change in such a short amount of time.

We also realized how much we took the importance of in-person interaction for granted. Before, people would sit together while staring at their phones and avoid engaging with other humans in the real world. When our world flipped, and everything went online, though, we all felt a bit more isolated from our communities of family, friends, and even colleagues, and it took a toll on both our physical and mental well-being. 

People are social creatures by nature, and I hope that when we can be together again, face-to-face interaction will be valued more, and people will be ‘present’ and connected much more than pre-pandemic.

What is one practice that you have adopted in the past year and intend to continue post-COVID-19?

The Moniker team adapted to working remotely very quickly and has thrived in this structure. We all agreed that the ability to live and work wherever made us happiest and improved our on-the-job performance and general happiness levels. We gave up our office as soon as our lease came up for renewal, and will be a fully remote company going forward.

How have you remained motivated during these times?

Having to completely reinvent ourselves and build a whole new business model has kept us pretty busy! The challenges we face each day designing and building new concepts, figuring out how to market them, improve them, and the continual innovation we pour our energy into daily has kept us very motivated. The positive results we’ve seen rolling in and the bright future ahead is what keeps us going.

What’s one piece of advice you’d give to yourself if it was March 2020?

Be transparent about our situation, and challenge our team to share the responsibility of figuring our way out of this together. Give people a clear mandate for what’s required of them, what the goals and expectations are, and then stand back and let them run with it. By giving people ownership and accountability, we made our survival truly a team effort. I wish I had afforded them that level of mutual trust years before.

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