Going for gold in startup growth through strong investor relationships

What do founders and Olympic athletes have in common? A lot more than you might think. They both dream big, overcome challenges, build networks of support and celebrate victories – whether it’s crossing a finish line or securing an investment. These themes of resilience and relationship building took centre stage at the latest Communitech Breakfast, where the community gathered for valuable insights and discussions.

Rosie MacLennan, a two-time gold medalist and co-founder of Trainwave, kicked off the event with a talk that drew parallels between the challenges of sports and the ups and downs of being a founder. 

“You’re pursuing a goal with a low probability of success but you’re putting everything into it because you believe it can happen,” said MacLennan. “But on that path, there are incredible highs and incredible lows. As a founder, I’ve experienced the highs and lows, but they often come at the same time.”

Trainwave provides mental performance tools and training programs for young athletes, featuring mindfulness, imagery, reframing, breathing exercises, self-talk and emotion tracking. MacLennan said just as athletes have to train their minds alongside their bodies, mental resilience is just as important for founders.

“It’s an adventure and a test of resilience and problem solving,” she said. “You have to get creative and adapt. Those that are able to do that are able to make it through.”

MacLennan co-founded Trainwave to make mental performance training accessible to young athletes, a mission that mirrors the need for mental strength in the world of startups.

“Parents are putting youth in sports with the hopes of seeing a positive impact and hope they develop these skills for life,” said MacLennan. “But because so much of the focus is on physical development, other skills are often taken for granted.”

The breakfast then shifted to a discussion between Janet Bannister, Managing Partner at Staircase Ventures, and Caitlin MacGregor, CEO and co-founder of Plum, who explored the role of relationships between founders and investors.

“I got advice from Communitech on how to be a founder and moved a team of four here for four months for support,” said MacGregor. “These important relationships have been critical to our success and Waterloo has been our home ever since.”

MacGregor co-founded Plum in 2012, creating a talent assessment platform that uses artificial intelligence (AI) and organizational psychology to help companies make better hiring and talent management decisions. Since then, Plum has evolved into a leading platform in its field. 

Bannister founded Staircase Ventures in 2023, focusing on early-stage Canadian B2B software startups. Previously, Bannister launched Kijiji.ca in 2004, growing it to become one of Canada’s most visited websites, and she held leadership roles at eBay.

MacGregor met Bannister in 2019, and Bannister eventually led the $5 million round that Plum closed.

“I would not be where I am today and Plum wouldn’t be what it is today if it hadn’t been for Janet and these investments,” said MacGregor.

Bannister said investments don’t happen overnight and building relationships takes time before any commitments are made.

“Caitlin and I just happened to show up at a lot of the same events, so I got to know her over the years,” said Bannister. “It’s a long process of building that relationship.”

Bannister also said that of six investments she’s made, she knew three of the founders for over five years. However, she encouraged founders not to be discouraged if they don’t have existing connections with venture capitalists. Instead, they should focus on showing up and building those relationships over time.

“I knew Caitlin was sincerely interested in my feedback. I thought this is a founder I can really get behind,” said Bannister.

MacGregor said she felt Bannister genuinely believed in her success, not just the financial aspect. As a result, she chose to turn down another venture capitalist to work with Bannister.

“Janet was here supporting me trying to find the best solution forward, not just for her but for Plum,” said MacGregor.

MacGregor said founders should choose investors who truly believe in their vision and will stand by them during tough times. She said a major mistake is not considering the long-term nature of the relationship, and that transparency and leaning on investors for support are key.

“You shouldn’t think of your investor as your boss or somebody to please,” said Bannister. “You should think about that person as your partner.”

In the end, much like Olympic athletes training for different events, there’s no one-size-fits-all formula for making it to the finish line. Each founder’s path is unique and calls for its own approach and strategy.

“There’s no straight line to success,” said Bannister.