At TechTO’s Together With Women event, three founders shared how they navigate investor doubt, internal pressure, and the realities of building over time.
“We’re here this morning just to set the stage to have a different kind of conversation,” said Marie Chevrier, CEO of TechTO. “Let’s make sure that we are raw and truthful about what it’s really like.”
That framing opened a panel that focused less on surface-level success and more on the choices and tensions behind it.
As part of Toronto Tech Week’s Together With Women: AI, Venture & The Future of Leadership event, three later-stage founders, Shelby Austin of Arteria AI, Candice Faktor of Disco, and Mallorie Brodie of Bridgit, joined Chevrier for a conversation on growth, leadership, and the pressure to keep moving forward when the rules are still being written.
A different approach to starting
Each founder arrived at entrepreneurship differently, and not always through a single moment of inspiration.
“I think there are two types of founders,” said Austin. “Those who have their aha moment and are driven by that big moment, and those who are just meant to be founders and are just going to do the work and look every day with discipline and put one foot in front of the other.”
For her, it was never about chasing a singular breakthrough. That mindset has shaped how she’s built Arteria AI, a company that has raised $50 million so far to apply artificial intelligence to decision-making in financial services.
With Disco, the company idea started with a contradiction. Despite being deeply interested in learning, Faktor and her co-founder realized they had never completed an online course. That disconnect sparked a realization.
“We like learning when it is social, when it’s dynamic, when it actually leads to a transformation,” she said. From that insight, they developed a model for cohort-based learning, supported by AI to reduce friction in delivery and management.
In contrast, the path to Bridgit began with a commitment to entrepreneurship, before there was a product or problem to solve. While in the Next 36 program, Mallorie Brodie and her co-founder set out to find one.
“We called 15 people in the construction industry to learn about their pain points,” she said. “Then we showed up unannounced on job sites with coffee and donuts. We called it crane hunting.” That on-the-ground research shaped what would become Bridgit, a workforce management platform used across North America and backed by more than $40 million in capital.
Navigating investor conversations
At a later stage in the discussion, the founders reflected on their experiences with fundraising and investor dynamics.
Brodie spoke candidly about the types of questions she and her co-founder received early on.
“We talked to a ton of investors who didn’t believe in us because we didn’t have a technical co-founder, or they couldn’t understand why two women were in construction,” she said. “We focused on what we could control. We had a great pitch deck. We knew our numbers. We were prepared.”
Austin described learning to set firmer boundaries.
“If you don’t believe in my TAM, we shouldn’t be on the phone,” she said, referring to the total addressable market (TAM) which is a common metric used to estimate a company’s potential revenue opportunity. Austin now shares her company’s financials early in conversations to filter out investors who are unlikely to proceed.
“There are investors who want to be in your company. Find them. Get to no as quickly as possible with those who are never really coming in,” she advised.
Faktor, who has also worked both as a founder and on the investor side, framed early-stage fundraising as a strategic process that differs from late-stage.
“Really all you have is your team and your story,” she said. “You’re trying to create tension where more people want to be in your round than you need.”
Pacing, pressure, and staying in the work
When the conversation turned to how they manage discouragement and pressure, each founder reflected on how their approach has evolved with the realities of scaling a company.
In the early years, uncertainty was constant and visible progress was rare. To stay focused, Brodie narrowed the timeline.
“What is the one thing we need to accomplish this week to move the business forward?” she said. Those small, tangible goals gave her team something to rally around. “You don’t know if you’re making progress, and you need to find ways to feel like you are,” she added. Today, her lens has shifted to quarters, but that early discipline still anchors how she operates.
Faktor described how reframing helps her process challenges in real time.
“Life happens for me, not to me,” she said. That perspective allows her to treat setbacks as learning opportunities. “What can I learn from this?” is a question she returns to when things go sideways. She also challenged the idea that founders need to have all the answers. “There’s this myth that if you’re the founder or CEO, you have to know everything,” she said. “But it’s okay to learn alongside your team.”
Austin brought a dose of realism and humour to her answer.
“I’m the cautionary tale on the panel,” she joked, before offering a more serious reflection. “I cry. I’m upset.” What grounds her, she said, is a fundamental belief in her ability to get through it. “I start from the premise that I will win. I may not, but that’s the point in my heart. I’m like, I will win.” For her, resilience is not about projecting strength but about staying in motion, even when things are hard.
The three responses reflected different tools, but a shared mindset: leadership, especially at a later stage, isn’t about clarity or control but instead about staying engaged with the work and learning how to navigate through it.
That idea carried into the final moments of the session, when Chevrier asked each founder to share a principle that guides them. Brodie offered one word: “Reinvention.” Austin said, “Keep showing up as your best self every day.” Faktor quoted Viktor Frankl: “Between stimulus and response, there is space, and in that space lies our freedom to choose.”
The panel didn’t wrap with predictions or metrics, but with a reminder about the kind of support that matters most. Katheleen Eva of Standup Ventures, one of the event organizers, closed by urging the audience to act early and with conviction.
“If you believe in someone before the world does, and you’re in a position to act, back them,” she said. “Sometimes showing up in that way is what makes or breaks things for women founders early on.”
