How to Craft a Start-up Story That Sells
Want to hear a good story? The answer, according to brain science, bestsellers and bingeable TV series, is a resounding yes. A powerful narrative can change perspective, build empathy and light up neural circuits. There is even evidence that storytelling skills may contribute to longevity.
All of which makes storytelling a requisite business skill, particularly in Canada’s startup community, where every breakthrough innovation starts with a pitch. Having a clear narrative around what is being built is critical—whether at a pitch competition, in meetings with prospective clients or when securing the next round of funding. “Storytelling is a superpower for founders,” says Zeeshan Ali, a partner at Toronto-based Wittington Ventures.
In his role, Ali hears a high volume of pitches and evaluates the viability of emerging solutions in climate and healthcare. For early-stage founders without significant traction or a finished product, storytelling often functions as the product itself—supporting not only capital raising but also customer acquisition and broader market interest. Ali shares insights on how to craft messaging that resonates with investors, balance complex science with compelling narrative, and avoid a common multi-billion-dollar mistake founders make.
Can you tell us a good story that illustrates the value of telling a good story?
Just this morning, I spoke to a founding team building an AI companion for individuals with Alzheimer’s in a care-facility setting. The care chatbot speaks to Alzheimer’s patients during staff off-hours and tracks what they’re doing throughout the day, which is unlocking data and insights not only for their families, but also for care facilities. It can have a big impact. Stories like that get me extremely excited for the world that is evolving around technology.
How can a founder use a pitch to connect with investors, clients or their own team?
A good story is anchored in simplicity and founders being able to get their point across. Why are they building what they’re building? Why is the problem significant? Why is it an unmet need? Building up the narrative around the “why” enables a founder to explain what their solution is.
At the early stage, as part of capital raising, an investor is betting more on the founder [than the product]. Communicating their background, experience and passion for what they’re building is fundamental to being a great storyteller.
There’s a lot of emphasis on providing hard data to support the potential value of a venture. How does storytelling fit into the picture?
Within the healthcare setting, where you have regulations and consumer trust that needs to be garnered, the best way to back your technology is with validated data and expertise. At the same time, that needs to be linked to the future vision and strategic insight of where a certain industry is going. Bridging those two worlds is where I’ve seen founders truly succeed in raising capital and building confidence.
Do you have an example of that?
I was an early investor in the world of AI scribes. At the time, clinicians were very hesitant to have AI record conversations with patients. But the opportunity to accurately capture what your patient is saying and reduce the amount of after-hour work has been a gamechanger for clinicians. When the company was scaling, the critical validation point was the amount of growth the company was having in terms of clinician adoption. And allowing clinicians to focus on their patients, and not be heads-down writing, allowed them to create connections with their patients. Two years later, that market has since ballooned, with multiple AI scribes and incumbents building their own scribes.
Speaking of storytelling, an AI scribe featured in a plotline on season 2 of “The Pitt.” On a related note, it can be difficult to convey complex technical ideas in narratives that resonate with a wide audience. So what’s your advice on managing that balance?
I always tell founders that capital raising is a journey, with multiple touch points. In the first conversation, you’re building a relationship with your investors. And as you progress to a second and a third conversation, that’s when the science, the details, the technical elements of the business can come through. I think investors appreciate being educated on the “why” behind what they’re building, because founders are truly the experts.
But they might not be the experts in storytelling. Where can they get help to craft their narrative?
For an early-stage founder, there are a number of resources. There are multiple innovation hubs—MaRS being one of the largest—with advisory support to guide founders as part of their development. Investors are a great resource as well. I’ve seen tremendous value from founders coming to me and ideating around what they’re building. And thirdly, the founder-peer community is very strong, especially in healthcare here in Toronto.
How should founders be thinking about structuring their pitch for the most impact?
Even before starting their pitch, founders should start with better understanding the investor. What are they investing in? Why? Understanding the investor’s focus area, the background of the fund, can help them tailor their story.
Can you give me an example of how they could do that?
It’s as simple as a founder saying, “I’ve done research on the fund, but can you articulate the investment thesis, average cheque size, how many deals you’re doing a year, and what you look for in a founder?” That insight can be tremendously valuable for a founder to understand the investor’s bookends so they can articulate some of those elements as part of the pitch.
I would add that investors are looking to build portfolios of companies that can be synergistic and strategic. Founders that do the work to understand where an investor has potential white space in their portfolio have an amazing opportunity to articulate that as part of their story.
Tailoring your message to your audience is always important. How do you recommend tailoring a message to a public audience, especially in healthcare, where it’s so important to be credible, empathetic and not overpromise results?
A great story can hit upon all those elements and it’s absolutely critical in healthcare to build consumer, customer and investor trust. It’s important to build a narrative backed by science and research as well as the founder’s story—their credibility and background.
Related: How to Pitch Your Start-up to Investors
If you could remove one common mistake from all pitches, what would it be?
Founders believe they need to overindex on market size. For me as an investor, it’s more about the thought process: how will they build up the market size for their business? I’m more interested in understanding a market, walking through the process and the rationale, as opposed to hearing “I’m building in a hundred-billion dollar market.”
How can someone know if they’re actually delivering a compelling pitch?
I would treat capital-raising like a sales process. From a founder perspective, in addition to telling a good story, you’re trying to build a great relationship. The right signal in terms of whether a story is landing happens after that first conversation—if there’s interest in a follow-up conversation and a follow-up from there.
Dominique Ritter writes about technology for MaRS Discovery District. Canadian Business has partnered with MaRS to showcase innovation in Canadian startups.

