How entrepreneurs nail big presentations (hint: wear lucky socks)

It’s easy to freeze when the spotlight is on and the stakes are high. Here, five startup founders share their secrets to making the right impression when it matters most.

An essential skill for entrepreneurs is knowing how to make a case for their business, whether they’re raising funds, seeking out new partnerships or securing new clients. And as venture capital funding is drying up — investment dropped by 82 percent in the first quarter of 2023 compared to last year — founders have to make every meeting count. That’s why we turned to five startup founders to get their secrets on preparing for big meetings. They know how to nail a pitch, present with confidence and pivot gracefully. Their pro advice can help anyone be their best self in the boardroom.

Zero in on the key takeaways

Entrepreneur Louis Brun starts preparing for a big meeting days in advance by distilling his ideas down to three messages he wants to communicate. Brun is CEO and co-founder of Sollum Technologies, which makes smart LED lighting  systems for greenhouses and closed a $30-million financing round in January. “Make sure investors can take the information away with them and take ownership of it,” he says. Brun also keeps notes in his phone, which he reviews right before the meeting to refresh his memory. When it comes to fielding questions, he keeps his answers short and sweet. “I like to be to-the-point. I always come back to what I want the investor or customer to take out of the meeting.”

Don’t stay up too late

Try to avoid revenge bedtime procrastination the night before a big meeting. It’s easy to get caught up with answering emails, scrolling social media or even doing some last-minute meeting prep. But having a restful evening before a big presentation can make a world of difference, says Caitlin MacGregor, the CEO of Plum, a talent assessment platform for employers and job candidates. It’s important, MacGregor says, to prioritize sleep — you want to be quick on your toes and stay calm if you get a curveball question. “It’s all about showing up as your best self, so discipline around sleep is always something I have to be conscious about,” she says. MacGregor likes to listen to a good fiction audiobook to get sleepy (her latest favourite is the rom-com Book Lovers by Emily Henry). Her prep techniques have proven to be successful: in February, Plum raised US$6 million in funding.

Dream of success

Before an important meeting, Sparrow Connected CEO Chris Izquierdo spends five minutes visualizing exactly how he wants it to go. “It’s a rehearsal in my head based on what I’m expecting the questions to be and what their concerns might be,” he says. Izquierdo always makes an effort to connect with the other party by asking questions. “For example, tell me a little bit about yourself and what matters to you,” he says. “I’m curious to know when you made an investment that failed. Why did it fail? How do you react to a successful investment?” Being inquisitive is a smart approach. Last year, Sparrow Connected, an internal communications platform, received $1.4 million in funding from economic development agency PrairiesCan and is currently raising a Series A funding round.

Give yourself a break

Nivatha Balendra, CEO and founder of Dispersa, a startup that produces waste-derived ingredients for cleaning and personal care, says that it’s important not to put too much pressure on yourself. “We often feel the need to deliver the best-ever pitch,” Balendra says. “But it’s more important to connect with who’s in the meeting rather than focus on delivering a perfect presentation.” Balendra met with around 70 investors while fundraising in April and her time and energy paid off: Dispersa secured financing of $3 million to fund its growth. “I became more confident over time,” says Balendra. “And I grew more comfortable with making quick changes on the fly because it became more natural.” Her advice? Focus on positive statements and treat yourself with grace. “We’re all humans — even if we don’t perform our best.”

Dress the part

What you wear can have a major impact on your confidence, whether it’s a suit that makes you feel powerful or a meaningful piece of jewellery. Philip Poulidis, CEO and co-founder of Odaia, an AI software startup for the life-sciences industry, has a pair of lucky socks he puts on whenever he presents to investors. “My co-founder, Helen Kontozopoulos, attended a venture capital event around the time we started the company and someone there was handing out socks,” he says. The pattern features narwhals spearing dollar bills with their tusks. (The narwhal is the Canadian version of the unicorn, representing billion-dollar valuation companies.) Poulidis says his lucky pair of venture capital pitch socks isn’t about superstition — it’s about frame of mind. “It’s part of me psyching myself up for fundraising, the way athletes would prior to a game. I can’t lose with the socks on,” he says. “I wouldn’t hesitate to design our own socks if these ones wear out.” Poulidis’ winning attitude has paid off. In May, Odaia secured $34 million in Series B financing.

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Photo illustration: Monica Guan