From accidental emails to the brink of bankruptcy, founder horror stories run the gamut from trivial to make-or-break moments.
Laura Lalonde,
“My dad looked at me [and] he was like, ‘If you can’t make money, maybe it’s not a business. It sent a chill down my spine.”
GridBank
At Startupfest in Montréal on Wednesday, four Canadian founders—from leaders of travel software to consumer packaged goods companies—sat down with Storytime Capital managing partner Neil Grunberg to talk about their worst days as startup leaders, co-founder chemistry, and their luckiest breaks.
As company leaders shared their worst moments, the knowing smiles and nods of agreement created a palpable sense of relief among fellow founders in the crowd: If these successful CEOs had moments like this, then they weren’t alone in the rollercoaster of building a startup.
Vishar Yaghoubian, founder of Toothpod, has developed a portable, chewable tablet to clean teeth without water or a toothbrush. But years of research, development, and working with dental experts couldn’t wash away the embarrassing moment of accidentally sending typed notes on an email thread to everyone from an important client call. Luckily, she said with a laugh, AI takes her notes now.
At the other end of the spectrum, Andrew Lockhead, the CEO of travel tech company Stay22, shared how he pulled his company back from the brink of death. The pandemic shutdown caused investors to pull out just a month after Lockhead had assured his team the funding would sustain them. “Definitely regret that,” he said, shaking his head. The company has since come back stronger, building AI into its workflows and securing a $122-million USD investment.
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Laura Lalonde, CEO of user-generated video app GridBank, said her worst day as a founder came before she had ironed out her pricing model and was struggling to onboard customers without losing money.
“My dad looked at me [and] he was like, ‘If you can’t make money, maybe it’s not a business,’” Lalonde said. “It sent a chill down my spine.” The founder shared how she navigated pricing the hard way—by doing more than 200 individual consults with customers. Now, Lalonde says the startup has had thousands of paying customers and more than a quarter of a million videos uploaded to its platform.
Medeloop CEO Rene Caissie, a former surgeon who sold his first company to Telus, told the crowd he’s been through it all: almost going bankrupt, running out of money the day before payroll, and—in an anecdote that appeared to delight the founder-heavy crowd—getting caught not knowing the meaning of EBITDA (earnings before interest, taxes, depreciation, and amortization). But, he assured the crowd, the best founders don’t let those obstacles dissuade them. “When you start listening to very successful founders, you find out that this is normal,” he said. “You just have to grind through it on a daily basis.”
Feature image courtesy Madison McLauchlan for BetaKit.