At a flagship Business event in April, journalist Dougal Shaw chaired a panel of three experienced entrepreneurs discussing failure, resilience, and what it truly takes to scale.
Shaw, author of a new book called Fail Smarter, brought together founders at the Business Design Centre to challenge the polished success narratives that typically dominate entrepreneurial conversation.
The panellists were Steph Hind, co-founder of employee wellbeing benefits platform Heka, Gurinder Dhillon, founder and CEO of electric vehicle leasing company Auto Car, and serial food entrepreneur and investor John Stapleton.
Stapleton is the founder of New Covent Garden Soup Company and Little Dish, and his business card tells its own story by listing all three ventures, including one failure sandwiched between two successes.
Hind closed her first investment round the week before Christmas 2019, only for Covid to hit six weeks later and shut down every physical experience on her platform simultaneously.
“Every gym, every physical location we had on the platform closed,” she said. “And literally overnight you had people being like, what are you going to do for us now?”
Aged 26, with new staff who had joined on the strength of her conviction, Hind chose to reframe the crisis by asking what the best possible outcome could look like rather than fixating on the worst.
Heka pivoted to a whole-person health model and now offers around 25,000 experiences, ranging from financial learning to National Trust membership, having been stress-tested at the very start of its existence.
Dhillon’s path to building a fleet of 8,000 vehicles and becoming Uber’s biggest partner in Europe began with an earlier food delivery business that generated strong sales but could never find a profit.
After four years, he acknowledged he was stubbornly pursuing a future for his food delivery company that simply did not exist, describing stubbornness as continuing regardless when all the facts have already changed.
He later built a fleet of 250 black cabs, but when Uber arrived he read the disruption as a signal and sold the business rather than fight the tide, describing it as the bravest decision he ever made.
“It’s not timing the market, it’s time in the market,” Dhillon said. “You gain expertise from compound interest and spending time building your knowledge in that area.”
Stapleton’s failure came after selling New Covent Garden Soup Company in 1997, when he took the model to America with what he later acknowledged was misplaced confidence.
“I became a bit of an arrogant s**t at that stage because I thought I had it figured out,” he said, describing how the venture eventually came crashing down around him.
A prolonged period of introspection followed, during which Stapleton said his mind played tricks on him, leading him to wonder whether New Covent Garden had succeeded despite him rather than because of him.
He credits that American failure directly with the success of Little Dish, stating plainly that “the major reason why Little Dish was a success was because the US business was a failure.”
When the panel turned to how investors view founders who have experienced failure, all three agreed that the best investors probe setbacks carefully rather than being automatically deterred by them.
Stapleton noted that investors consider how people were treated when things went wrong, asking whether those around the founder were “left in debt and out of pocket, or did you manage to settle up.”
The panel concluded that founders who have failed hardest often scale the fastest, provided they can construct an honest narrative demonstrating genuine growth from the experience.
Shaw will continue exploring the themes of Fail Smarter at a dedicated session on 2 June, where a special guest entrepreneur featured in the book will also appear.