Simon Squibb on why anything is possible, and small businesses matter more than ever

Pictured above: Simon Squibb and Richard Conway.

When British entrepreneur and investor Simon Squibb landed in New Zealand to visit family, he didn’t expect to leave having helped turn a local café worker into a business owner. But that’s exactly what happened.

While in Auckland earlier this year, Simon Squibb met chef Navseerat Kaur – an aspiring entrepreneur working in a local café – and quickly became involved in helping her take over the business and relaunch it under a new name: Pink Broccoli. It was a real-time demonstration of the philosophy that has driven Squibb’s work in recent years: Help people start before they feel ready.

In an exclusive interview with NZBusiness owner Richard Conway, Squibb reflected on the catalyst that first pushed him into entrepreneurship.

At just 15 years old, after his father died suddenly, Squibb found himself homeless and unable to get a job. “I basically couldn’t get a job and I couldn’t get help from social services,” he said. “I describe this moment as like the entrepreneur muscle woke up in my brain.”

That “muscle” led him to knock on the door of a large house with an overgrown garden and offer to tidy it up for money. “From that moment, at 15 years old, I created a gardening company. That’s basically the story.”

Three decades later, Squibb has started more than 19 companies, invested in over 78 start-ups, and sold his agency, Fluid, to PwC. Yet his focus has shifted dramatically from building wealth to building others.

“I’m just helping the 15-year-old me,” he told Conway. “I want to put the ladder down.”

That mindset now underpins HelpBnk, his platform connecting entrepreneurs with people willing to offer time, knowledge or capital. Squibb describes it simply as “entrepreneurs helping entrepreneurs”, a way to scale the help he can personally provide.

He is also vocal about what he sees as systemic barriers holding people back, particularly in education and public policy.

“The school system asks, at a very young age, the wrong question to kids,” he said. Instead of asking children what job they want, he believes we should ask: “What problem will you solve?”

On government support for business, Squibb was equally direct. “Without small businesses, there are no big businesses,” he said. “Governments need to change their strategy. They need to help small businesses.”

Having reviewed the numbers behind the café Nav was taking over, Squibb saw firsthand how hard small operators are squeezed. “These businesses are squeezed like an orange,” he said.

“Just surviving, hoping somehow for some miracle.”

For Squibb, backing small business isn’t ideological – it’s practical. “When the little businesses work, they’re contributing so much to the direct economy,” he said. “Isn’t this just common sense?”

Beyond policy, however, the interview returned repeatedly to mindset. Fear, he argues, isn’t something to eliminate but to leverage. “Fear is a superpower,” he said. “Lean into it.”

And if there’s one message he wants New Zealanders to take away?

“Anything is possible,” Squibb said. “Don’t let the systems stop you following your dream. Don’t let money be the excuse. Don’t let the government be the excuse. Take agency over your life because it’s actually up to you.”

As Pink Broccoli begins its new chapter under chef Nav’s ownership, Squibb sees something bigger than a single café changing hands. He sees proof that when someone shares a dream, others will step forward.

“You can’t do it alone,” he said. “But if you dream and tell enough people that dream, someone will be able to help you make it happen.”