Where's My Money Season 4, Episode 5

Season Four of Where’s My Money?, now a multi-award-winning podcast, has arrived and we will share all the insights covered across the episodes by host Reagan White and his guests.

enable.me partners with rova to bring this podcast to life and stimulate the conversation about finances with everyday Kiwis. Where’s My Money? follows the story of Reagan – a man chasing the Kiwi Dream but feeling stuck living month-to-month – and his discussions with the experts about what he may be doing wrong and how to fix it.

One man. One million dollars of debt. One podcast to find a way out.

In this episode of Where’s My Money?, host Reagan White kicks off the new Reags to Riches series – spotlighting the real-life stories of Kiwis who’ve built wealth from humble beginnings. And few have a story quite like Philippa Middleton. 

From pumping petrol in high heels to launching a business with queues out the door, Philippa shares the gutsy, unfiltered truth of what it takes to build a business that actually works – one that’s grounded in values, fuelled by sacrifice, and designed to make money. Lots of it. 

From Culture Shock to One-Stop Shop  

After jumping onto the corporate ladder with a gig in sales and radio advertising, Philippa thought she’d found her dream job at 91ZM. She was the only woman – and the youngest exec on the team – and had been brought in to change the culture. 

Instead, she found herself in a leadership vacuum. 

“You can be ballsy and gutsy and fiery, but when the culture is rotten and stinks, and you’re just there to get numbers on the board at whatever cost, I thought, ‘Wow. Do I really want to spend the rest of my life doing this?’,” Philippa says. 

It was during a motivational speaker session for local businesses – one she had helped organise – that everything shifted. Sitting in the front row, looking back at people she realised weren’t necessarily more qualified or capable than her, she had an epiphany. 

“Why am I not sitting there? Why am I scared to be in business? It gave me the guts.” 

By the end of that week, she had scribbled down her first business plan. Eighteen months later, in April 2000, she opened the doors. 

And people were literally queueing to get in. 

Strategy and Sacrifice: The Secret Sauce 

Philippa went all-in on her business – financially, emotionally, and physically. The concept? A one-stop shop designed for people just like her. The demand came fast. Too fast. 

“I invested everything I had – all my strengths, talents, and money. And opened the doors,” she says. “I hired 19 people in six months… I learnt about people really quickly – and some really hard lessons.” 

She sought out mentorship, soaked up every piece of real-world learning she could, and kept showing up. 

“You don’t know anything until you’re in the trenches. The buck stops and starts with you – the clients, the people – everything is your responsibility.” 

That meant learning how to lead, how to make profit-based decisions, and how to make a business truly scalable. And while it was terrifying at times, Phillipa says she found freedom and some crucial business lessons in it, too. 

“It didn’t pay off because it was luck. It paid off because it was strategic. It was hard work, sacrifice, and a hell of a lot of determination. That’s the secret sauce,” she tells Reagan. 

Profit, Pressures, and Building Something Saleable 

Philippa now has a firm understanding about what separates a business from a hustle, and what is required to succeed as a business owner in New Zealand.  

She explains that a business isn’t truly a business unless it’s profitable, systemised, and saleable. Otherwise, you’re just buying yourself a job. 

“A lot of people think they’ve got something to sell, and they don’t,” she says. “If you want to get a multiplier on your business, it has to be strong and profitable. People need to see what they’re buying, otherwise it’s just an intangible nothing.” 

Her advice? Run your business as if it’s always up for sale, even if you never plan to. 

“Life happens. Decisions change. If you don’t want to sell it, that’s fine, but you need to be ready to sell it,” she reflects. 

And even after all this time, her philosophy remains the same: the business exists to serve people, not the other way around. 

“The business is not me. I’m there to guide it. Profit is important, but so is making sure everyone gets paid and the business can survive. Money isn’t my god. I just do everything by the book, in my book, and the money comes,” she finishes. 

Listen to Philippa’s full story of how she turned debt into dollars on this episode of Where’s My Money? 

Disclaimer: The Where’s My Money? podcast and the information shared by host Reagan White and his guests does not constitute individual financial advice. If you’re interested in receiving financial advice, you can book a consultation with an enable.me coach. Costs apply.