I Went On The Chase! Can You Really Win Your Way Out Of Debt? 

Dec 1, 2025 | Where’s My Money?

Where’s My Money? Season 5, Episode 9 

Season Five of multi-award-winning podcast Where’s My Money? is back to shed light on the common money questions New Zealanders are asking. 

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. 

Many of us dream of winning our way to wealth. We have conversations at dinner tables that start with “if I won Lotto…”. There are thousands of seasons of television shows focused on contestants winning cash. 

But is it the golden ticket it seems? 

This week’s episode of Where’s My Money? explores three different types of windfalls – gameshow prizes, Lotto, corporate giveaways – to see if it’s the boon promised, and how realistic the hopes of being a ‘winner’ are. 

Making the most of a prize win 

Host Reagan White recently crossed the Tasman to film an episode of The Chase, hoping to win some cash. Spoiler alert: He didn’t come home with thousands in prize money, but he did get to tick off some bucket list dreams – like beating the Chaser. 

Contrasting Reagan’s luck, the first guest on the episode is a recent prize winner. Olivia and her partner Digger won More FM’s Change Your Life prize at the end of August, sponsored by enable.me. 

The prize is a doozy, setting them up with most essential and lifestyle costs for a full year: mortgage, fuel and power, a five-meal bargain box each week, two movie tickets per month, and Uber Eats vouchers. 

To help Olivia and Digger be as strategic as possible with their win, they are also benefitting from an enable.me financial coaching programme and access to an expert financial adviser and coach. 

Olivia shares the impact of the coaching programme in the episode.  

“Our coach [Karen] has been fabulous. She is so knowledgeable and really setting us up on the right track,” Olivia says. 

The couple are almost a month into the coaching programme. At this point, they are examining their spending to identify where they are starting from and the goals they want to reach.  

Olivia shares that one of the most powerful parts of the coaching programme so far has been getting that visibility over their spending. They are identifying the purchases that don’t add to their lives, to be able to reach their goals faster. At enable.me we call this unnecessary extra spending that brings no added happiness ‘fritter’.  

“It’s the frittering money that they try and stop and help you put that in so you can save more money and become mortgage free faster. Like that’s what our goal is: to become mortgage free quicker,” Olivia shares. 

“[Karen’s] pretty much like for everything she said to us, we can cut our mortgage time in half that we will have it, which is incredible. Just by doing these little things that she’s helping us out with.” 

Managing your windfall 

Windfalls can come in the form of wins and prizes – but, more commonly, they can be gifts or inheritance from family members. 

enable.me Financial Coach Karen Beckham, who is working with Olivia and Digger, joins the episode to share her advice for those that find a few extra zeroes in their bank accounts. 

Mainly, that it’s important to get solid financial advice to put a strategic plan in place to make the best of the extra money. 

Karen says, “in my experience working in banks, we’ve had lotto winners that went from winning millions and then having nothing to show for it. So, you’ve got to see someone.” 

“You’ve got to get a good plan. Calm down, relax, enjoy. Take a second. Really have good think about what you want to do and what you want to achieve.” 

Hot tip: If you find yourself with a windfall and you have the itch to spend up large, one way to manage the excitement is to use some of the money to do one thing you want to do but haven’t been able to afford. For Olivia and Digger this was building a second deck they’ve been wanting for years. For you, it could be a holiday, one large purchase, a concert, or experience you’ve always wanted to do. Then, once you have that out of your system, it’s easier to get strategic with the remaining cash. 

I’ve beaten the odds – what do I do now? 

With only a 1 in 38.3 million chance of winning First Division Lotto* – per line – it’s important to remember that Lotto is gambling and you are many times more likely to not get any money back in your pocket after you buy a ticket.  

In saying that, what is it really like to come up trumps and win Lotto? It’s such a widely talked about topic, but it’s rare to hear winners sharing how they use their win to benefit their lives.  

Gerald Trass did just that in November 2013. He went to Four Square for his weekly shop, bought a ticket and won $10,000,000. That’s a lot of zeroes.  

It felt surreal for him – and changed his life, instantly. It did take some time to get used to the idea.  

He says, “and from that moment for the next month, I think I averaged one hour sleep a night per night because I was so amped, just naturally amped that I couldn’t sleep.” 

His first purchase? A luxury car he’d wanted for a long time. His second? An apartment to live in.  

From there, he chose to be careful with the rest of the windfall.  

“I wanted to be very careful because I was conscious… often in my life I’ve not had a lot of money so I knew what it’s like to be poor or without a lot of money and then suddenly I had a lot – so I thought ‘I need to take steps to make sure I keep it’.”  

Gerald shares the rest of his story, and his reflections on relationships, life and, more generally, the concept of money representing freedom. If you use it well.  

Interested in hearing more? Watch the full episode here:  

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. 

*Lotto Play Smart: https://mylotto.co.nz/play-smart/did-you-know#:~:text=Powerball%20always%20offers%20you%20the,or%20won%20in%20the%20past. 

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