I came across a young woman the other day who had tried to start her own business.
Her name is Tracy, and her promising start-up had already collapsed, leaving her almost $100,000 in debt.
Starting a business is hard. Growing one is harder. That’s why we study the few that make it — those that flourish and eventually list. But even for them, future success is never guaranteed.
Tracy ended up declaring bankruptcy. While this may seem a catch-all way to end a financial predicament, it has serious ramifications. You have to declare it when looking for work. You can’t get credit, even for simple things like connecting electricity.
Her story does end happier. By applying herself to side hustles seven days a week, she eventually repaid her debts, started a workable business, and bought two properties.
It was interesting to hear about these side hustles. The most lucrative of them involved working for what I would term ‘toll gates’ or ‘ticket clippers’.
Source: Guillermo Fernandes / Flickr
When the Covid lockdowns lifted in 2020, Tracy made $2,000 in one day as an Uber Eats driver.
Later, putting her property on Airbnb generated cash flow.
In New Zealand today, unemployment is now the highest it’s been since Covid lockdowns wrecked the economy in September 2020.
5.2% unemployment is worse than it sounds because it doesn’t include those who have some work, but not enough. The underutilisation rate for the quarter to June 2025 was also at a recent high of 12.8%, nearing Covid numbers. In short, this means over 400,000 working age people who are unemployed or underemployed.
Tracy’s success in climbing out of bankruptcy during challenging economic times comes down to noticing opportunity. She found where business was growing fast (food delivery) and put herself in the path of that opportunity. The businesses she got involved with were clipping the tickets of growing trends.
In this high market, that got me thinking: what is the greatest toll-gate, ticket-clipping business we’ve not been looking at?
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