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Four Months to Mortgage Free: The Cherry Family's Reset

Four Months to Mortgage Free: The Cherry Family's Reset

October 10, 2025

Most financial turnarounds start with a spreadsheet. This one started with a teenager.

David and Jackie Cherry's 16-year-old son, Oscar, was struggling after losing a close friend to suicide. Hoping to lift him out of it, David took him to Melbourne to hear motivational speaker David Goggins — but the story that landed wasn't Goggins'. It was Infinity Group founder Graeme Holm's: a C-grade student who built a company. Jackie says she watched a spark switch on in her son that night and never go out.

The reality check

That night led the Cherry's to Infinity's two-day Masterclass, and from there to a forensic review of their own finances. It wasn't comfortable reading. By David's own admission, they had no retirement plan, no financial literacy to pass on, and a default setting of spending whatever was within reach.

So they stripped it back. They worked more, cut hard, and — in Jackie's phrase — sold everything that wasn't bolted down: the investment property, the new car, the pandemic-era accumulations.

The result

Four months later, the mortgage was gone. The family home, hand built by David, was theirs outright.

From there they rebuilt: four investment properties, a self-managed super fund, and a savings buffer that now sits at $40,000–$50,000. Their strategist, Benjamin Fenley, is blunt that there's no shortcut — Infinity doesn't control the money, he says, it keeps clients accountable.

It hasn't been painless. The budget is tight, the hours are long, and they've fielded scepticism from people close to them who assumed they'd joined a pyramid scheme.

The part they're proudest of

Oscar is now a third-year apprentice carpenter, coaching soccer on the side, and has saved $100,000. Jackie calls it a beautiful ending to what could have been a very sad story.

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