The decision that nearly cost me seventeen years.
I hold brands' hands. I hold their tech accountable. And I ask the hard questions before they become hard times.
A few years ago I made a single decision — based on advice from a trusted agency — that almost dismantled everything I'd spent seventeen years building.
After years on a platform I'd outgrown — or thought I had — I was sold a vision: enterprise-grade scale, future-proofing, infinite flexibility. The platform was prestigious. The agency was respected. The promise was that this was the upgrade my business deserved.
What I actually got was the slow, expensive strangling of a profitable business by infrastructure that was never built for a brand my size. Six-figure annual licenses for features I'd never use. A migration that took twice as long and cost three times the quote. Custom builds that broke with every platform update. Per-transaction fees that quietly compounded. An agency relationship that turned from partner to gatekeeper — every change, no matter how small, had to go through them. I couldn't move quickly in my own business anymore.
A profitable, multi-million-dollar business deteriorated into sustained losses. Personal capital, director loans and ultimately the family home were absorbed to keep the business operating. By December 2024, the home was gone. The business is still fighting.
By the time I understood the scale of the mistake, the exit cost was almost as devastating as the trap itself.
I'm sharing this candidly — on video, in writing, on every stage that will have me. Dotdigital, Yotpo, NORA, Online Retailer, eTail, Retail Doctor Group, Retail Oasis, Power Retail, Inside Retail, Retail Fest, ACU. In The Herald Sun, The Age, AFR, Forbes. Anywhere founders gather and listen — because if a 17-year-old Australian business has to close because of this kind of decision, I refuse to let it close quietly. Other founders are being sold the same upsell every week. The same prestige platform. The same agency promises. The same lock-in.
You should not have to lose your business to learn this lesson. So I'm teaching it instead. Every brand I advise now gets the questions I didn't know to ask — the ones that follow, below.