Got Laid Off Friday, Had a Bartending Job Monday

I got laid off on a Friday. By Monday I had a bartending job.

I was 20, working as an IT sysadmin at Educom in Sydney. Youngest CCNA in Australia. Thought I had a career path.

Then I didn’t.

Here’s what I did. I got my bartending certificate the following week. Printed 100 resumes. Walked down George Street on Monday handing them out to every bar and restaurant I passed. Had a job the same day.

Starbar as a glassman (busboy). Washing glasses and cleaning ashtrays for people who still had office jobs.

That doesn’t sound like a career move. It wasn’t. It was a survival reflex. The gap between “I lost my job” and “I have a new one” was measured in days, not months. I didn’t sit down and make a plan. I just moved.

A few years later, I read The 4-Hour Workweek. And something broke in my brain. Not the “work from a beach” fantasy that most people take from that book. The idea that you could build something from anywhere. That geography was a choice, not a constraint.

Every excuse I had for staying in Sydney disappeared in one chapter.

In December 2009 I packed my entire life into grey Coles garbage bags. My mum told me to put mothballs in everything because my stuff would be packed away for a long time. She was right.

I drove to Bendigo with my brother. Flew out of Melbourne. One-way ticket. No return planned. No job lined up. No savings worth mentioning.

My income went from $150K in corporate to $30K in year one. Then $50K in year two. I built SEO sites, e-commerce stores, lead gen businesses, anything that could run from a laptop. I lived in Hong Kong, Panama, Mexico, Barcelona, Singapore, and eventually San Francisco.

Twelve years of that. Twelve years of building small things, failing at a few big things, learning what actually works when there’s no safety net and no boss and no one checking if you showed up.

Then I built Process Street. A real company. Venture-backed. Accel, Salesforce Ventures, Atlassian. The kind of company that 20-year-old me in Sydney could not have imagined.

But here’s the thing. The muscle I use every day as CEO is the same muscle I built walking down George Street with 100 resumes.

The speed between “something broke” and “here’s what I’m doing about it” is still measured in days, not months. A customer churns, I have a save play running by lunch. A team member leaves, the role is restructured by end of week. A market shifts, we’re already building the new thing.

That’s not strategy. That’s a reflex. And I learned it bartending.

The same bias toward fast response shows up in how I build now, including the AI systems that turn messy work into operational leverage.

The lesson I’d give my 20-year-old self: the thing that feels like a setback is actually training. The speed you develop when you have no choice becomes your superpower when you have every choice.

Twenty-one years later, I still pack light and move fast. The garbage bags are gone but the instinct isn’t.