Why I'm Joining the Vinnies CEO Sleepout: A Personal Reflection on Homelessness

I spoke about this on Our B2B SaaS Journey episode 13: Starting a SaaS? Start a podcast from 26:45 onwards.

On the 19th of June, I’ll be taking part in the Vinnies CEO Sleepout on the Gold Coast. It’s something I’ve always wanted to do, but for a long time I wasn’t in the position to. Now I am.

This isn’t just a token gesture for me. It’s personal.

When I was a kid, my family had a pretty rough time. We moved from Western Sydney to the United States when I was around eight. Not long after we got there, things took a turn. We overstayed our visa, which meant we became what you’d call "illegal aliens." I was just a kid at the time, so I didn’t really understand everything that was going on. But I do remember we didn’t have a place to live.

For a while - maybe three to six months - we were homeless. We slept in a truck trailer behind a bar. It was cold. It was scary. It wasn’t safe.

Eventually, we made it back to Australia and ended up living in housing commission around Campbelltown. My mum used that time to get us back on our feet. I’ve always respected that. She never let our situation define her, and that stuck with me. She saw it as temporary - just a station, not the destination.

Now, years later, I’ve built a career, a business, a life. But I haven’t forgotten what that time felt like, or how close to the edge things were. I don’t think about it every day, but it’s part of who I am.

So when the opportunity came up to take part in the CEO Sleepout, I said yes. Because while my story had a way forward, not everyone gets that. Homelessness isn’t just a statistic. It’s real people. And sometimes, all it takes is a few things going wrong for someone to end up without a home.

This is just one night for me. But for thousands of Australians, sleeping rough is every night. I’m doing this to raise money for the services that help people when they need it most - emergency accommodation, food, healthcare, and support to get back on track.

As a business, SixSides has donated $530 to support the cause. If you’re in a position to donate too, I’d be grateful.

You can help end homelessness here: ceosleepout.org.au

Thanks for reading.

— Gavin