Boomerang Mode: Engaged

Ten thousand years before the Wright Brothers worked out powered flight, Aboriginal Australians were already carving pieces of wood into working airfoils, which if you’re skilled you can throw and watch come right back to where you’re standing.

When I moved to the US fifteen years ago, I didn’t know if I’d move back to Australia. Then I met my now-wife in San Francisco, and then we started a family together, and the odds of returning continued to lengthen.

But I've just taken off from San Francisco - for probably the 50th time - on my last round-trip flight back to Sydney. The next time I’m on this plane will be with the whole family on a one-way ticket, because we’ve decided to move back to Australia.

I've been in the US since 2011 - half of that time in San Francisco, the other half in Denver. For most of that time I was building Accelo, and after exiting, we were at a family and professional crossroads where moving back was a possibility.

The return became possible not just because my personal circumstance changed, but also because Australia has changed. When I left we had an emerging tech startup scene, and now 15 years later it has exploded. Heck, I’m on this plane now to come and speak at an incredible startup conference, Sunrise! And I couldn’t be more excited for this next chapter.

What's different

Fifteen years ago, Startmate was just getting off the ground. There was no Blackbird, no Square Peg, no AirTree, not to mention the plethora of early stage funds to nurture the tech startup talent Australia has always had. The result is the likes of Canva, SafetyCulture, Culture Amp, Linktree and many more startups really give shape to the Australian ecosystem.

The other thing that is different is the acceleration that AI provides to entrepreneurs. What we’ve built in just a few months with WorkSights AI would have taken a team 5x the size more than six times longer at my last startup. This acceleration, combined with the more practiced work and collaboration patterns from the pandemic, now makes it much more credible to build a big and impactful tech company from Australia.

What hasn't changed

While I’m yet to really rejoin the local Aussie tech community, my perceptions from mentoring at Startmate and working with hundreds of founders over the years tell me a few things haven’t changed.

The first is that Aussie entrepreneurs are incredibly ambitious and globally oriented. They’ve seen the successes of those that have come before them - Mike and Scott, now Melanie and Cliff - and they think “why can’t that be me?” While the broader Australian culture has issues with Tall Poppy Syndrome and an obsession that the nanny state “do something” to solve their problems, the community of tech entrepreneurs continue to punch above their weight in attitude and outcomes.

The second thing that hasn’t changed is the importance of networks and being in front of your customers, your partners, and being able to attract the best talent. This is what drew me to San Francisco 15 years ago, and if I were back at that age and life stage again, I’d 100% already be back in the Bay Area. But fortunately, having had the experience, I believe that I can make the best choices for our family, join a wonderful community and live in a beautiful place - while building WorkSights AI into an incredible company.

Why now

To be honest, this isn't "the perfect time for WorkSights AI." We’re still in beta and the market for my product is 5 hours behind me in the US. But, it's the right time for our family. Our kids are at an age where a move like this is doable without being disruptive - a few years older and it gets exponentially harder. What I'm grateful for is that between AI changing the company-building calculus, the US network staying alive, and an Australian ecosystem that's grown up enormously, the professional trade-offs you used to make to move a family home just aren't what they used to be.

Life is about trade offs, but this feels like an obvious one where there’s almost all upside. And I’ve still got those million United points to chew through in the years ahead.

Back into the community

While I’m excited to be sharing some experiences and advice from the stage at Sunrise this year, I’m even more thrilled to be reconnecting with a tech community that has come so far while I’ve been gone. I’ve been back for Sunrise a handful of times now, and it has always been bittersweet - positive to see the progress and the growth, combined with sadness to know I was only a tourist, a visitor, at something I was there for the genesis of back in the days of Silicon Beach Drinks in the shadow of the GFC.

But this year, I’m not a tourist - I’m a boomerang. While I’ve been contributing from afar the whole time I’ve been gone, being on the ground opens up a different kind of opportunity to contribute.

If you’re at Sunrise, come and see my talk at 3:40pm, or you can also find me on the Brella app.

And I've still got those million United points to chew through, so don't worry - I'll be back through SFO plenty. Boomerang mode: engaged.