Charlie Gearside: Leaving $560M Startup To Reshape Australia's Future

Eucalyptus founder leaves to ask what Australia builds next

Charlie Gearside built Eucalyptus into a $560m telehealth company and then left. The episode is his read on Australia. He argues prosperity peaked around the Sydney Olympics and the last 30 years were spent juicing property and minerals, leaving young Australians priced out and startups short of capital and people. He says he was no longer needed at Eucalyptus, which freed him to ask what Australia builds next, from software into deep tech.

Takeaways

• He left Eucalyptus once he was not needed. Charlie Gearside built the telehealth company with three friends and left in late 2024. Therapy and introspection convinced him the team suited its current stage, and he calls CEO Tim a generational leader who did not need him.
• There is no balance, founders must burn. He says you have to burn yourself as a founder and that balance is not really a thing. Four months after leaving, he felt noticeably sharper at his first board meeting, calling the fog a low-grade flu.
• Australia peaked and has been juicing assets since. He dates the peak to around the Sydney Olympics. The last 30 years were about selling houses to each other and extracting resources, and he adds Canva and Jira to the usual list of Australian invention, the Hills Hoist and the cochlear implant.
• Startup equity is a wealth path few understand. Owning parts of companies through employee equity works, he says, and the average person has no idea. Young Australians face hard housing costs and weak wage growth and are told by spruikers that investment property is the way to get rich.
• Better news cannot beat bad journalism. Australian business coverage tears down rather than builds, blowing smoke up the big end of town while treating startups with disdain, he says. He and co-founder Alexei dropped an AI news platform idea because bad journalism appeals to the lizard brain.
• The brain drain bites when companies domicile abroad. Australians have long moved to London and now increasingly New York, and he struggles to say whether that is a real drain. The damage is when companies domicile in the US and capital stops flowing back to Australian jobs.
• Trust your people earlier and stop micromanaging. His advice to the hosts is to give people the tools, set the vision and step back. His worst moments at Eucalyptus came when he micromanaged, and he learned to hand off work by learning every skill himself first.

Eucalyptus's near-death moments

• A month in, Stripe took Eucalyptus off its platform. The company was among the first to legitimately charge for prescription medication, and Nikki at Blackbird used his contacts to get them back on.