She Sold Her AI Company at 2PM. By 7PM She Was Drinking Ayahuasca.

At 2pm, Dr Catriona Wallace closed her laptop, still in the business suit she'd worn to sign the paperwork on a video call. She had just sold the tech company she'd spent seven years building. By 7pm, dressed for a very different afternoon, she was drinking her first cup of ayahuasca.

She hadn't planned the timing. It just happened to land on the same day.

The Rocks, Kings Cross, and the shadow side of humanity

Wallace didn't set out to build an AI company, or even to go into business. She trained for agricultural economics at university, intending to farm, until she noticed her classmates were all quietly becoming investment bankers instead. She dropped out. Partly, she says, as rebellion against a conservative middle-class upbringing, she joined the New South Wales Police Force at nineteen and spent three or four years working The Rocks, Kings Cross and Darlinghurst during Sydney's most notoriously corrupt policing era.

"It was my first walk in the shadow side of humanity. I learned a lot about organisational systems that create poor behaviour, that create corruption, that create criminal behaviour — not from the criminals, but from the police themselves."

She left policing for a PhD in organisational behaviour, writing a thesis — mocked at the time as absurd — on technology as a substitute for human leadership. Years later, UNSW awarded her a second, honorary doctorate for her international work on AI ethics.

Building an AI company before the tools to build one existed

In 2013, combining that research with eight years running market-research firms, Wallace founded Flamingo AI: one of the world's first enterprise virtual-assistant companies, built entirely from scratch because no off-the-shelf language models existed yet to build on top of. The company patented its own machine-learning approach. Because its clients were Fortune 200 American companies, Wallace relocated the business to New York — flying two weeks there, two weeks back to Sydney and her five children, for four years.

In 2016 she listed Flamingo on the ASX with chair Kathy Reid — by her own account, only the second time in the exchange's history a woman CEO and a woman chair had taken a company public together.

"I had investors tell me they'd give the company a million dollars if I took my nose ring out. Investors rang my board to complain that my hair wasn't brushed. People told me: you've got five children, how can you be a mother and run a tech company? Choose one."

She found the reception in the United States starkly different — American clients and investors treated a female founder-CEO as unremarkable. In Australia, she says, she didn't find the same.

Then two trillion-dollar companies gave her product away for free

Being publicly listed meant every material setback had to be announced to the market, and the market punished her for it in real time. Then Amazon and Google released free versions of essentially the same enterprise chatbot product Flamingo sold, commoditising it overnight; the company scrambled to pivot from a customer-facing tool to an internal one. When COVID hit in early 2020, Wallace was grounded in Australia, unable to reach her fifty-person US sales team as American clients froze every project at once. The share price collapsed. What followed was an eighteen-month process of trying to sell the business out of its own listed shell — a stretch she got through, she says, by reading Ben Horowitz's The Hard Thing About Hard Things: "You think that's hard? Wait, it gets harder. Did you know hard had a dungeon? And through the dungeon is a trapdoor, and through the trapdoor is the bowels of hardness."

What the medicine showed her

Her first ayahuasca ceremony, that same exit-day evening, was brutal. Seven hours of purging surfaced what she calls her shadow behaviours in plain terms: an identity built on reputation, a disconnection from her own children, small dishonesties she'd absorbed as normal in business. At one point the ceremony returned her, unbidden, to a memory she says she hadn't consciously thought about in fifty years — a childhood friend named Adam, killed playing on railway tracks as a boy. She sobbed for hours.

She has since trained for two and a half years as what she calls a medicine woman — not a shaman, she's careful to specify — including work with 5-MeO-DMT, and founded Ethical AI Advisory, coaching businesses and governments on responsible AI. She still calls AI the largest existential risk humanity faces, citing researchers who put the odds of it contributing to civilisational catastrophe this century as high as one in ten. She wrote a book, Rapid Transformation, arguing that leaders no longer have the luxury of a fifteen-year mentoring arc to become self-aware — not with AI, climate change, mental health and geopolitical instability all compounding on the same short timeline she just lived through herself.