Building a startup is hard. It takes a lot out of you. What’s been the hardest part?
For me, it’s people. Getting the right people in, moving the wrong people out quickly, and making sure you don’t hire too many. If you’re lucky enough to raise capital, suddenly there’s a bank account full of money and the temptation is to grow headcount. But headcount is the worst metric in the world. How big is your team, how small is your team, and how much can you get done? I scaled up too quickly, had to let people go, and then had to deal with the fallout from that. It just sucks.
We’ve all had those embarrassing startup moments. I remember going overseas to showcase our product and literally pulling it apart to get it to work. It just about held together. But there were so many near disasters. Just before demo day at Startmate, my daughter — who was meant to demonstrate the product on stage for the very first time — accidentally dropped it. Suddenly, it didn’t work. She was shaken, and she said, *“Mum, maybe I shouldn’t do it.”* That was worse for me, because the whole point was to show that anyone could wear it, even a child.
Because it was designed for kids, it was important that she be the one to show it off. I wanted to prove that it was fully functional, live, on stage. But in that moment, it could have been a complete disaster. You just have to trust your product will deliver. And even if it doesn’t, you need to be ready — ready to pivot, to empathise with the customer, and to show that their needs come first.
That product was novel, and in medtech there’s always the question: how early do you go for a patent? Do you spend the money and time protecting something that isn’t fully resolved yet? In our case, the first patent came directly out of the urgency of demo day. It was about to be seen by over a thousand investors, and we had to ask: do we protect it, or not?
In the end, we filed the night before. Tuesday night, demo day was Wednesday morning. Everything in life needs a deadline, and that was ours. Protect it before the world sees it.
Behind every startup success story lies a trail of embarrassing failures, crushing setbacks, and moments that nearly broke the founders.
In this raw conversation, our Melbourne entrepreneurs strip away the glossy exterior to reveal what building a company actually costs – emotionally, professionally, and personally.
Matt Allen’s biggest challenge wasn’t technical or financial – it was people. “It’s people,” he admits, “making sure you get the right people, that the wrong people are gone as quick as possible.” The worst metric, he learned, is headcount when you have money in the bank. Scaling too quickly led to painful layoffs and dealing with the fallout that “just sucks.”
Anushi’s story reveals how public failure can devastate founder confidence. At StartMate’s demo day, her daughter was meant to demonstrate their medical device on stage – but she dropped it moments before, and it completely stopped working. “This was the first time it was on public display,” Anushi recalls, and her daughter’s crushing words – “maybe I shouldn’t do it” – nearly shattered both their confidence.
These moments test everything founders believe about their mission, their product, and themselves.
The chapter explores how Bennett sold something Rosterfy “didn’t actually have” and worked backward to delivery, how patent decisions nearly derailed Anushi’s medical device company, and why the ability to “sell before you can actually deliver” is both a superpower and a dangerous tightrope walk that every early-stage founder must master.
Jeanette Cheah – Co-founder & CEO of HEX. A leading alternative education company. Left corporate banking after 14 years to build something meaningful.
Matt Allen – Co-founder of Tractor Ventures. Built Australia’s leading scale-up lending platform from scratch, despite having “the least entrepreneurial family on earth.”
Bennett Merriman – Co-founder & CEO of Rosterfy. Scaled from university side-project to managing 120,000+ volunteers for global events including the Super Bowl.
Kai Van Lieshout – Co-founder & CEO of Lyrebird Health. Engineer-turned-founder solving healthcare’s biggest inefficiencies through technology.
Dr. Anushi Rajapaksa – Founder & CEO of Misti. MedTech innovator. From hospital corridors to building life-changing medical devices, including taking her daughter on stage at demo day.
