Full Video Transcript

So let’s set the stage by really thinking about that founding moment. Why did you go into startups and entrepreneurship in the first place? Why did you take that bold leap?

That is an excellent question. That my parents were probably wondering at the same time. I was working a corporate job. I think I did that for about 14 years working at banking energy, that kind of stuff. And I just, I don’t know if you have this, if you can relate to this, but I had that nagging feeling that, A, I wasn’t living up to my potential, B, if I didn’t try to do something, I would regret it in a few years. And then honestly, just a really deep sense of curiosity, like, what else is beyond these four walls?

Because I just grew up doing a very linear kind of go to school, go to uni, get the corporate job, be the good girl, and then just kind of was like, there’s gotta be something else and I gotta try it now, otherwise it’ll be too late.

I think it was something that I’d always wanted to do, and I think I was gonna keep trying to do it until I found something that people loved and stuck as well. And I think for me, Lyrebird was a really perfect mix of my personal experience, what I love, what I’m deeply passionate about, and then the ability to build something that makes other people’s lives better as well. So I don’t know if it was an active choice so much as it kind of happened.

He’s a born entrepreneur.

Well, you know, it’s an interesting thing. Are entrepreneurs born or made? We hear this quite a lot. What do you think? You deal with a lot of founders.

I deal with a lot of founders and I certainly came from the least entrepreneurial family on earth and my dad had one job for his whole career. So when I started Tractor, it was definitely to solve a problem. I think that’s the thing for me was that we saw that there was a real gap in the funding need and as much as people think Tractor Ventures is a fund, it’s actually a startup.

So it sounds like it wasn’t, oh, let me go and just find a startup and come up with an idea, but actually here’s a problem I want to solve and then all of a sudden you’re running a startup. That was a bit similar to you, wasn’t it?

It was, yeah, very similar. So Rosterfy, the tech company as it is today, was born out of an event staffing business which is all shaped around helping motivated uni students find casual event work while they study. And it was a problem. Myself and my cousin, we both studied the same course. Two years apart, we faced at university where thousands of graduates are coming through. However, there’s not as many jobs in sport and events. So whilst every position description requires 2 to 3 years experience, how do graduates get that experience? And so it was really driven through some challenges initially, but then also just a problem that we saw everywhere that people could relate to very quickly that then generated the idea—it wasn’t the other way around, so to speak. So that was the genesis.

And then the bigger the problem, the more passion you have for it, the more motivated you are to see it through. So that motivation then carried the early years to then getting early attraction as well.

It wasn’t something that I went looking for. I actually didn’t know what the word startup really meant, but I realised that my role in the clinical environment didn’t allow me to actually commercialise a product to actually help the patients that I saw day in and day out and I was getting frustrated that I actually need to bring this out and I actually had to go outside of that environment that I was in and actually, you know, not to completely leave, but actually work with that environment to actually build this for that relevance.

So I was looking for an available doctor that I had to see and that was a difficult process, more so than I thought it would be. And then when I spoke to my doctor and we’ve got a really good relationship, he mentioned how much time I was just wasting on paperwork, and I was like, man, this is not something that you need to study 10 years to do, right? Like, virtually none of this. I think then it’s almost like looking back, it was like, as a patient, I valued my doctor’s time probably more than he did a bit. And that was the need and that was the problem. That kind of like, it was born out of just trying to solve that problem for him. It turned out he was not alone.

Something I didn’t expect was that your job description changes, like, every three to six months, depending on how well you’re going. If you’re going well, you’ll change even quicker. And no one tells you when that happens, what it should be next. And it’s kind of new to figure out, like, notice, look around when you kind of need to change it and then figure out what that new one is all the time. And that’s crazy.

What do you think serves you best as a founder? Like naivety, curiosity, or confidence?

I call it naive optimism. I often think of it as that because every setback is not really a setback, but you know that there’s gotta be a better way. So you really optimistic and positive about it, and eventually that optimism will influence people enough to be like, yeah, we’re onto something.

Key Takeaways

  • The “nagging feeling” that sparks entrepreneurial action
  • Why curiosity drives founders beyond corporate “four walls”
  • Problem-solving vs. opportunity-seeking in startup creation
  • How personal frustration fuels business innovation
  • The importance of naive optimism in early stages

The Founder’s Psychology Revealed

Every founder has a moment when they realise they need to step outside their comfort zone. This chapter explores the psychological triggers that transform employees into entrepreneurs, revealing common patterns of dissatisfaction, curiosity, and the fear of future regret.

Jeanette’s story exemplifies this journey – after 14 years in corporate banking, she experienced the “nagging feeling” that many founders describe.

Matt Allen’s background challenges the “born entrepreneur” narrative entirely, coming from “the least entrepreneurial family on earth” where his journey was driven by problem identification rather than inherent business instincts.

Bennett’s experience with Rosterfy demonstrates how personal frustration becomes entrepreneurial fuel, facing the classic catch-22 of needing experience to get experience in sports and events.

These stories reveal that successful entrepreneurs aren’t born with special DNA – they’re made through curiosity, systematic problem-solving, and the courage to act on persistent feelings that there’s something better beyond the safety of traditional employment.

I had that nagging feeling that, A, I wasn’t living up to my potential, B, if I didn’t try to do something, I would regret it in a few years.

— Jeanette Cheah, Founder, HEX

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Featured Founders

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.