We’re incredibly proud to have James Tynan join Square Peg's partnership. James has been active in the Australian startup ecosystem for years, and what better way to get to know James, than to ask some of the people that have worked with him! 

George Peppou, Founder and CEO of Vow (James’ first investment at Square Peg) and Jethro Cohen and Casey Flint from Square Peg’s Investment team, share their reflections below.

George, as a founder, what is it like working with James?

James was one of the earliest investors in Vow, he championed Square Peg leading our Seed round, and has been on our Board ever since. James has always been that rare balance of ruthlessly curious, constantly digging to know more about our business and deeply aware of our blind spots, steering me towards things that we just can’t miss. He’s (secretly) someone who loves operating and he loves to jump in to solving real problems that are happening in the company - this is something I really value and when it comes to bouncing ideas around on how we manage a hairy situation James has been amongst the top of my list. 

What makes James’ investment approach unique? 

GP: James builds conviction independently, rather than following trends, he looks at a company, a space, and forms an independent view on whether there is something there. He is more an operator than investor and often is itching to jump in and help solve problems. He doesn't sit at arms length, he is the first to jump in and help - it’s rare and special. James is right there, shoulder to shoulder helping fix whatever has gone wrong. 

Why should startup founders looking to raise capital talk to James?

GP: James is a rare breed, enough curiosity to form his own opinion, enough humility to know where and how he can help you and your company, and enough operating experience to jump in and help with pretty much any problem. I’m lucky to have spent the past few years working with James and you would be too. 

Jethro, what’s it like working with James, and what’s his approach? 

JC: James says ‘No’ a lot. When I first met him, I was almost confronted by it. He has a really really high bar on where he spends his time: the teams he wants to go deep with, the internal projects he decides to lead, or even the social events I drag him along to.

The more I work with James, the more I realise the magic of this approach. When he’s in, he’s all in. He never does anything by halves. When he gets excited by something, or sees the magic in a founder, there’s nothing that stops him from getting completely obsessed by the opportunity.

We’re really lucky to be on the receiving end of that energy. James takes our development incredibly seriously, and sees our decision making as an extension of his work in the ecosystem. I’ve learnt more in the last 20 months working with James and the other partners at Square Peg than in my career combined.

Casey, what have you learned working with James? 

CF: In venture, people say that we’re looking for unicorn businesses. James is a unicorn person. He has a remarkable combination of deep emotional intelligence and intellectual horsepower. You can’t just have one or the other in venture, because venture is as much about human relationships as it is about clear decision making.

James has this multiplier effect when working with him: his keen insights force you to level up your own thinking and think in new ways, and his deep understanding of people means he knows how to bring out the best in you.

James is more than an amazing colleague or partner to founders, he is a wonderful person with what seems like near-endless empathy, emotional intelligence, and thoughtfulness.

My second interview to join Square Peg was with James, and he was so warm, kind, and genuinely interested in who I was and what drove me as an individual. I can understand why founders love meeting him and working with him. He truly wants everyone - founders, his colleagues, and anyone he meets - to succeed and be the best version of themselves.

One of the many things I’ve learned from him is that that attribute alone - a deep and genuine desire to see others succeed - is a gift to those around you and unlocks people in the most wonderful way. 

Of course, we had to ask James to share some of his reflections too! 

What are you most excited about investing in over the next 12 months?

JT: We’re in the middle of (at least) three simultaneous crises and I think technology founders and venture capital have an important role to play in each.

The climate crisis has now become so acute that we need to build some of the world’s largest companies in record time. I’m inspired by the work of companies like Vow, Neara, Amber Electric and Zero Co in our portfolio - but when I look at the scale of the change needed, I know there are so many more incredible founders to back in this space.

Healthcare is also a system in crisis. We are failing to curb the growth of chronic diseases and reeling from shortages of talent and increasing costs. But we’re also seeing amazing new developments - including technology that can sequence a genome for hundreds of dollars, and AI that can now pass the US Medical Licensing Exam. I’m keen to find startups like our portfolio company Aidoc that can transform what our healthcare systems can do.

My first love is software and that’s also a sector in flux thanks to the transformative power of AI. We’ve been investing in AI businesses for some time. As a board member at Partly and Neara I’ve seen the potential of software and AI to transform trillion dollar industries. But the advent of large language models like ChatGPT is rapidly changing what software can do, how it is created and, perhaps, even what a startup looks like. It’s an exciting time to care about software.

What is something most people don’t know about you?

JT: I studied filmmaking at uni, made a bunch of student films, and to this day remain obsessed with the space where technology meets media. A career highlight was creating a partnership between Khan Academy and Pixar/Disney and getting to hang out under a massive sculpture of the Pixar Lamp at their offices in California.

Interested in hearing more? James dropped by The Sachin and Adam Show for a chat. You can listen to the podcast episode here.