Association Series #9: Casey Flint, Senior Associate @ Square Peg
Uncovering how interesting minds entered Venture Capital and new aspects of their personality, experiences and processes to light.
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#9: Casey Flint, Senior Associate @ Square Peg
1/7 Career overview before joining Square Peg
Early Entrepreneurial Exposure
I grew up in an extremely small rural town in Queensland. I think the population sits at around 700-800 people. It's a cattle farming town. My parents are extremely entrepreneurial at heart. They've always been serial entrepreneurs. I used to come home from school and they'd have another idea and they'd want me to help mock up a logo or, you know, say, 'What do you think of this?' or 'We're going to sell this.' They're two of the hardest-working people I know. I've grown up against that backdrop of people founding businesses and understanding what that roller coaster ride looks like.
Higher Education and Early Career Decisions
I saw University as a bastion of answers. I thought that that's where I could go to get answers to all of my curiosities. So, when I was 19, I went to study Biochemistry and Molecular Biology at the University of Queensland. My plan was to study Science, go into academia for a bit, and then become a founder myself in the health space.
But, I ended up getting a bit derailed by Uber about eight months into my first year of my degree. I met some Uber folks, they had moved into the River City Labs co-working space in Brisbane, and I just fell in love with that team and the business and basically begged them to let me be an intern, which about three months later, they said yes.
Involvement in Uber’s Strategy Team
I spent about a year and a half interning with Uber, doing everything from onboarding drivers to moonlighting as Uber's graphic designer to writing EDMs to drivers.
Eventually, I decided to go full time with them. I got a role in the Driver Growth team in Brisbane. That was kind of a combination of growth and offline marketing for drivers and also quite a heavy analytics role.
I was doing a lot of reporting, a lot of analytics on how to improve conversion for drivers, and really developed a strong interest in data science. Then, Uber was founding a strategy team in Sydney. I didn't think it'd be a very good fit for that, even though people were suggesting that I apply. Eventually, after a few people suggested, I think some of the leadership team in Sydney kind of nudged my boss at the time and said, 'Hey, we were really hoping Casey would sign up for this strategy role. We think she'd be great.' So, I became the first official member of that team working on competitive strategy.
Working Overseas and Pivoting towards Startups
I ended up working in Amsterdam for a bit, working on a very cool project for the person who's now CEO of Uber Eats.
I came back to Australia, told my boss I wanted to go back into startups, and he suggested that I move to Hong Kong or Japan. I ended up working on a joint venture for the Korean business for eight months, which was a really unique experience and really fun.
I joined Square Peg shortly after that.
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Learn about his strong cultural values growing up, behind the scenes of building the success story that is Seek, Transition to Square Peg Capital, what he wants to learn in the next 6 months, most painful learning and more.
2/7 What was the interview process to join Square Peg?
I had several friends who had moved on to Square Peg portfolio companies, and three or four of them had said, 'You should talk to Square Peg, they're hiring. I think it'd be really interesting. You'd suit it.' And I kept saying, 'That's ridiculous. I am not an investment banker. I'm not a consultant. Why would I apply to that role?' After the fourth person mentioned it, I was like, fine. I'll speak to them.
So I contacted the recruiter, had a phone call with her, and she basically said, 'No, actually, your profile is pretty perfect. They're really looking for people with operator experience, who've been part of high-growth startups.' It's not widely known, but Square Peg actually invested in Uber. So, they really understood the business well and knew that Uber tended to hire great talent.
Conversations with Square Peg Leadership
Then, I had a second conversation with Tony Holt, founding partner of Square Peg. It was meant to run about an hour but ended up being a bit over an hour and a half. I enjoyed it so much because, unlike other interviews I've had before, this one was oriented around who I was, what motivated me, and what I love about tech. We actually spoke about virtual reality at length because I'm really into gaming and virtual reality. That was super fun. I was starting to think, 'Okay, this could be interesting. I really like technology. These people seem interesting. Their investments are cool. And I would get to see so many different kinds of businesses.'
So, the next step was to meet James Tynan and Lorena. James Tynan is now a Partner in the Square Peg fund, and Lorena runs HR for us. It was a very similar interview to the first one: again very oriented around who I was, what motivated me, and what I liked about tech.
Then I had another conversation with Paul Bassat, another founding partner of Square Peg. Again, it was super similar, really oriented around who I was. There weren't any 'gotcha' questions. They weren't trying to put me on the spot for anything. Paul asked a few consulting-style questions about market sizing and how to break down quick problems, but it was very oriented around what I'm passionate and curious about.
The Case Study Challenge
Lastly, the more analytical part of the process was the case study.
Basically, they said, 'Hey, here's a business and a deck that we previously looked at. We want you to write up an investment case, whether that's we should continue looking at this business or we should not continue looking at this business.'
I think the fact that I enjoyed that process so much was a good signal for me that I would also enjoy the role, especially given how much I'd fallen in love with the team and the warmth and kindness they showed me.
Post-Case Study Discussions
Once I'd done the case study, which I think had to be done over a 24-hour period, I spoke to James and Tony again, just to explain my reasoning and talk through why I'd structured it in the way I had, and what metrics and tidbits I thought were interesting about the business.
3/7 Looking back on the past 12 months of being an investor, what two skills have you found most valuable?
Managing Personal Health and Productivity
So the first one I’ll mentioned is not necessarily venture-specific. So it might be slightly less useful for some people, but I think it's really important nonetheless. That's honestly just managing myself.
This has been a focus over the last 12 months, but truly, it's been a focus for the last 10 years. I have had generalised anxiety since I was six and some issues with depression since I was in my teens.
So, managing myself is a big part of my day-to-day. It can get a bit arduous sometimes, but it's just so important. This feels especially important in a role like VC where you could take it in so many different directions.
I think being a venture capitalist comes in many, many forms. That means you might spend some hours of the day working on a community event, you might spend others talking to founders, and then you might also be thinking about portfolio management or reserves, whatever it might be. So, ensuring that you're productive and spending your time well is super important.
Improving Decision Making and Assessments
The second area is just making sure that my decision-making and assessments of people and businesses are as robust as they can be.
This really means challenging my opinions and biases as much as possible. It's partly for becoming a better investor myself and doing well by my team and our limited partners. But it's also for providing good feedback to founders.
The more robust your thinking is, the better feedback you can provide. I think when VCs don't give very good feedback to founders, it can be indicative of the fact that they just haven't really challenged themselves to ensure that they're making a robust decision.
So when I notice that my feedback is a little light, I realise that maybe I actually need to be a bit more thoughtful here and take a bit more time. But this is something that always needs improvement. It's something investors spend their entire career working on, right? Making better investment decisions.
I hope to spend the next 12 months focusing on that, or even the next 12 years, improving that.
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4/7 Three specific things you do directly after meeting a founder for the first time?
Meeting with Founders as a Team
Sometimes I'm meeting a founder with other people in the team, and sometimes I'm meeting them by myself. That changes the process a little bit. When I'm meeting founders with other people in the team, we generally reserve 15 to 30 minutes afterwards to discuss our thoughts and next steps.
Meeting with Founders Individually
If I'm just meeting those founders by myself, I will take a bit of time to reflect on two things: one, what I thought of the business and the founder or founders; and two, how I felt about how I ran the meeting and whether my questions were really getting to the heart of what needed to be addressed.
Reflection and Planning
Next, I will tidy up my notes and reflect on what I think the next step should be. This could involve either going back to the founder with a response like, 'I don't think it's the right fit for Square Peg', or initiating a more extensive process if I am excited about moving things forward.
Communication with the Team
Lastly, if I am enthusiastic about the prospect, I'll quickly relay my thoughts back to the team because I get pretty excited quickly. If I think they're exceptional founders, I want everyone to meet them as soon as possible. So, I will start considering the best people to involve in the next meeting and begin organising that in their calendars so we can move swiftly.
5/7 What is your top tip for getting into VC?
Reflecting on Venture Capital as a Career Choice
This is answering the question somewhat indirectly, but first, I would recommend that you think about why you want to get into venture capital. It's often perceived as a glamorous and prestigious field, and while it does carry prestige, it also involves a lot of saying 'no' to people. It requires deep empathy and a comfort level with making decisions amidst considerable ambiguity. Some people may struggle with this state of flux. So, it's essential to question why you're interested in venture capital in the first place. If you're genuinely curious, passionate about technology, and empathetic towards the founder journey, these are traits that could make you a great fit.
Building Relationships in Venture Capital
As for breaking into venture capital, as others in this series have mentioned, the key is relationships. Venture capital is fundamentally a people business. The more you can demonstrate that you're connected with the top founders in Australia, the more attractive you'll be to potential teams. This is because the ability to attract and support high-potential founders is essentially the most crucial currency of venture capital.
Demonstrating Capability for the Role
Besides relationships, it's about showing that you're capable of the role. This could involve building relationships, writing your own investment theses and starting a blog, or getting involved in the community. These are just some ways to demonstrate your capability and passion for the field.
6/7 What separates the best investors from the rest?
The Importance of Raw Intellectual Power and Empathy
As frustrating as it may be, because I believe it's an innate thing, I do think that raw intellectual power and empathy are two of the most important attributes.
Actually, I really struggled when I initially joined Square Peg because there's such an intense concentration of these rare attributes in this group of people. You meet the team, they're incredibly warm and kind, so I didn't feel intimidated in that respect.
However, you can also quickly see their intelligence and how high their EQ is. This made it incredibly challenging for me to feel like, 'Oh, I genuinely belong here, and I deserve to be here,' when surrounded by these types of individuals. And so, I think that is a really significant factor that sets people apart.
The Value of Consistency
I would also like to reflect on a comment Paul Bassat made on this topic. I don't want to misrepresent it, but he was talking about exceeding average, essentially saying that it's not particularly difficult to be better than the rest. It's more about consistency and consistently being slightly better than everyone else.
Simple Steps to Stand Out in Venture Capital
I believe the way you can accomplish this in venture is by focusing on a lot of very simple things.
It's a disappointing reflection of the state of investors that these simple things, like being quick with responses, being thorough with feedback, and being honest with people, can be the hurdles.
Unfortunately, we hear from founders all too often that these aren't the kinds of behaviours they're encountering from investors. So, yes, I think what also sets people apart is just consistently doing the right things by founders.
7/7 What spaces are you currently interested in?
The Need for Technical Curiosity in Australian VCs
Something that I've realised being in VC in Australia is that we probably don't have as many VCs that are as technical as what you see in, for example, Israel or the US. I feel like there's not as much curiosity around what sits under the technology. There's a lot of curiosity around what makes businesses succeed, but not so much the technical side of things.
That's something that I'm hoping to develop as a VC who's taught themselves to code and is really interested in data science.
Involvement in AI Investment and Understanding Hype
This has naturally extended into this wave of excitement around artificial intelligence. I'm lucky that Square Peg has actually done a decent amount of investing in AI over the last 10 years. We first made an investment in an AI-powered business in 2013. About 20% of our portfolio is AI native.
My boss, Dan Krasnostein, made a really great investment in a company called Aidoc, which is a computer vision healthcare business. As a result, he asked me a couple of years ago to start looking at AI businesses in Australia and so that's been really fun, just like this recent wave of LLMs.
I know that there's been a lot of commentary on how hype-driven investors are, but I think there's a lot to be said about how this could be a really powerful driving force for good, and I do think that it goes well beyond hype.
Suddenly everyone wants to leverage this technology and they're being technology-first rather than problem first. At Square Peg, we're really oriented around still focusing on real problems and great solutions, and AI is just a part of that. But that's been a really fun part of the last two years at Square Peg.
Thanks for reading this instalment of the Association Series! Get in touch with us anytime here — to share your thoughts, suggest other questions and/or people we should feature.
Fly high,
Vidit, Alfie and the Curiosity Center team