Balancing the Grind with Casey Flint, Senior Associate at Square Peg

In our latest Balancing the Grind conversation, we’re featuring Casey Flint, Senior Associate at Square Peg. Casey, with her diverse background including a pivotal role at Uber, gives us an insider’s look into her daily life in venture capital.

She discusses the transition from operational roles to VC, where meetings with founders and researchers form a critical part of her day. Casey also touches on her personal interests like sailing and surfing, and how they provide perspective and balance in her high-paced professional environment.

Hi Casey, thanks for joining us! With such a diverse role at Square Peg and your past experience at Uber, could you give us a glimpse into how a typical day looks for you and how you manage to keep everything on track?

My pleasure! It was an interesting adjustment coming from an operator role to a VC role. When I was an operator I tried to avoid meetings – I saw them as a productivity waster and something that would take me out of flow. But as a VC they’re a critical part of the role (and meeting exciting founders feels very different to operational meetings!), so I keep the first half of my day open for meetings with founders, other VCs or interesting people I’m meeting in the themes I’m researching.

The rest of the day is spent doing a medley of things; searching for new founders to chat with, researching companies we’re currently looking at, tackling my inbox, checking in with my interns, doing pre-work and pre-thinking for either investment committee or upcoming founder conversations.

After I get through whatever’s on my task list and I’m back home I generally listen to podcasts while playing a low-effort video game, usually the Battle of Polytopia because I’m an AoEII fan (but that’s too stressful to play while listening to podcasts). I use a brilliant app called Snip’d that lets me snip whichever parts are interesting and compile those snippets into notes to share with the team or in my newsletter. 

Sailing seems like a fantastic escape. How does this passion influence your work-life balance, and do you find any parallels between sailing and your work in venture capital?

The learnings go both ways: I leverage my sailing learnings for VC and vice-versa. There are definitely parallels. From sailing, I’d say it illustrates the importance of clear communication. When you step on a sailing boat it can feel like everyone’s speaking a different language.

There’s a unique word for everything because people need to be precise with language to ensure that, in the heat of the moment, the right piece of information lands. It lands because everyone is speaking the same language and they know what refers to what (usually!). Effectively landing a message is something I think about a lot. 

From VC, something that astounds me about racing yachts is that there can be an implicit aversion to feedback. When something goes wrong, people can be reluctant to talk about why it went wrong. It varies from boat to boat, but for me, the concept of a post-mortem (which I first learnt at Uber) is SO important. I need to know what went wrong to improve. Who wants to make the same mistake over and over again?!

You’ve got a rich history working in different regions with Uber. How have these experiences shaped your approach to work, especially in a global firm like Square Peg?

I’ve had the good fortune of spending time working in countries like India, the Netherlands, Korea and Thailand to name a few. As a 19-year-old who joined Uber without a passport, it was pretty special to see the world that way. It gave me a huge number of learnings that I couldn’t cover in one short answer but some of them are:

  1. A deeper appreciation for how cultural differences can manifest in the way people work and the success of different businesses. It’s easy to let your own cultural biases get in the way if you haven’t taken the time to understand the cultural context of where you are working.
  2. The fact that product-market fit in one country or market never assures PMF in another, and that PMF is not a permanent milestone like people suggest – it’s organic and dynamic and needs to be assessed as such. You can lose PMF after you get it. 
  3. Nothing is as effective for team cohesion as face-to-face time together. I learnt this after working with product and engineering teams in SF – the relationship between those teams and ours would be so different after spending time with them in person, even after countless Zoom calls. 

Your interest in platform businesses and the gig and creator economy is fascinating. How do you stay updated in these rapidly evolving spaces while handling your responsibilities at Square Peg?

The short answer is that I consume a lot of content in my own time, simply because that’s what I enjoy doing anyway. 

One of the reasons curiosity is said to be such an important quality to have as a VC is that it’s quite difficult to get by without it. If you didn’t have the curiosity to drive the extensive reading and content consumption this job demands you’d struggle.

Whether you’re a generalist (no specialisation) or thematic (specialised) investor, you need to do a whole lot of self-led learning and reading. I still love reading about network effects and platform businesses – and Square Peg has had great success investing in that model – and the creator economy, but I’ve also spent a bunch of time looking at products that sell to developers and the data & ML spaces given my roles at Uber were data-heavy. I find the best return on time there is simply speaking to great developers, researchers and ML engineers. 

Writing on LinkedIn about various topics must be quite fulfilling. How do you balance this intellectual pursuit with your day job, and what motivates you to keep writing?

To me, they are intimately connected in more ways than one. It’s really important for VCs to be able to articulate and subsequently communicate their opinions and ideas. It not only helps you give better feedback and support to founders (because you can communicate better), but it also helps your team understand your rationale and it helps you structure your own thoughts.  

In programming, there’s this concept called “Rubber Duck Programming”. The idea is that you sit a rubber duck on your desk and, when you have a difficult problem you can’t solve, you explain the problem to the duck. It might seem like a laughable idea to some but the mere act of articulating your thoughts can bring a deep amount of clarity. For me, LinkedIn and my blog Artificially Intelligent act as an extraordinarily useful way to talk through my own thoughts and organise them. 

I also dislike the information asymmetry between VCs and founders. Founders are often new at this. VCs are not. By sharing what I see and experience in my capacity as a VC on LinkedIn, I can help break down some of those information barriers. 

The above are extrinsic motivators to keep writing, but the truth is that I just enjoy writing and often just feel compelled to do it. That’s why I keep writing!

And lastly, what’s your advice for someone looking to balance their professional ambitions with personal passions, especially in high-paced environments like venture capital or tech startups?

I haven’t nailed this and I think it’s something everyone has to tackle individually. One thing that’s underrated is seeing a psychologist. You don’t need to see a psychologist only when you’re feeling mentally unwell.

Psychologists can help you navigate the stress of intense jobs, can help you develop professionally by helping you unpick your own psyche, and establishing an early relationship with a psych can ensure someone’s there when you need them most. 

I’d also suggest finding something that gives you perspective. For me, that’s my family, sailing, surfing and friends. When it feels like everything is too much – and I’m giving myself a hard time for getting something wrong or whatever – I think about my family or what it feels like to be in the surf and it helps me remember that my issues today are trivial in the scheme of things.

About Author

Hey there! I'm Hao, the Editor-in-Chief at Balance the Grind. We’re on a mission to showcase healthy work-life balance through interesting stories from people all over the world, in different careers and lifestyles.