How did your career start at Merrill Lynch and Citigroup, two immense multinational investment corporations, influence your later career in start-ups?
There are two elements to this. I did a history degree at university and then my graduate job was selling equity derivatives at a trading floor, so it was extremely different from my underlying degree. The big thing I learnt was that if you put in enough hard work you can learn pretty much anything and you don’t need to feel constrained by what you did at university.
The other thing I learnt was that I didn’t want to be a small cog in a big machine and I didn’t want to work in a company where I couldn’t see the impact of my work and its outcomes.
Why did you make the move to VC and what do you love most about the job?
So when I went to a start-up, I absolutely loved it. It was really the energy that comes in a growing sector rather than a shrinking one. It’s an industry where there’s hope and there’s excitement and there’s energy and people are working about things they were passionate about, and that’s really exciting. Now what I miss about start-ups was the breadth of topics you get to cover when you’re in a generalist investment role. Also just the practice of investing, which I really enjoyed.
VC is a brilliant hybrid of two things I’ve done before.
It’s a job that’s designed for curious people. You’re learning about new sectors every day and new technology and new business models. It’s what I would do in my free time. So the idea that I get to do it as a job is pretty amazing.
Were any of your career moves foreseeable?
No, I didn’t even know what VC was until a year before I started doing the job. It wasn’t on my radar. It was really just an iterative process of moving towards things I enjoy.
How did you crystallise these interests?
It wasn’t one particular moment. When my partner and I decided to move countries, it was a clean slate moment. Neither of us were moving for a particular job, and so we were reassessing what we would most enjoy working on. I had an inkling that I might really enjoy VC. There was no downside to trying it out.
Is there a difference in Australian start-up culture compared to other places you’ve worked?
Not really. The industry globally is moving very fast, and the Australian startup ecosystem started ate but is catching up quickly.
What are the early signs of a promising business that other VCs might overlook?
I think that at the very earliest stages, the most important things are the team and market.
The team: do you have great experience in the sector? Do you have a unique understanding of the problem that you’re trying to solve? Are you trying to solve it in a new and interesting way? That could be because you’re deep in the sector so you see how the market is moving before other people do or you have an outside range of experiences that you’re bringing to a new sector that help you see it in a new way. We’re looking for the ‘why you’ and the ‘why now’.
What we look for that other VCs might not: I don’t think there are specifics. At the early stages, something that might be counterintuitive is that sometimes it doesn’t have to be the first product. If you have a brilliant team and a fast-growing market, if the original product doesn’t hit exactly right, they can pivot and can find the right fit in the market.
Examples of a good team?
There are a number of factors. Resilience and drive are huge, experience in sector, a combination of complementary skills in the founding team are good.
We look for tech, product and growth. Do you have experience across all three areas in the founding team?
In terms of specific examples, Canva is a good example of product, tech and growth. Cam is tech, Mel is product, and Cliff is growth. Having those complementary skills has been really valuable for them.
You’ve written about the ‘unfair advantage’, where a business capitalises on their advantages to move from being a good business to a great business. For smaller companies struggling to scale or develop brand loyalty, how can they best develop such an advantage?
So I think it’s different for each business.
The most applicable [advantage] across a range of companies is really trying to build in referral into your customer journey. Mobilising your early fans, most loyal customers and enabling them to be your engine for growth.
Should there be different approaches to different customer segments?
Your existing customers should be the ones to bring in new customers. The best marketing is your best friend telling you something is great – that’s the most trusted recommendation.
A perennial example of product-led referral is sending an email with Hotmail and adding ‘ sent with Hotmail’ to the end of the email. Or you seek to enable your community – Glossier in the US uses its community to help spread the word enabling their customers to become advocates for new customers.
On top of a hectic schedule at Airtree, you run a website, newsletter on substack, twitter, linkedin and blog on Medium. What are your top tips for building a lasting and relevant personal brand?
The reason I started writing is because writing helps me think more clearly. You think you understand a topic until you try and write. Then you realise all the gaps in your understanding. The process of writing makes you more intelligent about the topic – that’s why I write. It’s an outlet for creativity between meetings and emails.
In terms of barriers to publishing online, the hardest thing is getting over the fear of hitting send. I remember the first time I wrote a tweet, I was terrified that I’d said something dumb. The more times you do it, the less you care. It’s a repetition thing and you need to get over that initial hurdle and keep pushing through. Eventually you realise that hardly anyone’s listening anyway so you don’t need to worry.
Have people overall responded positively or negatively to your publishing?
The great thing about publishing is people tell you the nice feedback and don’t tell you the negative, so it all feels positive!
I’m starting to use Twitter as an early feedback mechanism for what I should write. So if I ask a question on twitter and if I get a good response, I know I need to spend more time on it.
On the 23 July, you sent out a tweet calling for women who want to get involved with angel investing – and you received a great response. Can you tell us a little about why you’ve started this initiative and what you’re hoping to achieve?
I had a conversation with a friend and we were talking about the wealth gap between men and women and essentially, it’s not just to do with income, it’s also to do with wealth. Investing is how you create real wealth and women do that a lot less. So I sent off that tweet without spending a huge amount of time thinking about it and got this really great response that got me thinking I really need to do something about this.
It’s still early days, I’m still trying to work out what it’s going to become.
Is there anything that helps you keep momentum with publishing?
Forcing yourself to do it when it feels like it isn’t giving anything back to you.
I was writing online for a few years before anyone noticed. For me the joy was really in getting better at writing and trying to learn more about something by writing and that’s where I got the satisfaction. And so it didn’t really matter much that nobody was reading it. I recommend finding that thing – it’s really about finding internal satisfaction about the creative process and shouldn’t have much impact on your brand to start with. Over time these things build. And I am very much at the start of journey.
Finally, we know you’re a huge fan of books and podcasts. Tell us what you’re currently reading and listening to!
I’m reading a piece of historical fiction by Hilary Mantel. She’s brilliant because she’s really researched the history and you feel confident that it’s historically accurate, but she also builds these brilliant characters and dialogues so you’re learning about history in an interesting way. I’m reading ‘A Place of Greater Safety’.
I’m also listening to an audiobook by Maria Konnikova called ‘The Biggest Bluff’. It’s this story of a New Yorker journalist with a PhD who decides to learn about the influence of luck and skill by learning poker. She gets one of the world’s best poker players to teach her and the whole idea is in a year how far could she get. Turns out she gets really really good. She also tells the story well by weaving in life lessons that she’s learning through the process.