Lucy Tan

Sourcing, diligencing and supporting awesome companies.
Square Peg

How did you get here?

I started my career back in 2014 as a corporate lawyer with King & Wood Mallesons. I loved the people but didn’t love the law so by chance, responded to a cold LinkedIn email from a Bain recruiter. At the time, I didn’t have a great knowledge of management consulting and ended up calling my one friend at Bain to learn more. He was so effusive about the firm that it cemented my desire to try it out. Ended up staying there for 6 years so I could see what he was talking about! It’s a fantastic place to learn a baseline analytical toolkit that you can apply to most business problems and the mentorship culture is strong.

At Bain, the job changed quite a lot. In my early years, I focused on breadth. I worked across industries like retail, telco, financial services, industrials and private equity. The cases ranged from operating model, revenue acceleration, cost reduction to pricing and promotions. My goldfish self loved the variety! Eventually though, I ended up doing more and more work in financial services as I was a huge fan of the partners in that practice - they invested a lot in developing me and I was starting to build expertise in the space.  

What options were you considering?

One of the earliest pieces of advice I got from a Bain partner was to not get sucked into the grind and emerge decades later as a partner even though you never considered other options. Given that, I actively tested the market on a yearly basis to see what was out there - that way if I decided to stay at Bain, I knew I actively made that decision. I had a hypothesis that I wanted to work with smaller, more nimble companies and to test that, a friend in VC put me in touch with the Go1 founders. I did an externship with them to help scale up their partnerships channel during their Series B phase. That was a lot of fun and made me realise I wanted to work with startups all the time. When a friend at Airwallex sent me the Square Peg job description, it was the first time that I remember being wildly excited about an opportunity outside of Bain. So I seized it with both hands!  

How did you make the decision to take your current role?

I have a criteria list for qualities I want in a workplace: strong feedback culture, access to talented people at the top of their game + a culture of ownership and collaboration. Through the interview process, I was looking for signals of those qualities and found them to be high. Once I got the offer, I also did some due diligence on the back end - a few partners at Bain put me in touch with their friends in VC once they could see my mind was made up and I reached out to a few people on my own. At the end of it, I was certain Square Peg was filled with people I admire and would love working with and that I shared the same values as them.

What are you doing now?

My role as a VC investor involves 1) sourcing new deal opportunities by meeting founders 2) commercial diligence on the deals that we find exciting and 3) supporting portfolio companies that we’ve invested in.

What does your day to day look like?

Meeting new founders to understand their business and their journey + in board meetings or working sessions with portfolio companies to help them with a variety of issues e.g. fundraising the next round, GTM, strategy, talent etc.

Then occasionally there are weeks where it’s all hands on deck in terms of diligencing a new company to see if it’s something we want to invest in.

What do you love about your job?

My favourite part of this job is meeting new founders. When you meet that special founder that tells their vision in such a compelling way, you feel this unbelievable level of excitement and the need to back them all the way until they’ve achieved their vision. My job is basically me constantly chasing that high. It probably sounds unhealthy but I love it :)

I also love the incredible breadth this job affords. In any one week, you could be meeting founders playing across Web3, proptech, fintech, edtech, healthtech, AI etc. And the range of problems they’re solving are so wide, sometimes non-obvious and niche. And we often go deep into spaces we love by doing thematic research (e.g. for me, it’s edtech and fintech). For that, you’re casting the net wide in terms of trends you’ve noticed, articles you’ve read and synthesising all of that to make a best guess as to how a particular market might play out.

What do you not love about your job?

I wouldn’t say I hate this but it’s a part of the job that I need to make peace with: the uncertainty of outcomes. There are such long feedback cycles - it typically takes 7-10 years for a startup to get an exit. It’s also an industry where you have to be okay with frequent and fast failure - the majority of startups VCs invest in don’t make it to the spectacular Canva-like outcome.

Even though you can be conscious of all those things, it’s still hard to manage the psychology of it. When a start-up isn’t going well, you can’t help but get emotionally invested. I’ve had friends tell me they’ve lost sleep just thinking about all the things that have gone wrong! You have to get comfortable with the fact that there will be things outside of your control and all you can do is support the founders as best you can.

What advice would you give someone deciding what they should do?

What gives you energy. If you're considering venture capital investing, I think you have to fundamentally get energy from meeting LOTS of new people and networking. If you don’t, then it will feel like a grind.

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