Career Skills & Transitions with Lily Wu, Startup & VC Partnerships at Stripe

What’s your career story so far?

I’ve always been attracted to the unconventional path. 

I grew up in an artists family, so I always thought I would do animation or architecture out of high school.

After the 2008 financial crisis, when I was ~16 years old, I discovered arbitrage opportunities between the US and Australia, and started reselling high street sneakers. By the time I finished high school, I had made 6 figures. Because of this experience, I then thought accounting (as a core function of business) would be a good skill to have, and joined a global accounting firm on a 4 year contract.

I soon realised I hated accounting, and co-founded a 2nd company, Austern International to help university students (like myself at the time) experiment with what they wanted to do in life, gain work experience and develop transferable and entrepreneurial skills. This grew into a million dollar annualised revenue business, and over 5 years, expanded across 7 cities. After exiting, I travelled for 9 months across Europe and Latin America, joined an education startup in Singapore and helped them raise their Series A.

Over the past 2.5 years, I’ve been at Stripe leading startup partnerships, building out the VC and startup ecosystem across APAC, for Stripe to better support founders at the earliest stages.

What ingredients were most important early on in your career?

Most skills can be developed on the job but coming with the right mindset and attitude is important, especially early on in your career.

1/ Have a beginner’s mindset. This means being open to, and welcoming constructive feedback, as well as continuously seeking ways to be better.

2/ Be proactive. When I first moved to Singapore, I didn’t know a single person so I was shameless in reaching out to people on Linkedin, meeting for coffee and connecting with people that way. I have built entire networks from scratch also across South East Asia and the US by being proactive. That’s how you maximise your “surface area for luck”

3/ Give to others. Don’t look at life on what you can get. View situations from the perspective on how you can help people solve their problems. It’s a human world built on relationships and trust.

What is the biggest career transition you’ve made? What helped you to take this step?

My life has felt like a series of transitions. This includes going from being an artist, studying accounting and business law, starting a business in education, to working in fintech, and in 2022, raising $2M in 4 days to support women entrepreneurs in web3.

I’ve always made decisions led by my values rather than what I think a specific career path should look like. Whenever I look at a specific opportunity, I think about whether they will allow me to become the person I want to become, and the life I want to live.

These values and questions I ask myself are:

Curiosity: What can I learn? How can I merge multiple interests together? What problems can I solve?

Freedom: Do I have the freedom to experiment? Will I have flexibility in my working style?

Impact: Is my work purposeful? Can I build from 0 to 1?

Relationship building: Will this role allow me to create meaningful connections externally, as well as collaborate internally?

Getting clarity and being introspective helps cut the noise on the steps you want to take next in your life, whilst maximising on your strengths and passions.

How have you built your own professional toolkit over time?

A book that has helped change the way I manage my personal and professional toolkit has been “Building a Second Brain”.

We’re constantly building up our repertoire of projects, we’re consuming a lot of resources, and I found that by optimising the timeliness I can draw upon all my experiences and resources is so important. This has helped me expand my memory and form new connections that I wouldn’t have spotted otherwise.

How do you approach learning new skills?

My learning process can be summed up in these general 5 steps - whether it’s a new skill at work or learning a new language. Everyone has different ways of learning but I learn best by doing.

1. I’ll give it a first attempt at doing the skill
2. I’ll identify what is transferable with my current skills, and what gaps are completely new.
3. Fill in the gaps with mentorship, studying, resources, etc.
4. Practice & learn from my mistakes. Get feedback from others
5. Repeat until I’ve nailed the skill

What’s the best career advice you’ve received?

1. Always be willing to disrupt yourself.
2. Do your job so well that you can replace yourself (which leaves room for solving bigger problems, being cross-collaborative, creating new projects).

What’s one thing you wish you knew when you first started your career?

Every choice you make has an opportunity cost. Saying no is just as important to what you say yes to. Every time you say yes to something, it means you are closing the door on all the other alternatives.

What’s one resource that’s helped you in your journey?

I’d say the most important thing to get clarity on your journey is understanding your why, your habits and your mindset. The why determines your direction, your habits show you who you will become, and your mindset gives you perspective with the rollercoaster ride that life puts you on.

• Designing Your Life: by Bill Burnett - this helped me to reflect on my strengths, my direction in life and how I want to be intentional with how I lead it
• Atomic Habits: by James Clear - If you can improve 1% every day for a year, you’ll be 37x better than when you started.
• Almanack of Naval Ravikant: by Naval Ravikant - I’m a fan of stoicism and this book really helps with gaining perspective with the ups and downs in life, and really focusing on the important things