Ask venture capital expert Tan Yinglan about his best investments to date, and he is likely to say they are his three children... A former government scholar and Administrative Service officer - he stresses that he served out every day of his six-year bond - Mr Tan set up Insignia after five years with the giant US venture capital firm, Sequoia Capital. "From being the referee, I wanted to be a player, then coach and owner", says the Liverpool Football Club fan and only child of Singaporean school teachers, explaining his move to leave the secure grooves of government for a career in risk-taking, and eventually, his own firm. — The Straits Times

I came from Malaysia’s largest Chinese independent high school founded with the vision of preserving Chinese culture and language for future generations to know their roots. Looking back, I remember how annual fundraising events played a huge role in helping the school endure for as long as it has. Everyone from the board, faculty, alumni, students and parents were involved in the project. We would spend months looking for product sponsors, organizing performances and gala dinners, and knocking door-to-door for donations. This school tradition helped me to stay rooted and have deep respect for all the school alumni who paid it forward to ensure that this education would endure. My school will be having its 108th anniversary this year.

As with most teenagers, I used to spend my time playing trading card games when I was in secondary school. We would assemble the best deck of cards and try to best each other in a battle of wits and strategy after school everyday. This afterschool affair quickly turned into a side hustle of buying and selling the most sought after cards to other players. This first brush with entrepreneurship sparked my aspirations. It was not as scalable as the businesses I work with today, though it was profitable! And little did I know then that this would lead me on a path to supporting the growth of Southeast Asia’s leading tech startups.

I remember representing my school at a local TV production -- Little Entrepreneurs -- where we competed with other 11 year-old kids to source products, come up with a marketing strategy for these products and sell them in public. Such a tall order for 11-year olds! My entrepreneurial dreams were ignited from this short stint on TV, and today I find it fascinating to be working with companies doing essentially what we did then, except at a much larger scale, for millions of people across the region, and for years to come.

Growing up I remember my grandmother waking up every day at dawn to bake bread and sell it to restaurants. And I would help my grandmother pour the dough and wash the pans. This grit and perseverance I learned from my grandmother is something I embraced more, as I sold baked goods and t-shirts in high school and built a crowdfunding property startup in university. What’s amazing about my experience is that this story of grinding to build a business is the daily life of millions of Indonesians, and that’s what inspires me to work with Indonesian entrepreneurs as a VC.

When I was in Seoul for a university exchange program, my friend and I spent our off-hours in networking events getting to know the local startup ecosystem. And to give ourselves a goal in our four months there, we decided to organize a university pitching competition, with zero budget, near-zero connections, in a country that largely didn’t speak English. Through networking and social media, we put together a humble event at the Seoul Global Startup Center that drew in undergrads from across the world, only having to spend for a few boxes of pizza. After the event, we were able to send the winners to Stanford for a summer bootcamp. My friend and I also got internships at the firm of one of the judges we invited, where I incidentally learned about Insignia

Eraser battles were all the rage in primary school. They were rectangular erasers with country flags printed over them, and each player would take turns flipping these erasers with the goal of landing on their opponent’s eraser. As there were frequent recess time tournaments but players without erasers, I bought an entire box of country erasers from the neighbourhood bookshop and sold it to my classmates for 100% profit or greater. Working at a venture capital firm seems like a far cry from selling erasers, but I still find myself working in an industry that invests in companies addressing unmet needs and inefficiencies, and creating immense value from that.