Looking back at my startup journey

Yin Sylvia
5 min readFeb 11, 2023

In a blink of an eye, I am one year into my career sabbatical. As I’m preparing to be a Visiting Partner at Iterative’s Winter 23 batch, I thought reflecting on my startup founder career would be timely.

The most valuable lessons I have learned have come from hearing stories from fellow founders. By sharing my journey, I hope to provide some context to my experience for the founders I will be working with and how I can be a resource to them.

An accidental founder

I am an accidental founder. Growing up, I never imagined starting a company from scratch, which is funny in retrospect as both of my parents are entrepreneurs. Mom started her first hair salon business at 24, while Dad ran his hardware and timber trading business in his hometown Ipoh.

Both grew up poor and did not have the opportunity to finish high school. Mom dropped out of school and ran away from home at 16. She moved 207 km from her hometown to our capital city, Kuala Lumpur, to take up jobs at hair salons to help my grandmother make ends meet.

Top — Mom behind the reception counter at her salon; Bottom — Mom’s salon

Through entrepreneurship, both worked incredibly hard to give me everything they did not have growing up — stability and comfort. It meant I could have a private education and go abroad to the UK for my degree. These led me to an internship opportunity at the big 4, and I was set to go down a conventional career path.

However, life has a funny way of working, and I believe the universe gives you what you need versus what you want. At the ripe age of 21, the universe decided I needed to be put on the path of a startup founder.

Eight years “gap year”

By the time I graduated from university, I had been feeling for some time a nagging sense that this can’t be it. I can’t possibly have life’s next steps already figured out as a 21 year old.

I decided to take a gap year, and it was during that time Kendrick, a former classmate reached out with an idea for a product discovery app for the fashion retail industry. He then asked me to be his co-founder.

Like most 21-year-old females, I enjoyed fashion, was intrigued by the idea and decided why not since I am on a gap year. And so I joined Kendrick as his co-founder and embarked on a “gap year” that lasted eight years.

Becoming a founder

I stepped into the role of COO and took on the challenge of ensuring the company is a well-oiled machine by looking after its overall business operations, from product management, people & culture to customer management.

Over time, we realised that our B2C affiliate commission business model wasn’t the direction we wanted to go. With the same co-founders, we began afresh and started a B2B SaaS retail analytics business. That was when things began to shift gears.

One of the very first product meetings with the engineers. It was done on the floor and bean bags, of course. It’s a scrappy startup, after all!

Getting your first few paying customers is always challenging, but within 18 months, we broke the USD$ 1MM ARR mark and raised Series A. Our team grew to 60+ employees across South East Asia. It was an exciting time as we saw our product used by regional and global brands like Zalora, Lenzing, Uniqlo and Lidl.

During this growth, I discovered my interest in Customer Success and had the privilege to build a fantastic team of Customer Success Managers to lead post-sales revenue growth with me. I’ll never forget the excitement when our NRR hit >100% for the first time. Something is working, and I got to do that with people I enjoy working with!

But as if the startup journey is not uncertain, ambiguous or intense enough, COVID hit in 2020. Almost every challenging part and more about running a venture-backed, built-for high-growth tech company were amplified.

Difficult decisions had to be made, uncomfortable conversations held, and I had to learn to trust that we made the best decisions we could given the circumstances and the limited information we had.

As an empath, it was an incredibly intense period for me as I had to learn to balance my worries and fears with those of the team while maintaining a clear head as we navigated the situation.

Taking a break

After eight years of startup marathon, in January 2022, I decided it was time to shift my focus to cultivate other areas of my life that I had neglected. Building the company was all I did in my 20s.

New friends I made while hiking during my solo backpacking trip in Greece

Reflection in retrospect

The sabbatical allowed me to reflect on my experiences as a startup founder. After all these years, I remain convinced of why I fell in love with entrepreneurship in the first place.

Running a startup is a journey of self-reflection like no other. It requires you to be extremely honest with yourself, work to understand your strengths and weaknesses and be accountable for your actions and their consequences.

In a startup, if you don’t row, the boat doesn’t go anywhere. It’s an environment of extreme ownership. It demands that you think clearly of the outcome you want and take action, even though you don’t have all the answers. The journey also teaches humility as you learn to recognise that while you are the captain of the boat, there are always the elements.

And because the journey is so intense, you end up forging amazing friendships with those you work closely with and your peers. This is one of the greatest gifts of my startup journey.

The startup journey can be intense. The highs can be high, but the lows can be very low. Without the community of founders, mentors and peers, the journey would have been far more challenging.

Founders helping founders

Recently someone asked me at a party if I believe in founders helping founders. I told him absolutely because I had experienced it for myself. I joke that it takes a village to raise a startup, but I think it’s true.

Dinner with fellow founders from the SEA Founders community. Check them out here!

This is why I am excited to be working with the founders from the Iterative Winter 23 batch. Just as I had benefited from the experience and advice of other founders and mentors, I hope, at the very least, I can lend empathy and perspective to the roller coaster ride of being a startup founder.

Iterative is an accelerator focused exclusively on Southeast Asia. Founded by cofounders of Decide.com (acquired by eBay), Iterative differentiates itself with partners, mentors, advisors, and investors who have all previously started, sold, and operated startups. Iterative invests in companies on a rolling basis, so you are recommended to apply now. Learn more here.



Yin Sylvia

B2B SaaS • BizOps • Customer Success • Swim • Pilates • Yoga • Pawrent to 4 doggos 🐶