Founders Share the Most Surprising Thing About Being a Founder
Founder Stories

Founders Share the Most Surprising Thing About Being a Founder

Yi Jun Phung
August 11, 2022

It's comforting to know someone else is facing the same thing you are. It's especially true in startups: unless you've been a founder, you won't know what it's like to be one.

As Hsu Ken, our Managing Partner at Iterative, said in this article:

“Being a founder is really hard. Largely because it’s so different from other jobs. At most jobs (1) the company is unlikely to die soon, (2) the business model works and you’re just responsible for growing a part of it, (3) you typically have a lot of support and direction from teammates, managers, etc. None of those things are true as a founder.”

So during Orientation for the Summer 2022 batch, we asked our founders: "what's the most surprising thing about being a founder?”

Here's what they had to say.

Making Decisions with Little Information

A common thread that all founders had was the topic of unpredictability.

Before Steffina Yuli co-founded Kipin, an edtech platform that provides access to education for schools with no internet, she was working at Boston Consulting Group and Tokopedia - established companies with safety nets, with structure and processes in place.

A startup has none of those.

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"When I was in the corporate world, I could extract information easily to make an 80/20 effective decision. It's not the same as when I became a founder. Now, I only have 20% of information if I'm lucky - and have to make a decision within the day itself.”

- Steffina Yuli, co-founder of Kipin

Ben Cheung, co-founder of Soulgood Health, a premium online mental health therapy, agrees too. The company was started by doctors - and as doctors, life is predictable. As founders, not so much.

"You know what your day-to-day life is like as a doctor. But as a founder, you don't have that much clarity. The highs are high, but the lows are lower.”

- Ben Cheung, co-founder of Soulgood Health

Adapting, Fast

The concept of speed isn't new to startups. "Move fast and break things" and “done is better than perfect” are common mantras - and moving quickly is a defining startup characteristic.

But knowing of the situation and actually being in it are two different things - especially for first-time founders. Logan Ye, who founded Arti, a hyper casual, AI-powered guessing game, finds pivoting increasingly common.

“Pivoting is like a strategy on its own. There's an art to it, and being in an industry that changes constantly, I'm always on my toes.”

- Logan Ye, founder of Arti (Metabox)

Second-time founders have also turned this into a skill. Bryant Khor started a fashion rental marketplace before founding ULive, a live-commerce platform for social media sellers, and for him, there are still new surprises every day.

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"Adapting is important - and it's a skill I've had to adopt over and over again.”

- Bryant Khor, co-founder of ULive

Taking the Emotions Out

Hard decisions aren't just unpredictable, they're also emotionally taxing - especially when you're building and managing a team.

You'll be convincing potential hires that your idea is the next big thing in the world, going through lengthy interviews, onboarding them, managing their day-to-days, and soon, realising they weren't the right fit. Then making the difficult decision to fire them.

When Rafid Imran first started Thrive EdTech, a personalised study app, he brought on a friend to join the company. But things didn't work out and he realised he had two choices: cut his losses now or later. He chose the former.

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"This was a close friend of mine, but I had to learn how to not take things personally if I wanted my business to succeed.”

- Rafid Imran, co-founder of Thrive EdTech

Windy Dhaliana fully resonates. She's leading Qalboo, an Islamic wellbeing platform, as an introvert - and is still getting used to feeling the weight of her voice.

"As an introvert, it takes a lot of my energy to manage people. It compounds when the decisions are more emotional, and I have to learn how to take the emotions out."

- Windy Dhaliana, co-founder of Qalboo

Imposter Syndrome is Universal

As a founder, doubt doesn't just creep up - it consumes you fully. You will second guess yourself, and as the main person steering the ship, it feels daunting to be the sole decision-maker. You have to make all of the decisions, even if you're scared, tired, or unsure. Especially if you're scared, tired, or unsure.

A few of our founders across the world shared the same sentiments.

Iman Aqas, co-founder of, a B2B buy-now-pay-later software based in Singapore, sometimes feels like he's answering questions he doesn't know the answer to.

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"We often have to make it look like we know what we're doing.”

- Iman Aqas, co-founder of

Over in Indonesia, Welly Huang feels the same way. He brought his years of technical experience to be the CTO of Yippy, an all-inclusive corporate gifting platform - and still doubts himself frequently.

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Welly Huang, co-founder of Yippy
"I still question myself. A lot.”

- Welly Huang, co-founder of Yippy

Ethan Ang, the co-founder of NodeFlair, a career transparency platform for tech talent, sometimes yearns for someone to tell him what to do.

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"There are a lot of moving parts in a startup, and at times, I want someone to tell me what to focus on first.”

- Ethan Ang, co-founder of NodeFlair

You're Not Alone

Entrepreneurs like Marc Andreessen wrote “why not to do a startup" - not to discourage anyone from building a startup, but to share the realities of it.

We agree - but not so much for transparency's sake (although it is important), more so for providing support. In a world where most of us celebrate more of our wins than share our losses, it can feel alienating when the bad happens.

And the bad happens. A lot.

At Iterative, we think it's equally important to talk more openly about the bad: the challenges, the struggles, the mishaps. A place where founders can open up about their fears, which in turn, helps other founders feel less alone.

If you're a founder reading this, we hope this helped - and that you're not alone in your venture to change the world.

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