How to choose a founder coach in Singapore

By Willis Wee

28 October 2026

I wrote this after researching into founder coaching. Some of what came back felt like BS to me. I wanted to know whether the people it recommended had actually done the work.

Personally, I'm wary of coaches whose experience is entirely corporate. Running a startup can mean deciding with little money, incomplete information, and nobody above you to take responsibility. Sorry, but I don't think corporate experience alone prepares someone to help with those decisions.

I give people the benefit of the doubt about their intentions. But advice that ignores those differences can hurt a founder and their team, imo.

I'd ask about their experience:

• Founded a company?
• Built and shipped a product?
• Hustled, ran sales, faced rejection?
• Carried out a layoff?
• Ran out of money?
• Raised money?
• Been through an exit?

Ask what happened, what they got wrong, and what they learned. You don't need someone who's done everything on that list. You need experience relevant to what you're facing. With layoffs, I'd want to hear them take responsibility for the people who got hurt.

I also have a stake in this. I'm a founder and dad in Singapore. I spent 16 years building Tech in Asia, from zero to YC to exit. I coach founders on the side. I've made enough mistakes to know that my experience won't fit every situation either.

Start with the thing you're stuck on. Maybe you're testing an idea, avoiding a difficult conversation, or trying to work out which projects to stop. See whether the person understands it before telling you what to do.

You don't need a polished brief. Describe what's happening, who's affected, and what you've tried. If you're overwhelmed and can't name the problem, say that.

What happens during a session?

People use coach, mentor, adviser and consultant differently. Ask what you'll actually do together. Will they ask questions, share operating experience, give specialist advice, or help you make a plan?

With me, we may work through the context, discuss an example from my experience, or draft a plan. You decide what to do and carry it out. If you need someone to run the project, say that before booking.

Ask about a decision like yours

An exit doesn't mean someone understands every problem. Ask what they chose, what went wrong, and what they'd do differently.

In 2018, we stopped several projects at Tech in Asia and focused on content, events, and the jobs portal.

The jobs portal was a profitable subscription product driven by our traffic. AI recruiting still needed outbound sales and cold calling. It felt like a separate business.

Running both made it hard for me to focus and lead. After narrowing the focus, I had fewer reports and decisions, and more room to think.

Can I disagree with you?

You should be able to say, "That doesn't fit my situation." Pay attention to what they do next. Do they ask what they've missed, or keep pushing the same answer?

I've written about being selective about advice. Someone else's success doesn't mean their approach will work for you. Ask why it worked, what was different about their company, and which part is worth testing in yours.

What would make this session worth paying for?

Before booking, finish this sentence: "I'd be glad I paid for this session if I left able to ___."

You might want to compare two options, identify information you're missing, or prepare for a difficult conversation. Ask the coach how they would help you work towards that.

With me, we may work through your options or draft a plan as comrades.