5 Questions Founders Overlook When Pitching Their Startup

From odd questions like "can you be a cockroach?" to the standard "what's your weakness?", these are the answers you should have prepared when you pitch to an investor

“What I really want to see is how well founders react under pressure,” says Tak Lo.

As the founder of Newtype—an early-stage accelerator focused on backing founders in AI, blockchain and robotics—Lo has spent hundreds of hours listening to entrepreneurs pitch.

As a result, he’s built up a bank of questions that are, more often that not, overlooked due to their perceived "run-of-the-mill" nature. In actuality, Lo says, it’s these very questions that give him the information he needs to know about the founders, their team and their company.

“I want to gauge their intellectual capacity and their group dynamics,” he says. “I deal with more early-stage entrepreneurs, so I'm actually more concerned about the team and the founder and who they are, rather than the pitch itself.”

A common theme in Lo’s line of questioning is getting entrepreneurs out of their comfort zones to see how they react. “Entrepreneurs need to be able to face up to awkward situations with the same level of tenacity, passion and discipline as normal situations,” he says.

“Sometimes I’ll say [to the founder], ‘Hey, jump with me!’ and then start walking and we’ll do their pitch session while they’re walking—so you’re taking them out of their normal situation and making them run with it.”

Here are five questions Lo says every founder needs to have a good answer for.

What's Something You Don’t Like About The Other Person?

When the founder walks in to deliver their pitch, what’s the first thing Lo does? Make them uncomfortable.

“If I see a teammate, I’ll pick one person and say, 'Hey, what is something that you don't like about the other person?' I basically want to see how they react to an awkward question.”

Lo says he usually asks the CTO about the CEO. “The CTO is usually the quiet one who is observing everything, so it’s interesting to see the CEO from a different angle.”

“I also do it to see how the group dynamics are—are they comfortable enough to talk about that or are they trying to hide something? Sometimes you determine that they don’t actually know each other well enough either.”

I want to know if they have suffered. Can they survive? Can they be cockroaches?

- Tak Lo -

Why Are You Pursuing The Field You're In?

When asked why a founder is pursuing the field they’re in, Lo says the usual response is because they did market research during business school and identified it as a growing market.

It's an answer to which Lo has two responses:

First: “That was like a college application—soulless.” Second: “As an ex-consultant, I can prove anything to be a growing market.”

“But if someone says, 'Well, I’ve been in this industry for about two to three years and I’ve learnt that actually this is the key insight, and nobody else is doing it.' Well, then that piques my interest.”

That's not to say insight is some sort of secret sauce that will drive the company’s success, says Lo. But it shows him that the founder is astute enough to really try to get to the fundamentals of what they’re doing. “And it shows that as things change, they’re always able to change and be one step ahead of their competitors.”

Everyone has a weakness. It’s impossible not to have weaknesses. So I want to know, what is one thing you’ve failed at? And what did you learn from it?

- Tak Lo -

Do You Have Passion For What You Are Doing?

Passion is a non-negotiable, says Lo.

When it comes to determining how well the founder and product fit, Lo will always ask, “Why are you doing what you’re doing—are you passionate about it?”

He isn’t looking for a breakdown of what you’re doing, instead he wants to hear about the passion you have for your product. He wants to know that “we could spend a significant amount of time talking about the product and the nuances of it.”

What Is Your Greatest Weakness?

What Lo is trying to ascertain from this classic interview question is your level of intellectual honesty.

“Everyone has a weakness. It’s impossible not to have weaknesses,” he says. “So I want to know, what is one thing you’ve failed at? What is one thing you can improve on? And what did you learn from it?”

By answering that, it shows your ability to depersonalise the business, “as well as a certain judgment of one’s self and self-awareness.”

Can You Be A Cockroach?

“I want to know if they have suffered,” says Lo. “Can they survive? Can they be cockroaches?”

“I want to hear stories about when you didn't have the money to make the team last for another five months, but you managed through your perseverance and inspiration alone,” he says. “Because entrepreneurship is really about getting to the next phase. I want to know if you can survive until the next phase, because only if you can do you have a shot at getting to the next phase and then the next phase—and then you can win.”

See other honourees from the Technology category of the Gen.T List 2019.

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