6 min read

Interviewing CEO Of A Billion Dollar Company In The Making

Interviewing CEO Of A Billion Dollar Company In The Making

From my previous blog "How doing this can change your life" I talk about how I was able to overcome your fears when it comes to getting yourself out there and in doing so, has changed my life. So I thought what better way to show you guys but to actually prove it through demonstrating what I've learnt from speaking to the amazing Co-Founder and CEO of Checkbox Evan Wong.

Evan is someone who I admire, respect and look up to as a role model. He's passionate about entrepreneurship, technology, education and obsessed with personal development for not only himself, but everyone around him. He has not only founded one but two successful and award winning companies. The first being Hero Education and now the enterprise software company Checkbox which is a $1 Billion company in the making.

I stumbled upon Evan's profile through trying to find someone who has had a similar career path as myself. Evan was also a tutor and an aspiring entrepreneur who has made his dreams come true. So I thought, what better way but to leverage his experience to achieve my own aspirations and for anyone else out there who is in a similar situation and who would like to know what it was like building a business from the ground up.

Lesson 1: Overcoming The Concept Of Money

Photo by Towfiqu barbhuiya / Unsplash

As I spoke to other aspiring entrepreneurs I have found that money was always a barrier for a lot of people who want to venture out and build their own business. Why would anyone give up their day job which is providing a consistent cash flow and is their safety net and the backup plan if all things go wrong? There was a quote that had always stuck to me which goes like:

"The moment you are able to realise that money is not real, is the moment you can start becoming successful".

This was how Evan overcame the concept of money:

  1. It requires personal sacrifice of the "luxuries" and "privileges" that most people around his age had. At that time he was in his mid twenties and did not own a car, gave up going on holidays and would use that money instead on investing into his business. His mindset was "Where could I best invest my capital" which is very different mindset to the majority twenty year olds out there who just want to party and enjoy the weekends.
  2. Having a steady source of income before you make the move. Evan worked overtime to build the reputation and resources required to make Hero Education successful enough to hire others to run the company. This was how he was able to get a steady source of income to invest back into his new business. Which then leads on to:
  3. Being able to afford the luxury of time. Once you've been able to establish a passive income, you begin to understand that what is truly valuable isn't actually money, but it's actually your TIME. As I mentioned in my previous blog, you are just as valuable as anyone out there and thus, your time is the most valuable resource of them all.

His advice to anyone who is an aspiring entrepreneur was: "Just start right now, learn to build your skills and learn to scale your time"

Lesson 2: Fail Successfully

scrabble, scrabble pieces, lettering, letters, wood, scrabble tiles, white background, words, quote, fail your way to success, persevere, don't give up, try again, get up, move on, keep innovating,
Photo by Brett Jordan / Unsplash

The idea of an "overnight success" is a HUGE misconception and almost deceiving to everyone because with every success story there are countless failures within them. Evan likes to use the phrase "Fail Successfully" which he explains that with every failure, make sure that you learn something from it in order to make it a successful one and I couldn't agree more as I have always been a big believer of learning from failing (see my blog post 3 Reasons Why I Tutor specifically: "To Fail Is To Succeed") as it allows us to grow into someone better.  

I love listening to everyone's journey as its an opportunity to learn from their mistakes. We often mistake "Failures" as always needing to be "Big" failures when in fact you could face failures on a daily basis also known as "Micro-failures". Evan talks about how he overcomes his micro-failures through staying true to his values and beliefs. If things aren't aligned to them, he tries to understand why it happened and then pivots his business towards his ultimate goal. But in reality, it is all about HOW you define failures as it could have multiple definitions and it is actually a personal choice at the end of the day.

The way Evan defines failures is:

A startup doesn't fail, the founder does.
By Evan Wong

This is such a powerful quote by Evan as it demonstrates two things:

  • As long as you don't give up, your startup/business will never cease to exist
  • He doesn't think of the lack of money being the centre of the business but the people driving the business as the pivotal factors of a successful business

Lesson 3: Principles > Feedback

Not all those who wander are lost…
Photo by Aron Visuals / Unsplash

As we all know, receiving feedback is a great way of improving yourself and to understand what could have went wrong. It can come in as either positive or negative feedback but we need to make sure that we take it with a grain of salt. Now what do I mean when I say this?

Now picture this, you're planning on starting up an e-commerce business and start by asking all your friends and family about how to design it. They all put through their thoughts about it (positive and negative) which gives you multiple directions of designing it. If you were to take in account every single design concept that was given to you, how do you think it'll turn out? Probably not well. It is important to align any or every feedback that you receive to your "core principles".

Evan does extremely well in keeping true to his core principles when faced with negative feedback. He has always believed in the "people" aspect of things and believing that the characteristics of a person is much more valuable than their experiences/skills. The CTO of Checkbox was someone who once had ZERO coding knowledge but had the determination to learn it and believed in the same core principles as Evan. Not only once, but a few times a lot of venture capitalist would not fund his business due to the lack of experience (years) his CTO had. The funders would only invest their money if the CTO was someone who was coding their whole life and had 10+ years of experience. Instead of changing his team, Evan would turn down the investors money and believed in his team and would only align himself with people who would believe in this core principles.      

I found that this was a truly admirable characteristic of Evan. Being able to turn down investment for his business (which I believe most people wouldn't) because he believed in his values and principles. We go on to talk more about:

  • How did he know Checkbox was his true calling
  • How did he build his team and find his business partner
  • How he started up his HERO education business and scaling it

But for the sake of this blog, I wanted to keep it to the top 3 lessons which I've found which was eye opening to hear. If you guys want to hear more about our interview or even connect, please feel free to subscribe to my blog where I'll be posting weekly content and comment below on what else you'd like to hear.  


"Chase the vision, not the money, the money will end up following you"
By Tony Hsieh