Luck is what happens when preparation meets opportunity

This is a multi-part series sharing the lessons I’ve learned on my entrepreneurial journey thus far. Here is the second lesson. Read the intro, and first lesson, if you haven’t already done so.

The quote: “luck is what happens when preparation meets opportunity” is attributed to Roman philosopher, Seneca, and it rings true in many situations, particularly startups.

Photo by Dolo Iglesias on Unsplash

We often hear about the success stories. And when you go behind the scenes, more often than not, you realise there are moments along any startup journey that appear to be based on sheer luck. But no one in business ever became successful purely because of luck.

Said another way, it’s one thing to be lucky, but what matters is preparing yourself to be in the best position to take full advantage when it happens.

During my Demo Day pitch, I said:

I feel like my whole career has been one long training course, leading me to this point.”

Antler Demo Day Sydney — Ian Yip: Avertro

Without my 18+ years of cybersecurity experience, I wouldn’t have the insights, decision-making ability, leadership skills, or business network to successfully get us to where we are today. We still have a long way to go, but we’ve achieved a lot in a very short amount of time.

In addition, despite my prior speaking experience, the preparation for Demo Day included a lot of rehearsals. You cannot shortcut good preparation, no matter how much experience you think you have.

Antler Demo Day — One of the many pre-event rehearsals with the founders running through their pitches on stage prior to the actual event | Photo credit: Antler Australia

Here are a few other examples in my journey thus far where the confluence of luck, preparation, and opportunity has been crucial.


Luck: Finding out about the Antler program.

Preparation: My corporate career to date, and my deep expertise in cybersecurity gave me the skills I needed to be accepted onto the program.

Opportunity: Being accepted into the Antler program to learn, work with a bunch of high-achievers, better myself, and potentially start a company.


Luck: Finding my co-founder.

Preparation: Years of experience working across different roles, functions, and with different people, gave me the ability to understand the complementary attributes I needed in a co-founder, and to be able to identify them in a person.

Opportunity: Someone who possessed the key skills I needed in a co-founder to give our company the best possible start and chance at success.


Luck: Being placed in a highly-visible situation to communicate with a large audience of very important people at a tentpole event (i.e. Antler Demo Day Sydney).

Preparation: Years of communicating with groups of people in similar situations due to the requirements of my various corporate roles, including at large conferences and in front of global television audiences, gave me the confidence that I would be able to rise to the occasion.

Opportunity: Securing new investors and customers for Avertro.

In a startup, many things have to go right, and not all of it is within your control. Luck absolutely plays a part. But you’re not going to get anywhere, if you don’t do the work, and if you don’t actively bring all the things you’ve learned along the way through your successes, and more importantly, your failures, with you.

I had the opportunity to meet a few of the fantastic incoming Antler Sydney cohort that start in January. The one piece of advice I gave each person that asked was:

Embrace all your experiences and failures, figure out what makes you stand out, and learn how to articulate that uniqueness and value in 30 seconds.

Because when opportunities arise, you need to be ready to bring all that preparation into play if you want to be lucky.

Read on for the next lesson.

Ian Yip is the CEO of Avertro, which brings science to cyber story-telling by providing a simple, yet sophisticated executive and board cyber platform that helps organisations tell a compelling story, right-size their cyber program, and understand their cyber-why.

Cyber Risk. Cybersecurity. Business. Tech. Entrepreneur. CEO at Avertro. Former CTO at McAfee Asia Pacific.