WDKY 1820 – The Myth of Failing Fast


28 May 21

WDKY 1820 – The Myth of Failing Fast

Podcast: Play in new window | Download

For Episode 1820 of the WDKY podcast, I interviewed Tan Teik Guan, former CEO/CTO/Co-founder of security software startup DS3, which sold successfully to Gemalto, and two failed startups. Here is a quick excerpt.

When the employee tells the boss what to say

You’ll find the full episode here. Other highlights from our chat:

I passionately want to debunk the notion of Fail Fast.

It’s a very scary thing. I guess when the phrase first started, it was about really executing, running as fast as you can, and then trying to find out whether you’re right or wrong. But it’s been used in a much more convenient way where you would just say that if I’ve started something and I almost engineer it to fail, then I’m sort of successful in that way. That’s s**t. I see people’s LinkedIn profiles and they’re proud to be a failed founder. My god! Did you really do everything you possibly could before you said that it didn’t work?

You know, when you run something and you believe in it, you should really run without a safety net. And you have pushed it to a limit, you have tried almost anything and everything, and you realise that your fundamental beliefs in the beginning were wrong and therefore you will either need to pivot or actually stop. That’s probably when you can then say it’s failed. But not so much, I’m coming out here, I’m going to run a startup and probably in about six months, I’ll probably fail. That’s fine. Because now I can claim myself as a failed founder.

You know what we call them – wantrepreneurs – you know, I want to be an entrepreneur. I think of them in my head as tourists. If these guys do this in their own time, that’s fine. But if they continue to perpetuate this and say that this is a good virtue to have, then that’s really scary. I see some of these programmes talked about at schools, I shall not name them. I’ve seen slides that talk about this. The “fail fast, fail often” stuff in educational slides about entrepreneurship in schools. And that’s scary. That’s not what you tell students. You have to tell them that, as an entrepreneur, you really have to go out there, be fully committed and yet be prepared to fail. I think that’s a fundamentally different thing altogether. The emphasis here is the speed and commitment, not the failing. But we’ve got that warped. That failing becomes the emphasis and I worry. I worry for what we are at least perpetuating out there.

It’s too broad to just blame it on a whole generational thing.

It has to do with both the culture but also the whole technology side of things. I tend to blame it actually on more computer games, because of the restart button. In the past, to restart an arcade game, you put a coin in. Now, games are like, restart anytime you want. You stop, restart, reload. It’s very easy. There’s no cost to it. And because of that culture, they don’t see failure as something that needs to be learned from. Never mind, I can always restart.

The company makes the people and the people make the company.

In the beginning, when there is this overall view of what you want the company to do and people start to come, it’s more of the company making the people because you attract the people in. But as the company grows to a point where the people within the company actually define the culture, they, rightly or wrongly, bring their own baggage and their own ideas, and they make the company a part of what they are. Or the company becomes part of what they are. And when that happens, the company’s growth is not left to one person to say, hey, we are going to go in this direction or that direction.

It’s worse than marriage.

It’s harder to find a good co-founder than to find a good wife. I’m not kidding you. I would say communication is probably the make or break. Let’s be clear. No group of people will think alike for an extended period of time. You may have a common goal in the next six or 12, even 24 months. Communication actually both makes or breaks the dynamic within the team itself. If something is communicated in a way that allows for everyone to talk about each other and shout it out, fight it out, I would say that that helps bring the company forward.

You cannot have people just saying yes to you all the time.

That’s a really dangerous organisation to be in. In the beginning, I was so customer-oriented. Whatever customer says, customer gets. Everything they say, I say, yes. And then you realise the company grows to a certain size, there are people in the company that literally have to say no to this customer, because the customer is too demanding, they didn’t pay for it, etc. When that person says no and the customer gives me a call and I say yes, that’s affecting my employee and I get scolded for that by my employee. There were times when she told me, “This customer is going to give you a call and you jolly well say no.” And I would then struggle to say no, but I eventually would say no.

Anyone can be a CEO; a founder is a different thing.

It’s what kind of CEO you are, and that’s a totally different topic. When I was in my second startup, one of my co-founders told me this. If you start a company, you cannot look back and look at your safety net behind you. You have to do stuff until there is nothing left to do. You don’t think that there’s something to catch you if something fails and because of that, it drives you in a different way from a regular employee or executive because really your life depends on it. If it fails, that’s a separate thing altogether, but when that happens and when you put yourself into that position, you might see a different side of you.

We had lots of failures

and lots of products that didn’t go out to the market, with many attempts. But just one or two of them really change the whole business. And so that was what I did. It was sort of like playing lottery. I allocate a higher percentage of resources and time to doing something crazy. I tell my guys, look, you have 100% of your time, you can spend 80, 90% doing what you need to do. And that extra 5-10%, go try something else. Please discuss with me on what you want to do, but try doing something else. And quite often they do stuff that even wows, me, you know, and that was a wildcard that I had thankfully.

What is framed as a problem in academia is actually an opportunity in industry.

If you’re in research and you want to cure cancer, that’s a problem. You want cancer to be cured. But curing cancer in industry is an opportunity. The problem is who to sell to. I think that’s a different thing altogether and the researcher needs to take his mind out of trying to solve the cancer problem, but instead really try to solve the problem for the customer he’s trying to sell to and that takes a lot of time. Having engaged with so many of these tech founders, I see that it takes a lot of time for these people to understand that and to take their mind off the whole novelty side of things.

I had beer for breakfast.

We were trying to close a sale with one of the biggest banks in Vietnam and it was down to the final negotiations. This was in the morning, and I got pulled out to meet the deputy general manager, the super-senior guy who was overseeing the steering committee. I went there and what I saw in front of me was a table like this, right in front of me and just beer. So I had beer for breakfast in Vietnam. And, oh my god – bear in mind, I hadn’t eaten that morning so I had just beer for breakfast. I was struggling because I was trying to listen to him, I was trying to answer him in decent English, without trying to sound condescending, yet trying to fight the buzz, and trying to stay alive without knocking the table over. Thankfully, we got the deal.

There is a lack of locals within our entrepreneurial pool.

I don’t mean to say that there aren’t any. There are. But they are in the minority. You’d expect that in Singapore, they should actually form at least the equal or the majority. If within Singapore, within the greater South-East Asia region, entrepreneurship needs to become the backbone, or at least a very strong industry driving how these countries move forward, then I’m very worried why we don’t have sufficient people to form that backbone. Is it a legal problem, an education problem, a policy problem, a funding problem? I don’t know. And that worries me. If we want Singapore to transform, but we don’t have the people in Singapore, or at least the Singaporeans to really want to participate at the different levels, then we’re going to have that gap again. And that is scary too.

Everyone can benefit from being an entrepreneur at some point of their lives.

It can be a six-month, one-, two-year thing, and then they go back to being an employee, but you will realise that you are so much more effective as an employee after being exposed to the entrepreneur journey. Go out there, challenge yourself and you’ll realise whether you are really cut to be an entrepreneur or you should just go back and be gainfully employed. Nothing wrong with that. But you would have benefited from the entrepreneur journey and that’s something that I really advocate.

Tan Teik Guan is a hardcore computer scientist. After earning a degree in computer science at the National University of Singapore, he worked in IT Security at the Monetary Authority of Singapore, before being bitten by the startup bug. He then became the CEO and CTO of the security software startup DS3 for about a decade. Teik Guan led the sale of DS3 to the security multinational Gemalto and continued there for three years in VP roles. But this success came only after two earlier failed startups – a mobile payments company and a B2B fintech startup. In recent years, he has been mentoring a number of tech startups while pursuing a PhD in quantum cryptography.

Teik Guan may be in academia now but one could never mistake him for an ivory-tower theoretician – he is a “doer” by temperament. Listen to this episode to learn why everyone can benefit from being an entrepreneur at some point in their lives.


Teik Guan’s profile: LinkedIn

Episode transcript: Download

Teik Guan’s chosen charity: Teik Guan is a volunteer, committee member and donor of the Association for Persons with Special Needs. He encourages others to get involved with the APSN. Alternatively, listeners may like to join Murli in donating to the UN’s World Food Programme (winner of the 2020 Nobel Peace Prize), which does important work distributing food to approximately 100 million hungry poor around the world.


I am a B2B Tech Founder

learn more

I am an Investor or Investment Professional

learn more

I am a potential customer or partner for your portfolio

learn more

I would like to contribute my talent

learn more