WDKY 1818 – Hooked On That Feeling


18 Mar 21

WDKY 1818 – Hooked On That Feeling

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We recently interviewed Ben Tan, co-founder of Tin Men Capital, for Episode 1818 of the WDKY podcast.

I am an expert at failing and then succeeding, or vice versa. I started my first company purely out of vanity when I was in the second year of university. It was the first internet applications company ever started in Singapore, and it was really fresh out of a successful project team we had. That’s how it got started. We went through the high highs and the low lows of the dot com boom and crash. In the end, I lost that, and then went on to start and operate a few more. Really, you get hooked to that particular feeling and the feeling is simply this, to be on the forefront of something new that no one else has.

A startup always starts from having a good idea and having the passion to want to give it life — that’s usually the all consuming passion right at the start, to validate what you think is a good idea in the real market, to see if people really buy or not. Ideation is pre-startup and you can fail, but you only start something when you have a good hunch that it’s going to succeed.

You always have to have your eyes trained on what’s key to success, not long-term success — you can’t do that — but at least your immediate success. You draw those lines in the sand then it helps you prioritise what you need to do. You’ve got to build in a fair bit of – some call it pragmatism, some call it laziness, because you can’t really do everything right in one shot. So if you put in a lens of a certain level of laziness as I would like to call it, then the real important stuff will float up.

At the early stages, what you think of is really viability and survivability. At the early stage, the few folks that you have are crucially important to you. So any time there’s a fear that you might lose someone, it means you can’t sleep for days and nights and you’re figuring out how, and it feels like if you can’t solve that, then everything goes to bits. I think in the later stages, you tend to past that because you have systems and processes, you have more people, there’s more redundancy, or maybe you just get used to dealing with things because that’s a truth in life, you you’re going to lose people and you also learn that sometimes it’s for the necessary good.

All founders have got to invest some money in their companies. How much depends on what you have. If it hurts, that’s good enough, because it’s all by having skin in the game rather than the quantum of it. Some may argue that time is money as well, that is true. Or opportunity cost is money as well. That is also true. But it’s got to be real. At the end of the day, you have to sleep well at night knowing that you have invested and you’re not just trying to be smart, or you have a fulltime job, you are doing this part time like, I invest my night time hours and it’s worth two million bucks. Bullshit.

One of the big lessons I learnt is the illusion of success or failure disguised as success. So for example, if you’ve already got a client, they will tend to want you to do everything. It’s just more convenient. And then you get stuck in it thinking that, oh I’ll just do this one and then I’ll be done, and the money is good. And you get addicted to it and at some point, it kills your product development because all your resources are ploughed into servicing. And then it rolls and rolls into a big gigantic ball, because the only way to step out of there is to mess up years of client relationships or worse, you start hiring resources just to fulfil that bit, so that you can concentrate on the main business. So things like that you’ve got to see it for what it is and take bitter pills from the start and say I’m not going to do it.

I believe the successful cofounder partnerships are like successful marriages. Coming from someone who’s only recently got married, I don’t know that much about what makes a successful marriage but I know it’s not perfect. Conversely I think the struggle for perfection is what kills a relationship. Any kind of relationship, for it to work and especially when you’re working towards something together, then it’s about recognising the strengths of each other and giving each other enough leeway to be weak and complement. You know, give some chance lah. You can’t pick on everything. And I think when you create that emotional debt between two or more people, hopefully that’s actually a more powerful tool to make someone improve themselves.

There were some seriously dark moments when I didn’t know when the next cheque is coming in. I think the first thing you rely on is yourself, which by extension is your family, and that was the first go-to I remember, and that’s painful. It’s actually coming out to the people whose opinion matters most, to say that look, I need help. I wouldn’t advocate that because I learned after that, when you know when you exhaust that, what’s the next thing? Actually your staff, the people who are behind you who are still with you, you will be surprised that they can go through the tough times with you.

There’s this certain level of positivity that’s needed, optimism, almost foolish optimism that you kind of need to power through these times. I found that to be true in a lot of startup founders. That doesn’t let you get too far down. Call it delusion, but you can persuade your own mind to believe that you know that good is coming, and you just soldier through it.

To stay productive, the most important thing is to try to stay happy. Because, you know, happiness just puts you in the right mindset to really find the right solution to things, and to stay happy is quite an art. I think I’ve done well through the years. I think to hone that ability to compartmentalise is immeasurable. I’ve seen a lot of people burn out or affect their family lives. That invariably comes back to haunt you, so it’s a vicious cycle. You have to cut that line very clearly. Sometimes even defend it stoutly and it’s easier said than done. Then you’ll be able to steer the course.

Prove some value and then use that value to sell through. The thing that’s confounded me quite often is, when the startup goes up, why founders are usually not organised in terms of their thoughts, to pitch value proposition. It seems so fairly obvious to me that I don’t understand why. I’ve made the same mistakes myself, when I first started off. It was quite hard hawking the internet to a whole bunch of people who’ve never heard of it. I realised that as I went through tons and tons of presentations that invariably just led to no business, but a lot of questions. I should have just sold them, you know, this is a new thing, pay me a thousand bucks an hour, I’ll tell you about it. That’s the value prop there.

I always advise entrepreneurs starting out to think about their life. You start off thinking oh, I’m going to do this, I’m going to give my heart and soul, and all of my life, but it is not true. You’re going to have to go through life like a normal person, you’d want to maybe settle down, you might want to have kids. Your parents are going to grow old, etc etc. So that’s a normal life and you have to really think about it to sync it up. Because I’ve seen enough founders who are brought to their knees because of family needs. And then when you fall out of that game, seldom you fall out on a high. Just break it up into phases, cater for that. You’ll know how many throws of the dice you have. And then you optimise for that.

If there’s anyone who knows how to start companies, it’s serial entrepreneur Ben Tan, co-founder of Tin Men Capital. Ben started his first internet company in 1995 while still in university, and got hooked. In all, he’s started and sold three companies, incubated many more, and been an angel investor in others. Take away tips from the 26-year veteran for startup success: from how to prioritise, pitching the right pitch, to thinking about life before taking the big leap.


The Emotional Journey of Creating Anything Great

Ben’s profile: LinkedIn

Episode transcript: Download

Ben’s chosen charity: Ben recommends making donations in cash and kind to needy people one knows personally. Alternatively, listeners may want 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.


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