Start Arrogant, Get Humble Fast

The one big lesson from my startup experience

I was going to put an F1 image but this is really more apt. Via Unsplash

In my experience, a startup is like a car race. The beginning is a straightaway and your choice isn’t that complicated. Just hit the gas. Maybe the wheels will fall off or somebody will crash into you but in terms of your decision making it doesn’t really matter. You just have to go. You have to be single-minded, determined and, in my experience, a bit arrogant.

Almost immediately, however, you start running into corners. If you don’t master the brakes you’ll hit a wall really fast. You have to learn how to listen to the market, your team and a board if you’re going to survive.

It’s a constant balance — the gas and the brake, aggression and humility. I don’t claim to have mastered it all, but that’s been the one thing I feel like I’ve learned, after seven years. You have to start arrogant and get humble fast.

Start Arrogant

At the beginning, I went to an investor pitch in shorts because it was hot. Apparently people talked about that for years, and that round of investors passed on me. I think the general impression was that I was arrogant. They were right.

But how else do you do it?

If you listen to everybody you’ll just delay or just not do anything. If you follow all the rules¹ you’re not doing something new. Sometimes you just have to be arrogant, be different, and press ahead.

The fact is that a truly original idea often sounds the same as a really stupid idea and there isn’t a great way to tell them apart. Investors just have money, they’re not smarter than anyone else, and they can’t tell you. No one can tell you. The only judge that matters is the market, and for that you need to just get out there.

The other fact is that even a great idea may not be great for you, and again only the market will tell you if you and your team can execute.

At some point, you have to just get out there and see. This is by no means a guarantee of success, and this arrogance can be the very thing that gets you killed in the long run, but I just don’t know how else to do it. You have to believe and take that leap into faith.

Get Humble Fast

The initial idea for YAMU (my startup) was a cab app, which is somewhat fitting because we were acquired by a successful cab app in the end (PickMe). I was quite arrogant about that idea, and quite wrong.

We pitched for a cab app and built most of technology for it. We even had a working unit in a cab but then our tester blew the data connection watching porn. In order to market this upcoming technology we started a city guide (because where does a cab take you?) and that’s what actually took off, but it took me over a year to acknowledge that we had, indeed, pivoted.

The market was clearly telling me that me and my team were not the people to execute a cab app, but I wasn’t humble enough to listen. If I had been I could have changed the team or just re-focused the company, but I wasn’t. That was the first corner we encountered and, due to continued arrogance, I just drove into it.

Luckily the market carried us along. Sri Lankans like food, and our section on restaurant reviews took off. We were growing 10% a week for months, and we’re having a growth spurt again, growing 10% month-on-month now, post-acquisition. Revenue is another thing, but we did find growth.

Throughout all of this, we never constituted an actually active board, having only advisers, and I only started really involving staff at a high level very late in the game. Basically the lesson about humility I learned too late and we only exited because we got lucky. Basically we took corners by slamming into them and getting dragged along the inevitable contours of the wall. I wouldn’t do this again.

At the beginning, I thought it was all about the idea and me, but it’s not at all.

Making an idea into a company is really about getting it outside of you. And that’s really about people. Other people. If your idea is a cab company but people like your food reviews, you need to do that. If you find someone that sees the world the same way as you, you need to follow them for years until they join your team, which I’ve done. And then you have to leave them alone to make decisions.

You have to have your idea and you have to be crazy about that, but then you have to get it out of you, you have to get it into the market and into your team, and then you honestly have to let it go.

That letting it go part is the hardest because you have to burn the bridge that got you pretty far, but you have to do it. Any founder that can’t adapt from initial zealotry to more sober management is usually bound to fail or get fired. As these are the default states anyway, you shouldn’t rush the process.

Did I do it this way? No. Not until the very end. But it is a painful lesson that I think I’ve learned.

Working The Gas And Brake

This is why I think the average age of a high-growth founder is 45. I started at 30 and I was frankly stupid and made a lot of pointless mistakes. Yes I was arrogant enough to ignore a bunch of naysayers, but I never really figured out the brakes. We exited, but basically as an engine on rims. I would not call myself a good driver, in my first run.

But I do feel like I learned something. I’ve felt that emotional connection to an idea that powered me through years of hard work and occasional suck. I’ve felt the pain that caused me to become more humble and to begin listening to and relying on other people more. And I think I have a vague sense of how to put that together better in the future.

Can a Medium post communicate that experience to you? I don’t know. I really don’t know. When I was starting out I wouldn’t listen to anybody, and I had to learn for myself. So I assume you’ll go your own way as well. This is just my experience, and how I’ve processed it. The one lesson I’ve learned from 7 years is this. Start arrogant and get humble fast.

⁰ This is adapted from a panel discussion I sat on at the CIMA Business Leaders’ Summit, 2019, in Colombo.

¹ I do not mean ethical and legal rules. People use arrogance to justify a lot of horrid human behavior, and I don’t agree with this. I just mean pursuing an idea in the face of common market or business wisdom.