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You win or you learn — 10 years, 10 startup learnings

Praveen Rajaretnam
3rd Feb 2017
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It’s been 10 years since I started my professional career — 10 years since I became involved with startups, first as an employee at a startup that was acquired and then having started up myself.

I’m glad I did take the jump. It’s been an incredible ride thus far with many new, interesting experiences, and I’m thankful to everyone who believed in my abilities and provided me with the opportunity to learn.

Credit: Shutterstock

While I continue my startup journey, I reflect on my learnings from the last decade in the form of takeaways, so others can benefit from my successes and failures in equal measure.

1. On funding

If founders aren’t thinking about the product, they are surely, most definitely, thinking about funding.

In the early days, I often talked about the struggle to get funded to anyone willing to listen. I complained about money, or rather the lack of it. The idea that funding is a prerequisite for startup success had been rooted deeply in my mind. In retrospect, it wasn’t surprising at all. The media glamourised funding news, instead of startups’ performance. It was all about funding amount, valuations, and unicorns. I was young and impressionable. I fell for it.

The truth is that the events and circumstances that lead to funding never appear just like that. You have to create them yourself!

Here’s what I’ve learnt. At the end of the day, if you want to create a product or a service, just do it. Start up. And if you want a lot of people to use it, focus on making it useful and likeable. The money will follow (if needed).

Also, money has always had certain undesirable qualities… It’s dumb. It lacks creativity. It’s also timid, slow, and extremely conventional. So, lack of investor dollars means an opportunity to be quick, creative, and courageous.

Read: Playing Moneyball with Startups — The Metrics Dilemma

2. On competition

I used to moan about how the competition raised funding despite not being first, having copied our model, with an inferior product, and how they were using that money to beat us.

I couldn’t have been more wrong.

It’s quite logical to think that if your competitors have more money, better talent, and more experience, they cannot be usurped — that they would be number one. But, time and again, history has shattered that notion (Google, Facebook, Dropbox).

You can beat the Goliath with a better product, a better service, and superior execution.

So what your competition does should be the least of your concerns. If anything, investors like competition. It validates your product and business model, making your startup a more exciting bet.

You should know what you need to do to make your product better and make your customers happy. But you can’t possibly know what you need to do in order to get to your competitor.

Focus on what you can control and what’s in your control. Everything else is a distraction.

A quick tip

Your competition is most vulnerable when raising funds. They are caught up in customary paperwork and their priorities lie elsewhere. Their focus is away from the product and users. The entire process is exhausting. And more time is lost in celebrating the funding milestone. All of this makes them susceptible. They become complacent. So, if you get whiff of such news, instead of being bogged down, pull up your socks and get to work!

Having said that, also be prepared to grind it out. Your rivals will outspend you by 10X for a considerable period.

3. On work ethic

I used to think working longer meant working harder. Perhaps even working better.

I was wrong again.

I realise it’s not important for me or for my team to work more than everyone else. It’s only important that we only do whatever we do being completely focused on the job. It’s a must to give it your full attention because I believe it makes the difference even if you give it only four hours. It doesn’t matter if someone worked for 14 straight hours — if they didn’t put in their 100 percent, the outcome is always going to be second-rate. When that happens, I tend to ask, “Don’t you like your job?” Champions don’t win Grand Slams or Olympic medals with that attitude.

While a startup is always on full throttle, it doesn’t mean you can’t take a power nap at work, or go on vacations. By all means, do it and encourage your employees to do it. But make sure whatever you do, you give it everything you have got. That doesn’t mean you will surely get what you want, but if you give it your all and work harder, perhaps you can get something. That’s very important.

Read: 8 Ways to Hiring Right for Your Startup

4. On starting up

"What made you start up?"

It’s one question I’ve heard so many times over the years.

For most of us, it starts with a pain point we want fixed. Or perhaps we are unhappy with an existing solution and believe it could be bettered. Maybe we deeply care or are so passionate about something that we give up our cushy day jobs and start up for the pure joy of it.

Whatever it is, make sure you start up for the right reasons.

Don’t start up because you want to "start up" or be called the CEO. Don’t start up because everyone around you is doing it. Don’t start up thinking of selling out in two years. And don’t be the guy who quits his job first, then looks for ideas to start up. I’ve rarely come across entrepreneurs who have found success this way.

5. On running a startup

Once the honeymoon phase is over and investor dollars are in, you wish someone had told you that running the startup only becomes progressively harder. That’s because you realise that you need to run the company first before you think about your brand or product. Looking for new office space, hiring more personnel, filing regulatory papers, legal compliance… the list is endless.

You could be forgiven if you thought that money, like jazz, makes things easier. But, it’s actually more hard rock, more metal, than anything else you know. It going to be really loud and you better start liking it as it will be a while before the decibel levels come down.

6. On letting go

When I started up, as a founder, I did all the jobs myself — I was the marketer, the biz-dev guy, and the office boy. It was the best way to learn and you find that there’s ample time to educate yourself — there’s no one else to do your job! I learnt everything from scratch and it was wonderful.

As Elon Musk said,

“When you want something done, do it yourself.”

It works so long as the company doesn’t grow faster than you can handle all by yourself.

Unfortunately, post funding, growth speed is exactly what your investors demand, and rightfully so. That’s when you have got to learn to trust other people who will do the job you are doing yourself. You find it difficult to let go of many functions as most founders, by nature, are borderline control freaks with a penchant for perfectionism.

It takes a while to realise that you need to put together a team, a very experienced group, who are very hungry to learn, and more importantly, work together with them.

In the initial days after you have set up the team, you will need to communicate a lot — very little work gets done during this time and it might be frustrating for you. But you will soon find that talking to your team is the best lesson you can get in a day — to speak to smart people about things they know much more about than you do.

As a founder, you want make sure you have put together a great team not just at the office, but off the workplace too. When you create an atmosphere like that you get the best qualities of everybody in the team. You should be able to trust your team and for the team to be able to trust you. When there are problems, everyone in the team needs to understand that they need to solve them together.

7. On tough times

The hardest part as a founder is knowing what you want.

I can’t tell you the number of times I didn’t know what we were doing. Worse, I had very little understanding of what I was doing or had to do.

Nothing seems to be working. You haven’t yet found the product-market fit and your savings are almost depleted. You start getting on each other’s nerves and sometimes you feel like you can’t even have a normal conversation with your own co-founder. It really makes you think, “Is this over? Is this it?” After all, it’s almost inconceivable that any two people always see eye to eye on everything. And it makes sense because there’s so much at stake.

You always have to find a point where you can start. It’s always possible to improve together, and thus possible to achieve great things. So when the sunny days arrive, you are prepared to make the most of it.

8. On founder attitude

Not only do we like a challenge but we relish being the underdogs. We want to be put in a position where we go up against the incumbent giant. It’s what drives us. It’s what inspires us.

We want to be the Rebel Alliance to Amazon’s Death Star. We want to make the weapon that destroys Uber’s Bazooka. Who wouldn’t? Turns out, not many. An entrepreneur however, will believe his pepper spray can take down the guy with the bazooka. Don’t ever doubt it.

Be ambitious. Be a dreamer.

9. On your defining style

David Fincher once remarked that Martin Scorsese told him,

“The things you do poorly are as much a part of your style as the things you do well…”
which was totally true, and oddly reassuring.

Many founders think they can learn how to build a team from other successful founders and startups.

There were many instances when we considered whether to implement a policy or introducing a system that was popular at another office. But almost always we decided against it.

I’d say, copy as little as possible — if you want to keep growing as a founder. You shouldn’t define the work culture at your company by copying how other startups do it. It just doesn’t work. Your employees are different, your goals and mission are different, and, most definitely, your product is distinct. All of that defines your company and its personality. In order to get that right, you have to feel it for yourself. You cannot grow by watching how others do it.

That doesn’t mean you shouldn’t broaden your horizons. It’s useful to learn and adopt good practices from others. Just don’t do it blindly.

Social skills

Remember that the most important skill you could possess as a leader is social —empathy in particular.

You could be the best coder or best sales guy in your company, but if you don’t know how to deal with people, you are likely to fail. You need a decent combination of both for your startup to find success.

10. On becoming complacent

As I mentioned before, money makes you complacent.

It doesn’t matter if a local startup has been number one for years. It will not help tomorrow when an international giant decides to up its game or enter the market with more money than Fort Knox. They are nothing more than mere statistics. It is just a mention on the company’s Wikipedia history and so it’s not an advantage.

Always remind yourself why you started up in the first place. The mission. Stay true to it and don’t waste the opportunity and the trust placed in you.

Parting thoughts

You win or you learn.

But, sometimes, when things don’t work out, you aren’t quite sure what went wrong. It becomes apparent much, much later. It takes time. It takes conscious effort to actually evaluate and understand what the learnings were. They don’t always reveal themselves so easily.

Also remember, as a founder, you have a lot of power, but even more than that, you have all the responsibility. And that responsibility never ends, even if you decide to move on from your startup — whatever may be the reason. Have such an impact that you are measured by your work even after you have gone. And should you leave at some point, as I did, make sure your left a positive mark at the startup you founded.

Founders in many ways are incurable romantics. We have this desire to make the world a better place. So while success is important, I believe it’s far more rewarding to look back in 10 or 20 years and think of the wonderful times starting up. The early stages followed by the growth phase is a defining period, filled with personal development, marked by many learnings and hard work. A lot of people I worked with in the last decade are already managers and VPs at large corporate firms or CEOs at their own startups.

As Liverpool FC’s affable manager, Jurgen Klopp, said,

When you deal with things in life in the right way, then you can draw energy from them.

So, be thankful for the opportunity and enjoy the challenge.

Let's connect. I'm on Twitter and LinkedIn.

(Disclaimer: The views and opinions expressed in this article are those of the author and do not necessarily reflect the views of YourStory.)

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