The Hardest Thing About Doing a Startup

Haven’t we all heard of very smart, and very accomplished friends/ colleagues of ours who tell us how they are so ready to start their own business, but somehow they never do? One thing I learned early in my career is this — The Hardest Thing about doing a Startup is, well, Starting Up!

Here are some of the reasons why I think it is such a hard thing to do:

The N+1 Syndrome

I have found the ‘N+1 Syndrome’ to be the most common reason, especially among accomplished professionals who are doing well in their current gig. The thinking goes like this:

You are earning well, you have a good name at work, your families are comfortable, and most importantly, you get that nice paycheck at the end of the month! Yes, you have this exciting idea, the thought of not reporting to a stupid boss is enticing, the lure of hitting that IPO jackpot, becoming famous, and retiring by the time you are 40 is tantalizing! You are going to do it, yes! No-one is better qualified! You will just get this one little thing out of the way, and then you are set!

Most even have excellent ideas for the new business, but somehow they keep moving the start date forward by a year, then another year, and another.

This is the N+1 syndrome. It’s always ‘Just One More Thing’! Everyone of us is susceptible to this — we feel we just need one more year, one more $100K in the bank, one more thing taken care of at home or work, and then we will be all set to take the plunge. Often times, this remains a moving line, and I have found that the only way to overcome this is to take a deep breath and plunge in!

The De-Risking Myth

There are times when you feel you are ready. You have this awesome idea, and you know it is going to work. But you figure,

“Why do I have to quit and take all the risk of giving up what I am doing now to start on this new thing? The smart thing to do is to implement the new idea on the side, and once it picks up momentum, I can easily quit what I am doing and jump onto the new business!”

This sounds rational alright, but in most cases, the side-business remains a side-business for a long time, and eventually you decide it is not as exciting as you thought, and it is better to just concentrate on your day job.

We ought to realize, and accept, that doing a startup is about taking a risk, and that is indeed part of the fun! Moreover, our chances of success are way higher when we know we are fully committed. I have often followed Sun Tzu’s famous advice to “burn your bridges behind you” so that the only option left is to forge ahead and succeed.

Yes… But How?

Often times, I find that people find it easiest to startup when this crucial decision to quit is taken off their hands — i.e, when they get fired from their job, or when they are finding it impossible to land a job. But then few people who want to startup are so lucky, and you surely can’t count on this!

What can you do in that case?

From having successfully done multiple startups myself, and having observed & advised several others, here, below, is some practical advice:

You Just Have to Accept That Starting Up is Going To Be An Irrational Decision

A startup is a leap into the unknown, whether you like it or not. You can do all the research and analysis you want about the idea, the market, timing, etc., but all of that rational thinking and preparation can never give you 100% comfort. When it happens, it will have to be a leap of faith! So, acknowledge it early on!

Don’t Wait for That Killer Idea

I know this is going to be different from most other advice you will get, but I think it is a big trap to wait for that one world-changing idea before you venture out. Don’t get me wrong. You do, indeed, need to have an idea that you are passionate about, that you feel is compelling enough for you to give up the comforts of your cushy job/lifestyle. But very very few billion-dollar success stories start off with the founder thinking they are going to be that large or that successful — not a Google, not a Facebook, not an Oracle.

Did you know that Larry Ellison started Oracle with a $1200 investment building software on contract for the CIA? He told the Smithsonian Institution:

“When I started Oracle, what I wanted to do was to create an environment where I would enjoy working. That was my primary goal. Sure, I wanted to make a living. I certainly never expected to become rich, certainly not this rich.”

Beware the Naysayers

When you are about to startup, be ready to have your resolve severely tested. I remember when I was about to do my first venture, how almost everyone I spoke with advised me against pursuing my ‘hare-brained’ idea. My parents were dead-against it. My boss thought I was insane to quit when I was doing so well at my job, and did his bit to plant a host of doubts in my head! My friends were left wondering how I could be so fool-hardy, given that they knew how precarious my financial situation was then!

It is very hard not to develop serious doubts at such a time. What if you fail? After all, the odds of success in a startup are so very small? Will this finish your career? Will you go bankrupt? Will you be seen as a loser/disaster among your social & professional circles?

But then, often, when the startup bug bites you, it is hard to shake it off. You get excited by your idea, and the opportunity and the freedom to create something new is exhilarating in itself. It’s also about having enough confidence in yourself that you will eventually figure out a way to succeed.

I remember thinking to myself then that there really was not much I had to lose, and I had everything to gain.

The Earlier You Start, the Better

In my opinion, if you have a desire to do a startup, it is best to do it as early in your career as you can. When you are young, you have very little personal responsibilities to worry about; you have the least amount to give up — in terms of money, position or power. You have very little to fear. I remember thinking “If it works out as I envisage, it will be great… if things don’t work out, I can always go back and get myself a job, not a big deal”!

It Helps To Have A Supportive Spouse

If I have to put my finger on the one thing that can most enable one to take the plunge, it is having the unconditional support of your spouse. It was this that gave me the courage to brave all the odds when I did. Not only did my wife encourage me to go pursue my dream, but she offered to hold one end up by bringing in her monthly paycheck while I went about rolling my dice.

A few years later, as my venture became successful, I encouraged and helped her to embark on her own entrepreneurial journey. We have continued to follow that pattern throughout our lives thus far! It’s like playing a doubles game — when one partner goes on the offense, the other plays defense. And vice-versa.

You WILL Find Your Way Once You have Plunged In

Time and again, I have found that the hardest step in the process is taking the plunge. Once you are into it, you will inevitably find your way. It is of course, going to be a huge test of your creativity, your drive, your knowledge, and all your capabilities. It is likely to be a lot harder than anything you have handled in your jobs. You will stumble, you will struggle, you will develop serious doubts en route, but, believe me, you WILL find your way.

You will find sources of help in terms of people & money that you didn’t even know existed. Especially in today’s environment, there are so many entrepreneur networks, incubators, accelerators, investor & support groups out there looking to help and back good startup ideas, you just have to go out and look.

You have to remember, though, that when you are out there, you are still mostly going to be on your own. You won’t have the infrastructure of a big company you were used to earlier; you won’t have the big-name visiting card that opens doors; you won’t have the support orgs who will handle all the operational tasks for you; and you may not have your executive assistant.

But I believe you will have so much fun doing the startup, and learn so much along the way, that you won’t ever want to go back to a regular job if you can help it!

Thanks to Govind Chandrasekhar, Krishnan Narayanan and Sam Swaminathan for help on this post.