Don’t Start A Company Until You’ve Asked Yourself These Questions

For most startup founders, their key motivation is not the money or the fame of success in business. Rather, they are driven by a core desire to change something fundamental in the world. This, the need to make a difference, is what really separates the successful from those who fake it.

At the same time, the fear of failure looms large in the founder’s mind, lurking in the shadows at all times. Waking often in the middle of the night, either struck with inspiration or frozen in terror, the life of the entrepreneur is difficult for friends and family members with “real jobs” to understand.

But when it all comes together, when a new product or service is brought to market, when it fills a real need for a customer, and there is the excitement and exhilaration of growing demand, it all seems worthwhile. The founder doesn’t care about the launch parties, or the Tech Crunch articles, or the investor meetings. What they care about is realizing a vision of the world changed somehow, a positive impact on people’s lives as a direct outcome of her ceaseless and tireless efforts. That’s what it’s all about.

Usually, it takes several attempts to get there. Most entrepreneurs who are in a position to claim any modicum of success did not achieve it overnight. The history of success in entrepreneurship is paved with the crushed and broken dreams of countless half-baked and half-cocked adventures. One after another, these escapades were founded on wild-eyed enthusiasm, propelled by the legendary “reality distortion field” that is hard-wired into every startup founder, only to be dashed on the hard rock reality of fickle consumer tastes or grumpy enterprise intransigence.

I’ve personally been involved in 8 distinct startup adventures of one kind or another, either as a co-founder or an early risk-tolerant employee. Half resulted in smoking craters and buckets of wasted blood, sweat, and tears. The other half narrowly survived multiple catastrophes, resulting eventually in at least stable revenue and in one case a modest acquisition. In the last several years, with those experiences safely in the rear view, I developed a system that helps new ventures iterate through their biggest risks and secure at least a reasonable shot at success.

It starts with asking yourself a few very difficult questions. Only when you’re willing to really stare in the mirror and face your deepest fears head on will you be even remotely ready to start working on building your own company.

The first thing you need to ask yourself, then, is why are you doing this in the first place? Why leave your job? Why start a new company? What change do you want to see in the world as a result of your efforts? If your answer is anything less than a profound vision of major changes in the lives of a customer segment you deeply care about, my friend, you are wasting your time. Go back to that analyst gig at Goldman Sachs.

The second thing you need to ask yourself is who is your target customer and what is their biggest problem? How much data do you have to support your answer? How many of them have you already spoken to? Have you been able to sell them anything yet? If you’re not solving a real painful problem for a customer, you’re not likely to get very far at all.

The last thing you need to ask yourself, before you start your company, is what will you do when it doesn’t work out as you’d planned? Do you have a clear and specific threshold, like a specific amount of money you need to make by a specific date, that will have you either pivot or walk away if you don’t make it? The slippery road to madness is greased with “almost.” “I almost have enough money.” “We’re almost there.” “We almost have enough customers.” Almost only counts in horse shoes and hand-grenades. In startups, you need a hard line to kill, pivot, or continue.

Without a crystal clear vision of a future state of the world, one in which you have made a significant difference in people’s lives, you are destined to rotate around the merry-go-round of mediocrity, jumping from one hair-brained idea to another in search of validation from customers.

Do you feel ready to start on your startup adventure then? See how ready you really are by taking our free assessment.