Why it Takes 5 Years to Become an Entrepreneur

Summary:  Becoming an entrepreneur takes most people 3 or more startups and about 5 years because entrepreneurship isn’t about any particular idea or product – it is a career change.  But unlike most career changes the real lessons are from what we learn about ourselves.

Your first company will almost assuredly fail because you don’t even know what you don’t know. Thinking you now know everything, your second company will fail even worse – although probably faster. By your third company you’ll be scared s***less of failing again, will work harder than ever, will finally realize you don’t know anything – and you will succeed.

–paraphrase of a speech I heard from Mario Morino, 1999

This week’s Startup Edition question is, How do You Get a Job in Startups?1 I thought I’d talk a bit about what many people ask me in my Startup Help Calls:

How do I become an Entrepreneur?

It isn’t About an Idea, Product – or Even a Company – Entrepreneurship is a Lifestyle

And one that surely isn’t for everyone.

My advice is to think about entrepreneurship as a long-term career change – like becoming a lawyer, doctor, or pilot. And like any profession, it takes years to get new skills, relationships, and experience.

But unlike most career changes the barriers for becoming an entrepreneur are practically 0. Quit your job and call yourself a doctor and you’ll be labeled a crackpot. Quit your job and start a company and colleagues and friends will call you and entrepreneur.

When I reflect on my experiences of the past 15 years and those I’ve shared with startup friends like Patrick Smith, I’m struck by the wisdom of Mario Marino’s advice in the quote above. It seems to take people about 5 years and 3 startups before they start achieving success.

Those that do it faster definitely do exist, but they are the outliers – I certainly have not been one of them.

Are YOU Ready to Make Entrepreneurship a Career? Ask Yourself this Question

Imagine that you’re about to quit your day job to start a company on an idea you just can’t get out of your head. Ask yourself this question:

What will you do if your startup fails?

Will you go back and get job? Is this outcome too terrifying to imagine? Or will you start working on the next startup?

There is no right or wrong answer, but HOW YOU THINK about the answer will tell you whether or not you’re viewing your startup opportunistically – that is, a way to achieve some short-term goal – or as a career change.

Your odds of success will go up dramatically if you plan for 5 years of training.

There is So Much to Learn – Mostly About Ourselves

In the last few years the number of books, blogs, events and startup programs has exploded – and yet people are just as confused as they were 15 years ago when none of this stuff existed.

You’re overwhelmed by all of this information because it doesn’t tell you what you REALLY need to know – about you.

What are you really, truly, interested in? Who do you want to work for? What hard skills do you need that you don’t have? What key relationships do you need that you don’t have? How resilient can you be when the alternative is failure?

These answers are what you really want to know – and you’ll only find them by working hard, failing, and trying again for years.

Photo Credit: Ewan Cross via Compfight cc

  1. If you haven’t subscribed to SE yet, do it – you’re missing out on some great content. What I enjoy most about reading and writing for SE is seeing not only the different perspectives of the authors, but also how differently they interpret Ryan’s weekly question.


  1. Mladen September 16, 2013 at 3:25 pm #

    Great post again, Kevin. We only read about the stories of the great startups. I failed my first startup, even though I thought it was special. Founding the own company not always rainbows and sunshine! We should read more posts like this.
    Regards from Cologne.

    • kevindewalt September 16, 2013 at 9:53 pm #

      I have no doubt that you’ll get there Mladen – just a matter of time.

      • Mladen September 17, 2013 at 2:42 am #

        Thanks Kevin!

  2. Hugo Castro September 17, 2013 at 6:38 am #

    1st startup – left after one year
    2nd startup – failed BIG (I thought I knew everything)
    3rd startup – failed (we didn’t know what we were doing)
    4th startup – ??

    But the most valuable lessons are about me. I tend to know what I’m going to think in advance or going to react in certain situations. I react more easily when starting to procrastinate and get back on track faster.
    Not sure if I would achieve this working on the corporate side.

    Thanks for another great post Kevin! Got to catch up one of these days.

    • kevindewalt September 17, 2013 at 6:52 am #

      That’s awesome, Hugo. Let’s definitely catch up. You’re totally right…now that you’ve been through the lessons a few times you’re getting great instinct.

      You’re getting better at recognizing patterns knowing what will happen – because you’ve seen them before.

  3. Hayk October 2, 2013 at 4:11 am #

    Nailed it!

    People only see the rosy part of entrepreneurs, their successes and think it is surefire way to success. They don’t realize for every one successful entrepreneur there are ten who fail, many of them not to pick themselves up again.

    I blog about failures and documented my own personal and entrepreneurial failures. Entrepreneurs have to be open about their failures, something that is taboo in most of developing world cultures, hence the reason forso few of African and Asian true and big successes.

    On my side , I started what was in 2009 the first coworking community space in Egypt and MENA region, only to flop in 9 months. We picked notapime location and my cofounder wasn’t as committed in action as in words. Usual story.

    My second enterprise, while perhaps still abletoturnaround get it’s own legs, is in stalemate and I my ring to find a buyer for it. It’s a health forum in Mozambique.

    My third one, kartag.com, is the first social carpooling app in Egypt , launched in May 2013, currently scaling up with all implied growth pangs. Fourth one is a food ordering app about to be launched.

    So yeah entrepreneurship is a mentality, DNA and lifestyle.

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