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How to be a successful, serial entrepreneur

By Jim Connolly | August 27, 2021

Wherever you are right now, whatever your past, you can be a successful entrepreneur or serial entrepreneur.

First, let’s get the serial entrepreneur myth out of the way

Look around any business network and it won’t be long before you find people, calling themselves serial entrepreneurs.

They’re everywhere. Or so it appears. However, as is often the case, all is not what it seems. In fact, 99.9% of the people I see calling themselves serial entrepreneurs… are not.

They aren’t even entrepreneurs.

They are serial starters!

Allow me to explain.

Serial entrepreneurs or serial starters?

Serial entrepreneurs: These rare people build a series of successful businesses and fully realise the potential of each business, before they move on. A well known example is serial entrepreneur Ev Williams. Ev founded Blogger and sold it to Google for millions, then he co-founded Twitter and then, the hugely successful Medium.

Serial starters: These are the people we see everywhere, who start a series of enterprises, yet never successfully finish developing any of them. They lack the commitment shown by entrepreneurs. So when the going gets tough, they get demotivated and quit. The vast majority of self-proclaimed serial entrepreneurs fit in this enormous group.

This begs the question.

Why are serial starters so common?

It’s extremely easy to start a new venture. It’s exciting. It brings motivation with it. It gets them up early in the mornings and keeps them up late at night. Everything is new. A blank slate. A new beginning. Endless possibilities.

Then, after a while, the real work begins. Not the new enterprise, shiny work. The real nitty-gritty work:

  • The sales calls.
  • The rejections.
  • The unreturned mail.
  • The broken promises from those who said they would help.
  • The cash flow problems.
  • The hard knocks.

As the shine wears off, the momentum drops for the serial starters. So, they look for the next big thing, rather than finishing what they started. The cycle repeats unless they summon the grit to make it to the finish line.

More about grit than money

You don’t need to start of rich, to be an entrepreneur or serial entrepreneur. You do need grit though.

Yes, some entrepreneurs, such as Gary Vaynerchuk, inherit a multi-million dollar business from their parents, and can use that wealth to get all the additional investment they need and branch into other enterprises. However, most of us start off with little more than an idea, grit and commitment.

Ev Williams, who I mentioned earlier, is a textbook example of starting without money. Like most entrepreneurs, he had to do it the hard way. No wealthy parents. No million dollar assets. No easy way to access the financial investment he needed.

Ev was so broke when he started Blogger that he was living on a friend’s couch! He’s now worth hundreds of millions of dollars. Read Ev’s inspirational story and watch the video, here.

History shows us that when it comes to business, money is less important than grit. Remember, Steve Jobs came from a blue collar family! The key is to decide what you want and then commit to doing what’s required, to make it happen.

It’s that simple. And that hard.

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Hi! I'm Jim Connolly and I help small business owners to increase sales, boost their profits and build amazing businesses. Read more here.

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