5 Secrets of Successful Serial Entrepreneurs

By Michael Baker , Apr 14 2020
Serial Entrepreneurs

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What exactly does the term ‘serial entrepreneur’ mean? Is it any different from a typical entrepreneur? To begin with, a serial entrepreneur is an entrepreneur who comes up with a pool of ideas one after another, unlike a typical one who strives on a single startup venture. Quite apparently, serial entrepreneurs are not very common in business world, perhaps owing to the fact that flourishing a single business, let alone more than one, is not an easy work at all.

It takes years and decades for some entrepreneurs to establish a business crossing the $1M mark. It takes another five years for an entrepreneur to challenge himself again and step out of the comforts of a well-built business, thereby treading into the cold waters of becoming a serial entrepreneur. Yet people take on the risk.

Serial entrepreneurs might be a rare species but they sure climb up to the top 5 billionaires of the world really soon.

Feeling curious enough to know their recipe of success?

We have compiled the secrets, a few if not all, that will tell us what and how exactly a typical person slash entrepreneur can be transformed into a serial one.

1) Managing Time

Managing Time
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We get lots of advices on management of time and how to go about completing tasks.

We may listen to a bunch but we happen to remember a few, and perhaps try to follow only one. From a personal point of view, I believe the only proven advice in terms of time management is to not attempt at multi-tasking.

Founder of Smart Bear and the co-founder of ITWatchdogs, Jason, is a famous serial entrepreneur who speaks on how to supervise time or to go about completing your tasks. He says that the only advice he chose to follow during his struggling time was to do one task at a time. We have a misconception going around us that multi-tasking is sign of efficiency, and it is dangerously wrong when it comes to entrepreneurship. When building a business, doing more than one work in one hour is plainly unproductive.

Explore: What Kind of Entrepreneur Are You?

2) Working In A Group Of Partners

Working In A Group Of Partners
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We do not always get a graduating degree in the field that we love, neither it is necessary that we establish a career in the areas that interest us. Sometimes, a graduate in law or journalism take their entrepreneurship venture into, perhaps, the property management or the cooking industry. Building a business is a choice, taking into account several factors such as the distant future, demands, potential for profit and etcetera.

The next important secret behind successful serial millennial entrepreneurs is to take help when it is offered.  Even if it is not offered (which is mostly the case), you have to employ or partner with people who will help you grow. Despite having sound basic knowledge of the business you are kick-starting, you cannot solely depend on your own capabilities to fund your business either way. When working on to launching a company, find the right people to partner with or hire such employees. Look around somebody who is doing the same work, maybe on a smaller scale. A friend or an associate perhaps, having an experience of more than a couple of years in the same realm. Your set of knowledge and their set of skills will cater to the growth of the venture in the correct manner.

3) Do Not Compromise On Uniqueness

Do Not Compromise On Uniqueness
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You and I both know the importance of this point. In order to become a successful “typical” entrepreneur, let alone a serial one, you need to make a very distinct impression with your products in the market. The pressure on a serial entrepreneur is the prospect of coming up with unique ideas one after the other, which is where the line is stretched between the either types.

The thing to remember here is that nobody owns your ideas; you alone are the owner and the creator of them. However, there is no doubt in saying that a serial entrepreneur has to face the challenge of divided focus because he is working on not one but more than one business ventures, simultaneously or not. Your primary aim must be to come up with ideas that are worth to work over, but strictly not too similar to an already existing product in the market.

4) Develop A Thick Skin

Develop A Thick Skin
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A serial entrepreneur has to face failures more than anybody else. It doesn’t matter. If you are striving to become a serial entrepreneur, you should better prepare yourself to have 5 on 10 failures at the beginning of your time. The key is to not let it bother you and let it not overpower your ambitions. Failures can be intimidating; true, but for a serial entrepreneur, there is really no space for being intimidated.

Call it a secret or a plain advice; do not let your failures jostle some of your successes.

If you let that happen, you’re doomed. Not all of your ideas are going to make 7 or 8 or even 6 figures. Some of them are going to revolve around 4 or 5 figures for years, and you have to simply accept that their time is over. Move on to the next venture you have up your sleeve. One day or another, it is going to tick.

Explore: Bid Farewell to Startup Fear

5) Delegate Your Work

Delegate Your Work
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An entrepreneur often finds it difficult to transfer the control of his/her business to another person. This is where most of them let go of the chance to become a serial one because they are too possessive of their business to let it go in other hands, however safe they might be. Do not commit this mistake. If you really want to turn yourself into a successful serial entrepreneur, encourage the ideas forming in your head by delegating your existing work.

A successful businessman knows how to delegate his tasks to skilled employees in order to develop and work on other ideas. The key here is to learn to trust people around you and to give them a chance, under your supervision nonetheless. Naturally, you need a system that gives you space to implement new strategies and brainstorm new ideas. Delegation might require hiring more and more workers, which in turn means putting your profits into salaries but that is a sacrifice today which is going to double the investments tomorrow.


For serial entrepreneurs, ideas to develop into an enterprise are like their babies. You grow them from scratch to the point where they start to return your investments, and then you direct your focus and energy towards the next baby (read: venture) in line. Therefore, like a responsible parent, supervise your ventures but let them go free. Trust, strength and the willpower to keep growing is what you are going to need at all times.

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Market research nerd with a penchant for graphic design and branding. A digital marketer by profession; a creature of the web by compulsion.


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