Doug Dvorak's Blog


The Struggles and Triumphs of a Serial Entrepreneur

Being a serial entrepreneur is one of the most taxing career paths anyone can pursue. Don’t think for a second that owning and running multiple businesses at once is anything other than a stressful grind.

If you have more than one business, you know the plethora of challenges that can crop up at any given time. Any way you shake it … it’s a tough row to hoe!

That said, it’s a career choice that will keep you moving forward and feeling fulfilled and happy at the end of the day. Life as a serial entrepreneur includes many ups-and-downs and it’s important to know what those are and if they are worth it for you. Continue reading to learn more about the challenges and successes you may face as a serial entrepreneur:

Responsibilities and Do-ability

Running a single business is a tough task. Running several – with all the responsibilities that includes – is daunting to the enth degree. Most people in this situation hire a different CEO for each business and then simply monitor their progress. However, serial entrepreneurs are built differently, and they tend to try to run all of their businesses by themselves e.g., Elon Musk.

It can be done but it requires a tremendous amount of organization, endurance, and dedication. If you want to run each of these companies yourself and you’re willing to put in the time and energy, it can be done. Like anything else that feels overwhelming, you just need to take it one step at a time,

Activity and Time Management

With so many things going on at once for them, it may feel like you’re running around with your head backwards. There is always something to do and you’d always be busy with something. However, there is a level of excitement in being so busy and if you’re able to develop the time management skills necessary, you may have more time than you think.

This requires knowing what’s important, when to do what, and when they need to be done by. But if you do it correctly, there is a strong satisfaction and sense of accomplishment from getting the thing at the top of your list checked off.

Traveling and Mingling

With so many businesses and so many clients, you have the opportunity to meet many new people and see amazing sights around the world. In their travels, serial entrepreneurs frequently cross paths with other successful people, from clients of companies you want to work with, potential business partners, or those in a similar social group.

This can give you the opportunity to expand your knowledge, develop new contacts, and find motivation from other like-minded people. Additionally, it gives you the chance to see things and places that you’d otherwise wouldn’t. This can include cities, parks, museums, theaters, restaurants, all kinds of things.

Competition and Experience

As a business owner, you’re always going to be competing with other business owners, which can and will include other serial entrepreneurs. To be able to keep up and stay competitive, you’re going to have to learn to learn fast. Though that may sound intimidating, learning such skills will bring the benefit of gaining a lot of experience and knowledge quickly.

Staying competitive will force you to learn and will allow you to grow at an alarming rate. You’ll quickly know what to do in most situations and how to figure out the rest. Additionally, you’ll be able to discover the strengths to replicate, the weaknesses to avoid, and the unfilled niches of your competitors.

Failure And Confidence

The fear of everything that you’ve worked for being unsustainable and eventually falling apart is the most dreadful part of being a serial entrepreneur. It will almost always hang over you, even during the best times. Eventually, something will give way, whether it’s because you bit off more than you could chew or because of bad luck.

Failure is something that must be accepted. However, through defying the odds and being able to be successful despite the risk of failing, or even in spite of previous failures, you will develop a confidence that will keep you going. That confidence can be extremely rare and may be the main thing that keeps you going as a serial entrepreneur, the confidence that you can be successful despite overwhelming odds.


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