Serial Entrepreneurship: Thoughts and Lessons

Updated: September 26, 2022

When I meet people for the first time and tell them that I’m a businessman, their usual response would be the question, “What’s your business?”

And my answer would automatically be, “I have an internet cafe.”

But did you know that that was not always my reply?

Before, I’d answer “I have several,” then I’d give them a rundown of my entrepreneurial ventures. An internet cafe, an eLoad station, a photocopying kiosk, among others.

Until I realized that my “old answer” arrived as somehow contemptuous. That’s because it does not fit the common notion that a person usually has just one business.

And that’s why I decided to change my old response and simply say I have an I.T. company; and consequently avoid giving the wrong arrogant impression.

But it does raise a question in my mind, why is serial entrepreneurship not a widely accepted idea?

I believe that most people want to start their own business, become their own boss.

And that usually means building a successful venture that will become a big company someday. One that has several branches and even franchisers, catering to thousands (or millions) of customers.

However, the idea of putting up several small-scale businesses is not a common dream. It is quite surprising given the relative ease (at least in my opinion) at which you can accomplish this.

What exactly do I mean? Well, let me go back to the time when I first decided to put up that internet cafe of mine.

After almost a year, I saw that the business was doing quite well. Many urged that I should expand – add more units, start offering more services, and even consider opening a second branch.

At first, I did try to expand the business, and I must say it was exciting to see your “baby become a child”. But along the way, I found myself… for lack of a better term – bored.

Don’t get me wrong, I loved working on the business, and still does. But deep inside me, I wanted a challenge – and expanding the business was not the answer.

Then came the idea of starting a completely new business. Nothing really big, just something that would give me enough “adrenalin”.

And that’s how it started…

After the eLoad station, the photocopying kiosk came. Then the school supplies store and many other one-employee businesses – and that’s how my serial entrepreneurship began.

Lessons in Serial Entrepreneurship

During all these years of starting (and also closing down) several businesses, I’ve learned some valuable lessons. Here are some that I’ve learned about serial entrepreneurship:

  • Opening a business gets easier and faster every time you start a new one. All the mistakes you’ve made in the past are usually prevented and you eventually learn and get used to the bureaucracy of registering a business.
  • Small businesses, although it gives little profits, are easier to manage – there’s less paperwork and usually just one employee to handle. Consequently, if it does not take off well, it’s also less painful to close down.
  • Being a serial entrepreneur forces you to automate your businesses – to make your business run without you – which is actually a good thing for it veers you away from the trap of self-employment.
  • Having several businesses lets you enjoy multiple sources of income. And when the market of a specific business declines, there’s less worry that your finances will be affected and you have more courage to simply close down (or sell) and start a new and more profitable one.

To end, please understand that I’m not writing this to convince you to become a serial entrepreneur. It’s a cup of tea that you should decide for yourself – call it simply an option you can consider.

But take the lesson that serial entrepreneurs are people that do not shy away from failure, that’s why they become successful.

And If you have to take anything from this post, let it be the fact that when it comes to entrepreneurship – all you can really do is to try your best, knowing that trying leads to learning, and learning eventually leads to success.

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  1. I guess I’m a serial entrepreneur then.

    I want to add that there is a very different generation today especially in the way people do business. Today, one can build a business just by building up a website and putting valuable (or not) earn from numerous direct ways like PPC and CPM. Freelancers (It’s a business) have also boomed in the past few years because of the internet. Gigs as we call it even earn more than some office jobs.

    We, serial entrepreneurs, try to earn more by simply creating more streams of income, which means creation of more small-scale business of our own.

  2. Hi

    hi i have too a internet cafe i also get same situations like yours going serial, and terms expansions. Expanding is kinda boring no challenge and not much in profit increase. I have a manager who handles the shop in meantime i am attending seminars and fairs (i also attended pinoynegosyo in SM mall of asia, lot of high schooll students) they look at me why i am not looking or fully focus in my shop… well like you i dont want to be trapped in self employment

    More power, and lot of days i was anticipating your emails articles but i think you were busy because this is your latest from last 2 weeks?


  3. Hi Allan, yeah I’ve been busy with offline ventures. It’s my goal to put up a new business by the end of the year or early next year. Thanks for taking the time to comment. 😀

  4. […] And lastly, remember that learning doesn’t stop when you graduate from college – so continue studying. Learn about the stock market, I know you’ll enjoy that. Buy a book about entrepreneurship, because that will eventually become your passion. […]

  5. i love this post because it gave me the encouragement i needed just when I am feeling unsure of myself. i’ve been beating myself to concentrate on just my foodcart business which i am getting bored of to be honest. but for some reason other business opportunities are coming my way. reading this just gave me the right push to follow my gut feeling. tnx sir Fitz!

  6. […] And lastly, remember that learning doesn’t stop when you graduate from college – so continue studying. Learn about the stock market, I know you’ll enjoy that. Buy a book about entrepreneurship, because that will eventually become your passion. […]

  7. Mr Fitz, your post truly hits home with me in several ways, especially the opening account you shared of talking to others about your business. In the US we have a saying, “”it takes one to know one.” A business person would appreciate your telling them of your list of activities and may well enjoy some time with you to ask your advise about something they are planning. The non-business person, as you point out. may see arrogance. In my six years + here in the Philippines, I have been truly impressed with the wide variety of both small and medium sized business that we have watched from inception and on into the growth stage. My gas delivery service is one that really stands out in my mind. The owner is an expert not only of how to service a customer but he can and does do a wide variety of commercial installations for restaurants and other establishments. What most folks do not know, is that this family run business also had several other small enterprises that supported them as their gas service grew to the success that it is today. At a nighttime wet market, they took delivery of and sold vegetables as well as other means to earn. Recently, they sent a kid off to a prestigious university here in the Philippines! The owner and his wife did as we say in the US, “they pulled themselves up by their own boot straps.” These folks are as nice as you could ever hope to meet and they are what I would consider a TRUE PHILIPPINE SUCCESS STORY.

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