5 Life Lessons from a Serial Entrepreneur


My work experience has traversed several industries: finance, sales, research, human resources, food retail, and finally outsourcing. I started working in 1991, but I did not become an entrepreneur until 2006. It was a small business; I owned and operated an automatic cell phone loading machine in Makati. It was not rewarding financially but I finally experienced what it was like to be in control of my own enterprise. And I loved it!

Two years later, I co-founded an outsourcing company that operated profitably for four years. I thought I had it made until a phone call in 2012 changed my life forever.

Life as an entrepreneur is never easy. There are new challenges to overcome every day; however, these are not hindrances but opportunities for you to become better. There are highs and lows, and the underlying emotions are beyond extreme. You can be “King of the World” one day and “The Biggest Loser” the next.

Success is never guaranteed the moment you accept the mantle of entrepreneurship. The only guarantee is your life will never be the same. Entrepreneurship will not change you; it will transform you.

Here are at least five life lessons I have learned as a serial entrepreneur.

1. Be prepared to fall several times

Name me a successful entrepreneur who did not fail even once in his or her life, and I will show you where to find a Golden Unicorn. Every entrepreneur has experienced failure at least once in his or her life. However, the best, most iconic entrepreneurs are those who have failed several times; some have even experienced failure several hundred times over. There is a saying that goes, “iron forges iron.” Failure is never easy in any shape, way, or form. It doesn’t matter who you are. You will feel pain.

There is no typo. I really meant “be prepared to fall” not “fail” several times. The feeling of failure is akin to falling and landing on a hard surface. When you fall, your body will not feel the onset of pain until it registers in your brain and it sends signals to your pain receptors. The pain of failure is the same. It will take your brain some time to process the experience before it prescribes the next course of action. But make no mistake about it; you will feel pain and its gnawing clutches on your insides.

As an entrepreneur, there are no limits to the number of times you will fall. Entrepreneurs are after all by definition, risk takers. If you want greater rewards, you must expose yourself to greater risk and take chances. However, unlike high-risk investments, an entrepreneur cannot place a “stop loss” order and exit once the pricing point has been achieved. The height of your fall depends on the level of risk you take and thus, the force of impact. Moreover, the more you rise and make the climb, the more you expose yourself to greater and impactful falls.

And this is how you become successful. The ability to get back up and make the climb until you conquer the challenge is what forges entrepreneurs to become a thing of iron—unbendable, unbreakable. It conditions your will, that is, it makes you indomitable and focused on reaching your goals.

When you fall, you must immediately assess the situation and ask yourself, “Why did I fall?” The operative word is “immediately.” Do not waste time feeling sorry for yourself or wallow in self-pity over what your failure has cost you. You should do an honest accounting of everything that you had done prior to the climb and figure out where you could have gone wrong, that is, where the mistakes could have been made. The faster you can get back on course, the greater your chances of overcoming the obstacle.

2. Be prepared to lose everything

When my family got in the food business, I remember my father said to me just seconds before signing the Master Franchise Agreement, “Are you prepared to lose everything? Even the shirt off your back?” I just laughed in jest thinking it was my Dad’s subtle attempt at humor. But he was unsmiling as he signed on the dotted line. We were on the cusp of starting a business at which none of us had any experience. I thought none of it because the franchise we signed up had great financials, a solid reputation in the US fast-food market, and most importantly, the best hamburgers I ever tasted.

Within 10 years, my father almost lost everything that he had worked for the past 50 years of his life. But it wasn’t just my father who lost financially. I had to sacrifice my salary to keep the business moving. In 2003, I had my first-born son. My entire life savings was run down. I barely had enough to buy diapers much less sustain my family. I was fortunate that my wife had a well-paying job.

But despite the damage, the sense of loss permeated the air and has unbelievably overcome any sense of relief when we shuttered the doors of the remaining franchise. I was exhausted, spent, and beaten. But I wanted to get back and try again without hesitation. I realized then that I could never go back to a regular 9-to-5 job. My life would be committed to entrepreneurship.

Before you become an entrepreneur, ask yourself just how committed are you to the venture?

What are you prepared to do?

What are you prepared to sacrifice?

There are nights where I have kept the television open hoping for sleep to takeover and give me some respite from the day’s problems only to be roused at 3:00 am or some other ungodly hour; the little demons have come out sticking their pitchforks in my subconscious. My forehead is covered in cold sweat despite the air-conditioner set at 16 degrees.

My only solace is the computer. I must start working and accomplish farther than I did the other day. It is the only way to keep the demons at bay.

This was my life for the first nine months of 2013.

When you are committed to any endeavor, you should accept the possibility of losing everything you have, that is, garnishing everything you have worked for. Even your relationships with your spouse, children, immediate family, friends, and associates will be at risk of compromise. However, it doesn’t mean that once all appears lost, you would throw your hands up in the air and give up.

You must be strategic and disciplined. All business ideas must have a plan—a framework of reference for all activity. Your business plan must be dynamic; it should be subject to change depending on the prevailing conditions. As such, your targets for profit and exit points will inevitably change as you progress. Once your studies show that there is no other resolution, exercise your alternative option and implement your exit strategy.

3. Your experiences strengthen your mind, body, and spirit

The challenges you will face as an entrepreneur will be far greater than anything you can imagine. As a regular employee, you are paid a salary to perform a predetermined series of tasks and responsibilities. Work was centralized; there were hierarchy and workflows to respect. My risk was limited to my scope of work. Given that you are an entrepreneur, everything will flow through you. The stress can be unbearable at times, and some people eventually succumb to it.

There is pressure to perform and to turn in results, and these are exacerbated when there are bills to pay. As a regular employee, you lived vicariously through the eyes of your boss; “He should have done this….he should have done that…” But as an entrepreneur, your ideas have now manifested themselves into your current reality, and often times, you feel lost.

I personally know of entrepreneurs who gave in to the stresses and attempted to drown out the pressures through alcohol, medication, and other excesses. In our conversations, alcohol, medication, and food were not outlets but methods to numb the pain. Once the numbness is gone, the pain remains magnified by the lack of self-worth.

Remember this, unless you act on your situation, you will never find your way out of your predicament. You can drink yourself into a stupor; but when you wake up, the problems remain. Instead of compromising your health, you should fortify it with exercise and meditation and embrace a lifestyle that gives importance to your well-being.

I simply cannot function without at least 90 minutes of physical activity. It helps clear my head and set my mood for the day. I make it a point to be in the gym at least four days a week. When I’m in the gym, I don’t exercise; I train. There’s a big difference. Everyone can exercise in the gym but when you train, you have a purpose. You are trying to accomplish a goal, therefore, there is strategy and planning involved. Every step that brings you closer to your goal makes you a better person and gives you more confidence to overcome the challenges you face in everyday life.

Combine physical activity with meditation and a well-balanced lifestyle, so you can prepare yourself for the pitfalls ahead. Whenever you are besieged with problems and situations, take a few minutes and meditate. Close your eyes and summarize all the blessings you have received today so far. You will be surprised at how many have come your way but you were too preoccupied with despair and regret to notice! Once you take full accounting of life’s daily blessings, reconcile with your spirituality, embrace your faith, and say with all your heart, “Thank You for giving me these blessings!” When you open your eyes, you will feel reinvigorated and energized with more spirit to take on more challenges!

The greatest and most powerful emotion in the world is LOVE. It has stopped tanks from rolling on people, changed the course of history, and brought powerful men to their knees. Despite what life gives you, do not reciprocate with hate. Learn to love who you are and accept that all of these is part of a greater journey.

4. Your success, or failure, as an entrepreneur will not define who you are

In November 15, 2012, I received a phone call from the biggest client of our company. I still remember the call as if it was yesterday:

“I’m sorry to inform you, Ricky, but despite your company’s performance [in] the last four years, the board of directors has made the decision to terminate our contract due to business losses. We are a publicly traded company and as you can see, the numbers speak for themselves. I wish there was a better way to handle this just a month before Christmas but there isn’t. We will honor the 60-day pre-termination provision in our contract.”

And just like that, life had changed. I had just moved my family into our new home, which I financed through a housing loan. I was suddenly back in the same predicament I was when I ran the restaurant. I was in danger of running down my savings.

But I had the foresight of starting a new outsourcing company as I realized months earlier that the directors of my current company were becoming disillusioned with outsourcing. I had started the process of organizing the new company when the call came through. I then had to work double time because the next stage was to secure clients.

It took me six months to land my first client, and the experience was draining me financially. My savings was being stretched out to support my family and my company and to pay off the housing loan amortization. But I was undeterred and kept pushing. I was signing up clients and was in the process of on-boarding them before the end of 2013. We were finally running as a company that services paying clients by December 2013.

Then, on February 20, 2013, I received a call. It was my bank. My check for Php1,800 was insufficiently funded. I was now officially broke. I called up the depository banks for the new company to check if the clients’ payments were already credited. As they say, “If life throws you lemons, you make lemonade.” I was fortunate that all the payments came through. I was relieved but still in a state of shock. I had never been broke before. This was a new experience for me.

My wife and son picked me up, and we headed off to the bank to withdraw some dollars to pay off our bills. As we’re heading to the money changer, I told my son what I had gone through and how things may change from now on. He smiled and said, “That’s okay as long as we’re all together, we’ll be fine.” And that changed my perspective on life as an entrepreneur.

We should handle life’s losses with the same magnanimity and dignity as we do life’s victories. Because in the end, it doesn’t matter how many times you have fallen, how much money you have lost, how much money you have in your bank account, or how many cars you drive; what matters is that you realize there is more to life than work and career. Whether you succeed as an entrepreneur or not, you should never lose sight of those who matter in your life—the ones who continue to inspire and motivate you to succeed. Even if success should elude you, they will never leave you.

5. Success is never measured in dollars and cents

When I read stories on success, I am least impressed by the amount of wealth an entrepreneur has generated in his career. For me, your net worth does not determine your level of success. When your business has achieved an impressive level of growth and a measure of sustainable success, you now have the means to influence or make a difference. What determines your level of success is your ability to change people’s lives.

I believe every entrepreneur should indoctrinate social responsibility within the business framework. Business is a huge lever for transformation. When we succeed, the profits we generate are not just a means to further our business goals, but instead, these profits provide the avenues to make a difference in the world. A contribution, regardless of size or amount, can create a ripple that can extend beyond the scope of the pond, a river, or perhaps even an ocean.

Last December 31, I was approached by two homeless children at the entrance of a grocery store. Instead of giving cash, I bought them groceries for New Year’s Eve. I only had a hundred and fifty pesos in my wallet but I was able to squeeze in a liter of Coke, two packs of cookies and candies, an ensaymada roll, three bags of chips, and an ube cake, which was on sale. I gave the two bags to the children who thanked me then ran off to the corner to eat the food. They called two other homeless children and shared the goodies. I stayed inside my car and watched the children devour the groceries in record time. It felt good knowing that at least for that night, four children would not go to sleep hungry.

That evening during our New Year’s Eve meal, I shared my story to my son. I told him, “You should be thankful for everything that you have in your life every single day. So when you have the means to do so, share your blessings with those who have less.”

As entrepreneurs, we all want to succeed and change our lives—to provide a life of comfort and security for ourselves and especially for our families. However, we also need to understand that we have an innate responsibility to transform the lives and to improve the well-being of those who work for us, our community, and society.

Success brings in money and money affords us the means to live the life of our choosing. Thus, people have associated money with power. But absolute power corrupts absolutely, which is why some entrepreneurs are consumed by their own success. True power is not measured by the influence your money wields but in how your resources are utilized to influence positive transformation in the lives of others.

My journey to entrepreneurial success is far from over. I have yet to see my destination in the horizon. But perhaps, the journey of entrepreneurship has no end but only pit stops along the way because there is more to discover in business and in life.

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