The Pros and Cons of an Exceptional Entrepreneur Father

With Father’s Day just around the corner, I thought it might be worthwhile to take a look at the pros and cons of having an exceptional entrepreneur father. And there is no one better equipped to write about this subject than me! No, there is nothing to brag about as I did nothing to deserve this accolade. I am privileged enough to have had an exceptional entrepreneur father. Or am I?

Nothing is ever what it seems

Many great minds are of the opinion that being raised in a privileged home is a recipe for disaster. Christiaan Wessels wrote in the MoneyWeb article of 22 March 2022 titled “Why family business fails” that on average only 30% of businesses survive from one generation to the next. Malcolm Gladwell wrote in David and Goliath ad-lib about the subject that the highest propensity to become extraordinary stems from adversity and not from a privilege. And then there is the infamous line of Tony Robbins: “your father fucked you up.”

From a humble start to an exceptional entrepreneur father

One thing I did learn from my entrepreneur father is that it is not where you come from that matters, but where you are growing towards. He came from a seriously humble subsistence farmer family of 12 children.   Solid values, but very little otherwise. In fact, their family’s financial survival was a direct result of his father who died at the end of World War II when my dad was only eleven years old. This afforded his mother the opportunity to earn a monthly allowance from the government, which kept the pot cooking.

There was no money for shoes or to finish school. He started out as a humble bricklayer with no stars in his eyes of being great, but with a will to consistently do good and be good. A real-life, old-fashioned Atomic Habits example of an exceptional entrepreneur father. A traumatic accident in which he was initially declared dead, killed his employer and with that his only hope of employment. After months of rehabilitation, he started his own building company, two days before his marriage to my mom in 1957. With zero reserves and no client in sight. In fact, the first house that he built was his own which he financed through my mother’s teacher’s salary at the time.

What seems like the end, might only be the beginning.

Getting up one more time

The amount of victim-to-hero self-help books is in oversupply. Most people already know that heroes don’t blame. They do not sit on a rock and cry the poor-me song. Robin Sharma writes in his book Everyday Hero that ‘life loves those everyday heroes who understand that they possess abilities, capabilities and the force to shape all events that destiny carefully places on their path.

My entrepreneur father is an exemplary example of this fact. Can you imagine what would have happened if he allowed self-pity to get the better of him? Make no mistake, he has definitely had his ups and downs. No story is ever a linear ever-after magic affair. One of Nelson Mandela’s quotes holds true in this circumstance: “Do not judge me by my successes. Judge me by how many times I fell down and got back up again.”

Lessons from my Entrepreneur Father

While I was at varsity, my dad wrote in one of his many handwritten letters to me that it is a great act of bravery to take off your clothes once to save your brother from imminent death, but it is an even greater act of heroism to put on your clothes every day for thirty to forty years to provide for your family.’ And this he did with exceptional valor.

Coming from a background of not having money to finish school, he worked himself up one small step at a time. He observed the bricklayers around him and decided that was not where he wanted to end up.  He undertook a diploma in draughting and cost accounting to plan and design his own homes, Dale Carnegie courses to become a public speaker and yes, he did finish his matric through the post. And above all, he kept on reading and learning. Dale Carnegie, Readers Digest, and Finansies & Tegniek were some of the omnipresent titles in our home. Instilling atomic habits 1% at a time.  

Flip Rosslee winning the Mayoral Trophy one more time.

To leave a legacy or not

I have recently had a fairly heated conversation with someone who could not understand why I am continuously being involved in so many things on so many levels. Personally, I cannot see how it is possible to only live for yourself and your own pleasures. Do I want to leave a massive legacy? Honestly, I am not so sure anymore.  Robin Sharma wrote in Everyday Hero: “I believe that pursuing a noteworthy legacy is the occupation of a screaming ego.” Robin professes that making a difference while your tender heart is still beating, is the way of real heroes and I fully agree.

My dad was driven to give back to the community in whatever way was required. He has spent a lot of unselfish hours developing the Alberton Sakekamer as part of his passion to develop local entrepreneurs. My father did not care to become involved in organizations like the then Broederbond or the high society of our town, but he did stand up when help was needed in our church, the local schools, foster homes, or wherever he could see help was needed. Did he plan to leave a legacy? No, I don’t think so. He merely did what needed to be done wherever he could. All in the humble, simplistic manner that was his trademark.

Abundance does not lead to greatness

So where does this leave me as someone who came from a background of abundance? There are so many traps that one can fall into. For one, you can grow up without the incessant drive to succeed. People often feel sorry for themselves that they do not have the opportunities that they would have liked, but the contrary is that if you have the opportunities, it is just not such a big deal as it would have been if you had craved it.

Fear of success sounds like a whole lot of bull, but it could lead to subconsciously being afraid to venture outside of the parameters that have been laid out for you by your parents. In 1915, Sigmund Freud wrote an article called “Those Wrecked by Success”. He described a tendency to fail “precisely when a deeply rooted and long-cherished wish has come to fulfillment as though they were not able to tolerate happiness”.

You could be unconscious of the fact that you are clinically stuck. That you live in the shadow of their greatness and that you are uncomfortable trying something new and innovative. This is often the reason why second-generation businesses fail to stay a leader in their field or just fail altogether. Again, being stuck without knowing until it is too late.

Follow in the footsteps of Heroes

One place you could definitely get stuck in is dwelling too much on what can go wrong and not focussing on the positives. Having a father entrepreneur as your business mentor and hero remains an amazing privilege and a gift to cherish and develop. After all, if you do not develop your gifts to optimal potential, you do risk losing them. 

I had the privilege of listening to so many business stories. I have experienced someone who truly loved what he was doing. To such an extent that he was physically involved in his developments up until two months before he passed away at the age of 86.

So much wisdom has shaped the way I think and do and possibly the reason why I feel called to help those in need of a business hero. 

Flip Rosslee with his wife, children, grandchildren, and great-grandchildren on his 60th wedding anniversary in 2017.

Expedition Business

Expedition Business is a series of business people sharing their tales of the ups and downs of business. The how they get over their disappointments. Insights into their inspiration. The wisdom from the firepit sessions as it were. Almost like reading their autobiography. Just delivered short and sweet and to the point. To be a hero for someone, somewhere, somehow. I have had the privilege of having an exceptional entrepreneur father and this is my way of giving back. 

We’d love to hear your story no matter who you are.

Please get in contact with us and we’ll help you share your story.

You never know.  You might be a hero to someone, somewhere.

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