When William Saito quit as a medical doctor immediately after qualifying, his parents refused to speak to him for two years.
A Dutch "positivity trainer" has launched a legal battle to change his age and boost his dating prospects.
But they're not complaining about the end result now, says the 44-year-old Japanese American.
He did the training to fulfil his parents' dream of him becoming a doctor, and as he jokes, his parents never actually said how long they wanted him to be a doctor for - just to be one.
Emile Ratelband, 69, wants to shift his birthday from March?11, 1949 to March?11, 1969, comparing the change to identifying as being transgender.
The reason he left so soon was because he was determined to carry on the venture he'd begun at just 11-years-old while still in junior high school.
He had founded his own start-up company, which eventually focused on enhanced security for personal computers through technologies such as fingerprint and iris recognition.
"We live in a time when you can change your name and change your gender. Why can't I decide my own age?" he said.
Mr Saito formally incorporated the firm - I/O Software - in 1991 while he was at university. The company became a leader in biometrics and information security, and just 14 years later at the age of 33 he sold it to US giant Microsoft.
While the terms of the deal mean he can't reveal the price he received, Mr Saito admits he would have been in a position to retire then if he'd wanted to.
Ratelband, who makes a living urging people and businesses to be positive, denies that the age request is a publicity stunt. He claims he is seeking a personal positive effect.
But unsurprisingly for someone so driven at such a young age, he has continued to work relentlessly, using his experience to help other entrepreneurs, particularly in his parents' home country of Japan.
While born and raised in the US, Mr Saito still believes he "owes the Japanese", because it's his heritage which he credits for his success. And now he believes he can give something back.
"Now I’m an old man. I have to save my money to give to my kids so that they can live,” said the father of seven. “But If I have that age again, I have hope again. I’m new again. The whole future is there for me again.”
'Changed my life'
Mr Saito's parents couldn't speak English when they emigrated to the US, settling in Los Angeles in California, just two years before he was born in 1971.
A local court in the eastern city of Arnhem is expected to rule on the case within four weeks.
Determined to give their son - the eldest of three - a competitive advantage to ensure he would thrive in their new country, they focused on mathematics, bringing over complex textbooks from Japan, and teaching him things well beyond the expected level for his age.
"That turned into a huge advantage for me," he says.
However officials were sceptical about the case, believing there was no legal mechanism allowing a person to change their birth date, local reports said.
In fact, his maths became so advanced that his teacher ran out of suitable lessons, suggesting he played with "a thing called a personal computer" instead.
"I was able to take advantage of this lead and it changed my life," Mr Saito says.
One of the judges wanted to know what would become of the 20 years that Mr Ratelband wanted to erase. "Who were your parents looking after then? Who was that little boy?" he was quoted as saying.
On this teacher's advice, his parents took out a home loan to buy him his very own personal computer - worth about $5,000 (£3,200) in today's money - which from their point of view was aimed at helping him become a doctor.
But some work, organised by the same teacher, changed the direction of his life permanently. The teacher suggested to a friend - an accountant at investment bank Merrill Lynch - that Mr Saito, who at the time was just 10-years-old, could help with writing computer programmes.
Mr Ratelband argues he feels discriminated against because of his age, and that it was affecting his employment chances and his success rate on the dating app, Tinder.
"When I finished I received a cheque, and I didn't expect that.
"That really changed my view about doing something fun, but at the same time getting paid for it. It was definitely a wake-up moment for me," he says.
"When I'm 69, I am limited. If I'm 49, then I can buy a new house, drive a different car. I can take up more work," he said.
Despite his precocious start, Mr Saito denies that he was hot-housed, saying his parents exposed him to lots of different activities, and made it clear that success was about more than just good grades.
In particular, he says both the schools he went to, and his parents, emphasised the importance of volunteering.
"When I'm on Tinder and it says I'm 69, I don't get an answer. When I'm 49, with the face I have, I will be in a luxurious position."
It's a lesson he has taken to heart, and since the successful sale of his first firm, he has worked hard to support other would-be entrepreneurs.
He confesses one of his favourite pursuits, is judging business plans, and he travels globally to do this. To date, he calculates he's judged some 15,000 people in such competitions.
Mr Ratelband further argued that according to his doctors he has the body of a 45-year-old, and described himself as a "young god".
But his main focus is his parents' home country of Japan.
He went on Facebook last year to describe how he had made the decision one day standing in front of a mirror, not because he feared getting old but because he wanted to make the most of life for as long as possible.
In 2005, after selling I/O Software, he moved to Japan and founded venture capital firm and consultancy InTecur.
He also works as a special adviser for the Japanese government, specialising in cybersecurity.
He also said he would renounce his pension if he switched his birth date.
But his main drive is to make the Japanese more entrepreneurial.
Ratelband says the Dutch government could benefit if it were to accept his age demand. He said he’d be happy to forfeit his monthly pension of around 1,200 euros — a concession he estimates would save nearly 300,000 euros over the 20 years he wants shaved off his age.
The Netherlands' constitution expressly prohibits employment discrimination on the basis of age.
Mr Ratelband, a media personality and motivational guru, converted to Buddhism earlier this year.
He voiced the character Vladimir Trunkov in the Dutch-language version of the Pixar film?Cars 2.
Plot twist: the gov accepts his demands. He becomes 49 again - and has to work 15 years to his pension. Joke's on him.
He is right!...I have 40 but I want to change to 80 to cash my pension...
I want to change my birth place to Mars.
That's what you get when reality and facts don't matter anymore.