National Entrepreneurs Day: 4 Incredible Yet Contentious Tech Entrepreneurs

By Fraser Gillies Published: 19 November, 2019 Last updated: February 17th, 2022 at 4:23 pm

Mark Zuckerberg image

When you’re young, you’re taught that running your own business is the pinnacle. 

Have a great idea, see it through properly, then become rich and prosper. 

If only life as an entrepreneur were that easy…

The countless number of business roadblocks and punitive market forces mean that only 50% of new companies make it to their fifth year. Whatever your grand master-plan for success is, the odds are stacked against you. But that doesn’t mean it’s impossible.

National Entrepreneurs Day celebrates individuals who’ve built empires from scratch and become images of aspiration for budding business newcomers. 

Whilst being adulated for their accomplishments, they occasionally find themselves embroiled public rows and legal issues, and thrust into the spotlight for the wrong reasons. 

We’ve put together a motley crew of inspiring tech entrepreneurs who have at one time or another, been wrapped up in a spot of controversy:

Elon Musk

Elon Musk is somewhat a renaissance man when it comes to transporting people around the planet and solar system. 

In 2003, he co-founded the luxury electric car company Tesla Motors Inc – attributing the company’s name to fellow engineer and visionary Nikola Tesla. 

Tesla has since transformed public perception of the electric car. Laymen viewed them as expensive and gearheads believed that going green meant a compromise in performance. However, due to Musk and Tesla’s clever rebranding, Tesla has grown exponentially. Its combination of style and substance has convinced many car enthusiasts that going green doesn’t mean scrimping on quality. 

The previous year, Musk created Space X, an aerospace manufacturer and transportation provider. He had one mission. To colonize Mars as cost-effectively as possible. Space X spent the next 17 years sending rockets into the galaxy and developing interplanetary cruise ships.

Through another one of his pet projects, The Boring Company, Musk is building underground tunnels to combat city congestion. 

Despite his incredible contributions to the tech industry, Musk has still found himself in spots of bother over the years

In 2017, Musk was forced to step down as Chairman from Tesla due to a tweet suggesting he’d secured sufficient funds to take the company private. Shareholders were left bemused and SEC slapped a $40 million fine on Tesla for fraud. That being said, Musk did retain his position as CEO.

More recently, Tesla was implicated in further scandal regarding their solar panel project. Walmart sued Tesla for selling faulty panels that caught fire in at least seven of their stores. The story has brought Musk’s affiliation with Tesla into question, and even led calls for his resignation.

Jack Dorsey

Jack Dorsey’s daily ode to Stoicism is admirable at the least. 

Each day starts with an ice bath. He then walks over five miles to work. He only eats one meal a day (fasting on the weekends). If he’s working out, he’s doing it in seven minute sessions and doesn’t bother with a gym. 

He must have cheat days though, right?

I digress.

When he’s not putting the rest of us to shame, Dorsey is juggling two CEO positions:

  • One with the social media platform,Twitter
  • The other with small business payment company, Square

As a tech entrepreneur, Dorsey has been heralded for revolutionizing the way we interact online. With roughly 330 million users, Twitter has given voices to disenfranchized members of society and people in political refuge. 

However, the platform has faced criticizm for harboring alleged biases regarding user censorship. There has been an ongoing debate about the power platforms like Twitter and Facerbook have to depose and delete accounts espousing opinions that run against the companies apparent left-leaning politics. 

Although this bias remains conjecture, there have been various cases where people have seen their accounts blocked for inciting speech considered to be hateful. 

Dorsey went on Joe Rogan’s podcast with Twitter’s head of legal Vijaya Gadde to discuss the controversy and was accused of being deliberately evasive on his views of the company’s censorship policies. 

Bill Gates

From a young age, Bill Gates was destined for greatness. 

Gates wrote his first software program at the age of 13. However, It all really kicked off for Gates in 1975 when he co-founded software powerhouse, Microsoft. Fast forward to present day, he’s now the world’s second richest man. His estimated worth is over $100 billion

Gates created tens of thousands of jobs through Microsoft. Furthermore, he was the face of computing technology for over two decades. He brushed off competition and infamously dueled with tech rival and founder of Apple, Steve Jobs. 

Gates is not only a symbol of technological innovation. He’s also a philanthropist. This year alone, he’s away $35 billion dollars through him and his wife’s charity, The Bill and Melinda Gates Foundation.

Nevertheless, his life as arguably the world’s most famous tech entrepreneur has not been without its problems.

Gates was called to attend a US senate committee hearing in 1998 about potential government restrictions on Microsoft’s business activity. At that time, Microsoft had an unbelievable 86% market share of personal computer operating system industry. Gates defended his business’ monopoly, citing free market economics and that some companies – unlike his – “fail to embrace change”.

Mark Zuckerberg

Is there a more recognizable social media platform than Facebook? 

If I’m honest, it feels like the epicentre of the social media storm that began in the early-mid 2000’s, and blew other platforms like MySpace and Bebo into a distant memory.

It’s co-founder, Mark Zuckerberg, burst onto the scene in his mid-twenties and has been the twenty-first century role model for young tech entrepreneurs. A gifted yet absent Harvard student, Zuckerberg created Facebook in 2004 as a way of connecting Harvard alumni online. 

In three years the platform had gained 20 million worldwide users, and today has a jaw-dropping 2.4 billion active users. However, Zuckerberg’s road to success has not been easy.

He was sued by former classmates Cameron and Tyler Winkelvoss for stealing the idea of Facebook from their own social networking site ConnectU. He settled and paid the pair $65 million in damages. 

Most notably, he testified in the US Congress over a major data privacy scandal. Zuckerberg was questioned in front of a committee of congress people regarding Facebook’s affiliation Cambridge Analytica – a political consulting firm who harvested and misappropriated data from millions of Facebook profiles for the purposes of influencing online political debate. 

Moreover, Facebook has recently been condemned by multiple media outlets for its stance on political ads. They stated keeping political ads on their platform, even those that deliberately give users false information, was an upholding of democractic freedom. On the flip side, Twitter have set out their stall on the issue – making clear they won’t be running any political ads on their platform. 

Final Thoughts

National Entrepreneurs Day honors the best and brightest industry leaders around the world. It’s important to recognize big achievement, if only to inspire the future trailblazers of technological development.

While they can wow us, the same entrepreneurs can confuse us with penchants for peculiar decision-making and glaring errors in judgement. 

Even though you won’t be rubbing shoulders with these innovators any time soon – or smoking their meats – you can definitely learn from their mistakes when embarking on your own enterprise.


Fraser Gillies

Fraser has been working in the digital communications space for four years. Currently the Head of Revenue at Publicize, he is leading a team of talented content creators to build powerful tech narratives that engage, educate and entertain audiences.