When Start-ups Go Rogue: Bad Entrepreneurs

There’s a reason the saying “there are two types of people in the world: the ones who start companies and the ones who work for them” exists. It takes a special kind of person to be an entrepreneur, and not everyone has what it takes. Some entrepreneurs start their businesses with the intention of making the world a better place, while others are in it purely for the money. Unfortunately, there are also a number of entrepreneurs out there who are simply bad at what they do. In this blog post, we’ll take a look at some examples of bad entrepreneurs and the lessons we can learn from them.

1) Elizabeth Holmes – Theranos CEO

Elizabeth Holmes- Theranos CEO

Elizabeth Holmes is the founder and former CEO of the now-defunct Theranos, a start-up that promised to revolutionize the blood-testing industry. However, it was later revealed that the company’s technology was not as advanced as they had claimed, and Theranos ultimately collapsed. Elizabeth Holmes was arrested and charged with multiple counts of fraud.

Elizabeth Holmes is a perfect example of how not to be an entrepreneur. She was dishonest about her company’s technology, and as a result, she lost the trust of her investors and customers.

Lesson: Don’t lie to your investors or customers. If you do, you will ultimately lose their trust and your business will suffer as a result.

2) Trevor Milton – Nikola Chairman

Nikola Founder and Executive Chairman Trevor Milton

Trevor Milton is the founder and former chairman of Nikola, a start-up that was working on developing electric and hydrogen-powered trucks. However, the company came under fire after it was revealed that it had misled investors about its technology. Trevor Milton resigned from his position as chairman, and the SEC launched an investigation into the company.

As the stock price soared, Trevor Milton sold off $146 million of his shares. It’s always a red flag when insiders start selling their shares, and in this case, it turned out to be a sign that the company was in trouble.

Lesson: Don’t mislead investors about your company’s technology or progress. If you do, you will face serious consequences.

3) Jessica Alba – The Honest Company Cofounder

Jessica Alba – The Honest Company

Jessica Alba is the co-founder of The Honest Company, a start-up that sells eco-friendly household products. However, the company has come under fire in recent years for false advertising. In 2015, the company was sued for falsely claiming that its laundry detergent was “free of harsh chemicals.” The suit was later settled for $11.75 million.

While Jessica Alba is not the only entrepreneur to have been accused of false advertising, she is a prime example of how not to run a business. Her company has been embroiled in multiple lawsuits, and its reputation has been damaged as a result.

Lesson: Don’t engage in false advertising. If you do, you will face legal repercussions and your company’s reputation will be ruined. Spend the money and the time to get the correct information before you start promoting your products or services.

4) Shani Higgins – Technorati CEO

Shani Higgins

Shani Higgins is the founder and former CEO of Technorati, a start-up that was once one of the most popular blogs in the world. However, the company was eventually eclipsed by newer and more popular blogs, and it was sold for a fraction of its former value.

In 2007, Shani Higgins cashed out her shares in the company for $20 million. She then proceeded to spend the next few years travelling the world and living lavishly. Her story is a cautionary tale for entrepreneurs who think they can cash out and live the high life after their start-up is acquired.

Lesson: Just because your start-up is acquired doesn’t mean you can rest on your laurels. In the tech world, things move quickly, and if you’re not careful, your company can be eclipsed by newer and more innovative companies. Stay focused and keep working hard, even after your start-up is acquired.

5) Dan Price – Gravity CEO

Dan Price – Gravity CEO

Dan Price is the founder and former CEO of Gravity, a start-up that created a popular mobile game. However, the company ran into trouble after it was revealed that Dan Price had used company funds to pay for his lavish lifestyle. He was eventually ousted from the company, and the board sued him for $330 million.

Lesson: Don’t use company funds for personal expenses. If you do, you will be held accountable and you could face legal action. Be mindful of how you spend the company’s money, and make sure that all expenditures are justified.

6) Billy McFarland – Fyre Festival Founder

Billy McFarland – Fyre Festival

Billy McFarland is the founder of the now-infamous Fyre Festival. The festival was advertised as a luxurious event on a private island, but it quickly descended into chaos. Attendees were stranded without food or water, and the event was eventually cancelled. Billy McFarland was arrested and charged with wire fraud.

The Fyre Festival was a complete disaster, and it ruined Billy McFarland’s reputation. If you’re planning on hosting an event, make sure that you can actually deliver on your promises.

Lesson: Don’t over-promise and under-deliver, or you will end up in hot water. Mean what you say and say what you mean when it comes to business!

7) Dave McClure – 500 Startups

Dave McClure

Dave McClure is the founder of 500 Startups, a venture capital firm that has invested in over 2000 companies. However, the company has been embroiled in controversy after it was revealed that Dave McClure had engaged in sexual misconduct with female entrepreneurs.

While Dave McClure is not the only entrepreneur to have been accused of sexual misconduct, the #MeToo movement has brought this issue to the forefront. Sexual harassment and assault are not acceptable in the workplace, and entrepreneurs who engage in this behaviour will be held accountable.

Lesson: Avoid sexual encounters of any sort in the workplace. If you are accused of sexual misconduct, your reputation will be ruined and you could face legal action. It’s not worth the risk!

10 traits to avoid as an entrepreneur

To ensure you are a  good entrepreneur and not a bad one that will bring their company down, here are the top ten traits to avoid:

  • Always late
  • Never follow through on their promises
  • They don’t take feedback well
  • They’re always talking about themselves
  • Making excuses instead of taking responsibility
  • They’re never satisfied with their own work
  • They’re always in a hurry – they don’t have time for anyone else
  • They’re always negative and complaining
  • Their prices are too high or they’re not willing to negotiate
  • They don’t treat their employees well


It’s time to start calling out these bad entrepreneurs so that the rest of us can learn from their mistakes. We need to create a community where it is not acceptable to act this way, and we can all benefit from doing better. What do you think? Let me know in the comments below.

It starts with an idea. Pop Up World is a platform that helps start-ups and small businesses reach for the stars. No matter what size you are. Use our start-up guide Business Zero to Superhero, Design your Logo. Connect with investors via our Investor Connector. You can start a Website and Domain name. You can Search for and promote your Premises. You can promote your idea for free on our Pop Up World Ads site, you can even form a Limited Company You can also join us on our journey via the Pop Up World Token (PUW).

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