Startups

5 Times Famous Entrepreneurs Expressed Their Regrets

  • 4 min Read
  • July 20, 2020

Author

Tasnim Ahmed
Tasnim Ahmed

Tasnim Ahmed is a content writer at Escalon Business Services who enjoys writing on a multitude of subjects that include finops, peopleops, risk management, entrepreneurship, VC and startup culture. Based in Delhi NCR, she previously contributed to ANI, Qatar Tribune, Marhaba, Havas Worldwide, and curated content for top-notch brands in the PR sphere. On weekends, she loves to explore the city on a motorcycle and binge watch new OTT releases with a plateful of piping hot dumplings!

Table of Contents

Ask any entrepreneur about their successes, and they’re sure to mention that they encountered challenges along the way, which can sometimes lead to breakthroughs, and may in other cases lead to regret.

Check out what the following five well-known entrepreneurs have said about the regrets they have about the past so you can learn from their mistakes.

Bill Gates

The Microsoft cofounder built a computer empire, but that doesn’t mean he lives his life without regrets. In fact, he refers to one big product line that he wishes he had mastered better — the mobile phone.

“In the software world, particularly for platforms, these are winner-take-all markets. So the greatest mistake ever is whatever mismanagement I engaged in that caused Microsoft not to be what Android is,” he said last year. “That is, Android is the standard non-Apple phone platform. That was a natural thing for Microsoft to win. It really is winner take all. If you’re there with half as many apps or 90 percent as many apps, you’re on your way to complete doom. There’s room for exactly one non-Apple operating system and what’s that worth? $400 billion that would be transferred from company G to company M.”

Oprah Winfrey

After building a talk show empire that remained at the top of its game for years, Winfrey aimed to establish her television network OWN as a game-changer, but there were many kinks that needed to be worked out along the way, she said.

In fact, she told CBS This Morning in 2012, “Had I known it was this difficult, I might have done something else.” The biggest regret she had was launching the network before it was completely ready, which she likened to getting married before being totally prepared for it.

Dave Thomas

When the Wendy’s founder launched the hamburger chain in 1969, he did so after having worked for KFC founder Colonel Sanders for years, which led him to believe the company should have a character to associate with the brand. What he regretted, he later said, was basing that character on his own daughter, who was named Wendy.

“Before my dad left us, we had a long conversation about him naming the restaurant Wendy’s,” Wendy Thomas said. “He said, ‘You know what? I’m sorry.’ I asked him what he meant. He explained, ‘I should’ve just named it after myself, because it put a lot of pressure on you.'”

Mark Cuban

The Broadcast.com founder and Shark Tank investor has invested in both money-making and money-losing ventures during his long career, but it’s one investment he didn’t make that he considers to be among his biggest regrets.

He was approached by Uber founder Travis Kalanick when the idea for the ride-sharing company was first floated, and instead of investing, Cuban pointed out the headwinds that Kalanick would face if he continued on with the idea. “You are going to have to fight all the taxi associations, and all the transportation organizations in each city and every state,” Cuban told him. He realized later that he should have known better than to have doubted an entrepreneur’s ability to break through such types of hurdles rather than having withheld his investment dollars.

Magic Johnson

The basketball great and entrepreneur was just 19 years old when he joined the NBA and started getting endorsement offers. Although he knew he wanted to make a deal with a sneaker company, he didn’t know enough about investing to consider taking a stock deal rather than a cash offer, which he now regrets.

“Converse came in and offered me some money,” he said. “And then this guy named Phil Knight came in, and Nike was only like one or two years old. He said he doesn’t have a lot of money but will offer me stock.” Johnson took the cash offer with Converse and has thought about it many times since then. “Boy, did I make a mistake. I’m still kicking myself,” he said. “Every time I’m in a Nike store, I get mad. I could’ve been making money off of everybody buying Nikes right now.”

Talk to our team today to learn how Escalon can help take your company to the next level.

  • Expertise you can trust

    Our team is made up of seasoned professionals who bring years of industry experience to the table. You gain a trusted advisor who understands your business inside out.

  • Quality and consistency

    Say goodbye to the hassles of hiring, training and managing in-house finance teams. You will never have to worry about unexpected leave of absence or retraining new employees.

  • Scalability and Flexibility

    Whether you’re a small business or a global powerhouse, our solutions scale with your needs. We eliminate inefficiencies, reduce costs and help you focus on growing your business.

Contact Us Today!

Tap into the latest insights from experts in your industry

Small Businesses

The ROI of Outsourcing Business Services: How to Measure Your Investment’s Impact 

The ROI of Outsourcing Business Services: How to Measure Your Investment’s Impact  In a world where every dollar must count,...

Read More
People Management & HR

2025 Employment Law Updates: What to Know

As we step into 2025, businesses across the country face several important updates in labor laws and employee benefits. Staying...

Read More
Startups

5 Signs Your Startup Needs an Outsourced CFO  

5 Signs Your Startup Needs an Outsourced CFO   Startups often operate with lean teams, but as they grow, financial complexity...

Read More
Leadership & Growth

CG Startups: How to Keep Costs Low While Scaling Operations 

Consumer Goods Startups: How to Keep Costs Low While Scaling Operations  Scaling a consumer goods startup requires a careful balancing...

Read More
Press Releases

Escalon Expands Its Reach: Full Stack Finance and Early Growth Join Forces with Industry Leader 

Escalon Expands Its Reach: Full Stack Finance and Early Growth Join Forces with Industry Leader  In a strategic move that...

Read More
Taxes

Delaware Annual Review: What Series A-C Startups Must Know to Stay Compliant 

Delaware Annual Review: What Series A-C Startups Must Know to Stay Compliant  For startups incorporated in Delaware, staying compliant is...

Read More
Taxes

Tax Planning for Startups: Preparing for Your First Tax Filing

Tax Planning for Startups: Preparing for Your First Tax Filing as a Growing Business  For many startups, the first major...

Read More
Taxes

Unlock Tax Savings with the R&D Tax Credit

As a startup, managing cash flow and minimizing expenses are critical to your business's survival and growth. One often-overlooked opportunity...

Read More
Accounting & Finance

1099 Compliance for Early Stage Startups

1099 Compliance for Early Stage Startups As your startup grows from seed funding to Series A, B, or C, you’ll...

Read More