Beyonce to Bill Gates: 24 Millionaires Reveal the Hardest Thing About Being an Entrepreneur

Photo Credit: JStone |

By Morgan Quinn, Feature Writer

Being your own boss might sound like a dream come true, but starting your own business isn’t an easy path. The reality is it takes a lot of sweat, tears, hard work and discipline to be a successful entrepreneur. From Beyonce to Bill Gates, we found out what some of the most successful entrepreneurs in history have to say about the most difficult parts of their jobs.

Read the 21 habits of successful billionaires like Warren Buffett >>>

1. Mark Zuckerberg: Inexperience

One of the world’s most recognized entrepreneurs and owner of the largest social media network in history knows you can’t find success on your own. “When I was getting started, I didn’t want to build a company and I didn’t know anything about building companies,” he said in a public Q-and-A on Facebook. “The thing that got me through it and I think gets a lot of people through it is the people around them.”

2. Larry Page: Being a Manager

Larry Page, cofounder of Google, understands his strengths and weaknesses and says the challenge comes in making up for the difference. “Certainly, I think, the things that I’m missing are more things that you acquire with time,” Page said in an interview with the Academy of Achievement.

“If you manage people for 20 years, or something like that, you pick up things. So I certainly lack experience there, and that’s an issue. But I sort of make up for that, I think, in terms of understanding where things are going to go, having a vision about the future, and really understanding the industry I am in, and what the company does, and also sort of the unique position of starting a company and working on it for three years before starting the company. Then working on it pretty hard, whatever, 24 hours a day. So I understand a lot of the aspects pretty well. I guess that compensates a little bit for lack of skills in other areas.”

3. Sergey Brin: Scaling the Company

Google’s other cofounder, Sergey Brin, said in the same interview there are many challenges to being an entrepreneur but “one is providing a service that’s going to serve millions of people. When we were at Stanford, we had about 10,000 searches per day. Now we serve over 50 million searches per day. That scaling of an infrastructure, that is pretty challenging.”

4. Lori Greiner: Dealing With Unethical People

In true Lori Greiner fashion, this “Shark Tank” investor isn’t afraid to tell it like it is. When asked about her biggest challenge in her career in a recent Reddit AMA, she wrote, “Dealing with unscrupulous people. P.S. — I have triumphed. Remember, Karma is a bitch — I believe in Karma and I have seen what goes around come back around.”

5. Steve Jobs: Simplicity

Steven Jobs is known for his focus, but that didn’t always come easy to the former Apple CEO. In an interview with Business Week, he explained, “That’s been one of my mantras — focus and simplicity. Simple can be harder than complex. You have to work hard to get your thinking clean to make it simple. But it’s worth it in the end because once you get there, you can move mountains.”

6. Bill Gates: Getting Overwhelmed by Technology

When you run a company like Microsoft, you understand the power of innovation. But small businesses that are just starting out might neglect this critical component of success. “Large companies recognize that effective use of technology is a strategic weapon,” Bill Gates told Entrepreneur magazine in a 1999 interview. “This is an area where small business can be overwhelmed and, as a result, may not take advantage of the power of technology available to them.”

Read: Bill Gates’ No. 1 Piece of Personal Finance Advice

7. Travis Kalanick: Getting Too Passionate

Entrepreneurs should be careful not to let their passion take over. Uber founder Travis Kalanick knows his intensity can send him down the rabbit hole, as he explained in an interview with Vanity Fair. “Look, I’m a passionate entrepreneur. I’m like fire and brimstone sometimes,” he said. “And so there are times when I’ll go–I’ll get too into the weeds and too into the debate, because I’m so passionate about it.” Passion is something all entrepreneurs need — just be sure to keep it in check.

8. J.K. Rowling: Failure

It’s hard to believe one of the most successful authors of all time struggles with failure, but she revealed this in an interview with Oprah Winfrey. “Failure. Failure … doesn’t get spoken about enough,” Rowling said.

“We speak about success all the time, but, you know, I do not know any — I haven’t met — and I’ve been so fortunate and met extraordinary people through Harry Potter, and not one of them didn’t have their failure, more than one failure. And it’s the ability to resist failure, in many ways, or use failure that often leads to the greatest success, isn’t it?”

9. Dr. Dre: Building the Right Team

It took Dr. Dre some time to build the right team to propel him to superstardom. “I’m a perfectionist, but it has a lot to do with the people that are around you,” he told Scratch Magazine. “They have to have the same vision, the same motivation. It takes a while to get the right people around you; it takes a long time. But I think I’ve finally done it, I think this is going to be my crew for a while.” Considering Dr. Dre is one of the world’s richest hip hop artists, we’d say he’s finally done it, too.

10. Mark Cuban: The Word “No”

Mark Cuban just won’t take “no” for an answer. As he told Dave Ramsey, “Every no gets you closer to a yes. It’s a numbers game. … It’s just a question of making the calls.” With a net worth of $3 billion, we shudder at the thought of his phone bill.

11. Jack Dorsey: Bookkeeping

You’ve got to love Twitter cofounder Jack Dorsey’s total honesty. In an interview with USA Today, he described the panic of starting his new company, Square: “I had no idea what I was doing! I learned as I went, working every shift, every day,” he said. “My biggest hurdle was bookkeeping. [I learned by] trial and error. I learned from my mistakes and really listened to customer suggestions. Some of our best-selling items were created by employees and customers.”

12. Beyonce: Pressure to Keep Up

Beyonce might seem flawless, but even she struggles to stay calm and collected. “The pressure to keep up the pace can be unbearable but I try to take it all in stride,” she told Island Connections. “I don’t think about it. I just do my own thing. I love what I do and there are certain things that come along with it that I don’t like, but it’s a part of my job.”

13. Tory Burch: Confidence

Tory Burch made her fortune helping women feel stylish and glamorous, so it’s surprising she would struggle with self-esteem. “Gaining confidence to really believe in myself was a big [challenge],” the designer told Charlie Rose. “I had an article written on our company, the first article. And a great friend called and said, ‘It was a great article, but you shied away from the word ambition.’ When I thought about it, she was absolutely right.”

14. Charles Schwab: Continuing to Innovate

Charles Schwab might be well into his seventies, but he’s not letting anything slow him down. In an interview with USA Today, he said, “The innovation that goes on is just profoundly important — it continues to be the engine that drives our future. If you’re not innovating, you’re going to go out of business fairly quickly.” In this fast-paced world, you’ve got to stay nimble and inventive if you want to survive.

15. Oprah Winfrey: Detractors

The queen of daytime television says one of the hardest weeks of her life was starting her new network, OWN — especially with detractors waiting for her to fail. “I certainly did not expect the velocity of schadenfreude — meaning people sort of lying in wait for you to fail, or make a mistake,” Oprah told ABC News. “I knew from the time I stepped in as CEO, the only way through is that you’re either going to have to end it, or you’re going to have to make some cutbacks now so you’ll be able to go forward.”

16. Michelle Phan: Sudden Fame

YouTube star Michelle Phan was an overnight success — and as you can imagine, she was a little unprepared for her newfound stardom. “Being overwhelmed was my biggest challenge. Growing up, I moved around a lot and didn’t make many friends,” she told Personal Branding Blog. “I was always the new girl, quiet and doodling all day in my notebooks. Now I had 10,000 friends overnight. I felt this incredible connection with people I had never met nor probably would never meet. But I felt like I knew them and it was both exciting and overwhelming.” With over 7.5 million YouTube subscribers, she certainly doesn’t have a hard time making friends now.

Read: Success Formula Behind Jenna Marbles, PewDiePie and Other YouTube Millionaires

17. Diane von Furstenberg: Every Day Brings New Challenges

Fashion designer Diane von Furstenberg learned early in life to roll with the punches. She told the Telegraph, “One thing that my mother did, and that is a habit in my life, is that when something unpleasant happens, somehow I deal with it, and then, because I deal with it, I’ve transformed it into something good,” she told The Telegraph. “People ask, ‘What are the biggest challenges in your life?’ I never know what to say, because every day’s a challenge and you just have to embrace it.”

18. Kevin O’Leary: Your First Business

Future venture capitalists take note: “To be a successful venture capitalist, you have to have started a business in the past,” “Shark Tank” investor Kevin O’Leary told Fast Company. “You need to have gone through the utter terror of getting started. I try to get my entrepreneurs to not make the mistakes that I’ve made in the past.”

19. George Foreman: Starting From the Bottom

George Foreman, the former heavyweight boxer-turned-entrepreneur, described making the transition in an interview with Personal Branding Blog.

“The biggest challenge in anyone’s life in making yourself a success is understanding that you are at the bottom,” Foreman said. “It doesn’t matter what business you come into. You start at the bottom and then you can go all the way to the top. But most people are afraid, especially celebrities and people that are already known. So many of us don’t want to start from the bottom because that is admitting that you have a long ways to go. The toughest step is to say, ‘I’m at the bottom and I got to go up.’ Even if you have a lot of money in your pocket, start at the bottom and you can only go up.”

20. Wolfgang Puck: Multitasking

A chef doesn’t just have to know his way around the kitchen. According to Wolfgang Puck, “A good chef has to be a manager, a businessman and a great cook. To marry all three together is sometimes difficult.”

21. Larry Ellison: Outgrowing Your Team

Larry Ellison, CEO of Oracle, explained that one of the hardest parts of his entrepreneurial career was letting go of some of the people that helped him build his billion-dollar company. “Suddenly we hit a wall. We reached a billion dollars in revenue, and we were having serious management problems all over the place,” he told the Academy of Achievement.

“The people who were running the company, the billion-dollar company, were the same people that had run the company when we were a 15 million dollar company, one-twentieth the size. I had an incredible sense of loyalty to those people who had worked with me to build Oracle. It was a very painful realization in 1990 that I was going to have to change the management team. The company had outgrown the management.”

22. Robert Herjavec: Inspiring Your Team

Like other entrepreneurs on our list, “Shark Tank” investor Robert Herjavec is a strong believer in the power of teamwork and leadership.

He told Business Insider, “If you can’t inspire the people around you, you are going to fail. If you can’t inspire the people around you, you should go sell real estate, because that is probably one of the only businesses where you could make a lot of money working completely on your own. But I think if you want to build a great business, you’ve got to bring other people along, and nobody wants to be managed. People want to be led.”

23. Barbara Corcoran: Fear

“Shark Tank” investor Barbara Corcoran said the biggest enemy of an entrepreneur is fear. “By the time you have 10 years under your belt, you start to realize how many near-death experiences you actually lived through, and it gets scary,” Corcoran told Leaders Magazine. “And it gets scarier the longer you go, because you know what you have to lose and that fear becomes your enemy. You’re no longer open to the universe and willing to trying a dozen things at once.”

24. Arianna Huffington: A Work-Life Balance

Arianna Huffington may run one of the largest and most successful media groups in the U.S., but she still understands the importance of a work-life balance.

“At this point, success, money, and power have practically become synonymous in the minds of many. This idea of success can work — or at least appear to work — in the short term,” she said.

“But over the long term, money and power by themselves are like a two-legged stool — you can balance on them for a while, but eventually you’re going to topple over. And more and more people — very successful people — are toppling over. To live the lives we truly want and deserve, and not just the lives we settle for, we need a third metric, a third measure of success that goes beyond the two metrics of money and power, and consists of four pillars: well-being, wisdom, wonder and giving.”

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