Categories: Entrepreneurship

What Successful Entrepreneurs Do More Than You: Fail

There’s a myth out there that successful entrepreneurs like Elon Musk (Tesla) and Jeff Bezos (Amazon), among others, all saw their ideas come to fruition the first time around. If you believe that, you’re sorely mistaken, because seeing success in entrepreneurship takes trial and error, patience and refining an idea to adapt — which is what both Musk and Bezos, along with other successful entrepreneurs, have done.

One of the first business ventures I launched was a spring break sports event, working with a major spring break vacation company. The company was going to send my brochures to every student they signed up, guaranteeing that my event would get tons of free exposure and I’d have lots of signups. Unfortunately, I made the mistake of trusting my partner.

I didn’t ask if they had mailed out my brochures. I didn’t ask when they were mailed. I didn’t ask which employee handled the mailing. When I got to Daytona Beach, I found I didn’t have hundreds of signups. I had three. I ended up losing my company because I trusted a partner to keep their end of the bargain and I didn’t take basics steps to check on their progress.

The good news is I never made that mistake again with a partner, vendor or employee again. I never assume someone will deliver my goods on time without my checking up on them early and often. Over the years, I’ve prevented several more disasters because I, not only caught problems before it was too late, but I also had a Plan B in place.

That mistake that I made early on in my career — trusting people to take care of parts of my business — taught me a valuable lesson, and I now use the same method for preventing missed deliverables from ever happening again.

Successful entrepreneurs almost always fail more than once before they succeed. They are risk takers and aren’t afraid to fail. Type “Don’t be afraid to fail” and “entrepreneur” into Google and see what you get. You’ll get lots of results that show top business people talking about how their failures made them successful. Entrepreneur magazine even goes so far as to say that just the fear of failure can doom your business.

So, think you’ve got a million- or billion-dollar idea just waiting to launch but have run into some roadblocks? Or are you just afraid of failure altogether? We give you some tips on how to overcome such thoughts, why playing it safe with work will stall your career and what types of risks you can take that won’t derail you permanently.


When you volunteer, you’re often joining a group outside your area of expertise — or you would have been asked to join already. If your company is asking for volunteers to form a safety committee or come up with an idea for a charity event or work a fundraiser, jump in. The less you know about the task, the more risk you’re taking. That means you’ll be more careful in what you say and do. That will lead to your doing more homework and making sure you dot every “I” and cross every “t.” If you make a mistake during a fundraising meeting, it’s not going to kill your career.

Forget The Myth Of The Overnight Success

Steve Jobs. Jeff Bezos. Bill Gates. Elon Musk. Thomas Edison. Mark Cuban. Richard Branson. Leonardo da Vinci. None of them got it right the first time. Each time they failed, they learned how to do something better the next time.

An old joke involves Thomas Edison replying to someone who pointed out that it took him 1,000 tries to make the light bulb. Edison said he never failed, he simply learned 999 ways not to make a light bulb.

Steve Jobs was replaced as CEO of Apple because, while he was a computer genius, his investors felt he didn’t know the nuts and bolts of running a business. He came back years later after starting another company (NeXT), and, with his newfound experiences, saved Apple from ruin and turned the company into a legendary business.

Many believe that Elon Musk is nearing the edge of failure with Tesla. Do you really think we’ll hear the end of him if the car company fails? He may take what he learned about making batteries and start an even bigger green energy company.

Even the latest pop star you see soaring to the charts probably spent years testing material in clubs and had one or two albums that went nowhere. You need to learn to walk before you can run, and when you’re learning to walk, you will inevitably fall down a few times — which is a lesson all successful entrepreneurs have come to understand.

Try Starting A Micro Business

No matter how crushed you are at work, you probably still have time to try starting a business. Most often, these are online businesses like a website or blog with AdSense ads. Hell, you could also always offer your services as a consultant, because you’ve got skills outside of your day-to-day career.

Starting a small business will teach you a ton about marketing, finance, using website analytics and other business skills. If your blog or e-commerce site or consultancy tanks, who’s going to know if you don’t tell anyone about it? This is a great way to manage a (possible) failure without seriously damaging your finance or career.

Write A Business Plan

You don’t have to start a business just because you’ve written a business plan. Even if you have no intention of starting a new business, writing a business plan for a larger company than you can launch and run right now is a great way to get feedback on your abilities as an entrepreneur. Have others read your plan for feedback. You might be hugely disappointed when person after person says, “This won’t work,” or tell you that you need to make massive changes. Getting these types of rejections from other entrepreneurs, CEOs and potential investors will teach you more than any B school class you ever took.

Take A Tough Night Class

One of the ways to boost your skills is to increase your knowledge, specifically by attending workshops, getting certified, taking some online classes for career help and/or attending some night school courses. Don’t be afraid to sign up for a course that you’re pretty sure won’t be an easy A — or any kind of A. Even if you end up getting a C (or worse), you’ll still learn something, and, more importantly, find out one of your weaknesses. If you really can’t master this subject, you’ll learn that you need to understand who the players are in this area, how to work with them, how to eventually hire them and how to manage them.


Public speaking is a serious fear for many people, including highly successful entrepreneurs. If you want to start your own company and take it to great heights, you’re going to have to use your personality to sell your dreams to others. You’ll need to convince investors. You’ll need to motivate employees. You’ll need to charm the media. You’ll have to make sales presentations, unveil new products and seek financing. You’ll need to do this on video chats, via webinars, in person, over podcasts and via marketing videos.

Look for a local Toastmasters chapter in your area to get free or low-cost help and group support with your public speaking. Volunteer to make in-house presentations to your team. Get on the meetings and continuing education committees of your industry’s or profession’s trade association or professional society and ask to introduce speakers, then sit in on panel discussions, moderate panels and, finally, give presentations.


One way to build your personal brand and climb the corporate ladder is to get published in professional trade magazines, newsletters and journals. Even if you hate to write, aren’t good at it and are worried about looking foolish, try to get published — plus, you can read some of our writing tips to help.

First off, no quality magazine or website is going to publish bad material. You’ll work with an editor who will talk to you about your content and sources. If you’re not a great writer, but have some subject matter expertise and an interesting story, the editor might offer to have someone ghost write the article for you. You might be able to hire a friend who’s a good writer to help you write the piece. You can ask a co-worker to proofread or edit your article.

If You Haven’t Failed, You Haven’t Tried

No one makes millions or influences others without first making mistakes. If you, somehow, manage to charm your way into a high-profile, high-paying job without ever making a misstep, guess where you first big error is going to happen? In the spotlight. And those are the types of mistakes from which you can’t recover.

Write a list of tasks you can undertake that can help your career, involve some risk, but which won’t tank your image if you come up short. If you become a CEO someday, or you own your multi-million dollar, you’ll probably join the ranks of successful entrepreneurs who have multiple failures to joke about — along with motivational advice to give young people coming up behind you.

All images via Getty

Steve Milano

Steve Milano is a journalist and business executive/consultant. He has helped dozens of for-profit companies and nonprofits with their marketing and operations. Steve has written more than 8,000 articles during his career, focusing on small business, careers, personal finance and health and fitness. Steve also turned his tennis hobby into a career, coaching, writing, running nonprofits and conducting workshops around the globe.

Published by
Steve Milano

Recent Posts

When Job-Hunting, Screw Online Applications, Email Everyone You Know Instead

Job-hunting sucks. There, I said it. And, chances are, it's something you've all thought plenty…

2 years ago

The Most Successful Sports Agents And How They’ve Made Their Mark

Thanks to movies like Jerry Maguire, the idea of becoming a professional sports agent is the…

2 years ago

Emergency Money Fund: Questions And Answers

Unexpected financial drains are the worst, aren't they? Just when you've seemed to straighten out debt,…

2 years ago

How To Build Wealth And Avoid Dumb Money Mistakes Like A Rich Person

Ever wonder how the rich seem to get richer, while you live paycheck to paycheck?…

2 years ago

The Best Credit Cards For Rewards (And Finding The One For You)

For every dollar you spend on a credit car, you should be getting something back…

2 years ago

Unusual Workplace Perks We’re Jealous Of

We’ve all heard of trendy perks like office kegs and ping pong tables. As cool…

2 years ago

This website uses cookies.