How Entrepreneurs, Such as Daymond John, Learn to Improve Their Game

Startup life is fraught with peril, but it's one space where prior experience really helps. These business owners share how their business expertise evolved.

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By Laura Schaefer

Opinions expressed by Entrepreneur contributors are their own.

There's something addictive about entrepreneurship. Successful business owners can emerge after several stints on the startup roller coaster, including some previous outings that did not result in wins.

Still, entrepreneurs who eventually succeed often find value in their flops. "Failure humbles you," Fubu founder Daymond John shared via a voice message. It "also tests you and makes you sure you are cut out for the responsibilities of being an entrepreneur," he added, noting failure is "a clear report card on what you did right and what you did wrong."

Some who may fail are "people who start off with a large amount of money," said John, who is also an investor on ABC's Shark Tank. "They believe the money itself is going to create the business, and they don't have any proof of concept, meaning any actual customers or sales."

Related: Shark Tank's Robert Herjavec on Great Business Pitches and Why Sales Reps Need to Be Chameleons

Who does the Shark think are the entrepreneurs destined to succeed? "The ones that have a long history in the business or the market so they've made a lot of mistakes or they've seen a lot of mistakes and have a network to rely on."

Also well positioned are "those that have mentors who do not have an investment or interest in the business who can give them the right guidance when they're about to go off track," he said.

The entrepreneurs who meet success can be "those that, by grit, have created some type of following," John added. "They didn't just throw a bunch of money out there. They sold something. They went back to the customer, resold it, and/or fixed the product and now have a perfect product."

The startup world is one space where practice can make perfect. Here's a roundup of wisdom from some lesser-known entrepreneurs who've persevered and their take on what sets a current success apart from past, er, "learning experiences."

Related: The Key to Creating a Successful Startup Around Your Passion

Pursue a passion. The critical difference, for some entrepreneurs, is passion. "My failed businesses sounded like good ideas at first, but the big difference was that I was always thinking about my successful businesses when I woke up and went to bed," Tom Corson-Knowles, founder of TCK Publishing in Bloomington, Ind., shared by email.

Focus the enterprise. "I've been in business for nearly 20 years, and the key thing I've learned is be focused," wrote Rich Dale, CEO of Belfast-based Flowlens, by email. When he began his web design and development company in Northern Ireland, the staff "tried to be 'all things, to all people' and take any client opportunity that came along."

A new business owner should figure out where the company's strengths lie and not to succumb to scope creep, according to Dale. "If an opportunity does not fit your strategy," he wrote, "you can say no without remorse, knowing that it will not slow you down. Being focused has allowed us to accelerate the growth of our business, and as a result reap the rewards."

Related: Eager to Start Another Business? 6 Things You Need to Keep in Mind.

Tackle problems you understand. Yarin Kessler, founder of PDF Buddy, a New York City company providing an online PDF editor, noted by email that he had tried to launch previous startups before meeting with success. "The best business ideas are the ones that tackle the pain points you have personal experience with," he wrote, adding that making assumptions about others' needs, especially in unfamiliar industries, is not a recipe for success.

Kessler's prior business attempts tackled areas he wasn't well versed in. "They all failed because the problem set was too foreign, which meant I wasn't addressing the right issues," he wrote.

Take the airplane test. Sam Rosen, the CEO and founder of MakeSpace, a New York City startup that offers storage container pods, shared that his current enterprise has raised more money than a prior venture. "One of the biggest reasons why I stopped working on SpeakerGram was because my business partner and I were literally sick of one another by the end," he wrote by email.

Rosen currently uses an "airplane test" for employees: "Could I jump on a cross-country flight with the prospective partner?" And then "turn around immediately and take the next flight back, and not get sick of them?" he wrote. "Would we have enough to talk about the whole way? Not only can Rosen see how candidates deal with stressful situations, he credited this approach with helping him select two business partners and build a team of nearly 30 employees for MakeSpace, which has received venture capital backing.

Related: Looking for an Edge for Your Startup? Call in the Sharks.

Be committed. Some entrepreneurs gain momentum after taking concrete steps like leasing an office. "The minute I got an office space, it was a game changer," wrote Tena Lynn Pettis, founder of marketing firm Tenacious Edge, based in St. Paul, Minn. "I had to pay for something; I had a lease and there was no turning back. I was in this whole entrepreneur thing for the long haul! Since then I have a handful of employees and we just moved into a larger space this past month."

Maintain a learning mind-set. A common regret of leaders of failed startups is their loyalty to a product or service that isn't connecting with users. "I launched my first business at the age of 22 and since then have founded three more," wrote Violette de Ayala, founder of Femfessionals, a company offering a business-networking service for women that is based in Miami.

"Be flexible with the business model and services you offer," she added. "You will most likely have to modify features, pricing and quite possibly the one item you thought would be the "hot ticket.' Listen to your clients."

Regardless of the type of business, "love what you do," John advised. "Surround yourself with a team of advisors [who] have the same agenda. Do homework. Research every single thing that you are doing. Take affordable next steps. Take a step forward, learn and then repeat."

Related: Why Serial Entrepreneurs Aren't Actually More Successful The Next Time Around

Laura Schaefer

Writer and Co-founder,

Laura Schaefer is a web content writer and co-founder of Madison, Wis.-based, which offers writing and editing services to professionals and students. She is also the founder of Madison-based Planet Explorers Publishing, which produces ebook travel guides for readers aged 8 to12.

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