5 Things the Most Successful Entrepreneurs Do Every Day

Written on January 26, 2017
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The numbers don’t lie: Most businesses fail. There are some 29 million small businesses in the United States, according to the U.S. Bureau of Labor Statistics, and roughly 18,000 companies with 500 employees or more. But half of those firms disappear within five years of starting up, and after a decade, only one-third remain standing.

Fighting against the statistics are thriving, successful entrepreneurs. How do they do it? How do they keep their businesses growing? We got some tips from business owners, who let us in on five things they do every day to keep their companies going upwards.

Entrepreneur to Entrepreneur: Everyday Tips

Threadless, the Chicago-based company that crowdsources t-shirt designs, generates an estimated $30 million annually in sales, with a profit margin of 30%. Jake Nickell, the company’s co-founder, has a net worth valued at $50 million. But Nickell’s story is riddled with tales of small steps—and long periods of stagnation—that led, ultimately, to success.

Always see the fun in the serious side of business

A business that sells millions of t-shirts every year began in Nickell’s apartment in 2000, with a Tupperware container full of t-shirts under his chair. He launched Threadless as, well, a thread on an online forum called Dreamless, a collective of artists from around the world.

“I started a thread saying, ‘Post designs here and I’ll make the best ones into t-shirts and poster we can all have,’” says Nickell.

But Threadless remained a hobby for Nickell for years. Nickell dropped out of school at the Illinois Institute of Art. Web developer jobs came and went. Threadless remained in the backdrop. As Nickell started building websites, he would use Threadless as proof that he had the chops as a web developer.

Finally, six years after launching Threadless from his apartment, Nickell realized he was generating more income from the sale of t-shirts than from his client work.

Nickell’s secret, at least in part, is that Threadless has always remained a fun project for a good cause.

“We think of ourselves as a sort of non-profit that’s out there to help artists monetize their work,” says Nickell. “And thinking of ways to do that has been a lot of fun.”

The company still curates the best t-shirt designs. But these days Nickell is focused on other aspects of the company. Threadless recently opened a platform called Artist Shops that lets any artist start their e-commerce site using Threadless’ backend—the manufacturing, order fulfillment, customer service.

One secret to Nickell’s success? “If it was just about selling t-shirts day after day, I’d be bored with it,” says Nickell. “I try to keep it fresh and do fun, new stuff all the time.

Keep a culture that matches the company—and the employees

He also keeps the atmosphere at Threadless laid back. The office, Nickell says, is not as intense as other startups.

“Everybody in the company reports to about five people,” says Nickell. “I’m tight with them, which helps with trickling down everything, including the mission of the company and the direction we’re headed in.”

Day by Day Tinkering: Life as an Entrepreneur

Unlike Nickell, Melissa Llarena, founder of Career Outcomes Matter, did not start her business in her apartment. Her profitable career coaching practice started in a midtown New York City outlet of Le Pain Quotidien. It’s a messy tale that sums up what it’s like to be a mother and an entrepreneur.

“I was pitching a prospect while baby-wearing my first son,” says Llarena. “My son pooped on this prospect’s wife, and despite the mess, I successfully closed the deal.”

Today, Llarena’s clients include dozens of director-level and above employees at Fortune 1000 companies. She helps them position themselves to assume some of the most competitive leadership positions by dissecting and delivering the perfect job interview.

It’s a far cry from Llarena’s beginnings, which included stints in investment management, Internet marketing, and employment law. But this early exposure to executives and various functions showed her the business world from different angles. It’s something she leverages today for her clients, who rely on cross-functional relationships.

Adopt routines to save the tough decisions for the business

Llarena’s success would be impossible, she says, without some basic habits she does not veer from. First off, she plans 24 hours in advance. With three sons, the only way to survive, she says, is to plan the night before. Then there’s the oatmeal. Llarena eats oatmeal every day of her life. She doesn’t like to have to make so many decisions in the morning, and with oatmeal a constant, she doesn’t have to worry about what she and her sons will eat in the morning.

Plan the day around your best times

Mornings are crucial for Llarena. She knows that between 9:30 a.m. and 11:30 a.m., she will be alone and alert. That’s when she schedules the bulk of her client calls.

Never lose sight of your goals

Ultimately, though, Llarena attributes her business success to her sons’ future.

“I’m working for myself and to build a legacy that can carry my sons further than anyone has gone in my family,” says Llarena. “I deal with the lack of sleep. I deal with rejection. I can deal with a lot. I can’t say it would be this possible or doable if I were building someone else’s dream.”

Alfonso Serrano

Alfonso Serrano is a Brooklyn-based writer. He has served as a senior editor at Al Jazeera America, TIME.com and Conde Nast Portfolio, among other publications. His writing and commentary have appeared in The Guardian, National Public Radio, The Chicago Tribune, and Pacific News Service.
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