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Best Entrepreneurial Lessons

Best Entrepreneurial Lessons

Your 20s are a time for figuring out what you want from life.Mistakes are unavoidable, but the truly successful learn from these setbacks and move on all the wiser.

We asked entrepreneurs, including a few “Shark Tank” investors and the cofounders of popular retailer Warby Parker, to share the most important lesson they learned in their 20s.

Here’s what they said.

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Mark Cuban, a “Shark Tank” investor and the owner of the Dallas Mavericks, learned that any limitations on personal growth are self-imposed.

Mark Cuban, a Mario Anzuoni/Reuters

The billionaire investor made the biggest deal of his life when he sold his company Broadcast.com to Yahoo for $5.7 billion in Yahoo stock in 1999.

In his 20s, Cuban developed the all-encompassing self-confidence that’s made him successful. He learned that if he stopped making excuses and got to work, “with time and effort I could learn any new technology that was released.”

Kevin O’Leary, a “Shark Tank” investor, learned the importance of asking yourself the hard questions.

Kevin O'Leary, a Courtesy of Kevin O’Leary.

O’Leary’s second business, the software company Softkey, acquired The Learning Company in 1995 and then adopted its name. Four years later, “Mr. Wonderful” and his business partner Michael Perik sold the company to Mattel for $4.2 billion.

But even today, O’Leary says his true passion has always been photography.

As a young man, he spoke with his stepdad George about what he was going to do with his life. He realized that the key question for people starting out is, “What are you willing to do in order to be what you want to be?”

“It’s not enough to say you want to be a photographer, or an actress, or a writer,” he says. “You have to want to do all the necessary difficult things that are required to support that goal.”

He concluded that he wasn’t going to spend his 20s struggling to support himself as a full-time photographer. Now, supported by a career in business, he says, he has the luxury of being able to build a photo portfolio without financial concerns.

Jessie Goldenberg, the founder of Nomad, learned that big risks are sometimes worth taking.

Jessie Goldenberg, the founder of Nomad, learned that big risks are sometimes worth taking.Richard Feloni/Business Insider

Goldenberg graduated from NYU’s prestigious film program in 2010 and got a job working at CBS. It seemed as if her career path was set, but she considered the dream she had of opening her own fashion boutique. Lacking the funds or credit history to make such an investment, she instead raised money to start her own fashion truck, a mobile fashion retailer she named Nomad.

Nomad hit the streets of New York City in 2013 and Goldenberg says she broke even by the end of the year. She’s been successfully working on growing Nomad’s exposure and profits since.

“One thing I’ve learned is that your 20s are a time to take and embrace risks,” she says. “I’m living proof that it’s possible to be ‘livin’ the dream’ and be successful. With no family to feed and no dependents counting on you, your 20s are without a doubt the years to take a leap and pursue your passion!”

Neil Blumenthal and Dave Gilboa, the co-CEOs of Warby Parker, learned that you should never cut corners.

Neil Blumenthal and Dave Gilboa, the co-CEOs of Warby Parker, learned that you should never cut corners.Colin Hughes/Courtesy Warby Parker

Blumenthal and Gilboa cofounded hip, affordable eyeglasses retailer Warby Parker with Andrew Hunt and Jeffrey Raider in 2010. The company has sold well over a million pairs of glasses and is now expanding its brick-and-mortar business in addition to the ecommerce model that made it famous.

Blumenthal and Gilboa agree that part of the reason their young business has become so popular is because they learned every decision matters at every stage of your career.

“No matter what you’re doing, you should always try your best, especially early in your career,” they say. “How you do anything is how you do everything. No matter what task you’re faced with — large or small — always seek excellence.”

Lori Greiner, a “Shark Tank” investor, learned not to take business personally.

Lori Greiner, a “Shark Tank”/ABC

In 1997 Greiner started with a single invention, an earring holder, and grew it into a multimillion-dollar family of businesses with products on QVC and in the world’s biggest retailers.

When she met with a lawyer to file a patent for the earring holder, her husband Dan accompanied her because he had also invested his personal savings into Greiner’s fledgling business. The lawyer, with an air of casual misogyny, assumed that Dan was the real brains behind it all and spoke exclusively to him, Greiner says.

She confronted the lawyer and told him that she was done with the way he did business and angrily walked out of the room. While everything worked out for her, she says that she learned to not let events like that affect her confidence.

It’s why she says she tells all the entrepreneurs she works with, “Don’t let business get personal. It’s just business. Shrug it off.”

Greg Koch, the cofounder and CEO of Stone Brewing Co., learned not to sell himself short.

Greg Koch, the cofounder and CEO of Stone Brewing Co., learned not to sell himself short.Courtesy of Stone Brewing Co.

Koch and Steve Wagner cofounded Stone Brewing Co. in 1996. As of last year, Stone is the ninth largest craft brewer in the US, the largest in Southern California, and the first American craft brewery to open and operate a brewery in Europe. Its beers have earned it the title of “ All Time Top Brewery on Planet Earth” from the readers of Beer Advocate.

As he grew into the role of CEO, Koch learned the importance of being firm. And as he expanded the business, he realized it’s necessary to always take three bids from different contractors to get the best deal.

As a boss, he listened to his father’s advice: “You can never fire anyone too soon.”

Mona Bijoor, the founder of Joor, learned there’s no replacement for hard work.

Mona Bijoor, the founder of Joor, learned there's no replacement for hard work.Mona Bijoor

In 2010, Bijoor started Joor as an online global marketplace for wholesale buying for fashion retailers. It is based in New York City and now has offices in Los Angeles and Milan.

After getting her MBA from Wharton in 2005, Bijoor worked as a consultant before moving into fashion.

“Work ethic is put down these days,” Bijoor says, acknowledging the shift in popular culture toward prioritizing health and well-being over all-nighters and few days off. “But looking back, it gave me the extra edge in a lot of situations and was the training I needed” to start a company.

Philip Krim, the CEO and cofounder of Casper, learned that leaders need to take responsibility for their entire company.

Philip Krim, the CEO and cofounder of Casper, learned that leaders need to take responsibility for their entire company.Casper

Krim began developing his mattress delivery business, Casper, with cofounders Gabriel Flateman, T. Luke Sherwin, Jeff Chapin, and Neil Parikh in 2013. The companyhas raised a total of $70 million in venture capital from top investors.

Leading a growing company taught him that he needed to learn from others but ultimately trust himself.

“When you launch a company, every day is a minefield of challenges,” he says.

He realized that, “Everyone has their opinion, their experience at a previous startup, and a success story. But at the end of the day, it’s your company. Trust your gut.”

Sylvie di Giusto, the founder of Executive Image Consulting, learned that a fancy degree and natural talent don’t entitle you to success.

Sylvie di Giusto, the founder of Executive Image Consulting, learned that a fancy degree and natural talent don't entitle you to success.Executive Image Consulting

Di Giusto worked in human resources for more than 20 years before starting Executive Image Consulting in 2009. She’s helped individual executives look their bestand has consulted for companies like McKinsey, BMW, and Thomas Cook.

She was humbled early in her career.

“I spent my 20s in corporate environments, and I remember them for working nights and weekends,” she says. “Sweat, hassle, pain, as well as diligence, perseverance, and an enormous amount of effort and energy characterize my career at this point. I’ve learned that there are very little short cuts when it comes to career success. Success doesn’t ‘just happen.’ Never.”

Alan Doan, the cofounder of Missouri Star Quilt Co., learned that the first step to becoming an entrepreneur is gaining self-confidence.

Alan Doan, the cofounder of Missouri Star Quilt Co., learned that the first step to becoming an entrepreneur is gaining self-confidence.Missouri Star Quilt Company

Doan founded Missouri Star Quilt Company in 2008 with David Mifsud and his sister, Sarah Galbraith, as a way to dominate a niche market, and it’s worked. Doan and Galbraith were named Small Business Owners of the Yearby the Small Business Administration this year for the company’s rapid growth — revenue grew from $1.7 million in 2011 to $10 million in 2013 — and commitment to revitalizing its home community.

When Doan was 25 and wondering if he should start his first business, a mentor of his named Bill Neal told him, “If you don’t have the confidence to go toe to toe with the owners of other companies and trust your instincts over theirs, you’re not ready yet.”

Doan decided to take a job and discovered that he was “just as clueless as the guys running other companies” and so decided to build his own. “By the time I did,” he says, “I was confident I had as good a shot as everyone else and trusted myself then to go build something that was great.”

Ari Weinzweig, the CEO and cofounder of Zingerman’s, learned that building a business requires a great deal of stamina.

Ari Weinzweig, the CEO and cofounder of Zingerman's, learned that building a business requires a great deal of stamina.Courtesy of Zingerman’s

Weinzweig cofounded Zingerman’s Deli with Paul Saginaw in 1982, and today it’s one of nine businesses in the Zingerman’s Community of Businesses. They’ve used a unique management philosophy that emphasizes collective decision-making to continually grow their company, which had $50 million in revenue last year.

Weinzweig has written three detail-packed books on his leadership and business philosophy, but says the main takeaway from his 20s is that building a successful business requires unwavering determination.

“Resilience, collaboration, willingness to stay the course, emotional and physical stamina, positive energy are all key,” he says.

Kristina Roth, the CEO of Matisia Consultants, learned to be patient.

Kristina Roth, the CEO of Matisia Consultants, learned to be patient.Courtesy of Kristina Roth.

Roth founded Matisia Consultantsin Seattle in 2006. Last year her firm brought in over $60 million in revenue and has worked with several Fortune 100 companies. Roth recently opened an office in Los Angeles and is planning an expansion into San Francisco.

She says that when she was younger she felt like she had to achieve all of her goals as soon as possible, an anxiety-inducing mindset that was actually counterproductive.

“In my 20s, I learned the concept of delayed gratification and that you need to pay attention to important decision points in the tree of life, which will change your life one way or the other,” she says.

Jon Levy, the founder of the Influencers, learned the importance of networking.

Jon Levy, the founder of the Influencers, learned the importance of networking.©2014 Rick Smolan/Against AllOdds

Levy is an independent marketing consultant, but is most notably the founder of the Influencers, a network he started in 2009 that today has over 400 members. Twice a month, he invites prominent people ranging from Olympic athletes to Nobel laureates to his sprawling New York apartment to share a dinner followed by a series of presentations from notable figures like Bill Nye the Science Guy.

As he saw his personal life and career improve the more he surrounded himself with impressive people from a wide variety of fields, he learned the importance of having a strong network, which he says is best explained in “Connected” by Nicholas A. Christakis and James H. Fowler.

“The people you surround yourself with have a direct impact on your success and failure,” Levy says. “They will affect everything from how much you exercise and what clothing you wear to how much you earn and what values you deem important. So if you want to live a life full of joy and accomplishment, you need to become masterful at building relationships with good people you respect, and letting go of relationships that have a negative impact.”

Melissa Carbone, the CEO and president of Ten Thirty One Productions, learned the importance of being decisive.

Melissa Carbone, the CEO and president of Ten Thirty One Productions, learned the importance of being decisive.Courtesy of Melissa Carbone.

Carbone got national exposure afterMark Cuban invested $2 million in exchange for 20% of her horror attractions company Ten Thirty One Productions in the fifth season of “Shark Tank.” Her company brought in $3 million in revenue last year, and this year she plans on expanding her Haunted Hayride and other spooky events out of Los Angeles and into New York, San Francisco, and Atlanta.

Carbone learned that she couldn’t be a leader if she mulled over a decision for too long or continuously looked for counsel.

“Use your best judgement and just make a decision,” she says. “It may not always be the right one, but that’s OK. A wrong decision is better than a demeanor of uncertainty. A good and swift decision-maker will gain the trust and buy-in from employees, business associates, and customers/clients because it will illustrate confidence. Decision-makers are leaders.”

Shane Snow, an author and the founder of Contently, learned that you can’t follow convention if you want to be exceptional.

Shane Snow, an author and the founder of Contently, learned that you can't follow convention if you want to be exceptional.Shane Snow

Snow cofounded Contently, a platform that connects freelance writers to major brands like Coca-Cola and GM to deliver content, in 2010. He also recently published his first book, “ Smartcuts.”

Snow spent his 20s building a business and working with other entrepreneurs, and he noticed that “doing things the way they’ve always been done is asking for mediocrity.”

“The best entrepreneurs and workers and artists — and people, really — ignore convention and find smarter paths,” he says.

Beth Doane, the founder of Raintees, learned that you need to hire people who are better than you.

Beth Doane, the founder of Raintees, learned that you need to hire people who are better than you.Beth Doane

In 2008, Doane created Raintees, an apparel line that plants a tree in an endangered rainforest for every shirt sold and donates school supplies to a child in need for every tote bag sold. Raintees works with nonprofits in over 20 countries.

Doane learned in her 20s that the best entrepreneurs set aside the egotistical drive to micromanage and instead build great teams.

“If you really want to reach your highest potential, you have to consistently surround yourself with people who challenge you, who are strong where you are weak, and work just as hard or harder than you do,” she says.

Ben Casnocha, a tech entrepreneur and author, learned the importance of surrounding yourself with people who will push you to be better.

Ben Casnocha, a tech entrepreneur and author, learned the importance of surrounding yourself with people who will push you to be better.Ben Casnocha

Casnocha spent his 20s starting several tech companies and most notably connected with Reid Hoffman, the billionaire chairman and cofounder of LinkedIn. Casnocha pitched Hoffman on becoming his “chief of staff.” In the role, he helped manage Hoffman’s priorities across LinkedIn and his venture capital firm Greylock. They have since cowritten two books together.

Casnocha recently wrote about the main lessons he learned from Hoffman, and says the most important one is “that you are the average of the five people you spend the most time around. You really are the company you keep.”

Will Pearson, the cofounder and president of Mental Floss, learned that you should never keep your best ideas to yourself.

Will Pearson, the cofounder and president of Mental Floss, learned that you should never keep your best ideas to yourself.Courtesy of Will Pearson

Pearson cofounded Mental Flossmagazine, a publication dedicated to fun history and trivia, with Mangesh Hattikudur when they were students at Duke University in 2001. They sold a stake in the company to Denis Publishing in 2011 and are now dedicated to growing their brand’s global image and their profitable ecommerce business.

When he was starting out, Pearson learned that it’s impossible to predict how you’ll catch your break, so you shouldn’t limit who you speak with.

“Early on, we had this meeting with the CEO of one of the largest publishers in the world and we left the meeting feeling pretty good,” he says. “Later that day, we ended up having dinner with a family friend/stay-at-home parent where we casually discussed our business and goals for the future. It’s amazing how people really do conspire to help you, and to our surprise, it was the conversation with that stay-at-home parent that dramatically changed our lives when she put us in touch with one of her best friends, who happened to be the CEO at a different publisher.”

Kate McKeon, the founder of Prepwise and Prepwise Games, learned that being a leader can be lonely at times.

Kate McKeon, the founder of Prepwise and Prepwise Games, learned that being a leader can be lonely at times.Kate McKeon

McKeon was a longtime consultant who turned to the education world when she became an instructor at Manhattan GMAT in 2008. In 2012, she founded her own test prep company, Prepwise, for students taking the SAT and GMAT.

In her 20s, McKeon learned that there will be times when you are simply more ambitious than your team members and there’s nothing you can do to change them. It’s a lesson that carried over into her entrepreneurial ventures.

“A lot of people just go to jobs and aren’t all that interested in digging in to do the work necessary to reach the next level,” she says. “This is really important to consider when structuring teams and planning staff — most of your employees will be nothing like you. That has to be factored into your plans if you really want to grow, so you can plan realistically. Your version of ‘take initiative’ won’t be replicated by your staff.”

Web Master

February 13th, 2018

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