Mark Cuban, "Shark Tank" investor and owner of the Dallas Mavericks, learned that any limitations on personal growth are self-imposed.
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."
Neil Blumenthal and Dave Gilboa, co-CEOs of Warby Parker, learned that you should never cut corners.
Blumenthal and Gilboa cofounded hip, affordable eyeglasses retailer Warby Parker with Andrew Hunt and Jeffrey Raider in 2010. Last June, the company sold its millionth pair 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."
Jessie Goldenberg, founder of Nomad, says she learned that huge risks are sometimes worth taking.
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!"
Ari Weinzweig, CEO and cofounder of Zingerman's, learned that building a business requires a great deal of stamina.
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.
Melissa Carbone, CEO and president of Ten Thirty One Productions, learned the importance of being decisive.
Carbone got national exposure after Mark 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."
Sylvie di Giusto, founder of Executive Image Consulting, learned that a fancy degree and natural talent don't entitle you to success.
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 best and 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."
Shane Snow, author and founder of Contently, learned that you can't follow convention if you want to be exceptional.
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.
Mona Bijoor, founder of Joor, learned that there's no replacement for hard work.
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.
Jon Levy, founder of the Influencers, learned the importance of networking.
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."
Kristina Roth, CEO of Matisia Consultants, learned to be patient.
Roth founded Matisia Consultants in 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.
Will Pearson, cofounder and president of Mental Floss, learned that you should never keep your best ideas to yourself.
Pearson cofounded Mental Floss magazine, 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."
Beth Doane, founder of Raintees, learned that you need to hire people who are better than you.
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.
Kate McKeon, founder of Prepwise and Prepwise Games, learned that being a leader can be lonely at times.
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."
Ben Casnocha, tech entrepreneur and author, learned the importance of surrounding yourself with people who will push you to be better.
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."
