5 Successful Entrepreneurs Share The Most Important Lesson They Learned In Their 20s

Your 20s are a time for figuring out your place in the world.

Mistakes are unavoidable, but the truly successful learn from these setbacks and move on all the wiser.

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

Ben Casnocha, 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.”


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


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.”

Neil Blumenthal and Dave Gilboa, 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. 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.”

Ari Weinzweig, 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.

Sylvie di Giusto, 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 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.”



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