How today’s young entrepreneurs approach business a bit differently 

By Chris Wallace

Not that long ago, it was accepted practice for CEOs and top executives of highly successful companies to wear finely tailored suits and top dollar outfits to important meetings. And those meetings were typically held in meticulously designed boardrooms that either subtly or blatantly flaunted the business’ success. But ever since the dawn of social media success stories and the explosion of 20-something multi-millionaire entrepreneurs, those traditions have been turned on their ears.

While Mark Zuckerberg’s “hoodiegate,” where the 28-year-old billionaire arrived at an IPO presentation to Wall Street in a black hoodie, was considered a sign of immaturity ( by some, others saw it as a mark of creative self-expression. Meetings for some of the most financially successful businesses in the world are now being held in rooms with cozy couches, arcade games and posters of Mario Brothers on the walls.

It’s the beginning of a change. As more successful businesses are springing from the minds of younger and younger entrepreneurs, what is considered standard is becoming a way of the past. Here we look at how some of the most successful young industrialists of the day are tackling the business world in their own way.

While Instagram founders Kevin Systrom, 28, and Mike Krieger, 27, put an incredible amount of work into their photo sharing application, they also know that it’s who you know that makes a difference. Systrom, a graduate of Stanford, was an intern at the company that would later become Twitter and was also an employee of Google. Additionally, his participation in the Mayfield Fellowship program, a work-study program for budding entrepreneurs, put him in touch with many of the people they would need to know while creating and launching Instagram. Thanks to a chance meeting at a party in January 2010, Systrom and Kreiger received an investment of $250,000 from Steve Anderson, founder of Baseline Ventures. Ten months later, Instagram launched and two years after that, it sold for $1 billion to

Gurbaksh Chahal dropped out of school at 16 and started an online advertising business based on the idea one-click connections called ClickAgents. In two years he sold it for $40 million. Without missing a beat, he launched a new online advertising network called BlueLithium that sold in only three years to for $300 million. Now 29, Chahal is working on a new ad network company, RadiumOne, which utilizes online social data.

Andrew Mason, 31, was a music major who just wanted to do some good. While in school, he built databases for business tycoon Eric Lefkofsky and with Lefkofsky’s backing, began a social outreach company called The Point. Users would basically get together on the site and try to find ways to make the world a better place. One group, Mason noticed, thought that they would try to save money by getting 20 users to buy the same product and see if they could get a discount. At first Mason and his colleagues dismissed the idea since their purpose was not about money making, but with the stock market crash in 2008, they decided to expand on the idea. The Point soon evolved into Groupon and today, Mason’s net worth ( is approximately $1 billion.

Angelo Sotira, 30, began his foray into the social media scene when social sites were still in their infancy. At age 12, he manipulated an online chat room, The Netherworld, into a regionally popular video game. While still in high school, he launched DMusic, a site where independent musicians and fans could trade music and upload songs. The company was purchased in 1999 and Sotira was hired fresh out of high school to run community outreach and the daily blog. When that company folded, Sotira put $15,000 of his own money into launching deviantArt with Matthew Stephens and Scott Jarkoff, and the rest is history.

Dennis Crowley, now 36, grew up in a family that loved games and that spirit carried him through some difficult times following college. After his employer, mobile company Vindigo, let him go during a series of layoffs, Crowley struggled to find employment in New York City. He eventually applied for graduate school and was accepted into NYU’s ITP program. Here he began working with fellow student Alex Rainert who encouraged him to put more work behind his website, Together they developed the site, which encouraged users to “check-in” to various businesses when they arrived, and the site was eventually acquired by Google. But Google didn’t give the site room to breathe, so Crowley began working on a new alternative. With the help of an iPhone app-savvy friend, Naveen Selvadurai, they developed what is now known as FourSquare, a company recently valued at close to $1 billion.

The overarching theme for each of these young entrepreneurs is that they had a passion and they weren’t afraid to follow it. Whether or not others frown on their choice of attire or place of business, what matters is that they are doing what they love and they’re making real money at it. So the next time someone tells you that you need to “dress for success,” consider how these young entrepreneurs are turning the tide of socially acceptable business norms and how dress matters less than following through with your passion.

Guest Post By: Christopher Wallace is Vice President of Sales and Marketing for Amsterdam Printing, a leading provider of custom pens and other promotional products such as imprinted apparel, mugs and customized calendars. He regularly contributes to Promo & Marketing Wall blog.