How Did Dungeons & Dragons Geeks Take Over Wall Street?

From 1995 through 2000, Wall Street was flooded with an army of twenty-somethings eager to prove that the Internet was the new frontier for business. The ubiquitous image of the Internet guru with a shaven head, a pierced ear, and a goatee, dressed from head to toe in black, was harshly juxtaposed against the New York Stock Exchange traders dressed in conservative suits and the daily power tie. Two completely different cultures were coming together for the very first time.

Creative types were taking over Wall Street,
and I was one of them.

Awkward moments of weirdness were a daily event at the local deli counters as the suits gave Internet-savvy graphic designers the once-over. These vagabond-looking young people standing in line at the Au Bon Pain on Broad Street, with their tattoos and piercings, were the very young people whom the Wall Street Journal was following every day.

This was a time when venture capitalists suddenly lost their minds and handed out billions in start-up capital to the first Gen Xer who shouted, “It’s the new economy, man; you just don’t get it!” The geeks who used to get teased for playing Dungeons & Dragons and being early adopters of everything computerized were now speaking in code like the Oracle at Delphi. And the funny thing was, Wall Street was listening.

Investors threw money at anyone who designed websites, and K2 was the first to do it well. Many of the trends during the first dot-com era made no sense, but as a long-time entrepreneur, I made a decision that made total sense: question everything with the detachment of a seasoned interviewer and the keen eye of a hardened reporter. Since our business models were changing overnight, the best course of action seemed to be to just observe and not judge. “Figure out the model and adapt to it” became my motto.

Sometimes it seemed I was seeing the entire world change before me. Everywhere I went in Manhattan there was electricity in the air and something strange taking place—young, savvy, creative types were dabbling in big business, handling their careers with the strategic focus of a hardened battlefield general.

It was becoming apparent that this up-and-coming generation was different from mine.

It also explained why the Wall Street Journal, Barron’s, and the New York Times were covering their every move. This new wave of twenty-somethings coming out of college didn’t seem to want a job; they wanted to start companies and decimate the way their parents worked. They weren’t satisfied with forty years in a cubicle and a gold watch at retirement. It was obvious to me that this generation wanted a different experience, and they knew it was there for the taking.

The truth is, this young workforce is just like any other generation that came before them—cocky, resentful, bold, and defiant. The only difference is, Generations X and Y have a skill set that Baby Boomers didn’t have, and suddenly that skill is in demand. For the first time in history, youth has money, power, freedom, and media attention. And they exercised that power for the first time during the dot-com boom.

HTML programmers were demanding $85,000 a year despite the fact that the code could be taught to a kindergartener. Secretaries wanted stock options before they would even consider an interview. Salespeople wanted to be assured that if they brought in the business, they wouldn’t get just commissions but equal partnership. If you didn’t give in to their demands, they went to the competition to reveal your supersecret proprietary system. And there were plenty of companies that would give them all that they asked for and more.

The history of Wall Street was being rewritten as the first wave of Millennials became Internet paper millionaires. To Baby Boomers like myself who had grown up on solid, tried-and-true textbook business ideologies, this made no sense. Why was Wall Street going gaga over a few kids with an Internet company? It was just graphic design in a new medium. Yet despite business plans being scribbled on cocktail napkins, and questions about profitability being met with vitriolic cynicism from the techno wunderkinds, venture capitalists were writing big checks.

The old career norm of getting a job after graduating from college, working your way up the ladder over ten to fifteen years, buying a house, getting the corner office, and then retiring was being replaced by a system of young, tech-savvy entrepreneurs starting their own companies immediately after college. These Internet entrepreneurs were seen as business rebels—brilliant and uncontrollable— who were shaking up the status quo. But they really were the first generation immersed in everything technological: video games, computers, CD-ROMs, computerized educational toys, and, of course, the Internet. As Boomers sat in shock, venture capitalists gave these kids billions. No one dared say that the emperor wasn’t wearing clothes, for fear that maybe, just maybe, the new kids on the block were right. The new economy was still undefined.

The media called them Generation X and Generation Y, and they listened to bands like Nirvana and Pearl Jam leading the grunge movement while comedians like Tom Green and shows like Jackass reflected a new generational cynicism.

As Generations X and Y emerged from college into their first jobs, they expected high-speed connectivity, cell phones, good starting salaries, and a laptop. They demanded all this and more at entry level. The assumption was that whatever the company wasn’t paying in salary, they could make up for by providing perks. If these new job seekers didn’t get these “toys,” they quit and ventured out on their own. The explosion of hundreds of new media start-ups in Manhattan from 1995 to 2000 was the direct result of this technologically immersed generation entering the workforce for the very first time—and flipping our world on its ear.

According to John C. Beck and Mitchell Wade, authors of Got Game: How the Gamer Generation Is Reshaping Business Forever, the entire dotcom boom of the mid-90s was due entirely to the first wave of a generation raised on video games, computer technology, and access to the Internet.

This is the Dungeons and Dragons crowd, more comfortable with interactivity and video game competitions than sitting around watching TV. The dot-com boom of the midnineties was the first wave. The Social Network Era called Internet 2.0 was the second wave. And the third wave
is upon us now.

Maybe this explains WHY everyone is obsessed
with getting the next phone, digital device
or gaming platform.

Thanks again for reading,




Brad Szollose
21st Century Change Agent: Generational expert, award-winning author, business consultant and keynote speaker

Brad Szollose is a much sought-after generational expert, management consultant and keynote speaker who helps smart companies understand just how much technology has transformed corporate culture and behavior…and how that impacts management interaction, expectations and sales in The Digital Age.



But this is not based on management theory: With a 30 year career as an entrepreneur he knows firsthand what it’s like to grow a company from a simple idea in a coffee shop to an internationally recognized brand.


Brad is a former C-Level Internet Executive who went from entrepreneur to IPO in 3 yrs—co-founding K2 Design, the very first Dot Com Agency to go public on NASDAQ. His company experienced 425% hyper-growth for 5 straight years, expanded from 2 business partners to 4 with 60+ employees and offices worldwide. At its height, K2 was valuated at over $26 million. 

His results only management model (ROWE) was applied to the first wave of young Generation Y workers producing great results—winning K2 the Arthur Andersen NY Enterprise Award for Best Practices in Fostering Innovation.

Brad Szollose is also the *award-winning author of Liquid Leadership: From Woodstock to Wikipedia which explores the subject of new leadership styles – mainly how to get the tech-savvy Generation Y and analogue driven Baby Boomers working together. ISBN-13: 978-1608320554

Known for his humorous and thought-provoking presentations, Szollose received the highest testimonial of his career from a C-Level audience member: "I just had my mind blown." Brad’s keynotes and workshops are highly interactive, heart-warming, humorous, and filled with high-content information that challenge assumptions and help leaders and managers create a better work environment for innovation to thrive.


Liquid Leadership has been called "THE guidebook for the 21st Century" and has won the 2011 Axiom Business Book Award silver medal for leadership, The Indie Business Book runner up silver medal as well as becoming a #1 Best-Selling Business Book on Amazon for Organizational Learning. Published in the United States by Greenleaf Book Group, in India by Prolibris and in South Korea by UI Books/Iljinsa Publishing.

Mr. Szollose also writes a monthly column on business and marketing techniques that reach Generation Y for A Captured Mind newsletter and is part of The Mind Capture Group faculty.

Today, Brad helps businesses close the Digital Divide by understanding it as a Cultural Divide – created by the new tech-savvy worker...and customer. 



* 2011 Axiom Business Book silver medal winner in the leadership

* #1 Amazon Best-Selling Author

"I just had my mind blown..." - A.S., Vistage, New York

Liquid Leadership by Brad Szollose is available at all major bookstores and for Kindle, Nook, iPad and Sony ereaders. Internationally published in India and S. Korea.