Jason Ryan Dorsey

Jason Ryan Dorsey

Leader in Bridging the Generations

Jason Ryan Dorsey teaches leaders how to make each generation in their workplace and marketplace a competitive advantage. He helps clients and audiences bridge generational disconnects, increase innovation across generations, and drive sales based on cross-generational best practices. Recognized as The Gen Y Guy®, Dorsey is an acclaimed keynote speaker, bestselling author, and award-winning entrepreneur. Fortune 500 clients repeatedly hire Dorsey because his message is engaging, actionable, and bottom-line focused.


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Jason Ryan Dorsey is a thought leader on Gen Y and bridging the generations.

Dorsey teaches leaders how to make each generation in their workplace and marketplace a competitive advantage. He helps clients and audiences bridge generational disconnects, increase innovation across generations, and drive sales based on cross-generational best practices. With four generations in the workplace, and five or more in the marketplace, Dorsey’s message delivers results.

Recognized as The Gen Y Guy®, Dorsey is an acclaimed keynote speaker, bestselling author, and award-winning entrepreneur. His trademark speaking style—which doesn’t include PowerPoint—has taken him to all 50 states and as far away as Egypt, Finland, Spain, and India. Fortune 500 clients repeatedly hire Dorsey because his message is engaging, actionable, and bottom-line focused. The numbers speak for themselves: 2,000 speeches in 14 years—and standing ovations from audiences as large as 13,000.

Dorsey is the author of four popular books: Y-Size Your Business, My Reality Check Bounced!, Graduate to Your Perfect Job in 6 Easy Steps, and 50 Ways to Improve Schools for Under $50.  

A proud member of Gen Y (who texts his mom every day), Dorsey has been featured as a generational expert on 60 Minutes, 20/20, The Today Show, The View, and in Fortune Magazine, The Wall Street Journal and over 100 other media outlets. Dorsey draws on his unique perspective as a member of Gen Y who has spoken with 400,000 of his peers on issues ranging from workplace beliefs and education preferences to online shopping habits.

  • 1. Crossing the Generational Divide: Unlocking the Power of Generations for Your Strategic Advantage

    For the first time in world history, four distinctly different generations are working side by side. Each of these four generations (Matures, Baby Boomers, Generation X, and Generation Y) is guided by a different set of values, beliefs, and expectations. In Crossing the Generational Divide, bestselling author Jason Ryan Dorsey entertainingly reveals each generation’s preferences and priorities to highlight what they bring to the workforce—and how to build on their common ground.

    Jason then shares his frontline-tested process which participants can immediately rely on to lead a culture of cross-generation communication, innovation, engagement, teamwork, and performance. Filled with surprising statistics, step-by-step strategies, and laugh-out-loud stories, participants leave this presentation prepared to make their multigenerational workplace a competitive advantage.

    Crossing the Generational Divide Presentation Outcomes:

        * Recognize and understand the divergent values, preferences, and priorities of all four generations in the workforce.
        * Learn a step-by-step process for leading all four generations while respecting employees as individuals.
        * Impact your organization with actions and strategies that other leaders have successfully relied on to bridge the generations in their workplace.

    Customization and Reinforcement: Jason’s presentation includes a confidential workplace data review, customized multi-page handout, and specific strategies designed for immediate implementation in your organization.

  • 2. Y-Size Your Business: How Gen Y Employees Can Save You Money and Grow Your Business

    Generation Y is the fastest growing demographic in the United States workforce. Along with a new definition of “business casual,” Gen Y adheres to a different set of workplace beliefs and priorities than other generations already employed.

    We also bring tremendous potential and big expectations (just ask, we’ll tell you). Gen Y’s attitude toward work can make us a growing challenge or a strategic opportunity depending entirely on how business leaders respond.

    In Y-Size Your Business, Jason cuts through the stereotypes to teach participants Gen Y’s workplace mindset. He then reveals a step-by-step process and specific actions that employers can immediately adopt to unlock the talent, loyalty, creativity, and performance of this emerging workforce.
    As a member of Gen Y, Jason is uniquely qualified to discuss his generation’s workplace mindset. He balances an insider’s view of Gen Y (he texts his mom every day) with the workplace realities facing executives and managers in an increasingly competitive global market. He also tailors his presentation to focus on the aspects of the Gen Y employment life cycle most important to your organization:

        * Attracting and Hiring Gen Y
        * Onboarding and Engaging Gen Y
        * Motivating and Leading Gen Y
        * Developing and Professionalizing Gen Y
        * Retaining Gen Y

    Y-Size Your Business Presentation Outcomes:

        * Learn Generation Y’s workplace beliefs, preferences, and priorities—all from the perspective of an insider. (Jason even explains why Gen Y doesn't use vowels in text messages.)
        * Engage Gen Y employees from our first day at work. This is critical because Gen Y decides on our first day if we will stay with an employer long term.
        * Impact your organization with creative, ready-to-use actions that attract, motivate, and retain Gen Y employees while saving you money.

    Customization and Reinforcement: Jason’s presentation includes a confidential workplace data review, customized multi-page handout, and specific strategies designed for immediate implementation in your organization.

  • I've read countless articles and attended many presentations regarding Generation Y. Jason's presentation was by far the most comprehensive and had the most impact on not only my understanding this group, but also bridging the gap between all generations. His delivery is both professional and entertaining with the ability to reach everyone in the room no matter the diversity of the group - Business, University, etc. The most beneficial aspect of Jason's message is the ability to take it back to our business and make an immediate impact on what we do every day. Thank you Jason for your energy and compassion for helping us bring  'ALL GENERATIONS' together.

    H-E-B
  • Jason's presentation and the information he provided were exactly what our state's business leaders needed and wanted to hear. At a time when North Dakota is struggling with many workforce issues, Jason provided positive and practical ideas for attracting and retaining Gen Y talent. His ability to keep the audience engaged while providing pertinent, timely information is a winning combination.

    North Dakota Chamber of Commerce
  • Your presentation, coupled with your handout, helped me gain a much greater understanding of the "Y" generation. You masterfully had the audience slip into the shoes (sneakers or sandals if you prefer) of Gen 'Y' and take a glimpse of life from their perspective, which is their reality. Wonderfully good job and thanks for the experience. It was a great way to end the day.

    Shell Exploration and Production Company
  • Jason did a phenomenal job in his presentation of not only breaking down the different generations, but more importantly, giving us actual ideas of how we can implement this information in our day-to-day operations to increase retention of all of our employees. His interactive presentation was extremely well received by our management team. It was very beneficial for our managers to hear what it is that motivates Generation Y and what they can personally do to connect with these employees -  I would highly recommend Jason Dorsey as a 'Generational' expert speaker.

    Enterprise Rent-A-Car
  • Jason spoke at the TESS 40th Anniversary Exposition in Norway and made a lasting impression on our firm. Jason's energetic way of speaking and his message about Gen Y struck home. We gained invaluable insight into how the generations work which has given us a good foundation to carry on with our efforts in bringing the generations closer together. Jason is a true expert in his field and we give him our strongest recommendations.

    TESS Academy, Norway
  • Jason connects with his audience from the opening minute. He is so entertaining and informative - our group did not want his presentation to end. His insight on the importance of an employee's first day at work is truly powerful. What a difference we could make if we followed his tips in just this one area!

    Taco John's International
  • Again, you were very, very well received by our MHCA members who represent many of the largest behavioral health companies and organizations in the US.

    Mental Health Corporation of America
  • Jason Dorsey's presentation was informative, engaging and relevant. Our team left motivated to better connect with their 'Gen Y' employees. I personally learned a lot and am proof that he can teach an old Boomer new tricks!

    Taco Bell Corp
  • Y-Size Your Business: How Gen Y Employees Can Save You Money and Grow Your Business
    November 2009

    Y-Size Your Business: How Gen Y Employees Can Save You Money and Grow Your Business

    In Y-Size Your Business, Jason Ryan Dorsey, The Gen Y Guy, presents a step-by-step methodology for best employing Gen Y without investing a lot of time or money. A member of Gen Y himself he delivers an insider's view of his generation as well as more than fifty cost-effective, ready-to-use strategies that deliver immediate measurable results. Dorsey collected these creative strategies from the frontlines of business during his work with executives, managers, and entrepreneurs in businesses large and small around the world.  He shows you exactly how to attract the best Gen Y employees, quickly develop their workplace skills, and then unlock their performance, motivation, and loyalty.


  • My Reality Check Bounced!
    January 2007

    My Reality Check Bounced! The Twentysomething's Guide to Cashing in on Your Real-World Dreams

    It’s time to cash your reality check and re-create your life on your own terms. In your twenties you expect to finally live life on your own terms. But it can seem like the world won’t cooperate. Jason Ryan Dorsey helps you turn this coming-of-age crisis into opportunity. He shows you the big secret of the real world—that you don’t realize how much control you have over your life until you use it.


  • Graduate to Your Perfect Job in 6 Easy Steps
    May 1997

    Graduate to Your Perfect Job in 6 Easy Steps

    Jason Dorsey presents a comprehensive and reader-friendly guide for obtaining the career of your dreams. With youthful insight and practical examples, Dorsey reveals a concise pathway for determining, understanding and achieving career goals-valuable lessons designed to produce immediate results for a lifetime.