Jason Dorsey
Jason Ryan Dorsey is a bestselling author, acclaimed speaker, and award-winning entrepreneur. Often referred to as the "Gen Y Guy," Jason has been featured as a Generation Y expert on 60 Minutes, 20/20, NBC's Today Show, ABC's The View, NPR's On Point, and in The Wall Street Journal and Fortune Magazine. Jason's high-energy keynotes and content-rich trainings have impacted over 1,800 ...
Topics:
- Author/Writer /
- Business Motivation /
- Corporate Culture /
- Demographics /
- Education

Jason Ryan Dorsey is a bestselling author, acclaimed speaker, and award-winning entrepreneur. Often referred to as the "Gen Y Guy," Jason has been featured as a Generation Y expert on 60 Minutes, 20/20, NBC's Today Show, ABC's The View, NPR's On Point, and in The Wall Street Journal and Fortune Magazine. Jason's high-energy keynotes and content-rich trainings have impacted over 1,800 diverse audiences across the United States and as far away as Egypt, Finland, Spain, and India.
During a typical year, Jason headlines events ranging from executive retreats and education summits to exclusive management conferences. Over 250,000 copies of his books are used in schools, colleges, and corporations. In recognition of his business achievements, Jason won the Austin Under 40 Entrepreneur of the Year Award at age 25--one of the youngest winners ever.
Jason's nontraditional path began at age 16. Growing up in a rural community, Jason saw few opportunities and abundant obstacles. At a critical moment, a teacher inspired Jason to leave high school and start college early.
Going to college early and out-of-state changed Jason's perspective about what was possible. He spent a summer studying medicine in Florida, another summer working on an archeological dig in Israel, and then a year attending college full-time in upstate New York. It was during his studies in New York that Jason discovered he had a talent for helping young adults who were struggling academically and from tough backgrounds.
By age 18, Jason was a junior in college with an extensive network, respected mentors, and tremendous job opportunities. He also saw that many of his peers were not well positioned to secure the job they wanted. Determined to help, Jason authored and then self-published Graduate to Your Perfect Job in his college dorm room.
Jason celebrated his 19th birthday $50,000 in debt and sleeping on the beige carpet of a tiny garage apartment. He had never felt more alive or vulnerable.
Word of Jason's book and message eventually reached the media. Soon business and education leaders were asking him to keynote their high-profile conferences. Graduate to Your Perfect Job--which included a diagram of how to tie a tie--went on to become a national bestseller. It is estimated that 100,000 members of Generation Y have used Jason's first book as a resource to enter the workforce.
Jason initially focused his speaking efforts on reaching educators, administrators, Gen Y students and other school stakeholders. He wanted to continue the legacy of the educator who changed his life. This led to Jason speaking on-site at over 700 schools and colleges. Along the way, Jason collected cost-effective strategies that school leaders had found successful for strengthening their school from the inside out. He shares the best of these in his acclaimed school culture improvement book, 50 Ways to Improve Schools for Under $50.
Jason's focus on generational dynamics in the workplace began when he was contacted by business leaders frustrated with the loyalty and performance of their Generation Y employees. These business leaders wanted an insider's perspective on exactly how to attract, retain, motivate, and develop this emerging workforce--especially with a skilled worker shortage fast approaching.
Jason was well aware of the difficulty business leaders were having with their Generation Y employees, because this was an underlying theme in his 2007 book, My Reality Check Bounced!, which was published by Random House. Jason realized that his experience speaking directly to 350,000 Gen Y'ers about workforce issues--and being a member of Generation Y himself--gave him a unique perspective on how to engage Generation Y employees. He also knew that a key component to unlocking Generation Y's workplace potential was to focus on bridging all four generations now working side by side.
To understand the realities of leading a multigenerational workforce, Jason interviewed executives, managers, entrepreneurs, and employees representing each generation in a variety of industries. His goal was to learn their beliefs, priorities, and preferences to find common ground in the workplace. Jason used this experience and extensive research to develop a framework and step-by-step strategies business leaders can use to increase employee loyalty, teamwork, communication, and discretionary effort across all four generations.
Now 29, Jason has delivered over 1,800 keynotes and trainings to diverse audiences as large as 13,000. He is currently writing a new book that explains how to unlock Generation Y's workplace potential and connect all four generations in the workplace.
Please note that Jason customizes his keynotes and trainings to fit your audience, industry, and specified outcomes.
Gen Y @ Work: An Insider's Guide to Retaining and Motivating
Generation Y Employees
1-hour keynote or up to 2.5 hour training
Over 75,000,000 members of Generation Y--born 1977 to 1995--are entering the
workforce. They adhere to a different set of workplace beliefs and priorities
than the three generations currently employed. Generation Y's attitude toward
work can make them a challenge to attract, retain, motivate, and develop. In
Gen Y @ Work, bestselling author Jason Ryan Dorsey cuts through the stereotypes
to teach managers and executives exactly what Generation Y covets at work--and
why. He then reveals a step-by-step process and specific actions that employers
can immediately adopt to unlock the talent, loyalty, and teamwork of this
emerging workforce.
As a member of Generation Y, Jason Ryan Dorsey is uniquely qualified to discuss
his generation's workplace mindset. Jason's live seminars and bestselling books
are estimated to have helped 100,000 of his peers enter the workforce. Jason
combines his unique Generation Y insight with the expertise that comes from
being an award-winning entrepreneur. The result is Gen Y @ Work, a powerful
program that is entertaining and results driven.
Attendees leave Gen Y @ Work able to:
- Understand Generation Y's workplace beliefs, preferences, and priorities.
- Connect with Generation Y employees from their very first day at work.
- Retain and motivate Generation Y employees without increasing their pay.
Crossing the Generational Divide: Making the Four Generations in
Your Workplace a Competitive Advantage
1-hour keynote or up to 2.5 hour training
For the first time in modern US 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, acclaimed speaker and bestselling author Jason Ryan Dorsey sheds light on each generation's thinking styles to highlight what they bring to the workforce--and what they want in return.
Jason then shares a frontline-tested approach that participants can rely on to reinforce a culture of cross-generation communication, trust, and discretionary performance. Filled with entertaining stories, surprising statistics, and ready-to-use ideas, participants leave Crossing the Generational Divide prepared to make their multi-generational workplace a competitive advantage.
Attendees leave Crossing the Generational Divide able to:
- Recognize and understand the divergent values and priorities of the four generations in the workforce.
- Influence their organization's culture to embrace each generation while respecting employees as individuals.
- Lead employees to greater loyalty by facilitating an emotional bond between employees and their company's success.
How An Educator Saved My Life!
1-hour keynote or up to 2.5 hour in-service
In this inspiring program, Jason shares his personal story of educators
taking the risk to reach out to him--and changing his life forever. He then
reveals specific, front-line tested strategies and actions that every
school stakeholder can use to have a more lasting, meaningful impact on their
students. All attendees--from first-year teachers to seasoned
administrators--leave this high-energy, emotional keynote feeling good about
themselves, their profession, and inspired about the difference they make.
Ideal for: Education conference opening or closing general sessions,
school-year faculty kick-offs, and mid-year professional development programs.
Better Schools on a Budget: 50 Ways to Improve Schools for Under $50
1-hour keynote or up to 2.5 hour in-service
Administrators and educators at all levels want fun, creative,
cost-effective ideas that other school stakeholders have used to strengthen
their school from the inside out. In this interactive program, Jason shares
powerful stories of schools transformed by the actions of individual school
stakeholders who took the risk and responsibility to try something new in their
classroom, hallway, department, building, or district. Every attendee leaves
this program with a more hands-on understanding of school culture and ten to
twenty (depending on time) specific, ready-to-use ideas they can immediately
implement.
Ideal for: Education conferences focused on systemic school improvement,
in-services related to relevance, rigor, and relationships, and summer
professional development academies.
Inspiring Hard-to-Reach Students
1-hour keynote or up to 2.5 hour in-service
After working on-site at some of the country's most challenging schools, Jason has developed a unique strategy for connecting with and motivating hard-to-reach students. This strategy enables him to quickly build the trust, respect, and confidence of these students who often do not look, dress, or talk like him. In this practical program, Jason shares his strategy so your attendees can better engage and influence their hardest to reach students. This program is ideal for school stakeholders who want their students to take more responsibility for their actions, set and achieve higher academic and graduation goals, and make better decisions.
Ideal for: Conferences and summits for school leaders serving hard-to-reach student populations, in-services and professional development programs focused on best practices for serving hard-to-reach students, and grant funded initiatives designed to increase the performance of hard-to-reach students.

