Trill or Not Trill is a full-service agency at the intersection of leadership, learning, and culture. We deliver strategic development, dynamic training, and immersive engagement for education and corporate sectors. We’re not your typical consultancy. We blend:
Whether it’s a student, a team, or an organization we help people grow.
Trill or Not Trill is a full-service agency at the intersection of leadership, learning, and culture. We deliver strategic development, dynamic training, and immersive engagement for education and corporate sectors. We’re not your typical consultancy. We blend:
Worked with 500,000+ students and professionals across the country and abroad.
Partnered with 175+ colleges and universities including Yale, UCLA, Princeton, and Rutgers, Colorado State, Iowa State, Rutgers, NYU, University of Kentucky and more.
Delivered trainings and activations for 50+ leading brands such as Google, the NFL, Twitter, and Macy’s.
CBS,Earn Your Leisure Fox 5 New York, TEDx, Hot 97, The Boston Globe, Ebony, and Black Enterprise
like NCSL, NSLS, and Google HRA Academy, Travis Scott(Cactus Lab), Macy’s, Phi Sigma Beta, and more
Jeff Dess is an award-winning educator, best-selling author, and sought-after public speaker with over 15 years of experience in Learning and Development, student engagement, and culturally responsive education. His career has been dedicated to transforming the landscape of higher education by integrating innovative leadership development strategies, equity-driven programming, and culturally relevant pedagogy.
Jeff is the Co-Founder of Trill or Not Trill, a disruptive educational firm and leadership institute dedicated to revolutionizing student learning through culturally responsive programming. Through this platform, he has designed and led transformative leadership training programs tailored for college students, faculty, and administrators. His expertise lies in bridging the gap between traditional higher education models and modern, student-centered approaches that reflect the diverse cultural experiences of today’s learners.
Jeff’s impact extends across over 100,000 learners, having led keynote addresses, workshops, and training sessions at top institutions such as Syracuse University, NYU, UCLA, University of Michigan, and Florida International University. He has also collaborated with corporate and industry leaders—including Goldman Sachs, Twitter, and Madison Square Garden—to develop professional development programs that enhance student career readiness and leadership competencies. His thought leadership has influenced national higher education organizations such as NASPA, ACUI, and NSLS
A prolific author, Jeff has written seven books, including the Amazon best-seller We Wear Kicks to Work, co-authored with Trill or Not Trill Co-Founder Lenny A. Williams. His writing explores themes of leadership, identity, and the intersection of culture and education, serving as a resource for both educators and students navigating the complexities of modern academia.
Jeff’s insights and thought leadership have been featured in Ebony Magazine, Complex, AfroTech, The Root, and other national publications, further solidifying his influence in the field of education. His passion for student success, faculty development, and institutional innovation continues to drive his work as he remains committed to reshaping higher education to be more inclusive, dynamic, and culturally responsive for the next generation of learners and leaders.
TEDx Speaker | Business Professor | Leadership Strategist | Co-Founder, Trill or Not Trill
Lenny A. Williams, MBA, is a globally recognized leadership strategist, business professor, and keynote speaker known for delivering high-impact presentations that blend pop culture, strategy, and innovation. As co-founder of the award-winning learning and development agency Trill or Not Trill, Lenny has reached over 500,000 students and professionals through dynamic leadership training, executive coaching, and immersive educational experiences.
With more than a decade of experience teaching business at colleges across the U.S. and abroad, Lenny has built workforce and leadership development programs for organizations like Google, Mastercard, Twitter, Nike, the NFL, JP Morgan Chase, Buzzfeed, and Macy’s, and collaborated with top-tier institutions including Yale, NYU, UCLA, and Columbia.
A two-time TEDx speaker and best-selling author of We Wear Kicks to Work, Lenny is widely respected for his ability to connect across generations and industries. He served as the lead AI education consultant on Mastercard’s first small business chatbot and helped design the first virtual learning platform at the Georgia Aquarium—pushing the boundaries of how leadership, education, and technology converge.
Drawing from his background as a former college athlete and his MBA in marketing, Lenny also works closely with student-athletes and institutions on NIL strategy, brand development, and long-term identity building. His expertise helps athletes and young professionals navigate visibility, monetization, and legacy in the digital era—with a focus on building brands that are both profitable and purpose-driven.
He’s delivered over 250 keynotes and trainings at conferences, companies, and colleges—on topics ranging from authentic leadership and personal branding to organizational transformation and next-gen talent development. Lenny is currently pursuing his Doctorate in Transformational Leadership, further deepening his ability to help organizations lead through change.
His work has been featured on CBS, Fox 5 New York, Earn Your Leisure, The Boston Globe, Ebony Magazine, Hot 97, and more. He has also advised institutions on retention, branding, and student success strategy—including the development of a nationally recognized leadership program for Men of Color.
Whether addressing CEOs, creatives, educators, or athletes, Lenny brings a rare mix of substance, energy, and cultural intelligence—leaving audiences not just inspired, but ready to lead.
He served as the lead AI education consultant on Mastercard’s first small business chatbot and helped design the first virtual learning platform at the Georgia Aquarium—pushing the boundaries of how leadership, education, and technology converge.
Drawing from his background as a former college athlete and his MBA in marketing, Lenny also works closely with student-athletes and institutions on NIL strategy, brand development, and long-term identity building. His expertise helps athletes and young professionals navigate visibility, monetization, and legacy in the digital era—with a focus on building brands that are both profitable and purpose-driven.
He’s delivered over 250 keynotes and trainings at conferences, companies, and colleges—on topics ranging from authentic leadership and personal branding to organizational transformation and next-gen talent development. Lenny is currently pursuing his Doctorate in Transformational Leadership, further deepening his ability to help organizations lead through change.
His work has been featured on CBS, Fox 5 New York, Earn Your Leisure, The Boston Globe, Ebony Magazine, Hot 97, and more. He has also advised institutions on retention, branding, and student success strategy—including the development of a nationally recognized leadership program for Men of Color.
Whether addressing CEOs, creatives, educators, or athletes, Lenny brings a rare mix of substance, energy, and cultural intelligence—leaving audiences not just inspired, but ready to lead.
We have a team with 80+ years of combined experience in education, industry leadership, branding, and curriculum development, delivering impactful, culturally responsive training.
Empowering visionary leaders to drive impact through purpose-driven culture, strategic clarity, and bold innovation that transforms teams and organizations.