Trill or Not Trill is an educational platform made to integrate culturally relevant content within the world of student development and leadership.

Trill or Not Trill brings together voices from pop culture and education to student affairs. Trill or Not Trill is a consulting firm, a speaker’s bureau, a media platform, a alternative classroom, a blog, and more.

Our Founders

MrJeffDess is an author of five books with a Masters Degree in English Literature. Lenny is professor within the business departments at 4 different institutions, with an MBA.  Both men have traveled nationwide and abroad as public speakers, educators, and co-founders of their educational platform, Trill or Not Trill, which bridges the gap between pop culture and student development.

With over 15 years of student affairs experience between, Lenny and Jeff have dedicated their lives to changing lives and disrupting the popular narrative of success.  Between the two of them, they have appeared on CBS, Fox 5 New York, The Boston Globe, Ebony Magazine, Black Enterprise, The Root, and Hot 97.

From working with the NFL to NASPA to NCSL, these two have continually pushed the envelope when it comes to presenting and impacting all those they meet.

Now we must say, Lenny is a Bulls Fan, and Jeff continues to painfully root for the Knicks; but for some reason, they are still great friends and colleagues. If they can get through that and remain cool with one another, then anything is surely possible.

Trill Guiding Principles

  • We lead with integrity.
  • We provide outstanding, unconventional student development and leadership programming and professional development workshops.
  • We speak to “the leader” in everyone, especially students, treating them as adults with respect and dignity.
  • We aim to establish mutually-beneficial partnerships with institutions of learning, both domestic and abroad.
  • We promote cultural relevance, innovation and engagement in all aspects of the student’s academic career.

We Value:

  • Positive disruption of standard leadership and development and educational norms
  • Integration of culturally-relevant content within the world of student leadership and development
  • Professional development of educators in student affairs positions
  • Diversity of thought and the inclusion of all leaders regardless of level, race, nationality, religion, sexuality, disability, age, illness, or gender identity


Alvert Hernandez
Alvert Hernandez

Student Specialist

Alvert has a Masters in Higher Education Administration & Leadership from Montclair State University. He is a proud Cuban and Dominican American and loves arroz con habichuelas y pollo guisado.

Ash Cash
Ash Cash

Financial Educator

Antonio Talamo
Antonio Talamo

Senior Strategist

Antonio is the Coordinator for Commuter Students and Programs at Montclair State University. He is a huge sports fan who loves the New York Giants and the Boston Red Sox and swears he is the reason the Red Sox broke the Bambino curse.