The Diamond Challenge Summit is a unique week-long experience providing semifinalists from around the world the opportunity to develop new skills while energizing their entrepreneurial spirit. High school entrepreneurs learn from world-class speakers, entrepreneurs, and mentors, and forge lifelong connections! Members of the community are invited to attend the culminating awards ceremony.

Our 2021 Keynote Speakers

Alex Osterwalder

Ann Makosinski

Past Diamond Challenge Speakers

*Orange indicates Keynote Speaker

Sam Beard

Jefferson Awards Foundation

Alexa Curtis

Life in the Fashion Lane

Lisa Ford

Capital One

Susan Frech

Social Media Link

Dan Freeman

Horn Entrepreneurship

Julie Frieswyk

Horn Entrepreneurship

Trevor Geise

Megan Grassell

Yellowberry Company

Katlyn Grasso


Emma Johnson

Em John Jewelry

Elizabeth Kennedy

The Jefferson Awards Foundation

Ben Mathew


Nat Measley

The Fun Department

Tony Middlebrooks

Horn Entrepreneurship

Sylvester Mobley

Coded by Kids

Mac Nagaswami


Shelby Newsome

Tote Magazine

Margaret O'Dwyer

Delaware Youth Leadership Network

Lori Palmer

Trellist Marketing and Technology

Jill Pante

University of Delaware

Zach Phillips

The Kitchen

Ben Rapkin

Horn Entrepreneurship

Rich Roat

House Industries

Ryan Swartz

Capital One

Jessi Taylor

Barrel of Makers

Andrea Tinianow

Global Delaware

Lindsay Yeager

Dare Women’s Foundation

Haile Thomas

HAPPY Organization

Justin Lafazan

The Next Gen Summit

Zack Jones

Horn Entrepreneurship

Sally Marie Young


Rich Sedmak

Schoolyard Ventures

John Himics

First Ascent Design

Pauline Himics

First Ascent Design

Alexis Mattei

University of Delaware

Mike Mackenzie

University of Delaware

Amira Idris

Vibrating Therapeutic Apparel

Jonathan Maxim

K&J Growth Hackers