
Congratulations Destiny Watson!
2022 Winner
WDB Cares, NFP congratulates our new 2022 Young Entrepreneur of the Year, Destiny Watson, Founder of You Matter 2, an organization that strives to dynamically empower emerging youth leaders to create a generation of change. You Matter 2 consists of 7th-12th grade students from the south suburban area is a group dedicated to changing the world and giving back to their communities.
Our 2022 Young Entrepreneur of The Year Winner will receive up to $20K in cash and prizes to help their vision grow, donated by experienced Black Entrepreneurs, interested in supporting the next generation of Black Entrepreneurs.
Over $10,000 in Prizes for the Top Winner!
- Roundtrip to Africa for the US Africa Youth Entrepreneur Summit in Accra, Ghana September 2020
- $1,000 Cash
- $2,500 Marketing and Printing services from WDB Marketing
- FREE Headshots for Top 3 finalist | Amber Marie Green Photography
- FREE membership for the top 3 finalist to The Golden Baton Group
- Interview on the AC Green Show on 106.3Fm and 1390AM
- FREE event coordination from ATwinToo Productions
- New Feature in SCENE Chicago or Chicago NOW from The Media Doctorz
- $500 advertising package from The Black Mall
- 1 Month FREE PR services from AMPR
- $500 digital marketing package from Red Level Entertainment
- Interview on www.VoiceoftheChi.com
- Free promotional video from Global 360 Marketing

Ava Dorsey - 2020 Winner
We have our YOUNGEST finalist ever! Ava Dorsey founder of Ava’s Pet Palace, an organic pets treat company that prioritizes the health of pets. Her products are featured in premium stores like Bentleys and she is currently working on getting her products into a manufacturing house. Oh and she’s 12!
2020 Runner Ups

Caleb Dunson
At the age of 17 out next Young Entrepreneur finalist Caleb Dunson is one of the YOUNGEST executive directors in the country! He founded the Youth Entrepreneurship League while still in high school. His vision is to create an incubator for mentorship, funding resources and capacity building to ensure that his generations of entrepreneurs have a fighting chance to succeed. Our future looks bright!

Jeremy Frierson
Our last young entrepreneur finalist Jeremy Frierson turned his hobby into a full branding firm, The Frierson Agency! His work has been featured on the Stellar Awards and his client roster includes gospel artist Todd Dulaney, Pastor John Hannah, Melvin Rodriguez and Grammy award winning artist Keirra Sheard!
Thank You To Our Sponsors












Past Winners
2020 | 4th year winner
Ava Dorsey
Ava's Pet Palace
2019 | 3rd year winner
Aaliyah Stewart
ASW Foundation
Aaliyah Stewart wowed the audience with not only her story of resilience but the power of her vision to stop the violence in our communities with a movement she started at the young age of 14, the I Am Them Movement.
2018 | 2nd year winner
Shamari Walker
Ascunia Tech
2016 | 1st year winner
Cecil Wilson
Founder of Goffers Inc.
Common Questions
The top 3 finalist will be notified the week of February 7th.
Day of each finalist has a chance to pitch their business concept to an audience of 500+ entrepreneurs. The audience has a chance to vote via text on their winner of choice. The winner is announced at the end of the legacy awards.
$20,000
Value in Prizes
$7,500
Marketing Support
9
Young Leaders Helped
3
Years
This event is presented by


