2020 Young Entrepreneur

Of The Year Award Contest

The Countdown Starts Now

February 29, 2020

Here are the 2020 finalists!

Apply today to be the next young entrepreneur of the year !

Qualifications: Applicants must be 25 years age or younger and have an active business to apply.

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!


Apply to be the next LEGACY Awards next Young Entrepreneur of the Year!


Nominate a young entrepreneur for Young Entrepreneur of the Year!

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

Thank You To Our Sponsors


Past Winners

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

At the young age of 17, Shamari Walker pitched to the legacy crowd his newly developed app and technology company, Ascunia Tech. While still in high school had not only successfully developed apps and websites, he had a growing list of clientele awaiting his services.

2016 | 1st year winner

Cecil Wilson

Founder of Goffers Inc.​

As CEO of Goffers, Inc. Cecil Wilson wowed the crowd with the concept of his company Goffers, Inc., an on-demand delivery service with a foundation in community. His savvy and unique approach to his business model made Cecil the undeniable winner of the first young entrepreneur of the year award.

Common Questions

No, there is no cost to submit an application.
If you nominate someone we will reach out to invite them to apply. They MUST complete their own application to be considered.
To apply the business owner must be 25 or younger. There is NO age minimum for this contest.
If you are selected as a top 3 finalist, someone from the LEGACY committee will call to reach out to regarding next steps. As support for your pitch, you be able to to practice with a professional business coach as well a past young entrepreneur award winner finalist within The Golden Baton Group.
The WDB LEGACY Awards is an awards gala that celebrates the impact of Black entrepreneurs. In it’s 4th year, the event hosts over 500 entrepreneurs, executives and community leaders for a night of networking and celebration. The event is produced by WDB Marketing, the sponsor the young entrepreneur contest. It will be hosted on Saturday, February 29, 2020 from 6pm to 10pm at Malcolm X College. Tickets to the event can be purchased at Eventbrite. You DO NOT have to purchase tickets to apply to the contest. If you are selected as a finalist you are encouraged to invite your network to purchase tickets in support of you.
Yes you will be notified by email if you did not move through to the final round. You will receive notification the week of February 7th.

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. 

The application is judged based on your business model and concept, ability to scale and how well you have been able to make an impact within your business.


Value in Prizes


Marketing Support


Young Leaders Helped



This event is presented by