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february 20 - 22, 2025

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LATEST ANNOUNCEMENTS

Download the 2024

Book of Business

Legacy Awards Weekend featured over 1,500 Black Entrepreneurs, Corporate Professionals and Community Leaders. The

Keynote speaker Young Jeezy will be a part of L.E.G.A.C.Y!

Join us for an exclusive interview with the legendary rapper and astute entrepreneur, Jay "Jeezy" Jenkins on March 1, 2024. Beyond the microphone and the stage lights, Jeezy stands as a towering figure in the world of business and entrepreneurship. In this in-depth conversation, we'll peel back the layers of his iconic persona to reveal the strategic mind and relentless spirit that have powered his journey from the streets to the studio and into the boardroom.



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Join us for a 3 Day Celebration of Black Entrepreneurs

We invite you to L.E.G.A.C.Y. Awards Weekend 2024, a 3-day event, “Celebrating the Impact of Black Entrepreneurs.” The L.E.G.A.C.Y. Awards has become a meeting ground for aspiring and established entrepreneurs to network, collaborate and celebrate each other. This event is one of the top celebrations for Black Entrepreneurs in the City of Chicago, attracting over 1000 businesses annually, with an anticipated attendance of 1,500 entrepreneurs this year. The event features a Black Restaurant Showcase, Young Entrepreneur Contest, an Awards Gala and added this year a POWER Conference to support the growth of Black-Owned businesses.


POWER CONFERENCE

February 29th - March 1st

As a prelude to The L.E.G.A.C.Y. Awards Gala, The L.E.G.A.C.Y. Power Conference will take place on Thursday, February 29th (virtually) and Friday, March 1st in person at Greenwood Oasis (7621 S. Greenwood, Chicago,). The L.E.G.A.C.Y. Power Conference will provide informational support to Black Business Owners in the areas of Marketing, Operations, Financing, Corporate Contracts, Personal Development and more. Our goal is to provide inspiration, information and resources to help entrepreneurs scale and grow their business to 7 figures and beyond.

Over 30 Powerful speakers

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Over 30 Powerful speakers

Keeana Barber

Serita Love

Marseil Jackson

TeQuila Shabazz

Robiar Smith

Whitney Hampton

James Wheeler

Cassiopeia

Rosezena Pierce

View all speakers

L.E.G.A.C.Y Awards Gala

March 2nd

For the past 7 years the LEGACY Awards has become a meeting ground for successful entrepreneurs to network, exchange ideas and celebrate one another. The mission of L.E.G.A.C.Y. Weekend is to connect Black entrepreneurs of all sizes with each other and resources that can help them grow their business such as financial institutions and corporate contracts . It is also one of the largest stimulus for Black-owned businesses, having directly circulated over $1.5 million amongst Black owned businesses.

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  • What is the event outline?

    Thursday, February 29, 2024


    Virtual Conference

    9am to 2pm


    Legacy Talk

    6pm to 8pm

    Anyone with a ticket for Legacy Weekend and All Access



    Friday, March 1, 2024

    POWER Conference

    Hosted at Greenwood Oasis 7621 S. Greenwood


    8:15am Registration

    9:00am to 7:00pm Conference

    Featuring over 20 speakers on business growth, marketing, systems and more


    VIP Meet & Greet 

    7:00pm to 10:00pm 

    Private Location - only available with All Access VIP Pass 


    Saturday, March 2, 2024

    LEGACY Awards Gala

    Hosted in downtown Chicago


    6:00pm to 12:00am

    6:00pm to 8:00pm Reception/Restaurant Showcase

    8:00pm to 10:30pm Awards Gala

    10:30pm to 12:00am After Party 



  • What is the POWER Conference?

    The L.E.G.A.C.Y. Power Conference will provide informational support to Black Business Owners in the areas of Marketing, Operations, Financing, Corporate Procurement, Personal Development and more. We will have special panels for Young Entrepreneurs under 25 to help them on their pathway to success. Our goal is to provide inspiration, information and resources to help entrepreneurs scale and grow their business to 7 figures and beyond.



    Attendees will enjoy our Black Owned Business Vendor Showcase, powerful networking opportunities, Corporate Match-Making, complimentary breakfast and lunch, conference materials, power packed panel discussions, and workshop-style break out sessions.


  • What is the VIP Meet & Greet at the POWER Conference?

    This will be the event to jump start your weekend with a private VIP ONLY networking event. This will be the time for you to start your growing process whether you're thinking about starting a business and want to talk to other professionals in the same field, an entrepreneur who has just started your business or someone who’s been in business for years wondering how to scale upwards.


  • What is the L.E.G.A.C.Y. Gala?

    The L.E.G.A.C.Y. Awards has become a meeting ground for aspiring and established entrepreneurs to network, collaborate and celebrate each other. This event is one of the top celebrations for Black Entrepreneurs in the City of Chicago, attracting over 800 businesses annually, with an anticipated attendance of 1,000 entrepreneurs this year. The event features a Black Restaurant Showcase, Young Entrepreneur Contest, an Awards Gala.

  • Ad Deadlines

    1/4 Page AD - 2024 BOOK OF BUSINESS - $150.00 (4.25” wide by 5.5” height, Resolution 300dpi, File formats: .pdf or .jpg, Include a .25" bleed-around ad for safe text for artwork)


    Feature your business in the 2024 Book of Business with a Quarter Page Size Ad. Boost your brand’s awareness with a robust distribution of these books with 1,000 printed copies given to L.E.G.A.C.Y. Awards Events Attendees on site. Your digital ad copy will also be digitally distributed in our weekly newsletters, email advertising partners, social media and more, exposing your brand to 10,000 + new potential clients!


    1/2 Page AD - 2024 BOOK OF BUSINESS - $250.00 (8.5” wide by 5.5” height, Resolution 300dpi, File formats: .pdf or .jpg, Include a .25" bleed-around ad for safe text for artwork )


    Feature your business in the 2024 Book of Business with a Half Page Size Ad. Boost your brand’s awareness with a robust distribution of these books with 1,000 printed copies given to L.E.G.A.C.Y. Awards Events Attendees on site. Your digital ad copy will also be digitally distributed in our weekly newsletters, email advertising partners, social media and more, exposing your brand to 10,000 + new potential clients!


    FULL Page AD - 2024 BOOK OF BUSINESS - $500.00 (8.5” wide by 11” height, Resolution 300dpi, File formats: .pdf or .jpg, Include a .25" bleed-around ad for safe text for artwork )


    Feature your business in the 2024 Book of Business with a Full-Page Size Ad. Boost your brand’s awareness with a robust distribution of these books with 1,000 printed copies given to L.E.G.A.C.Y. Awards Events Attendees on site. Your digital ad copy will also be digitally distributed in our weekly newsletters, email advertising partners, social media and more, exposing your brand to 10,000 + new potential clients!


  • Ticket Types and Benefits:

    Power Conference General Admission (Early Bird) $150.00

    Ticket includes a continental breakfast and light lunch.  

    Event date and time: Friday, March 1, 2024,

    9:00 am to 6:00 pm

    Registration opens at 8:30 am


    Awards Gala General Admission (Early Bird) $100.00

    Ticket includes

    Event date and time: Saturday, March 2, 2024

    6:00 pm to 12:00 pm


    Awards Gala VIP Ticket (Early Bird) $150.00

    Ticket includes access to VIP Lounge, Special Food Vendors, 2 Drink Tickets, VIP Bar and Gift Bag

    Event date and time: Saturday, March 2, 2024

    6:00 pm to 12:00 am


    All Access VIP LEGACY Weekend Pass (Early Bird) $450.00

    Ticket includes invite-only VIP Night Thursday, February 29th

    VIP Ticket to Awards Gala

    VIP Conference ticket, premium seating and speaker meet and greet

    Premium gift bag

    Bonus: 2-month complimentary membership to LEGACY Network!


  • Special Placement

    L.E.G.A.C.Y. Awards Table Sponsor 3/2/24 $2500.00

    Receive 10 VIP Tickets, Sponsored Table seating with YOUR company’s name & Logo, and a Full Page Size Ad in our 2024 Book of Business. Boost your brand’s awareness with a robust distribution of these books with 600 printed copies given to L.E.G.A.C.Y. Awards Events Attendees on site.


    L.E.G.A.C.Y. Awards General Sponsorship $5,000.00

    Are you looking for brand visibility during LEGACY Awards Weekend?  Sign up for sponsorship and we can customize a package for you that includes ad placement, logo on signage and VIP tickets!  Contact legacy@wdbmarketing.com for more info!


    L.E.G.A.C.Y. Conference Small Business Vendor 3/2/24 + 1 Guest $500.00

    Includes vendor setup Friday March 1st for POWER Conference and 1 guest for conference.


    L.E.G.A.C.Y. Conference Small Business Vendor 3/1/24 With AD + 1 Guest $750.00

    Includes vendor setup Friday February 9th for POWER Conference, 1 guest for conference and 1/4 page ad in program book)


    L.E.G.A.C.Y. Power Conference Corporate Matchmaking Vendor 3/1/24 $2500.00


    L.E.G.A.C.Y. Power Conference Access to Capital Room Vendor 3/1/24 $2500.00



  • General Information

    Parking for Conference: Friday, March 1, 2024 - Parking is free in adjacent lots


Major Event Sponsors

WDB Young Entrepreneur of the Year

LEGACY is about giving back and making an impact.  One of the highlights of the weekend is our Young Entrepreneur of the Year contest that takes place during our awards gala on Saturday, March 2nd.  The contest will feature a pitch from 3 young entrepreneurs (25 or younger) in front of our awards gala audience.  The winner will win over $25,000 in prizes to help grow their business including cash, marketing support, legal advisory, PR campaign and more!  Entry is free so we are encouraging every young entrepreneur to apply or nominate someone today! 


Black Restaurant Food Showcase

One of the highlights of LEGACY is our Black Restaurant showcase.  During the awards gala reception indulge in over 15 Black owned restaurants and spirit lines including with all tickets!

Learn more
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Media Partners

  • The Black Mall

    The Black Mall

  • What U Need Is

    What U Need Is

  • Black People Eats

    Black People Eats

  • The Brunch Bunch

    The Brunch Bunch

  • The Early & Tia Show

    The Early & Tia Show

  • Olashay Marketing

    Olashay Marketing

  • AMPR Group

    AMPR Group

  • Black Chicago Eats

    Black Chicago Eats

  • Success Junkie

    Success Junkie

  • Eventnoire

    Eventnoire

  • Black Women Professional League

    Black Women Professional League

  • That's Why I'm Here

    That's Why I'm Here

  • The Times Weekly

    The Times Weekly

  • Youth Talkz

    Youth Talkz

Latest Press & Media Coverage

By Keeana Barber March 11, 2024
By Keeana Barber February 18, 2024
By Keeana Barber January 13, 2023
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