Jennyfer Crawford-Williams is a risk-taker.
Detroit’s Small Business Hype Woman, community advocate, and founder of Ask Jennyfer.
Jennyfer Crawford-Williams is the founder of Ask Jennyfer, a Detroit-based small business advocacy brand dedicated to creating opportunities for entrepreneurs through events, education, and community-driven platforms.
In 2014, Jennyfer stepped out on faith to pursue entrepreneurship full-time. With limited resources but a clear vision, she built a brand that now supports hundreds of small businesses, connects them to customers and corporate partners, and powers high-impact events like All Things Detroit—Michigan’s largest small business showcase.
Today, Jennyfer is recognized nationally for her work championing small businesses, building inclusive marketplaces, and creating spaces where entrepreneurs are seen, supported, and celebrated.
👉 Scroll to explore the ecosystem she’s built.
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The Foundation
Jennyfer Crawford-Williams is a Detroit-born entrepreneur who began her career in the construction industry after graduating from Detroit Public Schools. She worked on major projects across Michigan and Florida, building a strong foundation in project management, operations, and leadership.
After holding roles with Wharton-Smith Construction, Inland Waters Pollution Control, and Little Caesars, Jennyfer realized her passion extended beyond traditional corporate work. She wanted to create opportunities—not just manage projects.
In 2012, she founded Ask Jennyfer, initially hosting small events while working part-time in sales. By 2014, she stepped out on faith to pursue entrepreneurship full-time, driven by a mission to support small business owners through education, events, and community connection.
What started as intimate gatherings quickly grew into large-scale showcases, laying the groundwork for signature experiences like All Things Detroit Day and a growing ecosystem dedicated to small business success.
This Is Ask Jennyfer
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Today
Among other services at Ask Jennyfer, she conceptualizes, manages, and executes the nationally recognized small business showcase All Things Detroit, which draws up to 12,000 attendees and connects more than 200 small businesses each spring and fall.
In 2020, the event earned its own national holiday—National All Things Detroit Day. In recognition of its impact, Crawford-Williams was honored by Gov. Gretchen Whitmer in 2024 and received a U.S. Congressional Recordcommendation presented by Rep. Shri Thanedar.
Crawford-Williams expanded her work by launching All Things Marketplace, opening a brick-and-mortar location in Detroit’s historic Corktown district and providing retail, promotion, and shipping and fulfillment services for small businesses nationwide.
The marketplace earned Corp! Magazine’s 2022 Best of MichBusiness Award as a startup.
Signature Campaigns & Activations
Ask Jennyfer doesn’t just provide small businesses with advice and consultation, it puts its money where its mouth is in advocating for entrepreneurs everywhere through multiple events aimed at putting the spotlight on local businesses, artisans as well as professionals in different fields, and persuasions.
From in-house events to managed spectacles for partners and clients, Ask Jennyfer brings together patrons and a locality’s best kept secrets.
Ask Jennyfer creates high-impact campaigns that elevate small businesses, spotlight culture, and build community.
From large-scale All Things Detroit activations to curated icon and editorial campaigns, each project is designed to tell a story, increase visibility, and create meaningful connections online and in real life.
Below is a selection of signature campaigns that reflect our approach and impact.
When Crawford-Williams isn’t collaborating with organizations on major city events—such as curating small business pop-ups for the attendance-record-breaking 2024 NFL Draft in Detroit—she remains an active force in the city’s cultural and business ecosystem.
Her work includes annual events like Downtown Street Eats, The Night Market at Beacon Park, and Noel Night, along with serving as a board member for Detroit Month of Design 2024, the Downtown Detroit Partnership Advisory Board, and the Corktown Business Association.
In Spring 2024, Crawford-Williams was invited to guest host WDIV’s Live in the D alongside Tati Amare and has appeared as a recurring guest contributor for CBS Detroit. She is a past recipient of Crain’s Detroit Business 40 Under 40, the Detroit Young Professionals Vanguard Award, and the Presidential Lifetime Achievement Award presented by Dr. Missy Johnson of Fearless Women Rock.
In 2023, Ask Jennyfer also earned Corp! Magazine’s Best of MichBusiness Award. Through her Shop Small segment and ongoing media appearances, Crawford-Williams continues to spotlight emerging brands, founders, and community-driven businesses—bridging storytelling with real-world opportunity while amplifying small business visibility across Detroit and beyond.
Let's grow your business!
Ask Jennyfer developed and manages the successful small business showcase All Things Detroit. What began as a way toextend consulting services and highlight small business ownershas developed into a powerful event. Hundreds of small businessowners participate in this inspiring showcase that draws more than12,000 shoppers each time it is held in Spring and Fall. All ThingsDetroit is the biggest event to showcase small business owners inMichigan. In 2020, National All Things Detroit Day was created tocoincide with the Spring event. Learn more at www.iloveallthingsdetroit.com
All Things Marketplace began as a national buy-and-sell online platform for small business owners. Building upon the community that developed through successful events like All Things Detroit, All Things Marketplace offers a one-stop-shop where entrepreneurs connect with one another and find their customer base. In 2020, the marketplace opened its brick-and-mortar shop in Detroit’s historic Corktown district, which doubles as a community event space. All Things Marketplace also offers shippingand fulfillment services for small business owners. All Things Marketplace is earned the 2022 Best of MichBusiness Awards as a startup business. All Things Marketplace is located at Suite 123 at 1620 Michigan Ave. in Detroit. Learn more and Shop www.allthingsmarketplace.com
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All Things Ticketing, a small business-focused ticket hub, is a free resource for event organizers and attendees, Post an event to find your audience or buy tickets. The independent ticketing site supports the growth of small businesses. Learn more at https://allthingsticketing.com
Tune in to Ask Jennyfer: The Podcast to hear from small business experts, inspiring entrepreneurs and so much more. New episodes air on Wednesdays. The podcast is available via iTunes, Google Play and Stitcher. Subscribe and tune in.
Coming Soon
Ask Jennyfer developed and manages the successful small business showcase All Things Detroit. What began as a way toextend consulting services and highlight small business ownershas developed into a powerful event. Hundreds of small businessowners participate in this inspiring showcase that draws more than12,000 shoppers each time it is held in Spring and Fall. All ThingsDetroit is the biggest event to showcase small business owners inMichigan. In 2020, National All Things Detroit Day was created tocoincide with the Spring event. Learn more at www.iloveallthingsdetroit.com
All Things Marketplace began as a national buy-and-sell online platform for small business owners. Building upon the community that developed through successful events like All Things Detroit, All Things Marketplace offers a one-stop-shop where entrepreneurs connect with one another and find their customer base. In 2020, the marketplace opened its brick-and-mortar shop in Detroit’s historic Corktown district, which doubles as a community event space. All Things Marketplace also offers shippingand fulfillment services for small business owners. All Things Marketplace is earned the 2022 Best of MichBusiness Awards as a startup business. All Things Marketplace is located at Suite 123 at 1620 Michigan Ave. in Detroit. Learn more and Shop www.allthingsmarketplace.com
All Things Ticketing, a small business-focused ticket hub, is a free resource for event organizers and attendees, Post an event to find your audience or buy tickets. The independent ticketing site supports the growth of small businesses. Learn more at https://allthingsticketing.com
Tune in to Ask Jennyfer: The Podcast to hear from small business experts, inspiring entrepreneurs and so much more. New episodes air on Wednesdays. The podcast is available via iTunes, Google Play and Stitcher. Subscribe and tune in.
Coming Soon
Ask Jennyfer partners with small business owners, founders, and creatives to turn ideas into real opportunities. Through strategy, events, campaigns, and community-driven experiences, we help brands increase visibility, connect with customers, and grow with intention.
- Strategic event & activation planning
- Brand visibility & storytelling
- Community-driven growth opportunities