All Things Detroit (Make Me Smile). This Sunday at Eastern Market

Talking Small Business with Jennyfer Crawford of All Things Detroit & Phillip Simpson of The Smile Brand

All Things Detroit

Small business may be the future of Detroit, but it’s also its past. That’s what we learned in conversation with Detroit born natives and entrepreneurs, Jennyfer Crawford and Phillip Simpson.  

Crawford is the owner of Ask Jennyfer and founder of All Things Detroit. 

Simpson an owner of the Baltimore Gallery and founder of The Smile Brand. 

What they share is a passion for the city and people that shaped them: a vision of small business as a means of empowering individuals and communities. In conversation both are quick to celebrate their peers as well as their predecessors. While the term “pop-up” might be trending now, Detroiters have been popping-up with business concepts in homes and shared spaces long before big marketing teams branded a comeback.  

Crawford’s career began in her living room when the pamper party concept morphed into a way to support makers in the city. It could be argued that Simpson’s career started as an adolescent in Saturday art classes, where he discovered art as a social transformation. His first business was painting murals in his neighborhood. 

You can find them both this Sunday in Eastern Market at All Things Detroit, the small business showcase Crawford founded five years ago. This weekend’s year’s event will feature over 250 small businesses, including Simpson’s The Smile Brand, and the friend’s first joint project, a limited-edition t-shirt. 

We sat down with Crawford and Simpson to learn more about their businesses. Final takeaway: A lot of people are talking about Detroit, but some have more to say than others.  

CV Henriette: Tell us about you

Jennyfer Crawford: Ask Jennyfer is a Detroit-based firm specializing in branding and promoting small businesses. We curate and coordinate small business vendors for events. Our signature event is All Things Detroit, a local vendor showcase, which returns to Eastern Market this Sunday, March 31, 2019.

Phillip SimpsonMy business is The Smile Brand. As Lead Smile Pusher, my goal is to spread joy and optimism with my brand and art. I’ll be a featured vendor at All Things Detroit in Eastern Market on March 31 and will have all new items for sale – including hats, caps, hoodies and t-shirts. 

CVh: Why Detroit? 

JC: I started my business in Detroit because it is my hometown, and I wanted to be part of the growth in Detroit. 

PS: Why not Detroit? 

CVh: Why small business? 

JC: I wanted to help people like me who have a passion for doing what they love. 

PS: We start small with dreams of being large. We start small with our first buyers being friends and family. We start small with hope that one day our time will come. 

CVh: What’s in a name? 

JC: My business is called Ask Jennyfer. It was inspired by the way other professionals would recommend that business owners consult me for their branding needs. 

PS: The correct business name is everything. My mission is to spread joy and encourage the world to smile. The Smile brand was the best name for me. A brand dedicated to the life of smiling. 

CVh: What’s your inspiration? People? Places? Other businesses? 

JC: My inspiration comes from the business owners I work with and the everyday people who risk it all for what they believe in to get up everyday to make it happen. 

PS: My inspiration is and has always been the love of people and how if I can encourage one person to smile… I can encourage millions. 

CVh: Biggest challenge of running a small business in Detroit? 

JC: The biggest challenge for me has been getting others to understand my vision to help other small business owners succeed. I have created multiple platforms to help others grow their businesses here in the city. 

PS: If you asked me this a decade ago, my reply would have been resources and lack of funds. But now I know first-hand Detroit has a ton of great small business incubators. Now I believe one of the most challenging things is to follow through and stay focused. 

CVh: Greatest reward? 

JC: My greatest reward is when I see others succeed. 

PS: Freedom. 

CVh: What’s exciting? 

PS: The journey. 

 CVh: Space for a shoutout 

PS: A huge shout out to every small business owner reading this. A shout out to every artist working on their craft. I know it’s hard at times, but we can do it. All the late nights will pay off. 

CVh: Advice to aspiring entrepreneurs? 

JC: Speak what you want into existence but be prepared for the journey. 

PS: Dream. Plan. Execute. Fail and start over. 

CVh: Advice to Detroit’s city planners? 

JC: My advice for Detroit city planners is to not forget about the neighborhoods and all the history that exists here in Detroit. 

PS: Buy Local. 

CVh: What’s next? 

JC: What’s next for me is focusing on building profitable markets for small businesses nationwide. My new app, Meet Me at the Markets, will be launching soon to highlight all of the events curated by my company, Ask Jennyfer. 

PS: Smile Takeover. 


All Things Detroit Takes place this Sunday, March 31st, in Shed 3 of Eastern Market. Tickets are $5-$15 in advance and may be purchased here.

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