Rachel Schostak

Ever since she can remember, Rachel Schostak has been into fashion. As the family story goes, Rachel started her career in fashion as a toddler. “I was always fascinated with clothes, picking out my own outfits – sometimes five a day! As a young girl, I was forever reading fashion magazines, constantly playing with my personal style, changing looks,  layering pieces, even cutting my own hair.”

Rachel grew up in Farmington Hills, Michigan. Focused on the arts, she attended the University of Michigan in her freshman year.  “At heart, I knew that I wanted to be in New York studying fashion, but was open to giving the University of Michigan a try.” At age 19, she applied to the Fashion Institute of Technology (FIT), made the transfer and moved to New York. “Living in New York on my own was a challenge. I had to work to support myself, took out student loans. Looking back, to be in that fast-paced industry, getting the education and life experience has been invaluable.”

Rachel has worked in fashion retail for companies large and small; one of her first experiences in the industry was an internship at Cosmopolitan Magazine. She has worked for menswear/womenswear and childrenswear companies and in marketing, always with an eye to opening her own business. Today, Rachel is the creator and proprietor of a unique retail space online called Styleshack. Capitalizing on Detroit pride and the city’s growing “shop local” movement, Styleshack is an e-commerce platform that aggregates more than 150 independent boutiques, specialty stores and designers and connects them with subscribers according to their individual style preferences.

Rachel Shostak
Confident, creative, innovative, persistent, resilient.

With the support of Bizdom, the startup incubator founded by Quicken Loans’ Dan Gilbert, Rachel finds herself in fashionable company these days. Working in the Bizdom offices at 1528 Woodward, she is located strategically in the heart of the city’s growing retail action, two doors down from the the glitzy new John Varvatos store, which she helped to open in April.

You have to be quick to follow Rachel’s success. With little more than a year in business under her belt, Rachel has been featured in Fortune Magazine and on speaker panels for TechWeek in Detroit and Chicago. She is particularly proud to be mentioned recently among the FIT Alum of Note.

On a Monday morning, Rachel meets up with myJewishDetroit . . . wearing jeans with a flair,  a tailored “Theory” vest layered over a lacy white tee and a long turquoise hamsa necklace – fashions found at Guys N Gals, one of her Styleshack.com stores.

myJewishDetroit: Rachel, in five words, what is your definition of an entrepreneur?

Rachel: Confident. Creative. Innovative. Persistent. Resilient.

On family background

myJewishDetroit:  Did your family own a business? How did you develop your work ethic and business style?

My parents always have been supportive of my career decisions. Both are hard-working and I suppose you could say they instilled in me a strong work ethic.

My dad, Jay Prinstein, and his father, Allen Prinstein, had a fruit and produce business [Prinstein Brothers] in the Eastern Market for many years. My dad would wake up at 3 am to go to work and, according to my mom, I’d be wide awake in the crib at that hour, peeking out, ready to get up with him. My mom has had a long and passionate career (over 30 years) as a school social worker.

I’ve always been inspired by my older brother, Justin, who has an interesting career in pro baseball. Currently, he’s an International and Pro Scout for the Baltimore Orioles. Previously, he played pro baseball all over the world, including Israel where he played in the inaugural season of the Israeli Baseball League.

myJewishDetroit: How did you meet your husband Jeff?

Interesting story. We met at Camp Tanuga in Kalkaska, Michigan, in the summer of 1999. Jeff was one of my first crushes. We kept in touch as friends, and our paths would cross every so often. He was living in Chicago and I was in New York. And then, finally, one Thanksgiving 2009 when we were both home in Detroit, Jeff asked me out on a date.  After that, we just knew. It’s a little bit of a fairy tale when you meet the man you love when you’re 12, but that’s what happened.

We were married in 2012 – at Camp Tanuga.

On moving back to Detroit

Until I met Jeff, I had no plans to move back to Detroit. While we were still dating, I left New York and moved to Chicago. But shortly after, he got this offer from his family business [Schostak Brothers & Company, Inc], so I had to figure out what my next step was. Fortunately, I got a great job offer with Denise Ilitch Designs. So we came back to Detroit together in 2010.

myJewishDetroit: Biggest surprises moving back to the D?

Being away for a few years helped me grow as an individual and I’m grateful for the time I spent in New York and Chicago. Coming back here as an adult, I was surprised to find how strongly I felt about Detroit and how great it was to be back and engaged in this community, specifically the Jewish community.

Rachel Schostak
“Fashion trends are ever changing and every day we find something new that our consumers want and need.”

On Styleshack

myJewishDetroit: What inspired you to start Styleshack?

The initial concept of Styleshack was born during a summer trip in 2012,  I love traveling, “shopping local” in different boutiques and discovering interesting communities. I thought that it would be great to have a place online to find all of these wonderful stores. At the time, there was no website providing that kind of service, so I started Styleshack as a project.

When I saw that I was on to something, I talked to Denise Ilitch, my boss at the time. I was working with her as a social media specialist and helping her with her own website. Denise gave me her blessing and told me to go for it and pursue my own dream. So I took a chance, left my job at Denise Ilitch Designs and applied to Bizdom.

mJD: Tell us about your start-up with Bizdom.

In my mind, I had this great business plan and was confident that I was going to get into Bizdom. Just like that. To my surprise, I was turned down!  I was disappointed . . . but not discouraged. In fact, being turned away at first was a good thing, because I spent the following six months putting the pieces together to build the company. When I went back to Bizdom the second time, I knew I had a viable business plan. I also had the preliminary workings of my product up and running in an interactive site with my Blog, a Style Quiz to profile subscribers and a user sign-up, all a part of the bigger vision. I believe this demonstrated to Bizdom that I had the persistence and the know-how to find the proper resources to get started on my own.

mJD: From concept to launch, how long did it take?

To keep a company running in a start-up space, you have to move fast. I started the concept in August 2012 with a fashion style blog, then added the style quiz to show investors that I had a following of consumers. Then I went to the retailers to say I have consumers that they may not be reaching. I launched the official product – the complete website with its store membership – in December 2013.

In terms of drawing out the technology road map for the site – that is something we are changing and tweaking constantly. Because fashion trends are always changing and every day we find things that our consumers want and need.

Styleshack offers a unique experience for fashion shoppers and browsers alike. When you sign up, you take a 10-question quiz with visuals that suggest your own style preferences in categories like dresses, jackets, shoes, colors, even cell phone covers. Then you are matched with a style “card” on file, indicating your fashion type, from Sporty to Boho, from Glam to Classic. We then send you fashion trends and products from local stores, based on your personal preferences.

We started with 14 retailers and now work with over 150 boutiques, designers and e-tailers around the country. Our customer base – the number of subscribers who shop online –  has grown from 7,000 to more than 15,000.

mJD: What’s next for Styleshack?

Adding new categories of retailers . . . menswear, kids’ clothing . . . more gifts.  Also, we’re always looking for new talent to grow the Styleshack team.  In this regard, Federation’s NEXTGen Connect has been instrumental in finding awesome summer interns for us.  We’re now booked for the summer, but will start looking again in the fall.

On Detroit / Community Involvement

mJD: How do you see your role continue to play out in the resurgence of the city?  

I find that there’s something very special going on here, and as I travel to retailers around the country, I’m proud to say that I’m from Detroit, working in Detroit and part of the movement of entrepreneurs and startups making it happen here.

mJD: What do you tell people considering moving back to Detroit or into the city for the first time?

Do it! But do your research. Know what you’re looking for, come up with a plan and make it happen. Detroit has great resources – like Bizdom, Tech Town, Hebrew Free Loan. I should know, because   I’ve talked to them all. The community here – particularly the Jewish community – is very collaborative and generous.

mJD: Who have been your mentors?

There have been so many, but specifically I would name Denise Ilitch (entrepreneur), David Farbman (CEO, HealthRise Solutions), Jennifer Gilbert (formerly Doodle Home, now Amber Engine) and the folks at Bizdom. The entrepreneurial energy among the Bizdom cohort of companies is contagious. Sharing space with other founders gives us the opportunity to get feedback, share our struggles and celebrate our wins. Together. Having access to the Bizdom leadership and the greater community of other founders has been instrumental for my company’s growth and success.

On shopping local

mJD: Imagine you were planning to take visitors on a “Shop in the D-Tour for a Day,” where would you go?

Fun time! We’d need a bus and a full day for sure. Here’s what I’d suggest:

We would start in Birmingham for a delicious breakfast at Commonwealth; from there we would head directly downtown to the “central business district,” where some notable stops include:

-John Varvatos store (a fashionable rock ‘n’ roll experience)

-Roasting Plant (coffee break) right in Campus Martius

-Riverwalk access (a few blocks away)

-7 Greens (a favorite place for lunch)

-Citizen Yoga

-Lbrary Street Collective (art gallery)

Z LOT (very famous parking lot with commissioned graffiti art)

Other must-sees: in Corktown, an awesome vintage store called, El Dorado General Store; in Midtown, Shinola and Willys Detroit; and a Styleshack favorite: Love. Travels. Imports.

Rachel Schostak


Fashion style: Edgy Chic, Boho, always Classic. (I pick up a little of everything.)

Fashion brands: I like to take basics, like a tee from Target or Gap, and layer that with a tailored blazer or vest. It’s not about the most expensive look. It’s mixing and matching basics with statement accessory, one great piece, like a Rachel Zoe or Zadig et Voltaire.

Restaurants: Seldom Standard downtown or Bucharest Grill inside the Park Bar for a quick lunch; Elie’s Mediterranean Grill and Luxe Bar and Grille, both in Birmingham

Places to meet for coffee: Commonwealth in Birmingham and Roasting Plant in Campus Martius

Building in the skyline: Guardian Building

Places to take visitors or kids: Detroit Zoo, DIA offers variety – Campus Martius with the food trucks in the summer

Favorite vacation: Paris

Sport: Tennis. Ping pong. (I talk a good game.)

Jewish Food: Everything Israeli. Israeli salad and falafel, could eat that every night. Babka—

Jewish Expression: Zei gezunt. (Yiddish, meaning be healthy.) My grandpapa, who is going to be 90, signs off every phone conversation with that expression.

Guilty pleasure: US Weekly and Sour Patch Kids (any sour candy)

Never leave home without: Cell phone, laptop, wallet, hand sanitizer, Chapstick

Reading Now

Essentialism: The Disciplined Pursuit of Less, by Greg McKeown

Crazy is a Compliment: The Power of Zigging When Everyone Else Zags, by Linda Rottenberg