Why The Female Founder Of A Personal Styling Service Says Early-Stage Founders Should Get Comfortable With Being Uncomfortable

#PEAlum, #PEIntensive17, Advice, fashion startup, female founders, Monday Motivation, underrepresented founders

Mondays can be rough—sometimes we need a little motivation to get the week started. Our #MondayMotivation blog series brings you tips and life hacks from Project Entrepreneur Alumnae—female founders who applied to the Project Entrepreneur Venture Competition to attend our two-day PE Intensive and join a nationwide community of hundreds of women entrepreneurs. Get to know more about the PE Community and #beinspired by how these women motivate themselves each Monday to tackle the week ahead.


Personal styling services are having a moment. The industry itself is extremely competitive, but efforts to democratize personal styling have taken off in recent years, both with consumers and investors. Companies like MM.LaFleur, Trunk Club and Stich Fix have raised millions in venture capital, and Katrina Lake, Founder and CEO of Stitch Fix (a subscription service that sends hand-selected clothing items directly to consumers) was the only woman to lead an IPO in 2017 and is the youngest woman to lead a company to IPO…ever.

Carving out her own niche in this exploding market is Jeannine Adams, Founder and CEO of Ready Pretty, a company that sends its customers a curated collection of links to purchase pre-styled outfits from online shopping destinations around the world. Jeannine attended the PE Intensive in 2017, and we had a chance to chat with her recently about how she’s been building Ready Pretty since attending the Intensive, the “aha moment” that led her to pivot her business model, and why she values the really uncomfortable moments.

Photo courtesy Jeannine Adams, CEO of Ready Pretty

What inspired you to start your business?

I wanted to do something that fulfilled me—that allowed me to better play to my strengths in business and fashion. I worked in PR and marketing for nearly 12 years before starting Ready Pretty, but I had always had my foot in the door of the fashion world here in Chicago and beyond. Most importantly, I knew that my [end] goal was not to be an SVP at some big ad agency. I knew that I wanted to do more. [I had] a bit of an “it’s now or never” moment, and I decided the time [to launch Ready Pretty] was now.

What’s been the biggest challenge you’ve faced so far?

For me it’s really been zeroing in on my customers and ensuring that the brand speaks to them personally, like the company was made just for them. I’ve gone back and forth [between business models and target customers] a few times, but now with my most recent decision to slightly pivot the business, my ideal customer has sort of revealed itself on its own. I think when something like that happens, you know you’re on to something good.

What’s been the greatest reward?

By far it’s been the experience that I’ve had since starting the business. From the people I’ve met and helped, to the collaborations, the big media hits, events I’ve attended or opportunities that have arisen. I’m in awe every single time I get to experience something new, step out of my comfort zone and ultimately grow as an entrepreneur. As cliche as it sounds, getting comfortable with being uncomfortable is really where the magic happens, and that’s something I continue to work on every single day.

What changes would you most like to see in your industry, and how are you working to make those changes happen?

By far what I’m seeing is that there are so many amazing small and independent boutiques across the U.S. that carry amazing labels and brands, but sadly, they are oftentimes losing out to big box stores with more resources, stronger online footprints and more money to spend. We’ve just recently decided to pivot Ready Pretty’s business slightly, by offering a solution for these boutiques to better compete for the attention of the savvy shopper.  I’m excited to be serving this new customer, while offering our current customers a more unique shopping experience. Ideally, I want to see more consumers shopping small—not only is it great for local economies, but that’s where a lot of the really good stuff is.

Who or what motivates you to keep going, even when things get tough?

I’ve always believed that fashion can be transformative. I’ve watched women gain confidence simply through what they wear. I’ve always felt a need to empower women and help them feel their very best, and I do feel as though clothing (while some may see it as superficial) can do just that.

Can you provide a few updates on what’s new with your business or what you’ve accomplished since you attended the PE Intensive in April 2017?

Since attending the PE Intensive, I’ve certainly seen accelerated customer growth, updated my branding, refocused my efforts around my customer and most recently started to pivot my model and approach in order to address the needs of the small boutique owner. I’m beyond excited to officially launch this aspect of Ready Pretty’s business this summer.

What’s one piece of advice you’d give to other entrepreneurs just starting out?

As I mentioned earlier, my advice would be to get uncomfortable. When I really push myself out of my comfort zone—be it putting myself out there, learning a new skill, taking a chance on something—good things always come of it. It may not be an instant success, but at the very least, I learn and get smarter. And to me, those lessons are invaluable.


For more motivation from our PE Alumnae, check out our interview with Melissa Stefaniak. Melissa is Founder of Single Baked Sweets, a company that ships single-serve, take-and-bake desserts that come with everything someone needs to make, bake, and decorate a delicious treat for one. Melissa attended the PE Intensive in 2016, and we had a chance to catch up with her and talk about the biggest challenges she’s faced while working to modernize an almost ninety-year-old industry, her accomplishments since she attended the PE Intensive, and why she thinks it’s never too soon to start talking about your business.