Real Talk with Jeannine Adams, Founder of Ready Pretty

Ever looked in your closet to realize you had nothing to wear? Well Jeannine Adams’ business, Ready Pretty, can help you out. Jeannine built the specialized online styling and shopping service to help other women find confidence in their clothes, all while working another full-time job and being a mother. Here she shares all she’s learned from her journey as a small business owner and entrepreneur, from acknowledging her limits to knowing when it’s time to take a risk.

Name: Jeannine Benoit Adams
Location: Chicago
Title: Founder
Company: Ready Pretty
What it is: The easy and affordable online styling and shopping solution for busy women.

What inspired you to start Ready Pretty?

I believe that clothing can be transformative. For years, I helped close friends and family with outfit recommendations — and saw first-hand how a great outfit made people feel. Seeing someone gain confidence right before my eyes was hugely gratifying. I wanted to recreate that feeling over and over again, so I sat down and put a plan together in an effort to help women everywhere.

How did you come up with the name Ready Pretty?

I’m incredibly visual so I just started to write different words out on paper and then draw connections between words. I knew I wanted to convey a sense of beauty, but also a sense of efficiency. We take the guesswork, time, and stress out of getting dressed. When I looked down at my paper, two words jumped out at me: “pretty” and “ready.” I liked them both, switched them up, and Ready Pretty was born. I absolutely love our name and the meaning behind it.

What does a typical day look like for you?

It’s truly different every day. I check in with our stylists each morning to get a sense of what they’re working on, if there are any issues, etc. Then the day is full of meetings — whether that’s with our intern, other cool startups in Chicago, vendors, etc. We’re always creating content for our site and social media so there’s bound to be a photo shoot (big or small) in the day as well. I spend a lot of time on business and marketing strategy to ensure we’re positioning ourselves for growth. And lately, we’re excited to have been selected for Rent The Runway’s Project Entrepreneur — which is a small business intensive — in which we may have the opportunity to pitch our business to investors. I’ve been perfecting that pitch in order to be ready for those important few days.

Would you do anything differently?

I would have started sooner. This is what I was meant to do. It’s fulfilling and challenging and a little bit scary. I’ve never been more in and out of my comfort zone at the same time. Looking back, I wish I would have made the decision to go for it earlier. But I guess this is just all a part of my journey.

How did you manage to work a full-time job, take care of your son, and launch Ready Pretty all at once?

HA! Those days were pretty crazy. Crazy in the sense that I was unable to focus really well on one thing. Family time is most important to me; my son, my husband, and my dog will always be number one my priority. Working full-time as a Director of Content for a local advertising agency and launching Ready Pretty made for a lot of long days. My focus was truly on my 9 to 5 from 9 to 5. Then it was home to hang with my family and then once Ethan went to bed it was Ready Pretty time. It was exhausting and exciting and so worth it. I didn’t leave until I felt fully ready to take the leap. My days are still just as long but it’s nice to finally be able to focus on just one job.

What’s been the hardest part of starting your own business?

You want to do everything but at times can be limited due to resources — be that time, money, team, etc. It’s one thing to have a cool idea; it’s another to actually execute. I’m learning to really focus my efforts to drive the business results that matter.

What has been the most rewarding part of starting your own business?

It’s the personal connections that we have with our users. We always get the best stories from women who feel more stylish and ultimately more confident in their clothing. Whether it’s the woman who felt empowered heading into an interview for her dream job (she got it!), or the woman who was headed to a wedding where she knew she’d see her ex, or the stay-at-home mom who wants to get out of her yoga pants and get her stylish self back — it’s by far the best part of this business and the reason I started it in the first place.

Did you have to learn any new skills when you started Ready Pretty? What were they?

Yes! I built my own website using Squarespace and learned a bit of coding along the way. Using platforms like Canva and PicMonkey, I do a lot of the design work on the site and blog — I’ve always loved to create, but graphic designing is certainly not a skill of mine. In the last few months, I’m feeling more confident with my skills on that front.

How did you know that it was time to leave your job in advertising? How did you overcome the fear of the unknown?

This was a tough one for me. I didn’t hate my job by any means, and the security of a consistent paycheck was tough to walk away from! But for me, it came down to a now or never situation. I had something in front of me that I truly believed in, that helped people and made me feel good, and it felt like now was the time. I didn’t want to look up in five years and say “I wish I would have.” I wanted to be able to tell my son that I took a risk for our family, believed in myself, and decided to create the life I wanted. That’s the advice that I would give to him, so I had to be the example. It was a calculated risk — I saved for several months to be able to have a bit of a cushion — and my incredible husband (who is also a successful small business owner) supported my decision 110%.

How did your previous career in advertising help you with Ready Pretty?

For years I worked helping to promote other brands (big and small) — so that really helped me when it was time to market Ready Pretty. Being strategic in the way we approach our marketing efforts has helped us with our overall brand awareness and client acquisition. We’ve still got a lot of work to do — but for right now it’s not something that I feel I need to outsource.

How do you deal with roadblocks and failures?

Things are not always going to work out. I like to consider these things speedbumps. I used to work for someone who used to always say, “Everything is fixable.” I firmly believe that. It’s about learning from those speed bumps, thinking through a new plan, and executing. I genuinely feel like I’m learning something new every single day and that is shaping how I approach the growth of this business.

Do you have a specific strategy for social media? Which platforms do you use and how much do you rely on it for growing your business?

Yes, we do — we’re constantly evolving this strategy. I’m in the process of reevaluating our current efforts to find efficiencies and opportunities to expand our presence. We’re on Instagram, which is by far our best performing platform, as well as Facebook, Twitter, and Pinterest. We utilize these platforms in various ways to help support, inspire, and educate our audiences.

What do you like to do when you’re not working?

Time with my family (whether that’s exploring Chicago together — it’s a whole different city with a kid! — or traveling to new places), and dinners with my husband and our friends. I do a monthly supper club with an incredible group of female friends that’s the perfect mix of good wine, good food, and good times. At this stage in my life, experiences with the people I love are truly what’s most important to me — and the memories that come along with them.

How do you balance your work with your personal life?

Just like every other busy mama out there. I do the very best that I can, try not to be too hard on myself, and remind myself often that I’m a good mom, wife, friend, and business owner. A quote that has always stuck with me is, “You can do anything, but not everything.” I make time for the things that matter, and luckily I don’t need a lot of sleep!

How do you define success?

I’d say it’s living the life you truly want and deserve, versus living the life we settle for. Creating something greater than yourself — something that not only helps to provide for my family, but also helps people feel better about themselves. One day, I want people to remember Ready Pretty as the brand that helped women feel like their very best selves.  That would be success to me.

What’s next for you and Ready Pretty?

For now, it’s continued growth. We are looking to bring on new stylists, launch a new service offering, and continue to grow our user base. We just want to help as many women as possible feel good in the clothing they wear every single day.