Community//

Kelley Legler: “Nobody will be more passionate about my business venture than me”

Writing about yourself as an entrepreneur is harder than it seems. I have moved to several different writing locations throughout my home to answer these interview questions. It’s an uncomfortable feeling to take time to write, thinking you are inspiring others with your experience and wisdom but also therapeutic putting into words about how far […]


Writing about yourself as an entrepreneur is harder than it seems. I have moved to several different writing locations throughout my home to answer these interview questions. It’s an uncomfortable feeling to take time to write, thinking you are inspiring others with your experience and wisdom but also therapeutic putting into words about how far you have come.


As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Kelley Legler. Kelley is the Owner of Baby Jack & Company a children’s educational toy brand with unique fabrics created by her kids’ drawings. She is a mom of two, to Jack (10) and daughter Bailey (8) from Milwaukee, Wisconsin who spreads kindness with her business. For the past 10 years she has been competing with top baby brands in the industry and bringing awareness to causes important to her customers.


Thank you so much for doing this with us Kelley! Can you tell us a bit about your “childhood backstory”?

I grew up with two hard working parents in the suburbs of Milwaukee and was the youngest of two kids. I always talked loudly over my brother and get my ideas heard. I was the sidekick to my mom’s side hustle: Mary Kay, crafty inventions, DIY jewelry, face painting and more. I learned at a young age to put myself out there and be loud about it. I learned later in life that failure, faith, kindness and having a knack for thinking outside of the box will make more opportunities.

What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?

It all started with my son Jack who loved anything ribbons and tags. He migrated towards the care label on every toy and chewed on his bib and pieces of clothing. I yearned for a way to utilize my marketing talents and creativity after becoming a new mom and being let go from my 9–5. I struggled with severe postpartum depression and anxiety and sewing literally saved my sanity. My mom taught me how to use a sewing machine and I began creating these tag blankets for friends / family as baby gifts. These tag blankets served as a sensory comfort object for kids and soothed Jack’s separation anxiety as he tried to fall asleep. One day, he was twirling his finger in the ribbon and got his finger intertwined. Upon hearing that scary sound of my baby in distress, I vowed to ensure that our ribbon tags are always sewn closed for added safety but still providing that tactile engagement. Since that moment, we became the only tag blanket /toy brand that keeps ribbons sewn shut to ensure little fingers are safe.

There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?

I built a brand around raising two little kids and growing as a mother. This business became a third child in need of nurturing, investment and my time developing into a family business. Having the support from my husband and mother-in-law helped me to balance this new life and experience all the ups and downs as a team. I feel that if people take the time to really consider all aspects about running a business, as if it is another child, their expectations will evolve in a similar way. You must be open to transitions, changes and temporary defeat. I have had many challenges both as a parent and as a business owner and dealt with failures, milestones and accomplishments in the same way — you live, you learn, and you grow.

What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?

I believe that if there is something you yearn for in life, you owe it to yourself to at least try to obtain it. Over the years in business, I have connected with many levels of entrepreneurs and each spoke about having no regrets. They turned that negative into a lesson learned and continue to grow from it. As an entrepreneur, being reluctant is part of the journey, but we are all hard wired to push on and try.

It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?

I get giddy with new technology and change. This entire business grew right along with Facebook and social media. I even created my first website out of basic HTML. I keep it fresh and enjoyable by learning new ways to engage with my audience, seeing the effect that our product has on a parent’s child and hearing stories about my customers. Every image of a child I see with my product validates what I do!

Our products were originally intended for babies and infants but as my own two children grew, so did our brand. At a young age my kids started to help me with promotion, product development and textile design. Their crayon drawings turned into fabrics. We created the Learning Lovey Collection that is a “look & find” concept of teaching kids with our prints. My kids took basic shapes, letters and numbers and hid them within the pictures to encourage development. Incorporating my own children as part of our everyday model makes it so enjoyable because they can experience the accomplishments and get inspiration for their future selves.

What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?

Running a small business is no easy task. It’s a roller coaster of emotions that consumes daily life. Some days I feel alone in the decision making and the hardest part is not knowing when to ask for help, who to delegate to and what I should focus my energy on. The moment I hired my team, we expanded, and they continue to bring a quality of work like no other.

Can you share what was the most striking difference between your actual job and how you thought the job would be?

Being in the sales industry is extremely difficult. It exposes my vulnerabilities; personality and I am learning to develop a thick skin to endure all the feedback. Most entrepreneurs will never get passed the “no”. It is viewed as a closed door and they stay stuck in the negative. I have been faced with countless declines which only fuels my drive to succeed, but it wasn’t like this from the start. I thought my job would be easy, people would love a children’s product created by kids and the money would roll in. The reality is that every single day it takes hard work, creativity and patience for slow growth.

Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?

This feeling is normal and occurs since I am passionate about what I do. I have invested personal money and time into growing and molding my brand and have considered the alternative and ease of getting a “real” job. I personally seek guidance in my family, my mentor and team to overcome these moments. Usually they occur within a new transition or opportunity of growth deriving from another failed business venture. I always keep in mind that, “this too, shall pass”.

Can you share the most interesting story that happened to you since you began leading your company?

I believe that everything I do in life is a stepping stone to where I am are supposed to be. My husband’s family once owned farmland in Madison, Wisconsin and it was sold to American Family Insurance to build their corporate headquarters. Ironically, my first craft fair with my mother-in-law was held at American Family Headquarters. Being from Wisconsin, one of our top selling designs is the Farm Friends Learning Lovey that Jack designed with me. Since we are an American family living the American dream, I pitched the idea of selling these products as a marketing premium to American Family — a security blanket that has roots with American Family, a gift for those purchasing financial security for their loved ones. It is a wonderful tie into Jack’s ancestors who once owned that farmland and grew a small business, to hopefully partnering with a larger business that supports the American dream.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

In the beginning, I was doing all our cut and sew for our blankets. My mother-in-law was helping me keep up with demand and we were trying to grow too fast for our two person craft. She was even snipping the little thread off the sewn shut ribbons which wasted so much of her time! We offered a variety of sizes, fabrics and attempted at designing new products (failing miserably), even offering embroidery; which resulted in many misspelled baby names. For a small, growing company, we learned fast that quality over quantity is better. We streamlined our product offerings and fabric designs outsourcing to a team of local seamstresses to take over our production. It was the best decision we ever made for proper growth vs getting burnt out with the number of tasks needing completion.

Who has inspired or continues to inspire you to be a great leader? Why?
My mentor Karmen continues to inspire me as a mother, woman and business owner. Having years of experience in the textile design industry, she introduced me to my outstanding factory allowing for better profit margins, lower margins of production error and quality goods. She brings a new level of love, light and faith to my professional self and challenges me to have perseverance and a positive mind set.

Karmen came into my life out of kindness. I gifted a product to someone seeking a baby shower gift through an industry contact. Upon receiving my product, we connected and since has guided me into growing my brand and business. I try to continue throwing kindness out like confetti knowing I am deserving of its rewards.

How have you used your success to make the world a better place?
To me, having a business should mean that you are making a difference in someone’s life. Designing a product that brings comfort, education and safety to children brings me so much joy. I am constantly inspired by the customers that receive our lovey tag blankets and am always looking for more ways to reach families. Since connecting with a friend who manages a prayer page on Facebook about her son with a congenital heart defect, together we have brought comfort to over 3,000 kids in hospitals. We designed a fabric for our blankets to raise awareness for CHD so that recipients and families have a person to guide them and show support. This has grown into other organizations working with Baby Jack & Co. to design cause awareness fabrics to bring support to children with pediatric cancer, down syndrome, autism and comfort families in law enforcement, military and firefighters.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Writing about yourself as an entrepreneur is harder than it seems. I have moved to several different writing locations throughout my home to answer these interview questions. It’s an uncomfortable feeling to take time to write, thinking you are inspiring others with your experience and wisdom but also therapeutic putting into words about how far you have come.
  2. I learned that there are going to be so many people that are against seeing your successes so you need to align yourself with those that are uplifting, worthy of your time and will offer a shoulder to cry on or a pat on the back. My biggest advocates are my immediate family, team and my customers. They have helped me with product development, marketing and I have watched their children grow with our creations.
  3. Not all obvious channels of revenue are the best for a brand. In order to be innovative, I must think outside the box. As a business owner, doing the same thing as everyone else grows tired and boring so I tend to take a moment polling my audience on trends, products and new ideas.
  4. Patience and persistence have turned into profits for me. As a toy brand, many retailers look at our product and compare it to what is already on the market. We use the marketing tactic that if we keep putting our name out there, eventually people will take a chance. This has been proved as our Learning Lovey Collection is now available in many gift and toy stores, zoos and aquariums all over!
  5. Nobody will be more passionate about my business venture than me. My story and voice speak so much truth. Finding the right team to help me communicate that has taken time, but when I finally did, we are able to grow together and reap the rewards.

What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I would love nothing more than to grow our work with organizations bringing cause awareness to supporting military, fire and police as well as advocating for diseases such as pediatric cancer, down syndrome, autism and congenital heart defects. I feel that our business has brought so many people together and we can do so much more with Baby Jack & Co.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My live by quote is that from J.K. Rowling, spoken from Dumbledore — Headmaster in the Harry Potter books series stating happiness can be found even in the darkest of times, if one only remembers to turn on the light. This quote stands for so much in my personal life of battling my own inner dementors with mental health and my professional life of overcoming any obstacles with my business. A positive mindset can help aide in your path to success.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I gravitate towards those in business that are making a difference but seem so real with their online persona. For personal reasons, I would love to sit down with Sara Blakely or Randi Zuckerberg as I admire their accomplishments being a mom and woman in business. Plus, their energy and persona online seem to be authentic and contagious!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

About the Author:

The Thrive Global Community welcomes voices from many spheres. We publish pieces written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Learn more or join us as a community member!
Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Kelley Brooke Gulf Lessons
Community//

How Kelley Brooke Leverages her Golf Lessons to Inspire Women Entrepreneurs

by Jay Block
Community//

Rising Through Resilience: “Mistakes don’t upset resilient people; Rather mistakes fuel resilient people” with Kelley Thornton of Tiege Hanley

by Alexandra Friedman
Community//

#SHEROProject Kelley Kitley’s Story- Breaking Free From Shame

by Dawn Burnett

Sign up for the Thrive Global newsletter

Will be used in accordance with our privacy policy.

Thrive Global
People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.

- MARCUS AURELIUS

We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.