Female Founders: Jessa Maddocks of JessaKae On The Five Things You Need To Thrive and Succeed as a Woman Founder
An Interview With Candice Georgiadis
Trust your people. Trust is a big one. Trust the people that you work with. Trust your vendors, trust your employees, trust your manufacturers, trust your shipping company.
As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Jessa Maddocks.
Jessa Maddocks is the founder, CEO and head designer of JessaKae, a dress and mommy-and-me brand that focuses on making women of every size feel elegant and powerful. A serial entrepreneur, Jessa combined her love of photography, fashion and design to create JessaKae in 2016, and continues to champion size inclusion in her clothing. Jessa lives in Utah with her two sons and husband, Jordan Maddocks, President of JessaKae.
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I’ve always had an entrepreneurial spirit. I had my own photography business and was always pursuing my own passion projects. So, it just made sense to combine my love for fashion, design, and photography into one business.
Then, I noticed a large population of women were severely missing out because so many brands weren’t inclusive of all sizes. I wanted to make that my personal mission to be a brand for all women with no divisions, whereas most brands have a “regular” size section and a plus-size section.
Having that segregation divides women. It’s telling the plus-size women that they’re not good enough.
So, on my site, I don’t have a plus-size section. It’s just this is our dress and it comes in these sizes.
The way the backstory of JessaKae relates to me personally is that I had a grandma who was plus-size. Growing up, I witnessed firsthand her struggles as a plus-size woman. I would see her flip through catalogs to see if her size was available, order clothing, try it on, and return it. It was eye-opening for me to see that when I was younger.
Can you share the most interesting story that happened to you since you began leading your company?
We recognized early on how few companies were offering dresses for all sizes and representing women of color. We wanted to lead the charge in making these women feel seen.
It’s not a typical thing to see a brand focus on these efforts the way we are at JessaKae, especially when we started in 2016. I’m seeing a lot more brands do it than have in the past, but it’s still something that needs to be improved.
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?
I can’t think of an actual mistake, but I can think of something funny regarding how we got started.
I started JessaKae, with the help of my husband, in our basement apartment with our clothing line taking up tons of space. We replaced all of our furniture with warehouse shelving. And that’s how it operated for six months. It was like we were just living in a warehouse.
I think the biggest lesson with that is we quickly realized how beneficial it was to operate as lean as we could, for as long as we could. It was a big “Aha” moment for us because when we didn’t have any other overhead, we were able to keep buying additional inventory.
That really helped us with extending our runway for the business. We stayed in that basement for as long as we possibly could.
One mistake we did make at the beginning was starting off as a boutique, offering way too many types of products from other companies at the same time.
We quickly learned that we wanted to have our own brand. We didn’t want to be carrying other people’s designs. We wanted to have full control over sizing and the product quality. I think after just being a year into the business, we realized that the direction that we wanted to go was building out our own dress brand.
In a way, we were spreading ourselves thin by carrying so many different products like tops, bottoms, shoes, everything.
The secret we found is to focus on one main product and make that product really good before moving on to other things.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
While JessaKae came from my own passions and ideas, my husband, Jordan, has been my biggest cheerleader, supporter, and worker. I couldn’t do it without him.
My weaknesses are his strengths and his weaknesses are my strengths. We really just come together in that way. All the things I hate doing, he’s good at. And the same for him.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?
I feel like women receive a lot more criticism than men, especially when it’s doing something brave like starting a business.
And the criticism isn’t even just from men.
I remember a woman told me recently, “As a plus-size woman, I would never buy from you because you’re not plus-size.”
That took me by surprise.
I wanted to say, “I’m on your team. I want to help you, support you, and offer you what other companies aren’t.”
The criticism comes from both sides of the spectrum. Even when we’re trying to help each other, I feel like women definitely receive a lot more criticism than men do. No matter what type of business it is.
Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?
We need to develop a stronger support system for female founders and entrepreneurs. Women are really powerful, but we can also be fiercely, and unnecessarily, competitive. I feel like supporting one another, and women working harder to lift each other up, is what we can do as a society.
There’s room for everyone in the industry. There are so many people in the world trying to start businesses and I see my competitors, but I don’t wish ill upon them.
I urge people to buy from other female-owned businesses, including ones in my own industry. I’m happy to support them.There is room for everyone.
I know there are also government-sponsored programs that I feel could be purposed more towards minority groups and female founders. We need more opportunities in general. Whether it’s for grants or different opportunities like that.
Sometimes that’s all that it takes to give people an opportunity, especially those in minority situations. Having those types of programs available makes it super transparent. I think that’s a huge deal.
This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?
Women are so creative and the world often suppresses the creativity they have to offer. The world needs their ideas, visions, and leadership. Female founders can provide those to any and all industries.
What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?
You hear a lot about quick success. Many people want to believe that things happen overnight and that’s never really the case.
Everything you do in your life leads you up to a moment. For me, my photography and my love of fashion snowballed me to where I am.
There was a slow buildup to my success. That’s more common and realistic than gaining overnight success.
Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?
I think everyone could be a founder if they’re willing to put in what it takes to be successful. But it definitely takes a lot of grit, perseverance, and discipline to be a founder and own a business. Especially for a female founder.
It’s a lot harder because you have to separate your personal life from your work life. A lot of the time, these two aspects of life intermingle with each other. And then when times get hard, you have to figure out new solutions and be optimistic that these pivots will get you where you need to go.
Another big myth is that it’s going to be easy. When really, you’re working twice as hard as you do during a normal 9 to 5. You’re working longer hours. There’s a lot more uncertainty and you have to continue on, despite the fact that the whole world might seem like it’s caving in and you still have to continue pushing forward.
Anyone can be a founder. You just have to be willing to do what’s necessary to make it work and overcome obstacles, and know your strengths. You can have an idea and then someone else can run with it as you delegate tasks and responsibilities properly.
Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
1. Focus on one thing when you’re first starting.
2. Hiring good people is difficult but crucial to your success — Finding your “ride or die” people is vital to running your business
3. Persevere through the difficult times — There will be times when it seems the whole ship is imploding — Continue on and persevere.
4. Don’t let negativity get you down — Negative comments from competitors, customers, social media, etc.
5. Trust the people you work with and the professional relationships you build — Partners, vendors, shipping, manufacturer (quality), etc.
One of them we already discussed is to focus on one main product. You should perfect one thing before moving on to the next. We started with way too many products at once and became overwhelmed with the management involved in running our business that way. It wasn’t until we focused on only one thing at a time that we really started seeing growth and success.
Second, I would say that hiring good people is really difficult. But finding your “ride-or-die people” that will stick with you is crucial to running a business. We have had experiences where we have hired the wrong people and see what a negative effect it can have on a business.
There was somebody that lived out of state interested in hiring for a marketing position. We knew that marketing was something we really needed to master and was really important for reaching the next level of success. So, we started taking in applications and found somebody claiming to have all the credentials and experience we were looking for. We got on the phone with them. Everything sounded great.
Long story short, we ended up moving them to Utah. And then, on their first day of work, it took very little time for us to realize they weren’t what they said they were. It was really tough and we ended up firing them shortly after. Luckily, we ended up hiring a really good person who completely changed the trajectory of our whole business. We spent a lot more time in that investigation phase vetting them out and asking certain types of questions that could give us some qualitative information on who they were. It’s just interesting how those hires can lead to such a big difference in the end.
Third, I would say it’s important to know there are going to be times when it seems like the whole ship is imploding. And when things seem to be at their absolute worst, it could always be a level worse than that. It helps to know this ahead of time because it makes a founder less likely to make the hole deeper for themselves than it already is. My advice would be to continue on and persevere through these struggles, allowing them to make you stronger along the way.
Fourth, I would urge female founders to not let the negativity get them down. You’re always going to get pushback and negative comments from people. From competitors, from customers, and especially from social media. Don’t let other people bring you down or control the way you feel about what you’re doing.
Fifth, trust your people. Trust is a big one. Trust the people that you work with. Trust your vendors, trust your employees, trust your manufacturers, trust your shipping company.
But also make sure that you maintain a sense of awareness. Build professional relationships that are based on mutual trust and mutual value.
How have you used your success to make the world a better place?
We’ve worked incredibly hard to make our brand inclusive of women of all sizes. Early on in our business, we reinvested our money in growing our size range.
We’re a brand that’s very “ear to the ground”. We listen to customers’ feedback on our pieces and our fittings. We’ve taken that feedback and invested it into research and getting the measurements just right. Plus sizing is a whole other ballpark in and of itself. We are constantly reinvesting our money into making our company inclusive of all women.
I get weekly comments about our photoshoots as we always try to include multiple body types and sizes. For example, I was recently in San Francisco and we were shooting in this public garden. I had two people stop me and say, “Wow, I can see how this dress looks on someone like me. They’re not just a skinny, tall model. It’s someone that looks just like me.”
We get comments like that a lot. And we love it. We see the difference we’re making and the people we’re helping.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
The movement I would love to inspire is holistic size inclusion for women in the entire fashion industry. When I was in the middle of starting JessaKae, it opened my eyes and I realized how truly deep the lack of size inclusion was. I would go to markets and there were thousands and thousands of brands with only small, medium, and large sizes. There might have been two booths in the entire convention carrying plus sizes. Even today, designer brands only go up to an XL. The average American woman is around a size 16. At JessaKae, all our dresses are consistently in sizes ranging from XXS to 5XL, and we’re very excited to be working on 6XL.
I’d love to just get rid of the term “plus-size” altogether, like plus-size stores or plus-size sections on the website. A brand should just make their piece of clothing and adjust it so it fits every size for women. We do it. It’s possible.
We are very blessed that some very prominent 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.
There are so many amazing women in business who have achieved great things. But the woman I have noticed who has been really good in her business ventures is Jessica Alba. I follow her brand, The Honest Company, closely and would love to pick her brain on business and the way she has reached such a high level of success.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this!
Female Founders: Jessa Maddocks of JessaKae On The Five Things You Need To Thrive and Succeed as a… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.