Doing the Thing You Can’t Stop Thinking About: Jessie Randall

Jessie Randall is the co-founder of super-chic, eponymous accessories brand, Loeffler Randall. Jessie was kind enough to stop by our pitch night and share her founder story with us in a Q&A, and give advice to the women who were pitching their businesses. She was honest, smart, and every bit as effortlessly stylish as you’d imagine. We rounded up some of her story highlights.

On getting her start 

One piece of advice someone gave me was that you’ve got to do the thing that you can’t stop thinking about. I remember at one point we [Jessie and her co-founder and husband, Brian] were thinking about creating cleaning supplies in our own aesthetic. But I hate cleaning! Why would I start a company around cleaning? So we started to focus more on design because that was my job and I started out designing handbags and my husband said, “You have to do shoes, you’re obsessed with shoes”

So, I signed up for a shoemaking course in New York. I was a designer and had had some really great training, but I hadn’t made shoes before. So I started making my own shoes in this class. I was baking the [shoe] lasts in my toaster oven. We had found an agent in Italy to work with, and I was hand-making these molds at home and sending them to her saying, “This is the toe shape that I want!”. 

We were planning out this company for about a year. We were doing so much work and investing all our money in this idea. It was really scary and we had to be really strong.

On taking advice on your business idea at the beginning

I thought every time someone told me I was going to fail, I’d flip it in my mind and tell myself to prove them wrong. 

We limited the amount of advice we took from people. We did ask for a ton of advice from people who had an aesthetic we respected. I remember Andy Spade, one of Brian’s friends, was so sweet. He took us out to the Carlyle hotel bar and took the time to sit with us and we really listened to him. 

It’s really good to get input but figure out who to get advice from on various things. I’d be willing to listen to certain people about other topics like finances, but not about whether or not we could start a shoe company. 

On some factors that gave them success early on

One piece of advice I got was to have a business partner with a different skill set than I have. My husband is an art director, but he also worked in banking and is a math genius. He does all of the business side and I do all of the design side, which is a really nice division of labor.

We also brought on a business advisor at the beginning. It was so critical. He negotiated our contract with our showroom with us. I have friends who have started a fashion business and a buyer comes in and they buy way too much product and they’re selling with a sell-through agreement. He had a huge amount of experience and really had our backs to make sure we didn’t get taken advantage of when we first started out.

On early challenges

I didn’t have a merchandiser for the first six years, and I introduced our first hit product–a white python boot in spring. If I had had a merchandiser, maybe they would’ve told me to hold it until fall and make it black!

[When I started] you couldn’t sell to every store that wants to take your product in the same geographic area…They wanted the exclusivity, and you had to choose which store you want to sell to, and that limits how much you can sell. You had to choose the right one, the one that’s going to pay their bills, or that’s going to stay in business the longest.

On the changing retail landscape

The retail landscape has changed so much. We have a really nice business with most of the higher-end retailers now. E-commerce has changed things so much…It’s not that you can’t sell to everybody, but everybody wants a different assortment, and to make sure that no one else is marking things down before they are.

It’s never been easier to start a company, but it’s also never been harder. Everyone can have an Instagram page, and everyone can have a website. You don’t need to rely on wholesale anymore. But I have friends who start businesses who say they’re just going to sell direct, and I ask, ‘how is anyone going to know about your website?’…the numbers that [the big DTC brands] spend on marketing is so crushing. You’re up against $40,000 a month on digital spend. That part of it is really hard. 

On two final pieces of advice

Don’t give away too much equity to someone you think you need really early on. Everyone is replaceable, and it’s hard to conceive how big your company is actually going to be. 

It’s so important to have some kind of background in the field you’re in. I still rely so much on the skills I learned in jobs that at the time felt really boring or demoralizing. I learned so much that I still use; doing HR, marketing, creating a retail map. I’m really grateful that I put the time in to get a real concrete foundation and didn’t come straight out of college thinking about starting a shoe company.