We were lucky to catch up with Jessica Davidoff recently and have shared our conversation below.

Jessica, appreciate you joining us today. We’d love to have you retell us the story behind how you came up with the idea for your business, I think our audience would really enjoy hearing the backstory.

After selling my third business and having my son, I started to retire my blazers and shorter skirts and instead opted for the ease and versatility of long dresses. The only problem was my NYC closet became a total disaster! I tried hanging them on the top rack and the bottoms would get snagged by hangers or would cover all the clothes on the bottom rack. I tried hanging them on the bottom rack and the bottoms would get wrinkled and covered in dust bunnies. So I searched for a solution and to my surprise, there were NO hangers on the market designed specifically for long garments! I decided to change that and patented my first product – the Cove long garment hanger – during the pandemic. We’re the first and only hanger on the market that allows you to hang long dresses on the short rack of your closet. It was a real challenge perfecting the design and bringing it to market, but after about two years of prototyping, we finally launched Cove in the spring of 2022 and it’s been a dream ever since!

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I’ve been an entrepreneur since I was 22 years old. I graduated from Princeton and instead of taking any of the management consulting job offers that I had, I decided to work for a small SAT prep company as a Director. It was a fantastic crash course in small business management and interestingly, it happened to be the year the SAT changed. I had a hypothesis that a lot of students would want to take the ACT as a back up so I wrote proposal for the owner of the company that I wanted to write ACT prep curriculum and create an ACT prep course. He thought I was crazy and said no one in NY would ever take the ACT. I quit on the spot, and got a bartending job for 6 months and wrote my curriculum and business plan during the day and then launched my first business, The Edge. I grew it to 3 international locations before selling the curriculum and pivoting to launch a new education technology app that matched high school students to colleges and provided free college prep curriculum. I raised a round of venture funding and grew it to 250,000 students, and then sold that company to ACT. After working for 2 years post-acquisition and growing our student userbase to 6M students, I left to launch a brand incubation and growth studio called Easton Rae. We launched and grew several beloved consumer brands and I took the helm of STATE Bags, Tropic of C, and Violet Grey as an interim CEO or Chief Business Officer, before incubating and launching Cove. I know I’ll be a lifelong entrepreneur and will continue riding this beautiful wave!

Can you talk to us about your experience with selling businesses?

I’ve now sold several businesses – some that I founded and others that I had taken over as CEO and the biggest lesson I’ve taken away is to stop thinking of your company as your baby. It has become so commonplace to refer to companies as people’s babies, but after being a mom to an incredible boy (with another one on the way!), I know full well that being a mom to a human is NOTHING like owning a business.

First of all, it doesn’t make sense – literally ZERO thought goes into making a human baby, it’s a lot of magic and a lot of fun 😉 if you get to do it the natural way – but you’re not designing every detail of your child the way you do when building a brand, which can take YEARS of planning.⁠
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More importantly, having that level of attachment to your business can make hard times even harder.⁠
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You’d never sell your baby, you’d never “shut down” your baby, or give up on it, or move on to your next endeavor, so thinking about your business as your baby makes it really hard to do hard things, even when they’re the right thing to do.⁠
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Personally, I’ve launched 5 brands of my own with a 6th on the way, and I like to think of them more like songs or pieces of art. ⁠
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I know that I wrote the song, and painstakingly perfected it until I felt comfortable putting it out into the world, but then it became something for everyone to engage with and feel a little bit of attachment to, and maybe someone wants to create the remix, or completely make it their own in a cover, and that’s awesome.⁠
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And sometimes the songs we write will be greatest hits that will remain favorites for decades, and other times they’ll be short-lived bops that we never really want to hear again after they get played out, and others are one hit wonders that explode onto the scene like fireworks.⁠

For me, it makes selling my companies MUCH easier when I lose the “my company is my baby” attachment and realize that I’m ready to let someone make my business their own.

What else should we know about how you took your side hustle and scaled it up into what it is today?

My first side hustle that turned into a real business was an app that I co-created called Golfmatch. It was basically like bumble, but instead of looking for a date, you could use it to find a golf buddy and book a tee time. We honestly created it while we were both working full time and it was born out of a true need – I had no friends who golfed, and my co-founder was so freaking good at golf that he wanted to find other insanely amazing golf buddies to play with. So we did it on the side and it blew up. We grew to about 25,000 users really quickly because we were solving a pain point that happened to be shared by a lot of other golfers.

We ended up raising some outside capital for it and then Topgolf bought it, and my co-founder is still working there today. I would say that the key reason a side hustle will turn into a real business is if you are focused on solving a real problem that a lot of people share, and you do it in a way that really resonates at a price point that makes sense. Then you’ll grow organically to the point where you’ll probably be able to focus on it full time!

Contact Info:

• Website: www.createyourcove.com
• Instagram: @createyourcove
• Facebook: www.facebook.com/createyourcove
• Linkedin: www.linkedin.com/in/jessbrondo
• Twitter: @createyourcove
• Youtube: https://www.youtube.com/channel/UC4CMyDMPaqQiBBwxo4RcY6A

Image Credits
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