Rachel Sipperly of Rent My Wardrobe | Women Who Inspire

Rachel Sipperly is the woman who self-reportedly “jumped off a cliff and built the plane on the way down.” A successful female entrepreneur located in the South, Rachel is the founder of Rent My Wardrobe and the creator of The Female Founder Podcast

This week, we spoke to Rachel to understand her career story and get the inside tips on her tireless entrepreneurial spirit.

Hustling at the Start

“So I’ve actually always side hustled,” Rachel tells me immediately. Growing up humbly, Rachel was always looking for ways to earn money as a kid. When she graduated from college and began working in sales, her desire to side hustle didn’t stop. She used Airbnb, rented her car out while she was consulting, and more — one year, she made $85,000 just from peer-to-peer side hustling. 

As this was all happening, Rachel identified a need in the market and created Rent My Wardrobe in 2016— a peer to peer platform for renting fashion items (usually for events). At the time, people thought she was crazy. She didn’t have a background in fashion or technology, but knew she was onto something. 

Constant Adjustments

In 2018, they put out their first app for Rent My Wardrobe. Three months later, they completely scrapped it and started fresh. As someone new to the technology world, Rachel was in a constant state of learning. 

“I didn’t have the background. I just saw a need.”

Rachel Sipperly

Rent My Wardrobe has expanded into a membership styling service where, instead addition to renting clothes for events, they help pair you with a stylist and curate an entire head-to-toe look.  

Now, in a Covid-19 world, they’re pivoting, making everything virtual and assessing their next moves. 

“This is the time where million dollar businesses are made,” Rachel says assertively. 

Finding the Why

The “why” is really important to Rachel.

In fact, knowing her why is how she pushes forward through the tough times. “My mission,” she says, “is to empower other women to become incredible entrepreneurs.” Rachel considers the world to have sparse resources for women entrepreneurs — despite the wealth of great ideas women provide.

Enter the Female Founder podcast. Rachel Sipperly is the host, wherein she discusses her tips, tricks, and advice surrounding business owning. It’s a resource guide created by Rachel and informed by her experience, her mentors, and more.

Donna Letier and Rachel Sipperly

Rachel’s why keeps her grounded in her mission: to help women achieve their dreams (from fashion goals to career goals). Donna Letier, Co-founder of Gardenuity was a guest on the podcast – here is a link to their candid conversation- Female Founders


Q: What do you do when you get no’s? How do you push forward?

A: I mean, it is really hard. I’ve been told no thousands of times. You have to have a “why” behind what you’re doing —there must be something bigger behind it or you won’t have the stamina. Definitely, having a support system helps too.

Q: What’s the hardest part about beginning a business? The most satisfying part?

A: You don’t know what you don’t know. That’s simultaneously the best and worst part of having a business. There’s no blueprint for building your business, there’s no one telling you what to do, and there’s no true education around critical thinking in the way that is needed to build a business. So the hard part is not knowing, and the reward is when you figure it out.

As an entrepreneur, you can’t think “outside the box.” You have to think as if there is no box.

Rachel Sipperly

Q: What advice do you have for other women entrepreneurs?

A: 1. Make sure you choose something that you’re really passionate about — something that, if you didn’t make money doing it, you’d do it anyway.

2. Follow your gut and listen to your intuition! It’s our female secret weapon: our primal instinct. I’ve found that when I really embrace my intuition and utilize it, the men around me listen and respect.

Q: What are you learning right now?

A: This year, I’m working on learning to throw your hands up and enjoy the ride (instead of freaking out on the highs and stressing out on the lows). I’m trying to see rejection as a beautiful thing that helps me learn and grow. There are always things out of our control; fighting through these things are what brings us our rewards.

Rachel Sipperly at a Gardenuity Event

Q: Do you garden?

A: Yes! My Gardenuity garden is blowing up — I have so much basil and handfuls of tomatoes! I have never gardened before Gardenuity, but I find it extremely therapeutic and with Gardenuity easy and satisfying.

Listen to Rachel’s podcast here.

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